JP7779671B2 - Anthracene Compounds - Google Patents

Description

The present invention relates to an anthracene compound, an organic electroluminescent device using the same, and a display device and lighting device using the same.

Display devices using electroluminescent light-emitting elements have been the subject of extensive research due to their potential for power saving and thinning. Furthermore, organic electroluminescent elements (hereinafter sometimes referred to as organic EL elements) made from organic materials have been actively investigated due to their ease of being lightweight and large-sized. In particular, there has been active research into the development of organic materials with luminescent properties, such as blue, one of the three primary colors of light, and the combination of multiple materials that result in optimal luminescent properties, regardless of whether they are polymeric or low-molecular-weight compounds.

Organic EL elements have a structure consisting of a pair of electrodes, an anode and a cathode, and one or more layers containing organic compounds, disposed between the pair of electrodes. Layers containing organic compounds include light-emitting layers and charge transport/injection layers that transport or inject charges such as holes and electrons, and a variety of organic materials suitable for these layers have been developed.

In recent years, polycyclic aromatic compounds in which multiple aromatic rings are fused with a central atom such as boron have been reported as materials for light-emitting layers (Patent Document 1). Furthermore, Patent Document 2 reports that excellent organic EL devices can be obtained by constructing an organic EL device by placing an emitting layer containing this polycyclic aromatic compound as a dopant material and a specific anthracene compound as a host material between a pair of electrodes.

International Publication No. 2015/102118 International Publication No. 2016/152544

As disclosed in the above patent documents, a variety of materials and combinations have been developed for use in organic EL elements. By further exploring various materials and combinations, it is expected that organic EL elements will be provided that not only have the desired color-developing characteristics, but also have more practically desirable properties. An objective of the present invention is to provide novel materials that can be used in the manufacture of organic devices such as organic EL elements.

As a result of extensive research to solve the above-mentioned problems, the inventors discovered a novel anthracene compound with a specific substituent. They then discovered that by using this compound as a host compound and forming an emissive layer using a dopant compound such as a polycyclic aromatic compound in which multiple aromatic rings are fused with boron as the central atom, an organic electroluminescent device with improved energy efficiency can be obtained. Based on this finding, they have completed the present invention.

Specifically, the present invention has the following configuration:

<1> An anthracene compound represented by the following formula (1):

In formula (1),
any n of R ¹ to R ¹⁰ are bonded to L as bonds to L,
R ¹ to R ¹⁰ other than the n bonds are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
one of any two ^Z1's is a carbon bonded to Tph and the other is a carbon bonded to L, Tph is a group represented by formula (Tph),
Other Z ^1's are each independently N or C-R ¹¹ , and R ¹¹ 's are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded via a linking group), substituted or unsubstituted arylheteroarylamino (an aryl and a heteroaryl may be bonded via a linking group), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted substituted silyl,
adjacent groups among R ¹¹ may be bonded to each other to form an aryl ring optionally substituted with R ¹² or a heteroaryl ring optionally substituted with R ¹² , R ¹² has the same meaning as R ¹¹ , but does not represent hydrogen and adjacent groups do not bond to each other to form a ring;
X ¹ and X ² each independently represent a single bond, >O, >S, >N—R, >C(—R) ₂ , >Si(—R) ₂ , or >Se, and R in the >N—R, >C(—R) ₂ , and >Si(—R) ₂ each independently represent a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl;
two Rs in the >C(—R) ₂ or >Si(—R) ₂ represented by X ¹ or X ² may be bonded to each other to form a ring,
R in the >N-R as ^X1 or ^X2 may be bonded to any R ¹¹ via a linking group or a single bond,
L is bonded to any one of ^Z1 and is bonded to a carbon atom constituting the anthracene ring via any one of ^R1 to ^R10 ;
L is a single bond, a substituted or unsubstituted alkylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
n is an integer from 1 to 3,
when n is 2 or 3, a plurality of L's, a plurality of X ^'s , a plurality of X ^'s and a plurality of R ^'s may be the same or different from one another;
In the formula (Tph),
Any one of ^Z2 is a carbon bonded to ^Z1 , which is also a carbon;
Other ^Z2 are each independently N or C- ^R22 , and ^R22 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded via a linking group), substituted or unsubstituted diheteroarylamino (two aryls may be bonded via a linking group), substituted or unsubstituted arylheteroarylamino (two aryls may be bonded via a linking group), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted substituted silyl,
At least one hydrogen atom in the compound represented by formula (1) may be substituted with a substituted silyl, cyano, halogen, or deuterium.

<2> All other Z ¹ 's are C—R ¹¹ , and all R ¹¹ 's are hydrogen;
The anthracene compound according to <1>, wherein all other Z ^2s are C—R ^22s , and all R ^22s are hydrogen.
<3> The anthracene compound according to <1> or <2>, wherein L is a single bond.

<4> An anthracene compound according to any one of <1> to <3>, represented by the following formula (1A), the following formula (1B), the following formula (1C), the following formula (1D), or the following formula (1E):

In formula (1A), formula (1B), formula (1C), formula (1D) and formula (1E), R ¹ , R ² , R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , Z ¹ , X ¹ , X ² , L and Tph have the same meanings as R ¹ , R ² , R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , Z ¹ , X ¹ , X ² , L and Tph in formula (1), respectively.

<5> The anthracene compound according to <4>, represented by formula (1A) or formula (1C):
<6> R ¹ , R ⁸ , and R ⁹ are each independently hydrogen or alkyl having 1 to 24 carbon atoms;
<5> The anthracene compound according to <5>, wherein R ² , R ³ , R ⁶ , and R ⁷ are each independently an aryl having 6 to 30 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms.

<7> The anthracene compound according to <6>, which is represented by any one of the following structural formulas:

<8> An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains the anthracene compound described in any one of <1> to <7>.

<9> The organic electroluminescent device according to <8>, wherein the light-emitting layer further contains a polycyclic aromatic compound represented by the following formula (D) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (D):

In formula (D),
Ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted;
^X1 and ^X2 are each independently >O, >C(-R) ₂ , or >N-R, R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >N-R may be bonded to at least one of the rings A, B, and C via a linking group or a single bond, and R of the >C(-R) ₂ are each independently an aryl optionally substituted with alkyl or cycloalkyl, a heteroaryl optionally substituted with alkyl or cycloalkyl, an alkyl, or cycloalkyl, and two R in the >C(-R) ₂ may be bonded to each other to form a ring;
In the compound represented by formula (D) or a multimer thereof, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one —CH ₂ — in the cycloalkane may be substituted with —O—;
In the compound represented by formula (D) or a multimer thereof, ring B and ring C may be bonded via a single bond or —O—, —S—, or —C(—R) ₂ —, where R in —C(—R) ₂ — is hydrogen, alkyl, or cycloalkyl, and the two Rs may be bonded to each other to form a ring; and
At least one hydrogen atom in the compound represented by formula (D) or a polymer thereof may be substituted with cyano, halogen or deuterium.

<10> The organic electroluminescent device according to <8>, wherein the light-emitting layer further contains a polycyclic aromatic compound represented by the following formula (DB) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (DB):

In formula (D-B),
Ring A1, ring A2, and ring A3 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring, provided that at least one of ring A1, ring A2, and ring A3 is an aryl ring or a heteroaryl ring;
At least one selected from the group consisting of aryl rings and heteroaryl rings may be fused with at least one cycloalkane;
At least one hydrogen atom in the compound represented by formula (DB) or a polymer thereof may be substituted with cyano, halogen or deuterium.

<11> A display device or lighting device comprising the organic electroluminescent device described in any one of <8> to <10>.

The present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent devices. This compound can be used to provide highly efficient, long-life organic EL devices.

FIG. 1 is a schematic cross-sectional view illustrating an example of an organic EL element.

The present invention is described in detail below. The following explanation of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, numerical ranges expressed using "to" mean a range that includes the numerical values before and after "to" as the lower and upper limits. In addition, in this specification, "hydrogen" in explanations of structural formulas means "hydrogen atom (H)," "deuterium" means "deuterium atom (D)," and "carbon" means "carbon atom (C)."

As used herein, the term "adjacent groups" refers to two groups bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in a structural formula.

In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent, or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in the chemical structure or the substituent, and does not refer to the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X," and carbon number Y is not the total number of carbon atoms in substituents A and B. For example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (with no carbon number restriction)," and carbon number Y is not the total number of carbon atoms in substituents A and B.

<<Anthracene Compound Represented by Formula (1)>>
The anthracene compound of the present invention is represented by the following formula (1).
The present inventors have found that an anthracene compound including an anthracene skeleton, a fused ring structure represented by formula (A) such as dibenzofuran, and a monovalent group represented by formula (Tph) consisting of a fused tetracyclic ring structure such as triphenylene, can provide high quantum efficiency when used in the light-emitting layer of an organic electroluminescent device.

The anthracene compound represented by formula (1) has a structure in which n groups represented by the following formula (1Sub) are bonded to an anthracene skeleton. In formula (1), in addition to the n groups represented by formula (1Sub) in formula (1), R ¹ to R ¹⁰ (excluding those which serve as bonds) are bonded to the anthracene skeleton, but none of them is a group corresponding to the group represented by formula (1Sub).

In formula (1Sub), * indicates the bond position.

In formula (1Sub), one of any two Z ^1s is a carbon bonded to Tph, and the other is a carbon bonded to L.
Each of the other Z ^1s is independently N or C-R ¹¹ , and each of R ¹¹ is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded via a linking group), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded via a linking group), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted substituted silyl. However, adjacent groups within R ¹¹ may be bonded to form an aryl ring optionally substituted with R ¹² or a heteroaryl ring optionally substituted with R ¹² . Here, the ring formed is a ring formed by ^R11 together with the carbon atoms to which adjacent ^R11 are bonded, and is a ring constituting a part of the fused ring represented by formula (A). ^R12 has the same meaning as ^R11 , but does not represent hydrogen and adjacent groups do not bond to each other to form a ring.

Examples of the aryl ring in the "aryl ring which may be substituted with R ¹² " formed by bonding adjacent groups among R ¹¹ together include a benzene ring, a naphthalene ring, etc. Examples of the heteroaryl ring in the "heteroaryl ring which may be substituted with R ¹² " formed by bonding adjacent groups among R ¹¹ together include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, etc.

As described above, ^specific examples of the fused ring represented by formula (A) in the case where adjacent groups among R ¹¹ are bonded to each other to form an aryl ring which may be substituted with R ¹² or a heteroaryl ring which may be substituted with R 12 include fused rings represented by any of the following formulas (A-1) to (A-11).

In formulae (A-1) to (A-11), Z ¹ is N, C—H, or C—R ^12. R ¹² has the same meaning as R ¹¹ , but does not represent hydrogen, and adjacent R ¹² do not bond to each other to form an aryl ring or heteroaryl ring.

When the ring formed as described above contains Z ¹ which is N, the formed ring is a heteroaryl ring, and when Z ¹ in the formed ring is both C—H or C—R ¹² , the formed ring is an aryl ring.

In formula (1Sub), it is preferred that Z ¹ other than Z ¹ which is carbon is each independently C—R ¹¹ .

R ¹¹ is preferably hydrogen, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted alkyl, and more preferably hydrogen, an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or a monovalent group (described below) obtained by removing any hydrogen from a compound represented by formula (BO) which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms. R ¹¹ is more preferably hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or an alkyl having 1 to 24 carbon atoms, and particularly preferably hydrogen or an aryl having 6 to 30 carbon atoms. It is most preferable that ^{R 11} is hydrogen.

In formula (1Sub), ^X1 and ^X2 each independently represent a single bond, >O, >S, >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >Se. R in the >N-R, >C(-R) ₂ , and >Si(-R) ₂ each independently represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Two R in the >C(-R) ₂ or >Si(-R) ₂ representing ^X1 or ^X2 may be bonded to each other to form a ring.

In formula (1Sub), the two Rs in the >C(-R) ₂ or >Si(-R) ₂ represented by ^X1 or ^X2 may be bonded to each other to form a ring. Specific embodiments in which ^X1 in formula (A) is >C(-R) ₂ or >Si(-R) ₂ and the two Rs are bonded to each other to form a ring are shown below.

In formula (1Sub), R in the >N-R as ^X1 or ^X2 may be bonded to any R ¹¹ via a linking group (for example, >C(-R) ₂ , >O, >S or >N-R) or a single bond. The R ¹¹ to be bonded is preferably R ¹¹ in Z ¹ adjacent to the carbon to which N in the >N-R is directly bonded. This embodiment is specifically represented, for example, as follows:

In formula (1Sub), ^X1 and ^X2 are preferably each independently a single bond, >O, >S, >N-R, or >C(-R) ₂ . In this case, R in the >N-R and >C(-R) ₂ is preferably each independently an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. It is more preferable that ^X1 and ^X2 are each independently a single bond, >O, >S, >N-R (R is phenyl), or >C(-Me) ₂ , and even more preferably a single bond, >O, or >C(-Me) ₂ .

It is preferable that either ^X1 or ^X2 is a single bond. When either ^X1 or ^X2 is a single bond, the other is preferably >O, >S, >N—R or >C(—R) ₂ , more preferably >O, >S or >C(—R) ₂ , even more preferably >O or >S, and most preferably >O.

In formula (1Sub), the fused ring represented by formula (A) is most preferably a dibenzofuran ring.

In formula (1Sub), Tph is a monovalent group having a bond on ^Z2 in any one of the structures represented by formula (Tph) below.

In formula (Tph), any one Z ² is a carbon bonded to Z ¹ , which is carbon. The other Z ² are each independently N or C-R ²² , and R ²² are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (the two aryls may be bonded via a linking group), substituted or unsubstituted diheteroarylamino (the two aryls may be bonded via a linking group), substituted or unsubstituted arylheteroarylamino (the two aryls may be bonded via a linking group), substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted substituted silyl. The other Z ² are each independently N or C-R ²² , and it is preferable that each is independently C-R ²² . R ²² is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted alkyl, more preferably hydrogen, substituted or unsubstituted aryl, and most preferably hydrogen. More specifically, R ²² are each independently a monovalent group obtained by removing hydrogen from any of hydrogen, aryl having 6 to 30 carbon atoms which may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, heteroaryl having 2 to 15 carbon atoms which may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a compound represented by formula (BO) which may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. ^R22 is preferably hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or alkyl having 1 to 24 carbon atoms, more preferably hydrogen, or aryl having 6 to 30 carbon atoms, and even more preferably hydrogen for all. That is, Tph is most preferably unsubstituted triphenylenyl.

Preferred examples of groups represented by the following formula (1Sub'), excluding L in formula (1Sub), are shown below. In each formula, * indicates the bonding position with L.

In formula (1Sub), L is a single bond, a substituted or unsubstituted alkylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene. In formula (1Sub), L is bonded to any of ^Z1 . In formula (1), L is further bonded to a carbon atom constituting the anthracene ring via any of ^R1 to ^R10 as a bond. That is, in formula (1), the group represented by formula (1Sub) is bonded to the anthracene skeleton via any of ^R1 to ^R10 as a bond.

L is preferably a single bond, an arylene optionally substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, or a heteroarylene optionally substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms.

Specific examples of L include a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 2,4-biphenylylene, and 2,7-phenanthrylene.
L is most preferably a single bond.

In formula (1), n is an integer of 1 to 3. However, when n is 2 or 3, multiple formulas (1Sub) may be the same or different from each other. That is, multiple Ls, multiple X ^1s , multiple X ^2s , and multiple R ^11s may be the same or different from each other. It is most preferable that n is 1.

In formula (1), n of R ¹ to R ¹⁰ are bonds to L.
The n R ¹ to R ¹⁰ other than the bonds are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Preferably, R ¹ to R ¹⁰ other than the n bonds are each independently hydrogen, an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, more preferably, they are each independently hydrogen, an unsubstituted aryl having 6 to 30 carbon atoms, or an unsubstituted heteroaryl having 2 to 30 carbon atoms, and even more preferably, they are each independently hydrogen, an unsubstituted aryl having 6 to 12 carbon atoms, an unsubstituted heteroaryl having 2 to 12 carbon atoms, or a monovalent group (described later) obtained by removing hydrogen from any of the compounds represented by formula (BO).

It is particularly preferred that R ¹ to R ¹⁰ other than the bond are each independently hydrogen, phenyl, naphthyl (1-naphthyl, 2-naphthyl), biphenylyl (3-biphenylyl, 4-biphenylyl, etc.), terphenyl, dibenzofuranyl, benzonaphthofuranyl, phenyl-substituted naphthyl, or naphthyl-substituted phenyl, and it is preferred that R ¹ to R ¹⁰ other than the bond are all hydrogen, or all but one or two are hydrogen.

At least one hydrogen atom in the anthracene compound represented by formula (1) may be substituted with a halogen atom, cyano, or deuterium, and substitution with deuterium is more preferred.

In the anthracene compound represented by formula (1), the proportion of deuterium relative to the total number of hydrogen and deuterium bonded to carbon atoms constituting the aromatic ring in one molecule (100%) is preferably 10-100%, more preferably 30-100%, even more preferably 50-100%, still more preferably 80-100%, and particularly preferably 100%. It is also preferable that all hydrogen atoms directly bonded to carbon atoms constituting the anthracene ring are deuterium, and a more preferable embodiment is one in which all hydrogen atoms directly bonded to elements constituting the aromatic ring are deuterium.

The above phrase "hydrogen and deuterium bonded to carbon atoms (ring carbon atoms) that constitute an aromatic ring in one molecule" refers to hydrogen and deuterium bonded directly to a ring carbon atom, and does not include hydrogen and deuterium bonded to a ring carbon atom via a linking atom such as carbon or nitrogen, such as the hydrogen and deuterium in a substituent bonded to the ring carbon. For example, in the case of compound (1-91) below, there are 38 "ring carbon atoms that can bond to hydrogen atoms that constitute an aromatic ring in one molecule," of which 21 are bonded to "deuterium (D)" and 17 are bonded to "hydrogen (H)." Therefore, the above-mentioned "proportion of deuterium" in compound (1-91) is approximately 55.3% (≒ 21/(21 + 17) × 100).

For example, in the case of compound (1-392) below, the number of "carbon atoms (ring carbon atoms) that can bond to hydrogen atoms that make up an aromatic ring in one molecule" is 30, of which 30 are bonded to "deuterium (D)." Furthermore, the hydrogen atoms in methyl do not fall under the category of "hydrogen atoms that bond to carbon atoms that make up an aromatic ring (ring carbon atoms)," so they do not need to be taken into account. Therefore, the "percentage of deuterium atoms" in compound (1-392) is 100% (= 30/30 x 100).

Also preferred is a form in which all hydrogen atoms substituted on the carbon atoms constituting the anthracene ring are replaced with deuterium atoms.

Preferred examples of the anthracene compound represented by formula (1) include compounds represented by formula (1A), formula (1B), formula (1C), formula (1D), or formula (1E).

In formula (1A), formula (1B), formula (1C), formula (1D) and formula (1E), R ¹ , R ² , R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , Z ¹ , X ¹ , X ² , L and Tph have the same meanings as R ¹ , R ² , R ³ , R ⁶ , R ⁷ , R ⁹ , R ¹⁰ , Z ¹ , X ¹ , X ² , L and Tph in formula (1), and the preferred ranges are also the same.

In formula (1A), formula (1B), formula (1C), formula (1D) and formula (1E), R ¹ , R ² , R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently hydrogen, an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an aryl having 6 to 30 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms. [0049] It is preferably a monovalent group obtained by removing hydrogen from any of the compounds represented by formula (BO) which may be substituted with aryl, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, and more preferably hydrogen, phenyl, naphthyl (1-naphthyl, 2-naphthyl), biphenylyl (3-biphenylyl, 4-biphenylyl, etc.), terphenyl, dibenzofuranyl, benzonaphthofuranyl, phenyl-substituted naphthyl, or naphthyl-substituted phenyl.

The compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) is more preferably a compound represented by formula (1A) or formula (1C). In the compound represented by formula (1A) or formula (1C), R ² , R ³ , R ⁶ and R ⁷ are each preferably independently hydrogen or alkyl having 1 to 24 carbon atoms, more preferably hydrogen. In the compound represented by formula (1A) or formula (1C), R ¹ , R ⁸ , and R ⁹ are preferably each independently an aryl having 6 to 30 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms, and more preferably phenyl, naphthyl (1-naphthyl, 2-naphthyl), biphenylyl (3-biphenylyl, 4-biphenylyl, etc.), terphenyl, dibenzofuranyl, benzonaphthofuranyl, phenyl-substituted naphthyl, or naphthyl-substituted phenyl.

When referring to the compound represented by formula (1), the term "aryl" refers to, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, even more preferably an aryl having 6 to 16 carbon atoms, particularly preferably an aryl having 6 to 12 carbon atoms, and most preferably an aryl having 6 to 10 carbon atoms.

Specific examples of aryl include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-)biphenylyl, fused bicyclic aryl (1-, 2-)naphthyl and (2-, 3-, 4-, 5-, 6-, 7-)indenyl, and tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl). acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, which are fused tricyclic aryls; quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl), which are tetracyclic aryls; Examples include fused tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

When referring to the compound represented by formula (1), the term "heteroaryl" refers to, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, even more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalyl, phthalazyl, naphthyridyl, pryl, pteridyl, carbazolyl, and azolyl. Examples of heteroaryl include acridyl, phenoxathiylyl, phenoxazyl, phenothiazyl, phenazyl, phenazilyl, indolizyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, dinaphthothienyl, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, benzobenzoindolocarbazolyl, dioxinyl, dihydroacridinyl, xanthenyl, thioxanthenyl, and dibenzodioxinyl. Heteroaryl also includes monovalent groups obtained by removing any hydrogen from a compound represented by the following formula (BO):

Examples of the monovalent group obtained by removing any hydrogen from a compound represented by formula (BO) include the following groups. In the formula, * indicates the bonding position.

When describing the compound represented by formula (1), the "alkyl" may be either linear or branched, and examples include linear alkyls having 1 to 24 carbon atoms or branched alkyls having 3 to 24 carbon atoms. Alkyls having 1 to 18 carbon atoms (branched alkyls having 3 to 18 carbon atoms) are preferred, alkyls having 1 to 12 carbon atoms (branched alkyls having 3 to 12 carbon atoms) are more preferred, alkyls having 1 to 8 carbon atoms (branched alkyls having 3 to 8 carbon atoms) are even more preferred, alkyls having 1 to 6 carbon atoms (branched alkyls having 3 to 6 carbon atoms) are particularly preferred, and alkyls having 1 to 5 carbon atoms (branched alkyls having 3 to 5 carbon atoms) are most preferred.

Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

In describing the compound represented by formula (1), "alkylene," "arylene," and "heteroarylene" include divalent groups obtained by removing a hydrogen atom from any of the "alkyl," "aryl," and "heteroaryl" groups described above. Preferred alkylene groups are methylene and ethylene, preferred arylene groups are phenylene and naphthalene, and preferred heteroarylene groups are dibenzofuranylene. Phenylene, naphthalene, and dibenzofuranylene are more preferably unsubstituted.

When referring to "cycloalkyl" in the description of the compound represented by formula (1), examples of "cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

When describing the compound represented by formula (1), "alkenyl" refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is typically in the range of 2 to 20.

When referring to the compound represented by formula (1), the term "alkoxy" refers to, for example, a straight-chain alkoxy having 1 to 24 carbon atoms or a branched-chain alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (branched-chain alkoxy having 3 to 5 carbon atoms) is particularly preferred.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

When describing the compound represented by formula (1), the term "substituted silyl" refers to a silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

"Trialkylsilyl" refers to a silyl group in which three hydrogen atoms are each independently substituted with an alkyl, and the alkyl can be any of the groups described above as the "alkyl" in the first substituent. Preferred alkyl groups for substitution are those having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

Specific trialkylsilyl groups include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyl Examples include methyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

"Tricycloalkylsilyl" refers to a silyl group in which three hydrogen atoms are each independently replaced with a cycloalkyl. Examples of this cycloalkyl include the groups described above as "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls, include silyl substituted with a group selected from the specific alkyls and cycloalkyls listed above.

Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the specific alkyls and aryls listed above. Specific examples of triarylsilyl include triphenylsilyl.

In the description of the compound represented by formula (1), the aryl in "diarylamino," the heteroaryl in "diheteroarylamino," the aryl and heteroaryl in "arylheteroarylamino," the aryl in "diarylboryl," and the aryl in "aryloxy" can be referenced from the above-mentioned descriptions of "aryl" and "heteroaryl."

The two aryls in the "diarylboryl" may be bonded via a single bond or a linking group (for example, >C(-R) ₂ , >O, >S, or >N-R). Here, R in >C(-R) ₂ and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and the first substituent may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). Specific examples of these groups include the above-mentioned descriptions of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, and aryloxy as the first substituent.

In the description of the compound represented by formula (1), when "aryl," "heteroaryl," "diarylamino," "diheteroarylamino," "arylheteroarylamino," "diarylboryl (two aryls may be bonded via a single bond or a linking group)," "alkyl," "cycloalkyl," "alkenyl," "alkoxy," "aryloxy," "substituted silyl," "alkylene," "arylene," and "heteroarylene" are described as "substituted or unsubstituted" or "optionally substituted," at least one hydrogen atom in the first substituent may be substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, cycloalkyl, and substituted silyl. For specific examples, see the descriptions of "aryl," "heteroaryl," "alkyl," "cycloalkyl," and "silyl" above. Additionally, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom is substituted with an aryl such as phenyl (specific examples include the groups listed above), an alkyl such as methyl or t-butyl (specific examples include the groups listed above), or a cycloalkyl such as cyclohexyl (specific examples include the groups listed above). For example, if the second substituent is carbazolyl, then the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

Examples of anthracene compounds represented by formula (1) include compounds represented by any of the following structural formulas. In the structural formulas below, "D" represents deuterium and "Me" represents methyl.

The anthracene compound represented by formula (1) can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions using starting materials such as a compound having a reactive group at a desired position in the anthracene moiety and a compound having a reactive group in a structure corresponding to the group represented by formula (1Sub). Alternatively, the anthracene compound represented by formula (1) may be produced by coupling a compound having a reactive group at a desired position in the anthracene moiety with a group corresponding to formula (A) in formula (1Sub) and then introducing a group corresponding to formula (Tph) having a reactive group. In this case, the compound having a reactive group corresponding to formula (A) may be a compound having two reactive groups for subsequent reaction with a compound having a reactive group corresponding to formula (Tph), or the reactive group may be subsequently introduced by a halogenation reaction or a C—H boronation reaction, or a functional group that can be converted to a reactive group, such as methoxy, may be introduced and then later converted to the reactive group (in the case of methoxy, the functional group may be demethylated to a hydroxyl group and then converted to a pseudohalogen group such as trifluoromethanesulfonate). Examples of the reactive group of these reactive compounds include halogens, pseudohalogen groups such as sulfonate esters (trifluoromethanesulfonate (TfO-) or tosylate (TsO-), or boronic acids, or tin compounds (having an R ₃ Sn- group or the like, where R is an alkyl or the like), zinc compounds (having an XZn- group or the like, where X is a halogen or the like), or Grignard reagents (having an XMg- group or the like, where X is a halogen or the like). As a specific production method, for example, the synthesis methods in paragraphs [0089] to [0175] of WO 2014/141725 can be referenced. Furthermore, the method described in the specification of U.S. Patent Application Publication No. 2015-001479 can be referenced.

Deuterated compounds can be synthesized in the same manner using the above method with starting materials containing deuterium. Alternatively, they can be synthesized by substituting deuterium for hydrogen in the compound using the method described in JP 2014-111561 A.

<<Organic Devices>>
The anthracene compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field-effect transistor, or an organic thin-film solar cell, and is preferably used as a material for an organic device for an organic electroluminescent device.

<Organic electroluminescent device>
The anthracene compound according to the present invention is preferably used as a material for forming an organic electroluminescent device. In particular, it is preferably used as a material for forming an emitting layer, and more preferably as a host material. Hereinafter, the organic electroluminescent device will be described in detail with reference to the drawings.

<Structure of Organic Electroluminescent Device>
FIG. 1 shows a schematic cross-sectional view of an example of an organic electroluminescent device.
The organic EL element 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

Not all of the above layers are essential; the minimum structural unit is the anode 102, light-emitting layer 105, and cathode 108, with the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 being optional layers. Furthermore, each of the above layers may consist of a single layer or multiple layers.

The layers constituting an organic EL element may be configured in the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode" configuration, as well as "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode," "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode," "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode," "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode," or "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport" configuration. The configurations may be "transport layer/cathode", "substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/light-emitting layer/electron transport layer/cathode", or "substrate/anode/light-emitting layer/electron injection layer/cathode".

<Light-emitting layer in organic electroluminescent device>
The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film and exhibits strong light-emitting (fluorescence) efficiency in a solid state. The light-emitting layer is preferably formed using a host material and a dopant material, and an anthracene compound represented by formula (1) is preferably used as the host material.

The light-emitting layer may be a single layer or multiple layers, each formed from light-emitting layer materials (host material, dopant material). The host material and dopant material may each be a single type or a combination of multiple types. When multiple host compounds are used in combination, at least one host compound must be an anthracene compound represented by formula (1). The dopant material may be contained entirely or partially in the host material. The multiple host materials or dopant materials may be contained in the light-emitting layer in a concentration gradient. As a doping method, the layer can be formed by co-evaporation with the host material, but it can also be mixed with the host material in advance and then vapor-deposited simultaneously (premix method). This premix method can also be applied to multiple combinations of multiple host materials, to which a dopant material may be added.

The amount of host material used varies depending on the type of host material and can be determined based on the properties of the host material. The amount of host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total light-emitting layer materials. The anthracene compound represented by formula (1) above is particularly preferred as the host material.

The amount of dopant material used varies depending on the type of dopant material and can be determined based on the characteristics of the dopant material. The recommended amount of dopant used is preferably 0.001 to 50% by mass of the total light-emitting layer material, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. The above ranges are preferable in that they can prevent concentration quenching, for example.

Host materials that can be used in combination with the anthracene compound represented by formula (1) include fused ring derivatives of anthracene and pyrene, which have long been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

Dopant materials are not particularly limited, and known compounds can be used. A variety of materials can be selected depending on the desired emission color. Specific examples include fused ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives (JP-A-1-245087), bisstyrylarylene derivatives (JP-A-2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, Examples include conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

Examples of dopant materials for each color of light emitted include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, as well as their derivatives, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine. Examples include aromatic heterocyclic compounds such as lysine and thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

Furthermore, examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene.Furthermore, suitable examples include compounds in which substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, have been introduced into the compounds exemplified above as blue to blue-green dopant materials.

Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes with ligands such as acetylacetone, benzoylacetone, and phenanthroline, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives.Further examples of suitable compounds include those obtained by introducing substituents such as aryl, heteroaryl, arylvinyl, amino, and cyano into the compounds exemplified above as blue to blue-green and green to yellow dopant materials, which enable longer wavelengths.

Other dopants can be appropriately selected from the compounds described in the June 2004 issue of Chemical Industry, page 13, and the references cited therein.

Among the dopant materials mentioned above, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

The amine having a stilbene structure is represented by, for example, the following formula:

In the formula, Ar ¹ is an m-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, but at least one of Ar ¹ to Ar ³ has a stilbene structure, Ar ¹ to Ar ³ may be substituted, and m is an integer of 1 to 4.

The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula:

In the formula, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ may be substituted.

Specific examples of aryls having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, stilbene, distyrylbenzene, distyrylbiphenyl, and distyrylfluorene.

Specific examples of amines having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl. Examples include 4,4'-bis[4"-bis(diphenylamino)styryl]biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)biphenyl, and 4,4'-bis(9-phenyl-3-carbazovinylene)biphenyl.

Also, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may be used.

Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl).

Perylene derivatives described in JP-A Nos. 11-97178, 2000-133457, 2000-26324, 2001-267079, 2001-267078, 2001-267076, 2000-34234, 2001-267075, and 2001-217077 may also be used.

Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene.

Borane derivatives such as those described in International Publication No. 2000/40586 may also be used.

The aromatic amine derivative is represented by, for example, the following formula:

In the formula, Ar ⁴ is an m-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ are optionally substituted, and m is an integer of 1 to 4.

In particular, an aromatic amine derivative in which Ar ⁴ is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ may be substituted, and m is 2 is more preferred.

Specific examples of aryls having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, pentacene, and benzofluorene.

Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl-N,N'-di(p-tolyl)chrysene-6,1 2-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1,6-diamine. Examples include N,N'-diphenyl-N,N'-bis(4-phenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine.

Examples of anthracene compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10-diamine, and N,N'-di Phenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetramethyl N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene, and the like.

Examples of pyrene-based compounds include N,N,N,N-tetraphenyl-1,8-pyrene-1,6-diamine, N-biphenyl-4yl-N-biphenyl-1,8-pyrene-1,6-diamine, and N ¹ ,N ⁶ -diphenyl-N ¹ ,N ⁶ -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine.

Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl.

Aromatic amine derivatives such as those described in JP 2006-156888 A may also be used.

Examples of coumarin derivatives include coumarin-6 and coumarin-334.

Coumarin derivatives described in JP-A Nos. 2004-43646, 2001-76876, and 6-298758 may also be used.

Examples of pyran derivatives include DCM and DCJTB shown below.

In addition, pyran derivatives described in JP-A Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, and 2001-052869 may also be used.

Further preferred dopant compounds include polycyclic aromatic compounds represented by formula (D) or multimers of polycyclic aromatic compounds having multiple partial structures represented by formula (D), and polycyclic aromatic compounds represented by formula (D-B) or multimers of polycyclic aromatic compounds having multiple unit structures represented by formula (D-B). By using any of these compounds in combination with the anthracene compound of the present invention to form an emitting layer, an organic EL device can be provided that has a narrower half-width of the emission spectrum and improved color purity.

[Polycyclic aromatic compound represented by formula (D) or multimer of polycyclic aromatic compound having a plurality of partial structures represented by formula (D)]
The polycyclic aromatic compound represented by formula (D) or the polycyclic aromatic compound having a plurality of structures represented by the following formula (D) is preferably a polycyclic aromatic compound represented by the following formula (D-a), (D-b), (D-c), (D-d), (D-e), or (D-f) or a multimer thereof.

In each structural formula, "A" to "C" and "a" to "c" are symbols that indicate ring structures, such as rings, benzene rings, or five-membered rings.

In formula (D), ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be replaced with a substituent.

It is preferable that at least one of ring A, ring B, and ring C is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, it is more preferable that ring A, ring B, and ring C are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent, and it is even more preferable that ring A, ring B, and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

In this case, preferred substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl.

Substituents are particularly preferably substituted or unsubstituted alkyl (especially neopentyl) or cycloalkyl such as adamantyl. Tertiary alkyl (tR) is also preferred. This is because such bulky substituents increase the intermolecular distance, improving the luminescence quantum yield (PLQY). Substituted or unsubstituted diarylamino is also preferred as a substituent.

The tertiary alkyl is represented by the following formula (tR):

In formula (tR), R ^x , R ^y , and R ^z are each independently alkyl having 1 to 24 carbon atoms, any —CH ₂ — in the alkyl may be substituted with —O—, and the group represented by formula (tR) substitutes at least one hydrogen atom in the compound or structure represented by formula (D) at *.

The "alkyl having 1 to 24 carbon atoms" of R ^x , R ^y , and R ^z may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

The total number of carbon atoms of R ^x , R ^y and R ^z in formula (tR) of formula (D) is preferably 3 to 20 carbon atoms, particularly preferably 3 to 10 carbon atoms.

Specific examples of alkyl for R ^x , R ^y , and R ^z include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

Examples of groups represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl. Of these, t-butyl and t-amyl are preferred.

Other preferred examples of substituents on ring A, ring B, and ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). Examples of "diarylamino" include the groups described below as "first substituents." Examples of substitution of a group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with a group of formula (tR).

The aryl or heteroaryl ring in ring A, ring B, and ring C may have a 5- or 6-membered ring that shares a bond with the central fused bicyclic structure of formula (D) composed of B (boron), ^X1 , and ^X2 .

Here, the term "fused bicyclic structure" refers to a structure in which two saturated hydrocarbon rings containing B (boron), ^X1 , and ^X2 are fused together, as shown in the center of formula (D). The term "six-membered ring sharing a bond with the fused bicyclic structure" refers to a six-membered ring (e.g., a benzene ring) fused to the fused bicyclic structure. The term "an aryl ring or heteroaryl ring (which is ring A) has this six-membered ring" refers to either the six-membered ring alone forming ring A, or the six-membered ring being further fused to another ring to form ring A. In other words, the term "an aryl ring or heteroaryl ring (which is ring A) having a six-membered ring" refers to the six-membered ring constituting all or part of ring A being fused to the fused bicyclic structure. The same explanation applies to "ring B,""ringC," and "five-membered ring."

Ring A in formula (D) corresponds to ring a and its substituents R 1 to R 3 in formulae (D-a), (D-b), (D-c), (D-d), (D-e), and (D-f). Ring B in formula (D) corresponds to ring b and its substituents R ⁸ to R ¹¹ in formulae (D-a), (D- ^b ), and (D-c), ring b and its substituents R ¹⁰ and R ¹¹ in formula (D- ^d ), and ring b and its substituents R ⁸ and R ⁹ in formulae (D-e) and (D-f). Ring C in formula (D) corresponds to ring c and its substituents R ⁴ to R ⁷ in formula (D-a), ring c and its substituents R ⁴ and R ⁵ in (D-b), formulae (D-d), and (D-f), and ring c and its substituents R ⁶ and R ⁷ in formulae (D-c) and (D-e). That is, formula (D-a) corresponds to a structure in which rings having at least a 6-membered ring structure are selected as rings A to C of formula (D), and formulas (D-b), (D-c), (D-d), (D-e), and (D-f) correspond to structures in which a ring having at least a 6-membered ring structure and a ring having at least a 5-membered ring structure are selected as rings A to C of formula (D), respectively. In this sense, each ring in formula (D-a) is represented by lowercase letters a to c.

X _X in formulae (D-b), (D-c), (D-d), (D-e), and (D-f) are each independently >O, >S, >N-R, or >C(-R) _2. Here, R in the >N-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, preferably a substituted or unsubstituted aryl, and more preferably an unsubstituted aryl. Furthermore, R in the >C(-R) ₂ are each independently hydrogen, an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl, preferably an alkyl, and more preferably a methyl. It is preferable that the two R in >C(-R) ₂ are the same. It is also preferable that the two R in >C(-R) ₂ are bonded to each other to form a ring.

In formulae (Da), (Db), (Dc), (Dd), (De), and (Df), R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

It is preferred that R ¹ to R ¹¹ are each independently hydrogen, alkyl (particularly the above-mentioned tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), substituted or unsubstituted diarylamino (bis(4-tertiarybutylphenyl)amino, bis(4-tertiaryamylphenyl)amino, bis(4-adamantylphenyl)amino, diphenylamino, etc.), or substituted silyl (triphenylsilyl, trimethylsilyl, etc.).

In formulae (D-a), (D-b), (D-c), (D-d), (D-e), and (D-f), it is preferred that 0 to 1 of R ¹ to R ³ are other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; 0 to 1 of R ⁴ to R ⁷ are other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; 0 to 1 of R ⁸ to R ¹ are other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; it is more preferred that 1 of R ¹ to R ³ is other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; 1 of R ⁴ to R ⁷ is other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen; and 1 of R ⁸ to R ¹ is other than hydrogen (particularly the preferred substituents described above) and the others are hydrogen.

In formulae (D-a), (D-b), (D-c), (D-d), (D-e), and (D-f), adjacent groups among the substituents R ¹ to R ¹¹ of ring a, ring b, and ring c may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Therefore, in the polycyclic aromatic compounds represented by formulas (D-a), (D-b), (D-c), (D-d), (D-e), and (D-f), the ring structures constituting the compounds change depending on the mutual bonding forms of the substituents in ring a, ring b, and ring c. For example, in the polycyclic aromatic compound represented by formula (D-a), the ring structures constituting the compound change, for example, as shown in the following formulas (D-a-1) and (D-a-2). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (D), respectively.

In the above formula (D-a-1) and formula (D-a-2), when explained in terms of formula (D-a), ring A', ring B', and ring C' represent aryl or heteroaryl rings formed together with ring a, ring b, and ring c by bonding adjacent groups among the substituents R ¹ to R ¹¹ (these may also be considered fused rings formed by fusing other ring structures to ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. Furthermore, as can be seen from the above formula (D-a-1) and formula (D-a-2), for example, R ⁸ of ring b and R ⁷ of ring c in formula (D-a), R ¹¹ of ring b and R ¹ of ring a, R ⁴ of ring c and R ³ of ring a, etc. do not fall under the category of "adjacent groups," and unless otherwise specified, they are not bonded to each other. That is, "adjacent groups" means groups adjacent to each other on the same ring.

The compounds represented by the above formula (D-a-1) and formula (D-a-2) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, indole ring, pyrrole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, cyclopentadiene ring, or indene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') formed is a naphthalene ring, carbazole ring, indole ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, indene ring, or fluorene ring, respectively.

Furthermore, for example, in formulae (D-b), (D-c), (D-d), (D-e), and (D-f), when X _X is >O, ring b or ring c is a furan ring, and the ring corresponding to ring B' or ring C' in formula (D-a-1) formed by condensing a benzene ring to this furan ring is a benzofuran ring.

Furthermore, for example, in formulae (D-b), (D-c), (D-d), (D-e), and (D-f), when X _X is >S, ring b or ring c is a thiophene ring, and the ring corresponding to ring B' or ring C' in formula (D-a-1) formed by condensing a benzene ring to this thiophene ring is a benzothiophene ring.

^X1 and ^X2 in formula (D) are each independently >O, >C(—R) ₂ , or >N—R. Preferably, at least one of ^X1 and ^X2 in formula (D) is >N—R, more preferably, both are >N—R, or one of ^X1 and ^X2 is >N—R and the other is >C(—R) ₂ , and most preferably, both are >N—R.

Each R in >C(-R) ₂ in ^X1 and ^X2 is independently an aryl substituted or unsubstituted with alkyl or cycloalkyl, a heteroaryl substituted or unsubstituted with alkyl or cycloalkyl, an alkyl, or a cycloalkyl. The two R in >C(-R) ₂ are preferably the same, and the two R may be bonded to form a ring. Examples of such compounds include the following compound (D-303).

R of >N-R in ^X1 and ^X2 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

R in >N-R in ^X1 and ^X2 is preferably an aryl having 6 to 12 carbon atoms substituted or unsubstituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or an alkyl having 1 to 6 carbon atoms, preferably an aryl having 6 to 12 carbon atoms substituted or unsubstituted with an alkyl having 1 to 5 carbon atoms, more preferably a phenyl substituted or unsubstituted with an alkyl having 1 to 6 carbon atoms, and even more preferably an ortho-biphenyl (phenyl having a phenyl at the ortho position relative to the N) substituted or unsubstituted with an alkyl having 1 to 6 carbon atoms. It is particularly preferable that only one of >N-R in ^X1 and ^X2 is an ortho-biphenyl substituted or unsubstituted with an alkyl having 1 to 6 carbon atoms. An example of such a compound is compound (D-202) shown below.

R in >N-R in ^X1 and ^X2 may be bonded to at least one of the rings A, B, and C via a linking group or a single bond. The linking group is preferably -O-, -S-, or -C(-R) ₂ -. R in the "-C(-R) ₂ -" is hydrogen, alkyl, or cycloalkyl. This definition can be expressed, for example, by a compound having a ring structure represented by the following formula (D-a-3-1) in which ^X1 and ^X2 are incorporated into fused ring B' and fused ring C'. That is, for example, it is a compound having ring B' (or ring C') formed by condensing another ring to the benzene ring, which is ring b (or ring c) in formula (D-a), so as to incorporate ^X1 (or ^X2 ). The fused ring B' (or fused ring C') thus formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

The above definition can also be expressed by compounds having a ring structure in which ^X1 and/or ^X2 are incorporated into a fused ring A', as represented by the following formula (D-a-3-2) or formula (D-a-3-3). That is, for example, it is a compound having a ring A' formed by condensing another ring to a benzene ring, which is ring a in formula (D-a), so as to incorporate ^X1 (and/or ^X2 ). The fused ring A' thus formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

Ring B and ring C in formula (D), or ring b and ring c in formula (D-a), may be bonded by a linking group represented by Xz or a single bond. Examples of such a form include forms such as those of formula (D-a-7-1) or formula (D-a-7-2). The linking group is preferably -O-, -S- or -C(-R) ₂ -. In addition, R in the above "-C(-R) ₂ -" is hydrogen, alkyl, or cycloalkyl, and the two Rs may form a ring.

The "aryl ring" represented by ring A, ring B, and ring C in formula (D) can be, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

Specific examples of "aryl rings" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic perylene ring and a pentacene ring.

Examples of the "heteroaryl ring" which is ring A, ring B, and ring C in formula (D) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen. This "heteroaryl ring" corresponds to a 5-membered ring containing X _X in formulae (D-b), (D-c), (D-d), (D-e), and (D-f), or a "heteroaryl ring formed together with ring a, ring b, or ring c by bonding adjacent groups among R ¹ to R ¹¹ " defined in formulae (D-a), (D-b), (D-c), (D-d), (D-e), and (D-f), and since ring a (or ring b, ring c) is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the fused rings to which the 5-membered ring is fused is 6, which is the lower limit of the carbon number.

Specific examples of "heteroaryl rings" include pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, cinnoline rings, and quinazo Examples include a phosphorus ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole ring, and naphthobenzofuran ring.

At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be replaced with a first substituent, which is a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "arylheteroarylamino," a substituted or unsubstituted "diarylboryl (the two aryls may be bonded via a single bond or a linking group)," a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," or a substituted "silyl." Examples of the first substituents include the monovalent groups of the "aryl ring" or "heteroaryl" described above, the aryl of the "arylamino," the heteroaryl of the "diheteroarylamino," the aryl and heteroaryl of the "arylheteroarylamino," the aryl of the "diarylboryl," and the aryl of the "aryloxy." For specific examples, please refer to the descriptions of "aryl" and "heteroaryl" in the explanation of formula (1).

The "alkyl" as the first substituent may be either linear or branched, and examples include linear alkyls having 1 to 24 carbon atoms or branched alkyls having 3 to 24 carbon atoms. Alkyls having 1 to 18 carbon atoms (branched alkyls having 3 to 18 carbon atoms) are preferred, alkyls having 1 to 12 carbon atoms (branched alkyls having 3 to 12 carbon atoms) are more preferred, alkyls having 1 to 8 carbon atoms (branched alkyls having 3 to 8 carbon atoms) are even more preferred, alkyls having 1 to 6 carbon atoms (branched alkyls having 3 to 6 carbon atoms) are particularly preferred, and alkyls having 1 to 5 carbon atoms (branched alkyls having 3 to 5 carbon atoms) are most preferred.

Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, and t-octyl (1,1,3,3-tetramethylbutyl). ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

Furthermore, examples of "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Also, examples of "alkoxy" as the first substituent include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 5 carbon atoms (branched-chain alkoxy having 3 to 5 carbon atoms) is particularly preferred.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

Furthermore, examples of "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

"Trialkylsilyl" refers to a silyl group in which three hydrogen atoms are each independently substituted with an alkyl, and the alkyl can be any of the groups described above as the "alkyl" in the first substituent. Preferred alkyl groups for substitution are those having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

Specific trialkylsilyl groups include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyl Examples include methyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

"Tricycloalkylsilyl" refers to a group in which three hydrogen atoms in a silyl group are each independently replaced with a cycloalkyl group, and examples of this cycloalkyl include the groups described above as "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls, include silyl substituted with a group selected from the specific alkyls and cycloalkyls listed above.

Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the specific alkyls and aryls listed above. Specific examples of triarylsilyl include triphenylsilyl.

Furthermore, the "aryl" in the "diarylboryl" of the first substituent can be referenced from the above description of the aryl. Furthermore, the two aryls may be bonded via a single bond or a linking group (for example, >C(-R) ₂ , >O, >S, or >N-R). Here, R in >C(-R) ₂ and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and the first substituent may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). Specific examples of these groups can be referenced from the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

As explained above, at least one hydrogen atom in the first substituent, substituted or unsubstituted "aryl," substituted or unsubstituted "heteroaryl," substituted or unsubstituted "diarylamino," substituted or unsubstituted "diheteroarylamino," substituted or unsubstituted "arylheteroarylamino," substituted or unsubstituted "diarylboryl (the two aryls may be bonded via a single bond or a linking group)," substituted or unsubstituted "alkyl," substituted or unsubstituted "cycloalkyl," substituted or unsubstituted "alkoxy," substituted or unsubstituted "aryloxy," or substituted "silyl," may be substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, cycloalkyl, and substituted silyl. Specific examples of these groups can be found in the explanations of the monovalent groups of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as the first substituent. Additionally, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom is substituted with an aryl such as phenyl (specific examples include the groups listed above), an alkyl such as methyl or t-butyl (specific examples include the groups listed above), or a cycloalkyl such as cyclohexyl (specific examples include the groups listed above). For example, if the second substituent is carbazolyl, then the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. Groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, and 3,6-dimethylcarbazolyl. Preferred are 3,6-di-t-butylcarbazolyl and phenoxy, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the perspective of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl.

R of >N-R in ^X1 and ^X2 of formula (D) is an aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above (however, it is preferable that the aryl as R of >N-R in ^X1 and ^X2 is not substituted with amino). Examples of this aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In addition, preferred examples of the second substituent in this case include alkyl such as methyl, tertiary butyl, and amyl, and substituted silyl such as p-tertiary butylphenyl and trimethylsilyl. The substitution position of the alkyl is preferably the para position relative to the substitution position of the N. As R of >N-R in ^X1 and ^X2 , an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) which may be substituted by a second substituent, a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is particularly preferred.

This explanation also applies to ^X1 and ^X2 in formulae (Da), (Db), (Dc), (Dd), (De), and (Df).

In formula (D), R in >C(-R) ₂ in ^X1 and ^X2 is each independently hydrogen or an aryl, heteroaryl, alkyl, or cycloalkyl optionally substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. Particularly preferred are aryls having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyls having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). It is preferable that the two R in >C(-R) ₂ are the same, and the two R may be bonded to form a ring. It is particularly preferable that both R in >C(-R) ₂ are methyl.

This explanation also applies to ^X1 and ^X2 in formulae (Da), (Db), (Dc), (Dd), (De), and (Df).

In formula (D), examples of the linking group when R of >N-R in ^X1 and ^X2 bonds to at least one of ring A, ring B, and ring C include -O-, -S-, -C(-R) ₂ -, and a single bond, and among these, R of "-C(-R) ₂ -" is hydrogen, alkyl, or cycloalkyl, and examples of this alkyl or cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred.

This explanation also applies to ^X1 and ^X2 in formulae (Da), (Db), (Dc), (Dd), (De), and (Df).

The dopant material may be a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (D) (preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (D-a), (D-b), (D-c), (D-d), (D-e), or (D-f)). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in any form as long as it has a plurality of the above unit structures within a single compound. For example, in addition to a form in which a plurality of the above unit structures are linked via a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene (linked multimer), it may also be in a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c, etc.) contained in the above unit structure is bonded so as to be shared by a plurality of unit structures (ring-shared multimer), or in a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c, etc.) contained in the above unit structure is bonded so as to be fused to each other (ring-fused multimer), but ring-shared multimers and ring-fused multimers are preferred, and ring-shared multimers are more preferred.

Examples of such multimers include multimers of polycyclic aromatic compounds having multiple unit structures represented by formula (D-a), such as multimers represented by formula (D-a-4), (D-a-4-1), (D-a-4-2), (D-a-5-1) to (D-a-5-4), or (D-a-6). The multimer compound represented by formula (D-a-4) below is a multimer compound having multiple unit structures represented by formula (D-a) in a single compound, with the benzene ring (ring a) in formula (D-a) being shared. Furthermore, the multimer compound represented by formula (D-a-4-1) below is a multimer compound having two unit structures represented by formula (D-a) in a single compound, with the benzene ring (ring a) in formula (D-a) being shared. Furthermore, the polymeric compound represented by the following formula (D-a-4-2) is a polymeric compound having three unit structures represented by formula (D-a) in one compound, with the benzene ring that is ring a in formula (D-a) being shared. Furthermore, the polymeric compounds represented by the following formulas (D-a-5-1) to (D-a-5-4) are polymeric compounds having multiple unit structures represented by formula (D-a) in one compound, with the benzene ring that is ring b (or ring c) in formula (D-a) being shared. Furthermore, the polymeric compound represented by the following formula (D-a-6), when explained in terms of formula (D-a), is a polymeric compound having multiple unit structures represented by formula (D-a) in one compound, with the benzene ring that is ring b (or ring a, ring c) in a certain unit structure being fused with the benzene ring that is ring b (or ring a, ring c) in a certain unit structure.

The multimeric compound may be a multimer in which a multimerization form represented by formula (D-a-4), formula (D-a-4-1), or formula (D-a-4-2) is combined with a multimerization form represented by any one of formulas (D-a-5-1) to (D-a-5-4) or formula (D-a-6); a multimer in which a multimerization form represented by any one of formulas (D-a-5-1) to (D-a-5-4) is combined with a multimerization form represented by formula (D-a-6); or a multimer in which a multimerization form represented by formula (D-a-4), formula (D-a-4-1), or formula (D-a-4-2), a multimerization form represented by any one of formulas (D-a-5-1) to (D-a-5-4), and a multimerization form represented by formula (D-a-6).

Furthermore, all or a portion of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (D) and its multimer may be deuterium, cyano, or halogen. For example, in formula (D), hydrogen atoms in ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, and R (= alkyl, cycloalkyl, aryl) when ^X1 and ^X2 are >N-R or >C(-R) ₂ may be substituted with deuterium, cyano, or halogen. Among these, embodiments in which all or a portion of the hydrogen atoms in the aryl or heteroaryl are substituted with deuterium, cyano, or halogen are exemplified. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of the polycyclic aromatic compounds represented by formula (D) or formula (D-a), (D-b), (D-c), (D-d), (D-e), or (D-f) and their multimers may be condensed with at least one cycloalkane.

For example, at least one of the aryl and heteroaryl rings in the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in rings A to C, the aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, and ring c, and the aryl (similar to above) and heteroaryl (similar to above) as R in >N- _R which is X ¹ and X ² , and >C(-R) 2 may be fused with at least one cycloalkane.

Preferably, at least one of the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in rings A to C, the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on rings a to c, and the aryl (similar to above) and heteroaryl (similar to above) as R in >N-R and >C(-R) ₂ which are ^X1 and ^X2 , may be fused with at least one cycloalkane.

More preferably, at least one of the aryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in rings A to C, the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a, ring b, and ring c, and >N-R which is X ¹ and X ² , and the aryl (similar to above) as R in >C(-R) ₂ may be fused with at least one cycloalkane.

More preferably, at least one of the aryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl as the first substituent in rings A to C (aryl or the aryl moiety in diarylamino), the aryl as the first substituent on ring a, ring b, and ring c (similar to above), and >N-R which is X ¹ and X ² , and the aryl as R in >C(-R) ₂ (similar to above) may be fused with at least one cycloalkane.

Examples of "cycloalkanes" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted derivatives of these having 1 to 5 carbon atoms.

Among these, structures in which at least one hydrogen atom is substituted on the α-carbon atom of the cycloalkane (in a cycloalkyl fused to an aromatic ring or heteroaromatic ring, the carbon atom adjacent to the fused carbon atom) are preferred, structures in which two hydrogen atoms are substituted on the α-carbon atom are more preferred, and structures in which a total of four hydrogen atoms are substituted on the two α-carbon atoms are even more preferred. Examples of such substituents include alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents.

In particular, it is preferable that the aryl ring or heteroaryl ring has a structure in which a partial structure represented by formula (B10) or (B11) below is bonded to adjacent carbon atoms.

In formula (B10) and formula (B11), Me represents methyl. * represents a bonding position, and is bonded to two adjacent elements on the aryl ring or heteroaryl ring to which the group represented by formula (B10) or formula (B11) is bonded.
Examples of compounds having such structures include the following compounds:

The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. Fused cycloalkanes, as in formulas (Cy-1-4) and (Cy-2-4), may also be fused with each other. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

At least one -CH ₂ - in a cycloalkane may be replaced with -O-. For example, an example in which one or more -CH ₂ - in a cycloalkane fused to a benzene ring (phenyl) are replaced with -O- is shown below. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

At least one hydrogen atom in the cycloalkane may be substituted. Examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. For details, see the description of the first substituent above. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, it may be substituted in a manner that forms a spiro structure, an example of which is shown below.

Other examples of cycloalkane condensation include polycyclic aromatic compounds and multimers thereof represented by formula (D) or formula (D-a), (D-b), (D-c), (D-d), (D-e), or (D-f), such as >N-R, where R is an aryl fused with a cycloalkane, diarylamino fused with a cycloalkane (fused to the aryl moiety), carbazolyl fused with a cycloalkane (fused to the benzene ring moiety), or benzocarbazolyl fused with a cycloalkane (fused to the benzene ring moiety). Examples of "diarylamino" include the groups described above as the "first substituent."

Further, as more specific examples, there can be mentioned examples in which R2 in the polycyclic aromatic compounds and multimers thereof represented by formula (D) or formula (D-a), (D-b), (D- ^c ), (D-d), (D-e), or (D-f) is a diarylamino fused with a cycloalkane (fused to the aryl moiety) or a carbazolyl fused with a cycloalkane (fused to the benzene ring moiety).

Specific examples of polycyclic aromatic compounds represented by formula (D) include compounds represented by the following structural formula. In the structural formula below, "D" represents deuterium, "Me" represents methyl, "Et" represents ethyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "TMS" represents trimethylsilyl.

The polycyclic aromatic compound represented by formula (D) and its multimer can be produced by referring to the method described in JP 2018-043984 A.

[Polycyclic aromatic compound represented by formula (DB) or multimer of polycyclic aromatic compound having a plurality of unit structures represented by formula (DB)]
The polycyclic aromatic compound represented by formula (DB) can also be used as a dopant compound.

In formula (D-B), rings A1, A2, and A3 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring, but at least one of rings A1, A2, and A3 is an aryl ring or a heteroaryl ring. At least one of the aryl ring and heteroaryl ring may be fused with at least one cycloalkane.

For the aryl ring, heteroaryl ring, cycloalkane ring, and the substituents, if any, please refer to the respective descriptions in the description of formula (D).

As a dopant, a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (D-B) (preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formulas (D-B-A), (D-B-B), (D-B-C), (D-B-D), (D-B-E), and (D-B-F), as described below) may be used. The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures within a single compound. For example, in addition to a form in which a plurality of the above unit structures are linked via a linking group such as a single bond, alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene (linked multimer), it may also be in a form in which any ring (ring A1, ring A2, or ring A3) contained in the above unit structure is bonded so as to be shared by multiple unit structures (ring-shared multimer), or in a form in which any ring (ring A1, ring A2, or ring A3) contained in the above unit structure is bonded so as to be fused to each other (ring-fused multimer).

In formula (D-B-A), formula (D-B-B), formula (D-B-C), formula (D-B-D), formula (D-B-E), and formula (D-B-F), ring A4, ring A5, ring A6, ring A7, ring A8, ring A9, ring A10, ring A11, ring A12, ring A13, ring A14, ring A1 5, ring A16, ring A17, ring A18, ring A19, ring A20, ring A21, ring A23, ring A24, ring A25, ring A26, ring A27, ring A28, ring A30, ring A31, ring A32, ring A33, ring A34, ring A35, ring A36, ring A37, ring A38, ring A3 9, ring A40, ring A41, and ring A42 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring, but at least one ring in formula (DB-A), formula (DB-B), and formula (DB-C), at least one ring of ring A19, ring A20, and ring A21 in formula (DB-D), at least one ring of ring A23, ring A24, and ring A25 in formula (DB-D), ring A26, ring A27 in formula (DB-E), and at least one ring of ring A28, at least one ring of ring A30, ring A31 and ring A32 in formula (D-B-E), at least one ring of ring A33, ring A34 and ring A35 in formula (D-B-F), at least one ring of ring A37, ring A38 and ring A39 in formula (D-B-F), and at least one ring of ring A40, ring A41 and ring A42 in formula (D-B-F) are a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and ring A4, ring A5, ring A6, ring It is preferable that A7, ring A8, ring A9, ring A10, ring A11, ring A12, ring A13, ring A14, ring A15, ring A16, ring A17, ring A18, ring A19, ring A20, ring A21, ring A23, ring A24, ring A25, ring A26, ring A27, ring A28, ring A30, ring A31, ring A32, ring A33, ring A34, ring A35, ring A36, ring A37, ring A38, ring A39, ring A40, ring A41, and ring A42 are all substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings.

In formula (DB-A), formula (DB-B-B), formula (DB-B-C), formula (DB-B-D), formula (DB-B-E), and formula (DB-B-F), L ^a is each independently a single bond, an alkylene, an arylene substituted or unsubstituted with an alkyl or cycloalkyl, or a heteroarylene substituted or unsubstituted with an alkyl or cycloalkyl. "Alkylene,""arylene," and "heteroarylene" are divalent groups obtained by removing any hydrogen atom from the "alkyl,""aryl," and "heteroaryl" described in formula (D). Preferred alkylenes are methylene and ethylene, preferred arylenes are phenylene and naphthalene, and preferred heteroarylenes are dibenzofuranylene. Phenylene, naphthalene, and dibenzofuranylene are more preferably unsubstituted. Furthermore, L ^a is also preferably a single bond.

In formulae (DB-A), (DB-B), (DB-C), (DB-D), (DB-E), and (DB-F), the aryl ring is preferably an aryl ring having 6 to 50 carbon atoms, and a benzene ring or a naphthalene ring is preferred. Furthermore, the heteroaryl ring is preferably a heteroaryl ring having 5 to 50 carbon atoms, and a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is preferred.

In this case, preferred substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl. For details about these substituents, please refer to the descriptions of the respective substituents in formula (D).

In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structures of polycyclic aromatic compounds represented by formula (DB-A), formula (DB-B), formula (DB-C), formula (DB-D), formula (DB-E), and formula (DB-F) and their multimers may be condensed with at least one cycloalkane.

Examples of "cycloalkanes" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted derivatives of these having 1 to 5 carbon atoms.

Among these, structures in which at least one hydrogen atom is substituted on the α-carbon atom of the cycloalkane (in a cycloalkyl fused to an aromatic ring or heteroaromatic ring, the carbon atom adjacent to the fused carbon atom) are preferred, structures in which two hydrogen atoms are substituted on the α-carbon atom are more preferred, and structures in which a total of four hydrogen atoms are substituted on the two α-carbon atoms are even more preferred. Examples of such substituents include alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents.

Furthermore, as polycyclic aromatic compounds represented by formula (D-B), and multimers of polycyclic aromatic compounds having multiple unit structures represented by formula (D-B), forms such as those of the following formula (D-B-a1), (D-B-a), (D-B-b), (D-B-c), (D-B-d), (D-B-e), or (D-B-f) are also preferred.

In formula (D-B-a1), formula (D-B-a), formula (D-B-b), formula (D-B-c), formula (D-B-d), formula (D-B-e), and formula (D-B-f), L ^a is as defined above, each Z ^b is independently N or C-R ^{Z b} , R ^{Z b} of said C-R ^{Z b} is hydrogen or a substituent, and R ^{Z b} of two adjacent C-R ^{Z b} may be bonded to each other to form an aryl ring or a heteroaryl ring, and the formed ring may be substituted. Furthermore, Z ^b =Z ^b may each independently be >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >S, >CO, >SO, >SO ₂ , or >Se, and R in the >N-R, the >C(-R) ₂ , and the >Si(-R) ₂ each independently is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two R in the >C(-R) ₂ and the >Si(-R) ₂ may be bonded to each other to form a ring.

R ^Zb is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl. For these substituents, the description of each substituent in formula (D) can be referred to.

In formula (D-B-a1), formula (D-B-a), formula (D-B-b), formula (D-B-c), formula (D-B-d), formula (D-B-e), and formula (D-B-f), the hydrogen atoms of the aryl ring or heteroaryl ring formed by bonding the R ^Zb of two adjacent C-R ^Zb are preferably substituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl. For the second substituents for these first substituents, reference can be made to the respective descriptions in formula (D).

In addition, all or some of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (D-B) and its multimer may be deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine. It is also preferable that some of the hydrogen atoms are deuterium, and it is even more preferable that all of the hydrogen atoms are deuterium.

More specific examples of polycyclic aromatic compounds represented by formula (D-B) include compounds represented by the following structural formula. Note that "tBu" in the following structural formula represents t-butyl.

The polycyclic aromatic compound represented by formula (D-B) and its multimer can be produced by referring to the method described in WO 2018/186396.

<Substrate in Organic Electroluminescent Device>
The substrate 101 is a support for the organic EL element 100 and is typically made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and examples thereof include glass plates, metal plates, metal foils, plastic films, and plastic sheets. Glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass is used, and the thickness should be sufficient to maintain mechanical strength, e.g., 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because fewer ions are eluted from the glass. However, commercially available soda-lime glass coated with a barrier coating such as _SiO2 can also be used. Furthermore, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof, and it is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet with poor gas barrier properties is used as the substrate 101.

<Anode in Organic Electroluminescent Device>
The anode 102 serves to inject holes into the light-emitting layer 105. When the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

Materials for forming the anode 102 include inorganic and organic compounds. Inorganic compounds include, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and NESA glass. Organic compounds include, for example, polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. Other materials that can be appropriately selected from those used as anodes in organic EL elements can also be used.

The resistance of the transparent electrode is not limited as long as it can supply enough current to light the light-emitting element, but low resistance is desirable from the perspective of the power consumption of the light-emitting element. For example, an ITO substrate of 300 Ω/□ or less will function as an element electrode, but since substrates of around 10 Ω/□ are now available, it is particularly desirable to use a low resistance product of, for example, 100 to 5 Ω/□, preferably 50 to 5 Ω/□. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but it is usually between 50 and 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescent device>
The hole injection layer 103 serves to efficiently inject holes migrating from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection/transport material.

A hole injection/transport material must be able to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. It is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, it is preferable for the material to have a low ionization potential, high hole mobility, excellent stability, and a low tendency for impurities that can become traps to be generated during manufacturing and use.

As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N ⁴ ,N ^{4 '} -diphenyl-N ⁴ ,N ^{4 '} -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N ⁴ ,N ⁴ ,N ^4' ,N ^4' -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]- Examples of suitable polymers include triphenylamine derivatives such as 4-amine, starburst amine derivatives, stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferred, but any compound is usable as long as it can form a thin film necessary for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials consist of compounds with good electron-donating or electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204(1998) and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731(1998)). These generate so-called holes through an electron transfer process in an electron-donating base material (hole-transporting material). The conductivity of the base material varies significantly depending on the number and mobility of the holes. Known examples of matrix materials with hole-transporting properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), as well as certain metal phthalocyanines (e.g., zinc phthalocyanine (ZnPc)) (JP 2005-167175 A).

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer that is responsible for the injection and transport of electrons from the cathode. It is desirable for the electron injection/transport layer to have high electron injection efficiency and efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, and excellent stability, and to be less likely to generate impurities that act as traps during manufacture and use. However, when considering the balance between hole and electron transport, if a material's primary function is to efficiently block holes from the anode from flowing toward the cathode without recombining, then even if its electron transport capacity is not that high, it can still have the same effect of improving luminous efficiency as a material with high electron transport capacity. Therefore, the electron injection/transport layer in this embodiment may also function as a layer that can efficiently block the movement of holes.

The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layers and electron transport layers of organic EL devices.

Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused ring derivatives; and metal complexes having electron-accepting nitrogen. Specific examples include fused ring aromatic derivatives such as naphthalene and anthracene; styryl aromatic derivatives such as 4,4'-bis(diphenylethenyl)biphenyl; perinone derivatives; coumarin derivatives; naphthalimide derivatives; quinone derivatives such as anthraquinone and diphenoquinone; phosphorus oxide derivatives; arylnitrile derivatives; and indole derivatives. Metal complexes having electron-accepting nitrogen include, for example, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with other materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. , pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

Metal complexes having an electron-accepting nitrogen atom can also be used, such as quinolinol metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The above materials can be used alone or in combination with other materials.

Among the materials mentioned above, the borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes described in WO 2020/054676 are preferred.

<Reducing Substances>
The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. Various substances can be used as this reducing substance as long as they have a certain level of reducing ability. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV). Substances with a work function of 2.9 eV or less are particularly preferred. Among these, alkali metals K, Rb, or Cs are more preferred, with Rb or Cs being even more preferred, and Cs being the most preferred. These alkali metals have particularly high reducing power, and adding relatively small amounts to the materials forming the electron transport layer or electron injection layer can improve the luminance and extend the life of organic EL devices. Combinations of two or more of these alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exerted, and adding it to the material that forms the electron transport layer or electron injection layer can improve the luminance and extend the life of the organic EL element.

<Cathode in Organic Electroluminescent Device>
The cathode 108 serves to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

The material for the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same materials as those for the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride/aluminum alloys), are preferred. To increase electron injection efficiency and improve device performance, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low-work-function metals are effective. However, these low-work-function metals are generally unstable in air. To address this issue, a known method is to dope the organic layer with trace amounts of lithium, cesium, or magnesium to create a highly stable electrode. Other dopants that can be used include, but are not limited to, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide.

Furthermore, for electrode protection, preferred examples include laminating metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. There are no particular restrictions on the method for producing these electrodes, as long as electrical conductivity can be achieved, and methods such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating can be used.

<Binder that may be used in each layer>
The materials used for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can be used alone to form each layer, but they can also be dispersed as a polymer binder in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, or polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, or silicone resin.

<<Method for producing organic electroluminescent element>>
Each layer constituting an organic EL device can be formed by forming the materials constituting each layer into a thin film using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, inkjet printing, spin coating, casting, and coating. The thickness of each layer thus formed is not particularly limited and can be set appropriately depending on the properties of the material, but is typically in the range of 2 nm to 5,000 nm. The film thickness can typically be measured using a quartz crystal oscillator film thickness measuring device. When forming a thin film using a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, and other factors. The vapor deposition conditions are generally preferably set appropriately within the following range: boat heating temperature +50 to +400°C, vacuum level 10 ⁻⁶ to 10 ⁻³ Pa, vapor deposition rate 0.01 to 50 nm/sec, substrate temperature −150 to +300°C, and film thickness in the range of 2 nm to 5 μm.

Next, as an example of a method for fabricating an organic EL device, we will explain a method for fabricating an organic EL device consisting of an anode, hole injection layer, hole transport layer, emissive layer composed of a host material and a dopant material, electron transport layer, electron injection layer, and cathode. A thin film of anode material is formed on a suitable substrate by vapor deposition or other methods to form an anode, and then thin films of hole injection layer and hole transport layer are formed on the anode. A thin film of host material and dopant material is co-deposited on top of this to form an emissive layer. An electron transport layer and electron injection layer are then formed on top of this emissive layer, and a thin film of cathode material is then formed by vapor deposition or other methods to form the cathode, thereby obtaining the desired organic EL device. It should be noted that the above-described organic EL device can also be fabricated in the reverse order: cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode.

When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + polarity and the cathode to - polarity. When a voltage of approximately 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or AC current is applied. The AC waveform applied can be any waveform.

<<Application examples of organic electroluminescent devices>>
The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element.

Display devices or lighting devices equipped with organic EL elements can be manufactured by known methods, such as by connecting the organic EL elements of this embodiment to a known driving device, and can be driven appropriately using known driving methods such as DC driving, pulse driving, or AC driving.

Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP 10-335066 A, JP 2003-321546 A, and JP 2004-281086 A). Display methods include, for example, matrix and/or segment methods. Note that matrix display and segment display may coexist on the same panel.

In a matrix display, pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters and images are displayed as a collection of pixels. The shape and size of the pixels are determined by the application. For example, square pixels measuring 300 μm or less on a side are typically used to display images and characters on computers, monitors, and televisions, while large displays such as display panels use pixels measuring on the order of millimeters on a side. For monochrome displays, pixels of the same color are simply arranged, but for color displays, red, green, and blue pixels are displayed side by side. Typical types are the delta type and the stripe type. This matrix can be driven by either line-sequential driving or active matrix. Line-sequential driving has the advantage of being simpler in structure, but active matrix can sometimes be superior when considering operating characteristics, so it is necessary to choose the appropriate method depending on the application.

In the segment type, a pattern is formed to display predetermined information, and a specific area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

Examples of lighting devices include lighting devices for indoor lighting and backlights for liquid crystal display devices (see, for example, JP 2003-257621 A, JP 2003-277741 A, and JP 2004-119211 A). Backlights are primarily used to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio equipment, automotive panels, display boards, signs, and the like. In particular, backlights for liquid crystal display devices, particularly those used in personal computers where thinning is an issue, are difficult to achieve because conventional systems use fluorescent lamps and light guide plates. Therefore, backlights using the light-emitting elements of this embodiment are characterized by their thinness and light weight.

The present invention will be explained in more detail below using examples, but the present invention is not limited to these. First, a synthesis example of an anthracene compound will be described below.

Synthesis Example (A-1): Synthesis of Compound (1-1) Under a nitrogen atmosphere, 2-(6-chlorodibenzofuran)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (16.0 g), synthesized by a known method, was dissolved in toluene (300 ml), and 2-bromotriphenylene (13.6 g), potassium carbonate (18.4 g), tetrabutylammonium bromide (TBAB, 2.9 g), dichlorobis(triphenylphosphine)palladium(II) (1.6 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 2 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-A) (13.0 g).

Under a nitrogen atmosphere, intermediate (IA) (13.0 g) was dissolved in toluene (300 ml), and 10-phenylanthracene-9-boronic acid (10.8 g), potassium carbonate (12.6 g), tetrabutylammonium bromide (2.0 g), bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (Pd-132, 0.64 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-1) (12.5 g).
EI-MS: m/z=646.

The structure of the obtained compound (1-1) was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 9.06 (d, 1H), 8.92 (d, 1H), 8.82-8.79 (m, 1H), 8.77-8.72 (m, 3H), 8.06-8.03 (dd, 1H), 7.80-7.69 (m, 7H), 7.68-7.55 (m, 6H), 7.53-7.45 (m, 4H), 7.40 (dd, 1H) 7.37-7.28 (m, 5H).

Synthesis Example (A-2): Synthesis of Compound (1-2) Under a nitrogen atmosphere, intermediate (IA) (10.0 g) was dissolved in toluene (300 ml), and 9-biphenylanthracene-10-boronic acid (6.4 g), potassium carbonate (7.43 g), tetrabutylammonium bromide (1.18 g), Pd-132 (0.38 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-2) (7.3 g).
EI-MS: m/z=722.

Synthesis Example (A-3): Synthesis of Compound (1-3) Under a nitrogen atmosphere, 8-chloro-4-dibenzofuranboronic acid (17.0 g) synthesized by a known method was dissolved in toluene (300 ml), and 2-bromotriphenylene (13.6 g), potassium carbonate (18.0 g), tetrabutylammonium bromide (2.9 g), dichlorobis(triphenylphosphine)palladium(II) (1.3 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (IB) (12.3 g).

Under a nitrogen atmosphere, intermediate (IB) (12.3 g) was dissolved in toluene (400 ml), and 10-naphthylanthracene-9-boronic acid (10.2 g), potassium carbonate (12.4 g), tetrabutylammonium bromide (2.0 g), Pd-132 (0.67 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 2 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-3) (12.5 g).
EI-MS: m/z=696.

Synthesis Example (A-4): Synthesis of Compound (1-4) Under a nitrogen atmosphere, 9-biphenyl-10-anthraceneboronic acid (20.0 g) synthesized by a known method was dissolved in toluene (400 ml), and 1-bromo-7-chlorodibenzofuran (12.4 g), potassium carbonate (12.2 g), tetrabutylammonium bromide (0.12 g), dichlorobis(triphenylphosphine)palladium(II) (1.5 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (IC) (14.1 g).

Under a nitrogen atmosphere, intermediate (I-C) (14.1 g) was dissolved in cyclopentyl methyl ether (500 ml), and bis(pinacolato)diboron (3.9 g), potassium acetate (5.1 g), potassium carbonate (0.72 g), palladium acetate (0.29 g), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 1.1 g) were added. The mixture was then heated and stirred under reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-D) (11.3 g).

Under a nitrogen atmosphere, intermediate (ID) (11.3 g) was dissolved in toluene (500 ml), and 2-bromotriphenylene (5.6 g), potassium carbonate (5.0 g), dichlorobis(triphenylphosphine)palladium(II) (0.63 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 1.5 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-4) (12.5 g).
EI-MS: m/z=722.

Synthesis Example (A-5): Synthesis of Compound (1-5) Under a nitrogen atmosphere, 8-chloro-3-dibenzofuranboronic acid (34.0 g) synthesized by a known method was dissolved in toluene (500 ml), and 2-bromotriphenylene (27.2 g), potassium carbonate (36.0 g), tetrabutylammonium bromide (6.0 g), dichlorobis(triphenylphosphine)palladium(II) (2.6 g), and water (100 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-E) (24.0 g).

Under a nitrogen atmosphere, intermediate (I-E) (24.0 g) was dissolved in toluene (600 ml), and 10-orthobiphenylanthracene-9-boronic acid (25.1 g), potassium carbonate (15.5 g), tetrabutylammonium bromide (0.36 g), Pd-132 (2.0 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 2 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-5) (32.3 g).
EI-MS: m/z=722.

Synthesis Example (A-6): Synthesis of Compound (1-6) Compound (1-5) (1 g), 5% platinum-carbon (5% Pt/C, 600 mg), heavy water (D ₂ O, 80 ml), cyclohexane (cHex, 40 ml), and isopropyl alcohol (IPA, 10 ml) were placed in a flask under an argon atmosphere and heated at 100° C. After the reaction, water and chloroform were added for liquid separation and extraction, the organic layer was dried over magnesium sulfate and filtered, and the organic layer was concentrated, and the resulting crude product was recrystallized to obtain compound (1-6).
EI-MS: m/z=756.

Synthesis Example (A-7): Synthesis of Compound (1-7) Under a nitrogen atmosphere, 7-chloro-3-dibenzofuranboronic acid (17.0 g) was dissolved in toluene (500 ml), and 2-bromotriphenylene (13.6 g), potassium carbonate (18.0 g), tetrabutylammonium bromide (3.0 g), dichlorobis(triphenylphosphine)palladium(II) (1.3 g), and water (100 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (1-F) (11.0 g).

Under a nitrogen atmosphere, intermediate (1-F) (11.0 g) was dissolved in toluene (600 ml), and 10-orthobiphenylanthracene-9-boronic acid (12.5 g), potassium carbonate (8.0 g), tetrabutylammonium bromide (0.18 g), Pd-132 (1.0 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 2 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-7) (16.0 g).
EI-MS: m/z=722.

Synthesis Example (A-8): Synthesis of Compound (1-8) Under a nitrogen atmosphere, 1,8-dichloroanthracene (14.1 g) was dissolved in cyclopentyl methyl ether (CPME, 500 ml), and 1-dibenzofuranboronic acid (4.8 g), potassium carbonate (7.9 g), palladium acetate (0.38 g), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.5 g) were added thereto, followed by stirring under heating and reflux for 1 hour. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (IG) (11.9 g).

Under a nitrogen atmosphere, intermediate (I-G) (11.9 g) was dissolved in cyclopentyl methyl ether (500 ml), and phenylboronic acid (3.8 g), potassium carbonate (4.0 g), palladium acetate (0.19 g), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.8 g) were added. The mixture was then heated to reflux and stirred for 1 hour. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-H) (10.4 g).

Under a nitrogen atmosphere, intermediate (I-H) (10.4 g) was dissolved in tetrahydrofuran (300 ml), N-bromosuccinimide (4.4 g) was added, and the mixture was heated to 60°C and stirred for 1 hour. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-I) (12.3 g).

Under a nitrogen atmosphere, 7-chloro-3-dibenzofuranboronic acid (7.3 g) was dissolved in toluene (500 ml), and intermediate (I-I) (12.3 g), potassium carbonate (6.9 g), tetrabutylammonium bromide (0.16 g), dichlorobis(triphenylphosphine)palladium(II) (0.88 g), and water (100 ml) were added, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (1-J) (12.4 g).

Under a nitrogen atmosphere, intermediate (1-J) (12.4 g) was dissolved in toluene (500 ml), and triphenyleneboronic acid (10.9 g), potassium carbonate (5.5 g), Pd-132 (0.5 g), and water (50 ml) were added thereto, followed by stirring under heating and reflux for 2 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-8) (12.2 g).
EI-MS: m/z=812.

Synthesis Example (A-9): Synthesis of Compound (1-9) Under a nitrogen atmosphere, 2-bromo-8-(10-phenylanthracene-9-)dibenzothiophene (5.0 g) synthesized by a known method was dissolved in toluene (100 ml), and 2-triphenyleneboronic acid (3.2 g), potassium carbonate (2.8 g), tetrabutylammonium bromide (0.06 g), dichlorobis(triphenylphosphine)palladium(II) (0.3 g), and water (10 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain compound (1-9) (3.3 g).
EI-MS: m/z=662.

Synthesis Example (A-10): Synthesis of Compound (1-10) Under a nitrogen atmosphere, 9-(7-bromo-9,9-dimethylfluorene)-10-phenylanthracene (1.0 g) synthesized by a known method was dissolved in toluene (50 ml), and 2-triphenyleneboronic acid (0.7 g), potassium carbonate (0.6 g), tetrabutylammonium bromide (0.01 g), dichlorobis(triphenylphosphine)palladium(II) (0.08 g), and water (5 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain compound (1-10) (1.0 g).
EI-MS: m/z=672.

Synthesis Example (A-11): Synthesis of Compound (1-11) Under a nitrogen atmosphere, 7-chloro-9,9-dimethylfluoroboronic acid (5.7 g) was dissolved in toluene (300 ml), and 2-bromotriphenylene (4.5 g), potassium carbonate (6.0 g), tetrabutylammonium bromide (1.0 g), dichlorobis(triphenylphosphine)palladium(II) (0.4 g), and water (30 ml) were added thereto, followed by stirring under heating and reflux for 3 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (1-K) (9.0 g).

Under a nitrogen atmosphere, intermediate (1-K) (9.0 g) was dissolved in toluene (200 ml), and 10-orthobiphenylanthracene-9-boronic acid (8.9 g), potassium carbonate (5.5 g), tetrabutylammonium bromide (0.13 g), Pd-132 (0.65 g), and water (30 ml) were added thereto, followed by stirring under heating and reflux for 5 hours. After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) and purified by sublimation to obtain compound (1-11) (8.8 g).
EI-MS: m/z=748.

Synthesis Example (A-12): Synthesis of Compound (1-12) Compound (1-12) was obtained in the same manner as in Synthesis Example (A-1). EI-MS: m/z=646.

Synthesis Example (A-13): Synthesis of Compound (1-13) Compound (1-13) was obtained in the same manner as in Synthesis Example (A-1). EI-MS: m/z=662.

Synthesis Example (A-14): Synthesis of Compound (1-14) Compound (1-14) was obtained in the same manner as in Synthesis Example (A-1). EI-MS: m/z=688.

Synthesis Example (A-15): Synthesis of Compound (1-15) Compound (1-15) was obtained in the same manner as in Synthesis Example (A-1). EI-MS: m/z=646.

By appropriately changing the raw material compounds, other anthracene compounds of the present invention can be synthesized using methods similar to the above synthesis examples.

Synthesis Example (B1): Synthesis of Compound (D-114)

Under a nitrogen atmosphere, a flask containing methyl 4-methoxysalicylate (50.0 g) and pyridine (anhydrous, 350 ml) was cooled in an ice bath. Next, trifluoromethanesulfonic anhydride (154.9 g) was added dropwise to this solution. After the addition was complete, the ice bath was removed and the mixture was stirred at room temperature for 2 hours, after which water was added to quench the reaction. After adding toluene and separating the liquid, the mixture was purified using a silica gel short-path column (eluent: toluene) to obtain methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (86.0 g).

Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 2.5 g) was added to a suspension of methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (23.0 g), ( _4-( diphenylamino)phenyl)boronic acid (25.4 g), tripotassium phosphate ( _31.1 g), toluene (184 ml), ethanol (27.6 ml), and water (27.6 ml), and the mixture was stirred at reflux temperature for 3 hours. The reaction solution was cooled to room temperature, and water and toluene were added, followed by phase separation. The solvent in the organic layer was distilled off under reduced pressure. The resulting solid was purified using a silica gel column (eluent: heptane/toluene mixed solvent) to give methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (29.7 g). In this case, the ratio of toluene in the eluent was gradually increased to elute the target substance, with reference to the method described in "Guide to Organic Chemistry Experiments (1) - Methods for Handling Materials and Separation and Purification -" Kagaku Dojin Publishing, p. 94.

Under a nitrogen atmosphere, a tetrahydrofuran (THF, 111.4 ml) solution of methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (11.4 g) was cooled in a water bath, and a THF solution of methylmagnesium bromide (1.0 M, 295 ml) was added dropwise to the solution. After the dropwise addition was complete, the water bath was removed, the temperature was raised to reflux, and the mixture was stirred for 4 hours. The mixture was then cooled in an ice bath, and an aqueous ammonium chloride solution was added to terminate the reaction. Ethyl acetate was added to separate the mixture, and the solvent was then distilled off under reduced pressure. The resulting solid was purified using a silica gel column (eluent: toluene) to yield 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (8.3 g).

Under a nitrogen atmosphere, a flask containing 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (27.0 g), the catalyst TAYCACURE-15 (Teica Corporation, 13.5 g), and toluene (162 ml) was stirred at reflux temperature for 2 hours. The reaction mixture was cooled to room temperature and passed through a silica gel short-path column (eluent: toluene) to remove the TAYCACURE-15. The solvent was then distilled off under reduced pressure to yield 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.8 g).

Under a nitrogen atmosphere, a flask containing 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.0 g), pyridine hydrochloride (36.9 g), and N-methyl-2-pyrrolidone (NMP, 22.5 ml) was stirred at reflux temperature for 6 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added to separate the liquid. The solvent was removed under reduced pressure, and the mixture was purified using a silica gel column (eluent: toluene) to obtain 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (22.0 g).

Under a nitrogen atmosphere, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (14.1 g), 2-bromo-1,3-difluorobenzene (3.6 g), potassium carbonate (12.9 g), and NMP (30 ml) was heated and stirred at reflux for 5 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, water was added, and the resulting precipitate was collected by suction filtration. The resulting precipitate was washed with water and then methanol, and then purified using a silica gel column (eluent: heptane/toluene mixed solvent) to obtain 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (12.6 g). The ratio of toluene in the eluent was gradually increased to elute the target product.

Under a nitrogen atmosphere, a flask containing 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (11.0 g) and xylene (60.5 ml) was cooled to -40°C, and a 2.6 M n-butyllithium hexane solution (5.1 ml) was added dropwise. After the addition was complete, the mixture was stirred at -40°C for 0.5 hours, then heated to 60°C and stirred for 3 hours. The reaction mixture was then depressurized to remove low-boiling components, cooled to -40°C, and boron tribromide (4.3 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours, then cooled to 0°C, and N-ethyl-N-isopropylpropan-2-amine (3.8 g) was added. The mixture was then heated and stirred at 125°C for 8 hours. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution was added to terminate the reaction. Toluene was then added to separate the mixture. The organic layer was purified using a silica gel short-path column, then a silica gel column (eluent: a mixed solution of heptane/toluene = 4/1 (volume ratio)), and then an activated carbon column (eluent: toluene) to obtain compound (D-114) (1.2 g).

The structure of the obtained compound (D-114) was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ=8.64 (s, 2H), 7.75 (m, 3H), 7.69 (d, 2H), 7.30 (t, 8H), 7.25 (s, 2H), 7.20 (m, 10H), 7.08 (m, 6H), 1.58 (s, 12H).

Synthesis Example (B2): Synthesis of Compound (D-52)

Under a nitrogen atmosphere, 3-bromo-N,N-diphenylaniline (35 g), 4-t-butylaniline (19.3 g), dichlorobis[(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 76 mg) as a palladium catalyst, sodium t-butoxide (NaOtBu, 15.6 g), and xylene (200 ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction was complete, water and ethyl acetate were added to the reaction solution and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene/heptane = 1/1 (volume ratio)) to obtain intermediate (I-1) (40 g).

Under a nitrogen atmosphere, intermediate (I-1) (10.0 g), intermediate (I-2) (12.3 g), Pd-132 (0.2 g) as a palladium catalyst, NaOtBu (3.7 g), and xylene (60 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene/heptane = 1/4 (volume ratio)) to obtain intermediate (I-3) (18.5 g).

A 1.56 M tert-butyllithium pentane solution (50.1 ml) was added to a flask containing intermediate (I-3) (15.0 g) and tert-butylbenzene (100 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 70°C and stirred for 0.5 hours, after which components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (19.1 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (9.9 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, after which the mixture was heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and the mixture was separated. The organic layer was concentrated and purified using a silica gel short column (eluent: chlorobenzene). The resulting crude product was recrystallized from toluene to obtain compound (D-52) (9.6 g).

EI-MS: m/z=812.

Synthesis Example (B3): Synthesis of Compound (D-7)

Compound (D-7) was synthesized using the same method as in Synthesis Example (B2).

The structure of the obtained compound (D-7) was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ=1.47 (s, 36H), 2.17 (s, 3H), 5.97 (s, 2H), 6.68 (d, 2H), 7.28 (d, 4H), 7.49 (dd, 2H), 7.67 (d, 4H), 8.97 (d, 2H).

Synthesis Example (B4): Synthesis of Compound (D-69)

Compound (D-69) was synthesized using a method similar to that used in Synthesis Example (B2).

The structure of the obtained compound (D-69) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.20 (s, 9H), 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.18 (s, 3H), 5.97 (s, 1H), 6.08 (d, 1H), 6.63 (d, 1H), 6.66 (d, 1H), 7.20 (d, 2H), 7.27 (d, 2H), 7.32 (dd, 1H), 7.48 (dd, 1H), 7.61 (t, 1H), 7.67 (d, 2H), 8.84 (d, 1H), 8.94 (d, 1H).

Synthesis Example (B5): Synthesis of Compound (D-202)

Compound (D-202) was synthesized using the same method as in Synthesis Example (B2).

The structure of the obtained compound (D-202) was confirmed by NMR measurement.
¹ H-NMR: δ = 1.1 (s, 9H), 1.4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (s, 3H), 5.9 (s, 1H), 6.1 (s, 1H), 6.7 (m, 2H), 7 .0 (d, 2H), 7.1 (d, 2H), 7.2 (d, 1H), 7.3 (m, 2H), 7.4 (m, 1H), 7.5 (m, 1H), 7.6 (dd, 1H), 7.7 (m, 3H), 8.9 (d, 1H), 8.9 (d, 1H).

Synthesis Example (B6): Synthesis of Compound (D-215)

Compound (D-215) was synthesized using the same method as in Synthesis Example (B2).

The structure of the obtained compound (D-215) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ=1.21 (s, 18H), 1.36 (s, 36H), 1.48-1.66 (m, 12H), 1.89 (s, 3H), 6.18 (s, 2H), 6.78 (s, 2H), 7.22 (d, 4H), 7.25-7.28 (m, 2H), 7.59 (t, 2H), 8.86 (d, 2H).

Synthesis Example (B7): Synthesis of Compound (D-201)

Compound (D-201) was synthesized using the same method as in Synthesis Example (B2).

The structure of the obtained compound (D-201) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 0.62 (t, 6H), 0.75 (t, 6H), 1.29 (s, 12H), 1.43 (s, 12H), 1.62 (q, 4H), 1.75 (q, 4H), 5.63 (s, 2 H), 6.70 (d, 2H), 6.86 (m, 2H), 6.92 (d, 4H), 7.05 (m, 4H), 7.14 (d, 4H), 7.38 (m, 6H), 8.85 (d, 2H).

Synthesis Example (B8): Synthesis of Compound (D-270)

Compound (D-270) was synthesized using a method similar to that used in Synthesis Example (B2).

The structure of the obtained compound (D-270) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ=1.32 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H).

Synthesis Example (B9): Synthesis of Compound (D-206)

Compound (D-206) was synthesized using the same method as in Synthesis Example (B2).

The structure of the obtained compound (D-206) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.08 (s, 6H), 1.27 (s, 6H), 1.42 (s, 6H), 1.46 (s, 9H), 1.47 (s, 9H), 1.48 (s, 6H), 1.69-1.81 (m, 8H), 2.18 (s, 3H), 5.97 (s, 1H), 6.06 (s, 1H), 6.52 (s, 1H), 6.67 (d, 1H), 7.08 (dd, 1H), 7.25-7.29 (m, 3H), 7.48 (dd, 1H), 7.59 (d, 1H), 7.67 (d, 2H), 8.89 (s, 1H), 8.97 (d, 1H).

Synthesis Example (B10): Synthesis of Compound (D-18)

A flask containing intermediate (I-4) (15 g) and toluene (300 ml) was heated to 70°C under a nitrogen atmosphere to completely dissolve intermediate (I-4). After cooling the flask to -20°C, tetramethylethylenediamine (TMEDA, 20.8 g) and a 1.00 M solution of sec-butyllithium in cyclohexane and n-hexane (89 ml) were added. The temperature was raised to 0°C and the mixture was stirred for 3 hours. After that, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (33.3 g) was added and the mixture was refluxed for 1 hour. Water and toluene were added, and the mixture was separated. The organic layer was evaporated under reduced pressure. The resulting solid was washed with Solmix A-11 (trade name: Nippon Alcohol Sales Co., Ltd.), dissolved in toluene, and left to stand at 0°C for 1 hour. The precipitate was filtered off, and the filtrate was passed through a silica gel column (eluent: toluene/heptane = 1/5 mixed solvent (volume ratio)). After distilling off the solvent, reprecipitation was performed with a mixed solvent of ethyl acetate and Solmix A-11 to obtain intermediate (I-5) (9.5 g) as a white solid.

A flask containing intermediate (I-5) (8.7 g), aluminum chloride (12.5 g), N,N-diisopropylethylamine (DIPEA, 6.0 g), and chlorobenzene (44 ml) was stirred at 120°C for 1 hour under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into ice water (200 ml), and toluene was added to extract the organic layer. The solvent in the organic layer was evaporated under reduced pressure, and the resulting solid was dissolved in chloroform and passed through a silica gel short-path column (eluent: toluene). The crude product obtained by evaporation of the solvent under reduced pressure was reprecipitated using cyclopentyl methyl ether and Solmix A-11 to obtain compound (D-18) (6.2 g, yield 70%) as a yellow solid.

The structure of the obtained compound (D-18) was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 8.95 (d, 2H), 7.45 (dd, 6H), 7.13 (d, 4H), 7.08-7.04 (m, 4H), 6.95-6.88 (m, 6H), 6.75 (d, 2H), 5.56 (s, 2H), 1.46 (s, 18H), 1.33 (s, 18H).

Synthesis Example (B11): Synthesis of Compound (D-155)

Under a nitrogen atmosphere, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (9.0 g), 1,2-dibromo-3-fluorobenzene (7.9 g), potassium carbonate (8.2 g), and NMP (45 ml) was heated and stirred at reflux for 2 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, water was added, and the resulting precipitate was collected by suction filtration. The resulting precipitate was washed with water and then with Solmix, and then purified using a silica gel column (eluent: heptane/toluene = 3/1 (volume ratio)) to obtain 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (12.4 g, yield: 84.8%).

Under a nitrogen atmosphere, a flask containing 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (10.0 g), di([1,1'-biphenyl]-4-yl)amine (5.3 g), palladium acetate (0.15 g), dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphane (0.61 g), NaOtBu (2.4 g), and toluene (35 ml) was heated at 80°C for 6 hours. After the reaction mixture was cooled to room temperature, water and toluene were added and the mixture was separated. Further purification using a silica gel column (eluent: heptane/toluene = 2/1 (volume ratio)) yielded 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (7.4 g, yield: 53.1%).

Under a nitrogen atmosphere, 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (7.9 g) and THF (42 ml) were placed in a flask and cooled to -40°C, and 1.6 M n-butyllithium hexane solution (6 ml) was added dropwise. After the addition was complete, the mixture was stirred at this temperature for 1 hour, and then trimethyl borate (1.7 g) was added. The mixture was warmed to room temperature and stirred for 2 hours. Water (100 ml) was then slowly added dropwise. Next, the reaction mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then the drying agent was removed to obtain dimethyl(2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronate (7.0 g, yield: 100%).

Under a nitrogen atmosphere, dimethyl(2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronate (6.5 g), aluminum chloride (10.3 g), and toluene (39 ml) were placed in a flask and stirred for 3 minutes. N-ethyl-N-isopropylpropan-2-amine (2.5 g) was then added, and the mixture was heated and stirred at 105°C for 1 hour. After heating, the reaction mixture was cooled and ice water (20 ml) was added. The reaction mixture was then extracted with toluene, and the organic layer was purified using a silica gel short-path column (eluent: toluene) and then a silica gel column (eluent: heptane/toluene = 3/1 (volume ratio)). The extract was then reprecipitated with heptane and further purified using an NH2 silica gel column (eluent: heptane/toluene = 1/1 (volume ratio)). Finally, the product was purified by sublimation to obtain compound (D-155) (0.74 g, yield: 12.3%).

The structure of the obtained compound (D-155) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 9.22 (s, 1H), 8.78 (s, 1H), 7.96 (d, 2H), 7.80 to 7.77 (m, 6H), 7.71 (d, 1H), 7.59 to 7.44 (m, 8H), 7.39 (t, 1H) ), 7.32 to 7.29 (m, 4H), 7.71 (d, 1H), 7.19 (dd, 4H), 7.12 to 7.06 (m, 4H), 7.00 (d, 1H), 6.45 (d, 1H), 1.57 (s, 6H).

Synthesis Example (B12): Synthesis of Compound (D-249)

Compound (D-249) was synthesized using a method similar to that used in Synthesis Example (B2).

EI-MS: m/z=756.

Synthesis Example (B13): Synthesis of Compound (D-255)

Compound (D-255) was synthesized using the same method as in Synthesis Example (B2).

EI-MS: m/z=811.

Synthesis Example (B14): Synthesis of Compound (D-253)

Compound (D-253) was synthesized using the same method as in Synthesis Example (B2).

EI-MS: m/z=889.

Synthesis Example (B15): Synthesis of Compound (D-254)

Compound (D-254) was synthesized using the same method as in Synthesis Example (B2).

EI-MS: m/z=867.

Synthesis Example (B16): Synthesis of Compound (D-264)

Compound (D-264) was synthesized using the same method as in Synthesis Example (B2).

EI-MS: m/z=944.

Synthesis Example (B17): Synthesis of Compound (D-293)

Tri-p-tolylamine (0.287 g, 1.00 mmol), boron triiodide (0.783 g, 2.00 mmol), and o-dichlorobenzene (10.0 mL) were heated and stirred at 150°C for 2 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and 2-isopropenylphenylmagnesium bromide (5.25 mL, 1.2 M, 6.30 mmol) was added. The mixture was then filtered using a Florisil short-path column (eluent: toluene), and the solvent was removed under reduced pressure. The resulting crude product was isolated and purified by washing with hexane, yielding 0.309 g of 2,8-dimethyl-10-(2-(prop-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborine in a 75% yield.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 2.05 (s, 3H), 2.31 (s, 6H), 2.54 (s, 3H), 4.78 (s, 2H), 6.74 (d, 2H) 7.20-7.28 (m, 4H), 7.37-7.48 (m, 5H), 7.56 (d, 1H), 7.68 (s, 2H).
^13C -NMR ( _CDCl3 ): δ = 20.6 (s, 2C), 21.3 (s, 1C), 23.8 (s, 1C), 116.7 (s, 2C), 116.9 (s, 1C), 126.0 (d, 2C), 126.8 (s, 1C), 128.2 (s, 2C), 130.0 (d, 4C), 131.4 (d, 4C), 133.0 (s, 1C), 133.7 (s, 2C), 136.4 (s, 2C), 138.6 (s, 1C), 139.3 (s, 1C), 145.1 (s, 1C), 147.0 (d, 2C).

2,8-Dimethyl-10-(2-(prop-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborine (82.2 mg, 0.20 mmol), scandium trifluoromethanesulfonate (0.100 g, 0.20 mmol), and 1,2-dichloroethane (55.0 mL) were heated and stirred at 95°C for 24 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered using a Florisil short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The resulting crude product was isolated and purified using a silica gel column (eluent: hexane/toluene = 6/1 (volume ratio)), yielding 32.0 mg of compound (D-293) in a 39% yield.

The structure of the obtained compound (D-293) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.98 (s, 6H), 2.48 (s, 3H), 2.53 (s, 3H), 2.76 (s, 3H), 6.61 (d, 1H), 6.75 (d, 1H), 7.1 4-7.31 (m, 4H), 7.40-7.47 (m, 3H), 7.57 (dt, 1H), 7.81 (d, 1H), 8.44 (d, 1H), 8.50 (s, 1H).
^13C -NMR ( _CDCl3 ): δ = 20.9 (s, 1C), 21.4 (s, 1C), 24.3 (s, 1C), 32.6 (s, 2C), 43.5 (s, 1C), 114.0 (s, 1C), 116.6 (s, 1C), 124.7 (s, 1C), 125.8 (s, 1C), 127.0 (s, 1C), 128.4 (s, 2C), 130.1 (s, 2C), 130.5 (s, 1C), 131.4 (s, 2C), 133.0 (s, 1C), 135.2 (s, 1C), 135.5 (s, 1C), 137.7 (s, 1C), 138.4 (s, 1C), 139.5 (s, 1C), 144.3 (s, 1C), 145.4 (s, 1C), 151.4 (s, 1C), 159.5 (s, 1C).

Compound (DB-2) was synthesized by the method described in WO 2018/186396.

By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized using methods similar to the synthesis examples described above.

Next, to further explain the present invention, examples of organic EL devices using the compounds of the present invention are shown, but the present invention is not limited to these.

<Evaluation of vapor-deposited organic EL elements>
The organic EL elements of Examples 1 to 42 and Comparative Examples 1 to 4 were prepared, and the characteristics at 1000 cd/ ^m² of light emission, such as driving voltage (V), external quantum efficiency (%), and the time during which 90% or more of the initial luminance was maintained (element lifetime), were measured.

The quantum efficiency of light-emitting elements can be divided into internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the rate at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element. Since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected within the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring external quantum efficiency is as follows. Using an Advantest voltage/current generator R6144, a voltage was applied to make the element emit light at a luminance of 1000 cd/ ^m² . Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region was measured from a direction perpendicular to the light-emitting surface. Assuming that the light-emitting surface is a perfectly diffusing surface, the measured spectral radiance value of each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Next, the number of photons was integrated over the entire observed wavelength range to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary charge was taken as the number of carriers injected into the element, and the value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element was the external quantum efficiency.

<Examples 1 to 16 and Comparative Example 1>
The layer structures of the organic EL devices produced in Examples 1 to 16 and Comparative Example 1 are shown in Table 1.

The chemical structure of the materials used for each layer in the fabricated organic EL device and the comparative compound (1) used in Comparative Example 1 are shown below.

Example 1
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Nagasu Sangyo Co., Ltd.), and tantalum vapor deposition boats containing HI, HAT-CN, HT-1, HT-2, compound (1-1), compound (D-255), ET-1, and ET-2, and aluminum nitride vapor deposition boats containing Liq, magnesium, and silver, respectively, were attached.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 ⁻⁴ Pa, and first, HI was heated and vapor-deposited to a thickness of 40 nm to form hole injection layer 1. Next, HAT-CN was heated and vapor-deposited to a thickness of 5 nm to form hole injection layer 2. Next, HT-1 was heated and vapor-deposited to a thickness of 45 nm to form hole transport layer 1. Next, HT-2 was heated and vapor-deposited to a thickness of 10 nm to form hole transport layer 2. Next, compound (1-1) as the host and compound (D-255) as the dopant were simultaneously heated and vapor-deposited to a thickness of 25 nm to form an emitting layer. The vapor deposition rate was adjusted so that the mass ratio of compound (1-1) to compound (D-255) was approximately 98:2. Next, ET-1 was heated and vapor-deposited to a thickness of 5 nm to form electron transport layer 1. Next, ET-2 and Liq were heated simultaneously and evaporated to a thickness of 25 nm to form an electron transport layer 2. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The evaporation rate for each layer was 0.01 to 1 nm/sec. Liq was then heated and evaporated at an evaporation rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm. Next, magnesium and silver were heated simultaneously and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. The evaporation rate was adjusted between 0.1 and 10 nm/sec so that the atomic ratio of magnesium to silver was 10:1.

<Examples 2 to 12 and Comparative Example 1>
The host and dopant in Example 1 were changed to the combinations shown in Table 1 to prepare the devices of Examples 2 to 16 and Comparative Example 1.

When a direct current voltage was applied between the ITO electrode as the anode and the magnesium/silver electrode as the cathode, and the characteristics at 1000 cd/m ² luminescence were measured, blue luminescence was obtained. The results are shown in Table 2.
It is being formed.

As mentioned above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices and shown to be excellent materials. However, other compounds that have not been evaluated also have the same basic skeleton and have a similar overall structure, and those skilled in the art will understand that they are similarly excellent materials for organic EL devices.

According to a preferred embodiment of the present invention, an organic EL device is produced that includes an emitting layer containing an anthracene compound of a specific structure together with a polycyclic aromatic compound, thereby providing an organic EL device that has excellent driving voltage and quantum efficiency, particularly excellent quantum efficiency.

REFERENCE SIGNS LIST 100 Organic electroluminescent element 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (10)

An anthracene compound represented by the following formula (1A) or (1C) :
In each of formulas (1A) and (1C),
R ¹ , R ⁸ and R ⁹ each independently represent an aryl having 6 to 30 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms which may be substituted with an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 15 carbon atoms;
R ² , R ³ , R ⁶ , and R ⁷ each independently represent hydrogen or alkyl having 1 to 24 carbon atoms;
One of any two ^Z1's is a carbon bonded to Tph and the other is a carbon bonded to L, and Tph is a group represented by formula (Tph),
Other Z1 ^'s are each C—H,
^X1 and ^X2 each independently represent a single bond, >O, >S, >N-R, or >C(-R) ₂ , and R in the >N-R and >C(-R) ₂ each independently represents a substituted or unsubstituted aryl or a substituted or unsubstituted alkyl ;
L is bonded to any Z1 ^;
L is a single bond, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;
In the formula (Tph),
Any one of ^Z2 is a carbon bonded to ^Z1 , which is also a carbon;
Other Z2 ^'s are each independently CH;
At least one hydrogen atom in the compounds represented by formula (1A) and formula (1C) may be substituted with a substituted silyl, cyano, halogen, or deuterium. 2. The anthracene compound according to claim 1, wherein L is a single bond. R ¹ , R ⁸ , and R ⁹ are each independently phenyl, naphthyl, biphenylyl, terphenyl, dibenzofuranyl, benzonaphthofuranyl, phenyl-substituted naphthyl, or naphthyl-substituted phenyl ;
3. The anthracene compound according to claim 1, wherein ^R2 , ^R3 , ^R6 , and ^R7 are each hydrogen . The anthracene compound according to any one of claims 1 to 3, represented by formula (1A): The anthracene compound according to any one of claims 1 to 3, represented by formula (1C): 2. The anthracene compound according to claim 1 , which is represented by any one of the following structural formulas:
An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains the anthracene compound according to any one of claims 1 to 6 . The organic electroluminescent device according to claim 7 , wherein the light-emitting layer further comprises a polycyclic aromatic compound represented by the following formula (D) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (D):
In formula (D),
Ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted;
^X1 and ^X2 are each independently >O, >C(-R) ₂ , or >N-R, R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >N-R may be bonded to at least one ring of the ring A, the ring B, and the ring C by a linking group or a single bond, R of the >C(-R) ₂ are each independently an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl, and two R in the >C(-R) ₂ may be bonded to each other to form a ring;
In the compound represented by formula (D) or a multimer thereof, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one —CH ₂ — in the cycloalkane may be substituted with —O—;
In the compound represented by formula (D) or a multimer thereof, ring B and ring C may be bonded via a single bond or —O—, —S—, or —C(—R) ₂ —, where R in —C(—R) ₂ — is hydrogen, alkyl, or cycloalkyl, and the two Rs may be bonded to each other to form a ring; and
At least one hydrogen atom in the compound represented by formula (D) or a polymer thereof may be substituted with cyano, halogen or deuterium. The organic electroluminescent device according to claim 7, wherein the light-emitting layer further contains a polycyclic aromatic compound represented by the following formula (D-B) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (D-B):
In formula (D-B),
Ring A1, ring A2, and ring A3 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring, provided that at least one of ring A1, ring A2, and ring A3 is an aryl ring or a heteroaryl ring;
At least one selected from the group consisting of aryl rings and heteroaryl rings may be fused with at least one cycloalkane;
At least one hydrogen atom in the compound represented by formula (DB) or a polymer thereof may be substituted with cyano, halogen or deuterium. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 7 to 9 .