JP7236896B2 - Method for producing condensed ring compound - Google Patents

Description

TECHNICAL FIELD The present invention relates to a method for producing a condensed ring compound.

Condensed ring compounds such as dibenzo[g,p]chrysene compounds are sometimes used as materials for organic electroluminescence devices. However, practical production methods for the condensed ring compound are limited.

Non-Patent Documents 1 to 3 describe production of condensed ring compounds using oxidizing agents such as ferric chloride (FeCl ₃ ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and orthochloranil. discloses a method.

Journal of the American Chemical Society 2019, 141, p3-10 Organic. Letters, 2011, Vol. 13, No. 7, p1634-1637 Angew. Chem. Int. Ed. 2017, 56, p.12224-12228

One aspect of the present invention is directed to providing a method for producing a condensed ring compound in a simpler process without using an oxidizing agent.

The present inventor conducted further research on methods for producing condensed ring compounds such as the above dibenzo[g,p]chrysene compounds. As a result, the methods for producing condensed ring compounds disclosed in Non-Patent Documents 1 to 3 use a large amount of an oxidizing agent that is unstable in the atmosphere for the reaction substrate, resulting in poor handling properties and the use of the oxidizing agent. In addition to requiring post-treatment, it was found that there is a possibility of causing corrosion deterioration of equipment.
As a result of intensive research, the present inventors have found that a compound having a predetermined structure (a compound represented by the formula (1) and a compound represented by the formula (2) described later) is used as a reaction substrate, and in the presence of a catalyst and a base, The present inventors have completed the present invention by discovering that the compound represented by formula (3), which is a condensed ring compound, can be obtained by the reaction.

式中、
Ｘ^１～Ｘ^４は、それぞれ独立に、置換基を有していてもよい、炭素（Ｃ）原子、酸素（Ｏ）原子および硫黄（Ｓ）原子からなる群より選択される１種以上の原子から構成されている単環、二縮環又は三縮環の芳香環を表し；
Ｚ^１およびＺ^２は、それぞれ独立に、臭素原子、又はヨウ素原子を表す。 A manufacturing method according to one aspect of the present invention is as follows.
A method for producing a condensed ring compound represented by formula (3),
A production method comprising reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a catalyst and a base:

During the ceremony,
X ¹ to X ⁴ are each independently one or more atoms selected from the group consisting of a carbon (C) atom, an oxygen (O) atom and a sulfur (S) atom, which may have a substituent Represents a monocyclic, dicondensed or tricondensed aromatic ring consisting of;
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom.

According to one aspect of the present invention, it is possible to provide a method for producing a condensed ring compound in a simpler process without using an oxidizing agent.

In attempting to synthesize the compound represented by formula (3), the present inventor conducted further research on Non-Patent Documents 1 to 3, and obtained the following knowledge.
In the methods for producing condensed ring compounds according to Non-Patent Documents 1 to 3, ferric chloride (FeCl ₃ ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), oxidizing agents such as orthochloranil is manufactured using However, since these oxidizing agents are often unstable in the air, they are difficult to handle and complicated to control for safe reaction during use. In addition, it has been found that the production methods according to Non-Patent Documents 1 to 3 are not preferable in large-scale production, because it is necessary to use a large excess of oxidizing agent with respect to the reaction substrate. Furthermore, in the production method according to Non-Patent Document 1, 5 equivalents or more of the oxidizing agent is used with respect to the substrate, which leads to high costs and requires post-treatment of the oxidizing agent.

The inventors of the present invention have conducted further research and studies to solve the above-described problems, and as a result, have found that the problems caused by the oxidizing agent can be solved by using a specific reaction substrate.
The production method according to one embodiment of the present invention uses a diaryl compound having a specific structure and an alkyne compound having a specific structure as reaction substrates, whereby the process of formula (3) can be performed in a simpler process without using an oxidizing agent. ) can be prepared.
Therefore, the production method according to one aspect of the present invention can safely control the reaction more easily than conventional production methods that require the use of an oxidizing agent, and can be applied to the production of various condensed ring compounds.
Moreover, in the case of the conventional production method using an oxidizing agent, a two-stage reaction process of synthesizing a cyclization precursor and carrying out a cyclization reaction using the cyclization precursor is essential. In contrast, according to the production method according to one aspect of the present invention, the synthesis of the cyclization precursor and the subsequent cyclization reaction can be performed in one pot, and the condensed ring compound of formula (3) can be obtained. can be done. Therefore, a very simplified process can be realized.
Furthermore, according to the manufacturing method according to one aspect of the present invention, since it is not necessary to use a large amount of oxidizing agent, costs can be reduced.
In addition, according to the production method according to one aspect of the present invention, the fused ring compound of formula (3) can be obtained at a higher yield than conventional production methods.

Hereinafter, the method for producing a condensed ring compound according to one embodiment of the present invention will be described in more detail.

<Method for producing condensed ring compound>
A production method according to one aspect of the present invention comprises:
A method for producing a condensed ring compound represented by formula (3),
comprising reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a catalyst and a base:

During the ceremony,
X ¹ to X ⁴ are each independently one or more atoms selected from the group consisting of a carbon (C) atom, an oxygen (O) atom and a sulfur (S) atom, which may have a substituent Represents a monocyclic, dicondensed or tricondensed aromatic ring consisting of;
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom.

Definitions of symbols in formulas (1) to (3) are as follows.
<About X ¹ to X ⁴ >
Each of X ¹ to X ⁴ independently represents a monocyclic, dicondensed or tricondensed aromatic ring optionally having a substituent. The monocyclic, dicondensed or tricondensed aromatic ring is composed of one or more atoms selected from the group consisting of carbon (C) atoms, oxygen (O) atoms and sulfur (S) atoms. .
If X ¹ to X ⁴ are these aromatic rings, it is assumed that it would be extremely difficult to control the cyclization reaction by a conventional method using an oxidizing agent. However, in the production method according to this embodiment, even when X ¹ to X ⁴ are these aromatic rings, the cyclization reaction can be well controlled and the desired condensed ring compound can be obtained in a higher yield.
For the same reason, in each aromatic ring represented by X ¹ to X ⁴ which are monocyclic, dicondensed ring or tricondensed aromatic rings, the oxygen (O) atom constituting the aromatic ring The sum of the number and the number of sulfur (S) atoms is preferably 0 or more and 2 or less, and each aromatic ring represented by X ¹ to X ⁴ is composed only of carbon (C) atoms. is more preferably a monocyclic, bicondensed or tricondensed aromatic ring. Furthermore, for the same reason, X ¹ to X ⁴ are each independently preferably a benzene ring, naphthalene ring or phenanthrene ring which may have a substituent.

Furthermore, from the viewpoint of availability of raw materials, X ¹ and X ² represent ^a monocyclic aromatic ring optionally having a substituent ^; It is preferably a bi- or tri-condensed aromatic ring which may be substituted, and the other is preferably a monocyclic aromatic ring which may have a substituent.

Furthermore, X ¹ and X ² are preferably the same aromatic ring. When X ¹ and X ² are the same aromatic ring, the formation of isomers during the formation of phenanthrene by the reaction of the compound represented by formula (1) with the compound represented by formula (2) can be reduced. can. That is, since the compound represented by formula (1) is symmetrical across the single bond connecting ^X1 and ^X2 , the desired condensed ring compound can be obtained in a higher yield than in the asymmetrical case. Obtainable.

The substituents that the monocyclic, bicondensed, or tricondensed aromatic rings X ¹ to X ⁴ may have are not particularly limited. groups, activating groups, labeling groups, and the like. Among these substituents, a charge-transporting group is preferable because a condensed ring compound useful as an organic conductive material can be produced.

<Regarding the charge-transporting group>
A charge-transporting group is a substituent having a function of transporting charge. A charge is a hole, an electron, or both.
Examples of the charge-transporting group include substituents represented by (a-1) to (a-17) below.
(a-1) a deuterium atom,
(a-2) a fluorine atom, a chlorine atom,
(a-3) a trifluoromethyl group,
(a-4) a pentafluoroethyl group,
(a-5) a cyano group,
(a-6) a nitro group,
(a-7) a hydroxyl group,
(a-8) a thiol group,
(a-9) an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms,
(a-10) an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms,
(a-11) a phosphine oxide group optionally having a substituent,
(a-12) a silyl group optionally having a substituent,
(a-13) a boronyl group optionally having a saturated hydrocarbon group having 2 to 10 carbon atoms as a substituent;
(a-14) a linear or branched alkyl group having 1 to 18 carbon atoms,
(a-15) a linear or branched alkoxy group having 1 to 18 carbon atoms, or
(a-16) a group represented by formula (4), or (a-17) a group represented by (4′):

In formula (4),
R ¹ and R ² each independently
(r-1) a hydrogen atom,
(r-2) a deuterium atom,
(r-3) a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent;
(r-4) an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms, or
(r-5) represents a linear or branched alkyl group having 1 to 18 carbon atoms;
L is
a phenylene group optionally substituted with a methyl group or a phenyl group;
a naphthylene group optionally substituted with a methyl group or a phenyl group,
a biphenylene group optionally substituted with a methyl group or a phenyl group, or
representing a single bond;
n represents 1 or 2,
if L is a single bond, n is 1;
n is 1 or 2 when L is not a single bond.
When n is 2, a plurality of R ¹ to R ² may be the same or different.
In formula (4′),
R ¹ to R ³ are each independently
(r-1) a hydrogen atom,
(r-2) a deuterium atom,
(r-3) a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent;
(r-4) an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms, or
(r-5) represents a linear or branched alkyl group having 1 to 18 carbon atoms;
L is
a phenylene group optionally substituted with a methyl group or a phenyl group;
a naphthylene group optionally substituted with a methyl group or a phenyl group,
a biphenylene group optionally substituted with a methyl group or a phenyl group, or
represents a single bond.

<About (a-9)>
Examples of monocyclic, linked or condensed aromatic hydrocarbon groups having 6 to 30 carbon atoms related to (a-9) include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group and anthryl group. , phenanthryl group, benzofluorenyl group, triphenylenyl group, spirobifluorenyl group, diphenylfluorenyl group, dibenzo[g,p]chrysenyl group and the like. The monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms is preferably a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms.

The aromatic hydrocarbon group of (a-9) may have a substituent, and the substituents are each independently a fluorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group, and a thiol. a phosphine oxide group optionally having a substituent, a silyl group optionally having a substituent, a boronyl group optionally having a saturated hydrocarbon group having 2 to 10 carbon atoms as a substituent, A linear or branched alkyl group having 1 to 18 carbon atoms or a linear or branched alkoxy group having 1 to 18 carbon atoms is preferable.

The phosphine oxide group which may have a substituent includes an unsubstituted phosphine oxide group and a phosphine oxide group having a substituent. Among these, a phosphine oxide group having a substituent is preferred.
The phosphine oxide group having a substituent is preferably a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms, or a phosphine oxide group having a condensed heteroaromatic group as a substituent. . Specific examples include phosphine oxide groups substituted with two aryl groups, such as diphenylphosphine oxide.

Examples of the silyl group which may have a substituent include an unsubstituted silyl group and a silyl group having a substituent. Among these, a silyl group having a substituent is preferred.
The silyl group having a substituent is preferably a silyl group having a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms, or a condensed heteroaromatic group as a substituent. Specific examples include a silyl group substituted with three aryl groups, such as a triphenylsilyl group.

Examples of the boronyl group optionally having a saturated hydrocarbon group having 2 to 10 carbon atoms as a substituent include a dihydroxyboryl group (-B(OH) ₂ ), 4,4,5,5-tetramethyl- [1,3,2]-Dioxaborolanyl group, 5,5-dimethyl-[1,3,2]-Dioxaborinane group and the like.

Linear or branched alkyl groups having 1 to 18 carbon atoms include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, n-hexyl group, cyclohexyl group, octyl group, decyl group, dodecyl group, octadecyl group and the like.

Linear or branched alkoxy groups having 1 to 18 carbon atoms include, for example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyl oxy group, n-hexyloxy group, cyclohexyloxy group, octyloxy group, decyloxy group, dodecyloxy group, octadecyloxy group and the like.

<About (a-10)>
The monocyclic, linked, or condensed heteroaromatic group having 3 to 36 carbon atoms related to (a-10) has at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom. It is a monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms contained on the ring. Examples of the heteroaromatic group include pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, phenylpyridyl group, pyridylphenyl group and pyrimidyl group. , pyrazyl group, 1,3,5-triazyl group, 1,3,5-triazylphenyl group, 1,3,5-triazylbiphenylyl group, 4,6-diphenyl-1,3,5-triazyl group , indolyl group, benzothienyl group, benzofuranyl group, benzimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group , 2,1,3-benzoxadiazolyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, carbazolyl group, 9-phenylcarbazolyl group, 9-(4-biphenylyl)carbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, phenazine group, thianthrenyl group and the like.

The heteroaromatic group of (a-10) may have a substituent, and each of the substituents is independently a cyano group, a fluorine atom, a trifluoromethyl group, a straight chain having 1 to 18 carbon atoms, or A branched alkyl group or a linear or branched alkoxy group having 1 to 18 carbon atoms is preferred. Examples of the linear or branched alkyl group having 1 to 18 carbon atoms include the same linear or branched alkyl groups having 1 to 18 carbon atoms exemplified in (a-9) above. Examples of the linear or branched alkoxy group having 1 to 18 carbon atoms include the same linear or branched alkoxy groups having 1 to 18 carbon atoms exemplified in (a-9) above.

<About (a-11)>
The optionally substituted phosphine oxide group (a-11) includes an unsubstituted phosphine oxide group and a substituted phosphine oxide group. Among these, a phosphine oxide group having a substituent is preferred.
Examples of the phosphine oxide group having a substituent include the same phosphine oxide groups having a substituent exemplified in (a-9) above.

<About (a-12)>
Examples of the optionally substituted silyl group (a-12) include an unsubstituted silyl group and a substituted silyl group. Among these, a silyl group having a substituent is preferred.
Examples of the substituted silyl group include the same substituted silyl groups as exemplified in (a-9) above.

<About (a-13)>
The boronyl group optionally having a saturated hydrocarbon group having 2 to 10 carbon atoms as a substituent, which is (a-13), includes, for example, and the same as the boronyl group having a saturated hydrocarbon group as a substituent.

<About (a-14)>
Examples of the linear or branched alkyl group having 1 to 18 carbon atoms include the same linear or branched alkyl groups having 1 to 18 carbon atoms as exemplified in (a-9) above.

<About (a-15)>
Examples of straight or branched alkoxy groups having 1 to 18 carbon atoms include the same straight or branched alkoxy groups having 1 to 18 carbon atoms exemplified in (a-9) above.

<About (a-16)>
As described above, the substituents X ¹ to X ⁴ may have may be groups represented by the above formula (4). In formula (4), the definitions of L, R ¹ , R ² and n are as follows.

In formula (4), R ¹ and R ² are each independently (r-1) a hydrogen atom, (r-2) a deuterium atom, (r-3) an optionally substituted carbon 6 to 30 monocyclic, linked or condensed aromatic hydrocarbon group, (r-4) optionally substituted monocyclic, linked or condensed hetero ring having 3 to 36 carbon atoms (r-5) represents an aromatic group or a linear or branched alkyl group having 1 to 18 carbon atoms.
When R ¹ and R ² have substituents, R ¹ and R ² may be substituted with one substituent or may be substituted with two or more substituents.

The definition of the optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms (r-3) is the above except for the definition of the substituent. It is the same as the definition of the monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms described in (a-9).
When the aromatic hydrocarbon group (r-3) has a substituent, the substituent may be a deuterium atom, a fluorine atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or A linear or branched alkoxy group, 9-carbazolyl group, dibenzothienyl group, dibenzofuranyl group, N,N-diphenylamino group, or N,N-bis(4-biphenylyl)-amino group is preferable. .

The linear or branched alkyl group having 1 to 18 carbon atoms is the same as the linear or branched alkyl group having 1 to 18 carbon atoms exemplified in (a-9) above.
Examples of the linear or branched alkoxy group having 1 to 18 carbon atoms include the same linear or branched alkoxy groups having 1 to 18 carbon atoms exemplified in (a-9) above.

The definitions of the optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms (r-4) are as described above, except for the definitions of the substituents. Examples thereof include the same monocyclic, linked or condensed heteroaromatic groups having 3 to 36 carbon atoms as exemplified in (a-10). More preferably, it is a monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms.
When the heteroaromatic group (r-4) has a substituent, the substituent may be a deuterium atom, a fluorine atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or 1 to 18 carbon atoms. A linear or branched alkoxy group, 9-carbazolyl group, dibenzothienyl group, dibenzofuranyl group, N,N-diphenylamino group, or N,N-bis(4-biphenylyl)-amino group preferable. These substituents have, for example, the same definition as the aforementioned substituent (r-3).

The definition of the linear or branched alkyl group having 1 to 18 carbon atoms, which is (r-5) above, is the same as the definition shown in (a-9) above.

In formula (4), L is a phenylene group optionally substituted by a methyl group or a phenyl group; a naphthylene group optionally substituted by a methyl group or a phenyl group; a good biphenylene group; or represents a single bond.
Examples of the phenylene group include 1,2-phenylene group, 1,3-phenylene group and 1,4-phenylene group.
Examples of the naphthylene group include naphthalene-1,2-diyl group, naphthalene-1,4-diyl group, naphthalene-1,8-diyl group and naphthalene-2,3-diyl group.
Examples of the biphenylene group include biphenyl-4,4'-diyl group, biphenyl-4,3'-diyl group, biphenyl-4,2'-diyl group, biphenyl-3,3'-diyl group, biphenyl- 3,2'-diyl group, biphenyl-2,2'-diyl group and the like.

In formula (4), n represents an integer of 1 or 2. When L is a single bond, n is an integer of 1; n is an integer of 1 or 2 when L is not a single bond.
In addition, when n is 2, there are two each of R ¹ and R ² , which may be the same or different.

<About (a-17)>
As described above, the substituents X ¹ to X ⁴ may have may be groups represented by the above formula (4′).
In formula (4′), L, R ¹ , and R ² can be the same as defined in formula (4). In formula (4′), R ³ can have the same definition as R ¹ explained in formula (4).

<Preferred reaction>
As the reaction of the present embodiment described above, a reaction represented by any one of formulas (5) to (11) is preferable. Non-Patent Document 3 discloses a method for producing a condensed ring compound using an oxidizing agent. However, under oxidizing conditions, sterically hindered carbon atoms (also called fjord-regions) in the backbone form additional cyclization reactions with surrounding neighboring carbon atoms, thus controlling the cyclization stepwise. is difficult. In addition, since intermolecular oxidative coupling also proceeds, multimers having the desired backbone are easily replicated. Therefore, the compounds obtained by the reactions of formulas (5) to (11) are particularly difficult to synthesize by conventional methods. According to one aspect of the present invention, compounds obtained by the reactions of formulas (5) to (11), which are difficult to synthesize under such conventional conditions, can be obtained more easily, which is preferable.

In formula (5),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁴ each independently represent a charge-transporting group;
k1 to k4 are each an integer of 0 to 4:
When the sum of k1 to k4 is an integer of 2 or more, multiple A ¹ to A ⁴ may be the same or different.
In each of formulas (6) to (10),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁵ each independently represent a charge-transporting group;
k1 to k4 are each independently an integer of 0 to 4;
k5 is an integer between 0 and 2:
The sum of k1 to k5 may be an integer of 2 or more, and when the sum of k1 to k5 is an integer of 2 or more, a plurality of A ¹ to A ⁵ may be the same or different.
In formula (11),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁴ and A ⁶ each independently represent a charge-transporting group;
k1 to k4 and k6 are each independently an integer of 0 to 4;
When the sum of k1 to k4 and k6 is an integer of 2 or more, multiple A ¹ to A ⁴ and A ⁶ may be the same or different.

<About k1 to k6>
k1 to k4 and k6 are each independently an integer of 0 or more and 4 or less. k5 is an integer of 0 or more and 2 or less.
It should be noted that k1 to k4 in formula (5), k1 to k5 in formulas (6) to (10), k1 to k4, and k6 in formula (11), if the sum of each is an integer of 2 or more, the formula A ¹ to A ⁴ in (5), A ¹ to A 5 in formulas (6) to (10) ^, and A ¹ to A ⁴ and A ⁶ in formula (11) are plural. For example, if the sum of k1 to k4 (the sum of k1+k2+k3+k4) in equation (5) is 2, any two of A ¹ to A ⁴ are present in equation (5). When such multiple substituents are present, they may be the same or different.
In terms of availability of raw materials, the sum of k1 to k4 in formula (5), the sum of k1 to k5 in each of formulas (6) to (10), the sum of k1 to k4 in formula (11), and k6 are preferably 4 or less, more preferably 2 or less, and particularly preferably 0 or 1.

Each of k1, k2 and k5 is preferably 0 or 1, more preferably 0, from the viewpoint of obtaining a condensed ring compound in a higher yield.
k3, k4 and k6 are preferably 0, 1 or 2, more preferably 0 or 1, in terms of raw material availability.

^{<About A 1 to A 6>}
Groups represented by A ¹ to A ⁶ each independently represent a charge-transporting group. The definition of the groups represented by A ¹ to A ⁶ is the same as the charge-transporting group that may be possessed by the monocyclic, bicondensed ring, or tricondensed aromatic ring in formulas (1) to (3). and the same applies to the preferred range.
When A ¹ to A ⁶ are groups having substituents, A ¹ to A ⁶ may be substituted with one substituent or may be substituted with two or more substituents.
When the charge-transporting group in A ¹ to A ⁶ is a group that may have a substituent, the definition of the substituent is the same as defined in formulas (1) to (3). For example, A ¹ to A ⁶ are monocyclic, linked or condensed aromatic hydrocarbon groups having 6 to 30 carbon atoms having substituents, or monocyclic or linked monocyclic having 3 to 36 carbon atoms having substituents. , or in the case of a condensed heteroaromatic group, the substituents are each independently the same as those exemplified in (a-9) above.

Specific examples of A ¹ to A ⁶ are preferably groups (1) to (24) shown below.

(1): methyl group, ethyl group, fluorine atom, chlorine atom, cyano group, nitro group, hydroxyl group, thiol group, deuterium atom

(2): phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3 ,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 3,4,5 - trimethylphenyl group

(3): 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 2-methyl-1,1'-biphenyl-4-yl group, 3-methyl-1,1'-biphenyl-4-yl group , 2′-methyl-1,1′-biphenyl-4-yl group, 3′-methyl-1,1′-biphenyl-4-yl group, 4′-methyl-1,1′-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1' -biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'-biphenyl-4-yl group, 2',3 '-dimethyl-1,1'-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2',5'-dimethyl-1,1'-biphenyl -4-yl group, 2',6'-dimethyl-1,1'-biphenyl-4-yl group, 4-phenylbiphenyl group, 2-phenylbiphenyl group

(4): 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalene-1-yl group, 4-methylnaphthalen-1-yl group, 6-methylnaphthalene-2-yl group, 4-(1-naphthyl ) phenyl group, 4-(2-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 3-methyl-4-(1-naphthyl)phenyl group, 3- methyl-4-(2-naphthyl)phenyl group, 4-(2-methylnaphthalen-1-yl)phenyl group, 3-(2-methylnaphthalen-1-yl)phenyl group, 4-phenylnaphthalen-1-yl group, 4-(2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenyl naphthalene-2-yl group, 4-(2-methylphenyl)naphthalene-2-yl group, 4-(3-methylphenyl)naphthalene-2-yl group, 4-(4-methylphenyl)naphthalene-2-yl basis

(5): 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9′-spirobifluorenyl group, 9-phenanthryl group, 2-phenanthryl group, 11,11′-dimethylbenzo[ a]fluoren-9-yl group, 11,11′-dimethylbenzo[a]fluoren-3-yl group, 11,11′-dimethylbenzo[b]fluoren-9-yl group, 11,11′-dimethylbenzo [b] fluoren-3-yl group, 11,11′-dimethylbenzo[c]fluoren-9-yl group, 11,11′-dimethylbenzo[c]fluoren-2-yl group, 3-fluoranthenyl group , 8-fluoranthenyl group

(6): 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2-( 2-naphthyl)-3,4-dimethyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2- imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl- 2-imidazolyl group, 1-phenyl-4,5-dimethyl-2-imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group

(7): 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1 -phenyl-5-pyrazolyl group

(8): 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group

(9): 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group

(10): 2-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group, 2,2'-bipyridin- 5-yl group, 2,3'-bipyridin-3-yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, pyrazyl group, 1 , 3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group

(11): 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl-2-benzimidazolyl group, 1-methyl-5 -benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1- methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl-2-phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group , 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group

(12): 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzisothiazolyl group, 4-benzisothiazolyl group, 5-benzisothiazolyl group lyl group, 6-benzisothiazolyl group, 7-benzisothiazolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group

(13): 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzoisoxazolyl group, 4-benzisoxazolyl group, 5-benzisoxazolyl group, 6-benzisoxazolyl group, 7-benzisoxazolyl group, 2,1,3-benzoxadiazolyl- 4-yl group, 2,1,3-benzoxadiazolyl-5-yl group

(14): 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2- quinoxalyl group, 6-quinoxalyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group

(15): 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group

(16): 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group

(17): 9-methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3 -yl group, 9-phenylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazol-3-yl group, 9-biphenylcarbazol-4-yl group

(18): 2-thiantryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group

(19): 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 9-phenylcarbazol-4-yl group

(20): 4-(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl) ) phenyl group, 3-(4-pyridyl) phenyl group

(21): 4-(2-phenylimidazol-1-yl)phenyl group, 4-(1-phenylimidazol-2-yl)phenyl group, 4-(2,3,4-triphenylimidazol-1-yl ) phenyl group, 4-(1-methyl-4,5-diphenylimidazol-2-yl) phenyl group, 4-(2-methylbenzimidazol-1-yl) phenyl group, 4-(2-phenylbenzimidazole- 1-yl)phenyl group, 4-(1-methylbenzimidazol-2-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(2-methylbenzimidazol-1- yl)phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(1-methylbenzimidazol-2-yl)phenyl group, 3-(1-phenylbenzimidazol-1-yl) phenyl group

(22): 4-(3,5-diphenyltriazin-1-yl)phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophen-2-yl group , 5-phenylfuran-2-yl group, 4-(5-phenylthiophen-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5-phenylthiophene-2 -yl)phenyl group, 3-(5-phenylfuran-2-yl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl) ) phenyl group, 3-(3-benzothienyl) phenyl group, 4-(2-dibenzothienyl) phenyl group, 4-(4-dibenzothienyl) phenyl group, 3-(2-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4-(2-dibenzofuranyl) phenyl group, 4-(4-dibenzofuranyl) phenyl group, 3-(2-dibenzofuranyl) phenyl group, 3-(4- dibenzofuranyl)phenyl group, 5-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridin-3-yl group, 4-(9-carbazolyl)phenyl group, 3-( 9-carbazolyl)phenyl group

(23): 2-dibenzo[g,p]chrysenyl group, 3-dibenzo[g,p]chrysenyl group, 2-(7-phenyl)dibenzo[g,p]chrysenyl group, 3-(7-phenyl)dibenzo [g, p] chrysenyl group

(24): N,N-diphenylamino group, N,N-bis(4-biphenylyl)-amino group, N,N-bis(3-biphenylyl)-amino group, N-phenyl-4-biphenylamino group, N-phenyl-3-biphenylamino group, N-(4-biphenyl)-4-p-terphenylamino group, N-[4-(carbazol-9-yl)phenyl]-4-biphenylamino group, N ³ -[1,1′-biphenyl]-4-yl-N ¹ ,N ¹ -diphenyl-1,3-benzenediamino group, 4-triphenylamino group, 3-triphenylamino group, 4-(4 ',4''-diphenyl)triphenylamino group, 3-(4',4''-diphenyl)triphenylamino group, N ¹ ,N ¹ ,N ³ ,N ³ -tetraphenyl-1,3-benzene diamino group, 4-(phenylamino)triphenylamino group

In formulas (5) to (10), A ¹ to A ⁶ are each independently from the viewpoint of availability of raw materials,
phenyl group, biphenylyl group, pyridylphenyl group, terphenylyl group, naphthyl group, phenanthryl group, pyrenyl group, 9,9-spirobi[9H-fluorenyl] group, triphenylenyl group, dibenzothienyl group, dibenzofuranyl group, pyridyl group, pyrimidyl groups, or groups in which these groups are substituted with a cyano group, a nitro group, a hydroxyl group, a thiol group, a fluorine atom, a chlorine atom, a methyl group, or a methoxy group;
fluorenyl group, benzofluorenyl group, anthryl group, dibenzo[g,p]chrysenyl group, carbazolyl group, or these groups, cyano group, nitro group, hydroxyl group, thiol group, fluorine atom, chlorine atom, methyl a group substituted with a group, a methoxy group, or a phenyl group;
4,6-diphenyl-1,3,5-triazin-2-yl group, (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl group, 4,6-bis(4-biphenylyl )-1,3,5-triazin-2-yl group, 4,6-bis(3-biphenylyl)-1,3,5-triazin-2-yl group, cyano group, nitro group, hydroxyl group, thiol group , fluorine atom, chlorine atom, diphenylphosphine oxide, triphenylsilyl group, dihydroxyboryl group (-B(OH) ₂ ), 4,4,5,5-tetramethyl-[1,3,2]-dioxaboro ranyl group, 5,5-dimethyl-[1,3,2]-dioxaborinane group, methyl group, N,N-diphenylamino group, N,N-bis(4-biphenylyl)amino group, N ³ -[1 ,1′-biphenyl]-4-yl-N ¹ ,N ¹ -diphenyl-1,3-benzenediamino group, N-phenyl-3-biphenylylamino group, 4-triphenylamino group, 3-triphenylamino 4-(4′,4″-diphenyl)triphenylamino group, 3-(4′,4″-diphenyl)triphenylamino group, N ¹ ,N ¹ ,N ³ ,N ³ -tetraphenyl A -1,3-benzenediamino group or a 4-(phenylamino)triphenylamino group is preferred.

<Reaction of Compound Represented by Formula (1) and Compound Represented by Formula (2)>
A diaryl compound represented by the formula (1) and a diarylalkyne compound represented by the formula (2) are reacted in the presence of a catalyst and a base to give a phenanthrene compound represented by the formula (3′), A condensed ring compound represented by formula (3) can be obtained directly.

The starting compound represented by Formula (1) or Formula (2) can be synthesized according to a known method, or a commercially available compound can be used.

As the catalyst, a palladium-based catalyst is preferable from the viewpoint of yield.
Palladium catalysts include, for example, palladium(II) acetate, palladium(II) chloride, palladium(II) pivalate, palladium trifluoroacetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(acetonitrile)palladium(II) ) bis(tetrafluoroborate), tris(benzylideneacetone)palladium(0), tetrakis(triphenylphosphine)palladium(0) and the like. Among them, palladium(II) acetate is more preferable from the viewpoint of yield.
When using the above palladium catalyst, a compound serving as a ligand may be used as necessary. Examples of _{ligands include tricyclohexylphosphine (PCy3), tritertiarybutylphosphine (PtBu3), ditertiarybutylmethylphosphine (PtBu2Me )} ^, _{tricyclohexylphosphonium} tetrafluoroborate ⁽ PCy ₃ ·HBF ₄ ), tri-t-butylphosphonium tetrafluoroborate (P ^t Bu ₃ ·HBF ₄ ), di-t-butylmethylphosphonium tetrafluoroborate (P ^t Bu ₂ Me·HBF ₄ ), 1,3-bis( 2,6-diisopropylphenyl)imidazolium chloride (IPR/HCl), 1,2-bis(diphenylphosphino)ethane (dppe), 1,2-bis(dicyclohexylphosphino)ethane, triadamantylphosphine and the like. . Among them, tricyclohexylphosphine (PCy ₃ ), tritertiarybutylphosphine (P ^t Bu ₃ ), ditertiarybutylmethylphosphine ( ^Pt Bu ₂ Me), tricyclohexylphosphonium tetrafluoroborate ( PCy _{3.HBF 4} ), tri-t-butylphosphonium tetrafluoroborate (P ^t Bu _{3.HBF 4} ), di-t-butylmethylphosphonium tetrafluoroborate (P ^t Bu ₂ Me.HBF ₄ ), and tricyclohexylphosphine. (PCy ₃ ), tri-tert-butylphosphine (P ^t Bu ₃ ), di-tert-butylmethylphosphine (P ^t Bu ₂ Me), tri-t-butylphosphonium tetrafluoroborate (P ^t Bu _{3.HBF 4} ), di-t -Butylmethylphosphonium tetrafluoroborate (P ^t Bu ₂ Me.HBF ₄ ) is more preferred.

Examples of bases include sodium carbonate, potassium carbonate, cesium carbonate, potassium phosphate, sodium acetate, potassium acetate, potassium t-butoxy, potassium pivalate, and cesium pivalate. The use of these bases is preferred because it results in higher yields. Among them, potassium carbonate, sodium acetate, potassium acetate, or cesium pivalate is preferable, and potassium acetate or sodium acetate is more preferable, from the viewpoint of yield.

Solvents include, for example, dimethylformamide, dimethylacetamide, and N-methyl-2-pyrrolidone. Among them, dimethylformamide or dimethylacetamide is preferable from the viewpoint of yield.

From the viewpoint of yield, the reaction temperature is preferably room temperature or higher and 200° C. or lower, more preferably 110° C. or higher and 200° C. or lower, and particularly preferably 130° C. or higher and 200° C. or lower. Here, room temperature means 10° C. or higher and 30° C. or lower.
From the viewpoint of maintaining the catalytic activity, the reaction atmosphere is preferably a dry nitrogen atmosphere or a dry argon atmosphere.

As described above, the production method according to one embodiment of the present invention described above can produce more A condensed ring compound can be produced by a simple process.

The condensed ring compound represented by Formula (3) can be used, for example, as a material for organic electroluminescence devices, such as a hole injection material, a hole transport material, a light-emitting layer material, an electron transport material, and an electron injection material. Furthermore, the condensed ring compound represented by the formula (3) is not limited to use in organic electroluminescence devices, but in the field of organic photoconductive materials such as electrophotographic photoreceptors, photoelectric conversion devices, solar cells, and image sensors. can also be used, and is not particularly limited.

EXAMPLES The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples. The analysis methods and measurement methods used in the examples are as follows.

[Material purity measurement (HPLC analysis)]
Measuring device: Multi-station LC-8020 manufactured by Tosoh Corporation
Measurement conditions: column Inertsil ODS-3V (4.6 mmΦ × 250 mm)
Detector UV detection (wavelength 254 nm),
Eluent methanol/tetrahydrofuran = 9/1 (v/v ratio)
[NMR measurement]
NMR measurement was performed using JEOL JNM-ECA-600 (manufactured by JEOL Ltd.).

[Example 1] (Synthesis of dibenzo[g,p]chrysene)

Under a nitrogen stream, 1-bromo-2-(phenylethynyl)-benzene 51.4 mg (0.20 mmol), 2-iodobiphenyl 56 mg (0.20 mmol), palladium acetate 8.96 mg (0.20 mmol) were placed in a 25 mL screw cap test tube. 04 mmol), 21.4 mg (0.06 mmol) of tricyclohexylphosphonium tetrafluoroborate, 58.8 mg (0.6 mmol) of potassium acetate, and 2 mL of N,N-dimethylformamide were added, sealed, and stirred at 130° C. for 18 hours. . After cooling to room temperature, 2 mL of dichloromethane was added for dilution. After removing insoluble matter by filtration, 4 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified by column chromatography (hexane) to isolate 34.7 mg (53% yield) of pale yellow powder of dibenzo[g,p]chrysene.

Identification of the compound was carried out by ¹ H-NMR measurement.
¹ H-NMR (CDCl ₃ ); 7.56-7.72 (m, 8H), 8.67-8.75 (m, 8H)

According to Example 1 above, it is possible to synthesize dibenzo[g,p]chrysene in one pot, and compared with the methods described in Non-Patent Documents 1 to 3, dibenzo[g, It was found that the synthesis of p]chrysene can be realized. In addition, in the method described in Non-Patent Document 2, the conversion of dibenzo[g,p]chrysene is about 14%, while in Example 1, dibenzo[g,p]chrysene can be obtained with a yield of 53%. , it was found possible to produce fused ring compounds in very high yields.

Claims (10)

A method for producing a condensed ring compound represented by formula (3),
A production method comprising reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a palladium catalyst and a base:

During the ceremony,
X ¹ to X ⁴ are each independently one or more atoms selected from the group consisting of a carbon (C) atom, an oxygen (O) atom and a sulfur (S) atom, which may have a substituent Represents a monocyclic, dicondensed or tricondensed aromatic ring consisting of;
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom. the sum of the number of oxygen (O) atoms and the number of sulfur (S) atoms constituting each aromatic ring represented by X ¹ to X ⁴ is 0 or more and 2 or less in each of X ¹ to X ⁴ ; The manufacturing method according to claim 1, wherein Claim 1, wherein each of X ¹ to X ⁴ is independently a monocyclic, bicondensed or tricondensed aromatic ring consisting only of carbon (C) atoms and optionally having a substituent. The manufacturing method described in . The production method according to any one of claims 1 to 3, wherein X ¹ to X ⁴ are each independently a benzene ring, naphthalene ring or phenanthrene ring which may have a substituent. X ¹ and X ² represent an optionally substituted monocyclic aromatic ring;
Either one of X ³ and X ⁴ is an optionally substituted bi- or tri-condensed aromatic ring, and the other is an optionally substituted monocyclic aromatic ring. A manufacturing method according to any one of claims 1 to 4. The production method according to any one of claims 1 to 5, wherein X ¹ and X ² are the same aromatic ring. 7. The production method according to any one of claims 1 to 6, wherein the substituent each of X ¹ to X ⁴ may have is a charge-transporting group. The production method according to any one of claims 1 to 7, wherein the reaction is a reaction represented by any one of formulas (5) to (11):

In formula (5),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁴ each independently represent a charge-transporting group;
k1 to k4 are each independently an integer of 0 to 4:
In each of formulas (6) to (10),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁵ each independently represent a charge-transporting group;
k1 to k4 are each independently an integer of 0 to 4;
k5 is an integer between 0 and 2:
In formula (11),
Z ¹ and Z ² each independently represent a bromine atom or an iodine atom;
A ¹ to A ⁴ and A ⁶ each independently represent a charge-transporting group;
k1 to k4 and k6 are each independently an integer of 0 or more and 4 or less. Each of the charge-transporting groups independently
deuterium atom;
fluorine atom, chlorine atom;
trifluoromethyl group;
pentafluoroethyl group;
cyano group;
nitro group;
hydroxyl group;
thiol group;
optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms;
optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms;
a phosphine oxide group optionally having a substituent;
a silyl group optionally having a substituent;
a boronyl group optionally having a saturated hydrocarbon group having 2 to 10 carbon atoms;
straight or branched alkyl group having 1 to 18 carbon atoms;
a linear or branched alkoxy group having 1 to 18 carbon atoms; or
The production method according to claim 7 or 8, which is a group represented by formula (4) or (4'):

In formula (4),
R ¹ and R ² each independently
hydrogen atom;
deuterium atom;
optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms;
optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms; or
represents a linear or branched alkyl group having 1 to 18 carbon atoms;
L is
a phenylene group optionally substituted with a methyl group or a phenyl group;
a naphthylene group optionally substituted with a methyl group or a phenyl group,
a biphenylene group optionally substituted with a methyl group or a phenyl group, or
representing a single bond;
n represents 1 or 2,
if L is a single bond, n is 1;
n is 1 or 2 when L is not a single bond:
In formula (4′),
R ¹ to R ³ are each independently
hydrogen atom;
deuterium atom;
optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms;
optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 36 carbon atoms; or
represents a linear or branched alkyl group having 1 to 18 carbon atoms;
L is
a phenylene group optionally substituted with a methyl group or a phenyl group;
a naphthylene group optionally substituted with a methyl group or a phenyl group;
a biphenylene group optionally substituted with a methyl group or a phenyl group, or
represents a single bond. 10. The base according to any one of claims 1 to 9 , wherein the base is sodium carbonate, potassium carbonate, cesium carbonate, potassium phosphate, sodium acetate, potassium acetate, potassium t-butoxy, potassium pivalate or cesium pivalate. Production method.