JP7713396B2 - Polymer, and electroluminescent device material and electroluminescent device using said polymer - Google Patents

Description

The present invention relates to a polymer, and an electroluminescent device material and an electroluminescent device that use the polymer.

Research and development of electroluminescence elements (EL elements) is currently underway. In particular, EL elements are considered to be promising for use as inexpensive, solid-state light-emitting, large-area, full-color display elements and writing light source arrays. EL elements are light-emitting elements that have a thin film of several nanometers to several hundred nanometers between an anode and a cathode. EL elements also typically have a hole transport layer, a light-emitting layer, an electron transport layer, and the like.

Among these, materials for the light-emitting layer include fluorescent materials and phosphorescent materials. Compared to fluorescent materials, phosphorescent materials are expected to have higher light-emitting efficiency. Furthermore, in order to cover a wide color gamut, RGB light sources are required to have emission spectra with narrow half-widths. In particular, deep blue is required for blue, but currently no elements have been found that satisfy the requirements for long life and color purity.

As a method for solving these problems, there is a light-emitting device that uses "quantum dots," an inorganic light-emitting material, as a light-emitting material (Patent Document 1). Quantum dots (QDs) are semiconductor materials with a crystal structure of several nanometers in size, and are composed of hundreds to thousands of atoms. Quantum dots have a large surface area per unit volume because they are very small in size. Therefore, most of the atoms are present on the surface of the nanocrystals, and they exhibit quantum confinement effects. Due to this quantum confinement effect, quantum dots can adjust the emission wavelength simply by adjusting their size, and have characteristics such as excellent color purity and high PL (photoluminescence) efficiency, which has attracted much attention. A quantum dot light emitting diode (QD LED) is known as a basic element having a three-layer structure including a quantum dot light emitting layer at either end, a hole transport layer (HTL) at either end, and an electron transport layer (ETL).

JP 2010-199067 A

However, electroluminescence elements (particularly quantum dot electroluminescence elements) using the hole transport material described in Patent Document 1 have been unable to achieve sufficient performance (particularly durability).

Therefore, the present invention has been made in consideration of the above circumstances, and aims to provide a technology that can improve the performance (particularly the durability) of electroluminescent elements (particularly quantum dot electroluminescent elements).

The present inventors conducted intensive research to solve the above problems. As a result, they discovered that the above problems can be solved by using a polymer with a specific structure, and thus completed the present invention.

That is, the above object can be achieved by a polymer having a structural unit (A) represented by the following formula (1):

In the above formula (1),
Ar ¹ to Ar ³ each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms;
^Ar4 is a substituted or unsubstituted fused polycyclic aromatic hydrocarbon group having three or more fused benzene rings;
^Ar5 is a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring atoms;
^Ar6 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 60 ring atoms;
p is 0 or 1.

The present invention provides an electroluminescence element (particularly a quantum dot electroluminescence element) with excellent performance (particularly durability).

1 is a schematic diagram showing an electroluminescence element according to one embodiment of the present invention;

In a first aspect, the present invention provides a polymer having a structural unit (A) represented by the following formula (1):

In the above formula (1),
Ar ¹ to Ar ³ each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms;
^Ar4 is a substituted or unsubstituted fused polycyclic aromatic hydrocarbon group having three or more fused benzene rings;
^Ar5 is a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring atoms;
^Ar6 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 60 ring atoms;
p is 0 or 1.

In this specification, the structural unit (A) represented by the above formula (1) is also referred to as "structural unit (A) represented by formula (1)", "structural unit (A)" or "structural unit (A) according to the present invention". In addition, the following structure in "structural unit (A) represented by formula (1)":

A structural unit having the formula (1) is also referred to as "structural unit X" or "structural unit X according to the present invention". Similarly, the structural unit "-Ar ⁶ -" in "structural unit (A) represented by formula (1)" is also referred to as "structural unit Y" or "structural unit Y according to the present invention". Furthermore, a polymer having a structural unit represented by formula (1) is also referred to as "polymer", "polymer according to the present invention" or "polymer according to one embodiment of the present invention".

In a second aspect, the present invention provides an electroluminescent device material comprising the polymer according to the present invention.

In a third aspect, the present invention provides an electroluminescence device comprising a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein at least one layer of the organic film comprises the polymer according to the present invention. In this specification, the electroluminescence device is also referred to simply as "LED". The quantum dot electroluminescence device is also referred to simply as "QLED". The organic electroluminescence device is also referred to simply as "OLED".

Various low-molecular-weight materials and polymeric materials are used as materials for composing the light-emitting layer and carrier transport layer of electroluminescent elements. Of these, low-molecular-weight materials are superior in terms of the efficiency and lifespan of the element. However, when using low-molecular-weight materials, there is a problem that the manufacturing cost is high because it is necessary to create the element by a vacuum process. On the other hand, as a polymeric material, TFB and the like are known as hole transport materials (for example, paragraphs "0036" and "0037" of Patent Document 1). However, such polymeric materials do not have a sufficiently long durability (light-emitting lifespan) (see Comparative Example 2-1 below). For this reason, there is a demand for the development of polymeric materials that can improve durability (light-emitting lifespan).

The present inventors have conducted extensive research into means for solving the above problems (particularly for improving durability (luminescence lifetime)). As a result, they have found that by applying a polymer having a structural unit (A) represented by formula (1) to an electroluminescence element, the luminescence lifetime can be improved compared to the case where a known material is used. The mechanism by which the above-mentioned effect is achieved by the configuration of the present invention is presumed to be as follows.

Triarylamine-based polymer materials such as TFB are conventionally known as hole transport materials. TFB has the following structure in which an aryl group or arylene group is bonded to a nitrogen atom.

The inventors speculated that the insufficient durability (luminescence lifetime) of such triarylamine-based polymeric materials is mainly due to the weak bond between the nitrogen atom and the aryl group or arylene group. More specifically, when a triarylamine-based polymeric material such as TFB is used as a hole transport material, the bond between the nitrogen atom and the aryl group or arylene group (particularly the bond between the nitrogen atom and the aryl group contained as a side chain) is easily cleaved when the polymeric material comes into contact with electrons leaking from the electron injection layer or excitons generated in the hole transport layer (HTL), and therefore sufficient durability (luminescence lifetime) is not obtained.

In contrast, the polymer according to one embodiment of the present invention can improve durability (luminescence lifetime) by having the structural unit (A) represented by formula (1). Here, the structural unit (A) has three aromatic hydrocarbon groups bonded to the nitrogen atom as "Ar ¹ to Ar ³ ", and further has a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed as "Ar ⁴ ". That is, the structural unit (A) contains the above-mentioned condensed polycyclic aromatic hydrocarbon group as "Ar ⁴ " via "Ar ³ " in the side chain. And, it is presumed that the condensed polycyclic aromatic hydrocarbon group contained as "Ar ⁴ " has a high resonance energy, and therefore brings about a high resonance stabilization effect. Therefore, in the triarylamine-based polymer material, the bond between the nitrogen atom and the aryl group or arylene group becomes strong (the bond energy becomes large), and as a result, the above bond is less likely to be cleaved even when it comes into contact with electrons or excitons, and therefore it is considered that the durability (luminescence lifetime) is improved.

The inventors have also found that sufficient luminous efficiency can be achieved by applying a polymer having the structural unit (A) represented by formula (1) to an electroluminescence device (particularly a quantum dot electroluminescence device (QLED)). The mechanism by which the above-mentioned effects of the configuration of the present invention are exhibited is presumed to be as follows.

The valence band level of quantum dots used in quantum dot electroluminescence devices is, for example, about -5.7 eV for blue QLEDs and about -5.55 eV for red QLEDs. This results in a large band offset with the HOMO level of hole transport layer materials used in existing organic electroluminescence devices (OLEDs), resulting in problems such as reduced carrier injection efficiency and luminous efficiency. To solve this problem, there is a demand for a technology that can lower the band offset with the emission layer (QD (Quantum Dot) layer) by using a hole transport layer material with a deeper HOMO level of the hole transport layer (HTL).

In contrast, according to a polymer according to one embodiment of the present invention, the structure of the above formula (1), particularly the structural unit X in the above formula (1), has the following structure:

It is presumed that a substance with a deep HOMO level can be obtained by making the above-mentioned structure. Specifically, the above-mentioned structural unit X has a structure in which a monoamine (-(Ar ¹ )-N(Ar ³ )-(Ar ² )-) is arranged in the main chain. And, Ar ³ is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring-forming atoms, and Ar ⁴ is a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed, so that steric hindrance is large. Therefore, as a stable structure, Ar ³ and Ar ⁴ have a twisted structure. As a result, the length of conjugation is shortened, and therefore, it is considered that the HOMO level of the polymer according to one embodiment of the present invention is deep.

Therefore, in a quantum dot electroluminescence element having a hole injection layer or hole transport layer (particularly the hole transport layer) containing the polymer according to one embodiment of the present invention and a light-emitting layer containing quantum dots, the HOMO level difference (barrier) between the hole injection layer or hole transport layer (particularly the hole transport layer) and the light-emitting layer is small, and the ability to inject holes from these layers to the light-emitting layer can be improved. In addition, since the ability to inject holes into the light-emitting layer can be improved, it is also possible to widen the light-emitting region. Therefore, by using the polymer according to one embodiment of the present invention, an electroluminescence element that exhibits good light-emitting efficiency can be produced.

Note that the above mechanism is speculative, and the present invention is not limited to the above mechanism.

The following describes an embodiment of the present invention. Note that the present invention is not limited to the following embodiment. Also, the drawings are exaggerated for the convenience of explanation, and the dimensional ratios of the components in each drawing may differ from the actual ratios. Also, when the embodiment of the present invention is explained with reference to the drawings, the same elements are given the same reference numerals in the explanation of the drawings, and duplicate explanations are omitted.

Unless otherwise specified, in this specification, operations and measurements of physical properties are performed at room temperature (20°C or higher and 25°C or lower) and at a relative humidity of 40% RH or higher and 50% RH or lower.

In this specification, "x and y are each independently" means that x and y may be the same or different.

In this specification, the term "group derived from compound z" or "group derived from compound z" refers to a group obtained by removing hydrogen atoms directly bonded to ring-forming atoms from the ring structure of compound z, in the amount equal to the valence, to leave free valences.

In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The same applies to the number of ring atoms described below unless otherwise specified.

For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, a pyridine ring has 6 ring atoms, and a furan ring has 5 ring atoms.

When a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of ring atoms of the benzene ring. Therefore, the number of ring atoms of a benzene ring substituted with an alkyl group is 6. Also, when a naphthalene ring is substituted with, for example, an alkyl group, the number of atoms of the alkyl group is not included in the number of ring atoms of the naphthalene ring. Therefore, the number of ring atoms of a naphthalene ring substituted with an alkyl group is 10.

For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of ring atoms of the pyridine ring. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.

In this specification, unless otherwise defined, "substituted" refers to being substituted with an alkyl group, a cycloalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxy group, a cycloalkoxy group, an alkenyl group, an alkynyl group, an amino group, an aryl group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a hydroxy group (-OH), a carboxy group (-COOH), a thiol group (-SH), or a cyano group (-CN). When a group is substituted, the form of substitution that is included in the definition before the substituted structure is further substituted is excluded. For example, when the substituent is an alkyl group, this alkyl group as a substituent is not further substituted with an alkyl group. In addition, these substituents may be bonded to each other to form a ring.

Here, the alkyl group as a substituent may be either linear or branched, and is preferably linear and branched having 1 to 20 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-isopropylpropyl, 1-ethyl-4-isopropylpropyl, 1-ethyl-5-isopropylpropyl, 1-ethyl-6-isopropylpropyl, 1-ethyl-7-isopropylpropyl, 1-ethyl-8-isopropylpropyl, 1-ethyl-9-isopropylpropyl, 1-ethyl-10-isopropylpropyl, 1-ethyl-11-isopropylpropyl, 1-ethyl-12-isopropylpropyl, 1-ethyl-13-isopropylpropyl, 1-ethyl-14-isopropylpropyl, 1-ethyl-15-isopropylpropyl, 1-ethyl-16-isopropylpropyl, 1-ethyl-17-isopropylpropyl, 1-ethyl-18-isopropylpropyl, 1-ethyl-19-isopropylpropyl, 1-ethyl-20-isopropylpropyl, 1-ethyl-21-isopropylpropyl, 1-ethyl-22-isopropylpropyl, 1-ethyl-23-isopropylpropyl, 1-ethyl-24-isopropylpropyl, 1-ethyl-25-isopropylpropyl, 1-ethyl-26-isopropylpropyl, 1-ethyl-27-isopropylpropyl, 1-ethyl-28-isopropylpropyl, 1-ethyl-29-isopropylpropyl, 1-ethyl-29-isopropylpropyl, 1-ethyl-29-isopropylpropyl, 1-ethyl- Examples of such alkyl groups include butyl, octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropyl, 1-tert-butyl-2-methylpropyl, n-nonyl, 3,5,5-trimethylhexyl, n-decyl, isodecyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, nonadecyl, and icosyl groups.

Examples of cycloalkyl groups as substituents include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

Examples of hydroxyalkyl groups include those in which the above alkyl groups are substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) hydroxy groups (e.g., hydroxymethyl groups, hydroxyethyl groups).

Examples of the alkoxyalkyl group as a substituent include the above alkyl group substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) of the above alkoxy groups.

The alkoxy group as a substituent may be either linear or branched, but is preferably linear with 1 to 20 carbon atoms or branched with 3 to 20 carbon atoms. Examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, 2-ethylhexyloxy, and 3-ethylpentyloxy.

Examples of cycloalkoxy groups as substituents include cyclopropyloxy groups, cyclobutyloxy groups, cyclopentyloxy groups, and cyclohexyloxy groups.

Examples of alkenyl groups as substituents include vinyl groups, allyl groups, 1-propenyl groups, isopropenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 1-pentenyl groups, 2-pentenyl groups, 3-pentenyl groups, 1-hexenyl groups, 2-hexenyl groups, 3-hexenyl groups, 1-heptenyl groups, 2-heptenyl groups, 5-heptenyl groups, 1-octenyl groups, 3-octenyl groups, and 5-octenyl groups.

Examples of alkynyl groups as substituents include acetylenyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 1-heptynyl, 2-heptynyl, 5-heptynyl, 1-octynyl, 3-octynyl, and 5-octynyl.

The aryl group as a substituent is preferably an aryl group having 6 to 30 carbon atoms. Examples include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, an anthryl group, a pyrenyl group, an azulenyl group, an acenaphthylenyl group, a terphenyl group, and a phenanthryl group.

Examples of aryloxy groups as substituents include phenoxy and naphthyloxy groups.

Examples of alkylthio groups as substituents include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, and dodecylthio groups.

Examples of cycloalkylthio groups as substituents include cyclopentylthio and cyclohexylthio groups.

Examples of arylthio groups as substituents include phenylthio and naphthylthio groups.

Examples of alkoxycarbonyl groups as substituents include methyloxycarbonyl groups, ethyloxycarbonyl groups, butyloxycarbonyl groups, octyloxycarbonyl groups, and dodecyloxycarbonyl groups.

Examples of aryloxycarbonyl groups as substituents include phenyloxycarbonyl groups and naphthyloxycarbonyl groups.

[Polymer]
The polymer of the present invention has a structural unit (structural unit (A)) represented by the following formula (1). In the polymer having the following structure, the bond between the nitrogen atom contained in the main chain and the aryl group or arylene group is strong (the bond energy is large), and these bonds are not easily cleaved even when contacted with electrons or excitons. For this reason, an electroluminescent device (particularly a quantum dot electroluminescent device) containing the polymer of the present invention (particularly in a hole transport layer or hole injection layer) has excellent durability (light emission lifetime).

In addition, the polymer having the following structure has a deep HOMO level. Therefore, an electroluminescence device (particularly a quantum dot electroluminescence device) containing the polymer of the present invention (particularly in a hole transport layer or hole injection layer) can obtain good luminous efficiency. The polymer of the present invention may contain one type of structural unit (structural unit (A)) of formula (1), or may contain two or more types of structural units (A). Note that the multiple structural units (A) may be present in a block form, a random form, an alternating form, or a periodic form.

In the above formula (1), the structural unit X (the structural unit on the left side of the above formula (1); that is, a structural unit in which a nitrogen atom (and further, Ar ³ as a side chain, etc.) is sandwiched between ^{Ar 1} and Ar ² ) constitutes a polymer according to one embodiment of the present invention. When two or more types of structural units (A) are present, the "structural unit X" in each structural unit (A) may be the same or different. Similarly, in the above formula (1), the structural unit Y (the structural unit on the right side of the above formula (1); that is, the structural unit represented by "Ar ⁶ ") constitutes a polymer according to one embodiment of the present invention, and when two or more types of structural units (A) are present, the "structural unit Y" in each structural unit (A) may be the same or different.

In other words, the polymer according to the present invention can be said to be a copolymer containing the above-mentioned structural unit X and structural unit Y. The polymer according to the present invention contains at least one structural unit (A) represented by the above formula (1), and has a form in which the structural unit X and the structural unit Y are copolymerized alternately (i.e., an alternating copolymer).

In the above formula (1), Ar ¹ to Ar ³ (Ar ¹ , Ar ² and Ar ³ ) each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms. In this case, Ar ¹ to Ar ³ may be the same or different, but it is preferable that Ar ¹ and Ar ² are the same.

The aromatic hydrocarbon groups represented by Ar ¹ to Ar ³ may be monocyclic or condensed rings. The divalent aromatic hydrocarbon group having 6 to 60 ring atoms is not particularly limited, and examples thereof include a phenylene group, an indenylene group, a naphthalenylene group, an anthracenylene group, an azulenylene group, an acenaphthenylene group, a phenalenylene group, a fluorenylene group, a phenanthrenylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, a quinquiphenylene group, a pyrenylene group, a spirobifluorenylene group, and groups formed from combinations thereof.

Ar ¹ to Ar ³ are each preferably a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring atoms, and more preferably a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 20 ring atoms.

Furthermore, it is preferable that Ar ¹ to Ar ³ are each independently a group selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, and a substituted or unsubstituted fluorenylene group.

Among these, from the viewpoint of further improving durability, more preferably, Ar ¹ and Ar ² are each independently selected from a substituted or unsubstituted phenylene group (o, m, p-phenylene group) and a substituted or unsubstituted fluorenylene group. Particularly preferably, Ar ¹ and Ar ² are selected from an unsubstituted phenylene group and a substituted fluorenylene group. Most preferably, Ar ¹ and Ar ² are selected from an unsubstituted p-phenylene group and a substituted fluorenylene group. Furthermore, in the above embodiment, the group substituting the fluorenylene group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. Here, examples of the alkyl group having 1 to 20 carbon atoms include the same alkyl groups as those listed in the above "substituent". Furthermore, the alkyl group may be linear or branched, but is preferably linear.

From the same viewpoint as above, Ar ³ is more preferably a group selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, and a substituted or unsubstituted fluorenylene group. Ar ³ is particularly preferably any of the groups represented by the following formulae (2) to (4):

In the above formula (3),
^R1 and ^R2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case ^R1 and ^R2 may be bonded to each other to form a ring.

In this case, R ¹ and R ² may be the same or different, but it is preferable that R ¹ and R ² are the same.

The aromatic hydrocarbon group represented by R ¹ and R ² preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The alkyl group represented by R ¹ and R ² preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, and most preferably 3 to 8 carbon atoms.

The aromatic hydrocarbon groups represented by R ¹ and R ² may be monocyclic or condensed. Specific examples of the aromatic hydrocarbon groups represented by R ¹ and R ² are not particularly limited, but include, for example, a phenyl group, a naphthyl group, a phenanthryl group, a biphenylenyl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a fluorenyl group, an azulenyl group, an acenaphthenyl group, a fluoranthenyl group, a naphthacenyl group, a perylenyl group, a pentacenyl group, a terphenylenyl group, a quaterphenylenyl group, a chrysenyl group, and groups formed from combinations thereof.

Specific examples of the alkyl group as R ¹ and R ² are not particularly limited, but include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a tert-butyl group, an i-butyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an i-pentyl group, a neopentyl group, a tert-pentyl group (a t-pentyl group), a cyclopentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, a n -hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group (4-t-butylcyclohexyl group), n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group (t-octyl group), 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group , 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, Examples of the alkyl group include a 2-hexylhexadecyl group, a 2-octylhexadecyl group, a n-heptadecyl group, a n-octadecyl group, a n-nonadecyl group, a n-icosyl group, a 2-ethylicosyl group, a 2-butylicosyl group, a 2-hexylicosyl group, a 2-octylicosyl group, a n-henicosyl group, a n-docosyl group, a n-tricosyl group, a n-tetracosyl group, a n-pentacosyl group, a n-hexacosyl group, a n-heptacosyl group, a n-octacosyl group, a n-nonacosyl group, and a n-triacontyl group.

Furthermore, the aromatic hydrocarbon group or the alkyl group as R ¹ may be bonded to the aromatic hydrocarbon group or the alkyl group as R ² via a single bond.

Among these, from the viewpoint of further improving durability, Ar ³ is preferably any one of the groups represented by the above formulas (2) and (3). More preferably, it is preferably a group selected from an unsubstituted phenylene group (o, m, p-phenylene group), a 9,9-diphenylfluorenylene group, and a 9,9-dialkylfluorenylene group. Particularly preferably, Ar ³ is a group selected from a substituted or unsubstituted phenylene group (o, m, p-phenylene group), and a 9,9-dialkylfluorenylene group. Considering the viewpoint of improving the durability as well as the hole injection ability and transportability and obtaining good luminous efficiency, Ar ³ is most preferably a 9,9-dialkylfluorenylene group (particularly, a form in which the 2-position and the 7-position are bonded to N (nitrogen atom) and Ar ^4, respectively). In addition, with respect to the 9,9-dialkylfluorenylene group as a preferred embodiment of Ar ³ , the preferred number of carbon atoms in the alkyl group bonded to the 9-position is the same as the preferred number of carbon atoms in the alkyl group as R ¹ and R ² in the above formula (3). Furthermore, the alkyl group may be linear or branched, but is preferably linear.

By combining Ar ¹ to Ar ³ in the preferred forms as described above, the resonance stabilization effect of Ar ⁴ is more likely to spread within the molecule, and the bonds between the nitrogen atom and each of Ar ¹ to Ar ³ are strengthened (the bond energy is increased), resulting in higher durability.

In the above formula (1), Ar ⁴ represents a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. That is, Ar ⁴ is a condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed, and the condensed polycyclic aromatic hydrocarbon group may be substituted or unsubstituted. The polymer of the present invention contains a condensed polycyclic aromatic hydrocarbon group in the side chain of the polymer as Ar ⁴ , and therefore has high durability due to its resonance stabilization effect. Therefore, in order to obtain a high resonance stabilization effect, it is preferable that the resonance energy of Ar ⁴ is 2.5 eV or more, more preferably 2.8 eV or more, and particularly preferably 3.0 eV or more.

On the other hand, although the upper limit is not particularly limited, as the resonance energy increases, the polymer may absorb light in the visible light region. Therefore, when the polymer of the present invention is used in a hole injection layer or a hole transport layer (particularly a hole transport layer), from the viewpoint of suppressing the absorption of visible light by these layers, the resonance energy of ^Ar4 is preferably 6.0 eV or less, and more preferably 5.5 eV or less.

Here, the method for determining the above-mentioned resonance energy is as follows. Specifically, the resonance energy can be determined by the method reported by Dewar and Gleicher et al. in the literature (J. Am. Chem. Soc. 87 685 (1965)).
calculated the heats of atomization of a series of chain conjugated hydrocarbons using a semi-empirical molecular orbital method and found that the heats of atomization of these compounds are additive with respect to each bond. Specifically, calculations are performed by assigning a unique reference bond energy to each of the C=C, C-C, and C-H bonds. The values of resonance energy used in this specification are values calculated according to this method.

In order to set the resonance energy of ^Ar4 within the above-mentioned preferred range, the number of rings in the condensed polycyclic aromatic hydrocarbon group contained as ^Ar4 is preferably 3 or more and 8 or less, more preferably 3 or more and 5 or less, particularly preferably 3 or 4, and most preferably 3.

Specific examples of the condensed polycyclic aromatic hydrocarbon group include monovalent or divalent groups derived from condensed polycyclic aromatic hydrocarbon compounds such as anthracene (resonance energy: 3.08 eV), phenanthrene (resonance energy: 3.43 eV), tetracene (resonance energy: 3.81 eV), chrysene (resonance energy: 4.51 eV), pyrene (resonance energy: 3.97 eV), triphenylene (resonance energy: 5.20 eV), benzo[a]anthracene, pentacene, and perylene (resonance energy: 5.06 eV).

Among them, Ar ⁴ is preferably a monovalent or divalent group derived from a compound selected from substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetracene, substituted or unsubstituted chrysene, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, and substituted or unsubstituted benzo[a]anthracene. More preferably, Ar ⁴ is a monovalent or divalent group derived from a compound selected from substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetracene, and substituted or unsubstituted chrysene. That is, in formula (1), Ar ⁴ is preferably a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted tetracenylene group, or a substituted or unsubstituted chrysenylene group. Even more preferably, Ar ⁴ is a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group. Particularly preferred is a substituted or unsubstituted anthracenyl group or a substituted or unsubstituted anthracenylene group, and most preferred is a substituted or unsubstituted anthracenylene group (particularly a form in which the 9- and 10-positions are bonded to ^Ar3 and ^Ar5 , respectively, i.e., a substituted or unsubstituted 9,10-anthracenylene group).

In the above formula (1), p represents the number of Ar ⁵ and is 0 or 1.

In the above formula (1), when p is 0, Ar ⁴ is a substituted or unsubstituted divalent condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed. Also, when p is 0, it means that Ar ⁵ does not exist. That is, when p is 0, the ring-forming atom of Ar ⁴ described as being capable of being bonded to Ar ⁵ is unsubstituted, and a hydrogen atom is bonded to the ring-forming atom. In other words, when p is 0, Ar ⁴ is a substituted or unsubstituted monovalent condensed polycyclic aromatic hydrocarbon group in which three or more benzene rings are condensed.

From the viewpoints of improving durability, obtaining a polymer with a deep HOMO level, and applying the polymer to an electroluminescence device (particularly, a quantum dot electroluminescence device (QLED)) to obtain sufficient luminous efficiency, it is preferable that p is 1.

In the above formula (1), when p is 1, ^Ar5 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring atoms.

The aromatic hydrocarbon group and aromatic heterocyclic group represented by Ar ⁵ may be a monocyclic or condensed ring. Specific examples of the monovalent aromatic hydrocarbon group having 6 to 60 ring atoms include divalent groups derived from the aromatic hydrocarbon compounds exemplified above for Ar ¹ to Ar ³ , which are converted to monovalent groups.

In addition, in this specification, an "aromatic heterocyclic group" is a substituent derived from an aromatic compound having one or more heteroatoms (e.g., nitrogen atom (N), oxygen atom (O), phosphorus atom (P), sulfur atom (S), silicon atom (Si), selenium atom (Se), etc.) as ring-forming atoms, and the remaining ring-forming atoms are carbon atoms (C). Specific examples of aromatic heterocyclic groups having 5 to 60 ring-forming atoms include, but are not limited to, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, benzoquinone, coumarin, fluorenone, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, pyrrole, indole, carbazole, imidazole, benzimidazole, Examples of monovalent groups derived from aromatic heterocyclic compounds include dazole, pyrazole, indazole, oxazole, isoxazole, benzoxazole, benzisoxazole, thiazole, isothiazole, benzothiazole, benzisothiazole, imidazolinone, benzimidazolinone, imidazopyridine, imidazopyrimidine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, and groups consisting of combinations thereof.

^Ar5 is preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 30 ring atoms, and more preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 15 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 15 ring atoms.

Furthermore, ^Ar5 is preferably a monovalent group selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.

Furthermore, ^Ar5 is preferably a monovalent group selected from a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.

Among these, from the viewpoint of further improving durability, it is preferable that, in the above formula (1), p is 1 and ^Ar5 is a group represented by the following formula (5) or (6):

In the above formula (5), ^R3 and ^R4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case ^R3 and ^R4 may be bonded to each other to form a ring.

The aromatic hydrocarbon group represented by R ³ and R ⁴ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The alkyl group represented by R ³ or R ⁴ preferably has 1 or more and 30 or less carbon atoms, more preferably has 1 or more and 15 or less carbon atoms, and particularly preferably has 1 or more and 10 or less carbon atoms.

Specific examples of the aromatic hydrocarbon group and alkyl group as ^R3 and ^R4 are the same as the specific examples of the aromatic hydrocarbon group and alkyl group given above for ^R1 and ^R2 , respectively, and therefore will not be described here. The aromatic hydrocarbon group or alkyl group as ^R3 may be bonded to the aromatic hydrocarbon group or alkyl group as ^R4 via a single bond.

In the above formula (5), a is 0, 1, 2, or 3, b is 0, 1, 2, 3, or 4, and when either a or b is 2 or more, each ^R3 or each ^R4 may be the same or different.

a and b respectively represent the number of ^R3 and ^R4 substituted on the ring-forming atoms contained in the structure of formula (5). When a or b is 0, it means that the corresponding ^R3 or ^R4 does not exist. That is, in the above formula (5), the ring-forming atom described so that the substituent ^R3 or ^R4 may be bonded thereto is unsubstituted, and a hydrogen atom is bonded to the ring-forming atom.

a is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. b is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.

In the above formula (5), X is a group selected from -C(R ⁵ )(R ⁶ )-, -O-, and -S-. In particular, from the viewpoint of further improving durability, X is preferably a group selected from -C(R ⁵ )(R ⁶ )- and -S-.

In the above formula (5), when X is -C(R ⁵ )(R ⁶ )-, R ⁵ and R ⁶ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R ⁵ and R ⁶ may be bonded to each other to form a ring.

^R5 and ^R6 may be the same or different, but it is preferred that ^R5 and ^R6 are the same.

The aromatic hydrocarbon group represented by R ⁵ or R ⁶ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The alkyl group represented by R ⁵ or R ⁶ preferably has 1 or more and 30 or less carbon atoms, more preferably has 1 or more and 15 or less carbon atoms, and particularly preferably has 1 or more and 10 or less carbon atoms.

Specific examples of the aromatic hydrocarbon group and alkyl group as ^R5 and ^R6 are the same as the specific examples of the aromatic hydrocarbon group and alkyl group given above for ^R1 and ^R2 , respectively, and therefore will not be described here. The aromatic hydrocarbon group or alkyl group as ^R5 may be bonded to the aromatic hydrocarbon group or alkyl group as ^R6 via a single bond.

In particular, from the viewpoint of further improving durability, ^R5 and ^R6 are each preferably independently a substituted or unsubstituted linear or branched alkyl group having from 1 to 10 carbon atoms, and more preferably a substituted or unsubstituted linear alkyl group having from 1 to 10 carbon atoms.

In the above formula (6), ^R7 and ^R8 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case ^R7 and ^R8 may be bonded to each other to form a ring.

The aromatic hydrocarbon group represented by R ⁷ and R ⁸ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The alkyl group represented by R ⁷ and R ⁸ preferably has 1 or more and 30 or less carbon atoms, more preferably has 1 or more and 15 or less carbon atoms, and particularly preferably has 1 or more and 10 or less carbon atoms.

Specific examples of the aromatic hydrocarbon group and alkyl group represented by ^R7 and ^R8 are the same as those given above for ^R1 and ^R2 , respectively, and therefore will not be described further. The aromatic hydrocarbon group or alkyl group represented by ^R7 may be bonded to the aromatic hydrocarbon group or alkyl group represented by ^R8 via a single bond.

In the above formula (6), c is 0, 1, 2, or 3, d is 0, 1, 2, 3, or 4, and when either c or d is 2 or more, each R ⁷ or each R ⁸ may be the same or different.

c and d respectively represent the number of ^R7 and ^R8 substituted on the ring-forming atoms contained in the structure of formula (6). When c or d is 0, it means that the corresponding ^R7 or ^R8 does not exist. That is, in the above formula (6), the ring-forming atom described so that the substituent ^R7 or ^R8 may be bonded thereto is unsubstituted, and a hydrogen atom is bonded to the ring-forming atom.

c is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. d is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.

Furthermore, from the viewpoints of improving durability and obtaining sufficient luminous efficiency, it is preferable that in the above formula (1), p is 1 and Ar ⁵ is a group represented by the above formula (5).

In this case, the group represented by the above formula (5) is preferably any of the groups represented by the following formulas (501) to (515):

In the above formulas (501) to (515), R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R ³⁰¹ and R ⁴⁰¹ , R 302 and R 402 , R ³⁰³ and R ⁴⁰³ , R ³⁰⁴ and R ⁴⁰⁴ , R ³⁰⁵ and R ⁴⁰⁵ , R ³⁰⁶ and R ⁴⁰⁶ , R ³⁰⁷ and R ⁴⁰⁷ , R ³⁰⁸ and R ⁴⁰⁸ , R ³⁰⁹ and R ⁴⁰⁹ , R ^{310 and} R ⁴¹⁰ , R ³¹¹ and R ⁴¹¹ , R ³¹² and R ⁴¹² , R ^{313 and} R ^{R 413} , R ³¹⁴ and R ⁴¹⁴ , and R ³¹⁵ and R ⁴¹⁵ may each be bonded to each other to form a ring.

In the above formulae (501) to (515), R ³⁰¹ to R ³¹⁵ each have the same definition as R ³ in the above formula (5), and R ⁴⁰¹ to R ⁴¹⁵ each have the same definition as R ⁴ in the above formula (5).

The aromatic hydrocarbon group represented by R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The alkyl groups represented by R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ preferably have 1 or more and 30 or less carbon atoms, more preferably have 1 or more and 15 or less carbon atoms, and particularly preferably have 1 or more and 10 or less carbon atoms.

Further, specific examples of the aromatic hydrocarbon groups and alkyl groups represented by R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ are similar to the specific examples of the aromatic hydrocarbon groups and alkyl groups given for R ¹ and R ² above, and therefore will not be described further. The aromatic hydrocarbon groups or alkyl groups represented by R ³⁰¹ to R ³¹⁵ may be bonded to the aromatic hydrocarbon groups or alkyl groups represented by R ⁴⁰¹ to R ⁴¹⁵ via single bonds.

In the above formulas (501) to (515), a1 to a15 each independently represent 0, 1, 2, or 3, b1 to b15 each independently represent 0, 1, 2, 3, or 4, and when any of a1 to a15 and b1 to b15 is 2 or more, each R ³⁰¹ , each R ³⁰² , each R ³⁰³ , each R ³⁰⁴ , each R ³⁰⁵ , each R ³⁰⁶ , each R ³⁰⁷ , each R ³⁰⁸ , each R ³⁰⁹ , each R ³¹⁰ , each R ³¹¹ , each R ³¹² , each R ³¹³ , each R ³¹⁴ , each R ³¹⁵ , each R ⁴⁰¹ , each R ⁴⁰² , each R ⁴⁰³ , each R ⁴⁰⁴ , each R ⁴⁰⁵ , each R ⁴⁰⁶ , each R ⁴⁰⁷ , each R ⁴⁰⁸ , each R ⁴⁰⁹ , each R ⁴¹⁰ , each R ⁴¹¹ , each R ⁴¹² , each R ⁴¹³ , each R ⁴¹⁴ , or each R ⁴¹⁵ may be the same or different.

In the above formulas (501) to (515), a1 to a15 and b1 to b15 respectively represent the numbers of R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ substituted on ring-forming atoms contained in the structures of formulas (501) to (515), a1 to a15 are 0, 1, 2, or 3, and b1 to b15 are 0, 1, 2, 3, or 4.

When a1, a2, a3, a4, a5, a6, a7, a8, a9, a10, a11, a12, a13, a14, or a15 is 0, it means that the corresponding R ³⁰¹ , R ³⁰² , R ³⁰³ , R ³⁰⁴ , R ³⁰⁵ , R ³⁰⁶ , R ³⁰⁷ , R ³⁰⁸ , R ³⁰⁹ , R ³¹⁰ , R ³¹¹ , R ³¹² , R ³¹³ , R ³¹⁴ , or R ³¹⁵ is not present. That is, in the above formulas (501) to (515), a ring-forming atom ^to which the substituent R ³⁰¹ , R ³⁰² , R ³⁰³ , R ³⁰⁴ , R ³⁰⁵ , R ³⁰⁶ , R ³⁰⁷ , R ³⁰⁸ , R ³⁰⁹ , R ³¹⁰ , R ³¹¹ , R ³¹² , R 313 , R ³¹⁴ or R ³¹⁵ may be bonded is unsubstituted, and a hydrogen atom is bonded to the ring-forming atom.

Similarly, when b1, b2, b3, b4, b5, b6, b7, b8, b9, b10, b11, b12, b13, b14, or b15 is 0, it means that the corresponding R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ , R ⁴¹¹ , R ⁴¹² , R ⁴¹³ , R ⁴¹⁴ , or R ⁴¹⁵ does not exist. That is, in the above formulas (501) to (515), the ring-forming atom ^to which the substituent R ⁴⁰¹ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ , R ⁴¹¹ , R ⁴¹² , R 413 , R ⁴¹⁴ or R ⁴¹⁵ may be bonded is unsubstituted, and a hydrogen atom is bonded to the ring-forming atom.

In addition, when any of a1 to a15 and b1 to b15 is 2 or more, each R ³⁰¹ , each R ³⁰² , each R ³⁰³ , each R ³⁰⁴ , each R ³⁰⁵ , each R ³⁰⁶ , each R ³⁰⁷ , each R ³⁰⁸ , each R ³⁰⁹ , each R ³¹⁰ , each R ³¹¹ , each R ³¹² , each R ³¹³ , each R ³¹⁴ , each R ³¹⁵ , each R ⁴⁰¹ , each R ⁴⁰² , each R ⁴⁰³ , each R ⁴⁰⁴ , each R ⁴⁰⁵ , each R ⁴⁰⁶ , each R ⁴⁰⁷ , each R ⁴⁰⁸ , each R ⁴⁰⁹ , each R ⁴¹⁰ , each R ⁴¹¹ , each R ⁴¹² and each R ⁴¹³ , each R ⁴¹⁴ , or each R ⁴¹⁵ may be the same or different.

Each of a1 to a15 is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. Each of b1 to b15 is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.

In the above formulas (504) to (507), R ⁵⁰⁴ to R ⁵⁰⁷ and R ⁶⁰⁴ to R ⁶⁰⁷ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R ⁵⁰⁴ and R ⁶⁰⁴ , R ⁵⁰⁵ and R ⁶⁰⁵ , R ⁵⁰⁶ and R ⁶⁰⁶ , and R ⁵⁰⁷ and R ⁶⁰⁷ may each be bonded to each other to form a ring.

In the above formulae (504) to (507), R ⁵⁰⁴ to R ⁵⁰⁷ each have the same definition as R ⁵ in the above formula (5), and R ⁶⁰⁴ to R ⁶⁰⁷ each have the same definition as R ⁶ in the above formula (5).

R ⁵⁰⁴ and R ⁶⁰⁴ , R ⁵⁰⁵ and R ⁶⁰⁵ , R ⁵⁰⁶ and R ⁶⁰⁶ , and R ⁵⁰⁷ and R ⁶⁰⁷ may be the same or different, but it is preferred that R ⁵⁰⁴ and R ⁶⁰⁴ , R ⁵⁰⁵ and R ⁶⁰⁵ , R ⁵⁰⁶ and R ⁶⁰⁶ , and R ⁵⁰⁷ and R ⁶⁰⁷ are the same.

The aromatic hydrocarbon group represented by R ⁵⁰⁴ to R ⁵⁰⁷ and R ⁶⁰⁴ to R ⁶⁰⁷ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The number of carbon atoms in the alkyl groups represented by R ⁵⁰⁴ to R ⁵⁰⁷ and R ⁶⁰⁴ to R ⁶⁰⁷ is preferably 1 to 30, more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 3.

Specific examples of the aromatic hydrocarbon groups and alkyl groups represented by ^R504 to ^R507 and ^R604 to ^R607 are similar to the specific examples of the aromatic hydrocarbon groups and alkyl groups given above for ^R1 and ^R2 , and therefore will not be described further. The aromatic hydrocarbon groups or alkyl groups represented by ^R504 to ^R507 may be bonded to the aromatic hydrocarbon groups or alkyl groups represented by ^R604 to ^R607 via single bonds.

In particular, from the viewpoints of further improving durability and obtaining sufficient luminous efficiency, R ⁵⁰⁴ to R ⁵⁰⁷ and R ⁶⁰⁴ to R ⁶⁰⁷ are each preferably independently a substituted or unsubstituted linear or branched alkyl group having from 1 to 10 carbon atoms, more preferably a substituted or unsubstituted linear alkyl group having from 1 to 10 carbon atoms, and particularly preferably a substituted or unsubstituted linear alkyl group having from 1 to 3 carbon atoms.

Among the above, the group represented by the formula (5) is preferably any of the groups represented by the formulas (504) to (507) and the formulas (512) to (515). That is, in the formula (1), it is preferable that p is 1 and Ar ⁵ is any of the groups represented by the formulas (504) to (507) and the formulas (512) to (515).

<<Preferred form of structural unit X>>
In the above formula (1), preferred forms of the structural unit X are those in which Ar ¹ to Ar ³ are any of the groups represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar ⁴ is a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group, when p is 0, Ar ⁴ is a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthrenyl group, and when p is 1, Ar ⁵ is any of the groups represented by the above formulas (504) to (507) and (512) to (515). In a more preferred embodiment, Ar ¹ and Ar ² are groups represented by the above formula (2), Ar ³ is any of the groups represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar ⁴ is a substituted or unsubstituted anthracenylene group, or a substituted or unsubstituted phenanthrenylene group, when p is 0, Ar ⁴ is a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthrenyl group, and when p is 1, Ar ⁵ is any of the groups represented by the above formulas (504) to (507) and (512) to (515). In a particularly preferred embodiment, Ar ¹ and Ar ² are groups represented by the above formula (2), Ar ³ is a group represented by the above formula (2) or (3), p is 0 or 1, and when p is 1, Ar ⁴ is an unsubstituted anthracenylene group or an unsubstituted phenanthrenylene group, when p is 0, Ar ⁴ is an unsubstituted anthracenyl group or an unsubstituted phenanthrenyl group, and when p is 1, Ar ⁵ is any of groups represented by the above formulas (504) to (507) and (512) to (515), and in the above formulas (504) to (507) and (512) to (515), a4 to a7, a12 to a15, b4 to b7, and b12 to b15 are 0.

The polymer having the structural unit X as described above has excellent durability due to the resonance stabilization effect of ^Ar4 . In addition, the polymer having the above structure has a deep HOMO level (hence, the luminous efficiency of an LED (particularly a QLED) using the polymer according to one embodiment of the present invention can be improved).

Preferred examples of the structural unit X according to the present invention include the following structures:

In the above structural formula, the group represented by "-C _n H _2n+1 (where n is a natural number)" represents a straight-chain alkyl group. Also, * represents a bonding site forming the main chain. The same applies to structural formulas described in this specification unless otherwise specified.

In particular, the structural unit X is preferably selected from the above structures (X-a1-1) to (X-a1-12), (X-a2-1) to (X-a2-12), (X-a3-1) to (X-a3-12), (X-a5-1) to (X-a5-12), and (X-o4-1) to (X-o4-9).

Particularly preferred examples of the structural unit X according to the present invention include the following structures (X-1) to (X-8). The following structures (X-1) to (X-8) are the same as the above structure (X-a1-5).
, (X-a1-1), (X-a2-1), (X-a1-2), (X-a3-5), (X-a3-2), (X-a5-5), and (X-o4-1), respectively.

In the above formula (1), Ar ⁶ (i.e., the structural unit Y) constitutes a polymer according to one embodiment of the present invention in addition to the above structural unit X, and represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 60 ring atoms.

The aromatic hydrocarbon group and aromatic heterocyclic group as Ar ⁶ may be a single ring or a condensed ring. Specific examples of the divalent aromatic hydrocarbon group having 6 to 60 ring atoms are the same as the divalent groups derived from aromatic hydrocarbon compounds exemplified for Ar ¹ to Ar ³ above, and therefore the description will be omitted. Specific examples of the divalent aromatic heterocyclic group having 5 to 60 ring atoms are those obtained by converting the monovalent groups derived from aromatic heterocyclic compounds exemplified for Ar ⁵ above into divalent groups.

^Ar6 is preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 30 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 30 ring atoms, and more preferably a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 ring atoms or a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 20 ring atoms.

Of these, Ar ⁶ is preferably selected from the groups represented by the following formulas (7) to (22). That is, in a preferred embodiment of the present invention, in the above formula (1), Ar ⁶ is any of the groups represented by the following formulas (7) to (22):

In the above formulas (7) to (22),
R ⁹ to R ³⁵ each independently represent a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 5 to 60 ring atoms, an alkyl group having 1 to 60 carbon atoms, or a hydrogen atom. In this case, R ⁹ to R ³⁵ may be the same or different.

The aromatic hydrocarbon group and aromatic heterocyclic group as R ⁹ to R ³⁵ may each be a monocyclic ring or a condensed ring. Specific examples of the monovalent aromatic hydrocarbon group having 6 to 60 ring atoms include the divalent groups derived from the aromatic hydrocarbon compounds exemplified for Ar ¹ to Ar ³ above, which are converted to monovalent groups. Specific examples of the monovalent aromatic heterocyclic group having 5 to 60 ring atoms are the same as the specific examples of the aromatic heterocyclic group exemplified for Ar ⁵ above, and therefore the explanation is omitted. Specific examples of the alkyl group having 1 to 60 carbon atoms are the same as the specific examples of the alkyl group exemplified for R ¹ and R ² above, and therefore the explanation is omitted.

The aromatic hydrocarbon group represented by R ⁹ to R ³⁵ preferably has 6 or more and 20 or less ring atoms, more preferably has 6 or more and 15 or less ring atoms, and particularly preferably has 6 or more and 10 or less ring atoms.

The aromatic heterocyclic group represented by R ⁹ to R ³⁵ preferably has 6 or more and 30 or less ring atoms, more preferably has 6 or more and 20 or less ring atoms, and particularly preferably has 10 or more and 15 or less ring atoms.

The alkyl group represented by R ⁹ to R ³⁵ preferably has 1 or more and 30 or less carbon atoms, more preferably has 3 or more and 20 or less carbon atoms, and particularly preferably has 5 or more and 15 or less carbon atoms.

Among these, R ⁹ to R ³⁵ are preferably each independently a group selected from the group consisting of a substituted or unsubstituted monovalent aromatic heterocyclic group having from 10 to 15 ring atoms, a linear alkyl group having from 3 to 20 carbon atoms, a branched alkyl group having from 3 to 20 carbon atoms, and a hydrogen atom, and more preferably a group selected from the group consisting of a substituted or unsubstituted monovalent aromatic heterocyclic group having from 10 to 15 ring atoms, a linear alkyl group having from 5 to 15 carbon atoms, and a hydrogen atom.

Furthermore, the aromatic heterocyclic group, which is a preferred embodiment of R ⁹ to R ³⁵ , is preferably substituted, and is particularly preferably substituted with an alkyl group, a cycloalkyl group, an aryl group, or a combination thereof.

In the above formulas (7) to (22), Q ¹ to Q ⁹ each independently represent -O-, -S-, -Se-, -CR ³⁶ R ³⁷ -, or -SiR ³⁸ R ³⁹ -, where R ³⁶ to R ³⁹ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R ³⁶ and R ³⁷ may be the same or different, but it is preferable that R ³⁶ and R ³⁷ are the same. Similarly, R ³⁸ and R ³⁹ may be the same or different, but it is preferable that R ³⁸ and R ³⁹ are the same.

Here, the alkyl group and the aryl group are the same as the specific examples of the alkyl group and the aromatic hydrocarbon group given for R ¹ and R ^2, respectively, and therefore the explanation will be omitted. Examples of the heteroaryl group include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a 2-carbazol ...1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 5-indolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a 2-carbazolyl group, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 5-indolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a -carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, and 10-phenoxazinyl group.

The alkyl group represented by R ³⁶ and R ³⁷ preferably has 1 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 5 to 15 carbon atoms, and most preferably 10 to 13 carbon atoms.

The aryl group represented by R ³⁶ and R ³⁷ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

The heteroaryl group represented by R ³⁶ and R ³⁷ preferably has 6 or more and 20 or less ring atoms, more preferably 6 or more and 15 or less ring atoms, and particularly preferably 6 or more and 10 or less ring atoms.

In the above formulas (7) to (22), Z ¹ to Z ⁷ each independently represent -CR ⁴⁰ =, -N=, or -SiR ⁴¹ =, where R ⁴⁰ and R ⁴¹ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R ⁴⁰ and R ⁴¹ may be the same or different.

Here, the alkyl group and the aryl group are the same as the specific examples of the alkyl group and the aromatic hydrocarbon group exemplified for R ¹ and R ² above, respectively, and therefore the explanation is omitted. In addition, the heteroaryl group is exemplified by the same heteroaryl groups as those exemplified in the explanation of R ³⁶ and R ³⁷ above.

In the above formulas (7) to (22), * represents a bonding site that forms the main chain.

<<Preferred form of structural unit Y>>
In the above formula (1), preferred forms of the structural unit Y (i.e., Ar ⁶ ) are groups represented by formulas (7) to (9), in which R ⁹ to R ¹¹ are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group having from 6 to 30 ring carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having from 5 to 30 ring atoms, a straight-chain or branched alkyl group having from 1 to 30 carbon atoms, or a hydrogen atom; and Q ¹ represents -CR ³⁶ R ³⁷ -, in which R ³⁶ and R ³⁷ are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group having from 6 to 30 ring carbon atoms, a straight-chain or branched alkyl group having from 1 to 30 carbon atoms, or a hydrogen atom. More preferably, Ar ⁶ is a group represented by formula (7) to (9), in which R ⁹ to R ¹¹ are each independently a substituted or unsubstituted monovalent aromatic heterocyclic group having from 10 to 15 ring atoms, a linear or branched alkyl group having from 5 to 15 carbon atoms, or a hydrogen atom, and Q ¹ is -CR ³⁶ R ³⁷ -, in which R ³⁶ and R ³⁷ are each independently a substituted or unsubstituted linear or branched alkyl group having from 5 to 15 carbon atoms. Particularly preferably, Ar ⁶ is a group represented by formula (7) to (9), in which R ⁹ to R ¹¹ are each independently a substituted or unsubstituted monovalent aromatic heterocyclic group having from 10 to 15 ring atoms, a linear or branched alkyl group having from 5 to 15 carbon atoms, or a hydrogen atom, and Q ¹ is -CR ³⁶ R ³⁷ -, in which R ³⁶ and R ³⁷ are each independently a substituted or unsubstituted linear or branched alkyl group having from 10 to 13 carbon atoms.

In the polymer having the structural unit Y as described above, the resonance stabilization effect of ^Ar4 is more likely to spread throughout the entire molecule, and durability is further improved. In addition, the polymer having the above structure has a deep HOMO level (hence, the luminous efficiency of an LED (particularly a QLED) using the polymer according to one embodiment of the present invention can be improved).

Particularly preferred examples of the structural unit Y according to the present invention include the following structures (Y-1) to (Y-4).

<<Preferred Form of Structural Unit (A)>>
In view of the above, particularly preferred forms of the structural unit (A) constituting the polymer of the present invention include the following. That is, the structural unit (A) represented by the above formula (1) is preferably any one of the structural units represented by the following formulas (A-1) to (A-11):

The polymer according to one embodiment of the present invention essentially contains the structural unit X and the structural unit Y, but may have other structural units in addition to these structural units X and Y. Here, examples of the other structural units include structural units derived from compounds such as azulene, naphthalene, and anthracene. Here, when the polymer according to one embodiment of the present invention has other structural units, the composition of the other structural units is not particularly limited. Considering the durability and HOMO level of the polymer (hence, the effect of improving the hole transport ability and luminous efficiency of a layer (e.g., hole injection layer, hole transport layer) formed using the polymer), the other structural units are preferably more than 0 mol% and less than 15 mol%, more preferably 0.5 mol% or more and 10 mol% or less, based on the total structural units constituting the polymer. In addition, when the polymer contains two or more types of other structural units, the content of the other structural units means the total amount of the other structural units.

The weight average molecular weight (Mw) of the polymer according to one embodiment of the present invention is not particularly limited as long as the intended effect of the present invention is obtained. The weight average molecular weight (Mw) is, for example, preferably 5,000 to 1,000,000, more preferably 8,000 to 500,000, and particularly preferably 10,000 to 250,000. With such a weight average molecular weight, it is possible to appropriately adjust the viscosity of the coating solution for forming a layer (e.g., a hole injection layer, a hole transport layer) using the polymer to form a layer with a uniform thickness.

The number average molecular weight (Mn) of the polymer is not particularly limited as long as the objective effect of the present invention can be obtained.
It is preferable that the number average molecular weight is 5,000 or less, more preferably 5,000 or more and 300,000 or less, and particularly preferably 8,000 or more and 100,000 or less. With such a number average molecular weight, it is possible to appropriately adjust the viscosity of a coating solution for forming a layer (e.g., a hole injection layer, a hole transport layer) using the polymer to form a layer with a uniform thickness. In addition, the polydispersity (weight average molecular weight/number average molecular weight) of the polymer of this embodiment is, for example, 1.10 or more and 15.0 or less, preferably 1.30 or more and 13.0 or less, and more preferably 1.50 or more and 5.00 or less.

Here, the number average molecular weight (Mn) and weight average molecular weight (Mw) can be measured without any particular limitations, and known methods can be used or known methods can be appropriately modified. In this specification, the number average molecular weight (Mn) and weight average molecular weight (Mw) are values measured by the following method. The polydispersity (Mw/Mn) of a polymer is calculated by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn) measured by the following method.

(Measurement of number average molecular weight (Mn) and weight average molecular weight (Mw))
The number average molecular weight (Mn) and weight average molecular weight (Mw) of a polymer are measured by SEC (Size Exclusion Chromatography) using polystyrene as a standard substance under the following conditions.

The end of the main chain of the polymer according to one embodiment of the present invention is not particularly limited and is determined appropriately depending on the type of raw material used, but is usually a hydrogen atom.

The polymer according to one embodiment of the present invention can be synthesized by using a known organic synthesis method. A person skilled in the art can easily understand the specific synthesis method of the polymer according to one embodiment of the present invention by referring to the examples described below. Specifically, it can be produced by a copolymerization reaction using one or more monomers (X) represented by the following formula (X') and one or more monomers (Y) represented by the following formula (Y'). In this case, if necessary, other monomers corresponding to the other structural units may be further added.

Alternatively, the polymer according to one embodiment of the present invention can be produced by a polymerization reaction using one or more monomers (A) represented by the following formula (A'). In addition, at this time, if necessary, other monomers corresponding to the other structural units may be further added.

The monomers used in the polymerization of the polymer according to one embodiment of the present invention can be synthesized by appropriately combining known synthesis reactions, and their structures can be confirmed by known methods (e.g., NMR, LC-MS, etc.).

In the above formulae (X'), (Y') and (A'), Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ and p, and Ar ⁶ are respectively defined as in the above formula (1). In addition, in the above formulae (X'), (Y') and (A'), Z ¹ and Z ² , Z ^1' and Z ^2' , and Z ^1" and Z ^2" are each independently a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, in particular a bromine atom) or a group of the following structure. In the following structure, R ^A to R ^D are each independently an alkyl group having 1 to 3 carbon atoms. Preferably, R ^A to R ^D are a methyl group. In addition, Z ¹ and Z ² in the above formula (X'), Z ^1' and Z ^2' in the above formula (Y'), and Z ^1" and Z ^2" in the above formula (A') may be the same or different. However, in order to suppress polymerization of monomers (X) with each other, Z ¹ and Z ² in the above formula (X') are preferably atoms or groups that do not react with each other. Similarly, in order to suppress polymerization of monomers (B) with each other, Z ^1' and Z ² in the above formula (Y') are preferably atoms or groups that do not react with each other. Preferably, Z ¹ and Z ² in the above formula (X'), and Z ^1' and Z ^2' in the above formula (Y') are the same. Also, preferably, Z ^1" and Z ^2" in the above formula (A') are different.

The polymer according to one embodiment of the present invention has a structural unit X and a structural unit Y. Therefore, the polymer has a deep HOMO level. Therefore, when the polymer according to one embodiment of the present invention is used as a hole injection material or a hole transport material (particularly a hole transport material), good luminous efficiency can be achieved.

Specifically, the HOMO level of the polymer according to one embodiment of the present invention is not particularly limited, but is, for example, -5.8 eV or more and -5.5 eV or less. Since the polymer has such a deep HOMO level, in particular in a quantum dot electroluminescence device having a hole transport layer containing the polymer according to one embodiment of the present invention and a light emitting layer containing quantum dots, the band offset (barrier) between the hole transport layer and the light emitting layer is small, and the transport ability of holes (holes) from the hole transport layer to the light emitting layer can be improved. Therefore, by using the polymer according to one embodiment of the present invention, an electroluminescence device (particularly a QLED) exhibiting good light emitting efficiency can be provided.

The glass transition temperature (Tg) of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably 60°C or higher, more preferably 80°C or higher, particularly preferably 90°C or higher, and most preferably 100°C or higher. On the other hand, the upper limit is also not particularly limited, but is preferably 250°C or lower, more preferably 240°C or lower, and particularly preferably 230°C or lower.

When the glass transition temperature (Tg) of the polymer is within the above range, it is suitable for device fabrication, and devices with improved characteristics can be obtained. The glass transition temperature (Tg) of the polymer can be measured using a differential scanning calorimeter (DSC) (Seiko Instruments Inc., product name: DSC6000). Details of the measurement method are described in the examples.

[Electroluminescence Device Materials]
The polymer according to one embodiment of the present invention is preferably used as an electroluminescence device material. According to this aspect, an electroluminescence device material having excellent durability (luminescence life) is provided. Furthermore, according to the polymer according to one embodiment of the present invention, an electroluminescence device material having good luminescence efficiency is also provided. Thus, according to a second aspect of the present invention, an electroluminescence device material containing the polymer of the present invention is provided. Alternatively, use of the polymer according to one embodiment of the present invention as an electroluminescence device material is provided.

In addition, the polymer according to one embodiment of the present invention has a deep HOMO level of -5.5 eV or less. Therefore, the polymer according to one embodiment of the present invention can be suitably used in quantum dot electroluminescence devices (particularly hole transport layers).

[Electroluminescence element]
As described above, the polymer according to one embodiment of the present invention is preferably used in an electroluminescence device. That is, an electroluminescence device is provided that includes a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer or electroluminescence device material according to one embodiment of the present invention. Such an electroluminescence device can exhibit excellent durability (light-emitting life). In addition, the electroluminescence device can exhibit good light-emitting efficiency (particularly good light-emitting efficiency at a low driving voltage). Therefore, according to a third aspect of the present invention, an electroluminescence device is provided that includes a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein at least one layer of the organic film contains the polymer of the present invention. The object (or effect) of the present invention can also be achieved by the electroluminescence device according to such an embodiment. As a preferred embodiment of the above aspect, the electroluminescence device further includes a light-emitting layer disposed between the electrodes and containing a light-emitting material capable of emitting light from triplet excitons. The electroluminescent element of this embodiment is an example of the electroluminescent element according to the present invention.

Furthermore, one embodiment of the present invention provides a method for producing an electroluminescence device comprising a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer of the present invention, wherein at least one of the organic films is formed by a coating method. By using such a method, one embodiment of the present invention also provides an electroluminescence device in which at least one of the organic films is formed by a coating method.

The polymer of one embodiment of the present invention and the electroluminescence element material (EL element material) of one embodiment of the present invention (hereinafter collectively referred to as "polymer/EL element material") also have good solubility in organic solvents. For this reason, the polymer/EL element material of one embodiment of the present invention is particularly suitable for use in the manufacture of elements (particularly thin films) by a coating method (wet process). For this reason, one embodiment of the present invention provides a liquid composition containing the polymer of the present invention and a solvent or dispersion medium. The liquid composition of this embodiment is an example of a liquid composition according to the present invention.

As described above, the electroluminescent device material according to the embodiment is preferably used for manufacturing devices (particularly thin films) by a coating method (wet process). From the above viewpoint, one embodiment of the present invention provides a thin film containing the polymer of the present invention. The thin film of the present embodiment is an example of the thin film according to the present invention.

The EL element material according to one embodiment of the present invention has excellent hole injection properties and hole mobility. Therefore, it can be suitably used in the formation of any organic film such as a hole injection material, a hole transport material, or a light-emitting material (host). Among these, from the viewpoint of hole transport properties, it is suitably used as a hole injection material or a hole transport material, and is particularly suitably used as a hole transport material.

That is, one embodiment of the present invention provides a composition containing a polymer and at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material. Here, the light emitting material contained in the composition is not particularly limited, but may contain an organometallic complex (a light emitting organometallic complex compound) or a semiconductor nanoparticle (a semiconductor inorganic nanoparticle).

The electroluminescent element according to one embodiment of the present invention will be described in detail below with reference to FIG. 1. FIG. 1 is a schematic diagram showing an electroluminescent element according to one embodiment of the present invention. Note that in this specification, "electroluminescent element" may be abbreviated to "EL element."

As shown in FIG. 1, an EL element 100 according to one embodiment of the present invention includes a substrate 110, a first electrode 120 disposed on the substrate 110, a hole injection layer 130 disposed on the first electrode 120, a hole transport layer 140 disposed on the hole injection layer 130, a light emitting layer 150 disposed on the hole transport layer 140, an electron transport layer 160 disposed on the light emitting layer 150, an electron injection layer 170 disposed on the electron transport layer 160, and a second electrode 180 disposed on the electron injection layer 170.

Here, the polymer/EL element material of this embodiment is, for example, contained in any of the organic films (organic layers) arranged between the first electrode 120 and the second electrode 180. Specifically, the polymer/EL element material is preferably contained in the hole injection layer 130 as a hole injection material, the hole transport layer 140 as a hole transport material, or the light emitting layer 150 as a light emitting material (host). It is more preferable that the polymer/EL element material is contained in the hole injection layer 130 as a hole injection material or in the hole transport layer 140 as a hole transport material. It is particularly preferable that the polymer/EL element material is contained in the hole transport layer 140 as a hole transport material. That is, in a preferred embodiment of the present invention, the organic film containing the polymer/EL element material is a hole transport layer, a hole injection layer, or a light emitting layer. In a more preferred embodiment of the present invention, the organic film containing the polymer is a hole transport layer or a hole injection layer. In a particularly preferred embodiment of the present invention, the organic film containing the polymer is a hole transport layer.

The organic film containing the polymer/EL element material of this embodiment is formed by a coating method (solution coating method). Specifically, the organic film can be formed by a spin coat method, a casting method, a micro gravure coat method, a gravure coat method, a bar coat method, a roll coat method, a wire bar coat method, a dip coat method, a spray coat method, a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, or a combination of these methods.
The film is formed by using a solution coating method such as a liquid jet printing method.

In addition, the solvent used in the solution coating method can be any solvent that can dissolve the polymer/EL element material, and can be appropriately selected depending on the type of polymer used. Examples include toluene, xylene, ethylbenzene, diethylbenzene, methylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, cyclohexane, and the like. The amount of solvent used is not particularly limited, but considering ease of coating, the amount is preferably such that the concentration of the polymer is about 0.1% by mass to 10% by mass, more preferably 0.5% by mass to 5% by mass.

The method for forming layers other than the organic film containing the polymer/EL element material is not particularly limited. The layers other than the organic film containing the polymer/EL element material of this embodiment may be formed, for example, by a vacuum deposition method or a solution coating method.

The substrate 110 may be a substrate used in a general EL device. For example, the substrate 110 may be a glass substrate, a semiconductor substrate such as a silicon substrate, or a transparent plastic substrate.

A first electrode 120 is formed on the substrate 110. Specifically, the first electrode 120 is an anode, and is formed of a metal, an alloy, or a conductive compound having a large work function. For example, the first electrode 120 may be formed as a transmissive electrode using indium tin oxide (In ₂ O ₃ -SnO ₂ :ITO), indium zinc oxide (In ₂ O ₃ -ZnO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like, which are excellent in transparency and conductivity. The first electrode 120 may also be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), or the like on the transparent conductive film. After the first electrode 120 is formed on the substrate 110, cleaning and UV-ozone treatment may be performed, if necessary.

A hole injection layer 130 is formed on the first electrode 120. The hole injection layer 130 is a layer that facilitates the injection of holes from the first electrode 120, and may be formed to a thickness (dry film thickness; the same applies below) of about 10 nm to about 1000 nm, more specifically, about 20 nm to about 50 nm.

The hole injection layer 130 can be formed of a known hole injection material. Examples of known hole injection materials for forming the hole injection layer 130 include poly(ether ketone)-containg triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine (copper phthalocyanine), and phthalocyanine. phthalocyanine), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), 4,4',4"-tris(diphenylamino)triphenylamine (TDATA), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline/dodecylbenzenesulphonic acid acid), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), and polyaniline/10-camphorsulfonic acid.

On the hole injection layer 130, a hole transport layer 140 is formed. The hole transport layer 140 is a layer having a function of transporting holes, and may be formed, for example, with a thickness of about 10 nm to about 150 nm, more specifically, about 20 nm to about 50 nm. The hole transport layer 140 is preferably formed by a solution coating method using the polymer of one embodiment of the present invention. According to this method, it is possible to extend the durability (light emission life) of the EL element 100. In addition, the performance (light emission efficiency) of the EL element 100 can be improved. Furthermore, since the hole transport layer can be formed by the solution coating method, it can be efficiently formed over a large area.

However, when any other organic film of the EL element 100 contains the polymer of one embodiment of the present invention, the hole transport layer 140 may be formed of a known hole transport material. Examples of known hole transport materials include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole, and polyvinylcarbazole.
carbazole derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4
Examples of such an alkylating agent include 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), and N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB).

The light-emitting layer 150 is formed on the hole transport layer 140. The light-emitting layer 150 is a layer that emits light by fluorescence, phosphorescence, or the like, and is formed by using a vacuum deposition method, a spin coating method, an inkjet printing method, or the like. The light-emitting layer 150 may be formed to a thickness of, for example, about 10 nm to about 60 nm, more specifically, about 20 nm to about 50 nm. As the light-emitting material of 150, a known light-emitting material can be used. However, it is preferable that the light-emitting material contained in the light-emitting layer 150 is a light-emitting material that can emit light from triplet excitons (i.e., phosphorescence emission). In such a case, the operating life of the EL element 100 can be further improved.

The light-emitting layer 150 is not particularly limited and may have a known configuration. Preferably, the light-emitting layer contains semiconductor nanoparticles or an organometallic complex. That is, in a preferred embodiment of the present invention, the organic film has a light-emitting layer containing semiconductor nanoparticles or an organometallic complex. When the light-emitting layer contains semiconductor nanoparticles, the EL element is a quantum dot electroluminescent element (QLED), a quantum dot light-emitting element, or a quantum dot light-emitting element. When the light-emitting layer contains an organometallic complex, the EL element is an organic electroluminescent element (OLED).

In a configuration in which the light-emitting layer contains semiconductor nanoparticles (QLED), the light-emitting layer is a single layer or multiple layers of a large number of semiconductor nanoparticles (quantum dots). Here, the semiconductor nanoparticles (quantum dots) are particles of a certain size that have a quantum confinement effect. The diameter of the semiconductor nanoparticles (quantum dots) is not particularly limited, but is about 1 nm or more and 20 nm or less.

The semiconductor nanoparticles (quantum dots) arranged in the light-emitting layer can be synthesized by wet chemical processes, metalorganic chemical vapor deposition processes, molecular beam epitaxy processes, or other similar processes. Among them, the wet chemical process is a method in which precursor materials are placed in an organic solvent to grow particles.

In the wet chemical process, the organic solvent naturally coordinates with the surface of the quantum dot crystal during crystal growth and acts as a dispersant to regulate the crystal growth. Therefore, the wet chemical process can control the growth of semiconductor nanoparticles more easily and at lower cost than gas phase deposition methods such as metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE).

By adjusting the size of semiconductor nanoparticles (quantum dots), the energy band gap can be adjusted, and light of various wavelengths can be obtained in the light-emitting layer (quantum dot light-emitting layer). Therefore, the use of multiple quantum dots of different sizes enables displays that emit (or emit) light of multiple wavelengths. The sizes of the quantum dots can be selected to emit red, green, and blue light to form a color display. The sizes of the quantum dots can also be combined to emit various color lights to emit white light.

As semiconductor nanoparticles (quantum dots), semiconductor materials selected from the group consisting of II-VI group semiconductor compounds; III-V group semiconductor compounds; IV-VI group semiconductor compounds; IV group elements or compounds; and combinations thereof can be used.

The II-VI group semiconductor compound is not particularly limited, but may be, for example, a bi-element compound selected from the group consisting of CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnTeSe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS , ternary compounds selected from the group consisting of CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, and mixtures thereof; and quaternary compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

The III-V group semiconductor compound is not particularly limited, and examples thereof include two-element compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; three-element compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures thereof; and GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAl
The quaternary compounds are selected from the group consisting of NAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof.

The IV-VI semiconductor compound is not particularly limited, but may be selected from the group consisting of two-element compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; three-element compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and four-element compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

The Group IV element or compound is not particularly limited, but may be selected from the group consisting of mono-element compounds selected from the group consisting of Si, Ge, and mixtures thereof; and bi-element compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

Semiconductor nanoparticles (quantum dots) can have a homogeneous single structure or a core-shell dual structure. The core and shell can contain different materials. The materials constituting each of the core and shell can be made of different semiconductor compounds. However, the energy band gap of the shell material is larger than the energy band gap of the core material. Specifically, structures such as ZnTeSe/ZnSe/ZnS, InP/ZnSe/ZnS, CdSe/ZnS, and InP/ZnS are preferred.

For example, a case of producing a quantum dot having a core (CdSe)-shell (ZnS) structure will be described. First, a precursor material of the core (CdSe), such as (CH ₃ ) ₂ Cd (dimethylcadmium) or TOPSe (trioctylphosphine selenide), is injected into an organic solvent using TOPO (trioctylphosphine oxide) as a surfactant to generate a crystal. At this time, after maintaining the crystal at a high temperature for a certain time so that it grows to a certain size, a precursor material of the shell (ZnS) is injected to form a shell on the surface of the already generated core. In this way, a quantum dot of CdSe/ZnS capped with TOPO can be produced.

In the case of an OLED in which the light-emitting layer contains an organic metal complex, the light-emitting layer 150 may contain, as a host material, for example, 6,9-diphenyl-9'-(5'-phenyl-[1,1':3',1"-terphenyl]-3-yl)-3,3'-bi[9H-carbazole], 3,9-diphenyl-5-(3-(4-phenyl-6-(5'-phenyl-[1,1':3',1"-terphenyl]-3-yl)-1,3,5,-triazine-2-yl )phenyl)-9H-carbazole, 9,9'-diphenyl-3,3'-bi[9H-carbazole], tris(8-quinolinato)aluminium (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinyl carbazole) (PVK)
), 9,10-di(naphthalene)anthracene (ADN), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphth-2-yl)
Anthracene (3-tert-butyl-9,10-di(naphth-2-yl)anthracene: TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazole)-
2,2'-dimethyl-biphenyl (4,4'-bis(9-carbazole)2,2'-dimethyl-biphenyl: dmCBP) may be included.

The light-emitting layer 150 may contain, as a dopant material, for example, perylene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2-(pdimethylaminostyryl)-6-methyl-4H-pyran (DC
The light-emitting material may include iridium (Ir) complexes such as bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III):FIrpic, bis(1-phenylisoquinoline)(acetylacetonate)iridium(III):Ir(piq) ₂ (acac), tris(2-phenylpyridine)iridium(III):Ir(ppy) ₃ , and tris(2-(3-p-oxyyl)phenyl)pyridineiridium(III), osmium (Os) complexes, and platinum complexes. Of these, it is preferable that the light-emitting material is a light-emitting organic metal complex compound.

There are no particular limitations on the method for forming the light-emitting layer. It can be formed by applying a coating liquid containing semiconductor nanoparticles or an organometallic complex (solution coating method). In this case, it is preferable to select a solvent that does not dissolve the material in the hole transport layer (hole transport material, particularly a polymer) as the solvent constituting the coating liquid.

An electron transport layer 160 is formed on the light-emitting layer 150. The electron transport layer 160 is a layer that has the function of transporting electrons, and is formed using a vacuum deposition method, a spin coating method, an inkjet method, or the like. The electron transport layer 160 may be formed to a thickness of, for example, about 15 nm or more and about 50 nm or less.

The electron transport layer 160 may be formed of a known electron transport material, such as (8-quinolinolato)lithium (lithium quinolate) (Liq), tris(8-quinolinolato)aluminum (Alq ₃ ), and a compound having a nitrogen-containing aromatic ring. Specific examples of the compound having a nitrogen-containing aromatic ring include a compound containing a pyridine ring such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, a compound containing a triazine ring such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, and a compound containing a 2-(4-(N-phenylbenzoimidazolyl-1-yl-phenyl)-9,10-dinaphthylanthracene).
and compounds containing an imidazole ring such as 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI). The above electron transport materials may be used alone or as a mixture of two or more kinds.

An electron injection layer 170 is formed on the electron transport layer 160. The electron injection layer 170 is a layer having a function of facilitating the injection of electrons from the second electrode 180. The electron injection layer 170 is formed by using a vacuum deposition method or the like. The electron injection layer 170 may be formed to a thickness of about 0.1 nm or more and about 5 nm or less, more specifically, about 0.3 nm or more and about 2 nm or less. Any material known as a material for forming the electron injection layer 170 can be used. For example, the electron injection layer 170 may be formed of a lithium compound such as (8-quinolinolato)lithium (lithium quinolate) ((8-quinolinato)lithium: Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li ₂ O), barium oxide (BaO), or the like.

A second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is formed by using a vacuum deposition method or the like. The second electrode 180 is specifically a cathode, and is formed of a metal, an alloy, or a conductive compound having a small work function. For example, the second electrode 180 may be formed as a reflective electrode using a metal such as lithium (Li), magnesium (Mg), aluminum (Al), or calcium (Ca), or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). The second electrode 180 may be formed to a thickness of about 10 nm to about 200 nm, more specifically, about 50 nm to about 150 nm. Alternatively, the second electrode 180 may be formed as a transmissive electrode using a transparent conductive film such as a thin film of the above metal materials having a thickness of 20 nm or less, indium tin oxide (In ₂ O ₃ —SnO ₂ ), indium zinc oxide (In ₂ O ₃ —ZnO), or the like.

The EL element 100 according to this embodiment has been described above as an example of an electroluminescence element according to one embodiment of the present invention. The EL element 100 according to this embodiment can further improve its durability (light-emitting life) by providing an organic film (particularly a hole transport layer or a hole injection layer) containing a polymer according to one embodiment of the present invention. Furthermore, the above configuration makes it possible to obtain good light-emitting efficiency.

The layered structure of the EL element 100 according to this embodiment is not limited to the above example. The EL element 100 according to this embodiment may be formed with other known layered structures. For example, the EL element 100 may omit one or more of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170, or may include other layers in addition. Each layer of the EL element 100 may be formed as a single layer or as multiple layers.

For example, the EL element 100 may further include a hole blocking layer between the hole transport layer 140 and the light emitting layer 150 to prevent excitons or holes from diffusing into the electron transport layer 160. The hole blocking layer may be formed of, for example, an oxadiazole derivative, a triazole derivative, or a phenanthroline derivative.

Furthermore, the polymer according to this embodiment can be applied to electroluminescence elements other than the above-mentioned QLED or OLED. Other electroluminescence elements to which the polymer according to this embodiment can be applied include, but are not limited to, organic-inorganic perovskite light-emitting elements.

The effects of the present invention will be explained using the following examples and comparative examples. However, the technical scope of the present invention is not limited to the following examples. In the following examples, unless otherwise specified, operations were performed at room temperature (25°C). Furthermore, unless otherwise specified, "%" and "parts" mean "% by mass" and "parts by mass", respectively.

Synthesis Example 1
(Synthesis of Intermediate 1-1)
Intermediate 1-1 was synthesized according to the following reaction.

Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (6.3 g, 14.3 mmol), 9-bromo-10-(2-naphthyl)anthracene (5.0 g, 13.0 mmol), sodium carbonate (1.38 g, 13.0 mmol), toluene (100 mL), and water (50 mL) were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.058 g, 0.26 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.21 g, 0.52 mmol) were added and the mixture was heated under reflux and stirred for 9 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.25 g of a white solid (intermediate 1-1) (yield 77%).

(Synthesis of Compound 1)
Compound 1 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 1-1 (5.0 g, 8.1 mmol), bispinacolatodiboron (8.2 g, 32.4 mmol), potassium acetate (4.8 g, 32.4 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.22 g, 0.24 mmol) and XPhos (0.46 g, 0.97 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 1 (5.35 g) (yield: 83%).

Synthesis Example 2
(Synthesis of Intermediate 2-1)
Intermediate 2-1 was synthesized according to the following reaction:

Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (11.3 g, 25.7 mmol), 9-bromoanthracene (6.0 g, 23.3 mmol), sodium carbonate (2.47 g, 23.3 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.104 g, 0.46 mmol) and XPhos (0.38 g, 0.93 mmol) were added and the mixture was heated and refluxed with stirring for 12 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.60 g of a white solid (intermediate 2-1) (yield 58%).

(Synthesis of Intermediate 2-2)
Intermediate 2-2 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 2-1 (6.6 g, 13.4 mmol) and dimethylformamide (DMF) (100 mL) were placed in a reaction vessel and stirred at 50°C. N-bromosuccinimide (2.3 g, 12.8 mmol) dissolved in DMF (200 mL) was added dropwise and stirred for 5 hours. Water (50 mL) was added to precipitate a solid. The resulting solid was washed with methanol to obtain 7.35 g of a solid (intermediate 2-2) (yield 96%).

(Synthesis of intermediate 2-3)
Intermediate 2-3 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 2-2 (7.35 g, 12.9 mmol), 9,9-dimethylfluorene-2-boronic acid (3.4 g, 14.2 mmol), sodium carbonate (1.64 g, 15.4 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.057 g, 0.25 mmol) and XPhos (0.21 g, 0.51 mmol) were added and the mixture was heated and refluxed with stirring for 5 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 6.45 g of a white solid (intermediate 2-3) (yield 73%).

(Synthesis of Compound 2)
Compound 2 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 2-3 (6.4 g, 9.3 mmol), bispinacolatodiboron (9.5 g, 37.4 mmol), potassium acetate (5.5 g, 56.2 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.25 g, 0.28 mmol) and XPhos (0.53 g, 1.12 mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 2 (7.64 g) (yield: 94%).

Synthesis Example 3
(Synthesis of Intermediate 3-1)
Intermediate 3-1 was synthesized according to the following reaction:

Under an argon atmosphere, the above intermediate 2-2 (10.0 g, 17.5 mmol), dibenzothiophene-2-boronic acid (4.4 g, 19.3 mmol), and sodium carbonate (
The mixture was stirred for 30 minutes after addition of 100 mL of toluene (2.23 g, 21.0 mmol), 100 mL of toluene, and 50 mL of water. Palladium acetate (0.057 g, 0.25 mmol) and XPhos (0.21 g, 0.51 mmol) were then added and the mixture was heated under reflux and stirred for 5 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 5.18 g of a white solid (intermediate 3-1) (yield 44%).

(Synthesis of Compound 3)
Compound 3 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 3-1 (5.2 g, 7.3 mmol), bispinacolatodiboron (7.8 g, 30.9 mmol), potassium acetate (4.5 g, 46.3 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.21 g, 0.23 mmol) and XPhos (0.44 g, 0.92 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 3 (5.17 g) (yield: 78%).

Synthesis Example 4
(Synthesis of Intermediate 4-1)
Intermediate 4-1 was synthesized according to the following reaction:

Under an argon atmosphere, 2-bromo-9,9-dibutylfluorene (10.0 g, 27.9 mmol), 9-anthraceneboronic acid (6.8 g, 30.7 mmol), sodium carbonate (3.55 g, 33.5 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Thereafter, palladium acetate (0.12 g, 0.56 mmol) and XPhos (0.46 g, 1.12 mmol) were added and the mixture was heated under reflux and stirred for 12 hours. After completion of the reaction, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was separated using MgSO
_The concentrate was purified by silica gel column chromatography to obtain 13.66 g of a solid (intermediate 4-1) (yield 100%).

(Synthesis of intermediate 4-2)
Intermediate 4-2 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 4-1 (13.7 g, 30.0 mmol) and dimethylformamide (DMF) (100 mL) were placed in a reaction vessel and stirred at 50°C. N-bromosuccinimide (5.0 g, 28.5 mmol) dissolved in DMF (200 mL) was added dropwise and stirred for 5 hours. Water (50 mL) was added to precipitate a solid. The resulting solid was washed with methanol to obtain 13.2 g of a solid (intermediate 4-2) (yield 82%).

(Synthesis of intermediate 4-3)
Intermediate 4-3 was synthesized according to the following reaction.

Under an argon atmosphere, N,N-bis(4-chlorophenyl)-2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenamine (4.5 g, 10.3 mmol), the above intermediate 4-2 (5.0 g, 9.3 mmol), sodium carbonate (0.99 g, 9.3 mmol), toluene 80 mL, and water 40 mL were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.042 g, 0.18 mmol) and XPhos (0.15 g, 0.37 mmol) were added and the mixture was heated and refluxed with stirring for 18 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 4.36 g of a solid (intermediate 4-3) (yield 60%).

(Synthesis of Compound 4)
Compound 4 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 4-3 (4.3 g, 5.6 mmol), bispinacolatodiboron (5.7 g, 22.7 mmol), potassium acetate (3.3 g, 34.1 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.15 g, 0.17 mmol) and XPhos (0.32 g, 0.68 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 4 (5.0 g) (yield: 92%).

Synthesis Example 5
(Synthesis of Intermediate 5-1)
Intermediate 5-1 was synthesized according to the following reaction.

Under an argon atmosphere, 2-bromo-7-iodo-9,9-dimethylfluorene (9.0 g, 22.6 mmol), 4,4,5,5-tetramethyl-2-[10-(2-naphthyl)anthracen-9-yl]-1,3,2-dioxaborolane (10.7 g, 24.8 mmol), sodium carbonate (2.86 g, 27.0 mmol), toluene 120 mL, and water 60 mL were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.10 g, 0.45 mmol) and XPhos (0.37 g, 0.90 mmol) were added and the mixture was heated under reflux and stirred for 17 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.98 g of a white solid (intermediate 5-1) (yield 84%).

(Synthesis of intermediate 5-2)
Intermediate 5-2 was synthesized according to the following reaction:

Under an argon atmosphere, the above intermediate 5-1 (11.0 g, 19.1 mmol), bis(4-chlorophenyl)amine (5.0 g, 21.0 mmol), sodium t-butoxide (2.2 g, 22.9 mmol), and 160 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Thereafter, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.17 g, 0.19 mmol), 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.42 g, 0.76 mmol) were added and the mixture was heated and refluxed with stirring for 4 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the mixture was purified by column chromatography to obtain a solid intermediate 5-2 (3.75 g) (yield 26%).

(Synthesis of Compound 5)
Compound 5 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 5-2 (3.75 g, 5.1 mmol), bispinacolatodiboron (5.2 g, 20.4 mmol), potassium acetate (3.0 g, 30.7 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.14 g, 0.15 mmol) and XPhos (0.29 g, 0.61 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 5 (3.8 g) (yield: 81%).

Synthesis Example 6
(Synthesis of Intermediate 6-1)
Intermediate 6-1 was synthesized according to the following reaction:

Under an argon atmosphere, the above intermediate 4-2 (8.2 g, 15.3 mmol), bispinacolatodiboron (11.7 g, 46.1 mmol), potassium acetate (9.1 g, 92.2 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl ₂ (dppf), 0.67 g, 0.922 mmol) was added and the mixture was heated and refluxed with stirring for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the mixture was purified by column chromatography to obtain intermediate 6-1 (7.05 g) (yield: 79%).

(Synthesis of Intermediate 6-2)
Intermediate 6-2 was synthesized according to the following reaction:

Under an argon atmosphere, 2-bromo-7-iodo-9,9-dimethylfluorene (4.4 g, 11.0 mmol), the above intermediate 6-1 (7.0 g, 12.1 mmol), sodium carbonate (1.4 g, 13.2 mmol), 100 mL of toluene, and 50 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, palladium acetate (0.098 g, 0.44 mmol) and XPhos (0.36 g, 0.88 mmol) were added and the mixture was heated and refluxed with stirring for 12 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 6-2 (6.96 g) (yield 87%).

(Synthesis of intermediate 6-3)
Intermediate 6-3 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 6-2 (7.0 g, 9.6 mmol), bis(4-chlorophenyl)amine (2.3 g, 9.6 mmol), sodium t-butoxide (1.1 g, 11.5 mmol), and 200 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Thereafter, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.044 g, 0.048 mmol), (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 0.090 g, 0.144 mmol) were added, and the mixture was heated and refluxed with stirring for 4 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain a solid intermediate 6-3 (2.07 g) (yield 24%).

(Synthesis of Compound 6)
Compound 6 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 6-3 (2.10 g, 2.4 mmol), bispinacolatodiboron (2.4 g, 9.5 mmol), potassium acetate (1.4 g, 14.3 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.065 g, 0.07 mmol) and XPhos (0.13 g, 0.28 mmol) were added and heated under reflux and stirred for 6 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 6 (2.2 g) (yield: 88%).

Synthesis Example 7
(Synthesis of Intermediate 7-1)
Intermediate 7-1 was synthesized according to the following reaction:

Under an argon atmosphere, 2-bromo-7-iodo-9,9-dihexylfluorene (6.0 g, 11.1 mmol), 4,4,5,5-tetramethyl-2-[10-(2-naphthyl)anthracen-9-yl]-1,3,2-dioxaborolane (4.5 g, 10.6 mmol), sodium carbonate (1.4 g, 13.3 mmol), toluene 100 mL, EtOH 10 mL, and water 50 mL were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh ₃ ] ₄ ) (0.77 g, 0.067 mmol) was added and the mixture was heated and refluxed and stirred for 8 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 7-1 (4.87 g) (yield 61%).

(Synthesis of Intermediate 7-2)
Intermediate 7-2 was synthesized according to the following reaction:

Under an argon atmosphere, the above intermediate 7-1 (4.9 g, 6.8 mmol), bis(4-chlorophenyl)amine (1.6 g, 6.8 mmol), sodium t-butoxide (0.78 g, 8.1 mmol), and 100 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Thereafter, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.016 g, 0.017 mmol), (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 0.032 g, 0.051 mmol) were added, and the mixture was heated and refluxed with stirring for 25 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography to obtain a solid intermediate 7-2 (3.91 g) (yield 65%).

(Synthesis of Compound 7)
Compound 7 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 7-2 (6.35 g, 7.3 mmol), bispinacolatodiboron (9.2 g, 36.4 mmol), potassium acetate (4.3 g, 43.6 mmol), and dioxane (150 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.19 g, 0.22 mmol) and XPhos (0.42 g, 0.87 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 7 (6.7 g) (yield: 87%).

Synthesis Example 8
(Synthesis of Intermediate 8-1)
Intermediate 8-1 was synthesized according to the following reaction:

Under an argon atmosphere, 2-bromo-7-iodo-9,9-dioctylfluorene (6.0 g, 10.1 mmol), 9-phenanthreneboronic acid (2.1 g, 9.6 mmol), sodium carbonate (1.4 g, 13.3 mmol), toluene 100 mL, EtOH 10 mL, and water 50 mL were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh ₃ ] ₄ ) (0.70 g, 0.061 mmol) was added and the mixture was heated and refluxed with stirring for 5 hours. After the reaction was completed, the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried using MgSO ₄ , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain intermediate 8-1 (6.21 g) (yield 95%).

(Synthesis of intermediate 8-2)
Intermediate 8-2 was synthesized according to the following reaction:

Under an argon atmosphere, the above intermediate 8-1 (6.2 g, 9.6 mmol), bis(4-chlorophenyl)amine (2.3 g, 9.6 mmol), sodium t-butoxide (1.11 g, 11.5 mmol), and 150 mL of toluene were added to a reaction vessel and stirred for 30 minutes. Thereafter, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.11 g, 0.12 mmol), 1,1'-bis(diphenylphosphino)ferrocene (dppf, 0.27 g, 0.48 mmol) were added and the mixture was heated and refluxed with stirring for 7 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the mixture was purified by column chromatography to obtain a solid intermediate 8-2 (3.71 g) (yield 48%).

(Synthesis of Compound 8)
Compound 8 was synthesized according to the following reaction.

Under an argon atmosphere, the above intermediate 8-2 (3.71 g, 4.6 mmol), bispinacolatodiboron (4.7 g, 18.4 mmol), potassium acetate (2.7 g, 27.7 mmol), and dioxane (100 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba) ₃ , 0.13 g, 0.14 mmol) and XPhos (0.26 g, 0.55 mmol) were added and heated under reflux and stirred for 5 hours. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. Next, the reaction mixture was filtered using Celite (registered trademark) to filter out impurities. Next, the solvent was distilled off from the filtrate, and the filtrate was purified by column chromatography to obtain compound 8 (4.2 g) (yield: 91%).

Synthesis Example 9
(Synthesis of Intermediate 9-1)
Intermediate 9-1 was synthesized according to the following reaction.

3-Chloro-carbazole (42.2 g, 0.209 mol), 4-bromohexylbenzene (50.2 g, 0.208 mol), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (9.57 g), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu) ₃ ·BF ₄ ) (4.55 g), t-butoxy sodium (40.2 g), and toluene (500 mL) were placed in a 1 L four-neck flask, and heated and stirred at 100°C for 8 hours under a nitrogen atmosphere. The mixture was allowed to cool to room temperature (25°C), and insoluble matter was filtered off using Celite (registered trademark). The solvent was removed from the filtrate under reduced pressure, and the mixture was purified by column chromatography to obtain intermediate 9-1 (56.5 g, 0.157 mol).

(Synthesis of intermediate 9-2)
Intermediate 9-2 was synthesized according to the following reaction:

Under an argon atmosphere, the above obtained intermediate 9-1 (6.3 g, 17.3 mmol), bispinacolatodiboron (8.8 g, 34.6 mmol), potassium acetate (5.1 g, 51.9 mmol), and dioxane (80 ml) were added to a reaction vessel and stirred for 30 minutes. Then, tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (0.47 g, 0.52 mmol) and Xphos (0.99 g, 2.08 mmol) were added and the mixture was heated under reflux and stirred for 8 hours.

After the reaction was completed, the reaction mixture was allowed to cool to room temperature. The reaction mixture was then filtered using Celite (registered trademark) to remove impurities. The solvent was then removed from the filtrate, which was then purified by column chromatography to obtain intermediate 9-2 (4.7 g) (yield: 60%).

(Synthesis of Compound 9)
Compound 9 was synthesized according to the following reaction.

Under an argon atmosphere, the intermediate 9-2 (9.0 g, 19.8 mmol) obtained above, 1,4-dibromo-2-iodobenzene (10.8 g, 29.8 mmol), sodium carbonate (3.2 g, 29.8 mmol), 120 mL of dioxane, and 60 mL of water were added to a reaction vessel and stirred for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd[PPh ₃ ] ₄ ) (1.15 g, 0.99 mmol) was added, and the mixture was heated under reflux and stirred for 12 hours.

After the reaction was completed, the mixture was cooled to room temperature, and the sample was transferred to a separatory funnel and extracted with toluene. The organic layer was dried over _MgSO4 , filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 4.5 g of a white solid (compound 9) (yield: 73%).

Example 1-1
(Synthesis of polymer compound A-1)
Under an argon atmosphere, the compound 1 (1.575 g) synthesized in Synthesis Example 1 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.080 g), palladium acetate (8.8 mg), tris(2-methoxyphenyl)phosphine (83.3 mg), toluene (53 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (10.15 g) were added and refluxed for 6 hours. Next, phenylboronic acid (238.4 mg), bis(triphenylphosphine)palladium(II) dichloride (83.0 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (10.15 g) were added and refluxed for 6 hours. Thereafter, the aqueous layer was removed, and N,N-diethyldithiocarbamate sodium trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 6 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel/alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-1 (0.90 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-1 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-1 were 138,900 and 3.34, respectively.

The polymer compound A-1 obtained in this manner has the following repeating units based on the monomer charging ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Example 1-2
(Synthesis of polymer compound A-2)
Under an argon atmosphere, the compound 2 (1.727 g) synthesized in Synthesis Example 2 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.094 g), palladium acetate (9.0 mg), tris(2-methoxyphenyl)phosphine (84.4 mg), toluene (56 mL), and 20% by mass aqueous solution of tetraethylammonium hydroxide (10.28 g) were added and refluxed for 6 hours. Next, phenylboronic acid (241.1 mg), bis(triphenylphosphine)palladium(II) dichloride (84.0 mg), and 20% by mass aqueous solution of tetraethylammonium hydroxide (10.28 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-2 (1.06 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-2 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-2 were 40,900 and 2.49, respectively.

The polymer compound A-2 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-3
(Synthesis of polymer compound A-3)
Under an argon atmosphere, the compound 3 (1.724 g) synthesized in Synthesis Example 3 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.105 g), palladium acetate (9.0 mg), tris(2-methoxyphenyl)phosphine (85.2 mg), toluene (57 mL), and 20% by mass aqueous solution of tetraethylammonium hydroxide (10.39 g) were added and refluxed for 6 hours. Next, phenylboronic acid (243.8 mg), bis(triphenylphosphine)palladium(II) dichloride (84.9 mg), and 20% by mass aqueous solution of tetraethylammonium hydroxide (10.39 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.59 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography filled with silica gel/alumina, and the solvent was distilled off under reduced pressure. The obtained liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-3 (1.40 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-3 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-3 were 132,900 and 3.20, respectively.

The polymer compound A-3 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-4
(Synthesis of polymer compound A-4)
Under an argon atmosphere, the compound 4 (1.748 g) synthesized in Synthesis Example 4 above, 2,7-dibromo-9,9-di-n-octylfluorene (1.009 g), palladium acetate (8.3 mg), tris(2-methoxyphenyl)phosphine (77.8 mg), toluene (55 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.49 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (222.7 mg), bis(triphenylphosphine)palladium(II) dichloride (77.5 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.49 g) were added, and the mixture was refluxed for 6 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 6 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-4 (1.22 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-4 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-4 were 76,900 and 2.38, respectively.

The polymer compound A-4 obtained in this manner has the following repeating units based on the monomer charging ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-5
(Synthesis of polymer compound A-5)
Under an argon atmosphere, the compound 5 (1.740 g) synthesized in the above Synthesis Example 5, 2,7-dibromo-9,9-di-n-octylfluorene (1.042 g), palladium acetate (8.5 mg), tris(2-methoxyphenyl)phosphine (80.3 mg), toluene (56 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.79 g) were added and refluxed for 6 hours. Next, phenylboronic acid (229.9 mg), bis(triphenylphosphine)palladium(II) dichloride (80 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.79 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and N,N-diethyldithiocarbamate sodium trihydrate (6.55 g) and ion-exchanged water (60 mL) were added and stirred at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass acetic acid aqueous solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-5 (1.21 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-5 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-5 were 90,000 and 2.50, respectively.

The polymer compound A-5 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-6
(Synthesis of polymer compound A-6)
Under an argon atmosphere, the compound 6 (1.621 g) synthesized in Synthesis Example 6 above, 2,7-dibromo-9,9-di-n-dodecylfluorene (1.005 g), palladium acetate (6.8 mg), tris(2-methoxyphenyl)phosphine (64.3 mg), toluene (53 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (7.84 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (184 mg), bis(triphenylphosphine)palladium(II) dichloride (64.1 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (7.84 g) were added, and the mixture was refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-6 (1.01 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-6 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-6 were 53,500 and 2.81, respectively.

The polymer compound A-6 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-7
(Synthesis of polymer compound A-7)
Under an argon atmosphere, the compound 7 (1.771 g) synthesized in Synthesis Example 7 above, 2,7-dibromo-9,9-di-n-octylfluorene (0.920 g), palladium acetate (7.5 mg), tris(2-methoxyphenyl)phosphine (70.9 mg), toluene (54 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (8.64 g) were added and refluxed for 6 hours. Next, phenylboronic acid (202.9 mg), bis(triphenylphosphine)palladium(II) dichloride (70.6 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (8.64 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added and stirred at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass acetic acid aqueous solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-7 (1.02 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-7 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-7 were 51,800 and 2.04, respectively.

The polymer compound A-7 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-8
(Synthesis of polymer compound A-8)
Under an argon atmosphere, the compound 7 (2.014 g) synthesized in the above Synthesis Example 7, 1,3-dibromo-5-dodecylbenzene (0.771 g), palladium acetate (8.6 mg), tris(2-methoxyphenyl)phosphine (80.7 mg), toluene (56 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.83 g) were added and refluxed for 6 hours. Next, phenylboronic acid (230.8 mg), bis(triphenylphosphine)palladium(II) dichloride (80.3 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.83 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (9.67 g) and ion-exchanged water (60 mL) were added and stirred at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass acetic acid aqueous solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-8 (1.19 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-8 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-8 were 14,300 and 1.73, respectively.

The polymer compound A-8 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which structural units (X) and (Y) according to the present invention are polymerized alternately.

Examples 1-9
(Synthesis of polymer compound A-9)
Under an argon atmosphere, the compound 7 (1.752 g) synthesized in the above Synthesis Example 7, the compound 9 (0.931 g), palladium acetate (7.4 mg), tris(2-methoxyphenyl)phosphine (35.1 mg), toluene (54 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.55 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (200.7 mg), bis(triphenylphosphine)palladium(II) dichloride (69.9 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.55 g) were added, and the mixture was refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (8.41 g) and ion-exchanged water (53 mL) were added, and the mixture was stirred at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-9 (1.37 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-9 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-9 were 38,000 and 1.97, respectively.

Examples 1-10
(Synthesis of polymer compound A-10)
Under an argon atmosphere, the compound 8 (1.581 g) synthesized in Synthesis Example 8 above, 2,7-dibromo-9,9-di-n-octylfluorene (0.879 g), palladium acetate (7.2 mg), tris(2-methoxyphenyl)phosphine (67.8 mg), toluene (49 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (8.26 g) were added and refluxed for 6 hours. Next, phenylboronic acid (194 mg), bis(triphenylphosphine)palladium(II) dichloride (67.5 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (8.26 g) were added and refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (5.46 g) and ion-exchanged water (54 mL) were added and stirred at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass acetic acid aqueous solution, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-10 (1.02 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-10 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-10 were 226,900 and 10.68, respectively.

The polymer compound A-10 thus obtained has the following repeating units based on the monomer charge ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

Examples 1-11
(Synthesis of polymer compound A-11)
Under an argon atmosphere, the compound 1 (1.525 g) synthesized in Synthesis Example 1 above, 2,7-dibromo-9,9-di-n-dodecylfluorene (1.260 g), palladium acetate (8.6 mg), tris(2-methoxyphenyl)phosphine (80.7 mg), toluene (56 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was refluxed for 6 hours. Next, phenylboronic acid (230.8 mg), bis(triphenylphosphine)palladium(II) dichloride (80.3 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.83 g) were added, and the mixture was refluxed for 7 hours. Thereafter, the aqueous layer was removed, and sodium N,N-diethyldithiocarbamate trihydrate (6.53 g) and ion-exchanged water (60 mL) were added, followed by stirring at 85° C. for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was dropped into methanol to precipitate the polymer compound, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel/alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was dropped into methanol, and the precipitated solid was filtered and dried to obtain polymer compound A-11 (1.23 g).

The weight average molecular weight (Mw) and dispersity (Mw/Mn) of the obtained polymer compound A-11 were measured by SEC. As a result, the weight average molecular weight (Mw) and dispersity (Mw/Mn) of the polymer compound A-7 were 59,900 and 2.26, respectively.

The polymer compound A-11 obtained in this manner has the following repeating units based on the monomer charging ratio, and is presumed to be a polymer compound in which the structural unit (X) and the structural unit (Y) according to the present invention are polymerized alternately.

[Evaluation of properties of each polymer compound]
For the polymer compounds A-1 to A-11 of Examples 1-1 to 1-11 above, the HOMO level (eV) and the glass transition temperature (Tg) (° C.) were measured by the following method. The results are shown in Table 1 below.

(Measurement of HOMO Levels)
Each polymer compound is dissolved in xylene to a concentration of 1% by mass to prepare a coating solution. The coating solution prepared above is used to form a film on a UV-cleaned glass substrate with ITO by spin coating at a rotation speed of 2000 rpm, and then dried on a hot plate at 150°C for 30 minutes to prepare a sample for measurement. The HOMO level of the sample is measured using an atmospheric photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). At this time, the tangent intersection point of the rising edge is calculated from the measurement result and is taken as the HOMO level (eV). The HOMO level is usually a negative value.

(Glass Transition Temperature (Tg))
Each polymer compound is measured using a differential scanning calorimeter (DSC) (Seiko Instruments Inc., product name: DSC6000) by heating the sample to 300° C. at a heating rate of 10° C./min and holding it for 10 minutes, then cooling it to 25° C. at a cooling rate of 10° C./min and holding it for 10 minutes, and then heating it to 300° C. at a heating rate of 10° C./min. After the measurement, the sample is cooled to room temperature (25° C.) at a rate of 10° C./min.

Reference Example (Fabrication of a Hole-Only Device)
A glass substrate on which a stripe-shaped indium tin oxide (ITO) film was formed to a thickness of 150 nm was prepared as a first electrode (anode). PEDOT-PSS (Sigma-Aldrich) was applied to the glass substrate by spin coating so as to have a dry thickness of 30 nm, and then dried to form a hole injection layer having a dry thickness of 30 nm.

Next, the polymer compound A-7 (hole transport material) obtained in Example 1-7 was dissolved in a xylene solvent at a concentration of 1% by mass to prepare a polymer coating solution. The polymer coating solution prepared above was applied by spin coating onto the hole injection layer formed above so that the dry film thickness was 30 nm, and then heated and dried at 150°C for 30 minutes. This formed a hole transport layer with a dry film thickness of 30 nm.

Next, in octane, the following structure:

A quantum dot dispersion was prepared by dispersing blue quantum dots of ZnTeSe/ZnSe/ZnS (core/shell/shell; average diameter = approximately 10 nm) having the above structure to a concentration of 2.0 mass %. The hole transport layer (particularly polymer compound P-1) does not dissolve in octane. This quantum dot dispersion was applied by spin coating onto the hole transport layer formed above so that the dry film thickness was 20 nm, and then heated and dried at 80°C for 30 minutes. This formed a quantum dot light-emitting layer (QD layer) with a dry film thickness of 20 nm.

Next, ZnCl was dissolved in ethanol as a solvent at a concentration of 0.7 mol/L to prepare a ZnCl coating solution. The ZnCl coating solution prepared above was slowly dripped onto the light-emitting surface formed above, and after leaving it for 60 seconds, it was rotated at 1000 rpm by spin coating for 40 seconds, and then heated and dried at 80°C for 20 minutes. Next, ethanol was slowly dripped onto the light-emitting surface formed above, and the operation of rotating at 1000 rpm by spin coating was repeated twice, and then heated and dried at 80°C for 20 minutes.

α-NPD (N,N'-di-1-naphthyl-N,N'-diphenylbenzidine) and HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) were successively deposited by vacuum deposition onto the hole transport layer formed above to form electron blocking layers with thicknesses of 36 nm and 10 nm, respectively, to produce hole-only device 1.

Comparative Example 1-1
(Fabrication of hole-only devices)
A hole-only element was prepared in the same manner as in Reference Example, except that poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) (manufactured by Luminescence Technology Corp.) having the following structural unit was used instead of polymer compound A-7.
The weight average molecular weight (Mw) and dispersity (Mw/Mn) of TFB were measured by SEC and were found to be 359,000 and 3.4, respectively.

[Evaluation of hole-only devices]
For each of the hole-only devices prepared in the above Reference Example and Comparative Example 1-1, the voltage was gradually increased using a DC constant voltage power supply (manufactured by KEYENCE, source meter) to measure the current value (current density (A/m ² )) at 8 V. This was referred to as the "current value @
The results are shown in Table 2 below.

From the results in Table 2 above, it can be said that the hole-only device of the Reference Example has a higher current value at 8 V than that of Comparative Example 1-1. This shows that A-7, which is an example of the polymer (polymer compound) according to the present invention and has fluorene substituted as Ar ³ , is excellent in hole (positive hole) mobility to the QD layer, which is the light-emitting layer.

Example 2-1
(Fabrication of Quantum Dot Electroluminescence Device 1)
A glass substrate with indium tin oxide (ITO) patterned to a thickness of 150 nm was used as the first electrode (anode). This glass substrate with ITO was washed successively with a neutral detergent, deionized water, water, and isopropyl alcohol, and then subjected to UV-ozone treatment. Next, poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS) (Sigma-Aldrich) was applied to the glass substrate with ITO by spin coating so that the dry thickness was 30 nm, and then dried. As a result, a hole injection layer with a thickness (dry thickness) of 30 nm was formed on the glass substrate with ITO.

Next, the polymer compound A-1 (hole transport material) synthesized in Example 1-1 was dissolved in toluene (solvent) at a concentration of 1% by mass to prepare a hole transport layer forming coating solution (1). This hole transport layer forming coating solution (1) was applied to the hole injection layer formed above by spin coating so as to have a thickness (dry film thickness) of 30 nm, and then heated at 230° C. for 1 hour to form a layer having a thickness (dry film thickness).
A 30 nm hole transport layer was formed on the hole injection layer.

In cyclohexane, the following structure:

Green quantum dots of InP/ZnSe/ZnS (core/shell/shell; average diameter = about 15 nm) having the above structure were dispersed to a concentration of 1.0 mass % to prepare a quantum dot dispersion. The hole transport layer (particularly polymer compound A-1) does not dissolve in cyclohexane. This quantum dot dispersion was applied to the hole transport layer by spin coating so that the dry film thickness was 30 nm, and then dried. As a result, a quantum dot light-emitting layer having a thickness (dry film thickness) of 30 nm was formed on the hole transport layer. The light emitted by irradiating the quantum dot dispersion with ultraviolet light had a central wavelength of 550 nm and a half-value width of 45 nm.

This quantum dot light-emitting layer was completely dried. Onto this quantum dot light-emitting layer, lithium quinolate (Liq) and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (Sigma-Aldrich) as an electron transport material were co-deposited using a vacuum deposition apparatus. As a result, an electron transport layer with a thickness of 36 nm was formed on the quantum dot light-emitting layer.

Using a vacuum deposition apparatus, (8-quinolinolato)lithium (lithium quinolate) (Liq) was deposited on the electron transport layer. As a result, an electron injection layer with a thickness of 0.5 nm was formed on the electron transport layer.

Aluminum (hereinafter, Al) was evaporated onto the electron injection layer formed above using a vacuum evaporation device to form a second electrode (cathode) with a thickness of 100 nm on the electron injection layer. This resulted in the quantum dot electroluminescence element 1 being obtained.

Example 2-2
(Fabrication of quantum dot electroluminescence device 2)
A quantum dot electroluminescence device 2 was produced in the same manner as in Example 2-1, except that the polymer compound A-2 of Example 2 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-3
(Fabrication of quantum dot electroluminescence element 3)
A quantum dot electroluminescence device 3 was prepared in the same manner as in Example 2-1, except that the polymer compound A-3 of Example 3 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-4
(Fabrication of quantum dot electroluminescence element 4)
A quantum dot electroluminescence device 4 was prepared in the same manner as in Example 2-1, except that the polymer compound A-4 of Example 4 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-5
(Fabrication of Quantum Dot Electroluminescence Device 5)
A quantum dot electroluminescence device 5 was prepared in the same manner as in Example 2-1, except that the polymer compound A-5 of Example 5 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-6
(Fabrication of Quantum Dot Electroluminescence Device 6)
A quantum dot electroluminescence device 6 was prepared in the same manner as in Example 2-1, except that the polymer compound A-6 of Example 6 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-7
(Fabrication of Quantum Dot Electroluminescence Device 7)
A quantum dot electroluminescence device 7 was prepared in the same manner as in Example 2-1, except that the polymer compound A-7 of Example 7 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-8
(Fabrication of Quantum Dot Electroluminescence Element 8)
A quantum dot electroluminescence device 8 was prepared in the same manner as in Example 2-1, except that the polymer compound A-8 of Example 8 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-9
(Fabrication of Quantum Dot Electroluminescence Device 9)
A quantum dot electroluminescence device 9 was prepared in the same manner as in Example 2-1, except that the polymer compound A-9 of Example 9 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-10
(Fabrication of Quantum Dot Electroluminescent Device 10)
A quantum dot electroluminescence device 10 was produced in the same manner as in Example 2-1, except that the polymer compound A-9 of Example 10 was used instead of the polymer compound A-1 in Example 2-1.

Example 2-11
(Fabrication of quantum dot electroluminescence device 11)
A quantum dot electroluminescence device 11 was produced in the same manner as in Example 2-1, except that the polymer compound A-9 of Example 11 was used instead of the polymer compound A-1 in Example 2-1.

Comparative Example 2-1
(Preparation of Comparative Quantum Dot Electroluminescence Device 1)
A comparative quantum dot electroluminescence device 1 was produced in the same manner as in Example 2-1, except that the TFB used in the above-mentioned Comparative Example 1-1 was used instead of the polymer compound A-1 in Example 2-1.

[Evaluation of quantum dot electroluminescence devices]
The quantum dot electroluminescence devices 1 to 11 prepared in the above Examples 2-1 to 2-11 and the comparative quantum dot electroluminescence device 1 prepared in the comparative example 2-1 were evaluated for luminous efficiency and luminous lifetime by the following method. The results are shown in Table 3 below.

(Luminous efficiency)
When a voltage is applied to each quantum dot electroluminescence element, a current starts to flow at a constant voltage, and the quantum dot electroluminescence element emits light. A DC constant voltage power supply (Keyence Corporation, source meter) is used to gradually increase the voltage for each element, and the current value at that time is measured, and the luminance during emission is measured using a luminance measuring device (Topcon Corporation, SR-3). Here, the measurement is stopped when the luminance starts to decay. The current value per unit area (current density) is calculated from the area of each element, and the current efficiency (cd/A) is calculated by dividing the luminance (cd/m ² ) by the current density (A/m ² ).

In addition, the external quantum efficiency (EQE) (%) at Cd/A max is calculated from the spectral radiance spectrum measured by the luminance measuring device, assuming that Lambertian radiation is used, and the luminous efficiency is evaluated.

(Light Emitting Life)
A predetermined voltage is applied to each quantum dot electroluminescent element using a DC constant voltage power supply (Keyence Corporation, source meter) to cause the quantum dot electroluminescent element to emit light. The light emitted by the quantum dot electroluminescent element is measured using a luminance measuring device (Topcon Corporation, SR-3) while gradually increasing the current, and when the luminance reaches 5400 nit (cd/m ² ), the current is made constant and the element is left as it is. The luminance value measured using the luminance measuring device gradually decreases, and the time until the luminance reaches 50% of the initial luminance is defined as "LT50 (hr)".

From the results in Table 3 above, it can be seen that the quantum dot electroluminescent devices 1 to 11 of the examples exhibit significantly higher durability (significantly longer luminous lifetime) than the comparative quantum dot electroluminescent device 1. It was also shown that the quantum dot electroluminescent devices 1 to 11 of the examples can achieve good luminous efficiency (EQE).

In this example, a green quantum dot electroluminescence element was evaluated, but it is believed that similar results will be obtained with a red quantum dot electroluminescence element, etc.

The present invention has been described above with reference to embodiments and examples, but the present invention is not limited to specific embodiments and examples, and various modifications and variations are possible within the scope of the invention described in the claims.

100...electroluminescence element (EL element),
110...substrate,
120...first electrode,
130...hole injection layer,
140...hole transport layer,
150...light-emitting layer,
160...electron transport layer,
170...electron injection layer,
180...Second electrode.

Claims (10)

A polymer comprising a structural unit (A) represented by the following formula (1):

In the above formula (1),
Ar ¹ to Ar ³ each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms;
^Ar4 is a substituted or unsubstituted fused polycyclic aromatic hydrocarbon group having three or more fused benzene rings;
^Ar5 is a group represented by the following formula (5) or (6) :
^Ar6 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 60 ring atoms;
p is 1 :

In the above formula (5),
X is a group selected from -C(R ⁵ )(R ⁶ )-, -O- and -S-;
R3 ^and R4 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R3 ^and R4 ^may be bonded to ^each other to form a ring;
R5 ^and R6 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R5 ^and R6 ^may be bonded to ^each other to form a ring;
a is 0, 1, 2, or 3; b is 0, 1, 2, 3, or 4;
When either a or b is 2 or more, each R ³ or each R ⁴ may be the same or different;
In the above formula (6),
R7 ^and R8 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R7 ^and R8 ^may be bonded to ^each other to form a ring;
c is 0, 1, 2, or 3; d is 0, 1, 2, 3, or 4;
When either c or d is 2 or more, each R ⁷ or each R ⁸ may be the same or different. The polymer according to claim 1, wherein, in the formula (1), Ar ⁴ is a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted tetracenylene group, or a substituted or unsubstituted chrysenylene group. The polymer according to claim 1 or 2, wherein, in the formula (1), Ar ³ is any one of groups represented by the following formulas (2) to (4):

In the above formula (3),
^R1 and ^R2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case ^R1 and ^R2 may be bonded to each other to form a ring. The polymer according to any one of claims 1 to 3 , wherein the group represented by the formula (5) is any one of groups represented by the following formulas (501) to (515):


In the above formulas (501) to (515),
R ³⁰¹ to R ³¹⁵ and R ⁴⁰¹ to R ⁴¹⁵ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which R ³⁰¹ and R 401 , R ³⁰² and R ⁴⁰² , R 303 and R ⁴⁰³ , R 304 and R ⁴⁰⁴ , R ³⁰⁵ and R ⁴⁰⁵ , R ³⁰⁶ and R ⁴⁰⁶ , R ³⁰⁷ and R ^{407 , R 308 and} R ⁴⁰⁸ , R ³⁰⁹ and R ⁴⁰⁹ , R ³¹⁰ and R ⁴¹⁰ , R ³¹¹ and R ⁴¹¹ , R ³¹² and R ^{412 ,} R ³¹³ and R ⁴¹³ , R ^{314 and R 414} , and R ³¹⁵ and R ⁴¹⁵ may be bonded to each other to form a ring;
R ⁵⁰⁴ to R ⁵⁰⁷ and R ⁶⁰⁴ to R ⁶⁰⁷ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which case R ⁵⁰⁴ and R ⁶⁰⁴ , R ⁵⁰⁵ and R ⁶⁰⁵ , R ⁵⁰⁶ and R ⁶⁰⁶ , and R ⁵⁰⁷ and R ⁶⁰⁷ may be bonded to each other to form a ring;
a1 to a15 each independently represent 0, 1, 2, or 3; b1 to b15 each independently represent 0, 1, 2, 3, or 4;
When any of a1 to a15 and b1 to b15 is 2 or more, each R ³⁰¹ , each R ³⁰² , each R ³⁰³ , each R ³⁰⁴ , each R ³⁰⁵ , each R ³⁰⁶ , each R ³⁰⁷ , each R ³⁰⁸ , each R ³⁰⁹ , each R ³¹⁰ , each R ³¹¹ , each R ³¹² , each R ³¹³ , each R ³¹⁴ , each R ³¹⁵ , each R ⁴⁰¹ , each R ⁴⁰² , each R ⁴⁰³ , each R ⁴⁰⁴ , each R ⁴⁰⁵ , each R ⁴⁰⁶ , each R ⁴⁰⁷ , each R ⁴⁰⁸ , each R ⁴⁰⁹ , each R ⁴¹⁰ , each R ⁴¹¹ , each R ⁴¹² , each R ⁴¹³ , each R ⁴¹⁴ or each R ⁴¹⁵ may be the same or different. The polymer according to any one of claims 1 to 4 , wherein, in the formula (1), Ar ⁶ is any one of groups represented by the following formulas (7) to (22):

In the above formulas (7) to (22),
R ⁹ to R ³⁵ each independently represent a substituted or unsubstituted monovalent aromatic hydrocarbon group having from 6 to 60 ring carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having from 5 to 60 ring atoms, an alkyl group having from 1 to 60 carbon atoms, or a hydrogen atom;
Q ¹ to Q ⁹ each independently represent -O-, -S-, -Se-, -CR ³⁶ R ³⁷ -, or -SiR ³⁸ R ³⁹ -, in which R ³⁶ to R ³⁹ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
Z ¹ to Z ⁷ each independently represent -CR ⁴⁰ =, -N=, or -SiR ⁴¹ =, in which R ⁴⁰ and R ⁴¹ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
* denotes the binding site that forms the main chain. A polymer comprising any one of structural units represented by the following formulas (A-1) to (A-11):

An electroluminescence device material comprising the polymer according to any one of claims 1 to 6 . An electroluminescence element comprising a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode,
An electroluminescence device, wherein at least one layer of the organic film comprises the polymer according to any one of claims 1 to 6 . 9. The electroluminescence device according to claim 8 , wherein the organic film containing the polymer is a hole transport layer or a hole injection layer. 10. The electroluminescence device according to claim 8 , wherein the organic film has a light-emitting layer containing semiconductor nanoparticles or an organometallic complex.