JP6659357B2 - Copolymer, organic electroluminescent device material, composition for producing organic electroluminescent device, and organic electroluminescent device - Google Patents

Description

  The present invention relates to a copolymer, an organic electroluminescent element material, a composition for producing an organic electroluminescent element, and an organic electroluminescent element.

  2. Description of the Related Art In recent years, a display device and a lighting device using an organic electroluminescence device (organic EL device), which is a self-luminous light emitting device, have been actively developed.

  In such an organic EL device, in order to manufacture a large-area device at lower cost (cost), use of a solution coating method instead of the vacuum evaporation method is being studied. The solution coating method has a higher use efficiency of materials, can easily form a large area film, and does not require an expensive vacuum apparatus, as compared with the vacuum evaporation method. This is expected as a method for manufacturing an element.

  As a material for an organic EL device used in the solution coating method, for example, a low molecular material and a high molecular material are being studied. Among them, polymer materials have been particularly developed because of their high coating uniformity and easy lamination. In particular, development of a polymer-based hole transport material that can be used in displays and lighting devices is desired.

  For example, the following Patent Documents 1 to 10 disclose a material for an organic EL device in which a part of a low-molecular material is substituted with a vinyl group and polymerized by polymerization.

JP-A-7-90255 JP-A-8-54833 JP-A-8-269133 JP 2001-098023 A JP-A-2002-110359 JP 2003-313240 A JP-A-2004-059743 JP 2006-237592 A JP 2008-198989 A JP 2008-218983 A

  However, the organic EL device manufactured by the solution coating method using the material for an organic EL device disclosed in Patent Documents 1 to 10 described above has a problem that the light emission lifetime is not sufficient.

  Therefore, the present invention has been made in view of the above problems, and an object of the present invention is to provide a new and improved copolymer capable of improving the emission life of an organic EL device. An object of the present invention is to provide an organic electroluminescent device material containing a copolymer, a composition for producing an organic electroluminescent device, and an organic electroluminescent device using the material.

According to an aspect of the present invention, there is provided a copolymer including a unit represented by the following general formula (1) and a unit represented by the following general formula (2). You.
In the above formula,
R ^{1 to} R ^{7 each} represent a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, an amino group, an nitro group, a nitro group, a cyano group, a substituted or unsubstituted silyl group. A (silyl) group, a substituted or unsubstituted alkyl (alkyl) group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl (cycloalkyl) group having 3 to 16 ring carbon atoms, a substituted or unsubstituted ring forming carbon An aryl (aryl) group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted Unsubstituted aryloxy (aryloxy) group having 6 to 30 ring carbon atoms, substitution Or an unsubstituted aralkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms An alkylamino group, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted alkylene (alkylene) group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene (cycloalkylene) group having 5 to 30 carbon atoms, A substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, a heteroarylene group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted amino group;
Cz is a group having a carbazole structure or an azacarbazole structure,
M _{is, - (A-B) n} -A m - or - a group represented _{by, - (B-A) n} -B m
here,
n is an integer of 1 to 20,
m is 0 or 1,
p is an integer of 1 to 10,
A is a group having a fluorene structure or an azafluorene structure;
B is a group represented by the general formula (3),
In the above general formula (3),
L ³ and L ⁴ each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring carbon atoms, substituted or unsubstituted An arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, A substituted or unsubstituted oxyarylene group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 40 carbon atoms, a substituted or unsubstituted aralkylene group having 5 to 30 carbon atoms, A substituted or unsubstituted amino group having 1 to 20 carbon atoms Killen (aminoalkylene) group, a substituted or unsubstituted ring forming amino arylene having from 6 to 30 carbon atoms (aminoarylene) group or a silylene substituted with an alkyl group or aryl group, (silylene) group,
R ⁸ represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring-forming carbon atoms, a substituted or unsubstituted ring-forming carbon atom having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 ring carbon atoms A substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, an unsubstituted ring forming an arylamino group having from 6 to 30 carbon atoms or a cyclic group is said that these groups L ₃ or the L ₄ is formed by combining,
* Is a binding site to another group.

  According to this viewpoint, the light emission lifetime of the organic EL element can be improved.

A is a group represented by the following general formula (4), and may be bonded to another group at any substitution position.
In the above general formula (4),
R ^{9 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substitution Alternatively, an unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 to 30 ring carbon atoms 0 arylamino group, a substituted or unsubstituted ring formed C6-30 aryl sulfoxide (arylsulfoxy) group or adjacent cyclic group these groups are bonded to each other to form,
a and b are each independently an integer from 1 to 4,
X ^{1 to} X ⁸ are each independently a methine group or a nitrogen atom.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

X ^{1 to} X ^{8 each} have a methine group;
R ⁹ and R ¹⁰ may be each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

L ¹ represents a single bond, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom having 6 to 30 carbon atoms. May be a heteroarylene group.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

The Cz may be a group represented by the following general formula (5) or a group in which a plurality of groups represented by the general formula (5) are linked.
In the above formula, Y ^{1 to} Y ⁸ are each independently a nitrogen atom or a methine group;
R ^{13 to} R ¹⁵ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. A group, a substituted or unsubstituted aminoalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted aminoaryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted carbon An aralkyl group having 7 to 40, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, or these adjacent groups are bonded to each other; A bond with a formed cyclic group or another group,
c and d are each independently an integer from 0 to 4.

The Cz may be a group represented by the following general formula (6) or (7) or a group in which a plurality of groups represented by the above general formula (6) or (7) are linked.
In the formula, * is a binding site to another group.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

Further, a polymerizable comonomer having at least one crosslinking group selected from the following crosslinking group may be included as a polymerized unit.
In the above crosslinking group,
R ^{15 to} R ²¹ are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
p is an integer of 1 to 10.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

The polymerizable comonomer may be a compound represented by the following general formula (8).
In the general formula (8),
R ^{22 to} R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
R ^{25 to} R ²⁹ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substitution Alternatively, an unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 or more substituted carbon atoms 30 arylamino group or an adjacent cyclic group these groups are bonded to each other to form,
L ⁵ is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring-forming carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 to 30. An arylene group, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having 6 to 30 carbon atoms. An oxyarylene group, a substituted or unsubstituted aralkylene group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aminoalkylene group having 1 to 20 carbon atoms, A substituted or unsubstituted aminoarylene group having 6 to 30 ring carbon atoms, or a silylene group substituted with an alkyl group or an aryl group,
At least one of R ^{25 to} R ²⁹ is a crosslinking group selected from the crosslinking group.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

Wherein L ⁵ represents may be a group represented by the following general formula (9).
In the above general formula (9),
A ′ is a group represented by the general formula (3),
B ′ is a group having a fluorene structure or an azafluorene structure,
r is an integer of 1 to 20,
* Is a binding site with a fluorenylene group.

L ⁵ may be a group represented by the general formula (3).

    According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

According to another embodiment of the present invention, there is provided a pair of electrodes,
And at least one or more organic layers disposed between the pair of electrodes,
An organic electroluminescent device is provided, wherein at least one of the organic layers contains the copolymer described above.

  According to this viewpoint, the light emission lifetime of the organic EL element can be improved.

  At least one of the organic layers may be a hole transport layer containing the copolymer.

  According to this viewpoint, it is possible to further improve the light emission lifetime of the organic EL element.

  At least one of the organic layers may be a light emitting layer containing a light emitting material capable of emitting light from triplet excitons.

  According to this viewpoint, the luminous efficiency and the luminous life of the organic EL element can be improved.

  According to another embodiment of the present invention, there is provided an organic electroluminescent device material including the copolymer.

  According to this viewpoint, the luminous efficiency and the luminous life of the organic EL element can be improved.

  According to another embodiment of the present invention, there is provided a composition for producing an organic electroluminescent device, comprising the above copolymer and a liquid medium.

  According to this viewpoint, it is possible to provide a composition suitable for the solution coating method and to improve the light emission lifetime of the organic EL element.

  As described above, according to the present invention, it is possible to improve the light emission lifetime of the organic EL element.

FIG. 1 is a schematic diagram illustrating an example of an organic EL device according to an embodiment of the present invention.

  Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. In the specification and the drawings, components having substantially the same functional configuration are denoted by the same reference numerals, and redundant description is omitted.

<1. Copolymer>
First, the copolymer according to the present embodiment will be described.
The copolymer according to the present embodiment includes a unit represented by the following general formula (1) (hereinafter, also referred to as “aminofluorene unit”) and a unit represented by the following general formula (2) (hereinafter referred to as “aminofluorene unit”). , "Carbazole units").

In the above formula,
R ^{1 to} R ⁷ are a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylamino group having 6 to 30 carbon atoms, An arylamino group,
L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted ring, An arylene group having 6 to 30 carbon atoms, a heteroarylene group having 6 to 30 ring atoms, or a substituted or unsubstituted amino group;
Cz is a group having a carbazole structure or an azacarbazole structure,
M _{is, - (A-B) n} -A m - or - a group represented _{by, - (B-A) n} -B m
here,
n is an integer of 1 to 20,
m is 0 or 1,
p is an integer of 1 to 10,
A is a group having a fluorene structure or an azafluorene structure,
B is a group represented by the general formula (3),

In the above general formula (3),
L ³ and L ⁴ each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring carbon atoms, substituted or unsubstituted An arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted An oxyarylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkylene group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, a substituted or unsubstituted carbon number 1 to 20 aminoalkylene groups, substituted or unsubstituted aminoarylene groups having 6 to 30 ring carbon atoms, or alkyl or aryl groups A conversion has been silylene group,
R ⁸ represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring-forming carbon atoms, a substituted or unsubstituted ring-forming carbon atom having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 ring carbon atoms A substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, an unsubstituted ring forming an arylamino group having 6 to 30 carbon atoms cyclic group or a with these groups L ₃ or L ₄ is formed by combining,
* Is a binding site to another group.

  Thereby, the light emission lifetime of the organic EL element containing the copolymer can be improved. More specifically, in the copolymer, the carbazole unit contributes to improving the glass transition point of the copolymer. Therefore, the copolymer as described above has a relatively high glass transition temperature and excellent thermal stability. Therefore, the organic EL device including the above copolymer is relatively stable to driving heat. In addition, as a result of suppressing deterioration and deformation of the organic EL element due to driving heat, the emission life of the organic EL element including the copolymer can be made longer than that of a conventional organic EL element.

  In addition, as described above, the copolymer has a relatively high glass transition temperature and is unlikely to be altered or deformed by heat when removing the solvent after forming the film. In the case where another layer is formed after film formation using the above copolymer, the above copolymer having a relatively high glass transition temperature is relatively hard to dissolve in a solvent. It is suitable for forming a laminated film in a solution coating method. As described above, the copolymer is suitably applicable to a solution coating method. Further, the organic layer formed by the solution coating method using the above-mentioned copolymer as a material is uniform without thickness unevenness. Further, the organic layer has a smooth surface. Therefore, in the organic EL device manufactured by using the above-mentioned copolymer as a material and using a solution coating method, unevenness in application of driving voltage and unevenness in light emission are suppressed.

  Further, when the bond dissociation energy between carbon atoms of a vinyl polymer in a cation radical state is calculated, fluorenyl (polymer) is more present in the polymerization site than in a vinyl polymer having a phenyl group in the polymerization site. A vinyl polymer having a fluorenyl) group has about three times higher bond dissociation energy between carbons. As a result, the copolymer having a fluorenyl group at the polymerization site is chemically stable, and therefore, the light emission lifetime of the organic EL device including the copolymer is improved.

Further, the copolymer has excellent hole transporting ability and hole injecting ability. Therefore, it can be suitably used as a hole transporting material, a hole injecting material, and a host material of the light emitting layer.
Hereinafter, each unit of the copolymer will be described in detail.

(Aminofluorene unit)
Hereinafter, the aminofluorene unit represented by the general formula (1) will be described.

As described above, R ^{1 to} R ⁴ of the aminofluorene unit each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group. A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, Amino group, a substituted or unsubstituted ring forming an arylamino group having 6 to 30 carbon atoms. In the present specification, the term "hydrogen atom" is a concept including "deuterium atom" even if there is no special description of "deuterium atom", and is present in each group. The hydrogen atom can optionally be a deuterium atom.

  The alkyl group can be a linear or branched alkyl group. The straight-chain or branched alkyl group is not particularly limited. For example, a methyl (methyl) group, an ethyl (ethyl) group, a propyl (propyl) group, a butyl (butyl) group, an octyl (octyl) group, a decyl ( decyl) group, a linear alkyl group such as a pentadecyl group, and a branched alkyl group such as a t-butyl group. The number of carbon atoms of the linear or branched alkyl group is preferably 1 to 15, more preferably 1 to 10, and more preferably 2 to 9. The number of carbon atoms of the cyclic alkyl group is not particularly limited, but is preferably 3 to 12, more preferably 3 to 10, and further preferably 4 to 7.

  Examples of the cycloalkyl group include a monocyclic hydrocarbon group such as a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicycloalkyl group, a tricycloalkyl group, and the like. And a cross-linked hydrocarbon group.

  Examples of the aryl group include a monocyclic aromatic group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quinquephenyl group, Non-condensed polycyclic aromatic groups such as a sexiphenyl group, a fluoranthenyl group, a triphenylenyl group, a naphthyl group, an anthryl group, a phenanthryl (phenanthryl) group fluorenyl group, indenyl group, pyrenyl group, acetonaphthene (acetonaphten) l) such as condensed polycyclic aromatic group such as a group can be exemplified. The number of ring-forming carbon atoms of the aryl group is preferably 6 to 18, and more preferably 6 to 12.

  Examples of the heteroaryl group include a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an oxazolyl group, an oxdiazolyl group, and an oxadiazolyl group. Furanyl group, pyranyl group, thienyl group, pyridyl group, pyridyl group, pyrazyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, triazinyl group quinolyl) and isoquinolyl (isoquinolyl) groups A loaryl group, a benzo (pyridyl) furanyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a carbolinyl group, and a phenanthridine group. , Acridinyl group, perimidinyl group, phenanthrolinyl group, benzoxazolyl group, benzothiazolyl (benzothiazolyl), quinoxalyl, quinoxalyl, quinoxalyl, quinoxalyl, quinoxalyl, quinoxalyl (Pyrazol l) group, and dibenzofuranyl (dibenzofuranyl) groups, and polycyclic heteroaryl groups such as dibenzothienyl (dibenzothienyl) group. The number of ring-forming atoms of the heteroaryl group is preferably from 3 to 24, more preferably from 5 to 12.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the alkoxy group, the cycloalkoxy group, and the aryloxy group include groups in which an oxygen atom is inserted into a bonding site with another group of the above-described alkyl group and cycloalkoxy group, respectively.
Further, examples of the alkylamino group and the arylamino group include, for example, an amino group in which the above-mentioned alkyl group and aryl group are substituted by 1, 2 or 3 groups.
Examples of the aralkyl group include a group in which the above-described alkyl group is substituted with one or more of the above-described aryl groups.

  The substituent which can be substituted on each of the above-mentioned groups such as an aryl group and an alkyl group is not particularly limited. For example, a cyano group, a silyl group, a mono-C 1-10 mono- ), A di (di-) or trialkylsilyl group, a linear, branched or cyclic alkyl (alkyl) group having 1 to 10 carbon atoms, a linear chain having 1 to 10 carbon atoms. Alternatively, a branched alkoxy group, an aryl group having 6 to 15 ring carbon atoms, an aryloxy group having 6 to 15 ring carbon atoms, and an arylcarbonyl group having 6 to 15 ring carbon atoms arylcarbonyl) group, a heterocyclyl group having 3 to 32 ring carbon atoms, and a heterocyclyl group having 1 to 10 carbon atoms. Roh (mono-) or di (di-) such as an alkylamino group and cyclization mono (mono-) or di (di-) arylamino group having a carbon number of 6 to 15 and the like. Unless otherwise stated, when simply described as "substituted", it can be substituted by the above substituents.

R ^{1 to} R ³ are preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 5 carbon atoms. And more preferably a hydrogen atom.

R ⁴ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, or a substituted or unsubstituted ring. It is an aryl group having 6 to 30 carbon atoms.

R ⁴ is more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and still more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 5 carbon atoms.

L ¹ is a group as described above.
Examples of the alkylene group include a linear or branched alkylene group having 1 to 20, preferably 1 to 10, and more preferably 1 to 3 carbon atoms. Examples of the alkylene group include a methylene (methylene) group, an ethylene (ethylene) group, an n-propylene (propylene) group, and an n-butylene (butylene) group.

  Examples of the arylene group include a phenylene group, a biphenylene group, a biphenylene group, a terphenylene group, a naphthylene group, etc. The arylene group may have 6 to 30 ring carbon atoms. However, it is preferably 6 to 24, more preferably 6 to 12.

  As the cycloalkylene group, a monocyclic group such as a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, or a decahydronaphthalenyl (decahydylen) group And polycyclic groups such as bicycloundecanediyl, and bridged ring hydrocarbon groups such as a bicycloalkylene group and a tricycloalkylene group. The number of ring-forming carbon atoms of the cycloalkylene group may be 5 to 30, but is preferably 5 to 24, and more preferably 5 to 12.

  Examples of the heteroarylene group include a pyrrole diyl group, a thiophene diyl group, a furan diyl group, a pyrazole diyl group, an imidazole diyl (imidazol diyl) group, and a pyrazole diyl group. oxazole diyl group, isoxazole diyl group, oxadiazole diyl group, triazole diyl group, thiadiazole diisyl group, thiadiazole diisyl group, and the like. A 5-membered aromatic heterocyclic group, pyridinediyl a 6-membered aromatic heterocyclic ring such as a yl) group, a pyridazine diyl group, a pyrimidin diyl group, a pyrazine diyl group, an indole diyl group, and an isoindol diyl group. Benzothiophene diyl group, isobenzothiophene diyl group, benzofuran diyl group, isobenzofuran diyl group, benzodithiol diyl group benzimidazole (diyl) group Imidazopyridine diyl (imidazopyridine diyl) group, benzothiazole-diyl (benzothiazole diyl) group, quinolinediyl (quinoline diyl) group, and bicyclic aromatic heterocyclic groups such as isoquinoline-diyl (isoquinoline diyl) group. The number of ring-forming carbon atoms of the heteroarylene group may be 5 to 30, preferably 5 to 24, and more preferably 5 to 12.

Among them, L ¹ is a single bond, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom. It is preferably a heteroarylene group having the number of 6 to 30, more preferably a single bond, a substituted or unsubstituted arylene group or a cycloalkylene group, further preferably a single bond or an unsubstituted arylene group, Even more preferably, it is a single bond, a phenylene group or a naphthylene group.

As described above, M _{is, - (A-B) n} -A m - or - a group represented by _{- (B-A) n -B} m.

In M, A is a group having a fluorene structure or an azafluorene structure.
A can be, for example, a group represented by the following general formula (4). When A is a compound represented by the following general formula (4), it can be bonded to another group at any substitution position.

In the above general formula (4),
R ^{9 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substitution Alternatively, an unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 to 30 ring carbon atoms 0 arylamino group, a substituted or unsubstituted ring formed C6-30 aryl sulfoxide group or adjacent cyclic group these groups are bonded to each other to form,
a and b are each independently an integer from 1 to 4,
X ^{1 to} X ⁸ are each independently a methine group or a nitrogen atom.

R ⁹ and R ¹⁰ are not particularly limited as long as they are the groups described above, but are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. Is preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted linear alkyl group having 1 to 20 carbon atoms. preferable. In this case, examples of the alkyl group and the aryl group include the same groups as those described above for R ^{1 to} R ⁴ .

R ¹¹ and R ¹² are not particularly limited as long as they are the groups described above, but are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. Or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. More preferably, it is a linear alkyl group having the number of 1 to 20. In this case, examples of the alkyl group and the aryl group include the same groups as those described above for R ^{1 to} R ⁴ .

When R ¹¹ and R ¹² are an aryl group or a heteroaryl group, they may be condensed with the fluorene structure or azafluorene structure in formula (4) to form a condensed ring.

Further, in X ^{1 to} X ⁴ , it is preferable that 0 or 1 of these is a nitrogen atom, more preferably, all are methine groups. In X ^{5 to} X ⁸ , it is preferable that 0 or 1 of these is a nitrogen atom, and more preferably, all are methine groups.

A is equal to or less than the number of methine groups in each of X ^{1 to} X ⁴ . Similarly, b is equal to or less than the number of methine groups in X ^{5 to} X ⁸ .

Hereinafter, specific examples of the group represented by the general formula (4) are shown.

B is a group represented by the following general formula (3), as described above.

In the general formula (4), L ³ and L ⁴ may be any of the groups described above, and are preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, More preferably, it is a single bond or a phenylene group, a birenifene group, or a naphthylene group, and further preferably, a single bond or a phenylene group.

Further, it is preferable that one of L ³ and L ⁴ is a single bond, and the other is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

R ⁸ may be any of the groups described above, and is preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. And more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and still more preferably an aryl group having 6 to 12 ring carbon atoms substituted with an alkyl group. In this case, examples of the alkyl group and the aryl group include the same groups as those described above for R ^{1 to} R ⁴ .

  Particularly, as the alkyl-substituted aryl group having 6 to 12 ring carbon atoms, a methylphenyl group and an ethylphenyl group are preferable.

  In the general formula (4), n may be an integer of 1 to 20, preferably 1 to 10, more preferably 1 to 5, further preferably 1 or 2. is there.

  Specific examples of the aminofluorene unit represented by the general formula (1) described above are shown below. However, the present invention is not limited to these structures.

(Carbazole unit)
Next, the carbazole unit represented by the general formula (2) will be described.

In the above formula, specific groups and preferred groups of R ^{5 to} R ^{7 can be} the same as the specific groups and preferred groups of R ^{1 to} R ⁴ described above.

Further, the carbazole unit of the general formula (2) has a p number of L ² and chain groups and Cz are polymerized alternately. Specific groups of L ² may be the same as the specific group of L ¹ described above. Among the above, L ² is a single bond, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group forming the ring having 6 to 30 carbon atoms or a substituted or unsubstituted ring atoms It is preferably a heteroarylene group having the number of 6 to 30, more preferably a single bond or a substituted or unsubstituted arylene group, even more preferably a single bond or a substituted or unsubstituted arylene group. Or a substituted or unsubstituted phenylene group or a fluorenediyl group.

  Cz is a group having a carbazole structure or an azacarbazole structure. For example, Cz can be a group represented by the following general formula (5) or a group in which a plurality of groups represented by the general formula (5) are linked.

In the above formula, Y ^{1 to} Y ⁸ are each independently a nitrogen atom or a methine group;
R ^{13 to} R ¹⁵ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. A group, a substituted or unsubstituted aminoalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted aminoaryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted carbon An aralkyl group having 7 to 40, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, or these adjacent groups are bonded to each other; A bond with a formed cyclic group or another group,
c and d are each independently an integer from 0 to 4.

The above-mentioned Y ^{1 to} Y ⁴ may be in the above-mentioned range, but it is preferable that 0 or 1 of them is a nitrogen atom, more preferably, all are methine groups. In Y ^{5 to} Y ⁸ , it is preferable that 0 or 1 of these is a nitrogen atom, and more preferably, all are methine groups.

A is equal to or less than the number of methine groups in each of Y ^{1 to} Y ⁴ . Similarly, b is equal to or less than the number of methine groups in each of Y ^{5 to} Y ⁸ .

  Preferably, Cz is a group represented by the following general formula (6) or (7) or a group in which a plurality of groups represented by the above general formula (6) or (7) are linked.

R ^{13 to} R ¹⁵ may be any of the groups described above, and are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms. A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aminoaryl group having 6 to 30 ring carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms An alkyl group having from 20 to 20 or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a hydrogen atom, an unsubstituted linear alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted It is a phenyl group or a fluorenyl group.

Also, if R ¹³ or R ¹⁴ is present in plurality adjacent plurality of R ¹³ or R ¹⁴ also form a fused ring with the carbazole skeleton represented by the general formula (5) (or aza carbazole skeleton) Good. Examples of such a cyclic group include an indolocarbazole ring.

When R ^{13 to} R ¹⁵ are an unsubstituted linear alkyl group having 1 to 15 carbon atoms, the carbon number is more preferably 1 to 12.

  In addition, p is an integer of 1 to 10 as described above, but is preferably an integer of 1 to 5, more preferably 1 or 2.

  Specific examples of the carbazole unit represented by the general formula (2) described above are shown below. However, the present invention is not limited to these structures.

(Other units)
The copolymer according to the present embodiment may have units other than the units described above.
For example, a polymerizable comonomer having at least one crosslinking group selected from the following crosslinking group may be included as a polymerized unit.

In the above crosslinking group,
R ^{15 to} R ²¹ are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
p is an integer of 1 to 10.

  Such a polymerizable comonomer can be, for example, a compound represented by the following general formula (8).

In the general formula (8),
R ^{22 to} R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
R ^{25 to} R ²⁹ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substitution Alternatively, an unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 or more substituted carbon atoms 30 arylamino group or an adjacent cyclic group these groups are bonded to each other to form,
L ⁵ is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring-forming carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 to 30. An arylene group, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having 6 to 30 carbon atoms. An oxyarylene group, a substituted or unsubstituted aralkylene group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aminoalkylene group having 1 to 20 carbon atoms, A substituted or unsubstituted aminoarylene group having 6 to 30 ring carbon atoms, or a silylene group substituted with an alkyl group or an aryl group,
At least one of R ^{25 to} R ²⁹ is a crosslinking group selected from the crosslinking group.

Specific examples and preferred groups of R ^{15 to} R ²⁹ described above can be the same as those of R ^{1 to} R ⁴ described above.
L ⁵ can be, for example, a group represented by the following general formula (9).

In the above general formula (9),
A ′ is a group represented by the general formula (3),
B ′ is a group having a fluorene structure or an azafluorene structure,
r is an integer of 1 to 20,
* Is a binding site with a fluorenylene group.

L ⁵ may be a group represented by the general formula (3).
Here, specific examples of the structural unit (repeating unit) corresponding to the polymerizable copolymer having at least one crosslinking group are shown below. However, the structural units corresponding to the polymerizable copolymer having at least one crosslinkable group are not limited to the structures exemplified below. In the following, m and n are, for example, integers of 1 to 10.

  Specific examples of the combination of each unit of the copolymer according to the embodiment described above will be described. However, the copolymer is not limited to these.

  The polymerization mode of the above copolymer is not particularly limited, and may be, for example, random copolymerization, alternating copolymerization, or block copolymerization.

  The number average molecular weight of the copolymer according to this embodiment is not particularly limited, and is, for example, 10,000 or more and 100,000 or less.

  According to the copolymer according to the present embodiment as described above, it is possible to improve the emission life of the organic EL element. Further, since the copolymer according to the present embodiment can be formed as a copolymer with a polymerizable comonomer having a crosslinking group to improve the stability of the coating film, the organic EL element is formed into a laminated structure. In this case, the light emission characteristics and the stability can be improved.

  The copolymer according to the present embodiment can be synthesized by using a known organic synthesis method. For example, the copolymer according to the present embodiment can be easily produced using a radical polymerization method. Those skilled in the art with reference to the examples described below can easily understand the specific method for synthesizing the copolymer according to the present embodiment.

<2. Organic Electroluminescent Element Material (Organic EL Element Material)>
The organic EL device material according to the embodiment includes the above-described copolymer. The copolymer is applicable as an organic EL device material. The copolymer has a hole transporting ability and a hole injecting ability. Therefore, the organic EL device material can be used, for example, as a material for a hole transport layer, a hole injection layer, and a light emitting layer.

  When the organic EL device material is a material for the light emitting layer, the above-described copolymer can be a host material. In this case, the organic EL device material may further include a compound having a hole transporting ability.

  The compound having such a hole transporting ability is not particularly limited, and includes a well-known hole injecting material, hole transporting material, and host material described later.

  When the organic EL element material is a material for the light emitting layer, the organic EL element material may include a light emitting material. Examples of such a material include a light emitting material described below.

<3. Composition for Manufacturing Organic Electroluminescent Element>
The composition for manufacturing an organic electroluminescent device according to the present embodiment is used, for example, for forming each layer of an organic EL device by a solution coating method.

  The composition for producing an organic electroluminescence device according to the present embodiment includes a compound represented by the general formula (1) and a liquid medium. Usually, the composition for manufacturing an organic electroluminescent device according to the present embodiment is configured to include the above-described organic EL device material and a liquid medium.

  The liquid medium is not particularly limited, but is preferably capable of dissolving the above-described organic EL device material. That is, the composition for producing an organic electroluminescence element is preferably a solution composition.

  Examples of such a liquid medium include, but are not particularly limited to, toluene (toluene), xylene (xylene), ethylbenzene (ethylbenzene), diethylbenzene (diethylbenzene), methysylene (mesitylene), propylbenzene (propylbenzene), and cyclohexylbenzene. cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl (isopropylbiphenyl), dimethyl biphenyl (isopropylbiphenyle) henyl acetate), phenyl propionic acid (phenyl propionate), methyl benzoate (methyl benzoate), an aromatic solvent such as ethyl benzoate (ethyl benzoate).

<4. Organic EL device>
Subsequently, the organic EL device according to the present embodiment will be described in detail with reference to FIG. FIG. 1 is a schematic diagram illustrating an example of the organic EL device according to the present embodiment.

  As shown in FIG. 1, the organic EL element 100 according to the present embodiment includes a substrate 110, a first electrode 120 disposed on the substrate 110, and 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, and an electron transport layer. An electron injection layer 170 disposed on the electron injection layer 160 and a second electrode 180 disposed on the electron injection layer 170 are provided.

  Here, the copolymer according to the present embodiment is included, for example, in any of the organic layers disposed between the first electrode 120 and the second electrode 180. Specifically, the copolymer according to this embodiment is preferably included in the hole transport layer 140 as a hole transport material. Note that the copolymer according to the present embodiment may be included in the light emitting layer 150 as a host material and in the hole injection layer 130 as a hole injecting material.

  Further, the organic layer containing the copolymer according to the present embodiment is formed by a solution coating method. Specifically, the organic layer containing the copolymer according to the present embodiment is formed by a spin coat method, a casting method, a micro gravure coat method, or 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, The film is formed using a solution coating method such as a flexographic printing method, an offset printing method, and an ink jet printing method. In addition, as a solvent used for the solution coating method, any solvent can be used as long as it can dissolve the copolymer according to the present embodiment.

  The method for forming a layer other than the organic layer containing the copolymer according to the present embodiment is not particularly limited. Layers other than the organic layer containing the copolymer according to the present embodiment may be formed by, for example, a vacuum evaporation method or may be formed by a solution coating method.

  As the substrate 110, a substrate used in a general organic EL element can be used. For example, the substrate 110 may be a semiconductor substrate such as a glass substrate, a silicon substrate, or a transparent plastic substrate.

  The first electrode 120 is formed on the substrate 110. The first electrode 120 is specifically an anode, and is formed of a metal, an alloy, a conductive compound, or the like having a large work function. For example, the first electrode 120 is formed of a transmissive type using indium tin oxide (In2O3-SnO2: ITO), indium zinc oxide (In2O3-ZnO), tin oxide (SnO2), zinc oxide (ZnO), and the like, which are excellent in transparency and conductivity. It may be formed as an electrode. Further, the first electrode 120 may be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), or the like on the transparent conductive film.

  The hole injection layer 130 is formed on the first electrode 120. The hole injection layer 130 is a layer that facilitates injection of holes from the first electrode 120, and specifically has a thickness of about 10 nm to about 1000 nm, more specifically, a thickness of about 10 nm to about 100 nm. May be formed.

  The hole injection layer 130 can be formed of a known hole injection material. Known hole injecting materials for forming the hole injecting layer 130 include, for example, poly (ether ketone) -containing triphenylamine (TPAPEK) and 4-isopropyl-4′-methyldiphenyliodonium tetrakis. (Pentafluorophenyl) borate (4-isopropyl-4'-methyldiphenyliodonium tetrakis (pentafluorophenyl) borate: PPBI), N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -Phenyl] -biphenyl-4,4'-diamine (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-a ino) -phenyl] -biphenyl-4,4'-diamine: DNTPD, copper phthalocyanine, 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine (4,4' , 4 "-tris (3-methylphenylylamino) triphenylamine: m-MTDATA), N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (N, N'-di (1-naphthyl) -N , N'-diphenylbenzidine: NPB), 4,4 ', 4 "-tris (diphenylamino) triphenylamine (4,4', 4" -tris (diphenylamine) triphenylamine: TDAT A), 4,4 ′, 4 ″ -tris (N, N-2-naphthylphenylamino) triphenylamine (4,4 ′, 4 ″ -tris (N, N-2-naphthylphenylamino) triphenylamine: 2-TNATA ), Polyaniline / dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenezenesulphonic acid), poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (poly (3,4-ethylenedioxythiophene) / poly (4-styrene) ), And polyaniline / 10-camphorsulphonic acid. Can be.

  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 with a thickness of, for example, about 10 nm to about 150 nm. The hole transport layer 140 is preferably formed by a solution coating method using the copolymer according to the present embodiment. According to this method, a copolymer capable of improving the emission life of the organic EL element 100 can be efficiently formed in a large area.

  However, when any other organic layer of the organic EL element 100 includes the copolymer according to the present embodiment, the hole transport layer 140 may be formed of a known hole transport material. Not even. Known hole transporting materials include, for example, 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (1,1-bis [(di-4-tolylamino) phenyl] cyclohexane: TAPC), N- Carbazole derivatives such as phenylcarbazole (N-phenylcarbazole) and polyvinylcarbazole (polyvinylcarbazole), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1-biphenyl] -4 , 4'-Diamine (N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine: TPD), 4,4 ', 4 " -Tris (N-carbazolyl Triphenylamine (4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine: TCTA) and N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine (N, N′-di) (1-naphthyl) -N, N'-diphenylbenzidine: NPB) and the like.

  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 a vacuum evaporation method, a spin coating method, an inkjet method, or the like. The light emitting layer 150 may be formed with a thickness of, for example, about 10 nm to about 60 nm. As a light emitting material of the light emitting layer 150, a known light emitting material can be used. Note that the light-emitting material included in the light-emitting layer 150 is preferably a light-emitting material that can emit light from triplet excitons (that is, phosphorescence). In such a case, the light emission lifetime of the organic EL element 100 can be further improved.

  The light-emitting layer 150 is formed of, for example, tris (8-quinolinolato) aluminum (Alq3), 4,4′-bis (carbazol-9-yl) biphenyl (4,4′-) as a host material. bis (carbazol-9-yl) biphenyl: CBP), poly (n-vinylcarbazole) (poly (n-vinylcarbazole): PVK), 9,10-di (naphthalen-2-yl) anthracene (9,10- di (naphthalene) anthracene: ADN), 4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine (4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine: TCTA), 1,3 5-Tris ( -Phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenyl-benzimidazol-2-yl) benzene: TPBI), 3-tert-butyl-9,10-di (naphth-2- Ill) anthracene (3-tert-butyl-9,10-di (naphth-2-yl) anthracene: TBADN), distyrylarylene (DSA), 4,4′-bis (9-carbazole) -2, It may contain 2'-dimethyl-biphenyl (4,4'-bis (9-carbazole) 2,2'-dimethyl-biphenyl: dmCBP) and the like.

  In addition, the light emitting layer 150 may be made of, for example, perylene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2- (p-dimethylaminostyryl) as a dopant material. ) -6-Methyl-4H-pyran (4-dicyanomethyl-2- (p-dimethylaminostyl) -6-methyl-4H-pyran: DCM) and derivatives thereof, bis [2- (4,6-difluorophenyl) pyridinate] Picolinate iridium (III) (bis [2- (4,6-difluorophenyl) pyridinate] picolinate iridium (III): FIrpic), bis (1-phenyl) Soquinoline) (acetylacetonate) iridium (III) (bis (1-phenylisoquinoline) (acetylacetonate) iridium (III): Ir (piq) 2 (acac)), tris (2-phenylpyridine) iridium (III) (tris ( It may include an iridium (Ir) complex such as 2-phenylpyridine) iridium (III): Ir (ppy) 3), an osmium (Os) complex, and a platinum complex.

  The electron transport layer 160 is formed on the light emitting layer 150. The electron transport layer 160 is a layer having a function of transporting electrons, and is formed by a vacuum evaporation method, a spin coating method, an inkjet method, or the like. The electron transport layer 160 may be formed with a thickness of, for example, about 15 nm to about 50 nm.

  The electron transport layer 160 may be formed of a known electron transport material. Known electron transport materials include, for example, tris (8-quinolinolato) aluminum (Alq3), a compound having a nitrogen-containing aromatic ring, and the like. Specific examples of the compound having a nitrogen-containing aromatic ring include, for example, 1,3,5-tri [(3-pyridyl) -phen-3-yl] benzene (1,3,5-tri [(3-pyridyl)) -Phen-3-yl] benzene, a compound containing a pyridine ring, 2,4,6-tris (3 ′-(pyridin-3-yl) biphenyl-3-yl) -1,3,3. A compound containing a triazine ring, such as 5-triazine (2,4,6-tris (3 ′-(pyridin-3-yl) biphenyl-3-yl) -1,3,5-triazine); -(4- (N-phenylbenzoinidazolyl-1-yl-phenyl) -9,10-dinaphthylanthracene (2- (4- (N-phenylbenzoimidazo) yl-1-yl-phenyl) -9,10-dinaphthylanthracene imidazole (imidazole) as) can be exemplified compounds comprising a ring.

  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, and is formed using a vacuum evaporation method or the like. The electron injection layer 170 may be formed with a thickness of about 0.3 nm to about 9 nm. As the electron injection layer 170, 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 made of (8-quinolinato) lithium (Liq) and a lithium compound such as lithium fluoride (LiF), sodium chloride (NaCl), and cesium fluoride (CsF). ), Lithium oxide (Li2O), or barium oxide (BaO).

  The second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is specifically a cathode, and is formed of a metal, an alloy, a conductive compound, or the like having a small work function. For example, the second electrode 180 may be made of a metal such as lithium (Li), magnesium (Mg), aluminum (Al), and calcium (Ca), or aluminum-lithium (Al-Li), magnesium-indium (Mg-In), The reflective electrode may be formed of an alloy such as magnesium-silver (Mg-Ag). In addition, the second electrode 180 may be formed as a transmission electrode by using a thin film of the metal material having a thickness of 20 nm or less and a transparent conductive film such as indium tin oxide (In2O3-SnO2) and indium zinc oxide (In2O3-ZnO). .

  The example of the organic EL element 100 according to the embodiment has been described above. The organic EL device 100 according to the embodiment has an organic layer containing a copolymer, so that the emission life can be further improved.

  Note that the laminated structure of the organic EL element 100 according to the embodiment is not limited to the above example. The organic EL element 100 according to the embodiment may be formed with another known laminated structure. For example, in the organic EL element 100, 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 may be omitted, and another layer may be additionally provided. You may have. Further, each layer of the organic EL element 100 may be formed as a single layer, or may be formed as a plurality of layers.

  For example, the organic EL element 100 further includes a hole blocking layer between the hole transport layer 140 and the light emitting layer 150 in order to prevent excitons or holes from diffusing into the electron transport layer 160. Is also good. The hole blocking layer can be formed using, for example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the like.

  Hereinafter, the polymer according to the present embodiment and the organic EL device including the polymer will be specifically described with reference to Examples and Comparative Examples. The following examples are merely examples, and the polymer and the organic EL device according to the present embodiment are not limited to the following examples.

(Example 1)
<Synthesis of Polymer A>
First, a monomer A was synthesized according to the scheme shown below.

  2,7-Dibromo-9,9-dimethyl-9H-fluorene (4.86 g, 13.8 mmol) was charged into a 300-ml three-necked flask, and after purging with argon, 50 ml of dehydrated tetrahydrofuran (THF, tetrahydrofuran) was added, followed by drying. Cooled with ice / acetone. Then, 5.6 ml of a 2.6 M normal butyl lithium hexane solution was added dropwise. After aging for 1 hour, the mixture was cooled again with a refrigerant, 1.7 ml of dehydrated N, N-dimethylformamide (DMF, N, N-dimethylformamide) was added dropwise, and the mixture was stirred for 1 hour. Thereafter, the temperature was returned to room temperature, and impurities were removed by filtration using Celite. After water was added to the filtrate, the mixture was extracted with toluene, and the extracted organic layer was concentrated. The concentrate was purified by column chromatography to obtain Compound 1.

  Compound 1 (4.16 g, 13.8 mmol), diphenylaminophenylboronic acid (4.63 g, 15.2 mmol), tetrakistriphenylphosphinepalladium (0.48 g, 0.41 mmol) in a reaction vessel under argon, 30 ml of 1,2-dimethoxyethane and 16.5 ml of a 2M aqueous sodium carbonate solution were added, and the mixture was stirred at 80 ° C. for 7 hours. After allowing to cool to room temperature, extraction was performed three times with toluene / water. The organic layer was concentrated, and then purified using a column chromatogram to obtain Compound 2.

  Under argon, triphenylmethylphosphonium bromide (4.07 g, 11.4 mmol) and 30 ml of dehydrated THF were added into a reaction vessel, and the mixture was cooled in an ice bath. Then, a solution of tBuOK (1.29 g, 11.5 mmol) dissolved in 30 ml of dehydrated THF was added dropwise. Then, a solution of 5.28 g (11.0 mmol) of Compound 2, dissolved in 30 ml of dehydrated THF, was added dropwise. After completion of the dropwise addition, the mixture was returned to room temperature and stirred for 3 hours. After completion of the reaction, extraction was performed three times with toluene / water. The organic layer was concentrated, and then purified using a column chromatogram to obtain a monomer A. The structure of monomer A was identified using a high performance liquid chromatograph mass spectrometer (LC-MS).

  Next, a polymer A shown below was formed from the monomer A and vinylcarbazole. In a reaction vessel under argon, monomer A (0.50 g, 1.04 mmol), vinylcarbazole (0.50 g, 2.59 mmol), azobisisobutyronitrile (AIBN, azobisisobutyronitrile) (0.005 g, 0.1 g). 0305 mmol) and 10 ml of dehydrated toluene were added, and the mixture was stirred at 80 ° C. for 8 hours under an argon flow. After cooling to room temperature, methanol was added, and the precipitate was filtered. The obtained solid was dissolved in THF, and purified by reprecipitation using acetone to obtain 0.24 g of a polymer A containing the following unit. In addition, as a result of measurement by gel permeation chromatography (GPC), the molecular weight of the polymer A was a number average molecular weight (Mn) = 29,100 and a weight average molecular weight (Mw) = 79,100). In the polymer A, n: m for each of the following units was 7: 3.

<Measurement of glass transition temperature>
About the obtained polymer A, the glass transition temperature (Tg) was measured. The glass transition temperature was measured using SII DSC6220 (manufactured by Seiko Instruments Inc.) in accordance with JIS K 7121.

<Evaluation of membrane stability>
The stability of the film formed using the obtained polymer A was evaluated as follows. Indium tin oxide (ITO) is applied on a glass substrate with ITO having a thickness of 150 nm by spin coating from a 1% by mass solution of xylene (xylene) of polymer A to a thickness of 30 nm. A film was formed.
The surface of the obtained film was observed with an optical microscope to evaluate the state of the film. The state of the film was evaluated according to the following criteria.
：: Uniform and defect-free state ：: A small number of dark spots are visible, but a device can be formed. X: A continuity of the film cannot be secured and a device cannot be formed.

<Manufacture of organic EL element>
Next, an organic EL device containing the polymer according to this embodiment was manufactured by the following steps.

First, PEDOT / PSS (manufactured by Sigma-Aldrich) is applied as a first electrode (anode) on a glass substrate with ITO by a spin coating method so that a dry film thickness becomes 30 nm. An injection layer was formed.
Next, the polymer A synthesized above was dissolved in xylene at 1% by mass to prepare a hole transport layer coating solution. On the hole injecting layer, a hole transporting layer coating solution was applied by a spin coating method so as to have a dry film thickness of 30 nm, and heated at 230 ° C. for 1 hour to form a hole transporting layer.

  Subsequently, on the hole transport layer, triphenylsilyl, 3,6-biscarbazoylbenzene (TPSmCP) and 4,4′-bis (carbazol-9-yl) biphenyl (CBP) as a host material, a dopant As a material, tris (2- (3-p-xyyl) phenyl) pyridine iridium (III) was co-evaporated with a vacuum evaporation apparatus to form a light-emitting layer having a thickness of 30 nm. In addition, the ratio of TPSmCP and CBP was set to TPSmCP: CBP = 7: 3 by mass ratio, and the doping amount of tris (2- (3-p-xyyl) phenyl) pyridine iridium (III) was set to 10% by mass. .

  Next, (8-quinolinolato) lithium (Liq) and KLET-03 (manufactured by Chemipro Kasei) were co-evaporated on the light-emitting layer using a vacuum evaporation apparatus to form an electron transport layer having a thickness of 50 nm. Lithium fluoride (LiF) was deposited on the electron transporting layer by a vacuum deposition apparatus to form an electron injection layer having a thickness of 1 nm. Further, aluminum was vapor-deposited on the electron injection layer by a vacuum vapor deposition apparatus to form a second electrode (cathode) having a thickness of 100 nm. An organic EL device was prepared by the above method.

<Evaluation of organic EL element>
The current efficiency and the light emission lifetime of the organic EL device prepared above were evaluated by the following methods.
A predetermined voltage was applied to each organic EL element using a DC constant-voltage power supply (source meter manufactured by KEYENCE) to cause the organic EL element to emit light. The current was gradually increased while the light emission of the organic EL element was measured by a luminance measuring device (SR-3 manufactured by Topcom). When the luminance reached 3000 cd / m ² , the current density was measured and the current was kept constant. I left it. "Current efficiency" was calculated from the obtained current density.

The time required for the luminance value measured by the luminance measuring device to gradually decrease to 80% of the initial luminance was defined as "light emission lifetime".
Table 1 shows the evaluation results. In Table 1, the current efficiency and the light emission lifetime are shown as relative values when the measured value in Comparative Example 1 is 100.

(Examples 2-3 and Comparative Examples 1-2)
The device was prepared and evaluated in the same manner as in Example 1 except that the hole transport layer was formed of the polymer shown in Table 1. Table 1 shows the results.
The monomers used in the polymerization of the polymers B, C and b were synthesized according to the following reaction scheme.

  Referring to the results in Table 1, in Examples 1 to 3 in which the copolymer according to the present embodiment was used for the hole transport layer, the copolymer had a higher Tg and a higher film stability than Comparative Example 2. It was good.

  Further, in Examples 1 to 3 in which the copolymer according to the present embodiment was used for the hole transport layer, the current efficiency and the emission lifetime were improved as compared with Comparative Example 1, and the copolymer according to the present embodiment was improved. It can be seen that the coalescence has high performance as a hole transporting material.

  As can be seen from the above results, the polymer according to the present embodiment can be efficiently formed into a film by a solution coating method, and can improve the current efficiency and the light emission lifetime of the organic EL element. is there.

  As described above, the preferred embodiments of the present invention have been described in detail with reference to the accompanying drawings, but the present invention is not limited to such examples. It is apparent that those skilled in the art to which the present invention pertains can conceive various changes or modifications within the scope of the technical idea described in the claims. It is understood that these also belong to the technical scope of the present invention.

Reference Signs List 100 organic 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 (15)

A unit represented by the following general formula (1), and a unit represented by the following general formula (2) seen including,
Further, a polymerizable comonomer having at least one cross-linking group selected from the following cross-linking group is included as a polymerized unit,
The copolymer, wherein the polymerizable comonomer is a compound represented by the following general formula (8) .


In the above formula,
R ¹ to R ⁷ is a hydrogen atom, a deuterium atom, a halogen atom, hydroxy group, an amino group, a nitro group, a cyano group, silyl group, an alkyl group having a carbon number of 1 to 20, ring carbon 3-16 cycloalkyl group, ring-forming aryl group having 6 to 30 carbon atoms, an alkoxy group having a carbon number of 1 to 20, cycloalkoxy group ring carbon 3-16, ring-forming aryloxy group having 6 to 30 carbon atoms, carbon number aralkyl groups 7 to 40, alkylamino group having a carbon number of 1 to 20, an arylamino group ring forming having 6 to 30 carbon atoms,
L ¹ and ^{L 2} are independently of each other, a single bond, an alkylene group having a carbon number of 1 to 10, a cycloalkylene group having a carbon number of 5-30, arylene Motoma other amino group of the ring-forming having 6 to 30 carbon atoms And
Cz is a group having a carbazole structure or an azacarbazole structure,
M _{is, - (A-B) n} -A m - or - a group represented _{by, - (B-A) n} -B m
here,
n is an integer of 1 to 20,
m is 0 or 1,
p is an integer of 1 to 10,
A is a group represented by the following general formula (4) ,

In the above general formula (4),
R ^{9 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, and a ring having 3 to 16 carbon atoms. Cycloalkyl group, aryl group having 6 to 30 ring carbon atoms, alkoxy group having 1 to 20 carbon atoms, cycloalkoxy group having 3 to 16 ring carbon atoms, aryloxy group having 6 to 30 ring carbon atoms, carbon number An aralkyl group having 7 to 40 carbon atoms, an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 30 ring carbon atoms, an arylsulfoxy group having 6 to 30 ring carbon atoms, or adjacent groups bonded to each other A cyclic group formed by
a and b are each independently an integer from 1 to 4,
X ^{1 to} X ⁸ are each independently a methine group or a nitrogen atom;
B is a group represented by the general formula (3),

In the above general formula (3),
L ³ and ^{L 4,} independently of one another, a single bond, an alkylene group having a carbon number of 1 to 20, a cycloalkylene group ring carbon 3-16, ring-forming arylene group having 6 to 30 carbon atoms, carbon number 1 20 oxyalkylene groups, oxy cycloalkylene group ring carbon 3-16, oxyarylene groups forming the ring having 6 to 30 carbon atoms, an aralkylene group having a carbon number of 7 to 40, aminoalkylene group having a carbon number of 1 to 20 An aminoarylene group having 6 to 30 ring carbon atoms, or a silylene group substituted with an alkyl group or an aryl group,
R ⁸ represents a hydrogen atom, an alkyl group having a carbon number of 1 to 20, a cycloalkyl group having ring carbon 3 to 16, carbon atoms of 1 to 10 linear or branched or cyclic alkyl group is substituted unsubstituted ring forming aryl group having 6 to 30 carbon atoms, an alkoxy group having a carbon number of 1 to 20, cycloalkoxy group ring carbon 3-16, ring-forming aryloxy group having 6 to 30 carbon atoms, carbon number 7 40 aralkyl group, an alkylamino group having a carbon number of 1 to 20, ring-forming arylamino group having 6 to 30 carbon atoms or said L ₃ or the L ₄ are bonded to a cyclic group formed by these groups, And
* Is a binding site to another group;

In the above crosslinking group,
R ^{15 to} R ²¹ are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
p is an integer from 1 to 10;

In the general formula (8),
R ^{22 to} R ²⁴ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms,
R ^{25 to} R ²⁹ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substitution Alternatively, an unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 40 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 carbon atoms with ring 30 arylamino group or an adjacent cyclic group these groups are bonded to each other to form,
L ⁵ is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring-forming carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 to 30. An arylene group, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having 6 to 30 carbon atoms. An oxyarylene group, a substituted or unsubstituted aralkylene group having 7 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aminoalkylene group having 1 to 20 carbon atoms, A substituted or unsubstituted aminoarylene group having 6 to 30 ring carbon atoms, or a silylene group substituted with an alkyl group or an aryl group,
At least one of R ^{25 to} R ²⁹ is a crosslinking group selected from the crosslinking group . X ^{1 to} X ^{8 each} have a methine group;
The copolymer according to claim 1 , wherein R ⁹ and R ¹⁰ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. L ¹ is a single bond, a cycloalkylene group or a ring-forming arylene group having 6 to 30 carbon atoms having a carbon number of 5-30, a copolymer according to claim 1 or 2. Wherein Cz is a group represented by the following general formula a group represented by the group or of the general formula represented by (5) (5) was ligated, co according to any one of claims 1 to 3 Polymer.

In the above formula, Y ^{1 to} Y ⁸ are each independently a nitrogen atom or a methine group;
R ^{13 to} R ¹⁵ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. A group, a substituted or unsubstituted aminoalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted aminoaryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted carbon atom An aralkyl group having 7 to 40, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, or these adjacent groups are bonded to each other; A bond with a formed cyclic group or another group,
c and d are each independently an integer from 0 to 4. Wherein Cz is a group represented by the following general formula (6) or a group represented by the group or of the general formula represented by (7) (6) or (7) linked, co according to claim 4 Polymer.


In the formula, * is a binding site to another group. Wherein L ⁵ represents a group represented by the following general formula (9), a copolymer according to any one of claims 1 to 5.

In the above general formula (9),
A ′ is a group represented by the general formula (3),
B ′ is a group having a fluorene structure or an azafluorene structure,
r is an integer of 1 to 20,
* Is a binding site with a fluorenylene group. Wherein L ⁵ represents a group represented by the general formula (3), a copolymer according to any one of claims 1 to 6.   The copolymer according to any one of claims 1 to 7, wherein the unit represented by the general formula (1) is at least one selected from the following group.






  The copolymer according to any one of claims 1 to 8, wherein the unit represented by the general formula (2) is at least one selected from the following group.



  The copolymer according to any one of claims 1 to 9, wherein the structural unit derived from the polymerizable comonomer is at least one selected from the following group.

A pair of electrodes;
And at least one or more organic layers disposed between the pair of electrodes,
An organic electroluminescent device, wherein at least one of the organic layers contains the copolymer according to any one of claims 1 to 10.   The organic electroluminescence device according to claim 11, wherein at least one of the organic layers is a hole transport layer containing the copolymer.   13. The organic electroluminescence device according to claim 11, wherein at least one of the organic layers is a light emitting layer containing a light emitting material capable of emitting light from triplet excitons.   An organic electroluminescence device material comprising the copolymer according to claim 1.   A composition for producing an organic electroluminescence device, comprising the copolymer according to any one of claims 1 to 10 and a liquid medium.