Composition for light-emitting diodes containing thermally crosslinkable low-molecular-weight compound

Abstract

The purpose of the present invention is to provide a composition for a light emitting diode, with which the service life of an organic EL element having an organic layer formed using a polymer material can be made longer than in the past.　The present invention is a composition for a light-emitting diode, which contains a high molecular weight compound and a thermally crosslinkable low molecular weight compound. The thermally crosslinkable low molecular weight compound is a compound having two or more thermally crosslinkable structures in the molecule. The thermally crosslinkable low molecular weight compound is preferably a compound having two or more thermally crosslinkable structures selected from among acrylate structures, methacrylate structures and maleimide structures in the molecule.

Description

[Technical Field]

[0001] The present invention relates to a composition for light-emitting diodes and an organic electroluminescence device using the same. [Background technology]

[0002] Organic electroluminescent elements (hereinafter referred to as organic EL elements), a type of light-emitting diode, are self-luminous elements that are brighter and more visible than liquid crystal elements, and are capable of producing clearer displays, so they have been the subject of active research.

[0003] Organic EL elements have a structure in which a thin film of an organic compound (hereinafter also referred to as the organic layer) is sandwiched between an anode and a cathode. Thin film formation methods can be broadly divided into vacuum deposition and coating methods. Vacuum deposition is a technique in which a thin film is formed on a substrate in a vacuum using mainly low-molecular-weight compounds, and is a technology that has already been put to practical use. On the other hand, coating is a technique in which a thin film is formed on a substrate using a solution, such as inkjet printing, mainly using high-molecular-weight compounds. This method is highly efficient in the use of materials and is suitable for larger areas and higher resolution, making it an essential technology for future large-area organic EL displays.

[0004] The vacuum deposition method using low-molecular-weight materials has extremely low material utilization efficiency, and as the size increases, the shadow mask bends more, making uniform deposition on large substrates difficult. It also has other problems, such as high manufacturing costs.

[0005] On the other hand, polymeric materials can be dissolved in organic solvents and applied to form uniform films on large substrates, allowing for application methods such as inkjet printing and printing to be used, thereby increasing the efficiency of material use and significantly reducing the manufacturing costs of devices.

[0006] Various organic EL devices using polymer materials have been investigated to date, but there have been problems in that device characteristics such as luminous efficiency and life span are not necessarily sufficient (see, for example, Patent Documents 1 to 6).

[0007] A fluorene polymer called TFB has been known as a typical hole transport material used in polymer-based organic EL devices (see Patent Documents 7 and 8). However, TFB has insufficient hole transport properties and electron blocking properties, which means that some electrons pass through the light-emitting layer, preventing improvements in luminous efficiency. Furthermore, TFB has poor film adhesion to adjacent layers, preventing the device from achieving a long life.

[0008] Furthermore, the present inventors have previously developed various hole transport materials for use in polymer organic EL devices (see Patent Documents 9 and 10), but these have had the problem of insufficient device life. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] US20080274303 [Patent Document 2] Japanese Patent Application Laid-Open No. 2007-119763 [Patent Document 3] US20100176377 [Patent Document 4] Patent No. 5018043 [Patent Document 5] US7651746 [Patent Document 6] US20120256537 [Patent Document 7] EP0988337 [Patent Document 8] US8974917 [Patent Document 9] US20190326515 [Patent Document 10] US20190378989 Summary of the Invention

[0010] An object of the present invention is to provide a composition for light-emitting diodes that can extend the life of an organic EL device having an organic layer formed using a polymer material.

[0011] As a result of extensive research, the present inventors have found that an organic EL device having an organic layer formed using a composition for a light-emitting diode containing a high molecular weight compound and a thermally crosslinkable low molecular weight compound has a long life, and have completed the present invention.

[0012] In the organic EL device of the present invention, it is preferable that the organic layer formed by forming a film of a composition for a light-emitting diode containing a high-molecular-weight compound and a thermally crosslinkable low-molecular-weight compound is a hole-transporting layer, an electron-blocking layer, a hole-injecting layer, or a light-emitting layer.

[0013] That is, the present invention is as follows.

[0014] [1] A composition for a light-emitting diode, comprising a high-molecular-weight compound and a thermally crosslinkable low-molecular-weight compound, A composition for a light-emitting diode, wherein the thermally crosslinkable low-molecular-weight compound is a compound having two or more thermally crosslinkable structures in the molecule.

[0015] [2] The composition for a photodiode according to [1], wherein the thermally crosslinkable low molecular weight compound is a compound having two or more thermally crosslinkable structures selected from an acrylate structure, a methacrylate structure, and a maleimide structure in the molecule.

[0016] [3] The composition for light-emitting diodes according to [2], wherein the thermally crosslinkable low molecular weight compound is a compound represented by the following general formula (1):

[0017] [ka] (Wherein, L1 is an arylene group, a heteroarylene group, an alkylene group, or a disulfide group; L2 is an arylene group, a heteroarylene group, a disulfide group, or a single bond; A may be the same or different and is a group selected from the following formulae A1, A2, and A3.

[0018] [ka] (In the formula, the dashed line represents the binding site.)

[0019] [4] The composition for light-emitting diodes according to [3], wherein, in the general formula (1), L1 is a phenylene group, a naphthalene group, or a biphenylene group, and L2 is a single bond, or L1 is an alkylene group having 2 to 6 carbon atoms, and L2 is a phenylene group or a naphthalene group.

[0020] [5] The composition for light-emitting diodes according to any one of [1] to [4], wherein the high molecular weight compound contains a repeating unit having a triarylamine structural unit represented by the following general formula (2), and has a weight average molecular weight of 10,000 or more and less than 1,000,000 in terms of polystyrene:

[0021] [ka] (In the formula, Ar1 and Ar2 each independently represent an arylene group or a heteroarylene group, R3 and R4 each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms; X, Y, and Z each independently represent an aryl group, a heteroaryl group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms, provided that at least one of them is an aryl group or a heteroaryl group.

[0022] [6] The composition for light-emitting diodes according to [5], wherein the high-molecular-weight compound is a copolymerized high-molecular-weight compound further comprising a repeating unit having one or more structural units selected from the group consisting of structural units represented by the following general formulas (3a) to (3x):

[0023] [ka] (wherein R5 represents a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, a cycloalkyloxy group having 3 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, or an aryloxy group having 6 to 40 carbon atoms; R6 represents an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, or a cycloalkyloxy group having 3 to 40 carbon atoms; Ar3, Ar5, and Ar7 each independently represent an arylene group or a heteroarylene group; Ar4, Ar6, and Ar8 each independently represent an aryl group or a heteroaryl group; a to d represent the number of R5, a represents an integer of 0 to 2, b represents an integer of 0 to 3; c represents an integer of 0 to 4; d represents an integer of 0 to 5.

[0024] [7] The composition for light-emitting diodes according to [5] or [6], wherein the high-molecular-weight compound is a copolymerized high-molecular-weight compound further comprising a repeating unit having one or more thermally crosslinkable structural units selected from the group consisting of thermally crosslinkable structural units represented by the following general formulas (4a) to (4z):

[0025] [ka] (In the formula, R5, R6, a, b, and c have the same meanings as in the general formulae (3a) to (3x).)

[0026] [8] The composition for light-emitting diodes according to any one of [1] to [7], wherein the high-molecular-weight compound is a high-molecular-weight compound containing a repeating unit having a substituted triarylamine structural unit represented by the following general formula (5) and a repeating unit having a linking structural unit represented by the following general formula (6), and has a weight-average molecular weight of 10,000 or more and less than 1,000,000 in terms of polystyrene:

[0027] [ka]

[0028] [ka] (wherein R5, R6, b, and c have the same meanings as in the general formulae (3a) to (3x), Q represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3.

[0029] [9] The composition for light-emitting diodes according to any one of [1] to [8], wherein the high molecular weight compound is a copolymer high molecular weight compound containing a repeating unit represented by the following formula (7):

[0030] [ka] (wherein R5, R6, b, and c have the same meanings as in the general formulae (3a) to (3x), Q1 represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3, m represents a mole fraction of 0.1 to 0.9. p represents a mole fraction of 0.1 to 0.9.

[0031]

[10] The composition for light-emitting diodes according to [1], which contains two or more high-molecular-weight compounds.

[0032]

[11] A composition for an organic electroluminescence device, comprising the composition for a light-emitting diode according to any one of [1] to

[10] .

[0033]

[12] An organic electroluminescence element having a pair of electrodes and at least one organic layer sandwiched between the electrodes, An organic electroluminescence device, wherein the organic layer is formed by depositing the composition for organic electroluminescence devices according to

[11] .

[0034]

[13] The organic electroluminescence device according to

[12] , wherein the organic layer is a hole transport layer.

[0035]

[14] The organic electroluminescence device according to

[12] , wherein the organic layer is an electron blocking layer.

[0036]

[15] The organic electroluminescence device according to

[12] , wherein the organic layer is a hole injection layer.

[0037]

[16] The organic electroluminescence device according to

[12] , wherein the organic layer is a light-emitting layer.

[0038] According to the present invention, it is possible to provide a composition for a light-emitting diode that can extend the life of an organic electroluminescent element. [Brief explanation of the drawings]

[0039] [Figure 1] FIG. 1 shows the chemical structures of compounds 1 to 16 suitable as thermally crosslinkable low molecular weight compounds used in the present invention. [Figure 2] FIG. 1 shows the chemical structures of compounds 17 to 26, which are suitable as thermally crosslinkable low molecular weight compounds used in the present invention. [Figure 3] FIG. 1 is a diagram showing the chemical structures of structural units 1 to 9 suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 4] FIG. 1 is a diagram showing the chemical structures of structural units 10 to 18 suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 5] FIG. 1 is a diagram showing the chemical structures of structural units 19 to 26 that are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 6] FIG. 2 is a diagram showing the chemical structures of structural units 27 to 32, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 7] FIG. 2 is a diagram showing the chemical structures of structural units 33 to 38, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 8] FIG. 2 is a diagram showing the chemical structures of structural units 39 to 47, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 9] FIG. 2 is a diagram showing the chemical structures of structural units 48 to 56, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 10] FIG. 2 is a diagram showing the chemical structures of structural units 57 to 68, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 11] FIG. 2 is a diagram showing the chemical structures of structural units 69 to 79, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 12] FIG. 1 is a diagram showing the chemical structures of structural units 80 to 88, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 13] FIG. 2 is a diagram showing the chemical structures of structural units 89 to 99, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 14] FIG. 1 is a diagram showing the chemical structures of structural units 100 to 108 suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 15] FIG. 1 is a diagram showing the chemical structures of structural units 109 to 117, which are suitable as triarylamine structural units of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 16] FIG. 1 is a diagram showing the chemical structures of structural units 118 to 126 that are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 17] FIG. 1 is a diagram showing the chemical structures of structural units 127 to 135, which are suitable as triarylamine structural units of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 18] FIG. 1 shows the chemical structures of structural units 136 to 144, which are suitable as triarylamine structural units of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 19] FIG. 1 is a diagram showing the chemical structures of structural units 145 to 156, which are suitable as the triarylamine structural unit of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 20] FIG. 1 is a diagram showing the chemical structures of structural units 157 to 165, which are suitable as triarylamine structural units of general formula (2) contained in the high molecular weight compound used in the present invention. [Figure 21] FIG. 2 is a diagram showing the chemical structures of structural units 201 to 220 suitable as linking structural units of general formula (6) contained in the high molecular weight compound used in the present invention. [Figure 22] FIG. 2 is a diagram showing the chemical structures of structural units 221 to 232 suitable as linking structural units of general formula (6) contained in the high molecular weight compound used in the present invention. [Figure 23] FIG. 1 is a diagram showing an example of a layer structure of an organic EL element of the present invention. [Figure 24] 1H-NMR chart of high molecular weight compound I synthesized in Example 1. [Figure 25] 1H-NMR chart of high molecular weight compound II synthesized in Example 2. DETAILED DESCRIPTION OF THE INVENTION

[0040] <Composition for light-emitting diodes> The composition for light-emitting diodes of the present invention includes a high-molecular-weight compound and a thermally crosslinkable low-molecular-weight compound. Here, the composition for light-emitting diodes refers to a composition that can constitute an organic layer of a light-emitting diode such as a quantum dot light-emitting device or an organic electroluminescence device.

[0041] <<Thermally crosslinkable low molecular weight compounds>> The thermally crosslinkable low molecular weight compound used in the present invention is a compound having two or more thermally crosslinkable structures in the molecule (hereinafter also referred to as compound A), which is a compound that forms a crosslinked structure with a high molecular weight compound having a thermally crosslinkable structural unit upon heating. Compound A is not particularly limited, but examples thereof include compounds having two or more thermally crosslinkable structures in the molecule selected from acrylate structures, methacrylate structures, and maleimide structures.

[0042] Examples of the compound A include compounds represented by the following general formula (1).

[0043] [ka] (Wherein, L1 is an arylene group, a heteroarylene group, an alkylene group, or a disulfide group; L2 is an arylene group, a heteroarylene group, a disulfide group, or a single bond; A may be the same or different and is a group selected from the following formulae A1, A2, and A3.

[0044] [ka] (In the formula, the dashed line represents the binding site.)

[0045] In the general formula (1), the arylene group is a divalent group and may be a single ring or a condensed ring. Examples of the arylene group include a phenylene group, a naphthylene group, an anthranylene group, a phenanthranylene group, a fluorenylene group, an indenylene group, a pyrenylene group, and a perylenylene group. These arylene groups may have a substituent.

[0046] In the general formula (1), the heteroarylene group is a divalent group and may be a single ring or a fused ring. Examples of the heteroarylene group include a pyridinylene group, a pyrimidinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzofuranylene group, a benzothiophenylene group, an indolylene group, a carbazolylene group, a benzoxazolylene group, a benzothiazolylene group, a quinoxalinylene group, a benzimidazolylene group, a pyrazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a naphthyridinylene group, a phenanthrolinylene group, an acridinylene group, and a carbolinylene group. These heteroarylene groups may have a substituent.

[0047] In the general formula (1), the alkylene group is not particularly limited, but may be a linear or branched alkylene group having 1 to 40 carbon atoms. Examples of the alkylene group include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, a sec-butylene group, a tert-butylene group, an n-hexylene group, an n-pentylene group, an isopentylene group, a neopentylene group, a sec-pentylene group, a tert-pentylene group, a 3-pentylene group, an n-octylene group, and an n-dodecylene group. These alkylene groups may have a substituent.

[0048] Examples of the substituent that the arylene group, heteroarylene group, and alkylene group in the general formula (1) may have include a deuterium atom, a cyano group, a nitro group, and the following groups. Halogen atoms: fluorine, chlorine, bromine and iodine atoms; Alkyl groups: in particular those having 1 to 8 carbon atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, n-heptyl, isoheptyl, neoheptyl, n-octyl, isooctyl and neooctyl; Alkyloxy groups: in particular those having 1 to 8 carbon atoms, methyloxy, ethyloxy, propyloxy, phenyloxy and tolyloxy groups; Alkenyl groups: vinyl and allyl groups; Aryl groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl and triphenyl groups; Heteroaryl groups: pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbolinyl groups; Aryl vinyl groups: styryl and naphthyl vinyl groups; Acyl groups: acetyl and benzoyl groups

[0049] These substituents may further have the substituents exemplified above. Furthermore, these substituents preferably exist independently of each other, but these substituents may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom, or a sulfur atom to form a ring.

[0050] In the general formula (1), it is preferable that L1 is a phenylene group, a naphthalene group, or a biphenylene group, and L2 is a single bond, or that L1 is an alkylene group having 2 to 6 carbon atoms, and L2 is a phenylene group or a naphthalene group. It is particularly preferable that L1 is a phenylene group, and L2 is a single bond, or that L1 is an alkylene group having 2 to 6 carbon atoms, and L2 is a phenylene group. These embodiments are particularly excellent in extending the life of the organic electroluminescence device.

[0051] <<High molecular weight compounds>> The high molecular weight compound used in the present invention may be a homopolymer or a copolymer. The high molecular weight compound is not particularly limited, and may contain, for example, a triarylamine structural unit, a structural unit represented by any of the general formulae (3a) to (3x), a thermally crosslinkable structural unit, and a linking structural unit, as described below, in the repeating unit. These structural units may form a repeating unit singly or in combination with a plurality of different structural units. It is preferable that the high molecular weight compound contains a repeating unit having a triarylamine structural unit, since this has good hole injection properties, high hole mobility, excellent electron blocking ability, a stable thin film state, and excellent heat resistance.

[0052] <<<Triarylamine structural unit>>> The triarylamine structural unit is preferably a structural unit represented by the following general formula (2).

[0053] [ka] (In the formula, Ar1 and Ar2 each independently represent an arylene group or a heteroarylene group, R3 and R4 each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms; X, Y, and Z each independently represent an aryl group, a heteroaryl group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms, provided that at least one of them is an aryl group or a heteroaryl group.

[0054] In the general formula (2), Ar1 and Ar2 each independently represent an arylene group or a heteroarylene group, and Ar1 and Ar2 may be the same group. The aromatic ring of the arylene group may be a single ring or a fused ring. Examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, an indene ring, a pyrene ring, and a perylene ring. The heterocyclic ring of the heteroarylene group may be a single ring or a fused ring. Examples of the heterocyclic ring include a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a benzofuran ring, a benzothiophene ring, an indole ring, a carbazole ring, a benzoxazole ring, a benzothiazole ring, a quinoxaline ring, a benzimidazole ring, a pyrazoline ring, a dibenzofuran ring, a dibenzothiophene ring, a naphthyridine ring, a phenanthroline ring, an acridine ring, and a carboline ring.

[0055] Ar1 and Ar2 may have a substituent, which may include a deuterium atom, a cyano group, a nitro group, and the following groups: Halogen atoms: fluorine, chlorine, bromine and iodine atoms; Alkyl groups: in particular those having 1 to 8 carbon atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, n-heptyl, isoheptyl, neoheptyl, n-octyl, isooctyl and neooctyl; Alkyloxy groups: in particular those having 1 to 8 carbon atoms, methyloxy, ethyloxy, propyloxy, phenyloxy and tolyloxy groups; Alkenyl groups: vinyl and allyl groups; Aryl groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl and triphenyl groups; Heteroaryl groups: pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbolinyl groups; Aryl vinyl groups: styryl and naphthyl vinyl groups; Acyl groups: acetyl and benzoyl groups These substituents may further have the substituents exemplified above.

[0056] The substituents that Ar1 and Ar2 may have are preferably present independently of each other, but these substituents may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom, or a sulfur atom to form a ring.

[0057] Ar1 and Ar2 are preferably naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothienyl, or substituted fluorenyl, and most preferably unsubstituted phenyl. Suitable substituents on the fluorenyl include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and phenyl.

[0058] In the general formula (2), R3 and R4 each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms, and R3 and R4 may be the same as each other.

[0059] Examples of the alkyl group, cycloalkyl group, alkenyl group, alkyloxy group and cycloalkyloxy group include the following groups. Alkyl groups (C1-C8): methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and n-octyl; Cycloalkyl groups (C5-C 10 ): cyclopentyl, cyclohexyl, 1-adamantyl and 2-adamantyl groups; Alkenyl groups (C2-C6): vinyl, allyl, isopropenyl and 2-butenyl; Alkyloxy groups (C1-C6): methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentyloxy and n-hexyloxy; Cycloalkyloxy group (C5-C 10 ): cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, 1-adamantyloxy, and 2-adamantyloxy groups

[0060] R3 and R4 may have a substituent. These substituents are the same as the substituents that Ar1 and Ar2 may have, and these substituents may also have further substituents. The substituents that R3 and R4 may have are preferably present independently of each other, but may be bonded to each other to form a ring, similar to the substituents that Ar1 and Ar2 may have.

[0061] R3 and R4 are preferably a hydrogen atom and a deuterium atom, and from the viewpoint of synthesis, a hydrogen atom is most suitable.

[0062] In the general formula (2), X, Y, and Z may be the same as one another, and each independently represents an aryl group, a heteroaryl group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms, provided that at least one of them is an aryl group or a heteroaryl group.

[0063] Examples of the alkyl group, cycloalkyl group, alkenyl group, alkyloxy group, and cycloalkyloxy group include the same groups as those exemplified above for R3 and R4. Examples of the aryl group and heteroaryl group include the following groups. Aryl groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenyl, fluorenyl, indenyl, pyrenyl, perylenyl and fluoranthenyl groups; Heteroaryl groups: pyridyl, pyrimidinyl, triazinyl, furyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, and carbolinyl groups

[0064] Furthermore, X, Y, and Z may have a substituent. These substituents are the same as the substituents that Ar1 and Ar2 may have, and these substituents may also have a further substituent. For example, the aryl group or heteroaryl group may have a phenyl group as a substituent, and the phenyl group may further have a phenyl group as a substituent. That is, when the aryl group is a phenyl group, the aryl group may be a biphenylyl group or a terphenylyl group.

[0065] The above-mentioned substituents that X, Y and Z may have may exist independently, or may be bonded to each other or to X, Y or Z to form a ring.

[0066] Specific examples of the substituted triarylamine structural unit represented by the above-mentioned general formula (2), which is a structural unit of a high molecular weight compound, are shown in Figures 3 to 20 as structural units 1 to 165. In the chemical formulae shown in Figures 3 to 20, dashed lines indicate bonds to adjacent structural units.

[0067] <<<Structural units represented by general formulas (3a) to (3x)>>> The high molecular weight compound may contain a repeating unit having one or more structural units selected from the group consisting of structural units represented by the following general formulas (3a) to (3x).

[0068] [ka] (wherein R5 represents a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, a cycloalkyloxy group having 3 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, or an aryloxy group having 6 to 40 carbon atoms; R6 represents an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, or a cycloalkyloxy group having 3 to 40 carbon atoms; Ar3, Ar5, and Ar7 each independently represent an arylene group or a heteroarylene group; Ar4, Ar6, and Ar8 each independently represent an aryl group or a heteroaryl group; a to d represent the number of R5, a represents an integer of 0 to 2, b represents an integer of 0 to 3; c represents an integer of 0 to 4; d represents an integer of 0 to 5.

[0069] Examples of the alkyl group, alkyloxy group, cycloalkyl group, cycloalkyloxy group, alkenyl group and aryloxy group represented by R5 in the general formulae (3a) to (3x) include the following groups. Alkyl groups (having 1 to 8 carbon atoms): methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, n-heptyl, isoheptyl, neoheptyl, n-octyl, isooctyl, and neooctyl; Alkyloxy groups (having 1 to 8 carbon atoms): methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, n-heptyloxy group, and n-octyloxy group; Cycloalkyl groups (having 5 to 10 carbon atoms): cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, and the like. Cycloalkyloxy groups (having 5 to 10 carbon atoms): cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, and 2-adamantyloxy group; Alkenyl groups (having 2 to 6 carbon atoms): vinyl groups, allyl groups, isopropenyl groups, 2-butenyl groups, and the like. Aryloxy groups: phenyloxy and tolyloxy groups

[0070] Examples of the alkyl group, alkyloxy group, cycloalkyl group, and cycloalkyloxy group represented by R6 in the general formulae (3a) to (3x) include the same groups as those exemplified for R5. R6 is most preferably an n-hexyl group or an n-octyl group in order to enhance solubility.

[0071] Examples of the arylene group and heteroarylene group represented by Ar3, Ar5, and Ar7 in the general formulae (3a) to (3x) include a phenylene group, a naphthylene group, an anthranylene group, a phenanthranylene group, a fluorenylene group, an indenylene group, a pyrenylene group, a perylenylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzofuranylene group, a benzothiophenylene group, an indolylene group, a carbazolylene group, a benzoxazolylene group, a benzothiazolylene group, a quinoxalinylene group, a benzimidazolylene group, a pyrazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a naphthyridinylene group, a phenanthrolinylene group, an acridinylene group, and a carbolinylene group.

[0072] Examples of the aryl group and heteroaryl group represented by Ar4, Ar6, and Ar8 in the general formulae (3a) to (3x) include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a furyl group, a pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group. <<<Thermal crosslinkable structural unit>>> The high molecular weight compound may contain a repeating unit having one or more thermally crosslinkable structural units selected from the group consisting of thermally crosslinkable structural units represented by the following general formulas (4a) to (4z): The thermally crosslinkable structural unit refers to a structural unit that forms a crosslinked structure by heat.

[0073] [ka] (In the formula, R5, R6, a, b, and c have the same meanings as in the general formulae (3a) to (3x).)

[0074] In the general formulae (4a) to (4z), R6 is preferably an n-hexyl group or an n-octyl group in order to enhance solubility.

[0075] <<<Triarylamine structural units and linking structural units>>> The high molecular weight compound may contain a repeating unit having a triaryl structural unit represented by the following general formula (5) and a repeating unit having a linking structural unit represented by the following general formula (6). The repeating unit may contain only one of the structural units or may contain both structural units, but it is preferable that the repeating unit contains both.

[0076] [ka]

[0077] [ka] (wherein R5, R6, b, and c have the same meanings as in the general formulae (3a) to (3x), Q represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3.

[0078] In the general formulae (5) and (6), R5 is preferably a hydrogen atom or a deuterium atom, and from the viewpoint of synthesis, it is most preferably a hydrogen atom.

[0079] In the general formula (5), R6 is most preferably an n-hexyl group or an n-octyl group in order to enhance solubility.

[0080] In the general formula (6), Q represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group. Examples of the above aryl group and heteroaryl group include the following groups. Aryl groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl and fluoranthenyl groups; Heteroaryl groups: pyridyl, pyrimidinyl, triazinyl, furyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, indenocarbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, and carbolinyl groups

[0081] The amino group, aryl group, and heteroaryl group may have a substituent, which may include a deuterium atom, a cyano group, a nitro group, and the following groups: Halogen atoms: fluorine, chlorine, bromine and iodine atoms; Alkyl groups: in particular those having 1 to 8 carbon atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, n-heptyl, isoheptyl, neoheptyl, n-octyl, isooctyl and neooctyl; Alkyloxy groups: in particular those having 1 to 8 carbon atoms, methyloxy, ethyloxy, propyloxy, phenyloxy and tolyloxy groups; Alkenyl groups: vinyl and allyl groups; Aryl groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl and triphenyl groups; Heteroaryl groups: pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbolinyl groups; Aryl vinyl groups: styryl and naphthyl vinyl groups; Acyl groups: acetyl and benzoyl groups

[0082] These substituents may further have the substituents exemplified above. Furthermore, these substituents preferably exist independently of each other, but these substituents may be bonded to each other via a single bond, a methylene group which may have a substituent, an oxygen atom, or a sulfur atom to form a ring.

[0083] For example, the aryl group or heteroaryl group may have a phenyl group as a substituent, and the phenyl group may further have a phenyl group as a substituent, i.e., taking the aryl group as an example, the aryl group may be a biphenylyl group, a terphenylyl group, or a triphenylenyl group.

[0084] In the general formula (5), L3 represents a phenylene group, and n represents an integer of 0 to 3.

[0085] Furthermore, the above L3 may have a substituent. The substituent is the same as the substituent that the above Q may have, and these substituents may further have a substituent.

[0086] In the present invention, specific examples of the linking structural unit represented by the above-mentioned general formula (6) are shown as structural units 201 to 232 in Figures 21 and 22. In the chemical formulae shown in Figures 21 and 22, dashed lines indicate bonds to adjacent structural units. Although preferred specific examples of the linking structural unit are shown, the linking structural unit possessed by the high molecular weight compound used in the present invention is not limited to these structural units.

[0087] The high molecular weight compound is preferably a copolymer high molecular weight compound containing a repeating unit represented by the following general formula (7).

[0088] [ka] (wherein R5, R6, b, and c have the same meanings as in the general formulae (3a) to (3x), Q1 represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3, m represents a mole fraction of 0.1 to 0.9. p represents a mole fraction of 0.1 to 0.9.

[0089] In the general formula (7), m and p represent the molar fraction in the repeating unit, m is preferably 0.2 to 0.8, and p is preferably 0.3 to 0.7.

[0090] In the general formula (7), examples of the aryl group and heteroaryl group represented by Q1 include the same as those of Q represented by the general formula (6).

[0091] <<<Preferred structural units>>> The high molecular weight compound preferably contains a repeating unit having structural units represented by the general formula (2) and the general formula (3a), more preferably a repeating unit having structural units represented by the general formula (3a) and the general formula (4e), and also preferably a repeating unit having structural units represented by the general formula (7), more preferably a repeating unit having structural units represented by the general formula (6) and the general formula (4e).

[0092] <<<Weight average molecular weight>>> The weight average molecular weight of the high molecular weight compound, measured by GPC in terms of polystyrene, is preferably in the range of 10,000 or more and less than 1,000,000, more preferably 10,000 or more and less than 500,000, and even more preferably 10,000 or more and less than 200,000.

[0093] <<<Synthesis method>>> The high molecular weight compound is synthesized by linking each structural unit through the Suzuki polymerization reaction or the Hartwig-Buchwald polymerization reaction to form a C—C bond or a C—N bond, respectively. Specifically, a unit compound having each structural unit is prepared, and the unit compound is appropriately borated or halogenated, followed by a polycondensation reaction using a catalyst, whereby the high molecular weight compound can be synthesized.

[0094] For example, a triarylamine derivative represented by the following general formula (2a) can be used as a compound for introducing the structural unit of general formula (2).

[0095] [ka] (In the formula, Q2 is a hydrogen atom or a halogen atom (particularly Br), and Ar1, Ar2, X, Y, Z, R3, and R4 are all the same as those in the general formula (2).)

[0096] In the general formula (2a), a compound in which Q2 is a hydrogen atom is a unit compound for introducing a triarylamine structural unit represented by the general formula (2), and a compound in which Q2 is a halogen atom is a halide used to synthesize a polymer.

[0097] For example, a terpolymer containing 40 mol% of structural units represented by general formula (2) (structural unit A), 50 mol% of structural units represented by general formula (3a) (structural unit B), and 10 mol% of structural units represented by general formula (4e) (structural unit C) is represented by the following general formula (8). That is, this terpolymer is a copolymer containing 80 mol% of repeating units consisting of structural unit A and structural unit B, and 20 mol% of repeating units consisting of structural unit C and structural unit B.

[0098] [ka]

[0099] When the intermediate for introducing the structural unit A and the structural unit C is a halogenated compound, the intermediate for introducing the structural unit B is a borate esterified compound. Alternatively, when the intermediate for introducing the structural unit A and the structural unit C is a borate esterified compound, the intermediate for introducing the structural unit B is a halogenated compound. In other words, the molar ratio of the halogenated compound to the borate esterified compound must be equal.

[0100] Furthermore, for example, a terpolymer containing 40 mol% of structural units represented by general formula (5) (structural unit D), 50 mol% of structural units represented by general formula (6) (structural unit E), and 10 mol% of structural units represented by general formula (4e) (structural unit C) is represented by the following general formula (9). That is, this terpolymer is a copolymer containing 80 mol% of repeating units consisting of structural units D and E, and 20 mol% of repeating units consisting of structural units C and E.

[0101] [ka]

[0102] When the intermediate for introducing the structural unit D and the structural unit C is a borate ester, the intermediate for introducing the structural unit E is a halogenated product. Alternatively, when the intermediate for introducing the structural unit D and the structural unit C is a halogenated product, the intermediate for introducing the structural unit E is a borate ester. In other words, the molar ratio of the halogenated product to the borate ester must be equal.

[0103] <<Solvent>> The composition for light-emitting diodes of the present invention may contain a solvent, such as an aromatic organic solvent, for example, benzene, toluene, xylene, or anisole.

[0104] <<Film forming method>> The composition for light-emitting diodes is dissolved in an aromatic organic solvent such as benzene, toluene, xylene, or anisole to prepare a mixed coating solution, which is then coated on a predetermined substrate and dried by heating, thereby forming a thin film having excellent properties such as hole injection, hole transport, and electron blocking properties. The thin film thus obtained has good heat resistance and also good adhesion to other layers.

[0105] <<Organic layer>> The composition for light-emitting diodes can be used as a constituent material for a hole injection layer and / or a hole transport layer of an organic EL device. The hole injection layer and hole transport layer formed from the composition for light-emitting diodes can realize the advantage of improving the durability of the organic EL device compared to those formed from conventional high-molecular-weight compounds alone. The composition for light-emitting diodes can also be suitably used to form an electron blocking layer or a light-emitting layer.

[0106] <<Preferred uses of compositions for light-emitting diodes>> The composition for light-emitting diodes of the present invention is particularly preferably used as a composition for organic electroluminescence devices. Here, the composition for organic electroluminescence devices refers to a composition that can constitute an organic layer of an organic electroluminescence device.

[0107] <Organic EL element> The organic electroluminescent device of the present invention, which includes an organic layer formed using the composition for light-emitting diodes, has a structure, for example, as shown in Fig. 23. That is, a transparent anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, and a cathode 7 are provided on a glass substrate 1. The glass substrate 1 can also be replaced with another transparent substrate, such as a transparent resin substrate.

[0108] The organic EL device is not limited to the layer structure described above. A hole-blocking layer may be provided between the light-emitting layer 5 and the electron-transporting layer 6, or an electron-blocking layer may be provided between the hole-transporting layer 4 and the light-emitting layer 5. Furthermore, an electron-injection layer may be provided between the cathode 7 and the electron-transporting layer 6. Furthermore, some layers may be omitted. For example, a simple layer structure may be used in which an anode 2, a hole-transporting layer 4, a light-emitting layer 5, an electron-transporting layer 6, and a cathode 7 are provided on a substrate 1. Alternatively, a two-layer structure may be formed by stacking layers having the same function.

[0109] The composition for light-emitting diodes is suitably used for forming an organic layer provided between the anode 2 and the cathode 7, such as the hole injection layer 3, the hole transport layer 4, the light-emitting layer 5, or an electron blocking layer (not shown), by taking advantage of its properties such as hole injection property and hole transport property.

[0110] In the organic EL element, the transparent anode 2 may be formed from a known electrode material, and is formed by depositing an electrode material with a large work function, such as ITO or gold, on a transparent substrate such as a glass substrate.

[0111] The hole injection layer 3 provided on the transparent anode 2 can be formed using a coating liquid prepared by dissolving the composition for light-emitting diodes in an aromatic organic solvent such as toluene, xylene, or anisole. For example, the hole injection layer 3 can be formed by coating the transparent anode 2 with this coating liquid by spin coating, inkjet printing, or the like.

[0112] Alternatively, the hole injection layer 3 can be formed using conventionally known materials, such as the following materials, without using the high molecular weight compound. Porphyrin compounds, such as copper phthalocyanine; Starburst triphenylamine derivatives; arylamines having structures linked by arylene groups that do not contain single bonds or heteroatoms (e.g., triphenylamine trimers and tetramers); Acceptor heterocyclic compounds such as hexacyanoazatriphenylene; Coating-type polymeric materials, such as poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(styrene sulfonate) (PSS) Formation of a layer (thin film) using such a material can be carried out by coating using a vapor deposition method, a spin coating method, an inkjet method, etc. Layer formation is similar for other layers, and is carried out by a vapor deposition method or a coating method depending on the type of film-forming material.

[0113] Like the hole injection layer 3, the hole transport layer 4 provided on the hole injection layer 3 can also be formed by coating using a coating liquid in which the composition for light-emitting diodes is dissolved, such as by spin coating or inkjet coating.

[0114] Alternatively, a conventionally known hole transport material can be used to form the hole transport layer 4. Representative examples of such hole transport materials include the following. Benzidine derivatives, for example, N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter abbreviated as TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (hereinafter abbreviated as NPD), and N,N,N',N'-tetrabiphenylylbenzidine. Amine derivatives, for example, 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC). Various triphenylamine trimers and tetramers. A coating-type polymer material that is also used for hole injection layers.

[0115] The compounds for the hole transport layer described above, including the high molecular weight compounds, may be used alone or in combination to form a film. Alternatively, a multilayer film formed by laminating multiple layers using one or more of the compounds may be used as the hole transport layer.

[0116] Furthermore, a layer that serves as both the hole injection layer 3 and the hole transport layer 4 may be used, and such a hole injection / transport layer can be formed by coating using a polymer material such as PEDOT.

[0117] The hole transport layer 4 (and the hole injection layer 3) may be formed by doping a material typically used for the layer with P, such as trisbromophenylaminehexachloroantimony or a radialene derivative (see, for example, WO2014 / 009310).The hole transport layer 4 (or the hole injection layer 3) may also be formed using a polymer compound having a TPD basic skeleton.

[0118] An electron blocking layer (not shown) (which can be provided between the hole transport layer 4 and the light emitting layer 5) can also be formed by spin coating or inkjet coating using a coating liquid in which the composition for light emitting diodes is dissolved, similar to the hole transport layer 4.

[0119] The electron blocking layer can also be formed using a known electron blocking compound having an electron blocking effect, such as a carbazole derivative, a compound having a triphenylsilyl group and a triarylamine structure, etc. Specific examples of carbazole derivatives and compounds having a triarylamine structure are as follows: Carbazole derivatives, such as 4,4',4''-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), and 2,2-bis[4-(carbazol-9-yl)phenyl]adamantane (hereinafter abbreviated as Ad-Cz). Compounds having a triarylamine structure, for example, 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene.

[0120] The electron blocking layer is formed using the above-mentioned known electron blocking materials alone or in combination of two or more types. However, it is also possible to form multiple layers using one or more of these electron blocking materials, and to form a multilayer film by stacking such layers.

[0121] The light-emitting layer 5 of the organic EL element can be formed using light-emitting materials such as metal complexes of quinolinol derivatives such as Alq3, as well as various metal complexes of zinc, beryllium, aluminum, etc., anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylenevinylene derivatives.

[0122] The light-emitting layer 5 can also be composed of a host material and a dopant material. In this case, in addition to the above-mentioned light-emitting materials, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, etc. can be used as the host material, and further, the above-mentioned high molecular weight compounds can be used alone or in combination. As the dopant material, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, etc. can be used.

[0123] Such a light-emitting layer 5 may also have a single layer structure using one or more types of light-emitting materials, or may have a multilayer structure in which a plurality of layers are laminated.

[0124] Furthermore, the light-emitting layer 5 can also be formed using a phosphorescent material as the light-emitting material.

[0125] The phosphorescent material may be a metal complex phosphorescent material such as iridium or platinum. For example, green phosphorescent materials such as Ir(ppy)3, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp2Ir(acac) can be used. These phosphorescent materials are used by doping into hole-injecting / transporting host materials or electron-transporting host materials.

[0126] Examples of the hole-injecting / transporting host material include carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (hereinafter abbreviated as CBP), TCTA, and mCP, and also include the high-molecular-weight compounds mentioned above.

[0127] Examples of electron-transporting host materials that can be used include p-bis(triphenylsilyl)benzene (hereinafter abbreviated as UGH2) and 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI).

[0128] In order to avoid concentration quenching, the phosphorescent light-emitting material is preferably doped into the host material by co-evaporation in an amount ranging from 1 to 30 weight percent based on the entire light-emitting layer.

[0129] It is also possible to use materials that emit delayed fluorescence, such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, as light-emitting materials (see Appl. Phys. Let., 98, 083302 (2011)).

[0130] By forming the light-emitting layer 5 by loading a fluorescent light-emitting material, a phosphorescent light-emitting material, or a material that emits delayed fluorescence, which is called a dopant, on the high molecular weight compound, an organic EL element with a reduced driving voltage and improved luminous efficiency can be realized.

[0131] The hole blocking layer (not shown) provided between the light emitting layer 5 and the electron transporting layer 6 can be formed using a known compound having a hole blocking effect.

[0132] Examples of known compounds having such hole blocking properties include the following: Phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP); metal complexes of quinolinol derivatives such as aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (hereinafter abbreviated as BAlq); various rare earth complexes; triazole derivatives; triazine derivatives; oxadiazole derivatives. These materials can also be used to form the electron transport layer 6 described below, and can also be used as such a hole blocking layer and electron transport layer 6.

[0133] Such a hole-blocking layer may also have a single layer or a multi-layer laminate structure, and each layer is formed using one or more of the above-mentioned compounds having hole-blocking properties.

[0134] The electron transport layer 6 is formed using a known electron transport compound, such as a metal complex of a quinolinol derivative such as Alq3 or BAlq, as well as various metal complexes, pyridine derivatives, pyrimidine derivatives, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silole derivatives, and benzimidazole derivatives.

[0135] This electron transport layer 6 may also have a single layer or a multi-layer laminate structure, and each layer is formed using one or more of the above-mentioned electron transport compounds.

[0136] Furthermore, an electron injection layer (not shown) that is provided as needed can also be formed using a known material, for example, an alkali metal salt such as lithium fluoride or cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, a metal oxide such as aluminum oxide, or an organometallic complex such as lithium quinoline.

[0137] The cathode 7 of the organic EL element is made of an electrode material having a low work function such as aluminum, or an alloy having an even lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy.

[0138] In the present invention, an organic EL device having high luminous efficiency and power efficiency, low practical driving voltage, and extremely excellent durability can be obtained by forming at least one of the hole injection layer 3, hole transport layer 4, light-emitting layer 5, and electron blocking layer (not shown) using a composition for light-emitting diodes. In particular, an organic EL device having a hole transport layer 4 formed using the composition for light-emitting diodes has high luminous efficiency, a reduced driving voltage, improved current resistance, and an increased maximum luminance. [Example]

[0139] The present invention will now be described with reference to the following experimental examples. For details of the synthesis for producing the high molecular weight compound containing the structural unit represented by general formula (2) used in the present invention, see WO2018 / 168667.

[0140] Example 1 Synthesis of high molecular weight compound I; The following components were added to a reaction vessel whose atmosphere had been replaced with nitrogen, and nitrogen gas was bubbled through the vessel for 30 minutes. 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di-n-octylfluorene: 6.5g N,N-bis(4-bromophenyl)-4-(2-naphthalenyl)-[1,1':2',1''-terphenyl]-4'-amine: 5.5g N,N-bis(4-bromophenyl)-bicyclo[4.2.0]octa-1,3,5-trien-3-amine: 0.87g Tripotassium phosphate: 9.0g Toluene: 16 ml Water: 9ml 1,4-dioxane: 48 ml Next, 1.9 mg of palladium(II) acetate and 15.0 mg of tri-o-tolylphosphine were added, heated, and stirred at 88°C for 10 hours. 22 mg of phenylboronic acid was then added and stirred for 1 hour, followed by 0.32 g of bromobenzene and stirring for 1 hour. 100 ml of toluene and 100 ml of 5 wt% aqueous sodium N,N-diethyldithiocarbamate solution were added, heated, and stirred under reflux for 2 hours. After cooling to room temperature, saturated brine and toluene were added, and the organic layer was separated and collected. The organic layer was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude polymer. The crude polymer was dissolved in toluene, silica gel was added for adsorption purification, and the silica gel was removed by filtration. The resulting filtrate was concentrated under reduced pressure, and the dried product was dissolved in 300 ml of toluene. This was then added dropwise to 600 ml of n-hexane, and the resulting precipitate was collected by filtration. This procedure was repeated three times and dried to obtain 8.3 g of high molecular weight compound I (yield 93%).

[0141] The average molecular weight and dispersity of the high molecular weight compound I measured by GPC were as follows: Number average molecular weight Mn (polystyrene equivalent): 55,000 Weight average molecular weight Mw (polystyrene equivalent): 120,000 Dispersity (Mw / Mn): 2.2

[0142] Furthermore, NMR measurements were carried out on the high molecular weight compound I. 1 The results of H-NMR measurement are shown in Figure 24. The chemical formula was as follows:

[0143] [ka]

[0144] As can be seen from the above chemical composition, this high molecular weight compound I contained 40 mol % of structural units A represented by general formula (2), 50 mol % of structural units B represented by general formula (3a), and further contained 10 mol % of structural units C represented by general formula (4e).

[0145] <Example 2> Synthesis of high molecular weight compound II; The following components were added to a reaction vessel whose atmosphere had been replaced with nitrogen, and nitrogen gas was bubbled through the vessel for 30 minutes. 9,9-Dioctyl-N,N-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-fluoren-2-amine: 5.0 g 1,3-dibromobenzene: 1.8g N,N-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]bicyclo[4.2.0]octa-1,3,5-trien-3-amine: 0.8g Tripotassium phosphate: 6.9g Toluene: 9 ml Water: 5ml 1,4-dioxane: 27 ml Next, 1.4 mg of palladium(II) acetate and 11.5 mg of tri-o-tolylphosphine were added, heated, and stirred at 87°C for 14 hours. After this, 17 mg of phenylboronic acid was added and stirred for 1 hour, followed by 242 mg of bromobenzene and stirring for 1 hour. 50 mL of toluene and 50 mL of a 5 wt% aqueous solution of sodium N,N-diethyldithiocarbamate were added, heated, and stirred under reflux for 2 hours. After cooling to room temperature, the organic layer was separated and washed three times with saturated brine. The organic layer was dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude polymer. The crude polymer was dissolved in toluene, silica gel was added, and the mixture was purified by adsorption. The silica gel was removed by filtration. The resulting filtrate was concentrated under reduced pressure, and the dried product was dissolved in 100 mL of toluene. The solution was then added dropwise to 300 mL of n-hexane, and the resulting precipitate was collected by filtration. This procedure was repeated three times and dried to obtain 3.5 g of high molecular weight compound II (78% yield).

[0146] The average molecular weight and dispersity of the high molecular weight compound II measured by GPC were as follows: Number average molecular weight Mn (polystyrene equivalent): 32,000 Weight average molecular weight Mw (polystyrene equivalent): 55,000 Dispersity (Mw / Mn): 1.7

[0147] Furthermore, NMR measurement was carried out on the high molecular weight compound II. 1 The results of H-NMR measurement are shown in Figure 25. The chemical formula was as follows:

[0148] [ka]

[0149] As can be seen from the above chemical composition, this high molecular weight compound II contained 40 mol % of the structural unit D represented by general formula (5), 50 mol % of the structural unit E represented by general formula (6), and further contained 10 mol % of the structural unit C represented by general formula (4e).

[0150] Example 3 Fabrication and evaluation of organic light-emitting diodes; An organic EL device having the layer structure shown in FIG. 23 was fabricated by the following method. A glass substrate 1 on which a 50 nm thick ITO film was formed was washed with an organic solvent, and then the ITO surface was cleaned by UV / ozone treatment. A 50 nm thick PEDOT / PSS (manufactured by HERAEUS) film was formed by spin coating to cover the transparent anode 2 (ITO) provided on this glass substrate 1, and dried on a hot plate at 200°C for 10 minutes to form a hole injection layer 3.

[0151] The high molecular weight compound I obtained in Example 1 and compound 1 as a thermally crosslinkable low molecular weight compound were mixed in an amount 2.5 times the amount of structural unit C contained in high molecular weight compound I, and the mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution. The substrate on which the hole injection layer 3 had been formed as described above was transferred into a glove box purged with dry nitrogen and dried on a hot plate at 230°C for 10 minutes. Then, a coating layer having a thickness of 25 nm was formed on the hole injection layer 3 by spin coating using the coating solution, and the resultant was further dried on a hot plate at 220°C for 30 minutes to form a hole transport layer 4.

[0152] [ka]

[0153] The substrate on which the hole transport layer 4 was formed as described above was placed in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less. On the hole transport layer 4, an emitting layer 5 having a thickness of 34 nm was formed by binary deposition of a blue emitting material (EMD-1) having the following structural formula and a host material (EMH-1). In the binary deposition, the deposition rate ratio of EMD-1:EMH-1 was 4:96.

[0154] [ka]

[0155] On the light-emitting layer 5 formed as described above, an electron transport layer 6 having a thickness of 20 nm was formed by binary vapor deposition of electron transport materials (ETM-1) and (ETM-2) having the following structural formulas. In the binary vapor deposition, the vapor deposition rate ratio of ETM-1:ETM-2 was 50:50.

[0156] [ka]

[0157] Finally, aluminum was evaporated onto the electron transport layer 6 formed as described above to a thickness of 100 nm to form a cathode 7 .

[0158] The glass substrate thus fabricated, on which the transparent anode 2, hole injection layer 3, hole transport layer 4, light-emitting layer 5, electron transport layer 6, and cathode 7 were formed, was transferred into a glove box purged with dry nitrogen, and another glass substrate for sealing was attached using a UV-curable resin to form an organic EL device. The characteristics of the fabricated organic EL device were measured in air at room temperature. The light-emitting characteristics of the fabricated organic EL device were also measured when a DC voltage was applied. The results of the above measurements are shown in Table 1.

[0159] Example 4 An organic EL device was produced in the same manner as in Example 3, except that the applied layer of the hole transport layer 4 was formed by heating and drying on a hot plate at 220° C. for 30 minutes. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0160] <Example 5> An organic EL device was fabricated in the same manner as in Example 3, except that the high molecular weight compound II obtained in Example 2 was used instead of the high molecular weight compound I, and a coating solution was prepared by mixing compound 1 as a thermally crosslinkable low molecular weight compound in an amount equal to the amount of substance of structural unit C contained in high molecular weight compound II and dissolving the mixture in toluene at 0.6 wt % to form a hole transport layer 4. The organic EL device was evaluated for various properties, and the results are shown in Table 1.

[0161] Example 6 An organic EL device was fabricated in the same manner as in Example 3, except that high molecular weight compound II was used instead of high molecular weight compound I, compound 1 was mixed as a thermally crosslinkable low molecular weight compound in an amount equal to the amount of structural unit C contained in high molecular weight compound II, and the resulting mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution, which was then coated with the coating solution and dried by heating on a hot plate at 220°C for 30 minutes. The various properties of this organic EL device were evaluated, and the results are shown in Table 1.

[0162] Example 7 An organic EL device was fabricated in the same manner as in Example 3, except that high molecular weight compound II was used instead of high molecular weight compound I, compound 3 was mixed as a thermally crosslinkable low molecular weight compound in an amount equal to the amount of structural unit C contained in high molecular weight compound II, and the resulting mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution, which was then coated with the coating solution and dried by heating on a hot plate at 220°C for 30 minutes. The various properties of this organic EL device were evaluated, and the results are shown in Table 1.

[0163] [ka]

[0164] Example 8 An organic EL device was fabricated in the same manner as in Example 3, except that high molecular weight compound II was used instead of high molecular weight compound I, and compound 26 was mixed as a thermally crosslinkable low molecular weight compound in an amount equal to the amount of structural unit C contained in high molecular weight compound II, and the resulting mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution, which was then coated and dried on a hot plate at 220°C for 30 minutes. The various properties of this organic EL device were evaluated, and the results are shown in Table 1.

[0165] [ka]

[0166] Example 9 An organic EL device was fabricated in the same manner as in Example 3, except that a mixture of high molecular weight compound I and high molecular weight compound II in a weight ratio of 3:2 was used instead of high molecular weight compound I, and compound 1 was mixed as the thermally crosslinkable low molecular weight compound in an amount equal to the amount of structural unit C contained in high molecular weight compound I and high molecular weight compound II, and the mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution, and a hole transport layer 4 was formed using the coating solution. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0167] Example 10 An organic EL device was fabricated in the same manner as in Example 3, except that a mixture of high molecular weight compound I and high molecular weight compound II in a weight ratio of 3:2 was used instead of high molecular weight compound I, and compound 1 was mixed as the thermally crosslinkable low molecular weight compound in an amount equal to the amount of structural unit C contained in high molecular weight compound I and high molecular weight compound II, and the resulting mixture was dissolved in toluene at 0.6 wt % to prepare a coating solution. The hole transport layer 4 was then coated using the coating solution and dried by heating on a hot plate at 220°C for 30 minutes. The various properties of this organic EL device were evaluated, and the results are shown in Table 1.

[0168] <Comparative Example 1> An organic EL device was produced in the same manner as in Example 3, except that the hole transport layer 4 was formed using a coating solution prepared by dissolving only the high molecular weight compound I in toluene at 0.6 wt % without adding any thermally crosslinkable low molecular weight compound. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0169] <Comparative Example 2> An organic EL device was fabricated in the same manner as in Example 3, except that the hole transport layer 4 was formed by coating a coating solution prepared by dissolving only the high molecular weight compound I in toluene at 0.6 wt % without adding a thermally crosslinkable low molecular weight compound, and then drying the layer by heating on a hot plate at 220°C for 30 minutes. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0170] <Comparative Example 3> An organic EL device was fabricated in the same manner, except that the hole transport layer 4 was formed using a coating solution prepared by dissolving only high molecular weight compound II in toluene at 0.6 wt % instead of high molecular weight compound I, without adding a thermally crosslinkable low molecular weight compound. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0171] <Comparative Example 4> An organic EL device was fabricated in the same manner as in Example 3, except that the hole transport layer 4 was formed by applying a coating solution prepared by dissolving only high molecular weight compound II in toluene at 0.6 wt % instead of high molecular weight compound I without adding a thermally crosslinkable low molecular weight compound, and then drying the applied coating solution at 220°C for 30 minutes on a hot plate. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0172] <Comparative Example 5> An organic EL device was fabricated in the same manner as in Example 3, except that no thermally crosslinkable low-molecular-weight compound was added, and instead of high-molecular-weight compound I, a coating liquid was prepared by dissolving a mixture of high-molecular-weight compound I and high-molecular-weight compound II in a weight ratio of 3:2 in toluene at 0.6 wt % to form a hole-transport layer 4. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0173] <Comparative Example 6> An organic EL device was fabricated in the same manner as in Example 3, except that no thermally crosslinkable low-molecular-weight compound was added, and instead of high-molecular-weight compound I, a mixture of high-molecular-weight compound I and high-molecular-weight compound II was mixed in a weight ratio of 3:2, which was dissolved in toluene at 0.6 wt % to prepare a coating solution, which was then coated with the coating solution and dried by heating on a hot plate at 220°C for 30 minutes. Various characteristics of this organic EL device were evaluated, and the results are shown in Table 1.

[0174] In evaluating various characteristics, the device life is measured when the luminance at the start of light emission (initial luminance) is 700 cd / m 2 When driven at a constant current, the luminance was 560 cd / m 2The time it took for the brightness to decay to 80% (corresponding to 80% of the initial brightness taken as 100%) was measured.

[0175] [Table 1]

[0176] As shown in Table 1, a current density of 10 mA / cm 2 The driving voltage when a current of 100 kJ / s was passed was lower in the organic EL element of the Example to which the thermally crosslinkable low molecular weight compound was added than in the organic EL element of the Comparative Example. Also, the element lifetime (80% decay) was longer in the organic EL element of the Example to which the thermally crosslinkable low molecular weight compound was added than in the organic EL element of the Comparative Example.

[0177] As described above, it was found that an organic EL element having an organic layer formed by depositing the composition for light-emitting diodes of the present invention can achieve lower voltage and longer life while maintaining high efficiency compared to conventional organic EL elements. [Industrial Applicability]

[0178] The organic EL device of the present invention has a low driving voltage and a long life, and therefore can be used in, for example, home electrical appliances and lighting.

Claims

1. A composition for a light-emitting diode, comprising a high-molecular-weight compound and a thermally crosslinkable low-molecular-weight compound, The composition for a light-emitting diode, wherein the thermally crosslinkable low molecular weight compound is Compound 3 below: 【Chemistry 1】

2. 2. The composition for light-emitting diodes according to claim 1, wherein the high-molecular-weight compound contains a repeating unit having a triarylamine structural unit represented by the following general formula (2) and has a weight-average molecular weight of 10,000 or more and less than 1,000,000 in terms of polystyrene: 【Chemistry 2】 (In the formula, Ar1 and Ar2 each independently represent an arylene group or a heteroarylene group, R3 and R4 each independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms; X, Y, and Z each independently represent an aryl group, a heteroaryl group, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, or a cycloalkyloxy group having 5 to 10 carbon atoms, provided that at least one of them is an aryl group or a heteroaryl group.

3. 3. The composition for light-emitting diodes according to claim 2, wherein the high-molecular-weight compound is a copolymerized high-molecular-weight compound further comprising a repeating unit having one or more structural units selected from the group consisting of structural units represented by the following general formulas (3a) to (3x): 【Transformation 3】 (wherein R5 represents a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, a cycloalkyloxy group having 3 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, or an aryloxy group having 6 to 40 carbon atoms; R6 is an alkyl group having 1 to 40 carbon atoms or a cycloalkyl group having 3 to 40 carbon atoms; an alkyloxy group having 1 to 40 carbon atoms, a thioalkyloxy group having 1 to 40 carbon atoms, or a cycloalkyloxy group having 3 to 40 carbon atoms, Ar3, Ar5, and Ar7 each independently represent an arylene group or a heteroarylene group; Ar4, Ar6, and Ar8 each independently represent an aryl group or a heteroaryl group; a to d represent the number of R5; a represents an integer of 0 to 2; b represents an integer of 0 to 3; c represents an integer of 0 to 4; d represents an integer of 0 to 5.

4. 4. The composition for light-emitting diodes according to claim 2, wherein the high-molecular-weight compound is a copolymerized high-molecular-weight compound further comprising a repeating unit having one or more thermally crosslinkable structural units selected from the group consisting of thermally crosslinkable structural units represented by the following general formulas (4a) to (4z): 【Chemistry 4】 (In the formula, R5, R6, a, b, and c have the same meanings as in the general formulae (3a) to (3x).)

5. The composition for light-emitting diodes according to any one of claims 1 to 4, wherein the high-molecular-weight compound is a high-molecular-weight compound containing a repeating unit having a triarylamine structural unit represented by the following general formula (5) and a repeating unit having a linking structural unit represented by the following general formula (6), and has a weight-average molecular weight of 10,000 or more and less than 1,000,000 in terms of polystyrene: 【Transformation 5】 【Transformation 6】 (wherein R5, R6, b, and c have the same meanings as in the general formulae (3a) to (3x), Q represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3.

6. The composition for light-emitting diodes according to any one of claims 1 to 5, wherein the high molecular weight compound is a copolymer high molecular weight compound containing a repeating unit represented by the following general formula (7): 【Transformation 7】 (wherein R5, R6, b and c have the same meanings as in the general formulae (3a) to (3x) above.) and Q1 represents a hydrogen atom, a deuterium atom, an amino group, an aryl group, or a heteroaryl group; L3 represents a phenylene group; n represents an integer of 0 to 3; m represents a mole fraction of 0.1 to 0.9; p represents a mole fraction of 0.1 to 0.

9.

7. The composition for a light-emitting diode according to claim 1 , comprising two or more high-molecular-weight compounds.

8. A composition for an organic electroluminescence device, comprising the composition for a light-emitting diode according to any one of claims 1 to 7.

9. An organic electroluminescence element having a pair of electrodes and at least one organic layer sandwiched between the electrodes, An organic electroluminescence device, wherein the organic layer is formed by forming the composition for organic electroluminescence devices according to claim 8 into a film.

10. 10. The organic electroluminescence device according to claim 9, wherein the organic layer is a hole transport layer.

11. 10. The organic electroluminescent device according to claim 9, wherein the organic layer is an electron blocking layer.

12. The organic electroluminescence device according to claim 9 , wherein the organic layer is a hole injection layer.

13. The organic electroluminescence device according to claim 9 , wherein the organic layer is a light-emitting layer.

Images