TW202348779A - Composition and method for manufacturing a light emitting device using the same - Google Patents

Abstract

Provided is a composition useful for manufacturing a light emitting device with excellent luminous efficiency. Also provided is a method for manufacturing a light emitting device formed using the composition.

The composition is comprised of a polymer compound A containing a structural unit represented by Formula (1), a polymer compound B containing a structural unit represented by Formula (2), and a solvent.

Description

Composition and manufacturing method of light-emitting element using the same

The present invention relates to a composition and a method for manufacturing a light-emitting element using the composition.

Light-emitting elements such as organic electroluminescent elements can be suitable for display and lighting applications. As for the method of forming the organic layer of the light-emitting element, the wet method using a solvent is advantageous from the viewpoint of simplifying the manufacturing steps of large-area elements and reducing the manufacturing cost. For example, Patent Document 1 describes a composition containing a polymer phosphor, a nonionic surfactant, and a solvent as a composition used in the wet method. In addition, the polymer phosphor is a polymer compound that does not contain a structural unit represented by formula (1) described below.

[Prior technical literature]

[Patent Document]

[Patent Document 1] Japanese Patent Application Publication No. 2004-315679

However, the luminous efficiency of a light-emitting element formed using the above composition is not necessarily sufficient.

Therefore, an object of the present invention is to provide a composition that can be used to manufacture a light-emitting element with excellent luminous efficiency. Another object of the present invention is to provide a method for manufacturing a light-emitting element formed using the composition.

The present invention provides the following [1] to [15].

[1] A composition including a polymer compound A containing a structural unit represented by formula (1), a polymer compound B containing a structural unit represented by formula (2), and a solvent.

[In the formula,

Ar represents an aryl group or a divalent heterocyclic group, and these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. The plurality of Ar may be the same or different.

Ar' is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. There are multiple Ar's which may be the same or different.

Z is an aryl group belonging to a condensed ring or a divalent heterocyclic group belonging to a condensed ring, and these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded].

[In the formula,

B ¹ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxyalkyl group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom. These groups can Has substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. Multiple B ¹ 's may be the same or different.

s represents an integer above 0. There are multiple s which may be the same or different].

[2] The composition according to [1], wherein the content of the polymer compound A exceeds 1000 ppm by mass relative to the solvent, and the content of the polymer compound B exceeds 0 ppm by mass and is 1000 ppm relative to the solvent. Quality ppm or less.

[3] The composition according to [1] or [2], wherein the Ar is an aryl group which may have a substituent, and the Ar' is an aryl group which may have a substituent.

[4] The composition according to any one of [1] to [3], wherein the Ar is a phenylene group which may have a substituent, and the Ar' is a phenyl group which may have a substituent.

[5] The composition according to any one of [1] to [4], wherein Z is a 2-, 3-, 4-, 5- or 6-ring aryl group, Or a 2-ring, 3-ring, 4-ring, 5-ring or 6-ring divalent heterocyclic group, these groups may have substituents.

[6] The composition according to any one of [1] to [5], wherein Z is a tricyclic aryl group or a tricyclic divalent heterocyclic group, and these groups may have substituents.

[7] The composition according to any one of [1] to [6], wherein the aforementioned B ¹ is an alkyl group or an aryl group, and these groups may have a substituent.

[8] The composition according to any one of [1] to [7], wherein the polymer compound A further contains a structural unit selected from formula (Y) and a structure represented by formula (X) At least one type of structural unit in the group composed of units.

[In the formula, Ar ^Y1 represents an aryl group, a divalent heterocyclic group, or a divalent group in which at least one aryl group and at least one divalent heterocyclic group are directly bonded. These groups may have substituents. . When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded].

[In the formula,

a ^X1 and a ^X2 each independently represent an integer of 0 or more.

Ar ^X1 and Ar ^X3 each independently represent an aryl group or a divalent heterocyclic group, and these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded.

Ar ^X2 and ^Ar substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. When there are multiple Ar ^X2s , they may be the same or different. When there are multiple Ar ^X4s , they may be the same or different.

^{RX1 , R} When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. When there are multiple R ^X2 's, they may be the same or different. When there are multiple ^RX3s , they may be the same or different].

[9] The composition according to [8], wherein the polymer compound A contains a structural unit represented by formula (Y-1) or a structural unit represented by formula (Y-2) as the aforementioned formula (Y) The structural unit represented.

[In the formula,

R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. The plurality of R ^Y1's may be the same or different, or they may be bonded to each other and form a ring together with the carbon atoms to which they are bonded.

X ^Y1 represents the base represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -. R ^Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. The presence of multiple R ^Y2 may be the same or different, or they may be bonded to each other and form a ring together with the carbon atoms to which they are bonded].

[10] The composition according to any one of [1] to [9], wherein the solvent is an aromatic hydrocarbon solvent or an aromatic ether solvent.

[11] The composition according to any one of [1] to [10], wherein the solvent contains two or more solvents.

[12] The composition according to [11], wherein at least one of the two or more solvents is an aromatic hydrocarbon solvent or an aromatic ether solvent.

[13] The composition according to [11] or [12], wherein at least two of the two or more solvents are selected from the group consisting of aromatic hydrocarbon-based solvents and aromatic ether-based solvents. At least 2 types.

[14] The composition as described in any one of [1] to [13], which further contains a material selected from the group consisting of hole transport materials, hole injection materials, electron transport materials, electron injection materials, luminescent materials and antioxidants. At least one of the groups formed.

[15] A method of manufacturing a light-emitting element having an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, and

The manufacturing method includes the step of forming at least one layer of the aforementioned organic layer by a wet method using the composition described in any one of [1] to [14].

According to the present invention, it is possible to provide a composition that can be used to manufacture a light-emitting element with excellent luminous efficiency. In addition, according to the present invention, a method for manufacturing a light-emitting element formed using the composition can be provided.

Hereinafter, preferred embodiments of the present invention will be described in detail.

<Explanation of common terms>

Unless otherwise stated, terms commonly used in this specification have the following meanings.

Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tertiary butyl group.

The hydrogen atom can be a deuterium atom or a protium (protium; also known as light hydrogen) atom.

In the formula representing a metal complex, a solid line indicating a bond with the central metal means an ionic bond, a covalent bond, or a coordinate bond.

The so-called "low molecular compound" means a compound that has no molecular weight distribution and a molecular weight of 1×10 ⁴ or less.

The so-called "polymer compound" means a polymer with a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1×10 ³ to 1×10 ⁸ .

The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms.

When a polymer compound is used in a light-emitting element, the light-emitting element has excellent light-emitting characteristics. Therefore, the terminal group of the polymer compound is preferably a stable group. The terminal group of the polymer compound is preferably a group conjugated to the main chain of the polymer compound. Examples thereof include an aryl group or a monovalent heterocyclic group bonded to the main chain of the polymer compound via a carbon-carbon bond. base.

"Constructing unit" means one or more units present in a polymer compound. There are more than two structural units in polymer compounds, which are generally called "repeating units".

"Alkyl" may be either linear or branched. The number of carbon atoms of the linear alkyl group does not include the number of carbon atoms of the substituent, and is usually 1 to 50, preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10. The number of carbon atoms of the branched alkyl group does not include the number of carbon atoms of the substituent, and is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, and still more preferably 4 to 10.

The alkyl group may have a substituent. Examples of the alkyl group include: methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, isopentyl, 2-ethylbutyl, Hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecanyl, dodecyl groups and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents (such as trifluoromethyl, pentafluoroethyl, perfluorobutyl, perfluorohexyl, perfluorooctyl, 3-phenylpropyl base, 3-(4-methylphenyl)propyl, 3-(3,5-di-hexylphenyl)propyl and 6-ethyloxyhexyl).

The number of carbon atoms of the "cycloalkyl group" does not include the number of carbon atoms of the substituent, and is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, and still more preferably 4 to 10.

The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include cyclohexyl, methylcyclohexyl, ethylcyclohexyl, and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents.

"Aryl group" means the remaining atomic group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 40, more preferably 6 to 20, and still more preferably 6 to 10.

The aryl group may have a substituent. Examples of aryl groups include: phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2 -Fenyl, 3-Fenyl, 4-Fenyl, 2-phenylphenyl, 3-phenylphenyl, 4-phenylphenyl, and some or all of the hydrogen atoms in these groups are substituted Substituted groups.

"Alkoxy group" may be either linear or branched. The number of carbon atoms of the linear alkoxy group does not include the number of carbon atoms of the substituent, and is usually 1 to 50, preferably 1 to 20, and more preferably 1 to 10. The number of carbon atoms of the branched alkoxy group does not include the number of carbon atoms of the substituent, and is usually 3 to 50, preferably 4 to 20, and more preferably 4 to 10.

The alkoxy group may have a substituent. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, and heptyloxy , octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy and some or all of the hydrogen atoms in these groups are substituted Substituted groups.

The number of carbon atoms of the "cycloalkoxy group" does not include the number of carbon atoms of the substituent, and is usually 3 to 40, preferably 4 to 10.

The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group and a group in which part or all of the hydrogen atoms in the group are substituted by a substituent.

The number of carbon atoms of the "aryloxy group" does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 40, more preferably 6 to 20, and still more preferably 6 to 10.

The aryloxy group may have a substituent. Examples of the aryloxy group include: phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1-pyrenyloxy group, and some or all of these groups. A hydrogen atom substituted by a substituent.

The so-called "p-valent heterocyclic group" (p represents an integer above 1) means the remainder obtained by removing p hydrogen atoms directly bonded to the hydrogen atoms of the carbon atoms or heteroatoms constituting the ring from the heterocyclic compound. Atomic group. Among the p-valent heterocyclic groups, it is preferable that the remaining atomic group formed by removing p hydrogen atoms directly bonded to the hydrogen atoms of the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound, that is, the "p-valent heterocyclic group" Aromatic heterocyclic group".

二唑、噻二唑、噻唑、

唑、噻吩、吡咯、磷雜環戊二烯、呋喃、吡啶、吡

、嘧啶、三

、嗒

、喹啉、異喹啉、咔唑、二苯并磷雜環戊二烯等雜環本身顯示芳香族性的化合物；及啡

、啡噻

、二苯并硼雜環戊二烯、二苯并矽雜環戊二烯、苯并吡喃等雜環本身即使不顯示芳香族性而芳香環縮環於雜環之化合物。 "Aromatic heterocyclic compound" means

diazole, thiadiazole, thiazole,

Azole, thiophene, pyrrole, phospholane, furan, pyridine, pyridine

, pyrimidine, tri

,despair

, quinoline, isoquinoline, carbazole, dibenzophospholene and other compounds whose heterocycles themselves show aromatic properties; and phenanthrene

, phenanthrene

, dibenzoborole, dibenzosilole, benzopyran and other compounds in which the aromatic ring is condensed into the heterocycle even if the heterocycle itself does not show aromaticity.

The number of carbon atoms of the monovalent heterocyclic group does not include the number of carbon atoms of the substituent, and is usually 1 to 60, preferably 2 to 40, and more preferably 3 to 20. The number of heteroatoms of the monovalent heterocyclyl group does not include the number of heteroatoms of the substituent, and is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.

基、及此等基中之一部分或全部的氫原子經取代基取代的基。 The monovalent heterocyclic group may have a substituent. Examples of the monovalent heterocyclic group include: thienyl, pyrrolyl, furyl, pyridyl, piperidinyl, quinolyl, isoquinolyl, pyrimidinyl, trisyl

groups, and groups in which part or all of the hydrogen atoms in these groups are substituted by substituents.

The so-called "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The "amino group" may have a substituent, and is preferably a substituted amine group. The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent.

The substituted amino group may further have a substituent. Examples of substituted amino groups include dialkylamino groups, bicycloalkylamino groups, diarylamine groups, and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents.

Examples of the amino group and substituted amino group include: dimethylamino group, diethylamino group, diphenylamino group, bis(4-methylphenyl)amine group, and bis(4-tert-butylphenyl group) ) amino group, bis(3,5-di-tert-butylphenyl)amine group, and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents.

"Alkenyl" may be either linear or branched. The number of carbon atoms of the linear alkenyl group does not include the number of carbon atoms of the substituent, and is usually 2 to 50, preferably 2 to 20, and more preferably 2 to 10. The number of carbon atoms of the branched alkenyl group does not include the number of carbon atoms of the substituent, and is usually 3 to 50, preferably 4 to 20, and more preferably 4 to 10. The number of carbon atoms of "cycloalkenyl" does not include the number of carbon atoms of the substituent, and is usually 3 to 30, preferably 4 to 20, and more preferably 4 to 10.

The alkenyl group and the cycloalkenyl group may have a substituent. Examples of alkenyl and cycloalkenyl include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, and 1-hexenyl. Alkenyl, 5-hexenyl, 7-octenyl, and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents.

"Alkynyl" may be either linear or branched. The number of carbon atoms of the alkynyl group does not include the carbon atoms of the substituent, and is usually 2 to 50, preferably 3 to 20, and more preferably 3 to 10. The number of carbon atoms of the branched alkynyl group does not include the carbon atoms of the substituent, and is usually 4 to 30, preferably 4 to 20, and more preferably 4 to 10.

The number of carbon atoms of the "cycloalkynyl group" does not include the carbon atoms of the substituent, and is usually 4 to 50, preferably 5 to 20, and more preferably 6 to 10.

Alkynyl and cycloalkynyl groups may have substituents. Examples of alkynyl and cycloalkynyl include: ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1 -Hexynyl, 5-hexynyl, and groups in which some or all of the hydrogen atoms in these groups are substituted by substituents.

"Aryl group" means the remaining atomic group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from aromatic hydrocarbons. The number of carbon atoms of the aryl group does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20.

二基、及此等基中之一部分或全部的氫原子經取代基取代的基，較佳為式(A-1)~式(A-20)所表示的基。伸芳基包含由多個此等基鍵結而成的基。 The aryl group may have a substituent. Examples of the aryl group include: phenylene, naphthalenediyl, anthracenediyl, phenanthrenediyl, dihydrophenanthrenediyl, fused tetraphenyldiyl, fendiyl, pyrenediyl, perylenediyl,

Diradicals, and groups in which part or all of the hydrogen atoms in these groups are substituted by substituents, are preferably groups represented by formulas (A-1) to (A-20). Aryl groups include groups in which a plurality of these groups are bonded.

[In the formula, R and R ^a respectively independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom , these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. Multiple R's may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded. The presence of multiple R ^a may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded].

The number of carbon atoms of the divalent heterocyclic group does not include the number of carbon atoms of the substituent, and is usually 1 to 60, preferably 2 to 40, and more preferably 3 to 20. The number of heteroatoms of the divalent heterocyclic group does not include the number of heteroatoms of the substituent, and is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.

、氮雜萘、二氮雜萘、咔唑、二苯并呋喃、二苯并噻吩、二苯并矽雜環戊二烯、啡

、啡噻

、吖啶、二氫吖啶、二氫啡

、呋喃、噻吩、唑、二唑、三唑中去除直接鍵結於構成環之碳原子或雜原子之氫原子中之2個氫原子而成之二價基、及該基中之一部分或全部的氫原子經取代基取代之二價基，較佳為式(AA-1)~式(AA-34)所表示之基。二價雜環基包含多個此等基鍵結而成的基。 The divalent heterocyclic group may have a substituent. Examples of divalent heterocyclic groups include: pyridine, diazabenzene, tris

, azapine, naphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilyl, phenanthrene

, phenanthrene

, acridine, dihydroacridine, dihydrophine

, furan, thiophene, azole, oxadiazole, triazole, a divalent group formed by removing two hydrogen atoms directly bonded to the hydrogen atoms of the carbon atoms or heteroatoms constituting the ring, and part or all of the group The divalent radical in which the hydrogen atom is substituted by a substituent is preferably a radical represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a plurality of these groups bonded together.

[In the formula, R and R ^a represent the same meanings as above].

The so-called "crosslinking group" refers to a group that can generate a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. Cross-linking The group is preferably represented by any one of formula (XL-1) to formula (XL-19). The crosslinking group may have a substituent.

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer from 0 to 5. In the case where there are multiple ^RXLs , they can be the same or different. There are multiple n ^XLs that can be the same or different. *1 indicates the bonding position. These cross-linking groups may also have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded].

Examples of the "substituent" include: halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, Alkenyl, cycloalkenyl, alkynyl and cycloalkynyl. The substituent may also be a cross-linking group. Furthermore, when there are multiple substituents, these substituents can also be bonded to each other and form a ring together with the atoms to which they are bonded, but it is preferred not to form a ring.

<Composition of this embodiment>

The composition of this embodiment is a composition containing a polymer compound A containing a structural unit represented by formula (1), a polymer compound B containing a structural unit represented by formula (2), and a solvent.

In the composition of this embodiment, the polymer compound A, the polymer compound B, and the solvent are different components.

The composition of this embodiment may contain only one type of polymer compound A, polymer compound B, and solvent, or may contain two or more types.

The composition of this embodiment can be suitably used as a composition for a light-emitting element, for example. The light-emitting element formed using the composition of this embodiment (hereinafter also referred to as "the light-emitting element of this embodiment") has even more excellent luminous efficiency.

In the composition of this embodiment, the total content of the polymer compound A, the polymer compound B, and the solvent may be within a range that allows the composition to function as a composition (for example, a composition for a light-emitting element, the same applies below). In the composition of this embodiment, the total content of polymer compound A, polymer compound B and solvent can be, for example, 1 to 100 mass % based on the total amount of the composition. In terms of the luminous efficiency of the light-emitting element of this embodiment, More preferably, it is 10~100% by mass, more preferably 30~100% by mass, still more preferably 50~100% by mass, particularly preferably 70~100% by mass, even more preferably 90~100% by mass. .

In the composition of this embodiment, the content of the polymer compound A only needs to be within a range in which the function of the composition is exerted. In the composition of this embodiment, the content of the polymer compound A relative to the content of the solvent may be, for example, more than 0 ppm by mass, or more than 10 ppm by mass, or more than 100 ppm by mass, or more than 1,000 ppm by mass. ppm or more. In order that the luminous efficiency of the light-emitting element of this embodiment is more excellent, it is preferably more than 1000 mass ppm, more preferably more than 1000 mass ppm and 100 mass % or less, and still more preferably more than 1000 mass ppm and 50 mass %. % or less, particularly preferably more than 1000 mass ppm and less than 30 mass %, It is particularly preferably 3000 mass ppm or more and 10 mass % or less, further preferably 5000 mass ppm or more and 5 mass % or less, and still more preferably 7000 mass ppm or more and 2 mass % or less.

In the composition of this embodiment, the content of the polymer compound B only needs to be within the range in which the function of the composition is exerted. In the composition of this embodiment, the content of the polymer compound B relative to the content of the solvent may be, for example, more than 0 mass ppm and 100 mass % or less, or may be more than 0 mass ppm and 50 mass % or less, or it may be It is more than 0 mass ppm and 10 mass % or less, or it can be more than 0 mass ppm and 1 mass % or less. Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, it is preferably more than 0 mass ppm and 5000 mass ppm or less. , more preferably more than 0 mass ppm and less than 1000 mass ppm, and more preferably more than 0.01 mass ppm and less than 1000 mass ppm. Since the luminous efficiency of the light-emitting element of this embodiment will be even better, it is more preferably 0.1 mass ppm. More than 1000 ppm by mass and less than 1000 ppm by mass, more preferably 0.5 ppm by mass and less than 1000 ppm by mass, more preferably 1 ppm by mass and less than 1000 ppm by mass, particularly preferably 5 ppm by mass and less than 500 ppm by mass, especially preferably It is 10 mass ppm or more and 100 mass ppm or less.

In the composition of this embodiment, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the content of the polymer compound A is preferably greater than the content of the polymer compound B. In the composition of this embodiment, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the content of the solvent is preferably greater than the content of the polymer compound A. In the composition of this embodiment, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, it is preferable that the content of the polymer compound A is greater than that of the polymer compound B, and that the content of the solvent is greater than that of the polymer compound. The content of A is high.

[Polymer compound A]

Polymer compound A is a polymer compound containing a structural unit represented by formula (1). The polymer compound A is preferably a polymer compound containing no structural unit represented by formula (2).

(Structural unit represented by formula (1))

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, Ar is preferably an aryl group which may have a substituent.

Examples and preferred ranges of the aryl group and the divalent heterocyclic group in Ar are the same as the examples and preferred ranges of the aryl group and the divalent heterocyclic group represented by Ar ^Y1 described later.

Examples and preferred ranges of the substituents that the group represented by Ar may have are the same as the examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have, which will be described later.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, Ar' is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and more preferably Preferred are aryl groups, which may have substituents.

Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in Ar' are the same as the examples and preferred ranges of the aryl group and the monovalent heterocyclic group among the substituents that the group represented by Ar ^Y1 may have, which will be described later. .

Examples and preferred ranges of the substituents that the group represented by Ar′ may have are the same as examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have, which will be described later.

Since the light-emitting element of this embodiment has better luminous efficiency, it is preferable that Ar is an aryl group that may have a substituent and Ar′ is an aryl group that may have a substituent. More preferably, Ar is an aryl group that may have a substituent. phenyl and Ar' is a phenyl group which may have a substituent.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, Z is preferably an aryl group belonging to a condensed ring that may have a substituent. The aryl group belonging to the condensed ring only needs to have at least one ring constituting the condensed ring being an aromatic hydrocarbon ring.

The number of carbon atoms of the aryl group belonging to the condensed ring does not include the number of carbon atoms of the substituent, and is usually 7 to 60, preferably 8 to 40, more preferably 9 to 30, and still more preferably 10 to 20.

Examples of the aryl group belonging to the condensed ring include aromatic hydrocarbons belonging to the condensed ring (for example, bicyclic aromatic hydrocarbons such as naphthalene, indene, naphthoquinone, indenone, and tetralone; anthracene, phenanthrene, 3-ring aromatic hydrocarbons such as dihydrophenanthrene, fluorine, anthraquinone, phenanthrenequinone and quinone; 4-ring aromatic hydrocarbons such as benzanthracene, benzophenanthrene, benzofuranthene, pyrene and fluoranthene; 5-ring aromatic hydrocarbons such as benzanthracene, dibenzophenanthrene, dibenzofuranthene, indenofuranthene, perylene and benzofluoranthene; 6-ring aromatic hydrocarbons such as spirobisfuranthene; and benzospirobisfuranthene and A group formed by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring (hereinafter, n ^Z1 ring formula (n ^Z1 represents an integer above 2) from 7-ring aromatic hydrocarbons such as acenaphthofluoranthene) ) of aromatic hydrocarbons, a group formed by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring is called "n ^Z1 cyclic aryl group"), and this group may have a substituent. The aryl group belonging to the condensed ring includes a group in which a plurality of the above-mentioned groups are bonded.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the aryl group belonging to the condensed ring is preferably a 2-ring, 3-ring, 4-ring, 5-ring or 6-ring aryl group, and more preferably Preferably, it is a 2-ring, 3-ring, 4-ring or 5-ring aryl group, a 2-ring or 3-ring aryl group, particularly preferably a 3-ring aryl group, these groups may have substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the aryl group belonging to the condensed ring is preferably naphthalenediyl, anthracenediyl, phenanthrenediyl, dihydrophenanthrenediyl, fused tetraphenyldiyl, fluorine diyl, pyrenediyl, perylenediyl or benzophenanthrenediyl, more preferably naphthalenediyl, anthracenediyl, phenanthrenediyl, dihydrophenanthrenediyl or phenanthrenediyl, and more preferably the formula (A- 4)~The group represented by formula (A-9), formula (A-11), formula (A-12), formula (A-19) or formula (A-20), particularly preferably formula (A-7) ), a group represented by formula (A-9) or formula (A-19), these groups may have a substituent.

The number of carbon atoms of the divalent heterocyclic group belonging to the condensed ring, excluding the number of carbon atoms of the substituent, is usually 2 to 60, preferably 5 to 40, more preferably 8 to 30, and still more preferably 10 to 20. The number of heteroatoms of the divalent heterocyclic group belonging to the condensed ring, excluding the number of heteroatoms of the substituent, is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. In addition, the divalent heterocyclic group belonging to the condensed ring only needs to have at least one ring constituting the condensed ring to be a heterocyclic ring.

、啡噻

、9,10-二氫吖啶、5,10-二氫啡

、吖啶酮、9-氮雜-10-硼雜蒽、啡磷

、啡硒

、9-氮雜-10-矽雜蒽、氮雜蒽、二氮雜蒽、氮雜菲及二氮雜菲等3環式雜環式化合物；六氮雜聯伸三苯、苯并咔唑、氮雜苯并咔唑、二氮雜苯并咔唑、苯并萘并呋喃及苯并萘并噻吩等4環式雜環式化合物；二苯并咔唑、吲哚并咔唑、茚并咔唑、氮雜吲哚并咔唑、二氮雜吲哚并咔唑、氮雜茚并咔唑及二氮雜茚并咔唑等5環式雜環式化合物；咔唑并咔唑、苯并吲哚并咔唑及苯并茚并咔唑等6環式雜環式化合物；以及二苯并吲哚并咔唑及二苯并茚并咔唑等7環式雜環式化合物)中去除2個直接鍵結於構成環之原子之氫原子而成之基(以下，亦將自n^Z2環式(n^Z2表示2以上之整數)之雜環式化合物中去除2個直接鍵 結於構成環之原子之氫原子而成之基稱為「n^Z2環式之二價雜環基」)，該基可具有取代基。屬於縮合環的二價雜環基包含多個前述基鍵結而成的基。 Examples of the divalent heterocyclic group belonging to the condensed ring include: heterocyclic compounds belonging to the condensed ring (for example, azanaphthalene, diazodiazine, benzofuran, benzothiophene, indole, azaindole 2-ring heterocyclic compounds such as indoles, diazaindoles, benzodiazole, benzothiadiazole, benzotriazole, benzothiophene dioxide, benzothiophene oxide and benzopyrone ; Dibenzofuran, dibenzothiophene, dibenzothiophene dioxide, dibenzothiophene oxide, dibenzopyrone, dibenzoborole, dibenzosilole Diene, dibenzophosphocyclopentadiene, dibenzoselenophene, carbazole, azacarbazole, diazacarbazole, phenylephrine

, phenanthrene

, 9,10-dihydroacridine, 5,10-dihydrophoran

, acridone, 9-aza-10-boraxanthracene, phosphorus

, Selenium

, 3-ring heterocyclic compounds such as 9-aza-10-silicoanthracene, azaanthracene, diazaanthracene, azaphenanthrene and diazaphenanthrene; hexaazabiphenyl, benzocarbazole, 4-ring heterocyclic compounds such as azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran and benzonaphthothiophene; dibenzocarbazole, indolocarbazole, indenocarbazole 5-ring heterocyclic compounds such as azoles, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole and diazaindolocarbazole; carbazolocarbazole, benzo 2 A group that is directly bonded to a hydrogen atom of an atom constituting the ring (hereinafter, we will also exclude 2 directly bonded to a hydrogen atom constituting the ring from the heterocyclic compound of the n ^Z2 ring formula (n ^Z2 represents an integer of 2 or more). The radical formed by the hydrogen atom of the atom is called "n ^Z2 cyclic divalent heterocyclic radical"), and this radical may have a substituent. The divalent heterocyclic group belonging to the condensed ring includes a group in which a plurality of the above-mentioned groups are bonded.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the divalent heterocyclic group belonging to the condensed ring is preferably a 2-ring, 3-ring, 4-ring, 5-ring or 6-ring divalent heterocyclic group. The ring group is more preferably a bivalent heterocyclic group of 2-ring, 3-ring, 4-ring or 5-ring type, and the bivalent heterocyclic group of 2-ring or 3-ring type is particularly preferably 2 of 3-ring type. valent heterocyclic groups, these groups may have substituents.

、啡噻

、9,10-二氫吖啶、5,10-二氫啡

、氮雜蒽、二氮雜蒽、氮雜菲或二氮雜菲中去除2個直接鍵結於構成環之原子之氫原子而成之基，更佳為自氮雜萘、二氮雜萘、咔唑、二苯并呋喃、二苯并噻吩、二苯并矽雜環戊二烯、啡

、啡噻

或9,10-二氫吖啶中去除2個直接鍵結於構成環之原子之氫原子而成之基，又更佳為式(AA-7)~式(AA-22)所表示之基，特佳為式(AA-10)~式(AA-22)所表示的基，此等基可具有取代基。 Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the divalent heterocyclic group belonging to the condensed ring is preferably selected from the group consisting of azanaphthalene, naphthalene, carbazole, dibenzofuran, dibenzothiophene, Dibenzosilarene, phenylephrine

, phenanthrene

, 9,10-dihydroacridine, 5,10-dihydrophoran

, aza anthrene, diaza anthracene, aza phenanthrene or diaza phenanthrene, a group formed by removing two hydrogen atoms directly bonded to the atoms constituting the ring, more preferably from aza naphthalene, diaza phenanthrene , carbazole, dibenzofuran, dibenzothiophene, dibenzosilicon, phenanthrene

, phenanthrene

Or a group formed by removing two hydrogen atoms directly bonded to the atoms constituting the ring in 9,10-dihydroacridine, and more preferably a group represented by formula (AA-7) ~ formula (AA-22) , particularly preferred are groups represented by formula (AA-10) to formula (AA-22), and these groups may have substituents.

Examples and preferred ranges of the substituents that the group represented by Z may have are the same as examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have, which will be described later.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the structural unit represented by formula (1) is preferably a structural unit represented by formula (X-4) ~ formula (X-7), and more preferably is formula (X-4)~The structural unit represented by formula (X-6), and more preferably the structural unit represented by formula (X-4).

[In ^the formula, ^R Atoms, these groups may have substituents. When there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded. The ^plurality of R The presence of multiple ^R

Since the luminous efficiency of the light-emitting element of ^this embodiment will be more excellent, ^R Or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, etc. The group may further have a substituent.

Examples and preferable ^ranges of the aryl group, ^monovalent heterocyclic group and substituted amino group in ^R Examples and preferred ranges of substituted amino groups are the same.

^Examples and ^preferred ranges of the substituents that ^R

Examples of the structural unit represented by formula (1) include structural units represented by formula (X1-7) to formula (X1-19).

The content of the structural unit represented by formula (1) contained in the polymer compound A may be within a range in which the function of the polymer compound A is exerted. The content of the structural unit represented by formula (1) contained in the polymer compound A relative to the total content of the structural units contained in the polymer compound A is, for example, 0.01 to 100 mol%. Due to the luminescence of this embodiment The luminous efficiency of the element will be better, so it is preferably 0.05~90 mol%, more preferably 0.1~70 mol%, more preferably 0.2~50 mol%, particularly preferably 0.5~30 mol%. Especially preferably, it is 1~10 mol%. The polymer compound A may contain only one type of structural unit represented by formula (1), or may contain two or more types.

(Other structural units)

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the polymer compound A preferably further includes a group selected from the group consisting of a structural unit represented by formula (X) and a structural unit represented by formula (Y). At least one of the constituent units. That is, the polymer compound A preferably contains at least one structural unit selected from the group consisting of a structural unit represented by formula (X) and a structural unit represented by formula (Y), and formula (1) The polymer compound represented by the structural unit.

The polymer compound A contains at least one structural unit selected from the group consisting of a structural unit represented by formula (X) and a structural unit represented by formula (Y) and a structural unit represented by formula (1) In this case, it is preferable that the structural unit represented by formula (1) is different from the structural unit represented by formula (X) and the structural unit represented by formula (Y).

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the polymer compound A preferably further contains a structural unit represented by formula (Y).

Since the polymer compound A has excellent hole transport properties and the luminous efficiency of the light-emitting element of this embodiment will be even more excellent, the polymer compound A preferably further contains the formula (X) its constituent unit. Since the polymer compound A has excellent hole transport properties and the luminous efficiency of the light-emitting element of this embodiment will be even more excellent, the polymer compound A preferably further includes the structural unit represented by formula (X) and formula (Y) The structural unit represented.

When the polymer compound A contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) may be within the range in which the function of the polymer compound A is exerted. When the polymer compound A contains a structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) relative to the total content of the structural units contained in the polymer compound A is, for example, 1~ 99.99 mol%. Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, it is preferably 10 to 99.95 mol%, more preferably 30 to 99.9 mol%, and even more preferably 50 to 99.8 mol%. , the best value is 70~99.5 mol%, and the best value is 90~99 mol%.

The polymer compound A may contain only one type of structural unit represented by formula (Y), or may contain two or more types.

When the polymer compound A contains the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) may be within the range in which the function of the polymer compound A is exerted. When the polymer compound A contains the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) relative to the total content of the structural units contained in the polymer compound A is, for example, 0.01~ 99.9 mol%. Since the hole transport property of the polymer compound A is excellent and the luminous efficiency of the light-emitting element of this embodiment will be even better, it is preferably 0.05 to 90 mol%, and more preferably 0.1 to 70 mol%. %, more preferably 0.2~50 mol%, particularly preferably 0.5~30 mol%, particularly preferably 1~10 mol%.

The polymer compound A may contain only one type of structural unit represented by formula (X), or may contain two or more types.

When the polymer compound A contains a structural unit represented by formula (X) and/or a structural unit represented by formula (Y), and a structural unit represented by formula (1), the structural unit represented by formula (X), formula The total content of the structural unit represented by (Y) and the structural unit represented by formula (1) only needs to be within the range in which the function as the polymer compound A is exerted. When the polymer compound A contains a structural unit represented by formula (X) and/or a structural unit represented by formula (Y), and a structural unit represented by formula (1), the structure represented by formula (X) The total content of the unit, the structural unit represented by the formula (Y), and the structural unit represented by the formula (1) relative to the total content of the structural units contained in the polymer compound A is, for example, 1 to 100 mol%, because The luminous efficiency of the light-emitting element of this embodiment will be more excellent, so it is preferably 10~100 mol%, more preferably 30~100 mol%, further preferably 50~100 mol%, and particularly preferably 70~ 100 mol%, preferably 90~100 mol%.

‧The structural unit represented by formula (Y)

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the aryl group represented by Ar ^Y1 is preferably a phenylene group, a naphthalene diyl group, an anthracene diyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, or anthracene diyl group. group or pyrenediyl group, more preferably phenylene group, phenanthrenediyl group, dihydrophenanthrenediyl group or pyrenediyl group, and these groups may have substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the aryl group represented by Ar ^Y1 is preferably formula (A-1) ~ formula (A-14), formula (A-19) or formula (A The group represented by -20) is more preferably formula (A-1), formula (A-6), formula (A-7), formula (A-9) ~ formula (A-11), formula (A- 13) or a group represented by formula (A-19), and more preferably a group represented by formula (A-1), formula (A-7), formula (A-9) or formula (A-19).

、氮雜萘、二氮雜萘、咔唑、二苯并呋喃、二苯并噻吩、啡

、啡噻

、9,10-二氫吖啶或5,10- 二氫啡

中去除2個直接鍵結於構成環之原子之氫原子而成之基，更佳為自吡啶、二氮雜苯、三

、咔唑、二苯并呋喃、二苯并噻吩、啡

或啡噻

中去除2個直接鍵結於構成環的原子的氫原子而成的基，此等基可具有取代基。 Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the divalent heterocyclic group represented by Ar ^Y1 is preferably selected from pyridine, diazobenzene, tris

, azapine, naphthalene, carbazole, dibenzofuran, dibenzothiophene, phenylephrine

, phenanthrene

, 9,10-dihydroacridine or 5,10-dihydrophoran

A group formed by removing two hydrogen atoms directly bonded to the atoms constituting the ring, more preferably from pyridine, diazabenzene, triazine

, carbazole, dibenzofuran, dibenzothiophene, phenylephrine

Orphenidate

A group formed by removing two hydrogen atoms directly bonded to the atoms constituting the ring. These groups may have substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the divalent heterocyclic group represented by Ar ^Y1 is preferably formula (AA-1) ~ formula (AA-15), formula (AA-18) ~ formula The group represented by (AA-22), formula (AA-33) or formula (AA-34) is more preferably formula (AA-1) ~ formula (AA-6), formula (AA-10) ~ formula ( AA-15) or formula (AA-18) ~ formula (AA-22), more preferably formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15) , the group represented by formula (AA-18) or formula (AA-20) is particularly preferably represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) The basis of representation.

The preferred ranges of the aryl group and the divalent heterocyclic group in the divalent group formed by at least one aryl group ^{represented by Ar Y1 and at least one divalent heterocyclic group directly bonded to each other are the same as those represented by Ar Y1 respectively} . The preferred ranges of the aryl group and the divalent heterocyclic group are the same.

In Ar ^Y1 , "a divalent group in which at least one aryl group and at least one divalent heterocyclic group are directly bonded" include, for example, groups represented by the following formulas. These groups can be Has substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, Ar ^Y1 is preferably an aryl group which may have a substituent.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the substituent that the group represented by Ar ^Y1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or an aryloxy group. group, a monovalent heterocyclic group, a substituted amine group or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amine group, still more preferably It is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and is particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the aryl group among the substituents that the group represented by Ar ^Y1 may have is preferably removed from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorine. A group directly bonded to a hydrogen atom of an atom constituting the ring, more preferably a group obtained by removing one directly bonded to a hydrogen atom of an atom constituting the ring from benzene, phenanthrene, dihydrophenanthrene or fluorine, More preferably, it is a phenyl group, and these groups may further have a substituent.

、氮雜萘、二氮雜萘、咔唑、二苯并呋喃、二苯并噻吩、啡

、啡噻

、9,10-二氫吖啶或5,10-二氫啡

中去除1個直接鍵結於構成環之原子之氫原子而成之基，更佳為自吡啶、二氮雜苯、三

、咔唑、二苯并呋喃、二苯并噻吩、啡

或啡噻

中去除1個直接鍵結於構成環的原子的氫原子而成的基，又更佳為自吡啶、二氮雜苯或三

中去除1個直接鍵結於構成環的原子的氫原子而成的基，此等基亦可進一步具有取代基。 Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, among the substituents that the group represented by Ar ^Y1 may have, the monovalent heterocyclic group is preferably selected from pyridine, diazabenzene, triazine,

, azapine, naphthalene, carbazole, dibenzofuran, dibenzothiophene, phenylephrine

, phenanthrene

, 9,10-dihydroacridine or 5,10-dihydrophoran

A group formed by removing one directly bonded to a hydrogen atom of an atom constituting the ring, more preferably from pyridine, diazabenzene, triazine

, carbazole, dibenzofuran, dibenzothiophene, phenylephrine

Orphenidate

A group formed by removing one hydrogen atom directly bonded to an atom constituting the ring, more preferably from pyridine, diazabenzene or tris

A group formed by removing one hydrogen atom directly bonded to an atom constituting the ring, and these groups may further have a substituent.

Among the substituted amine groups among the substituents that the group represented by Ar ^Y1 may have, the substituent possessed by the amine group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further Has substituents. Examples and preferred ranges of aryl groups and monovalent heterocyclic groups among the substituents that the amine group can have are respectively the same as examples and preferred ranges of aryl groups and monovalent heterocyclic groups among the substituents that the group represented by Ar ^Y1 can have. The optimal range is the same.

The substituent that the group represented by Ar ^Y1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted substituent. Amino group or fluorine atom, more preferably alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group or substituted amino group, more preferably alkyl group, cycloalkyl group or aryl group, particularly preferably alkyl group or cyclic group Alkyl groups, these groups may further have substituents, and preferably have no further substituents.

Among the substituents that the group represented by Ar ^Y1 may further have, examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are respectively the same as the substituents that the group represented by Ar ^Y1 may have. The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group are the same.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the structural unit represented by the formula (Y) is preferably the structural unit represented by the formula (Y-1) or the formula (Y-2), and more preferably is the formula The structural unit represented by (Y-2).

R ^Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and still more preferably a hydrogen atom Or alkyl, these groups may have substituents.

In the formula (Y-1), since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, at least one of R ^Y1 (preferably at least two of R ^Y1 ) is an alkyl group or a cycloalkyl group. group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or fluorine atom, more preferably alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group or The substituted amino group is more preferably an alkyl group, a cycloalkyl group or an aryl group, particularly preferably an alkyl group, and these groups may also have substituents.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, R ^Y2 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amine group, and more preferably Preferably it is an alkyl group, cycloalkyl group, aryl group or monovalent heterocyclic group, and more preferably it is an alkyl group, cycloalkyl group or aryl group, and these groups may have substituents.

Examples and preferable ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^Y1 and R ^Y2 are respectively the same as those of the aryl group, monovalent heterocyclic group and substituted substituent that the group represented by Ar ^Y1 may have. Examples and preferred ranges of amine groups are the same.

Examples and preferred ranges of the substituents that R ^Y1 and R ^Y2 may have are the same as the examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have.

In X ^Y1 , the combination of two R ^Y2 in the group represented by -C(R ^Y2 ) ₂ - is preferably an alkyl group or a cycloalkyl group, an aryl group, or a monovalent hetero group. Cyclic group, or one is an alkyl or cycloalkyl and the other is an aryl or a monovalent heterocyclic group, more preferably one is an alkyl or cycloalkyl and the other is an aryl, these groups It may have a substituent. There are two R ^Y2 that can bond with each other and form a ring together with the atoms to which they are bonded. When R ^Y2 forms a ring, the group represented by -C(R ^Y2 ) ₂ - is preferably of the formula (Y- A1) to a group represented by formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have substituents.

^{in _ _ _} One is a cycloalkyl group and the other is an aryl group, and these groups may have substituents.

In X ^Y1 , the four R ^Y2 groups represented by -C( ^RY2 ) ₂ -C( ^RY2 ) _2- are preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent. There are multiple R ^Y2 that can bond with each other and form a ring together with the atoms to which they are bonded. When R ^Y2 forms a ring, the group represented by -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ - Preferably, they are groups represented by formula (Y-B1) to formula (Y-B5), and more preferably, they are groups represented by formula (Y-B3). These groups may have substituents.

[In the formula, R ^Y2 represents the same meaning as above].

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, X ^Y1 is preferably a base represented by -C(R ^Y2 ) ₂ - or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -, and more preferably Preferably, it is the basis represented by -C(R ^Y2 ) ₂ -.

Examples of the structural unit represented by formula (Y) include structural units represented by the following formula.

‧The structural unit represented by formula (X)

a ^X1 and ^a An integer from 0 to 2, preferably 0 or 1.

Since ^the luminous efficiency of ^the light-emitting element of this embodiment will be more excellent, ^R Heterocyclyl, and more preferably aryl, these groups may have substituents.

Examples and preferred ranges of aryl groups and monovalent heterocyclic groups in R ^X1 , ^{R X2 and} R The optimal range is the same.

Examples and preferred ^ranges of ^the aryl group and divalent heterocyclic group in Ar ^X1 , Ar ^X2 , Ar ^X3 and Ar .

Examples and preferable ranges of the aryl group and the divalent heterocyclic group in the divalent group in which at least one aryl group represented by Ar ^X2 and Ar ^X4 are directly bonded to at least one divalent heterocyclic group The examples and preferred ranges of the aryl group and the divalent heterocyclic group in Ar ^Y1 are the same.

The divalent group in which at least one aryl group among Ar ^X2 and Ar ^X4 is directly bonded to at least one divalent heterocyclic group may include at least one aryl group among Ar ^Y1 and at least One kind of divalent heterocyclic group is directly bonded to the same divalent group.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, Ar ^X1 , Ar ^X2 , Ar ^X3 and Ar ^X4 are preferably aryl groups which may have a substituent.

The examples and preferred ranges of the substituents that the groups represented by Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 can have are the same as the examples and preferred ranges of the substituents that the group represented by Ar ^Y1 can have.

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the structural unit represented by formula (X) is preferably the structural unit represented by formula (X-1) to formula (X-3).

[In the formula, R ^X4 represents the same meaning as above].

Examples of the structural unit represented by formula (X) include structural units represented by the following formula.

Examples of the polymer compound A include polymer compounds P-1 to P-4 shown in Table 1 below. Here, the "other" structural unit means a structural unit other than the structural unit represented by formula (1), the structural unit represented by formula (Y), and the structural unit represented by formula (X).

[Table 1]

[In Table 1, r', s', t' and u' represent the molar ratio (mol%) of each structural unit. r’+s’+t’+u’=100, and 70≦r’+s’+t’≦100].

The polymer compound A can be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, and is preferably made by copolymerizing a plurality of raw material monomers. copolymer.

The number average molecular weight of the polymer compound A in terms of polystyrene is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1×10 ⁴ to 5×10 ⁵ , and still more preferably 2×10 ⁴ to 2× 10 ⁵ . The weight average molecular weight of the polymer compound A in terms of polystyrene is preferably 1×10 ⁴ to 2×10 ⁶ , more preferably 2×10 ⁴ to 1×10 ⁶ , and still more preferably 5×10 ⁴ to 5× 10 ⁵ .

(Production method of polymer compound A)

The polymer compound A can be produced using a known polymerization method described in Chem.Rev., Vol. 109, pp. 897-1091 (2009), etc. Examples include Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction and Kumada reaction are methods of polymerization using coupling reactions of transition metal catalysts.

In the above-mentioned polymerization method, as for the method of feeding monomers, there can be listed: the method of feeding the total amount of monomers into the reaction system; after feeding a part of the monomers and allowing them to react, the remaining monomers are fed into the reaction system. The method of feeding the bodies together, continuously or divided; the method of feeding the single bodies continuously or divided, etc.

Examples of transition metal catalysts include palladium catalysts, nickel catalysts, etc.

The post-polymerization treatment can be performed alone or in combination with known methods, such as the method of removing water-soluble impurities by liquid separation; adding the reaction liquid after the polymerization to lower alcohols such as methanol, filtering the precipitated precipitate, and drying it. methods etc. When the purity of the polymer compound A is low, it can be purified by common methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, column chromatography, and the like.

[Polymer compound B]

Polymer compound B is a polymer compound containing a structural unit represented by formula (2). The polymer compound B is preferably a polymer compound containing no structural unit represented by formula (1).

(Structural unit represented by formula (2))

Since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, B ¹ is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxyalkyl group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent hetero group. Cyclic group or substituted amino group, more preferably alkyl, cycloalkyl, alkoxy, hydroxyalkyl, cycloalkoxy, aryl or aryloxy, still more preferably alkyl, cycloalkyl or aryl , an alkyl group or an aryl group is particularly preferred, and an alkyl group is particularly preferred. These groups may also have substituents.

The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in B ¹ are respectively the same as those of the aryl group, monovalent heterocyclic group and substituted amino group among the substituents that the group represented by Ar ^Y1 can have. The examples and preferred ranges are the same.

Examples of the hydroxyalkyl group in B ¹ include an alkyl group in which one hydrogen atom is substituted by a hydroxyl group.

Examples and preferred ranges of the substituents that B ¹ may have are the same as the examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have.

The repeating number (degree of polymerization) of the structural unit represented by the formula (2) contained in the polymer compound B is usually an integer from 5 to 10,000. In order to achieve better luminous efficiency of the light-emitting element of this embodiment, 10 is preferred. An integer of ~5000, preferably an integer of 20~2000, and more preferably an integer of 50~1000.

s is usually an integer from 0 to 10, preferably an integer from 0 to 5, more preferably an integer from 0 to 2, more preferably 0 or 1, and particularly preferably 0.

Examples of the structural unit represented by formula (2) include structural units represented by the following formula.

The content of the structural unit represented by the formula (2) contained in the polymer compound B may be within a range in which the function of the polymer compound B is exerted. The content of the structural unit represented by the formula (2) contained in the polymer compound B relative to the total content of the structural units contained in the polymer compound B is, for example, 1 to 100 mol%. Due to the luminescence of this embodiment The luminous efficiency of the element will be better, so it is preferably 10~100 mol%, more preferably 30~100 mol%, more preferably 50~100 mol%, and particularly preferably 70~100 mol%. Especially preferred is 90~100 mol%. The polymer compound B may contain only one type of structural unit represented by formula (2), or may contain two or more types.

Polymer compound B can be obtained from Dow Toray Co., Ltd., Shin-Etsu Chemical Industry Co., Ltd., BYK-Chemie Japan Co., Ltd., etc. In addition, it can be produced using a known polymerization method described in, for example, Japanese Patent Application Publication No. 2011-505448, Japanese Patent Application Publication No. 2012-68417, Japanese Patent Application Publication No. 2015-147930, and the like.

The polymer compound B may be any one of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in other forms, or may be copolymerized from a plurality of raw material monomers. copolymer.

The number average molecular weight of the polymer compound B in terms of polystyrene is preferably 1×10 ³ to 1×10 ⁶ , more preferably 2×10 ³ to 5×10 ⁵ , and still more preferably 2×10 ³ to 2× 10 ⁵ . The weight average molecular weight of polymer compound B in terms of polystyrene is preferably 2×10 ³ to 2×10 ⁶ , more preferably 5×10 ³ to 1×10 ⁶ , and still more preferably 5×10 ³ to 5× 10 ⁵ .

[Solvent]

The solvent contained in the composition of this embodiment (hereinafter also referred to as the "ink solvent") can dissolve or disperse the polymer compound A and the polymer compound B and does not interact with the polymer compound A and the polymer compound B. Those who respond to B are not particularly limited.

Since the composition of this embodiment can be easily produced, the ink solvent is preferably used alone. In addition, since the luminous efficiency of the light-emitting element of this embodiment is more excellent, it is preferable to mix two or more types of ink solvents and use them.

Examples of ink solvents include chlorine-based solvents, aromatic hydrocarbon-based solvents, aromatic ether-based solvents, aliphatic hydrocarbon-based solvents, aliphatic ether-based solvents, alcohol-based solvents, ketone-based solvents, amide-based solvents, and ester-based solvents. Solvents and carbonate-based solvents are preferably chlorine-based solvents, aromatic hydrocarbon-based solvents, aromatic ether-based solvents, aliphatic hydrocarbon-based solvents, and aliphatic ethers because the light-emitting element of this embodiment has better luminous efficiency. solvent, ketone solvent, amide solvent or ester solvent, more preferably aromatic hydrocarbon solvent, aromatic ether solvent, aliphatic hydrocarbon solvent, aliphatic ether solvent, ketone solvent or ester solvent , more preferably an aromatic hydrocarbon solvent, an aromatic ether solvent, an aliphatic hydrocarbon solvent or an aliphatic ether solvent, and particularly preferably an aromatic hydrocarbon solvent or an aromatic ether solvent.

When two or more types of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, at least one of the ink solvents is preferably a chlorine-based solvent, an aromatic hydrocarbon-based solvent, or an aromatic solvent. Ether solvent, aliphatic hydrocarbon solvent, aliphatic ether solvent, ketone solvent, amide solvent or ester solvent, more preferably aromatic hydrocarbon solvent, aromatic ether solvent, aliphatic hydrocarbon solvent , aliphatic ether solvents, ketone solvents or ester solvents, and better It is an aromatic hydrocarbon-based solvent, an aromatic ether-based solvent, an aliphatic hydrocarbon-based solvent or an aliphatic ether-based solvent, and an aromatic hydrocarbon-based solvent or an aromatic ether-based solvent is particularly preferred.

When two or more types of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, at least two of the ink solvents are preferably selected from chlorine-based solvents and aromatic hydrocarbon-based solvents. , at least 2 of the group consisting of aromatic ether solvents, aliphatic hydrocarbon solvents, aliphatic ether solvents, ketone solvents, amide solvents and ester solvents, preferably selected from aromatic hydrocarbons At least two types from the group consisting of solvents, aromatic ether solvents, aliphatic hydrocarbon solvents, aliphatic ether solvents, ketone solvents and ester solvents, and more preferably selected from aromatic hydrocarbon solvents , at least 2 of the group consisting of aromatic ether solvents, aliphatic hydrocarbon solvents and aliphatic ether solvents, particularly preferably selected from the group consisting of aromatic hydrocarbon solvents and aromatic ether solvents At least 2 of them.

When more than two kinds of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the combination of at least two kinds of ink solvents is preferably an aromatic hydrocarbon solvent and an aromatic ether. It is a combination of one of the solvents and one of the aromatic hydrocarbon solvents, aromatic ether solvents, aliphatic hydrocarbon solvents, aliphatic ether solvents, ketone solvents, amide solvents and ester solvents. More preferably, one of aromatic hydrocarbon solvents and aromatic ether solvents and aromatic hydrocarbon solvents, aromatic ether solvents, aliphatic hydrocarbon solvents, aliphatic ether solvents, ketone solvents and ester solvents The combination of one of them is more preferably a combination of two aromatic hydrocarbon solvents, a combination of two aromatic ether solvents, or a combination of an aromatic hydrocarbon solvent and an aromatic ether solvent.

Examples of chlorine-based solvents include dichloroethane, trichloroethane, chlorobenzene, and dichlorobenzene.

Examples of aromatic hydrocarbon solvents include toluene, xylene, ethylbenzene, trimethylbenzene, tetramethylbenzene, propylbenzene, butylbenzene, pentylbenzene, cyclopentylbenzene, and methylcyclopentyl Benzene, hexylbenzene, ring Hexylbenzene, methylcyclohexylbenzene, heptylbenzene, cycloheptylbenzene, methylcycloheptylbenzene, octylbenzene, nonylbenzene, decylbenzene, undecylbenzene, dodecylbenzene, Trialkylbenzene, tetradecylbenzene and tetralin.

Examples of aromatic ether solvents include anisole, dimethoxybenzene, trimethoxybenzene, ethoxybenzene, propoxybenzene, butoxybenzene, methylpropoxybenzene, and butoxybenzene. , methoxytoluene, ethoxytoluene, methoxynaphthalene, ethoxynaphthalene and phenoxytoluene.

Examples of aliphatic hydrocarbon solvents include cyclohexane, methylcyclohexane, pentane, hexane, heptane, octane, nonane, decane, dodecane, and dicyclohexane.

烷、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚及三乙二醇二甲醚。 Examples of aliphatic ether solvents include: diisopropyl ether, methyl butyl ether, dibutyl ether, tetrahydrofuran, dibutyl ether, and diisopropyl ether.

alkane, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether and triethylene glycol dimethyl ether.

Examples of alcohol-based solvents include ethanol, propanol, butanol, pentanol, cyclopentanol, hexanol, cyclohexanol, heptanol, octanol, benzyl alcohol, phenylethanol, ethylene glycol, propylene glycol, and diethyl alcohol. Glycol monomethyl ether, propane glycol and glycerin.

Examples of ketone solvents include acetone, methyl ethyl ketone, methyl butyl ketone, dibutyl ketone, cyclohexanone, methylcyclohexanone, hexanone, octanone, nonanone, phenyl acetone, and ethanol. Acetone, acetone, acetophenone, methyl naphthyl ketone and isophorone.

Examples of the amide solvent include N-methylpyrrolidone, N-ethylpyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide and 1,3- Dimethyl-2-imidazolidinone.

Examples of ester solvents include butyl acetate, ethyl acetate, propyl acetate, amyl acetate, ethyl propionate, ethyl butyrate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, Diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl-3-ethoxypropionate, acetic acid 3-Methoxybutyl ester, 3-methyl-3-methoxybutyl acetate, propyl formate, propyl lactate, ethyl phenylacetate, ethyl benzoate, β-propiolactone, γ- Butyrolactone, and delta-valerolactone.

Examples of carbonate solvents include dimethyl carbonate, diethyl carbonate, ethyl carbonate, and propyl carbonate.

In the composition of this embodiment, the boiling point of at least one of the ink solvents at 1 atmosphere is usually 40°C to 500°C. Since the luminous efficiency of the light-emitting element of this embodiment will be better, it is preferably 60℃~450℃, more preferably 80℃~400℃, more preferably 100℃~300℃.

When two or more types of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the boiling point of at least one of the ink solvents at 1 atmosphere is preferably 100°C to 450°C. ℃, preferably 150℃~400℃, and more preferably 200℃~300℃.

When two or more types of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, it is preferable that at least one of the ink solvents has a boiling point of 60°C or higher under 1 atmosphere. and less than 200°C, and at least one kind has a boiling point of 200°C or more and 450°C or less at 1 atmosphere, more preferably at least one kind has a boiling point of 80°C or more and 195°C or less at 1 atmosphere, and at least One species has a boiling point of 210°C to 400°C under 1 atmosphere, and more preferably at least one species has a boiling point of 100°C to 190°C under 1 atmosphere, and at least one species has a boiling point of 100°C to 190°C under 1 atmosphere. The boiling point is above 220℃ and below 300℃.

When two or more types of ink solvents are used, and when the total content of the ink solvents is 100 parts by mass, the luminous efficiency of the light-emitting element of this embodiment will be more excellent. Therefore, the content of the printing ink solvent with the smallest content in the printing ink solvent is preferably 1 to 50 parts by mass, more preferably 5 to 45 parts by mass, and even more preferably 10 to 40 parts by mass.

When more than two kinds of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the boiling point of the ink solvent with the smallest content among the ink solvents is preferably 60°C under 1 atmosphere. It is more than 200 degreeC and less than 200 degreeC, More preferably, it is 80 degreeC or more and 195 degreeC or less, More preferably, it is 100 degreeC or more and 190 degreeC or less.

When two or more types of ink solvents are used, and the total content of the ink solvents is set to 100 parts by mass, the luminous efficiency of the light-emitting element of this embodiment will be more excellent, so the content of the ink solvents The content of the largest amount of printing ink solvent is preferably 50 to 99 parts by mass, more preferably 55 to 95 parts by mass, and still more preferably 60 to 90 parts by mass.

When two or more types of ink solvents are used, since the luminous efficiency of the light-emitting element of this embodiment will be more excellent, the boiling point of the ink solvent with the largest content among the ink solvents is preferably 200°C at 1 atmosphere. The temperature is not less than 450°C and not more than 450°C, more preferably not less than 210°C and not more than 400°C, still more preferably not less than 220°C and not more than 300°C.

When more than two kinds of ink solvents are used, the types of ink solvents are usually 2 to 20 kinds, because the production of the composition of this embodiment will become easier, and the luminous efficiency of the light-emitting element of this embodiment will be easier. will be more excellent, so 2 to 10 types are preferred, 2 to 5 types are more preferred, 2 or 3 types are more preferred, and 2 types are particularly preferred.

When using two or more ink solvents, it is sufficient as long as the mixed solvent is liquid at 25°C and 1 atmosphere.

[Other ingredients]

The composition of this embodiment may also contain polymer compound A, polymer compound B, and a group selected from the group consisting of hole transport materials, hole injection materials, electron transport materials, electron injection materials, luminescent materials, and antioxidants. At least one component of the group. However, the hole transport material, hole injection material, electron transport material, electron injection material and luminescent material are different from the polymer compound A and the polymer compound B.

(hole transport material)

Hole transport materials are classified into low molecular compounds and polymer compounds. The hole transport material may also have cross-linking groups.

Examples of low molecular compounds include triphenylamine and its derivatives, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (α-NPD), and N,N'- Aromatic amine compounds such as diphenyl-N,N'-di(m-tolyl)benzidine (TPD).

Examples of the polymer compound include polyvinylcarbazole and its derivatives; polyarylene having an aromatic amine structure in the side chain or main chain and its derivatives. The polymer compound may also be a compound bonded with an electron-accepting site such as fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitroquinone.

In the composition of this embodiment, when a hole transport material is included, when the total content of the polymer compound A and the polymer compound B is 100 parts by mass, the content of the hole transport material is usually 1~ 10,000 parts by mass.

One type of hole transport material may be used alone, or two or more types may be used in combination.

(electron transmission material)

Electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may also have cross-linking groups.

二唑、蒽醌二甲烷、苯醌、萘醌、蒽醌、四氰基蒽醌二甲烷、茀酮、二苯基二氰基乙烯及聯苯醌、以及此等的衍生物。 Examples of low molecular compounds include metal complexes using 8-hydroxyquinoline as a ligand,

Oxidazole, anthraquinone dimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinone dimethane, quinone, diphenyldicyanoethylene and diphenoquinone, and their derivatives.

Examples of the polymer compound include polyphenylene, polyfluoride, and derivatives thereof. The polymer compound may also be doped with metal.

In the composition of this embodiment, when an electron transport material is included, when the total content of the polymer compound A and the polymer compound B is 100 parts by mass, the content of the electron transport material is usually 1 to 10,000 parts by mass.

One type of electron transmission material may be used alone, or two or more types may be used in combination.

(hole injection materials and electron injection materials)

Hole injection materials and electron injection materials are each classified into low molecular compounds and high molecular compounds. The hole injection material and the electron injection material may also have cross-linking groups.

Examples of low molecular compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride and potassium fluoride.

啉、以及該等之衍生物；於主鏈或側鏈含有芳香族胺結構之聚合物等導電性高分子。 Examples of polymer compounds include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoline.

Phinolines, and their derivatives; conductive polymers such as polymers containing aromatic amine structures in the main chain or side chain.

When the composition of this embodiment contains a hole injection material and/or an electron injection material, when the total content of the polymer compound A and the polymer compound B is 100 parts by mass, the hole injection material The content of each of the electron injection material and the electron injection material is usually 1 to 10,000 parts by mass.

Each of the hole injection material and the electron injection material may be used individually by one type, or two or more types may be used in combination.

‧Ion doping

The hole injection material or the electron injection material can also be doped with ions. For example, when the hole injection material or the electron injection material contains a conductive polymer, the conductivity of the conductive polymer is preferably 1×10 ^-5 S/cm~1×10 ³ S/cm. In order to set the conductivity of the conductive polymer within this range, the conductive polymer can be doped with an appropriate amount of ions.

Regarding the type of ions doped into the hole injection material or the electron injection material, for example, in the case of a hole injection material, anions may be used, and in the case of an electron injection material, cations may be used. Examples of anions include polystyrene sulfonate ions, alkyl benzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions.

One type of doping ions may be used alone, or two or more types may be used in combination.

(Light-emitting material)

Luminescent materials are classified into low molecular compounds and high molecular compounds. The luminescent material may also have cross-linking groups.

Examples of low molecular compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and phosphorescent compounds containing iridium, platinum or europium as the central metal.

Examples of the polymer compound include polymer compounds containing a structural unit represented by formula (Y) and/or a structural unit represented by formula (X).

Examples of phosphorescent compounds include metal complexes shown below.

When the composition of this embodiment contains a luminescent material, the content of the luminescent material is usually 1 to 10,000 parts by mass when the total content of the polymer compound A and the polymer compound B is 100 parts by mass.

One type of luminescent material may be used alone, or two or more types may be used in combination.

(Antioxidant)

The antioxidant only needs to be a compound that is soluble in the same solvent as polymer compound A and polymer compound B and does not hinder light emission and charge transport. Examples thereof include phenolic antioxidants and phosphorus antioxidants.

When the composition of this embodiment contains an antioxidant, the content of the antioxidant is usually 0.001 to 10 parts by mass when the polymer compound A and the polymer compound B are 100 parts by mass.

One type of antioxidant may be used alone, or two or more types may be used in combination.

<Membrane>

The film can be formed using the composition of this embodiment by, for example, spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, or dip coating. , spray coating method, screen printing method, flexographic printing method, lithographic printing method, inkjet printing method, capillary coating method, nozzle coating method and other wet methods.

When the composition of this embodiment is used to produce a film by a wet method, the ink solvent is removed if necessary. Examples of methods for removing the ink solvent include natural drying, vacuum drying and heated drying, with natural drying or vacuum drying being preferred. The drying temperature is usually 0°C~300°C, preferably 5°C~150°C, more preferably 10°C~75°C, and more preferably 15°C~40°C.

The viscosity of the composition of this embodiment only needs to be adjusted according to the type of wet method. When applied to a printing method in which a solution passes through a discharge device such as an inkjet printing method, clogging and flying bending during discharge are unlikely to occur. Therefore, it is preferably 1~50mPa-s at 25°C, and more preferably 1~20mPa-s.

The film is suitable as a light-emitting layer, a hole transport layer or a hole injection layer in a light-emitting element.

The thickness of the film is usually 1nm~1μm.

<Manufacturing method of light-emitting element>

The method of manufacturing a light-emitting element according to this embodiment is a method of manufacturing a light-emitting element having an anode, a cathode, and one or a plurality of organic layers provided between the anode and the cathode, and the The manufacturing method includes the step of forming at least one layer of the organic layer by a wet method using the composition of this embodiment.

The light-emitting element of this embodiment is a light-emitting element having at least one organic layer formed by a wet method using the composition of this embodiment.

The structure of the light-emitting element of this embodiment includes, for example, electrodes including an anode and a cathode, and at least one organic layer formed between the electrodes and formed by a wet method using the composition of this embodiment.

In the light-emitting element of this embodiment, examples of the wet method include the wet method described in the above <Film> section.

In the step of forming the organic layer by a wet method using the composition of this embodiment, the ink solvent is removed if necessary. As for the method of removing the ink solvent, the method of removing the ink solvent described in the above <Film> section can be cited.

[Layer composition]

The organic layer included in a light-emitting element is usually one or more of a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. The at least one organic layer formed by a wet method using the composition of this embodiment is usually one or more of a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. Preferably it is a luminescent layer, a hole transport layer or a hole injection layer, and more preferably it is a luminescent layer. The layers respectively include luminescent materials, hole transport materials, hole injection materials, electron transport materials, and electron injection materials. These layers can be prepared and used by dissolving the luminescent material, hole transport material, hole injection material, electron transport material, and electron injection material in the above-mentioned ink solvent, and use the same method as the above-mentioned film production. to form.

The light-emitting element has a light-emitting layer between the anode and the cathode. From the viewpoint of hole injection properties and hole transport properties, the light-emitting element of this embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light-emitting layer. From the viewpoint of electron transportability, it is preferable to have at least one layer of an electron injection layer and an electron transport layer between the cathode and the light-emitting layer.

For the hole transport layer, electron transport layer, luminescent layer, hole injection layer, and electron injection layer, in addition to the compositions of this embodiment, the above-mentioned hole transport materials, electron transport materials, luminescent materials, and It is formed by hole injection materials and electron injection materials.

The material of the hole transport layer, the material of the electron transport layer and the material of the luminescent layer will be dissolved in the solvent used in the formation of the layers adjacent to the hole transport layer, electron transport layer and luminescent layer during the production of the light-emitting element. In this case, in order to prevent the material from being dissolved in the solvent, it is preferred that the material has a cross-linking group. After each layer is formed using a material having a cross-linking group, the layer can be insolubilized by cross-linking the cross-linking group.

In the manufacturing method of the light-emitting element of this embodiment, in terms of the formation method of each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, when a low molecular compound is used, Examples include dry methods such as vacuum evaporation methods and wet methods. When using a polymer compound, examples include wet methods.

In the light-emitting element of this embodiment, the anode, the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode can each be provided with two or more layers as needed. When there are multiple layers of anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer and cathode, they may be the same or different.

In the light-emitting element of this embodiment, the thicknesses of the anode, the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode are usually 1 nm to 1 μm, preferably 2 nm to 500 nm, and More preferably, it is 5nm~150nm.

In the light-emitting element of this embodiment, the order, number, and thickness of the stacked layers can be adjusted by taking into account the brightness lifetime, driving voltage, and luminous efficiency of the light-emitting element.

[Substrate/Electrode]

The substrate in the light-emitting element only needs to be a substrate that can form an electrode and does not undergo chemical changes when forming an organic layer. For example, it can be a substrate made of glass, plastic, silicon, or other materials. In the case of an opaque substrate, the electrode furthest from the substrate is preferably transparent or translucent.

Examples of materials for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, and tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; silver, palladium, and copper. Compound (APC); NESA, gold, platinum, silver, copper.

Examples of materials for the cathode include: lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium and other metals; alloys of two or more of these; one of these Alloys with one or more kinds of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; as well as graphite and graphite interlayer compounds. Examples of alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.

The anode and the cathode may each have a laminated structure of two or more layers.

The light-emitting element of this embodiment can be manufactured, for example, by sequentially stacking layers on a substrate. Specifically, an anode can be provided on a substrate, a hole injection layer, a hole transport layer, and other layers are provided thereon, a light-emitting layer is provided thereon, and an electron transport layer, an electron injection layer, and other layers are provided thereon, and further A cathode is laminated thereon to produce a light-emitting element. As far as other manufacturing methods are concerned, A light-emitting element can be manufactured by arranging a cathode on a substrate, arranging an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer and other layers thereon, and further laminating an anode thereon. Furthermore, according to another manufacturing method, the anode or the anode-side base material on which each layer is laminated is faced and joined to the cathode or the cathode-side base material on which the respective layers are laminated.

[use]

The light-emitting element of this embodiment can be suitably used as a light source for backlight of a liquid crystal display device, a light source for illumination, organic EL lighting, display devices such as computers, televisions, and mobile terminals (such as organic EL displays and organic EL TVs).

[Example]

Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to these examples.

In the examples, the number average molecular weight (Mn) of the polymer compound in terms of polystyrene and the weight average molecular weight (Mw) in terms of polystyrene were measured using tetrahydrofuran in the moving layer through the following particle size screening chromatography (SEC) and find it. In addition, the measurement conditions of SEC are as follows.

The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL was injected into the SEC. The mobile phase flows at a flow rate of 2.0 mL/min. PLgel MIXED-B (manufactured by Polymer Laboratories) was used as the column. As a detector, a UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used.

<Synthesis Example 1> Synthesis of Compounds M1 to M15

Compound M1, compound M2 and compound M7 were synthesized according to the method described in International Publication No. 2002/045184.

Compound M3 was synthesized according to the method described in International Publication No. 2005/052027.

Compound M4 was synthesized according to the method described in International Publication No. 2012/086671.

Compound M5 and compound M12 were synthesized according to the method described in Japanese Patent Application Laid-Open No. 2012-144722.

Compound M6 was synthesized according to the method described in International Publication No. 2005/049546.

Compound M8 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2004-143419.

Compound M9 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2011-174062.

Compound M10 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2008-106241.

Compound M11 was synthesized according to the method described in International Publication No. 2012/133256.

Compound M13 was synthesized according to the method described in International Publication No. 2014/157016.

Compound M14 was synthesized according to the method described in International Publication No. 2008/143272.

Compound M15 was synthesized according to the method described in International Publication No. 2004/060970.

<Synthesis Example 2> Synthesis of Polymer Compound 1

Polymer compound 1 was synthesized according to the method described in International Publication No. 2011/049241 using compound M1, compound M2 and compound M3. The Mn of the polymer compound 1 is 8.9×10 ⁴ and the Mw is 4.2×10 ⁵ .

Polymer Compound 1, in terms of theoretical values determined from the amounts of raw materials fed, is a structural unit derived from Compound M1, a structural unit derived from Compound M2, and a structural unit derived from Compound M3 based on 50 : A copolymer composed of a molar ratio of 42.5:7.5.

<Synthesis Example 3> Synthesis of Polymer Compound 2

Polymer compound 2 was synthesized according to the method described in International Publication No. 2011/081065 using compound M4, compound M1, compound M5, and compound M6. The Mn of the polymer compound 2 is 1.6×10 ⁵ and the Mw is 4.9×10 ⁵ .

In terms of theoretical values determined from the amounts of raw materials fed, polymer compound 2 is a structural unit derived from compound M4, a structural unit derived from compound M1, a structural unit derived from compound M5, and a structural unit derived from compound M5. A copolymer composed of structural units derived from compound M6 with a molar ratio of 36:14:44:6.

<Synthesis Example 4> Synthesis of Polymer Compound 3

Polymer compound 3 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2012-216815 using compound M4, compound M7 and compound M8. The Mn of polymer compound 3 is 1.0×10 ⁵ and the Mw is 2.6×10 ⁵ .

Polymer compound 3, in terms of theoretical values determined from the amount of raw materials fed, is a structural unit derived from compound M4, a structural unit derived from compound M7, and a structural unit derived from compound M8, with 50 : A copolymer composed of a molar ratio of 45:5.

<Synthesis Example 5> Synthesis of Polymer Compound 4

Polymer compound 4 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2012-36381 using compound M1 and compound M2. The Mn of polymer compound 4 is 8.1×10 ⁴ and the Mw is 3.4×10 ⁵ .

Polymer compound 4, in terms of a theoretical value determined from the amount of raw materials fed, is composed of a structural unit derived from compound M1 and a structural unit derived from compound M2 in a molar ratio of 50:50. copolymer.

<Synthesis Example 6> Synthesis of Polymer Compound 5

Polymer compound 5 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2012-144722 using compound M9, compound M6, compound M7 and compound M10. The Mn of the polymer compound 5 is 7.8×10 ⁴ and the Mw is 2.6×10 ⁵ .

Polymer compound 5, in terms of theoretical values determined from the amount of raw materials fed, is a structural unit derived from compound M9, a structural unit derived from compound M6, a structural unit derived from compound M7, and a structural unit derived from compound M7. A copolymer composed of structural units derived from compound M10 with a molar ratio of 50:30:12.5:7.5.

<Synthesis Example 7> Synthesis of Polymer Compound 6

Polymer compound 6 was synthesized according to the method described in International Publication No. 2012/133256 using compound M11, compound M12 and compound M13. The Mn of polymer compound 6 is 8.1×10 ⁴ and the Mw is 2.4×10 ⁵ .

Polymer compound 6, in terms of theoretical values determined from the amounts of raw materials fed, has a structural unit derived from compound M11, a structural unit derived from compound M12, and a structural unit derived from compound M13. : A copolymer composed of a molar ratio of 45:5.

<Synthesis Example 8> Synthesis of Polymer Compound 7

Polymer compound 7 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2015-35600 using compound M4, compound M1, compound M5, compound M8, compound M14, and compound M15. The Mn of polymer compound 7 is 9.1×10 ⁴ and the Mw is 2.3×10 ⁵ .

Polymer compound 7, in terms of theoretical values determined by the amount of feed raw materials, is a structural unit derived from compound M4, a structural unit derived from compound M1, a structural unit derived from compound M5, and a structural unit derived from compound M5. The structural unit derived from M8, derived from compound M14 A copolymer composed of structural units derived from compound M15 in a molar ratio of 36:14:41:5:3:1.

<Comparative Example CD1> Production and evaluation of light-emitting element CD1

(Formation of anode and hole injection layer)

An ITO film is attached to a glass substrate with a thickness of 45 nm by sputtering to form an anode. On the anode, hole injection material ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) was formed into a film with a thickness of 35 nm by a spin coating method. The substrate with the hole injection layer laminated on it was heated on a hot plate at 50°C for 3 minutes in an atmospheric environment, and further heated at 230°C for 15 minutes, thereby forming the hole injection layer.

(Formation of hole transport layer)

In a solvent (hereinafter, also referred to as "organic solvent 1") in which cyclohexylbenzene and xylene are mixed at a mass ratio of 61.8:38.2, 0.6 mass% relative to the amount of organic solvent 1 The concentration causes polymer compound 1 to dissolve. The obtained solution was used to form a film with a thickness of 20 nm on the hole injection layer by spin coating, and was heated on a hot plate at 200° C. for 30 minutes in a nitrogen atmosphere to form a hole transport layer.

(Formation of luminescent layer)

The polymer compound 2 was dissolved in the organic solvent 1 at a concentration of 0.9% by mass relative to the amount of the organic solvent 1. The obtained solution was used to form a film with a thickness of 60 nm on the hole transport layer by spin coating, and was heated on a hot plate at 180° C. for 10 minutes in a nitrogen atmosphere to form a light-emitting layer.

(Formation of electron injection layer and cathode)

Place the substrate with the light-emitting layer formed on it in an evaporator, and after reducing the pressure to 1×10 ^-4 Pa or less, evaporate 4 nm of sodium fluoride as an electron injection material on the light-emitting layer to form an electron injection layer. Then, Approximately 80 nm of aluminum is evaporated on the electron injection layer to form a cathode. After the evaporation, the light-emitting element CD1 is manufactured by sealing using a glass substrate.

(Evaluation of light-emitting components)

By applying a voltage to the light-emitting element CD1, EL emission is observed. The luminous efficiency of the light-emitting element CD1 at 1000cd/ ^m2 is 3.9cd/A.

<Example D1> Production and evaluation of light-emitting element D1

In Comparative Example CD1 (Formation of Luminous Layer), in addition to using "polysilicone oil KF-96 1000cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd., having formula (2)" (in the formula, B ¹ is a methyl group, s is 0 "Polymer compound B) with a structural unit represented by ) and a degree of polymerization of 300 to 400 is mixed with organic solvent 1 at a concentration of 10 mass ppm relative to the amount of organic solvent 1" instead of "organic solvent 1" Except for this, the light-emitting element D1 was produced in the same manner as in Comparative Example CD1.

By applying a voltage to the light-emitting element D1, EL emission is observed. The luminous efficiency of the light-emitting element D1 at 1000cd/ ^m2 is 4.5cd/A.

<Example D2> Production and evaluation of light-emitting element D2

In Comparative Example CD1 (formation of the light-emitting layer), in addition to using "KF-96 1000cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed in the organic solvent 1 at a concentration of 100 ppm by mass relative to the amount of the organic solvent 1 A light-emitting element D2 was produced in the same manner as Comparative Example CD1 except that "solvent" was used instead of "organic solvent 1".

By applying a voltage to the light-emitting element D2, EL emission is observed. The luminous efficiency of the light-emitting element D2 at 1000cd/ ^m2 is 4.8cd/A.

<Example D3> Production and evaluation of light-emitting element D3

In Comparative Example CD1 (formation of the light-emitting layer), in addition to using "KF-96 1000cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed in the organic solvent 1 at a concentration of 1000 mass ppm relative to the amount of the organic solvent 1 A light-emitting element D3 was produced in the same manner as Comparative Example CD1 except that "Solvent" was used instead of "Organic Solvent 1".

By applying a voltage to the light-emitting element D3, EL emission is observed. The luminous efficiency of the light-emitting element D3 at 1000cd/ ^m2 is 4.2cd/A.

Table 2 shows the results of Comparative Example CD1 and Examples D1, D2 and D3.

[Table 2]

<Comparative Example CD2> Production and evaluation of light-emitting element CD2

In Comparative Example CD1 (formation of light-emitting layer), light-emitting element CD2 was produced in the same manner as Comparative Example CD1, except that "polymer compound 3" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD2, EL emission is observed. The luminous efficiency of the light-emitting element CD2 at 1000cd/ ^m2 is 3.8cd/A.

<Comparative Example CD3> Production and evaluation of light-emitting element CD3

In Example D1 (formation of the light-emitting layer), a light-emitting element CD3 was produced in the same manner as in Example D1, except that "polymer compound 3" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD3, EL emission is observed. The luminous efficiency of the light-emitting element CD3 at 1000cd/ ^m2 is 3.0cd/A.

<Comparative Example CD4> Production and evaluation of light-emitting element CD4

In Example D2 (formation of light-emitting layer), a light-emitting element CD4 was produced in the same manner as Example D2 except that "polymer compound 3" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD4, EL emission is observed. The luminous efficiency of the light-emitting element CD4 at 1000cd/ ^m2 is 2.9cd/A.

<Comparative Example CD5> Production and evaluation of light-emitting element CD5

In Example D3 (formation of light-emitting layer), a light-emitting element CD5 was produced in the same manner as Example D3 except that "polymer compound 3" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD5, EL emission is observed. The luminous efficiency of the light-emitting element CD5 at 1000cd/ ^m2 is 2.6cd/A.

Table 3 shows the results of Comparative Examples CD2, CD3, CD4 and CD5.

[table 3]

<Comparative Example CD6> Production and evaluation of light-emitting element CD6

In Comparative Example CD1 (formation of light-emitting layer), light-emitting element CD6 was produced in the same manner as Comparative Example CD1, except that "polymer compound 4" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD6, EL emission is observed. The luminous efficiency of the light-emitting element CD6 is 0.2cd/A at 1000cd/ ^m2 .

<Comparative Example CD7> Production and evaluation of light-emitting element CD7

In Example D1 (formation of the light-emitting layer), a light-emitting element CD7 was produced in the same manner as in Example D1, except that "polymer compound 4" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD7, EL emission is observed. The luminous efficiency of the light-emitting element CD7 is 0.2cd/A at 1000cd/ ^m2 .

<Comparative Example CD8> Production and evaluation of light-emitting element CD8

In Example D2 (formation of light-emitting layer), a light-emitting element CD8 was produced in the same manner as Example D2 except that "polymer compound 4" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD8, EL emission is observed. The luminous efficiency of the light-emitting element CD8 at 1000cd/ ^m2 is 0.2cd/A.

<Comparative Example CD9> Production and evaluation of light-emitting element CD9

In Example D3 (formation of light-emitting layer), a light-emitting element CD9 was produced in the same manner as Example D3 except that "polymer compound 4" was used instead of "polymer compound 2".

By applying a voltage to the light-emitting element CD9, EL emission is observed. The luminous efficiency of the light-emitting element CD9 at 1000cd/ ^m2 is 0.2cd/A.

Table 4 shows the results of Comparative Examples CD6, CD7, CD8 and CD9.

[Table 4]

<Comparative Example CD10> Production and evaluation of light-emitting element CD10

The light-emitting element CD10 was produced in the same manner as the comparative example CD1, except that the hole transport layer and the light-emitting layer were formed in the following manner.

(Formation of hole transport layer)

Mix cyclohexylbenzene, 4-methoxytoluene, 3-phenoxytoluene, and 2,6-di-tert-butyl-4-methylphenol in a mass ratio of 48.39:29.97:21.63:0.01 In the resulting solvent (hereinafter, also referred to as "organic solvent 2"), polymer compound 5 is dissolved at a concentration of 0.6% by mass relative to the amount of organic solvent 2. The obtained solution was used to form a film with a thickness of 20 nm on the hole injection layer by spin coating, and was heated on a hot plate at 200° C. for 30 minutes in a nitrogen atmosphere to form a hole transport layer.

2,6-Di-tert-butyl-4-methylphenol

(Formation of luminescent layer)

In Comparative Example CD1 (formation of the light-emitting layer), in addition to using "a solution in which the polymer compound 6 is dissolved in the organic solvent 2 at a concentration of 0.9% by mass relative to the amount of the organic solvent 2" is used instead of "relative to the amount of the organic solvent 2" The light-emitting layer was formed in the same manner as in Comparative Example CD1, except that the amount of solvent 1 was "a solution in which the polymer compound 2 was dissolved in the organic solvent 1 at a concentration of 0.9% by mass."

By applying a voltage to the light-emitting element CD10, EL emission is observed. The luminous efficiency of the light-emitting element CD10 at 1000cd/ ^m2 is 1.9cd/A.

<Example D4> Production and evaluation of light-emitting element D4

In Comparative Example CD10 (Formation of Luminous Layer), in addition to using "polysilicone oil KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd., having formula (2)" (in the formula, B ¹ is a methyl group, s is 0 ), a polymer compound B) having a structural unit represented by formula (2) (in which B ¹ is a phenyl group and s is 0), relative to the amount of organic solvent 2, at 10 mass ppm A light-emitting element D4 was produced in the same manner as Comparative Example CD10, except that "the organic solvent 2" was replaced with "the solvent obtained by mixing the organic solvent 2 with the concentration".

By applying a voltage to the light-emitting element D4, EL emission is observed. The luminous efficiency of the light-emitting element D4 at 1000cd/ ^m2 is 4.2cd/A.

<Example D5> Production and evaluation of light-emitting element D5

In Comparative Example CD10 (formation of the light-emitting layer), in addition to using "KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed with the organic solvent 2 at a concentration of 100 mass ppm relative to the amount of the organic solvent 2" The light-emitting element D5 was produced in the same manner as Comparative Example CD10 except that "Solvent" was used instead of "Organic Solvent 2".

By applying a voltage to the light-emitting element D5, EL emission is observed. The luminous efficiency of the light-emitting element D5 at 1000cd/ ^m2 is 4.3cd/A.

<Example D6> Production and evaluation of light-emitting element D6

In Comparative Example CD10 (formation of the light-emitting layer), in addition to using "KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed with the organic solvent 2 at a concentration of 1000 mass ppm relative to the amount of the organic solvent 2" The light-emitting element D6 was produced in the same manner as Comparative Example CD10 except that "Solvent" was used instead of "Organic Solvent 2".

By applying a voltage to the light-emitting element D6, EL emission is observed. The luminous efficiency of the light-emitting element D6 is 2.2cd/A at 1000cd/ ^m2 .

Table 5 shows the results of Comparative Example CD10 and Examples D4, D5 and D6.

[table 5]

<Comparative Example CD11> Production and evaluation of light-emitting element CD11

In Comparative Example CD10 (Formation of Light-Emitting Layer), except that "Polymer Compound 6" is changed to "Polymer Compound 7" and "Polymer Compound 7" is dissolved at a concentration of 1.2% by mass relative to the amount of organic solvent 2 The obtained solution was used to form a film with a thickness of 85 nm, and a light-emitting element CD11 was produced in the same manner as Comparative Example CD10.

By applying a voltage to the light-emitting element CD11, EL emission is observed. The luminous efficiency of the light-emitting element CD11 at 1000 cd/ ^m is 3.6 cd/A.

<Example D7> Production and evaluation of light-emitting element D7

In Comparative Example CD11 (Formation of Light-Emitting Layer), in addition to using "KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) as a polysilicone oil was mixed with an organic solvent at a concentration of 10 ppm by mass relative to the amount of the organic solvent 2" The light-emitting element D7 was produced in the same manner as Comparative Example CD11 except that "the organic solvent 2" was replaced with "solvent 2".

By applying voltage to the light-emitting element D7, EL emission is observed. The luminous efficiency of the light-emitting element D7 is 5.6cd/A at 1000cd/ ^m2 .

<Example D8> Production and evaluation of light-emitting element D8

In Comparative Example CD11 (formation of the light-emitting layer), in addition to using "KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed with the organic solvent 2 at a concentration of 100 mass ppm relative to the amount of the organic solvent 2" The light-emitting element D8 was produced in the same manner as Comparative Example CD11 except that "Solvent" was used instead of "Organic Solvent 2".

By applying a voltage to the light-emitting element D8, EL emission is observed. The luminous efficiency of the light-emitting element D8 at 1000cd/ ^m2 is 6.0cd/A.

<Example D9> Production and evaluation of light-emitting element D9

In Comparative Example CD11 (formation of the light-emitting layer), in addition to using "KF-50 100cs (manufactured by Shin-Etsu Chemical Industry Co., Ltd.) mixed with the organic solvent 2 at a concentration of 1000 mass ppm relative to the amount of the organic solvent 2" The light-emitting element D9 was produced in the same manner as Comparative Example CD11 except that "Solvent" was used instead of "Organic Solvent 2".

By applying voltage to the light-emitting element D9, EL emission is observed. The luminous efficiency of the light-emitting element D9 at 1000cd/ ^m2 is 3.8cd/A.

Table 6 shows the results of Comparative Example CD11 and Examples D7, D8 and D9.

[Table 6]

Examples D1, D2 and D3 using polymer compound 2 and KF-96 1000cs, Examples D4, D5 and D6 using polymer compound 6 and KF-50 100cs, and examples D4, D5 and D6 using polymer compound 7 and KF-50 100cs. Embodiments D7, D8 and D9 have excellent luminous efficiency. Polymer compound 2, polymer compound 6 and polymer compound 7 are equivalent to polymer compound A and contain the structural unit represented by formula (1). KF-96 1000cs and KF-50 100cs are equivalent to polymer compound B. The inventors speculate that the reason why Examples D1 to D9 have excellent luminous efficiency is because the polymer compound A and the polymer compound B are used in combination. Polymer Compound 2, Polymer Compound 6, and Polymer Compound 7 have structural units derived from diamines having an aryl group belonging to a condensed ring, but the condensed ring usually tends to have a planar structure. The structural unit represented by the formula (1) having a condensed ring is likely to take a shape in which the condensed ring structures between molecules overlap. If such intermolecular interaction occurs, the non-radiation deactivation process will be promoted and the luminous efficiency will be improved. reduced possibility. However, the present inventors speculate that by using the polymer compound A and the polymer compound B together, the intermolecular interaction between the polymer compounds A is hindered, and as a result, the luminous efficiency is improved. In addition, polymer compound B has excellent chemical stability and does not degrade the light-emitting characteristics of the organic EL element, so it is suitable as a material used together with polymer compound A.

Claims (15)

A composition comprising: a polymer compound A containing a structural unit represented by formula (1), a polymer compound B containing a structural unit represented by formula (2), and a solvent;

In the formula, Ar represents an aryl group or a divalent heterocyclic group, and these groups may have substituents; when there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and to their respective The bonded atoms together form a ring; there are multiple Ar's that can be the same or different; Ar' is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. These groups may have substituents; when there are multiple such substituents, these substituents may be the same or different. , can also bond with each other and form a ring together with the atoms to which they are bonded; there are multiple Ar's that can be the same or different; Z is an aryl group belonging to a condensed ring or a divalent heterocyclic group belonging to a condensed ring. These groups may have substituents; when there are multiple such substituents, these substituents may be the same or different, or Can bond with each other and form rings together with the atoms to which they are bonded;

In the formula, B ¹ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxyalkyl group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom. These groups can Have substituents; when there are multiple such substituents, these substituents can be the same or different, or they can bond with each other and form a ring together with the atoms to which they are bonded; there are multiple B ^1s that can be the same It can also be different; s represents an integer above 0; multiple s can be the same or different. The composition according to claim 1, wherein the content of the aforementioned polymer compound A exceeds 1000 mass ppm relative to the aforementioned solvent, and the content of the aforementioned polymer compound B exceeds 0 mass ppm and is less than 1000 mass ppm relative to the aforementioned solvent. . The composition according to claim 1 or 2, wherein the aforementioned Ar is an aryl group which may have a substituent, and the aforementioned Ar' is an aryl group which may have a substituent. The composition according to claim 1 or 2, wherein the Ar is a phenylene group which may have a substituent, and the Ar' is a phenyl group which may have a substituent. The composition according to claim 1 or 2, wherein the aforementioned Z is a 2-ring, 3-ring, 4-ring, 5-ring or 6-ring aryl group, or a 2-ring, 3-ring, A 4-ring, 5-ring or 6-ring divalent heterocyclic group, these groups may have substituents. The composition according to claim 1 or 2, wherein Z is a tricyclic aryl group or a tricyclic divalent heterocyclic group, and these groups may have substituents. The composition according to claim 1 or 2, wherein the aforementioned B ¹ is an alkyl group or an aryl group, and these groups may have substituents. The composition according to claim 1 or 2, wherein the polymer compound A further includes at least one member selected from the group consisting of a structural unit represented by formula (Y) and a structural unit represented by formula (X). 1 type of structural unit;

In the formula, Ar ^Y1 represents an aryl group, a divalent heterocyclic group, or a divalent group in which at least one aryl group and at least one divalent heterocyclic group are directly bonded. These groups may have substituents; In the case where there are multiple such substituents, these substituents may be the same or different, or may be bonded to each other and form a ring together with the atoms to which they are bonded;

In the formula, a ^X1 and a ^X2 each independently represent an integer above 0; Ar ^X1 and ^Ar Bond to each other and form a ring with the atoms to which they are bonded; Ar ^X2 and ^Ar Substituents; when there are multiple such substituents, these substituents may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded; when there are multiple Ar ^X2 , they may be the same or different respectively; when there are multiple Ar ^X4s , they may be the same or different respectively; R ^X1 , R ^X2 and ^R These substituents may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded; when there are multiple R ^X2 , they may be the same or different; when there are multiple R In the case of ^X3 , these may be the same or different. The composition according to claim 8, wherein the polymer compound A contains a structural unit represented by formula (Y-1) or a structural unit represented by formula (Y-2) as the structural unit represented by formula (Y) constituent unit;

In the formula, R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, and these groups may have substituents; When there are multiple such substituents, these substituents may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded; the presence of multiple R ^Y1 may be the same or different, They can also bond with each other and form a ring together with the carbon atoms to which they are bonded; X ^Y1 represents the group represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -; R ^Y2 represents hydrogen atom, alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, aryloxy, monovalent heterocyclic group, substituted amino group or fluorine atom, these groups may have substituents; when there are multiple In the case of such substituents, these substituents may be the same or different, or they may be bonded to each other and form a ring together with the atoms to which they are bonded; the presence of multiple R ^Y2 may be the same or different, or they may be bonded to each other. Together with the carbon atoms to which they are bonded, they form a ring. The composition according to claim 1 or 2, wherein the solvent is an aromatic hydrocarbon solvent or an aromatic ether solvent. The composition according to claim 1 or 2, wherein the prosolvent contains two or more solvents. The composition according to claim 11, wherein at least one of the two or more solvents is an aromatic hydrocarbon solvent or an aromatic ether solvent. The composition according to claim 11, wherein at least two of the two or more solvents are at least two selected from the group consisting of aromatic hydrocarbon solvents and aromatic ether solvents. The composition of claim 1 or 2, which further contains at least one selected from the group consisting of hole transport materials, hole injection materials, electron transport materials, electron injection materials, luminescent materials and antioxidants. . A method of manufacturing a light-emitting element, the light-emitting element having an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, and The manufacturing method includes the step of forming at least one layer of the aforementioned organic layer by a wet method using the composition as described in claim 1 or 2.