阅读说明：本技术 高分子化合物、高分子化合物的制造方法及发光元件 (Polymer compound, method for producing polymer compound, and light-emitting element ) 是由 寺井宏树 于 2019-11-22 设计创作，主要内容包括：本发明提供向溶剂中的溶解速度快的高分子化合物及该高分子化合物的制造方法。本发明提供一种高分子化合物,其振实密度为0.02g/cm<Sup>3</Sup>以上且0.13g/cm<Sup>3</Sup>以下,包含选自以式(1－1)表示的构成单元及以式(1－2)表示的构成单元中的至少1个构成单元。本发明提供一种高分子化合物的制造方法,所述高分子化合物包含选自以式(1－1)表示的构成单元及以式(1－2)表示的构成单元中的至少1个构成单元,所述制造方法包括以下的工序,即,使含有包含选自以式(1－1)表示的构成单元及以式(1－2)表示的构成单元中的至少1个构成单元的高分子化合物、以及所述高分子化合物的良溶剂的混合物、与35℃以上且75℃以下的所述高分子化合物的不良溶剂混合,并取出所得的沉淀物。<Image he="318" wi="700" file="DDA0002658913990000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention provides a polymer compound having a high dissolution rate in a solvent and a method for producing the polymer compound. The present invention provides a polymer compound having a tap density of 0.02g/cm 3 Above and 0.13g/cm 3 The following includes at least 1 constituent unit selected from the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2). The present invention provides a method for producing a polymer compound containing a constituent unit selected from the group consisting of a constituent unit represented by the formula (1-1) and a constituent unit represented by the formula (1-2)The method for producing a polymer compound of (1) or more, the method comprising the step of mixing a mixture containing a polymer compound comprising at least 1 constituent unit selected from the group consisting of the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2) and a good solvent for the polymer compound with a poor solvent for the polymer compound at 35 ℃ or higher and 75 ℃ or lower, and taking out the obtained precipitate.)

1. A polymer compound which is a mixture of a polymer,

the tap density of the powder is 0.02g/cm³Above and 0.13g/cm³At least 1 constituent unit selected from the constituent unit represented by the following formula (1-1) and the constituent unit represented by the following formula (1-2);

in the formula (1-1),

a1 and a2 each independently represent an integer of 0 or more and 2 or less;

Ar^X1represents a direct bond, a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or at least 1 2-valent aromatic hydrocarbon group and at least 1A 2-valent group in which a 2-valent heterocyclic group is directly bonded, the groups optionally having a substituent;

Ar^X2、Ar^X3and Ar^X4Each independently represents a 2-valent group in which a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are directly bonded, and these groups optionally have a substituent; at Ar^X2And Ar^X4When a plurality of them are present, they are optionally the same or different;

R^X1、R^X2and R^X3Each independently represents an alkyl group, an aryl group or a 1-valent heterocyclic group, which groups may have a substituent; at R^X2And R^X3When a plurality of them are present, they are optionally the same or different;

in the formula (1-2), the metal salt,

R^Y1represents a hydrogen atom, an alkyl group, an aryl group or a 1-valent heterocyclic group, which may have a substituent; there are a plurality of R^Y1Optionally the same or different;

y represents-C (R)^Y2)₂－、－C(R^Y2)＝C(R^Y2)－、－C(R^Y2)₂－C(R^Y2)₂－、－C(R^Y2)₂－C(R^Y2)₂－C(R^Y2)₂－、－N(R^Y2) -or-O-represents a group;

R^Y2represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a 1-valent heterocyclic group, which may have a substituent; at R^Y2When plural are present, they may be the same or different, and plural R's are present^Y2Optionally bonded to each other to form a ring together with the carbon atom to which each is bonded; in the presence of a plurality of R^Y2When forming a ring, with-C (R)^Y2)₂-the group represented by (a) is a group represented by the formula (Y-1) to the formula (Y-5), which may have a substituent;

2. the polymer compound according to claim 1, which has a glass transition temperature of 80 ℃ or higher and 200 ℃ or lower.

3. A method for producing a polymer compound comprising at least 1 constituent unit selected from the group consisting of a constituent unit represented by the following formula (1-1) and a constituent unit represented by the following formula (1-2),

the production method comprises a step of mixing a mixture containing a polymer compound containing at least 1 constituent unit selected from the group consisting of the constituent unit represented by the following formula (1-1) and the constituent unit represented by the following formula (1-2), and a good solvent for the polymer compound, with a poor solvent for the polymer compound at 35 ℃ or higher and 75 ℃ or lower, and taking out the resulting precipitate;

in the formula (1-1),

a1 and a2 each independently represent an integer of 0 or more and 2 or less;

Ar^X1、Ar^X2、Ar^X3and Ar^X4Each independently represents a 2-valent group in which a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are directly bonded, and these groups optionally have a substituent; at Ar^X2And Ar^X4When a plurality of them are present, they are optionally the same or different;

R^X1、R^X2and R^X3Each independently represents an alkyl group, an aryl group or a 1-valent heterocyclic group, which groups may have a substituent; at R^X2And R^X3When a plurality of them are present, they are optionally the same or different;

in the formula (1-2), the metal salt,

R^Y1represents a hydrogen atom, an alkyl group, an aryl group or a 1-valent heterocyclic group, which may be substitutedA group; there are a plurality of R^Y1Optionally the same or different;

y represents-C (R)^Y2)₂－、－C(R^Y2)＝C(R^Y2)－、－C(R^Y2)₂－C(R^Y2)₂－、－N(R^Y2) -or-O-represents a group;

R^Y2represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a 1-valent heterocyclic group, which may have a substituent; at R^Y2When plural are present, they may be the same or different, and plural R's are present^Y2Optionally bonded to each other to form a ring together with the carbon atom to which each is bonded; in the presence of a plurality of R^Y2When forming a ring, with-C (R)^Y2)₂-the group represented by (a) is a group represented by the formula (Y-1) to the formula (Y-5), which may have a substituent;

4. the manufacturing method according to claim 3,

the good solvent is aromatic hydrocarbon.

5. The manufacturing method according to claim 3 or 4,

the poor solvent is 300 parts by weight or more per 100 parts by weight of the good solvent.

6. A light-emitting element comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, the organic layer being formed using the polymer compound according to claim 1 or 2.

Technical Field

The present invention relates to a polymer compound, a method for producing a polymer compound, and a light-emitting element.

Background

In order to produce an organic layer of an organic electroluminescent element by a coating method such as an inkjet printing method, research and development of a polymer compound soluble in a solvent as a material for forming the organic layer have been carried out. In order to efficiently produce an ink for coating, a polymer compound having a high dissolution rate in a solvent is required.

For example, non-patent document 1 describes a copolymer of propylene glycol 9, 9 '-dioctylfluorene-2, 7-diboronate and 4, 4' -dibromotriphenylamine as such a polymer compound.

Disclosure of Invention

Problems to be solved by the invention

However, the rate of dissolution of the polymer compound into the solvent is not necessarily sufficient.

Accordingly, an object of the present invention is to provide a polymer compound having a high dissolution rate in a solvent, a method for producing the polymer compound, and a light-emitting element using the polymer compound as a material.

Means for solving the problems

The present invention provides the following [1] to [5 ].

[1]A high molecular compound having a tap density of 0.02g/cm³Above and 0.13g/cm³The following includes at least 1 constituent unit selected from the constituent unit represented by the following formula (1-1) and the constituent unit represented by the following formula (1-2).

[ solution 1]

[ in the formula (1-1),

a1 and a2 each independently represent an integer of 0 to 2.

Ar^X1Represents a group having a valence of 2 obtained by directly bonding, a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or a 2-valent group obtained by directly bonding at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group, and these groups may have a substituent.

Ar^X2、Ar^X3And Ar^X4Each independently represents a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or a 2-valent group in which at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are directly bonded, and these groups may have a substituent. At Ar^X2And Ar^X4When a plurality of them are present, they are optionally the same or different.

R^X1、R^X2And R^X3Each independently represents an alkyl group, an aryl group or a 1-valent heterocyclic group, which may have a substituent. At R^X2And R^X3When a plurality of them are present, they are optionally the same or different.

In the formula (1-2), the metal salt,

R^Y1represents a hydrogen atom, an alkyl group, an aryl group or a 1-valent heterocyclic group, which may have a substituent. There are a plurality of R^Y1Optionally the same or different.

Y represents-C (R)^Y2)₂－、-C(R^Y2)＝C(R^Y2)－、－C(R^Y2)₂－C(R^Y2)₂－、-C(R^Y2)₂－C(R^Y2)₂－C(R^Y2)₂－、－N(R^Y2) -or-O-represents a group.

R^Y2Represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a 1-valent heterocyclic group, and these groups may have a substituent. At R^Y2When plural are present, they may be the same or different, and plural R's are present^Y2Optionally bonded to each other to formThe bonded carbon atoms together form a ring. In the presence of a plurality of R^Y2When forming a ring, with-C (R)^Y2)₂The group represented by (A) is a group represented by the formula (Y-1) to (Y-5), which may have a substituent.]

[ solution 2]

[2] The polymer compound according to [1], wherein the glass transition temperature is 80 ℃ or higher and 200 ℃ or lower.

[3] A method for producing a polymer compound containing at least 1 constituent unit selected from the group consisting of a constituent unit represented by the following formula (1-1) and a constituent unit represented by the following formula (1-2), comprising the step of mixing a mixture containing a polymer compound containing at least 1 constituent unit selected from the group consisting of a constituent unit represented by the following formula (1-1) and a constituent unit represented by the following formula (1-2) and a good solvent for the polymer compound, and a poor solvent for the polymer compound at 35 ℃ or higher and 75 ℃ or lower, and taking out the resulting precipitate.

[4] A light-emitting element comprising an anode, a cathode, and an organic layer formed between the anode and the cathode and formed using the polymer compound according to [1] or [2 ].

[ solution 3]

[ in the formula (1-1),

a1 and a2 each independently represent an integer of 0 to 2.

Ar^X1、Ar^X2、Ar^X3And Ar^X4Each independently represents a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or a 2-valent group in which at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are directly bonded, and these groups may have a substituent. At Ar^X2And Ar^X4When a plurality of them are present, they are optionally the same or different.

R^X1、R^X2And R^X3Each independently represents an alkyl group, an aryl group or a 1-valent heterocyclic group, which may have a substituent. At R^X2And R^X3When a plurality of them are present, they are optionally the same or different.

In the formula (1-2), the metal salt,

R^Y1represents a hydrogen atom, an alkyl group, an aryl group or a 1-valent heterocyclic group, which may have a substituent. There are a plurality of R^Y1Optionally the same or different.

Y represents-C (R)^Y2)₂-、-C(R^Y2)＝C(R^Y2)-、-C(R^Y2)₂-C(R^Y2)₂-、-N(R^Y2) -or-O-represents a group.

R^Y2Represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a 1-valent heterocyclic group, and these groups may have a substituent. At R^Y2When plural are present, they may be the same or different, and plural R's are present^Y2Optionally bonded to each other to form a ring together with the carbon atom to which each is bonded. In the presence of a plurality of R^Y2When forming a ring, with-C (R)^Y2)₂The group represented by (A) is a group represented by the formula (Y-1) to (Y-5), which may have a substituent.]

[ solution 4]

[4] The production method according to [3], wherein the good solvent is an aromatic hydrocarbon.

[5] The production method according to [3] or [4], wherein the poor solvent is 300 parts by weight or more per 100 parts by weight of the good solvent.

Effects of the invention

According to the present invention, a polymer compound having a high dissolution rate into a solvent and a method for producing the polymer compound can be provided.

Detailed Description

Preferred embodiments of the present invention will be described below.

Description of general terms

The terms used in the present specification have the following meanings unless otherwise specified.

The "hydrogen atom" may be a protium atom or a deuterium atom.

The "alkyl group" refers to a linear, branched or cyclic alkyl group. The number of carbon atoms of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20. The number of carbon atoms of the branched and cyclic alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20. Examples of the alkyl group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a 2-ethylbutyl group, a n-hexyl group, a cyclohexyl group, a n-heptyl group, a cyclohexylmethyl group, a cyclohexylethyl group, a n-octyl group, a 2-ethylhexyl group, a 3-n-propylheptyl group, a n-decyl group, a 3, 7-dimethyloctyl group, a 2-ethyloctyl group, a 2-n-hexyl-decyl group, and a n.

The "alkyl group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an aryl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex, and the like. The "alkyl group" optionally has 1 to 20 substituents selected from these substituents. Examples of the substituted alkyl group include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3- (4-methylphenyl) propyl group, a 3- (3, 5-di-n-hexylphenyl) propyl group, and a 6-ethyloxyhexyl group.

The "aryl group" refers to a 1-valent group obtained by removing 1 hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aromatic hydrocarbon is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10. Examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and a 4-fluorenyl group.

The "aryl group" may have a substituent, and examples of the substituent include a halogen atom (particularly, a fluorine atom), a cyano group, an alkyl group, an aryl group (the aryl group may have 1 to 3 substituents selected from the group consisting of an alkyl group and an alkoxy group), a heterocyclic group having a valence of 1, an alkoxy group, an aryloxy group, a substituted amino group, an alkylene group (e.g., a dimethylene group and a trimethylene group), and the like. The "aryl group" optionally has 1 to 10 substituents selected from these substituents. Examples of the substituted aryl group include a pentafluorophenyl group, a 4-hexylphenyl group, a 4-phenylphenyl group, and a benzocyclobutene group.

The "alkoxy group" refers to a straight-chain, branched-chain or cyclic alkoxy group. The number of carbon atoms of the linear alkoxy group is usually 1 to 40, preferably 4 to 10. The number of carbon atoms of the branched and cyclic alkoxy groups is usually 3 to 40, preferably 4 to 10. Examples of the alkoxy group include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a n-pentoxy group, a n-hexoxy group, a cyclohexyloxy group, a n-heptoxy group, a n-octoxy group, a 2-ethylhexoxy group, a n-nonyloxy group, a n-decyloxy group, a 3, 7-dimethyloctyloxy group, and a lauryloxy group.

The "alkoxy group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an aryl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex, and the like. The "alkoxy group" optionally has 1 to 10 substituents selected from these substituents.

The "aryloxy group" refers to a group having 1 valence in which 1 hydrogen atom directly bonded to a carbon atom constituting a ring is replaced with an oxygen atom from an aromatic hydrocarbon. The number of carbon atoms of the aryloxy group is usually 6 to 60, preferably 7 to 48. Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthryloxy group, a 9-anthryloxy group, and a 1-pyrenyloxy group.

The "aryloxy group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an alkyl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex, and the like. The "aryloxy group" optionally has 1 to 10 substituents selected from these substituents. Examples of the substituted aryloxy group include a pentafluorophenoxy group, a 4-hexylphenoxy group, a 4-phenylphenoxy group and the like.

"substituted amino" refers to an amino group having 2 substituents. Examples of the substituent include an alkyl group, an aryl group (the aryl group may have an alkyl group), a heterocyclic group having a valence of 1, and the like. Examples of the substituted amino group include a dialkylamino group, a diarylamino group, and a bis (mono-or dialkylaryl) amino group, and specific examples thereof include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis (4-methylphenyl) amino group, a bis (4-tert-butylphenyl) amino group, and a bis (3, 5-di-tert-butylphenyl) amino group.

By "esterified carboxy" is meant a compound of the formula: a group represented by-COOR '(R' represents an alkyl group, an aryl group, a 1-valent heterocyclic group, or the like). Examples of the esterified carboxyl group include an alkyloxycarbonyl group and an aryloxycarbonyl group, and specific examples thereof include a group represented by the formula-CO₂CH₃A group represented by-CO₂C₂H₅A group represented by-CO₂C₆H₅The group represented, and the like.

The "alkenyl group" may be any of linear, branched and cyclic groups. The number of carbon atoms of the linear alkenyl group is usually 2 to 30, preferably 2 to 20. The number of carbon atoms of the branched and cyclic alkenyl groups is usually 3 to 30, preferably 4 to 20. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-buten-1-yl group, a 3-buten-1-yl group, a 1-cyclohexenyl group, a 1-norbornyl group, and a 2-norbornyl group.

The "alkenyl group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an aryl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, a group containing a metal complex, and the like. The "alkenyl group" optionally has 1 to 20 substituents selected from these substituents. Examples of the substituted alkenyl group include a 2-phenylvinyl group, a 4-octyl-2-phenylvinyl group and the like.

The "alkynyl group" may be any of a straight chain, a branched chain and a cyclic group. The number of carbon atoms of the straight chain alkynyl group is usually 2 to 30, preferably 2 to 20. The number of carbon atoms of the branched or cyclic alkynyl group is usually 4 to 30, preferably 4 to 20. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-butyn-1-yl group, and a 3-butyn-1-yl group.

The "alkynyl group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an aryl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, a group containing a metal complex, and the like. The "alkynyl group" optionally has 1 to 20 substituents selected from these substituents. Examples of the substituted alkynyl group include a 2-phenylethynyl group, a 4-octyl-2-phenylethynyl group and the like.

The "group containing a metal complex" means a group containing a complex formed of a metal atom and a ligand coordinated to the metal atom. Examples thereof include groups represented by any of the formulae (C-1) to (C-4).

[ wherein M is Ir or Pt. When M is Ir, M is 2, and when M is Pt, M is 1. Ring a represents an optionally substituted cyclic structure containing a nitrogen atom. Ring B represents a cyclic structure containing a carbon atom, which may have a substituent. R represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, an aryl group, a heterocyclic group having a valence of 1, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex. In the case where R is a group capable of substitution, it may have a substituent. When there are plural R, they may be the same or different. Adjacent R's are optionally bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

Examples of the ring a include nitrogen-containing aromatic rings (e.g., pyridine). Examples of the ring B include an aromatic ring (e.g., benzene) and a heteroaromatic ring (e.g., dibenzothiophene). Ring A and ring B optionally have a substituent. The ring A and the ring B each optionally have 1 to 4 substituents selected from, for example, a fluorine atom, a cyano group, an alkyl group, an aryl group, a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, and the like.

The "2-valent aromatic hydrocarbon group" refers to a 2-valent group obtained by removing 2 hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon, and a 2-valent group obtained by bonding a plurality of (for example, 2 to 5) groups selected from the 2-valent group. The number of carbon atoms of the 2-valent aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18. Examples of the 2-valent aromatic hydrocarbon group include phenylene, naphthalenediyl, anthracenediyl, phenanthrenediyl, dihydrophenanthrenediyl, tetracenediyl, fluorenediyl, pyrenediyl, perylenediyl, perylene-diyl, and the like,Diradicals, and the like.

The "2-valent aromatic hydrocarbon group" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an alkyl group, an aryl group (the aryl group may have 1 to 5 substituents selected from the group consisting of an alkyl group, an alkoxy group, a phenyl group and an alkylphenyl group), a 1-valent heterocyclic group, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex, and the like. The "2-valent aromatic hydrocarbon group" optionally has 1 to 10 substituents selected from these substituents. Examples of the optionally substituted 2-valent aromatic hydrocarbon group include groups represented by the formulae (A-1) to (A-20).

[ in the formula, R represents the same meaning as described above. ]

The "heterocyclic group having a valence of 1" refers to a group having a valence of 1 obtained by removing 1 hydrogen atom from a heterocyclic compound among hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting a ring. Among the heterocyclic groups having a valence of 1, preferred is a heterocyclic group having a valence of 1 obtained by removing 1 hydrogen atom from an aromatic heterocyclic compound among hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting the ring, that is, an "aromatic heterocyclic group having a valence of 1". Examples of the "1-valent heterocyclic group" include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidyl group, a quinolyl group, an isoquinolyl group, a pyrimidyl group, and a triazinyl group.

The "aromatic heterocyclic compound" also refers to a compound in which the heterocycle itself exhibits aromatic properties, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzosilacyclopentadiene, and dibenzophosphole; phenoxazines, phenothiazines, dibenzoboroles, dibenzosilales, benzopyrans and the like, in which an aromatic ring is fused to a heterocyclic ring although the heterocyclic ring itself does not exhibit aromatic properties; and any of compounds in which a plurality of these compounds are bonded.

The "heterocyclic group having a valence of 1" may have a substituent, and examples of the substituent include a halogen atom (particularly, a fluorine atom), a cyano group, an alkyl group, an aryl group, a heterocyclic group having a valence of 1, an alkoxy group, an aryloxy group, a substituted amino group, an alkylene group, and the like. The heterocyclic group having a valence of 1 optionally has 1 to 5 substituents selected from these substituents.

The "heterocyclic group having a valence of 2" refers to a group having a valence of 2 obtained by removing 2 hydrogen atoms from a heterocyclic compound among hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting a ring. Among the heterocyclic groups having a valence of 2, a heterocyclic group having a valence of 2 obtained by removing 2 hydrogen atoms from among hydrogen atoms directly bonded to carbon atoms or hetero atoms constituting a ring from an aromatic heterocyclic compound, that is, "a heterocyclic aromatic group having a valence of 2" is preferable. Examples of the "heterocyclic group having a valence of 2" include a group having a valence of 2 obtained by removing 2 hydrogen atoms from an aromatic heterocyclic compound such as pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, dibenzothiophene, dibenzosilacyclopentadiene, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, oxazole, oxadiazole, triazole, oxazole, oxadiazole, thiazole, thiadiazole, which is directly bonded to a carbon atom or a heteroatom constituting a ring, and a group having a valence of 2 obtained by bonding a plurality of (for example, 2 to 4) groups selected from the group having a valence of 2.

The "heterocyclic group having a valence of 2" may have a substituent, and examples of the substituent include a fluorine atom, a cyano group, an alkyl group, an aryl group, a heterocyclic group having a valence of 1, an alkoxy group, an aryloxy group, a substituted amino group, a carboxyl group, an esterified carboxyl group, an alkenyl group, an alkynyl group, a group containing a metal complex, and the like. The 2-valent heterocyclic group optionally has 1 to 5 substituents selected from these substituents. The optionally substituted 2-valent heterocyclic group is preferably a group represented by the formulae (A-21) to (A-45).

[ in the formula, R represents the same meaning as described above. ]

The "2-valent group in which at least 1 2-valent aromatic hydrocarbon group is bonded to at least 1 2-valent heterocyclic group" means a 2-valent group in which 1 or 2 or more of the above 2-valent aromatic hydrocarbon groups are optionally bonded to 1 or 2 or more of the above 2-valent heterocyclic groups. The aromatic hydrocarbon group having a valence of 2 and the heterocyclic group having a valence of 2 may be the above-mentioned groups.

The "2-valent group in which at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are bonded" may have a substituent, and the 2-valent aromatic hydrocarbon group as a partial structure thereof may have 1 to 10 substituents selected from the above-mentioned fluorine atom, cyano group, alkyl group, aryl group, 1-valent heterocyclic group, alkoxy group, aryloxy group, substituted amino group, carboxyl group, esterified carboxyl group, alkenyl group, alkynyl group, and group containing a metal complex, and the 2-valent heterocyclic group as another partial structure may have 1 to 5 substituents selected from the above-mentioned fluorine atom, cyano group, alkyl group, aryl group, 1-valent heterocyclic group, alkoxy group, aryloxy group, substituted amino group, carboxyl group, esterified carboxyl group, alkenyl group, alkynyl group, and group containing a metal complex.

The "constituent unit" means that 1 or more units are present in the polymer compound.

< Polymer >

The polymer compound of the present invention has a tap density of 0.02g/cm³Above and 0.13g/cm³A polymer compound comprising at least 1 constituent unit selected from the group consisting of the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2).

The tap density is preferably 0.03g/cm in order to increase the dissolution rate of the polymer compound of the present invention in a solvent³Above, more preferably 0.04g/cm³Above, more preferably 0.05g/cm³The above. Further, it is preferably 0.12g/cm³Hereinafter, more preferably 0.11g/cm³Hereinafter, more preferably 0.10g/cm³The following. The polymer compound having a tap density within the above range has a high dissolution rate in the solvent.

The above upper limit and lower limit may be arbitrarily combined.

[ constituent Unit represented by formula (1-1) ]

As a1, 0 or 1 is preferable.

As a2, 0 is preferable.

As Ar^X1The aromatic hydrocarbon group having a valence of 2 or a heterocyclic group having a valence of 2 is preferably directly bonded, and the aromatic hydrocarbon group having a valence of 2 is more preferably used.

As Ar^X2、Ar^X3And Ar^X4The aromatic hydrocarbon group having a valence of 2 or the heterocyclic group having a valence of 2 is preferable, and the aromatic hydrocarbon group having a valence of 2 is more preferable.

As R^X1、R^X2And R^X3Preferably an alkyl group or an aryl group, more preferably an aryl group.

Examples of the constituent unit represented by formula (1-1) include constituent units represented by formulae (X-1) to (X-9), preferably formulae (X-1) to (X-7), and more preferably formulae (X-3) to (X-7).

[ in the formula, R represents the same meaning as described above. ]

In the polymer compound of the present invention, the constituent unit represented by the formula (1-1) is usually 0 to 100 mol% based on the total amount of the constituent units contained in the polymer compound, and in order to increase the dissolution rate of the polymer compound of the present invention in a solvent, it is preferably 0 mol% or more and 90 mol% or less, more preferably 0 mol% or more and 80 mol% or less, and still more preferably 0 mol% or more and 70 mol% or less. In the polymer compound of the present invention, the constituent unit represented by the formula (1-1) is preferably 5 mol% or more and 90 mol% or less, more preferably 5 mol% or more and 80 mol% or less, and still more preferably 5 mol% or more and 70 mol% or less, with respect to the total amount of the constituent units contained in the polymer compound, from the viewpoint of hole-transporting property. However, when the constituent unit represented by the formula (1-1) is 0% based on the total amount of the constituent units contained in the polymer compound, the constituent unit represented by the formula (1-2) is contained in an amount of 1% or more.

The constituent unit represented by the formula (1-1) may contain only 1 species or 2 or more species in the polymer compound.

[ constituent Unit represented by formula (1-2) ]

As R^Y1Preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

As Y, it is preferable to use-C (R)^Y2)₂-、-C(R^Y2)＝C(R^Y2)-、-C(R^Y2)₂-C(R^Y2)₂A group represented by-C (R) is more preferred^Y2)₂-a group represented by (a).

As R^Y2Preferably an alkyl or aryl group, more preferably an alkyl group.

At a plurality of R^Y2When they are bonded to each other to form a ring together with the carbon atoms to which they are bonded, -C (R)^Y2)₂A group represented by the formula (Y-4)The group shown.

Examples of the structural unit represented by formula (1-2) include structural units represented by formulae (YY-1) to (YY-7), preferably formulae (YY-1) to (YY-5), and more preferably formulae (YY-1) to (YY-3).

[ in the formula, R represents the same meaning as described above. ]

In the polymer compound of the present invention, the constituent unit represented by the formula (1-2) is usually 0 to 100 mol% based on the total amount of the constituent units contained in the polymer compound, and in order to increase the dissolution rate of the polymer compound of the present invention in a solvent, it is preferably 0 mol% or more and 90 mol% or less, more preferably 0 mol% or more and 80 mol% or less, and still more preferably 0 mol% or more and 70 mol% or less. In the polymer compound of the present invention, the constituent unit represented by the formula (1-2) is preferably 5 mol% or more and 90 mol% or less, more preferably 5 mol% or more and 80 mol% or less, and still more preferably 5 mol% or more and 70 mol% or less, with respect to the total amount of the constituent units contained in the polymer compound, from the viewpoint of electron transport properties. However, when the constituent unit represented by the formula (1-2) is 0% based on the total amount of the constituent units contained in the polymer compound, the constituent unit represented by the formula (1-1) is contained in an amount of 1% or more.

The constituent unit represented by the formula (1-2) may contain only 1 species or 2 or more species in the polymer compound.

In the polymer compound of the present invention, when the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2) are contained, the content of the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2) is usually 1 to 100 mol% based on the total amount of the constituent units contained in the polymer compound, and in order to increase the dissolution rate of the polymer compound of the present invention into a solvent, it is preferably 5 mol% or more and 100 mol% or less, more preferably 10 mol% or more and 100 mol% or less, and still more preferably 15 mol% or more and 100 mol% or less.

[ other constituent units ]

The polymer compound of the present invention may contain a constituent unit represented by the formula (1-1) and "another constituent unit" other than the constituent unit represented by the formula (1-2).

The "other constituent unit" is a 2-valent organic group, and examples of the 2-valent organic group include a 2-valent group in which only 1 or 2 or more 2-valent aromatic hydrocarbon groups are directly bonded, a 2-valent group in which only 1 or 2 or more 2-valent heterocyclic groups are directly bonded, or a 2-valent group in which at least 1 2-valent aromatic hydrocarbon group is directly bonded to at least 1 2-valent heterocyclic group, and the 2-valent organic group may be formed by directly bonding the 2 or more 2-valent aromatic hydrocarbon groups, the 2 or more 2-valent heterocyclic groups, or the 2-valent group in which the at least 1 2-valent aromatic hydrocarbon group is directly bonded to at least 1 2-valent heterocyclic group, or may be formed via a group selected from alkylene groups (for example, - (CR)₂) - (wherein R represents the same meaning as above). ) At least 1 group of the group represented by-O-, the group represented by-S-, and the group represented by- (CO) -is bonded to form a 2-valent organic group.

Among the above-mentioned 2-valent organic groups, a 2-valent group in which a 2-valent aromatic hydrocarbon group, a 2-valent heterocyclic group, or at least 1 2-valent aromatic hydrocarbon group and at least 1 2-valent heterocyclic group are directly bonded is preferable.

Examples of the "other constituent unit" include constituent units represented by the formulae (Z-1) to (Z-8), preferably the formulae (Z-1) to (Z-6), and more preferably the formulae (Z-1) to (Z-4).

In the polymer compound of the present invention, the "other constituent unit" is preferably 0 to 90 mol%, more preferably 2 to 80 mol%, and further preferably 3 to 70 mol% based on the total amount of constituent units contained in the polymer compound.

The "other constituent unit" may be contained in the polymer compound by only 1 kind, or may be contained by 2 or more kinds.

The polymer compound of the present invention has a molecular weight distribution, and the weight average molecular weight (Mw) in terms of polystyrene is preferably 1 × 10³～1×10⁸More preferably 1 × 10, most preferably 1 ×⁴～1×10⁶More preferably 3 × 10⁴～5×10⁵The range of (1).

The polymer compound of the present invention may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in other forms, and is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.

The polymer compound of the present invention is preferably a polymer compound having a glass transition temperature of 80 ℃ to 200 ℃. From the viewpoint of increasing the dissolution rate into the solvent, the temperature is preferably 85 ℃ or higher, more preferably 90 ℃ or higher, and still more preferably 95 ℃ or higher. Further, it is preferably 190 ℃ or lower, more preferably 170 ℃ or lower, and still more preferably 120 ℃ or lower.

The above upper limit and lower limit may be combined arbitrarily.

For example, the glass transition temperature is preferably 85 ℃ or more and 170 ℃ or less, and more preferably 95 ℃ or more and 120 ℃ or less.

< method for producing Polymer Compound >

The method for producing a polymer compound of the present invention comprises: a step 1 of obtaining a mixture containing a polymer compound A containing at least 1 constituent unit selected from the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2), and a good solvent for the polymer compound A; a step 2 of mixing the mixture obtained in the step 1 with a poor solvent for the polymer compound a at 35 ℃ to 75 ℃ to obtain a precipitate; and a step 3 of taking out the precipitate obtained in the step 2.

The precipitate is a polymer compound of the present invention.

Hereinafter, the step 1 will be described in detail. The mixture obtained in step 1 is referred to as "mixture of step 1".

[ Polymer A ]

The constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2) contained in the polymer compound A are each as defined above.

The polymer compound A may contain a constituent unit represented by the formula (1-1) and "another constituent unit" other than the constituent unit represented by the formula (1-2).

The "other constituent unit" has the same meaning as described above.

In the polymer compound a, the constituent unit represented by the formula (1-1) is usually 0 to 100 mol% based on the total amount of the constituent units contained in the polymer compound a, and in order to increase the dissolution rate of the polymer compound of the present invention in a solvent, it is preferably 0 mol% or more and 90 mol% or less, more preferably 0 mol% or more and 80 mol% or less, and still more preferably 0 mol% or more and 70 mol% or less. In the polymer compound a, the constituent unit represented by the formula (1-1) is preferably 5 mol% or more and 90 mol% or less, more preferably 5 mol% or more and 80 mol% or less, and still more preferably 5 mol% or more and 70 mol% or less, with respect to the total amount of the constituent units contained in the polymer compound a, from the viewpoint of the hole-transporting property of the polymer compound of the present invention. However, when the constituent unit represented by the formula (1-1) is 0% based on the total amount of the constituent units contained in the polymer compound A, the constituent unit represented by the formula (1-2) is contained in an amount of 1% or more.

The constituent unit represented by the formula (1-1) may be contained in the polymer compound a in only 1 kind, or may be contained in 2 or more kinds.

In the polymer compound a, the constituent unit represented by the formula (1-2) is usually 0 to 100 mol% relative to the total amount of the constituent units contained in the polymer compound a, and in order to increase the dissolution rate of the polymer compound of the present invention in a solvent, it is preferably 0 mol% or more and 90 mol% or less, more preferably 0 mol% or more and 80 mol% or less, and still more preferably 0 mol% or more and 70 mol% or less. In the polymer compound a, the constituent unit represented by the formula (1-2) is preferably 5 mol% or more and 90 mol% or less, more preferably 5 mol% or more and 80 mol% or less, and still more preferably 5 mol% or more and 70 mol% or less, with respect to the total amount of the constituent units contained in the polymer compound a, from the viewpoint of electron transport properties of the polymer compound of the present invention. However, when the constituent unit represented by the formula (1-2) is 0% based on the total amount of the constituent units contained in the polymer compound a, the constituent unit represented by the formula (1-1) is contained in an amount of 1% or more.

The constituent unit represented by the formula (1-2) may be contained in the polymer compound a only in 1 kind, or may be contained in 2 or more kinds.

In the case where the polymer compound a contains the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2), the content of the constituent unit represented by the formula (1-1) and the constituent unit represented by the formula (1-2) is usually 1 to 100 mol% based on the total amount of the constituent units contained in the polymer compound a, and in order to increase the dissolution rate of the polymer compound of the present invention into a solvent, it is preferably 5 mol% or more and 100 mol% or less, more preferably 10 mol% or more and 100 mol% or less, and still more preferably 15 mol% or more and 100 mol% or less.

In the polymer compound a, "other constituent unit" is preferably 0 to 90 mol%, more preferably 2 to 80 mol%, and further preferably 3 to 70 mol% based on the total amount of constituent units contained in the polymer compound a.

The other constituent units may be contained in the polymer compound a only in 1 kind, or may be contained in 2 or more kinds.

The polymer compound A has a molecular weight distribution, and the weight-average molecular weight (Mw) in terms of polystyrene is preferably 1 × 10³～1×10⁸More preferably 1 × 10⁴～1×10⁶More preferably 3 × 10⁴～5×10⁵The range of (1).

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

The polymer compound a can be obtained by polymerizing a monomer containing a chlorine atom or a bromine atom, for example. Examples of the polymerization method include a method of polymerizing a monomer by Suzuki coupling reaction, a method of polymerizing by Buchwald coupling reaction, a method of polymerizing by Stille coupling reaction, a method of polymerizing by Kumada coupling reaction, and a method of polymerizing by Yamamoto coupling reaction. Among them, from the viewpoint of ease of structure control of the polymer compound a, a method of polymerization by Suzuki coupling reaction and a method of polymerization by Buchwald coupling reaction are preferable.

When the purity of the polymer compound a is low, the purification can be carried out by a usual method such as liquid separation, recrystallization, reprecipitation, column chromatography, Soxhlet washing (Soxhlet washing), or the like, as necessary.

[ good solvent ]

The good solvent is a solvent capable of dissolving the polymer compound a without decomposing the polymer compound a, and a solvent having a solubility of the polymer compound a of 1g (polymer compound a)/100g (good solvent) or more at 20 ℃.

Examples of the good solvent include aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, cyclohexylbenzene, and tetralin; ether solvents such as tetrahydrofuran, 1, 4-dioxane, dimethoxyethane, and anisole; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; halogenated hydrocarbon solvents such as chloroform and chlorobenzene. Among them, aromatic hydrocarbon solvents and ether solvents are preferable, aromatic hydrocarbon solvents are more preferable, and toluene, xylene, and mesitylene are further preferable.

As the good solvent, 1 kind of solvent may be used, and 2 kinds of solvents may also be used.

The content of the good solvent in the mixture of the step 1 is usually 100 to 1000000 parts by weight, preferably 500 to 100000 parts by weight, based on 100 parts by weight of the polymer compound a.

Hereinafter, the step 2 will be described in detail.

[ poor solvent ]

The poor solvent is a solvent in which the polymer compound a is difficult to dissolve without decomposing the polymer compound a, and a solvent in which the solubility of the polymer compound a is less than 1g (polymer compound a)/100g (poor solvent) at 20 ℃.

Examples of the poor solvent include water; amide solvents such as N, N-dimethylacetamide and N, N-dimethylformamide; alcohol solvents such as methanol, ethanol, isopropanol, ethylene glycol, isopropyl alcohol, and propylene glycol; nitrile solvents such as acetonitrile; ester solvents such as methyl acetate and ethyl acetate. Among these, alcohol solvents are preferable, methanol, ethanol, and isopropanol are more preferable, and methanol is further preferable.

As the poor solvent, 1 kind of solvent may be used, and 2 kinds of solvents may be used.

The temperature of the poor solvent is preferably 40 ℃ or higher. Further, it is preferably 70 ℃ or lower, more preferably 65 ℃ or lower, and still more preferably 60 ℃ or lower. When the mixture obtained in step 1 is mixed with a poor solvent, the dissolution rate of the polymer compound of the present invention into the solvent becomes high by using the poor solvent in the above range.

The above upper limit and lower limit may be combined arbitrarily.

For example, the temperature of the poor solvent is preferably 40 ℃ or higher and 60 ℃ or lower.

The amount of the poor solvent used is usually 100 to 10000 parts by weight, preferably 200 to 5000 parts by weight, and more preferably 300 to 2000 parts by weight, based on 100 parts by weight of the good solvent.

In step 2, when the mixture of step 1 is mixed with a poor solvent, the polymer compound of the present invention precipitates.

In the step 2, the mixing may be:

(a) the mixture of step 1 may be mixed by adding the poor solvent to the mixture, or may be:

(b) the poor solvent is added to the mixture of the step 1 and mixed, and may be:

(c) the mixture of step 1 and the poor solvent are added simultaneously to a vessel and mixed.

Among them, the (a) is preferable, and the (a) is preferably performed in a state where the poor solvent is stirred. In the above (a), the rate of adding the poor solvent to the mixture of the step 1 is usually 1 g/min to 10000000 g/min, and is preferably 10 g/min to 1000000 g/min from the viewpoint of increasing the dissolution rate of the polymer compound of the present invention into the solvent.

The stirring time is usually 1 minute to 10 hours, preferably 10 minutes to 2 hours.

Examples of the stirring method include a method using a combination of an electric stirrer and a stirring blade, a combination of an air motor stirrer and a stirring blade, a combination of a magnetic stirrer and a stirrer, and the like.

The stirring power during the stirring is preferably 0.01kW/m in order to increase the dissolution rate of the polymer compound of the present invention into the solvent³Above, more preferably 0.05kW/m³The above is more preferably 0.2kW/m³The above. Further, it is preferably 5.0kW/m³Hereinafter, more preferably 3.0kW/m³Hereinafter, more preferably 1.0kW/m³The following.

In the step 2, the temperature of the mixture of the step 1 when the mixture of the step 1 is mixed with the poor solvent is usually-20 to 100 ℃, preferably 0 to 75 ℃, and more preferably 0 to 30 ℃.

Hereinafter, the step 3 will be described in detail.

Step 3 is a step of taking out the precipitate as the polymer compound of the present invention in step 2. The method for removing the precipitate includes, for example, filtration. The precipitate removed by filtration may be washed with the poor solvent.

If necessary, the precipitate may be dried to remove the good solvent and/or the poor solvent contained in the precipitate. Examples of the drying method include a heating method, a pressure-reducing method, an air-drying method, and a combination thereof.

< light emitting element >

The light-emitting element of this embodiment mode is a light-emitting element including an anode, a cathode, and an organic layer, the organic layer being provided between the anode and the cathode, and the organic layer including a film formed using the polymer compound of the present invention. Examples of the organic layer include a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer. At least 1 layer of these is a film formed using the polymer compound of the present invention.

The polymer compound of the present invention may contain a group having a chemical structure such as benzocyclobutene, olefin (alkone), epoxy, or oxetane (hereinafter referred to as a crosslinking group) which forms a crosslinked structure by a crosslinking reaction, and the film can be insolubilized by crosslinking the crosslinking group after the film is formed using the polymer compound having the crosslinking group. By thus insolubilizing the film, even when a material of the film is dissolved in a solvent used in forming a layer adjacent to an organic layer including the film in a light-emitting element, the material can be prevented from being dissolved.

The organic layer included in the light-emitting element according to the embodiment of the present invention may be a film containing the polymer compound of the present invention, which is formed without a step such as insolubilization of the film due to the crosslinking.

[ layer constitution ]

The film containing the polymer compound of the present invention is usually 1 or more layers selected from a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and is preferably a hole-transporting layer.

These layers respectively contain a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. These layers can be formed by dissolving a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material in the above-described good solvent, preparing an ink, and then using the ink, by a common film-forming method such as spin coating.

The light-emitting element has a light-emitting layer between an anode and a cathode. The light-emitting element of this embodiment preferably has at least 1 of the hole injection layer and the hole transport layer between the anode and the light-emitting layer from the viewpoint of hole injection property and hole transport property, and preferably has at least 1 of the electron injection layer and the electron transport layer between the cathode and the light-emitting layer from the viewpoint of electron injection property and electron transport property.

The materials of the hole transport layer, the electron transport layer, the light-emitting layer, the hole injection layer, and the electron injection layer may include a hole transport material, an electron transport material, a light-emitting material, a hole injection material, an electron injection material, and the like, in addition to the materials included in the film containing the polymer compound of the present invention.

When the material for the hole transport layer, the material for the electron transport layer, and the material for the light-emitting layer are each dissolved in a solvent used for forming a layer adjacent to the hole transport layer, the electron transport layer, and the light-emitting layer in the production of the light-emitting element, the materials preferably have a crosslinking group in order to avoid the dissolution of the materials in the solvent. After each layer is formed using a material having a crosslinking group, the crosslinking group is crosslinked, whereby the layer can be insolubilized.

In the light-emitting element of the present embodiment, as a method for forming each layer such as the light-emitting layer, the hole-transporting layer, the electron-transporting layer, the hole-injecting layer, and the electron-injecting layer, when a low-molecular compound is used, for example, a vacuum vapor deposition method using powder or a method for forming a film using a solution or a molten state is mentioned, and when a high-molecular compound is used, for example, a method for forming a film using a solution or a molten state is mentioned. The order, number, and thickness of the stacked layers are adjusted in consideration of light emission efficiency and luminance lifetime.

[ substrate/electrode ]

The substrate of the light-emitting element may be any substrate that can form an electrode and does not chemically change when an organic layer is formed, and examples of the substrate include substrates made of materials such as glass, plastic, and silicon. In the case of an opaque substrate, the electrode furthest from the substrate is preferably transparent or translucent.

Examples of the material of the anode include conductive metal oxides and translucent metals, and indium oxide, zinc oxide, and tin oxide are preferable; conductive compounds such as Indium Tin Oxide (ITO) and indium zinc oxide; silver and palladium and copper complexes (APC); NESA, gold, platinum, silver, copper.

Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of 2 or more of them; alloys of 1 or more of them with 1 or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite intercalation compounds. Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.

The anode and the cathode may have a laminated structure of 2 or more layers.

[ use ]

The light-emitting element of the present embodiment can be used for a display of a computer, a television, a portable terminal, or the like. The planar light emitting element can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar light source for illumination. When a flexible substrate is used, the substrate can also be used as a curved light source or a display device.