WO2017170314A1

WO2017170314A1 - Light-emitting element

Info

Publication number: WO2017170314A1
Application number: PCT/JP2017/012226
Authority: WO
Inventors: 敏明佐々田; 大介福島
Original assignee: 住友化学株式会社
Priority date: 2016-03-29
Filing date: 2017-03-27
Publication date: 2017-10-05
Also published as: JP6979400B2; JPWO2017170314A1

Abstract

A light-emitting element having a positive electrode, a negative electrode, and a first organic layer and a second organic layer that are provided between the positive electrode and the negative electrode, wherein the first organic layer is a layer that includes a light-emitting material expressed by formula (B), the maximum peak wavelength of the emission spectrum of the light-emitting material expressed by formula (B) is 380nm-750nm, the second organic layer is a layer that includes a crosslinked body of a high-molecular compound, said high-molecular compound including a structural unit that has a group expressed by formula (XL-A) and a structural unit that has a group expressed by formula (XL-B), and the group expressed by formula (XL-A) and the group expressed by formula (XL-B) are different groups.

Description

Light emitting element

The present invention relates to a light emitting element.

Light emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications, and research and development are being conducted.

For example, Patent Document 1 discloses an organic layer containing a polymer compound (P0-1) containing a structural unit represented by the following formula (M0-1) and a light emission represented by the following formula (EM0-1). A light-emitting element having a light-emitting layer containing a material is described. The polymer compound (P0-1) is a polymer compound having no crosslinking group.

For example, Patent Document 2 discloses an organic layer containing a crosslinked product of a polymer compound (P0-2) represented by the following formula and a light emitting layer containing a light emitting material represented by the following formula (EM0-2) Are described. The polymer compound (P0-2) includes a crosslinked structural unit having a group represented by the formula (XL-A) described later and a crosslinked structural unit having a group represented by the formula (XL-B). Different from polymer compounds.

International Publication No. 2007-100010 JP 2010-183010 A

As a light-emitting element, one having a sufficiently low driving voltage is required. Therefore, an object of the present invention is to provide a light emitting element with a low driving voltage.

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

[1] A light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer containing a light emitting material represented by the formula (B),
The maximum peak wavelength of the emission spectrum of the luminescent material represented by the formula (B) is 380 nm or more and 750 nm or less,
The second organic layer contains a crosslinked product of a polymer compound containing a structural unit having a group represented by the formula (XL-A) and a structural unit having a group represented by the formula (XL-B) Layer to
A light-emitting element in which the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different from each other.

[Where:
n ^1B represents an integer of 0 to 15.
Ar ^1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
R ^1B is a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group or cycloalkynyl. Represents a group, and these groups may have a substituent. When there are a plurality of R ^{1B s} , they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

[Where:
nA and nB each independently represents an integer of 0 to 5.
L ^A and L ^B each independently represent an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom, It may have a substituent. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of L ^A and L ^B , they may be the same or different from each other.
X ^A and X ^B each independently represent a crosslinking group. ]
[2] The light emitting device according to [1], wherein X ^A or X ^B is at least one crosslinking group selected from the crosslinking group A group.

[Wherein R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ]
[3] The crosslinked structural unit having a group represented by the formula (XL-A) is a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). The light emitting device according to [1] or [2].

[Where:
n ^A1 represents an integer of 1 to 4. When a plurality of n ^A1 are present, they may be the same or different.
n ^A2 represents an integer of 0 or 1.
^XLA represents a bridging group represented by the formula (XL-A), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. When a plurality of ^XLA are present, they may be the same or different. However, at least one ^XLA is a crosslinking group represented by the formula (XL-A).
Ar ^A3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar ^A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar ^A4 and Ar ^A6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^A4 , Ar ^A5 and Ar ^A6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be. ]
[4] The crosslinked structural unit having a group represented by the formula (XL-B) is a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). The light emitting device according to [1] or [2].

[Where:
n ^B1 represents an integer of 1 to 4. When a plurality of n ^B1 are present, they may be the same or different.
n ^B2 represents an integer of 0 or 1.
X ^LB represents a bridging group represented by the above formula (XL-B), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. When a plurality of X ^LB are present, they may be the same or different. However, at least one X ^LB is a bridging group represented by the formula (XL-B).
Ar ^B3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar ^B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar ^B4 and Ar ^B6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^B4 , Ar ^B5, and Ar ^B6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be. ]
[5] wherein ^{X A} is formula selected from the crosslinking group A (XL-3), formula (XL-4), the formula (XL-13) or Formula bridging group represented by (XL-17) The light emitting device according to any one of [2] to [4].
[6] The formula (XL-1), formula (XL-2), formula (XL-5), formula (XL-6), formula (XL-7) wherein X ^B is selected from the bridging group A group Any one of [2] to [5], which is a crosslinking group represented by formula (XL-8), formula (XL-14), formula (XL-15), or formula (XL-16) Light emitting element.
[7] The light emitting device according to any one of [1] to [6], wherein Ar ^1B is an aromatic hydrocarbon group.
[8] The Ar ^1B is a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, The light emission according to [7], which is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an indene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring. element.
[9] Ar ^1B has at least one hydrogen atom directly bonded to a carbon atom constituting the ring from a biphenyl ring, a fluorene ring, a pyrene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring. The light emitting device according to [8], which is a group formed by removal.
[10] The light emitting device according to any one of [1] to [9], wherein the n ^1B is an integer of 1 to 8.
[11] The above-mentioned R ^1B is an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, or a cycloalkenyl group (these groups may have a substituent), [1] to [10] The light emitting element in any one.
[12] The first organic layer is a layer containing a light emitting material represented by the formula (B) and a host material, and the host material is a compound or a formula represented by the formula (FH-1) The light-emitting device according to any one of [1] to [11], which is a polymer compound including a structural unit represented by (Y).

[Where:
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups optionally have a substituent.
n ^H1 represents an integer of 0 to 15.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R ^H11 ) ₂ ] n ^H11 —, and these groups ^optionally have a substituent. When a plurality of L ^H1 are present, they may be the same or different. n ^H11 represents an integer of 1 to 10. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ]
[13] The light emitting device according to any one of [1] to [12], wherein a maximum peak wavelength of an emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 570 nm or less.
[14] The light emitting device according to any one of [1] to [13], wherein the first organic layer and the second organic layer are adjacent to each other.
[15] The light emitting device according to any one of [1] to [14], wherein the second organic layer is a layer provided between the anode and the first organic layer.

According to the present invention, a light emitting element with a low driving voltage can be provided.

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

<Explanation of common terms>
Terms commonly used in this specification have the following meanings unless otherwise specified.

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 tert-butyl group.

The hydrogen atom may be a deuterium atom or a light hydrogen atom.

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

“Polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ .

“Low molecular weight compound” means a compound having no molecular weight distribution and a molecular weight of 1 × 10 ⁴ or less.

“Structural unit” means one or more units present in a polymer compound.

The “alkyl group” may be either linear or branched. 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, excluding the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.

Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group, heptyl. Group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group and dodecyl group. The alkyl group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be. Examples of the alkyl group having a substituent include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, and 3- (4-methylphenyl). A propyl group, a 3- (3,5-di-hexylphenyl) propyl group and a 6-ethyloxyhexyl group can be mentioned.

The number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.

Examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group. The cycloalkyl group may have a substituent. For example, part or all of the hydrogen atoms in the cycloalkyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, and the like. It may be a substituted group. Examples of the cycloalkyl group having a substituent include a cyclohexylmethyl group and a cyclohexylethyl group.

“Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the number of carbon atoms of the substituent.

Examples of the aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, and 4-phenylphenyl group. The aryl group may have a substituent. For example, part or all of the hydrogen atoms in the aryl group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.

The “alkoxy group” may be either linear or branched. The number of carbon atoms of the straight-chain alkoxy group is usually 1 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.

Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group and lauryloxy group. The alkoxy group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkoxy group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be.

The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.

Examples of the cycloalkoxy group include a cyclopentyloxy group and a cyclohexyloxy group. The cycloalkoxy group may have a substituent. For example, part or all of the hydrogen atoms in the cycloalkoxy group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, and the like. It may be a substituted group.

“Aryloxy group” means an atomic group in which one aryl group is bonded to an oxygen atom. The number of carbon atoms of the aryloxy group is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.

Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group. The aryloxy group may have a substituent. For example, part or all of the hydrogen atoms in the aryloxy group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like. It may be a group.

The “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.

`` Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc. A compound in which the ring itself exhibits aromaticity, and a compound in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran Means.

The number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.

Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, and triazinyl group. The monovalent heterocyclic group may have a substituent. For example, part or all of the hydrogen atoms in the monovalent heterocyclic group are an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and the like. It may be a substituted group.

“Halogen atom” means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The “amino group” may have a substituent, and a substituted amino group is preferable. As a substituent which an amino group has, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.

Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group. Specific examples of the substituted amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, and bis (3,5- A di-tert-butylphenyl) amino group.

The “alkenyl group” may be either linear or branched. The number of carbon atoms of the straight chain alkenyl group is usually 2 to 30, preferably 3 to 20, not including the carbon atoms of the substituent. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the carbon atoms of the substituent.

The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.

Examples of the alkenyl group and cycloalkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5 -Hexenyl group and 7-octenyl group. The alkenyl group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkenyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be. In addition, the cycloalkenyl group may have a substituent. For example, a part or all of the hydrogen atoms in the cycloalkenyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.

The “alkynyl group” may be either linear or branched. The number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent. The number of carbon atoms of the branched alkynyl group is usually from 4 to 30, and preferably from 4 to 20, not including the carbon atom of the substituent.

The number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.

Examples of the alkynyl group and cycloalkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group and 5 -A hexynyl group is mentioned. The alkynyl group may have a substituent, for example, a group in which some or all of the hydrogen atoms in the alkynyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be. In addition, the cycloalkynyl group may have a substituent. For example, a part or all of the hydrogen atoms in the cycloalkynyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.

“Arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.

Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, and a chrysenediyl group. The arylene group may have a substituent. For example, part or all of the hydrogen atoms in the arylene group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.

The arylene group is preferably a group represented by formula (A-1) to formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

In the formula, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. A plurality of R and R ^a may be the same or different, and R ^a may be bonded to each other to form a ring together with the atoms to which each is bonded.

The number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 without including the number of carbon atoms of the substituent.

Examples of the divalent heterocyclic group include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, Examples thereof include divalent groups obtained by removing two hydrogen atoms from a hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound such as diazole or triazole. The divalent heterocyclic group may have a substituent. For example, some or all of the hydrogen atoms in the divalent heterocyclic group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryls. It may be a group substituted with a group, a fluorine atom or the like.

The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

In the formula, R and R ^a represent the same meaning as described above.

The “crosslinking group” is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. This is a group represented by the formula (XL-1) to (XL-17) of the group A group.

Examples of the “substituent” include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, Examples include alkenyl group, cycloalkenyl group, alkynyl group and cycloalkynyl group. The substituent may be a crosslinking group.

<Light emitting element>
Next, a light emitting device according to an embodiment of the present invention will be described.

The light emitting device according to the present embodiment includes an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode. The first organic layer is a layer containing a light-emitting material represented by the formula (B) (hereinafter also referred to as “first light-emitting material”), and the second organic layer has a formula (XL-A And a crosslinked structural unit of a polymer compound containing a crosslinked structural unit having a group represented by formula (XL-B) and a crosslinked structural unit having a group represented by the formula (XL-B).

Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum deposition method and a wet method such as a spin coating method and an ink jet printing method, and a wet method is preferable.

When the first organic layer is formed by a wet method, it is preferable to use an ink for a first organic layer described below (hereinafter also referred to as “first ink”).

In the case where the second organic layer is formed by a wet method, it is preferable to use an ink for a second organic layer described below (hereinafter also referred to as “second ink”). After forming the second organic layer, the polymer compound of the second organic layer described later contained in the second organic layer can be crosslinked by heating or light irradiation. It is preferable to crosslink the polymer compound of the second organic layer described later contained in the second organic layer. When the second organic layer is contained in the second organic layer in a state where the polymer compound of the second organic layer described later is crosslinked (crosslinked product of the polymer compound of the second organic layer described later), the second organic layer Is substantially insolubilized in the solvent. Therefore, the second organic layer can be suitably used for stacking light emitting elements.

The heating temperature for crosslinking is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 ° C to 200 ° C, and still more preferably 170 ° C to 190 ° C. The heating time for crosslinking is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1 to 120 minutes, and further preferably 30 to 90 minutes. .

The types of light used for light irradiation are, for example, ultraviolet light, near ultraviolet light, and visible light.

Examples of the analysis method of the components contained in the first organic layer or the second organic layer include chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.

By subjecting the first organic layer or the second organic layer to solid-liquid extraction using an organic solvent such as toluene, xylene, chloroform, tetrahydrofuran, etc., components that are substantially insoluble in the organic solvent (insoluble Component) and a component that dissolves in an organic solvent (dissolved component). Insoluble components can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and dissolved components can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.

<First organic layer>
The first organic layer is a layer containing a first light emitting material. In the first organic layer, the first light emitting material may be contained singly or in combination of two or more.

[First Luminescent Material]

The maximum peak wavelength of the emission spectrum of the first luminescent material is usually 380 nm or more and 750 nm or less, preferably 380 nm or more and 570 nm or less, more preferably 400 nm or more and 550 nm or less, and further preferably 420 or more and 520 nm or less. It is particularly preferably 430 nm or more and 510 nm or less.

In this specification, the maximum peak wavelength of the emission spectrum of a compound is determined by dissolving the compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, and preparing a dilute solution (1 × 10 ⁻⁶ to 1 × 10 ⁻³ It can be evaluated by measuring the PL spectrum of the diluted solution at room temperature. As the organic solvent for dissolving the compound, toluene is preferable.

The first light emitting material is a compound represented by the formula (B).

[Compound represented by Formula (B)]
n ^1B represents an integer of 0 to 15, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 4, and particularly preferably 2 to 4 Is an integer.

Ar ^1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.

In Ar ^1B, aromatic carbon atoms of the hydrocarbon group has usually 6 to 60, preferably 6 to 40, more preferably 6 to 30.

Examples of the aromatic hydrocarbon group in Ar ^1B include benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene. And a group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the ring, chrysene ring, indene ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring. The aromatic hydrocarbon group is preferably a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene A group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from a ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring, and more preferably a benzene ring or biphenyl A ring is composed of a ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring. Bond directly to carbon atom A group formed by removing one or more elemental atoms, more preferably a benzene ring, biphenyl ring, naphthalene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, fluoranthene ring, benzofluoranthene ring or asena A group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the fluorfluorene ring, particularly preferably a biphenyl ring, a naphthalene ring, a fluorene ring, a pyrene ring, a perylene ring, a fluoranthene A ring, a benzofluoranthene ring or an acenaphthofluoranthene ring, a group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring, particularly preferably a biphenyl ring, a fluorene ring, a pyrene Ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring A group formed by removing one or more hydrogen atoms directly bonded to a carbon atom, and more preferably, a ring is composed of a pyrene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring A group formed by removing one or more hydrogen atoms directly bonded to a carbon atom.

In Ar ^1B , the number of carbon atoms of the aromatic heterocyclic group is usually 2 to 60, preferably 3 to 30, and more preferably 3 to 20.

Examples of the aromatic heterocyclic group in Ar ^1B include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an indole ring, and a benzodi ring. Azole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, phenazine ring or Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a 5,10-dihydrophenazine ring. The aromatic heterocyclic group is preferably a diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring. , A phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, and a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring, more preferably A hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, benzodiazole ring, benzotriazole ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring Except for one That is a group.

Ar ^1B is preferably an aromatic hydrocarbon group.

R ^1B is a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group or cycloalkynyl. Represents a group, and these groups may have a substituent. R ^1B is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an alkenyl group or a cycloalkenyl group, more preferably , An alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group. Or a cycloalkenyl group, particularly preferably an alkyl group, an aryl group or an alkenyl group, and particularly preferably an aryl group. These groups may further have a substituent.

When R ^1B is an aryl group, the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30 excluding the number of carbon atoms of the substituent. More preferably, it is 6-14.

When R ^1B is an aryl group, examples of the aryl group include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, And a group formed by removing one hydrogen atom directly bonded to the carbon atom constituting the ring from the perylene ring, chrysene ring, indene ring, fluoranthene ring and benzofluoranthene ring. The aryl group is preferably a carbon atom that forms a ring from a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring, fluoranthene ring or benzofluoranthene ring. A group formed by removing one hydrogen atom directly bonded to the ring, more preferably, a ring is composed of a benzene ring, naphthalene ring, anthracene ring, fluorene ring, spirobifluorene ring, fluoranthene ring or benzofluoranthene ring A group formed by removing one hydrogen atom directly bonded to a carbon atom, more preferably, more preferably from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, directly to the carbon atom constituting the ring. A group formed by removing one hydrogen atom to be bonded, particularly preferably Phenyl group, a naphthyl group or a fluorenyl group. These groups may further have a substituent.

When R ^1B is a monovalent heterocyclic group, the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 30, not including the number of carbon atoms of the substituent. Yes, more preferably 3-20.

When R ^1B is a monovalent heterocyclic group, examples of the monovalent heterocyclic group include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, and a diazanaphthalene. Ring, triazanaphthalene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a phenazine ring and a 5,10-dihydrophenazine ring. The monovalent heterocyclic group is preferably a pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine. A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, more preferably , A pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, except for one hydrogen atom directly bonded to the carbon atom or hetero atom constituting the ring Is a group. These groups may further have a substituent.

The substituent that R ^1B may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, or an alkenyl group. Or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, and still more preferably an alkyl group. A cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, particularly preferably an alkyl group or an aryl group. These groups may further have a substituent.

Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that R ^1B may have are the same as examples and preferred ranges of the aryl group and monovalent heterocyclic group in R ^1B , respectively. is there.

The substituent that the substituent which R ^1B may have may further include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group. Group, halogen atom, alkenyl group or cycloalkenyl group, more preferably an alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, alkenyl group or cycloalkenyl group. More preferred are an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, and particularly preferred is an alkyl group or a cycloalkyl group. These groups may further have a substituent.

Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the substituent which R ^1B may further have may further include the aryl group and monovalent complex in R ^1B , respectively. Examples of the cyclic group and the preferred range are the same.

Since the maximum peak wavelength of the emission spectrum of the compound represented by the formula (B) is a short wavelength, when there are a plurality of R ^1B , it is preferable that they are bonded to each other and do not form a ring with the atoms to which they are bonded.

Examples of the compound represented by the formula (B) include a compound represented by the following formula.

The compound represented by the formula (B) is Aldrich, Luminescence Technology Corp. , AK Scientific, etc. In addition, for example, International Publication No. 2007/100010, International Publication No. 2008/059713, International Publication No. 2011/012212, International Publication No. 2012/096263, International Publication No. 2006/025273, International Publication No. 2006 / 030527 can be synthesized according to the method described in US Pat.

[Host material]
Since the driving voltage of the light emitting device according to this embodiment is lower, the first organic layer is composed of the first light emitting material and the group consisting of hole injecting property, hole transporting property, electron injecting property, and electron transporting property. A layer containing a host material having at least one function selected from When the first organic layer is a layer containing the first light emitting material and the host material, the host material may be contained singly or in combination of two or more.

In the case where the first organic layer is a layer containing the first light emitting material and the host material, the content of the first light emitting material is 100 parts by mass of the total of the first light emitting material and the host material. In this case, it is usually 0.05 to 80 parts by mass, preferably 0.1 to 50 parts by mass, more preferably 1 to 30 parts by mass, and further preferably 5 to 15 parts by mass.

When the first organic layer is a layer containing the first light emitting material and the host material, the lowest excited singlet state (S ₁ ) of the host material is that the driving voltage of the light emitting element according to this embodiment is Since it becomes lower, it is preferable that it is the energy level equivalent to S1 which a _1st light emitting material has, or a higher energy level. That is, the maximum peak wavelength of the emission spectrum of the host material is equal to or shorter than the maximum peak wavelength of the emission spectrum of the first light emitting material because the external quantum efficiency of the light emitting device according to this embodiment is excellent. It is preferable.

As the host material, since the light-emitting element according to this embodiment can be manufactured by a solution coating process, the host material is soluble in a solvent capable of dissolving the first light-emitting material contained in the first organic layer. It is preferable.

∙ Host materials are classified into low molecular compounds and high molecular compounds. As a host material, the below-mentioned hole transport material and the below-mentioned electron transport material are mentioned, for example.

[Low molecular host]
A low molecular compound (hereinafter also referred to as “low molecular host”) that is preferable as a host material will be described.

The low molecular host is preferably a compound represented by the formula (FH-1).

Ar ^H1 and Ar ^H2 are preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.

When Ar ^H1 and Ar ^H2 are aryl groups, the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 30, and more preferably not including the number of carbon atoms of the substituent. 6 to 20, more preferably 6 to 14.

When Ar ^H1 and Ar ^H2 are aryl groups, examples of the aryl group include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from a pyrene ring, a perylene ring, a chrysene ring, an indene ring, a fluoranthene ring or a benzofluoranthene ring. The aryl group is preferably a hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring or chrysene ring. More preferably, one hydrogen atom directly bonded to the carbon atom constituting the ring is selected from a benzene ring, naphthalene ring, anthracene ring, pyrene ring, fluorene ring or spirobifluorene ring. A group to be excluded, more preferably a phenyl group, a naphthyl group or an anthracenyl group, and particularly preferably a phenyl group or a naphthyl group. These groups may further have a substituent.

When Ar ^H1 and Ar ^H2 are monovalent heterocyclic groups, the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 60, not including the number of carbon atoms of the substituent. -30, more preferably 3-20.

When Ar ^H1 and Ar ^H2 are monovalent heterocyclic groups, examples of the monovalent heterocyclic group include a pyrrole ring, diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, Diazanaphthalene ring, triazanaphthalene ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring , 9,10-dihydroacridine ring, acridone ring, phenazine ring and 5,10-dihydrophenazine ring, a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring. The monovalent heterocyclic group is preferably a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an indole ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a phenoxazine. A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a ring, a phenothiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine ring, more preferably , A diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, directly bonded to the carbon atom or heteroatom constituting the ring Except one atom That is a group. These groups may further have a substituent.

When Ar ^H1 and Ar ^H2 are substituted amino groups, the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. It may be. Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in Ar ^H1 and Ar ^H2 . Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in Ar ^H1 and Ar ^H2 .

The substituent that Ar ^H1 and Ar ^H2 may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group. Or a halogen 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 amino group, and still more preferably an alkyl group or a cycloalkyl group A group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group. These groups may further have a substituent.

Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that Ar ^H1 and Ar ^H2 may have are the aryl group and monovalent complex in Ar ^H1 and Ar ^H2 , respectively. The examples and preferred ranges of the cyclic group and the substituted amino group are the same.

As the substituent that the substituent that Ar ^H1 and Ar ^H2 may have further may preferably have, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, A cycloalkoxy group, an aryloxy group, a substituted amino group or a halogen 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 amino group. More preferably, they are an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent.

Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the substituent which Ar ^H1 and Ar ^H2 may have further have, and preferred ranges thereof are Ar ^H1 and Ar ^H1 , respectively. Examples of the aryl group, monovalent heterocyclic group and substituted amino group in Ar ^H2 are the same as the preferred range.

n ^H1 is preferably an integer of 0 to 10, more preferably an integer of 1 to 5, and still more preferably an integer of 1 to 3.

L ^H1 is preferably an arylene group or a divalent heterocyclic group, and more preferably an arylene group.

Examples and preferred ranges of the substituent that L ^H1 may have are the same as examples and preferred ranges of the substituent that Ar ^H1 and Ar ^H2 may have.

The arylene group in L ^H1 is preferably a group represented by the formula (A-1) to the formula (A-14) or the formula (A-17) to the formula (A-20), more preferably the formula A group represented by formula (A-1) to formula (A-9), formula (A-11) to formula (A-14), formula (A-19) or formula (A-20), more preferably Is a group represented by formula (A-1) to formula (A-7), formula (A-9), formula (A-11) to formula (A-14), or formula (A-19) Particularly preferred are groups represented by formula (A-1) to formula (A-6), formula (A-11) or formula (A-12).

The divalent heterocyclic group in L ^H1 is preferably the formula (AA-1) to formula (AA-6), formula (AA-10) to formula (AA-22) or formula (AA-24) to formula And more preferably a group represented by formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15), formula (AA-18) ) To formula (AA-21) or formula (AA-27) to formula (AA-34), more preferably formula (AA-1) to formula (AA-4), formula (AA) It is a group represented by AA-10) to formula (AA-15) or formula (AA-27) to formula (AA-32).

n ^H11 is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1.

R ^H11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and a hydrogen atom or an alkyl group. More preferably. These groups may have a substituent.

Examples and preferred ranges of the substituent that R ^H11 may have are the same as examples and preferred ranges of the substituent that Ar ^H1 and Ar ^H2 may have.

Examples of the compound represented by the formula (FH-1) include compounds represented by the following formula.

[Polymer host]
A polymer compound (hereinafter also referred to as “polymer host”) preferable as a host material will be described.

The polymer host is preferably a polymer compound containing a structural unit represented by the formula (Y).

The arylene group represented by Ar ^Y1 is preferably formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A-11), -13) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9), formula (A-11) or formula A group represented by (A-19); These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^Y1 is preferably the formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) Or a group represented by formula (AA-20), more preferably a group represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) It is. These groups may have a substituent.

Preferred range and more preferred range of arylene group and divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded. ^Are respectively the same as the preferred range and more preferred range of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described above.

As the divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded, at least represented by Ar ^X2 and Ar ^X4 in the formula (X) Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.

The substituent that the group represented by Ar ^Y1 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group. These groups may further have a substituent.

Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-7). From the viewpoint of the driving voltage of the light emitting device according to this embodiment. Is preferably a structural unit represented by the formula (Y-1) or (Y-2), and preferably from the viewpoint of electron transport properties of the polymer host, the formula (Y-3) or the formula ( Y-4), and from the viewpoint of the hole transport property of the polymer host, it is preferably a structural unit represented by formula (Y-5) to formula (Y-7).

In the formula, R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

R ^Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. These groups may have a substituent.

The structural unit represented by the formula (Y-1) is preferably a structural unit represented by the formula (Y-1 ′).

In the formula, R ^Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y11 may be the same or different.

R ^Y11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and more preferably an alkyl group or a cycloalkyl group. These groups may have a substituent.

In the formula, R ^Y1 represents the same meaning as described above. X ^Y1 ^{_{is, -C (R Y2) 2 -}} , - represents a group represented by - 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, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y2 may be the same or different, and R ^Y2 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

R ^Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups have a substituent. May be.

The combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ₂ — in X ^Y1 is preferably both an alkyl group or a cycloalkyl group, both an aryl group, and both monovalent complex One is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group. These groups may have a substituent. Two R ^{Y2 s} may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, the group represented by —C (R ^Y2 ) ₂ — Is preferably a group represented by the formula (Y-A1) to the formula (Y-A5), more preferably a group represented by the formula (Y-A4). These groups may have a substituent.

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ═C (R ^Y2 ) — is preferably both an alkyl group or a cycloalkyl group, or one of which is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group. These groups may have a substituent.

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a substituent which may have a substituent. It is a cycloalkyl group that may have. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — The group represented is preferably a group represented by the formula (Y-B1) to the formula (Y-B5), and more preferably a group represented by the formula (Y-B3). These groups may have a substituent.

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

The structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).

In the formula, R ^Y1 and X ^Y1 represent the same meaning as described above.

In the formula, R ^Y1 represents the same meaning as described above. R ^Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

R ^Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group. These groups may have a substituent.

In the formula, R ^Y1 represents the same meaning as described above. R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.

R ^Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.

Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-11) to the formula (Y-56), and preferably the formula (Y-11) to the formula (Y Y-55).

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, has a lower driving voltage of the light-emitting element according to the present embodiment. The amount is preferably 10 to 100 mol%, more preferably 50 to 100 mol%, based on the total amount.

A structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. The structural unit which is a group is preferably 0.5 to 40 mol%, more preferably 3%, based on the total amount of the structural units contained in the polymer host, since the charge transport property of the polymer host is excellent. ˜30 mol%.

In the polymer host, only one type of structural unit represented by the formula (Y) may be contained, or two or more types may be contained.

Since the polymer host is excellent in hole transportability, it is preferable that the polymer host further includes a structural unit represented by the formula (X).

Where
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. And these groups may have a substituent. When a plurality of Ar ^X2 and Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
When a plurality of R ^X2 and R ^X3 are present, they may be the same or different.

a ^X1 is preferably an integer of 2 or less, more preferably 1, since the driving voltage of the light emitting device according to the present embodiment becomes lower.

a ^X2 is preferably an integer of 2 or less, more preferably 0, because the driving voltage of the light emitting device according to the present embodiment becomes lower.

R ^X1 , R ^X2 and R ^X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.

The arylene group represented by Ar ^X1 and Ar ^X3 is preferably a group represented by the formula (A-1) or the formula (A-9), more preferably a group represented by the formula (A-1). It is. These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 is preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). It is a group. These groups may have a substituent.

Ar ^X1 and Ar ^X3 are preferably an arylene group which may have a substituent.

The arylene group represented by Ar ^X2 and Ar ^X4 is preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11) or A group represented by formula (A-19); These groups may have a substituent.

The preferred range of the divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 is the same as the preferred range of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 .

Preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and the at least one divalent heterocyclic group are directly bonded, More preferable ranges are the same as the preferable range and the more preferable range of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 , respectively.

Examples of the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulae: These may have a substituent.

In the formula, R ^XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

Ar ^X2 and Ar ^X4 are preferably an arylene group which may have a substituent.

The substituent that the group represented by Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group. These groups may further have a substituent.

The structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1) to the formula (X-7), more preferably the formula (X-3) to the formula (X -7), more preferably structural units represented by formulas (X-3) to (X-6).

In the formula, R ^X4 and R ^X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group. These groups may have a substituent. A plurality of R ^X4 may be the same or different. A plurality of R ^X5 may be the same or different, and adjacent R ^X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably based on the total amount of the structural units contained in the polymer host. It is 1 to 40 mol%, and more preferably 5 to 30 mol%.

Examples of the structural unit represented by the formula (X) include structural units represented by the formula (X1-1) to the formula (X1-19), preferably the formula (X1-6) to the formula (X1 -14).

In the polymer host, only one type of structural unit represented by the formula (X) may be included, or two or more types of structural units may be included.

Examples of the polymer host include polymer compounds (P-1) to (P-6) shown in Table 1. Here, the “other structural unit” means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).

In Table 1, p, q, r, s, and t represent the molar ratio of each structural unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70.

In the polymer compounds (P-1) to (P-6), examples of structural units represented by the formula (X) and the formula (Y) and preferred ranges thereof are as described above.

The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by polymerization is preferred.

The number average molecular weight in terms of polystyrene of the polymer host is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ⁴ to 5 × 10 ⁵ , and even more preferably 1.5 × 10 ^4. ~ 2 × 10 ⁵ .

[Method for producing polymer host]
The polymer host can be produced by using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc., and the Suzuki reaction, Buchwald reaction, Stille Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Negishi reaction and a Kumada reaction.

In the polymerization method, as a method of charging the monomer, a method of charging the entire amount of the monomer into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.

Examples of transition metal catalysts include palladium catalysts and nickel catalysts.

Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination. When the purity of the polymer host is low, it can be purified by usual methods such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, and the like.

[First composition]
The first organic layer is composed of the first light emitting material and the above-described host material, hole transport material, hole injection material, electron transport material, electron injection material, antioxidant, and second light emitting material. It may be a layer containing a composition containing at least one material selected from the group (hereinafter also referred to as “first composition”). However, in the first composition, the second light emitting material is different from the first light emitting material.

[Hole transport material]
The hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound. The hole transport material may have a crosslinking group.

Examples of the polymer compound include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof. The polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, and fullerene is preferable.

In the first composition, the compounding amount of the hole transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, when the first light emitting material is 100 parts by mass.

The hole transport material may be used alone or in combination of two or more.

[Electron transport materials]
Electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may have a crosslinking group.

Examples of the low molecular weight compounds include phosphorescent compounds having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene. And diphenoquinone, and derivatives thereof.

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

In the first composition, the compounding amount of the electron transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass when the first light emitting material is 100 parts by mass.

The electron transport material may be used alone or in combination of two or more.

[Hole injection material and electron injection material]
The hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively. The hole injection material and the electron injection material may have a crosslinking group.

Examples of low molecular weight 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.

Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.

In the first composition, the compounding amounts of the hole injecting material and the electron injecting material are each usually 1 to 400 parts by mass, preferably 5 to 150 parts when the first light emitting material is 100 parts by mass. Part by mass.

The electron injection material and the hole injection material may be used alone or in combination of two or more.

[Ion dope]
When the hole injection material or the electron injection material includes a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ S / cm to 1 × 10 ³ S / cm. In order to make the electric conductivity of the conductive polymer within such a range, the conductive polymer can be doped with an appropriate amount of ions.

The kind of ions to be doped is an anion for a hole injection material and a cation for an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

The ions to be doped may be used alone or in combination of two or more.

[Second Luminescent Material]
The second light emitting material is classified into a low molecular compound and a high molecular compound. The second light emitting material may have a crosslinking group.

Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.

Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, a structural unit represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine. Examples thereof include polymer compounds containing a diyl group, an anthracene diyl group, a pyrenediyl group, and the like.

The second light emitting material preferably contains a triplet light emitting complex and / or a polymer compound.

Examples of the triplet light-emitting complex include the metal complexes shown below.

In the first composition, the blending amount of the second light emitting material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, when the first light emitting material is 100 parts by weight.

The second luminescent material may be used alone or in combination of two or more.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the first light-emitting material and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the first luminescent material is 100 parts by mass.

Antioxidants may be used alone or in combination of two or more.

[First ink]
As the first ink for forming the first organic layer, a composition containing a first light emitting material and a solvent can be used. The first ink is spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method. In addition, it can be suitably used for wet methods such as offset printing, ink jet printing, capillary coating, and nozzle coating.

The viscosity of the first ink may be adjusted according to the type of wet method. However, when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging at the time of discharge and flight bending occur. Since it is difficult, it is preferably 1 to 20 mPa · s at 25 ° C.

The solvent contained in the first ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate system Medium; polyhydric alcohol solvents such as ethylene glycol, glycerin and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N, Examples include amide solvents such as N-dimethylformamide. A solvent may be used individually by 1 type, or may use 2 or more types together.

In the first ink, the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the first light emitting material is 100 parts by mass.

<Second organic layer>
The second organic layer includes a polymer compound (hereinafter referred to as “a cross-linking structural unit having a group represented by the formula (XL-A)” and a cross-linking structural unit having a group represented by the formula (XL-B). It is also a layer containing a crosslinked product of "second organic layer polymer compound".

In the second organic layer, the crosslinked polymer compound of the second organic layer may be contained singly or in combination of two or more.

The crosslinked product of the polymer compound of the second organic layer can be obtained by bringing the polymer compound of the second organic layer into a crosslinked state by the above-described method and conditions.

[High molecular compound of the second organic layer]
In the polymer compound of the second organic layer, “the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different from each other” means that nA and nB are different. , L ^A and L ^B are different, or X ^A and X ^B are different.

nA and nB each independently represent an integer of 0 to 5, and since the driving voltage of the light emitting device according to the present embodiment is lower, it is preferably an integer of 0 to 3, more preferably 0 to 2. It is an integer.

When nA and nB are different, since synthesis is easy, one of nA and nB is preferably 0 or 1, one is 0 and the other is 1 or 2, or Is more preferably 1 and the other is preferably 0 or 2.

L ^A and L ^B each independently represent an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom, It may have a substituent. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. The number of carbon atoms of the alkylene group represented by L ^A and L ^B is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the carbon atoms of the substituent. is there. The number of carbon atoms of the cycloalkylene group represented by L ^A and L ^B is usually 3 to 20, excluding the number of carbon atoms of the substituent.

The alkylene group represented by L ^A and L ^B, for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, and octylene group. Alkylene group represented by L ^A and L ^B may have a substituent, and examples of the substituent, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom, a cyano group are preferable. These groups may further have a substituent.

The cycloalkylene group represented by L ^A and L ^B, for example, cyclopentylene group, cyclohexylene group and the like. Cycloalkylene group represented by L ^A and L ^B may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom, a cyano Groups are preferred. These groups may further have a substituent.

Arylene group represented by L ^A and L ^B may have a substituent. The arylene group is preferably a phenylene group or a fluorenediyl group, more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group. Examples of the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, or a bridging group A. A crosslinking group selected from the group is preferred. These groups may further have a substituent.

The divalent heterocyclic group represented by L ^A and L ^B is preferably a group represented by formula (AA-1) to formula (AA-34).

L ^A and L ^B are preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group, or an alkylene group, because the production of the polymer compound of the second organic layer is facilitated. is there. These groups may have a substituent.

If the L ^A and L ^B are different, the driving voltage of the light emitting device according to this embodiment is lower, among the L ^A and L ^B, are preferably one of them is an alkylene group. Further, since the crosslinkable polymer compound of the second organic layer is more excellent, the combination of L ^A and L ^B is a combination of the two alkylene groups, combinations of the two arylene group or an alkylene group and arylene A combination of groups is preferable, and a combination of two alkylene groups or a combination of an alkylene group and an arylene group is more preferable.

X ^A and X ^B each independently represent a crosslinking group. X ^A or X ^B is preferably at least one cross-linking group selected from the cross-linking group A group, since the driving voltage of the light emitting device according to this embodiment is lower, and X ^A and X ^B are More preferably, the crosslinking group is at least one crosslinking group selected from the group A.

As the bridging group selected from the above bridging group A, since synthesis is easy, it is preferable that the formula (XL-1) to the formula (XL-4), the formula (XL-7) to the formula (XL-10). Or a bridging group represented by formula (XL-14) to formula (XL-17), more preferably formula (XL-1), formula (XL-3), formula (XL-9), formula (XL) XL-10), a crosslinking group represented by formula (XL-16) or formula (XL-17), more preferably formula (XL-1), formula (XL-16) or formula (XL-17) And particularly preferably a crosslinking group represented by the formula (XL-1) or the formula (XL-17). In the formula in the bridging group A, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, n ^XL represents an integer of 0 to 5, and * 1 represents a bonding position.

Since crosslinking of the polymer compound of the second organic layer is more excellent, it is preferable that the X ^A and X ^B differ.

Crosslinking is better than the polymer compound of the second organic layer, and, since the driving voltage of the light emitting device according to this embodiment is lower, X ^A has the formula (XL-3), formula (XL-4 ), A crosslinking group represented by formula (XL-13) or formula (XL-17), and preferably represented by formula (XL-3), formula (XL-4) or formula (XL-17). And more preferably a crosslinking group represented by the formula (XL-17). X ^B represents formula (XL-1), formula (XL-2), formula (XL-5), formula (XL-6), formula (XL-7), formula (XL-8), formula (XL) XL-14), a crosslinking group represented by formula (XL-15) or formula (XL-16) is preferred, and formula (XL-1), formula (XL-2), formula (XL-14) And more preferably a crosslinking group represented by the formula (XL-15) or the formula (XL-16), and a crosslinking group represented by the formula (XL-1) or the formula (XL-16). More preferred is a crosslinking group represented by the formula (XL-1).

The crosslinked structural unit having a group represented by the formula (XL-A) and the crosslinked structural unit having a group represented by the formula (XL-B) may be a structural unit represented by the following formula.

The crosslinked structural unit having a group represented by the formula (XL-A) is preferably a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). A structural unit represented by (XL-A1) is more preferable.

The crosslinked structural unit having a group represented by the formula (XL-B) is preferably a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). A structural unit represented by (XL-B1) is more preferable.

[Structural Units Represented by Formula (XL-A1), Formula (XL-A2), Formula (XL-B1), and Formula (XL-B2))
n ^A1 represents an integer of 1 to 4, and is preferably 1 or 2 and more preferably 2 because the driving voltage of the light emitting device according to this embodiment becomes lower.

n ^A2 represents an integer of 0 or 1, and the production of the polymer compound of the second organic layer is facilitated, and the driving voltage of the light-emitting device according to this embodiment is further reduced. is there.

Ar ^A3 represents an aromatic hydrocarbon group or a heterocyclic group, and since the driving voltage of the light emitting device according to this embodiment is lower, it is preferably an aromatic hydrocarbon group which may have a substituent. .

The number of carbon atoms of the aromatic hydrocarbon group represented by Ar ^A3 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.

The arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ^A3 is preferably a group represented by any of the formulas (A-1) to (A-20). More preferably, in the formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) A group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19). And these groups may have a substituent.

The number of carbon atoms of the heterocyclic group represented by Ar ^A3 is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, excluding the number of carbon atoms of the substituent.

The divalent heterocyclic group moiety excluding n substituents of the heterocyclic group represented by Ar ^A3 is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.

The aromatic hydrocarbon group and heterocyclic group represented by Ar ^A3 may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group. Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.

Ar ^A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded. Ar ^A5 is preferably an aromatic hydrocarbon group which may have a substituent since the driving voltage of the light emitting device according to this embodiment is further reduced.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ^A5 are the same as the definition and example of the arylene group represented by Ar ^X2 in formula (X). .

The definition and examples of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar ^A5 are the same as those of the divalent heterocyclic group part represented by Ar ^X2 in formula (X). Definitions and examples are the same.

The definition and example of a divalent group excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ^A5 and at least one heterocycle are directly bonded are represented by the formula (X) And the definition and examples of the divalent group in which at least one arylene group represented by Ar ^X2 and at least one divalent heterocyclic group are directly bonded.

n ^B1 represents an integer of 1 to 4, and is preferably 1 or 2 and more preferably 2 because the driving voltage of the light emitting device according to this embodiment becomes lower.

n ^B2 represents an integer of 0 or 1, and it is easy to produce the polymer compound of the second organic layer, and the driving voltage of the light emitting device according to this embodiment is lower, and therefore preferably 0. is there.

Ar ^B3 represents an aromatic hydrocarbon group or a heterocyclic group, and since the driving voltage of the light emitting device according to this embodiment is lower, it is preferably an aromatic hydrocarbon group which may have a substituent. .

The number of carbon atoms of the aromatic hydrocarbon group represented by Ar ^B3 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.

The arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ^B3 is preferably a group represented by any of the formulas (A-1) to (A-20). More preferably, in the formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) A group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19). And these groups may have a substituent.

The number of carbon atoms of the heterocyclic group represented by Ar ^B3 is usually 2 to 60, preferably 3 to 30, more preferably 4 to 18, excluding the number of carbon atoms of the substituent.

The divalent heterocyclic group portion excluding n substituents of the heterocyclic group represented by Ar ^B3 is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.

The aromatic hydrocarbon group and heterocyclic group represented by Ar ^B3 may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group. Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.

Ar ^B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded. Ar ^B5 is preferably an aromatic hydrocarbon group which may have a substituent since the driving voltage of the light emitting device according to this embodiment is further lowered.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ^B5 are the same as the definition and example of the arylene group represented by Ar ^X2 in formula (X). .

The definition and examples of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar ^B5 are the same as those of the divalent heterocyclic group part represented by Ar ^X2 in formula (X). Definitions and examples are the same.

The definition and example of a divalent group excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ^B5 and at least one heterocycle are directly bonded are represented by the formula (X) And the definition and examples of the divalent group in which at least one arylene group represented by Ar ^X2 and at least one divalent heterocyclic group are directly bonded.

Ar ^A4 and Ar ^A6 each independently represent an arylene group or a divalent heterocyclic group.

Ar ^B4 and Ar ^B6 each independently represent an arylene group or a divalent heterocyclic group.

The definitions and examples of the arylene groups represented by Ar ^A4 , Ar ^A6 , Ar ^B4 and Ar ^B6 are the same as the definitions and examples of the arylene groups represented by Ar ^X1 and Ar ^X3 in Formula (X).

The definition and examples of the divalent heterocyclic group represented by Ar ^A4 , Ar ^A6 , Ar ^B4 and Ar ^B6 are the definition of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in Formula (X) and Same as example.

The group represented by Ar ^A4 , Ar ^A5 , Ar ^A6 , Ar ^B4 , Ar ^B5 and Ar ^B6 may have a substituent, and ^examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, and a cycloalkoxy Group, aryl group, aryloxy group, halogen atom, monovalent heterocyclic group and cyano group are preferred.

Since the structural unit represented by the formula (XL-A1) is excellent in the stability and crosslinkability of the polymer compound in the second organic layer, the total amount of the structural units contained in the polymer compound in the second organic layer Is preferably 0.5 to 90 mol%, more preferably 3 to 70 mol%, and still more preferably 5 to 50 mol%.

Since the structural unit represented by the formula (XL-B1) is excellent in the stability and crosslinkability of the polymer compound in the second organic layer, the total amount of the structural units contained in the polymer compound in the second organic layer Is preferably 0.5 to 90 mol%, more preferably 3 to 70 mol%, and still more preferably 5 to 50 mol%.

The structural unit represented by the formula (XL-A2) has excellent stability of the polymer compound of the second organic layer and excellent crosslinkability of the polymer compound of the second organic layer. Preferably, it is 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of structural units contained in the polymer compound of the organic layer. is there.

The structural unit represented by the formula (XL-B2) has excellent stability of the polymer compound of the second organic layer and excellent crosslinkability of the polymer compound of the second organic layer. Preferably, it is 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of structural units contained in the polymer compound of the organic layer. is there.

The structural units represented by the formula (XL-A1), the formula (XL-B1), the formula (XL-A2), and the formula (XL-B2) each have 1 in the polymer compound of the second organic layer. Only the seed | species may be contained and 2 or more types may be contained.

[Preferred Embodiment of Structural Unit Represented by Formula (XL-A1), Formula (XL-A2), Formula (XL-B1), and Formula (XL-B2))
Examples of the structural units represented by the formula (XL-A1) and the formula (XL-B1) include structural units represented by the formulas (2-1) to (2-30). Examples of the structural units represented by -A2) and (XL-B2) include structural units represented by the formulas (2′-1) to (2′-9). Among these, since the crosslinkability of the polymer compound of the second organic layer is excellent, it is preferably a structural unit represented by the formula (2-1) to the formula (2-30), more preferably the formula (2). -1) to formula (2-15), formula (2-19), formula (2-20), formula (2-23), formula (2-25) or formula (2-30) More preferably a structural unit represented by formula (2-1) to formula (2-9), formula (2-20), formula (2-22) or formula (2-30).

The total amount of the structural unit having the group represented by the formula (XL-A) and the structural unit having the group represented by the formula (XL-B) contained in the polymer compound of the second organic layer is Since the polymer compound of the second organic layer is excellent in stability and crosslinkability, it is preferably 0.5 to 90 mol% with respect to the total amount of structural units contained in the polymer compound of the second organic layer. More preferably, it is 3 to 75 mol%, and still more preferably 5 to 60 mol%.

The structural unit having a group represented by the formula (XL-A) and the structural unit having a group represented by the formula (XL-B) are each only one kind in the polymer compound of the second organic layer. It may be included and two or more types may be included.

[Other structural units]
Since the polymer compound of the second organic layer has excellent hole transport properties, it is preferable that the second organic layer further includes a structural unit represented by the formula (X). Moreover, since the high molecular compound of a 2nd organic layer becomes lower in the drive voltage of the light emitting element which concerns on this embodiment, it is preferable that the structural unit represented by Formula (Y) is further included.

Since the polymer compound of the second organic layer has excellent hole transportability and the driving voltage of the light emitting device according to this embodiment is lower, the structural unit and the formula represented by the formula (X) are further reduced. It is preferable that the structural unit represented by (Y) is included.

The definitions, examples and preferred ranges of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) that may be contained in the polymer compound of the second organic layer are the above-mentioned high The definition, examples, and preferred ranges of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) that may be contained in the molecular host are the same.

In the polymer compound of the second organic layer, each of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) may be included alone or in combination of two or more. It may be.

Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 90 mol% with respect to the total amount of the structural units contained in the polymer compound of the second organic layer. More preferably, it is 1 to 70 mol%, and further preferably 10 to 50 mol%.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, is more excellent in the light emitting efficiency of the light emitting device according to this embodiment. The amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the constituent units contained.

A structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. The structural unit that is a group of the organic group is preferably excellent in charge transporting property of the polymer compound of the second organic layer, and is preferably 0. 0 relative to the total amount of the structural units contained in the polymer compound of the second organic layer. It is 5 to 40 mol%, and more preferably 3 to 30 mol%.

Examples of the polymer compound in the second organic layer include polymer compounds (P-7) to (P-37) shown in Table 2. Here, the “other structural unit” refers to the formula (XL-A1), the formula (XL-A2), the formula (XL-B1), the formula (XL-B2), the formula (X), and the formula (Y). Means a structural unit other than the structural unit represented.

In Table 2, p ′, p ″, q ′, q ″, r ′, s ′, and t ′ represent the molar ratio of each structural unit. p ′ + p ″ + q ′ + q ″ + r ′ + s ′ + t ′ = 100 and 70 ≦ p ′ + p ″ + q ′ + q ″ + r ′ + s ′ ≦ 100.

In the polymer compounds (P-7) to (P-37), the formula (XL-A1), the formula (XL-A2), the formula (XL-B1), the formula (XL-B2), the formula (X), and the formula Examples and preferred ranges of the structural unit represented by (Y) are as described above.

The polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by copolymerizing seed raw material monomers is preferable.

The number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ⁴ to 5 × 10 ⁵ , and still more preferably. 1.5 × 10 ⁴ to 1 × 10 ⁵ .

[Method for producing polymer compound of second organic layer]
The polymer compound of the second organic layer can be produced by the same method as the polymer host production method described above.

[Second composition]
The second organic layer is a group consisting of a crosslinked polymer of the second organic layer, a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a light emitting material. It may be a layer containing a composition containing at least one material selected from (hereinafter also referred to as “second composition”).

Examples and preferred ranges of the hole transport material, electron transport material, hole injection material, electron injection material and light-emitting material contained in the second composition are the hole transport material contained in the first composition, The examples and preferred ranges of the electron transport material, hole injection material, electron injection material, and light emitting material are the same.
In the second composition, the compounding amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material are each 100 parts by mass of the crosslinked polymer of the second organic layer. In general, it is 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

Examples and preferred ranges of the antioxidant contained in the second composition are the same as examples and preferred ranges of the antioxidant contained in the first composition. In the second composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the crosslinked polymer of the polymer compound of the second organic layer is 100 parts by mass.

[Second ink]
As the second ink for forming the second organic layer, a composition containing the polymer compound of the second organic layer and a solvent can be used. The second ink can be suitably used in the wet method described in the first ink section. The preferable range of the viscosity of the second ink is the same as the preferable range of the viscosity of the first ink. Examples and preferred ranges of the solvent contained in the second ink are the same as examples and preferred ranges of the solvent contained in the first ink.

In the second ink, the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the polymer compound of the second organic layer is 100 parts by mass.

<Layer structure of light emitting element>
The light emitting device according to this embodiment includes an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode. The light emitting device according to this embodiment may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.

In the light emitting device according to this embodiment, the first organic layer is usually a light emitting layer (hereinafter, also referred to as “first light emitting layer”).

In the light emitting device according to this embodiment, the second organic layer is usually a hole transport layer, a light emitting layer (hereinafter also referred to as “second light emitting layer”) or an electron transport layer, preferably a hole. It is a transport layer or a second light emitting layer, more preferably a hole transport layer.

In the light emitting device according to this embodiment, the first organic layer and the second organic layer are preferably adjacent to each other because the driving voltage of the light emitting device becomes lower. In the light emitting device according to this embodiment, the second organic layer is preferably a layer provided between the anode and the first organic layer because the driving voltage of the light emitting device is lower. More preferably, it is a hole transport layer or a second light emitting layer provided between one organic layer, and more preferably a hole transport layer provided between an anode and a first organic layer. .

In the light emitting device according to this embodiment, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the driving voltage of the light emitting device is lower, so the anode and the first It is preferable to further have a hole injection layer between the two organic layers. Further, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the gap between the cathode and the first organic layer is low. In addition, it is preferable to further include at least one of an electron injection layer and an electron transport layer.

In the light emitting device according to the present embodiment, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the driving voltage of the light emitting device is lower, It is preferable to further include at least one of a hole injection layer and a hole transport layer between the second organic layer. In addition, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the cathode and the first organic layer It is preferable to further have at least one of an electron injection layer and an electron transport layer in between.

In the light emitting device according to this embodiment, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the driving voltage of the light emitting device is lower, It is preferable to further have at least one of a hole injection layer and a hole transport layer between the first organic layer. In addition, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the cathode and the second organic layer It is preferable to further have at least one of an electron injection layer and an electron transport layer in between.

In the light emitting device according to this embodiment, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light emitting device is lower, so the anode and the first It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the organic layer. In addition, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light emitting element is lower, so that the gap between the cathode and the second organic layer is low. It is preferable to further have an electron injection layer.

Specific examples of the layer configuration of the light emitting device according to this embodiment include the layer configurations represented by the following (D1) to (D15). The light-emitting element usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.

(D1) Anode / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D2) anode / hole transporting layer (second organic layer) / first 1 light emitting layer (first organic layer) / cathode (D3) anode / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D4) Anode / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / cathode (D5) anode / hole injection layer / Second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D6) anode / hole injection layer / second light emitting layer (second Organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D7) anode / hole injection layer / hole transport layer (second organic layer) / first 1 light emitting layer (first organic layer) / cathode (D8) anode / positive Injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / cathode (D9) anode / hole injection layer / hole transport layer (second Organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D10) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (First organic layer) / electron transport layer / electron injection layer / cathode (D11) anode / hole injection layer / hole transport layer / second light emitting layer (second organic layer) / first light emitting layer (First organic layer) / electron transport layer / electron injection layer / cathode (D12) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) ) / Second light emitting layer / electron transport layer / electron injection layer / cathode (D13) anode / hole injection layer / hole transport layer / first light emitting layer (first organic layer) / second light emitting layer (Second organic layer) / Electron transport layer / Child injection layer / cathode (D14) anode / hole injection layer / hole transport layer / first light emitting layer (first organic layer) / electron transport layer (second organic layer) / electron injection layer / cathode ( D15) Anode / hole injection layer / hole transport layer (second organic layer) / second light emitting layer / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

In the above (D1) to (D15), “/” means that the layers before and after are stacked adjacent to each other. Specifically, “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” means the second light emitting layer (second organic layer) and the first light emitting layer (second organic layer). The light emitting layer (first organic layer) is adjacently laminated.

Since the driving voltage of the light emitting device according to this embodiment is lower, the layer configuration represented by (D3) to (D12) is preferable, and the layer configuration represented by (D7) to (D10) is more preferable.

In the light emitting device according to this embodiment, the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are each provided in two or more layers as necessary. It may be.

When there are a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers, and cathodes, they may be the same or different.

The thickness of the anode, hole injection layer, hole transport layer, first light emitting layer, second light emitting layer, electron transport layer, electron injection layer and cathode is usually 1 nm to 1 μm, preferably 2 nm to It is 500 nm, more preferably 5 nm to 150 nm.

In the light-emitting element according to this embodiment, the order, number, and thickness of the layers to be stacked may be adjusted in consideration of the light-emitting efficiency and element lifetime of the light-emitting element.

[Second light emitting layer]
The second light emitting layer is usually a layer containing a second organic layer or a light emitting material. When the second light emitting layer is a layer containing a light emitting material, examples of the light emitting material contained in the second light emitting layer include the light emitting material that may be contained in the first composition. It is done. The light emitting material contained in the second light emitting layer may be contained singly or in combination of two or more.

When the light-emitting element according to the present embodiment has the second light-emitting layer, and the hole transport layer and the electron transport layer to be described later are not the second organic layer, the second light-emitting layer is the second light-emitting layer. An organic layer is preferred.

[Hole transport layer]
The hole transport layer is usually a layer containing a second organic layer or a hole transport material. When the hole transport layer is a layer containing a hole transport material, examples of the hole transport material include a hole transport material that may be contained in the first composition described above. The hole transport material contained in the hole transport layer may be contained singly or in combination of two or more.

When the light-emitting element according to the present embodiment has a hole transport layer, and the above-described second light-emitting layer and an electron transport layer described later are not the second organic layer, the hole-transport layer is the second organic layer. A layer is preferred.

[Electron transport layer]
The electron transport layer is usually the second organic layer or a layer containing an electron transport material, and preferably a layer containing an electron transport material. When the electron transport layer is a layer containing an electron transport material, examples of the electron transport material contained in the electron transport layer include the electron transport material that may be contained in the first composition described above. . The electron transport material contained in the electron transport layer may be contained singly or in combination of two or more.

[Hole injection layer and electron injection layer]
The hole injection layer is a layer containing a hole injection material. As a hole injection material contained in a hole injection layer, the hole injection material which the above-mentioned 1st composition may contain is mentioned, for example. The hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.

The electron injection layer is a layer containing an electron injection material. As an electron injection material contained in an electron injection layer, the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example. The electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.

[Substrate / Electrode]
The substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed. For example, the substrate is made of a material such as glass, plastic, or silicon. When an opaque substrate is used, it is preferable that the electrode farthest from the substrate is transparent or translucent.

Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc. A composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.

Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite 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.

In the light emitting device according to this embodiment, at least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.

Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a laminating method.

[Method for Manufacturing Light-Emitting Element]
In the light emitting device according to the present embodiment, as a method for forming each layer such as the first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, the electron injection layer, etc. In the case of using, for example, a vacuum deposition method from a powder, a method by film formation from a solution or a molten state, and when using a polymer compound, for example, a method by film formation from a solution or a molten state can be mentioned.

The first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer are the first ink, the second ink, and the above-described light-emitting material and hole. It can be formed by a wet method such as a spin coating method or an ink jet printing method using inks each containing a transport material, an electron transport material, a hole injection material, and an electron injection material.

[Uses of light-emitting elements]
In order to obtain planar light emission using the light emitting element, the planar anode and the cathode may be arranged so as to overlap each other. In order to obtain pattern-like light emission, a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, a layer that is desired to be a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any one of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display device capable of displaying numbers, characters, and the like can be obtained. In order to obtain a dot matrix display device, both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter. The dot matrix display device can be driven passively or can be driven actively in combination with TFTs. These display devices can be used for displays of computers, televisions, portable terminals and the like. The planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source and display device.

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

In the Examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp). Determined by The SEC measurement conditions are as follows.
[Measurement condition]
The polymer compound to be measured was dissolved in tetrahydrofuran (THF) at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. THF was used as the mobile phase of SEC, and flowed at a flow rate of 2.0 mL / min. As the column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

In this example, the maximum peak wavelength of the emission spectrum of the compound was measured at room temperature with a spectrophotometer (trade name: FP-6500, manufactured by JASCO Corporation). A toluene solution in which the compound was dissolved in xylene at a concentration of about 0.8 × 10 ⁻⁴ mass% was used as a sample. As excitation light, UV light having a wavelength of 325 nm was used.

<Compounds HM-1 to HM-6>
Compound HM-1 was synthesized according to the method described in JP2011-174059A.
Compound HM-2 was purchased from AK Scientific.
Compound HM-3 was synthesized according to the method described in International Publication No. 2011/137922.
Compound HM-4 and Compound HM-5 were synthesized according to the methods described in JP2011-10000942 and International Publication No. 2011-137922.
Compound HM-6 was synthesized according to the method described in International Publication No. 2011/098030.

The maximum peak wavelength of the emission spectrum of Compound HM-1 was 426 nm.
The maximum peak wavelength of the emission spectrum of Compound HM-2 was 425 nm.
The maximum peak wavelength of the emission spectrum of compound HM-3 was 430 nm.
The maximum peak wavelength of the emission spectrum of Compound HM-4 was 430 nm.
The maximum peak wavelength of the emission spectrum of Compound HM-5 was 415 nm.
The maximum peak wavelength of the emission spectrum of compound HM-6 was 431 nm.

<Compounds EM-1 to EM-8, EM-10 and EM-11>
Compound EM-1 was synthesized according to the method described in JP2011-176304A.
Compound EM-2 was synthesized according to the method described in International Publication No. 2008/059713.
Compound EM-3 was synthesized according to the methods described in JP2009-290091A and JP2011-176304A.
Compound EM-4 and Compound EM-10 were purchased from Tokyo Chemical Industry Co., Ltd.
Compound EM-5 was synthesized according to the method described in JP-A-2006-176491.
Compound EM-6 was synthesized according to the method described in International Publication No. 2010/013006.
Compound EM-7 was synthesized according to the method described in International Publication No. 2005/033051.
Compound EM-8 was synthesized according to the method described in JP-A-2007-142171.
Compound EM-11 was purchased from Aldrich.

<Synthesis Example EM-9> Synthesis of Compound EM-9 Compound EM-9a (3.50 g) synthesized in accordance with the method described in International Publication No. 2009/075203 after the inside of the reaction vessel was filled with a nitrogen gas atmosphere, Compound EM-9b (9.00 g), tetrakis (triphenylphosphine) palladium (0) (0.294 g) synthesized according to the method described in JP-A-2015-110551, 20 wt% tetrabutylammonium hydroxide aqueous solution ( 18.9 g) and toluene (52 mL) were added, and the mixture was stirred at 80 ° C. for 6 hours. The resulting reaction mixture was cooled to room temperature, hexane was added, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene and washed with ion exchange water, and then the aqueous layer was removed. The obtained organic layer was filtered with a filter coated with silica gel, and the obtained filtrate was concentrated under reduced pressure. The obtained concentrate was crystallized using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure to obtain Compound EM-9 (3.5 g). Compound EM-9 had an HPLC area percentage value of 99.5% or more.

LC-MS (ESI, positive): m / z = 2043 [M] ⁺

The maximum peak wavelength of the emission spectrum of Compound EM-1 was 439 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-2 was 441 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-3 was 460 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-4 was 446 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-5 was 446 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-6 was 453 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-7 was 453 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-8 was 502 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-9 was 440 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-10 was 404 nm.
The maximum peak wavelength of the emission spectrum of Compound EM-11 was 448 nm.

<Compounds M1 to M8>
Compound M1 was synthesized according to the method described in JP2011-174062.
Compound M2 was synthesized according to the method described in JP-A-2008-106241.
Compound M3 was synthesized according to the method described in International Publication No. 2015/145871.
Compound M4 was synthesized according to the method described in International Publication No. 2013/146806.
Compound M5 was synthesized according to the method described in WO2005 / 049546.
Compound M6 was synthesized according to the method described in JP 2010-215886 A.
Compound M7 was synthesized according to the method described in International Publication No. 2013/146806.
Compound M8 was synthesized according to the method described in JP 2010-189630 A.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 Polymer compound HTL-1 was synthesized according to the method described in JP 2013-47315 A using compound M1, compound M5 and compound M2. The polymer compound HTL-1 had an Mn of 5.6 × 10 ⁴ and an Mw of 2.4 × 10 ⁵ .

The theoretical value obtained from the amount of the raw material used for polymer compound HTL-1 is that the structural unit derived from compound M1, the structural unit derived from compound M5, and the structural unit derived from compound M2 are: It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

<Synthesis Example HTL2> Synthesis of Polymer Compound HTL-2 Polymer compound HTL-2 was synthesized according to the method described in International Publication No. 2015/194448 using Compound M5 and Compound M8.

The polymer compound HTL-2 had an Mn of 4.5 × 10 ⁴ and an Mw of 1.5 × 10 ⁵ .

The high molecular compound HTL-2 has a theoretical value obtained from the amount of the charged raw materials, wherein the structural unit derived from the compound M5 and the structural unit derived from the compound M8 are formed in a molar ratio of 50:50. It is a copolymer.

<Synthesis Example HTL3> Synthesis of Polymer Compound HTL-3 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound M1 (1.09 g), Compound M5 (0.917 g), Compound M2 (0. 0669 g), Compound M6 (0.0578 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) and toluene (35 mL) were added, and the mixture was heated to 105 ° C.
(Step 2) A 20% by mass aqueous tetraethylammonium hydroxide solution (22 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours.
(Step 3) After the reaction, phenylboronic acid (61 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) were added thereto and refluxed for 18 hours.
(Step 4) After cooling the reaction solution, it was washed twice with water, twice with a 3% by mass acetic acid aqueous solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.31 g of a polymer compound HTL-3.

The polymer compound HTL-3 had an Mn of 4.6 × 10 ⁴ and an Mw of 1.5 × 10 ⁵ .

The high molecular compound HTL-3 has a structural value derived from the compound M1, a structural unit derived from the compound M5, a structural unit derived from the compound M2, and the The structural unit derived from M6 is a copolymer composed of a molar ratio of 50: 40: 5: 5.

<Synthesis Example HTL4> Synthesis of Polymer Compound HTL-4 Polymer compound HTL-4 was synthesized using Compound M3, Compound M4 and Compound M5 according to the method described in International Publication No. 2015/145871.

The polymer compound HTL-4 had an Mn of 2.3 × 10 ⁴ and an Mw of 1.2 × 10 ⁵ .

The theoretical value obtained from the amount of the raw material used for polymer compound HTL-4 is that the structural unit derived from compound M3, the structural unit derived from compound M4, and the structural unit derived from compound M5 are: It is a copolymer formed by a molar ratio of 45: 5: 50.

<Synthesis Example HTL5> Synthesis of Polymer Compound HTL-5 Polymer Compound HTL-5 was synthesized using Compound M8, Compound M7, Compound M2 and Compound M6 according to the method described in International Publication No. 2013/146806. .

The polymer compound HTL-5 had an Mn of 4.3 × 10 ⁴ and an Mw of 3.6 × 10 ⁵ .

The polymer compound HTL-5 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M8, a structural unit derived from the compound M7, a structural unit derived from the compound M2, and a compound. The structural unit derived from M6 is a copolymer composed of a molar ratio of 50: 40: 5: 5.

<Example D1> Fabrication and evaluation of light-emitting element D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. On the anode, a hole injection material ND-3202 (manufactured by Nissan Chemical Industries) was formed into a film with a thickness of 35 nm by spin coating. In an air atmosphere, the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.

(Formation of second organic layer)
The polymer compound HTL-4 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. An organic layer of was formed. By this heating, the polymer compound HTL-4 became a crosslinked product.

(Formation of first organic layer)
Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91.5 mass% / 8.5 mass%) were dissolved in toluene at a concentration of 2 mass%. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the second organic layer by spin coating, and heated on a hot plate at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. 1 organic layer was formed.

(Formation of cathode)
The substrate on which the first organic layer is formed is depressurized to 1 × 10 ⁻⁴ Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the first organic layer, and then fluorinated. About 80 nm of aluminum was deposited on the sodium layer. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D1. The drive voltage at 400 cd / m ² was 5.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Example D2> Production and evaluation of light-emitting device D2 A light-emitting device D2 was produced in the same manner as in Example D1, except that Compound EM-1 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D2. The driving voltage at 400 cd / m ² was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D3> Production and evaluation of light-emitting device D3 A light-emitting device D3 was produced in the same manner as in Example D1, except that Compound EM-3 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D3. The driving voltage at 400 cd / m ² was 6.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D4> Production and evaluation of light-emitting device D4 A light-emitting device D4 was produced in the same manner as in Example D1, except that Compound EM-4 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D4. The driving voltage at 400 cd / m ² was 6.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D5> Production and evaluation of light-emitting device D5 A light-emitting device D5 was produced in the same manner as in Example D1, except that Compound EM-5 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D5. The driving voltage at 400 cd / m ² was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Example D6> Production and evaluation of light-emitting device D6 A light-emitting device D6 was produced in the same manner as in Example D1, except that Compound EM-6 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D6. The driving voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.18).

<Example D7> Production and evaluation of light-emitting device D7 A light-emitting device D7 was produced in the same manner as in Example D1, except that Compound EM-7 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D7. The driving voltage at 400 cd / m ² was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.24).

<Example D8> Production and evaluation of light-emitting device D8 A light-emitting device D8 was produced in the same manner as in Example D1, except that Compound EM-8 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D8. The driving voltage at 400 cd / m ² was 5.5 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.50).

<Example D9> Production and evaluation of light-emitting device D9 A light-emitting device D9 was produced in the same manner as in Example D1, except that compound HM-3 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D9. The driving voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).

<Example D10> Production and evaluation of light-emitting device D10 A light-emitting device D10 was produced in the same manner as in Example D1, except that compound HM-4 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D10. The drive voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D11> Production and evaluation of light-emitting device D11 A light-emitting device D11 was produced in the same manner as in Example D1, except that compound HM-5 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D11. The driving voltage at 400 cd / m ² was 5.2 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D12> Production and evaluation of light-emitting device D12 A light-emitting device D12 was produced in the same manner as in Example D1, except that Compound EM-9 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D12. The drive voltage at 400 cd / m ² was 5.3 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D13> Production and evaluation of light-emitting device D13 A light-emitting device D13 was produced in the same manner as in Example D1, except that Compound HM-6 was used instead of Compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D13. The driving voltage at 400 cd / m ² was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.18).

<Example D14> Production and evaluation of light-emitting device D14 A light-emitting device D14 was produced in the same manner as in Example D13, except that Compound EM-8 was used instead of Compound EM-2 in Example D13.

EL light emission was observed by applying a voltage to the light emitting element D14. The driving voltage at 400 cd / m ² was 6.6 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.46).

<Example D15> Production and evaluation of light-emitting device D15 Light-emitting device D15 was prepared in the same manner as in Example D1, except that polymer compound HTL-5 was used instead of polymer compound HTL-4 in Example D1. Was made.

EL light emission was observed by applying a voltage to the light emitting element D15. The drive voltage at 400 cd / m ² was 4.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D16> Fabrication and evaluation of light-emitting device D16 Light-emitting device D16 was prepared in the same manner as in Example D1, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D1. Was made.

EL light emission was observed by applying a voltage to the light emitting element D16. The driving voltage at 400 cd / m ² was 5.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.22).

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 Light-emitting element CD1 was prepared in the same manner as Example D1, except that polymer compound HTL-2 was used instead of polymer compound HTL-4 in Example D1. Was made.

EL light emission was observed by applying a voltage to the light emitting device CD1. The drive voltage at 400 cd / m ² was 7.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

Table 3 shows the results of Examples and Comparative Examples.

Example D17 Fabrication and Evaluation of Light-Emitting Element D17 “Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. In the formation of the first organic layer) of Example D1. “Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5 wt% / 8.5 wt%)” instead of “5 wt% / 8.5 wt%)” In addition, light emission was performed in the same manner as in Example D1, except that the polymer compound HTL-3 was used instead of the polymer compound HTL-4 in (Formation of second organic layer) in Example D1. Element D17 was produced.

EL light emission was observed by applying a voltage to the light emitting element D17. The driving voltage at 100 cd / m ² was 10.0V.

Example D18 Fabrication and Evaluation of Light-Emitting Element D18 “Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. In the formation of the first organic layer) of Example D1. “Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5 wt% / 8.5 wt%)” instead of “5 wt% / 8.5 wt%)” A light emitting device D18 was produced in the same manner as in Example D1 except that it was used.

EL light emission was observed by applying a voltage to the light emitting element D18. The driving voltage at 100 cd / m ² was 9.2V.

<Comparative Example CD2> Production and Evaluation of Light-Emitting Element CD2 “Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. In the formation of the first organic layer) of Example D1. “Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5 wt% / 8.5 wt%)” instead of “5 wt% / 8.5 wt%)” Further, light emission was conducted in the same manner as in Example D1, except that the polymer compound HTL-1 was used instead of the polymer compound HTL-4 in (Formation of second organic layer) in Example D1. Element CD2 was produced.

EL light emission was observed by applying a voltage to the light emitting device CD2. The driving voltage at 100 cd / m ² was 11.7V.

Table 4 shows the results of Examples and Comparative Examples.

<Example D19> Production and evaluation of light-emitting device D19 A light-emitting device D19 was produced in the same manner as in Example D16.

EL light emission was observed by applying a voltage to the light emitting element D19. The driving voltage at 100 cd / m ² was 4.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Comparative Example CD3> Fabrication and Evaluation of Light-Emitting Element CD3 Implementation was performed except that polymer compound HTL-1 was used instead of polymer compound HTL-3 in (Formation of second organic layer) in Example D19. A light emitting device CD3 was produced in the same manner as in Example D19.

EL light emission was observed by applying a voltage to the light emitting device CD3. The driving voltage at 100 cd / m ² was 6.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

Table 5 shows the results of Examples and Comparative Examples.

<Example D20> Fabrication and evaluation of light-emitting element D20 A light-emitting element D20 was fabricated in the same manner as in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D20. The drive voltage at 5000 cd / m ² was 9.1 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D21> Fabrication and evaluation of light-emitting element D21 A light-emitting element D21 was fabricated in the same manner as in Example D2.

EL light emission was observed by applying a voltage to the light emitting element D21. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D22> Production and evaluation of light-emitting element D22 A light-emitting element D22 was produced in the same manner as in Example D12.

EL light emission was observed by applying a voltage to the light emitting element D22. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D23> Production and evaluation of light-emitting element D23 A light-emitting element D23 was produced in the same manner as in Example D5.

EL light emission was observed by applying a voltage to the light emitting element D23. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D24> Production and evaluation of light-emitting element D24 A light-emitting element D24 was produced in the same manner as in Example D8.

EL light emission was observed by applying a voltage to the light emitting element D24. The drive voltage at 5000 cd / m ² was 8.8 V, and the CIE chromaticity coordinates (x, y) were (0.24, 0.49).

<Example D25> Production and evaluation of light-emitting device D25 A light-emitting device D25 was produced in the same manner as in Example D1, except that Compound EM-10 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D25. The drive voltage at 5000 cd / m ² was 11.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Comparative Example CD4> Fabrication and Evaluation of Light-Emitting Element CD4 Light-emitting element CD4 was prepared in the same manner as Example D25, except that polymer compound HTL-2 was used instead of polymer compound HTL-4 in Example D25. Was made.

EL light emission was observed by applying a voltage to the light emitting device CD4. The drive voltage at 5000 cd / m ² was 11.7 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.23).

<Comparative Example CD5> Production and Evaluation of Light-Emitting Element CD5 A light-emitting element CD5 was produced in the same manner as Comparative Example CD1.

EL light emission was observed by applying a voltage to the light emitting device CD5. Although voltage was applied to 12V, it did not reach 5000 cd / m ² .

Table 6 shows the results of Examples and Comparative Examples.

<Example D26> Production and evaluation of light-emitting element D26 A light-emitting element D26 was produced in the same manner as in Example D6.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D26. The drive voltage at 7500 cd / m ² was 11.2 V, and the CIE chromaticity coordinates (x, y) were (0.14, 0.17).

<Example D27> Production and evaluation of light-emitting device D27 A light-emitting device D27 was produced in the same manner as in Example D1, except that Compound EM-11 was used instead of Compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D27. The drive voltage at 7500 cd / m ^{2 was} 11.8 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.18).

Claims

A light-emitting element having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer containing a light emitting material represented by the formula (B),
The maximum peak wavelength of the emission spectrum of the luminescent material represented by the formula (B) is 380 nm or more and 750 nm or less,
The second organic layer contains a crosslinked product of a polymer compound containing a structural unit having a group represented by the formula (XL-A) and a structural unit having a group represented by the formula (XL-B) Layer to
A light-emitting element in which the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different from each other.

[Where:
n 1B represents an integer of 0 to 15.
Ar 1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
R 1B is a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group or cycloalkynyl. Represents a group, and these groups may have a substituent. When there are a plurality of R 1B s , they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

[Where:
nA and nB each independently represents an integer of 0 to 5.
L A and L B each independently represent an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom, It may have a substituent. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of L A and L B , they may be the same or different from each other.
X A and X B each independently represent a crosslinking group. ]
2. The light emitting device according to claim 1, wherein X A or X B is at least one crosslinking group selected from the crosslinking group A group.

[Wherein R XL represents a methylene group, an oxygen atom or a sulfur atom, and n XL represents an integer of 0 to 5. When a plurality of R XL are present, they may be the same or different, and when a plurality of n XL are present, they may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ]
The crosslinked structural unit having a group represented by the formula (XL-A) is a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). Or the light emitting element of 2.

[Where:
n A1 represents an integer of 1 to 4. When a plurality of n A1 are present, they may be the same or different.
n A2 represents an integer of 0 or 1.
XLA represents a bridging group represented by the formula (XL-A), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. When a plurality of XLA are present, they may be the same or different. However, at least one XLA is a crosslinking group represented by the formula (XL-A).
Ar A3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar A4 and Ar A6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar A4 , Ar A5 and Ar A6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be. ]
The crosslinked structural unit having a group represented by the formula (XL-B) is a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). Or the light emitting element of 2.

[Where:
n B1 represents an integer of 1 to 4. When a plurality of n B1 are present, they may be the same or different.
n B2 represents an integer of 0 or 1.
X LB represents a bridging group represented by the above formula (XL-B), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. When a plurality of X LB are present, they may be the same or different. However, at least one X LB is a bridging group represented by the formula (XL-B).
Ar B3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar B4 and Ar B6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar B4 , Ar B5, and Ar B6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be. ]
Wherein X A is the formula selected from the bridging group A (XL-3), formula (XL-4), a bridging group of the formula (XL-13) or formula (XL-17), wherein Item 5. The light emitting device according to any one of Items 2 to 4.
X B is selected from Formula (XL-1), Formula (XL-2), Formula (XL-5), Formula (XL-6), Formula (XL-7), Formula (X) selected from Group A The light emitting device according to any one of claims 2 to 5, which is a crosslinking group represented by XL-8), formula (XL-14), formula (XL-15), or formula (XL-16).
The light emitting device according to any one of claims 1 to 6, wherein Ar 1B is an aromatic hydrocarbon group.
Ar 1B is a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, indene ring, The light emitting device according to claim 7, wherein the light emitting device is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring.
The Ar 1B is formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a biphenyl ring, a fluorene ring, a pyrene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring. The light emitting device according to claim 8, which is a group.
The light emitting device according to any one of claims 1 to 9, wherein the n 1B is an integer of 1 to 8.
The R 1B is an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, or a cycloalkenyl group (these groups may have a substituent), according to any one of claims 1 to 10. The light emitting element of description.
The first organic layer is a layer containing a light emitting material represented by the formula (B) and a host material,
The light-emitting element according to any one of claims 1 to 11, wherein the host material is a compound represented by the formula (FH-1) or a polymer compound including a structural unit represented by the formula (Y).

[Where:
Ar H1 and Ar H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups optionally have a substituent.
n H1 represents an integer of 0 to 15.
L H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R H11 ) 2 ] n H11 —, and these groups optionally have a substituent. When a plurality of L H1 are present, they may be the same or different. n H11 represents an integer of 1 to 10. R H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

[In the formula, Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ]
The light emitting device according to any one of claims 1 to 12, wherein a maximum peak wavelength of an emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 570 nm or less.
The light-emitting element according to any one of claims 1 to 13, wherein the first organic layer and the second organic layer are adjacent to each other.
The light-emitting element according to any one of claims 1 to 14, wherein the second organic layer is a layer provided between the anode and the first organic layer.