Composition
A composition with defined compounds and solvents stabilizes inkjet printing for organic electroluminescent devices, resolving viscosity and purification challenges in forming organic layers.
Patent Information
- Application Number
- JP2024115590
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-07-19
- Publication Date
- 2026-01-29
AI Technical Summary
The challenge in forming organic layers for organic electroluminescent devices using polymer compounds is that low molecular weight compounds result in low viscosity compositions unsuitable for inkjet printing, while high molecular weight compounds complicate purification and require advanced reaction control.
A composition comprising specific phosphorescent and low molecular weight compounds, polymer compounds with defined structural units, and solvents with certain properties, enabling stable application by inkjet printing.
The composition allows for stable application by inkjet printing, addressing the viscosity and purification issues of polymer compounds in organic electroluminescent devices.
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Abstract
Description
[Technical Field]
[0001] The present disclosure relates to compositions. [Background technology]
[0002] Organic electroluminescent devices (hereinafter also referred to as "light-emitting devices") have high luminous efficiency and low driving voltage, making them suitable for use in displays, and research and development into these devices is currently underway. These light-emitting devices include organic layers such as a light-emitting layer and a charge transport layer. While low-molecular-weight compounds and polymeric compounds can be used to form the organic layers, polymeric compounds can be used to form the organic layers by coating methods such as inkjet printing, and polymeric compounds are therefore being investigated for use in the manufacture of light-emitting devices.
[0003] However, when a polymer compound is used to form the organic layer, if the molecular weight of the polymer compound is too small, the viscosity of the composition becomes low, and the composition cannot be stably applied by inkjet printing.
[0004] On the other hand, when trying to increase the molecular weight of a polymer compound, the viscosity of the reaction solution during the polymerization reaction increases significantly, making it difficult to sufficiently remove impurities that degrade the characteristics of light-emitting devices during the purification process. Furthermore, in order to stably produce polymer compounds with high molecular weights, advanced control of the polymerization reaction is required, and it has been technically difficult to increase the molecular weight of all polymer compounds used in light-emitting devices. [Prior art documents] [Patent documents]
[0005] [Patent Document 1] International Publication No. 00 / 59267 Summary of the Invention [Problem to be solved by the invention]
[0006] The present disclosure is intended to solve the above-mentioned conventional problems, and an object of the present disclosure is to provide a composition that can be stably applied by inkjet printing. [Means for solving the problem]
[0007] The present disclosure provides the following [1] to [7].
[0008] [1] At least one compound selected from the group consisting of a phosphorescent compound and a low molecular weight compound (B), Polymer compound 1, Polymer compound 2, A solvent; A composition comprising: The low molecular weight compound (B) contains a boron atom, an oxygen atom, a sulfur atom, a selenium atom, sp 3 a low molecular weight compound having a fused heterocyclic skeleton (b) containing at least one atom selected from the group consisting of a carbon atom and a nitrogen atom in the ring; The polymer compound 1 includes at least one of a structural unit represented by formula (X), a structural unit represented by formula (Y), a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B), and a structural unit having a group obtained by removing one or more hydrogen atoms from the phosphorescent compound, and has a weight-average molecular weight in terms of polystyrene of 2.0 × 10 5 The polymer compound is as described above. The polymer compound 2 includes at least one of a structural unit represented by formula (X), a structural unit represented by formula (Y), a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B), and a structural unit having a group obtained by removing one or more hydrogen atoms from the phosphorescent compound, and has a weight-average molecular weight in terms of polystyrene of 2.0 × 10 5 a polymer compound having a molecular weight of less than The composition, wherein the solvent satisfies at least one of requirements (i) and (ii). (i) The boiling point is 200°C or higher. (ii) has a cycloalkyl group; [ka] [In the formula, a X1 and a X2 each independently represents an integer of 0 or greater. Ar X1 and Ar X3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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. Ar X2 and Ar X4 are each independently 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 groups may have a substituent. When a plurality of such substituents are present, 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. Ar X2 When a plurality of Ar are present, they may be the same or different. X4 When there are a plurality of groups, they may be the same or different. R X1 , R X2 and R X3 R each independently 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. When a plurality of such substituents are present, 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. X2 When there are multiple R's, they may be the same or different. X3 When there are multiple, they may be the same or different. [ka] [In the formula, Ar Y1represents 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 groups may have a substituent. When a plurality of such substituents are present, 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. ] [2] The composition according to [1], wherein the polymer compound 1 consists solely of a constitutional unit represented by formula (Y). [3] The composition according to [1] or [2], wherein the polymer compound 1 consists solely of constitutional units represented by formula (Y-1) or formula (Y-2). [ka] [In the formula, R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, 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. When there are multiple R Y1 may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. X Y1 is -C(R Y2 )2-, -C(R Y2 )=C(R Y2 )- or -C(R Y2 )2-C(R Y2 )2- represents a group represented by R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, 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. When there are multiple R Y2may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. [4] The composition according to any one of [1] to [3], wherein the polymer compound 2 contains a constitutional unit represented by formula (Z). [ka] [In the formula, Ar Z represents a divalent heterocyclic group having a group represented by -N= within the ring, and the group may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar Z1 and Ar Z2 are each independently an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar Z1 When a plurality of Ar are present, they may be the same or different. Z2 When there are multiple groups, they may be the same or different. n Z1 and n Z2 each independently represents an integer of 0 or more and 5 or less. [5] The composition according to any one of [1] to [4], wherein the phosphorescent compound is represented by formula (M): [ka] [In the formula, M 1 represents an iridium atom or a platinum atom. n M1 represents an integer of 1 or greater, and n M2 represents an integer of 0 or more. However, M 1 If is an iridium atom, n M1 +n M2 is 3 and M 1 If is a platinum atom, n M1 +n M2is 2. E 1 and E 2 each independently represents a carbon atom or a nitrogen atom. 1 and E 2 At least one of the groups is a carbon atom. Ring R M1 represents an aromatic heterocycle, and this ring may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R M1 When there are multiple groups, they may be the same or different. Ring R M2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R M2 When there are multiple groups, they may be the same or different. Ring R M1 and the substituents that may be present on the ring R M2 The substituents which may be possessed by the group may be bonded to each other to form a ring together with the atoms to which they are bonded. -A D1 ---A D2 - represents an anionic bidentate ligand. D1 and A D2 are each independently, M 1 represents a carbon atom, an oxygen atom, or a nitrogen atom bonded to the atom, and these atoms may be atoms constituting a ring. D1 ---A D2 When there are multiple -s, they may be the same or different. [6] The composition according to any one of [1] to [5], further comprising at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (excluding those corresponding to the phosphorescent compound), and an antioxidant. [7] A light-emitting device comprising the composition according to any one of [1] to [6]. [Effects of the Invention]
[0009] According to the present disclosure, a composition is provided that can be stably applied by inkjet printing. DETAILED DESCRIPTION OF THE INVENTION
[0010] Preferred embodiments of the present disclosure will be described in detail below.
[0011] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified.
[0012] "Room temperature" means 25°C. 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 proton atom. In the formula representing a metal complex, the solid line representing a bond to a central metal means an ionic bond, a covalent bond, or a coordinate bond.
[0013] "Low molecular weight compounds" are compounds that do not have a molecular weight distribution and have a molecular weight of 1 x 10 4 The following compounds are meant: "Polymer compounds" are compounds that have a molecular weight distribution and have a number average molecular weight of 1 x 10 in terms of polystyrene. 3 or more (e.g., 1×10 3 ~1×10 8 ) means a polymer in which The term "structural unit" refers to a unit that exists in one or more instances in a polymer compound. A structural unit that exists in two or more instances in a polymer compound is generally also called a "repeating unit." The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms. The terminal group of the polymer compound is preferably a stable group from the viewpoint of the light-emitting properties of the light-emitting device. The terminal group of the polymer compound is preferably a group that is conjugated to the main chain of the polymer compound, and examples thereof include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond.
[0014] The "alkyl group" may be either linear or branched. The number of carbon atoms in a linear alkyl group, not including the number of carbon atoms in the substituent, is usually 1 to 50, preferably 1 to 20, and more preferably 1 to 10. The number of carbon atoms in a branched alkyl group, not including the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 20, and more preferably 4 to 10. The alkyl group may have a substituent. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, a 2-ethylbutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group, a dodecyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a substituent (for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3-(4-methylphenyl)propyl group, a 3-(3,5-di-hexylphenyl)propyl group, and a 6-ethyloxyhexyl group).
[0015] The number of carbon atoms in the "cycloalkyl group" is usually 3 to 50, preferably 3 to 20, and more preferably 4 to 10, not including the number of carbon atoms in the substituent. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group and groups in which some or all of the hydrogen atoms in the cyclohexyl group have been substituted with substituents.
[0016] The number of carbon atoms in the "alkylene group" is usually 1 to 20, preferably 1 to 15, and more preferably 1 to 10, not including the number of carbon atoms in the substituent. The alkylene group may have a substituent. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, an octylene group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
[0017] The number of carbon atoms in the "cycloalkylene group" is usually 3 to 20, preferably 4 to 10, and more preferably 5 to 7, not including the number of carbon atoms in the substituent. The cycloalkylene group may have a substituent. Examples of the cycloalkylene group include a cyclohexylene group and a cycloalkylene group in which some or all of the hydrogen atoms are substituted with a substituent. Examples of such groups include:
[0018] An "aromatic hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom that constitutes a ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to a carbon atom that constitutes a ring from an aromatic hydrocarbon is also called an "aryl group." A group obtained by removing two hydrogen atoms directly bonded to a carbon atom that constitutes a ring from an aromatic hydrocarbon is also called an "arylene group." The number of carbon atoms in the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20, not including the number of carbon atoms in the substituent.
[0019] Examples of the "aromatic hydrocarbon group" include groups in which one or more hydrogen atoms directly bonded to a carbon atom constituting the ring have been removed from a monocyclic aromatic hydrocarbon (such as benzene) or a polycyclic aromatic hydrocarbon (such as bicyclic aromatic hydrocarbons such as naphthalene, indene, naphthoquinone, indenone, and tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthoquinone, and fluorenone; tetracyclic aromatic hydrocarbons such as benzanthracene, benzophenanthrene, and benzofluorene; pentacyclic aromatic hydrocarbons such as dibenzanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene; and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene). The aromatic hydrocarbon group may be a group in which a plurality of groups are bonded to a monocyclic aromatic hydrocarbon or a polycyclic aromatic hydrocarbon, in which one or more hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed. The aromatic hydrocarbon group may have a substituent.
[0020] The arylene group may have a substituent, and examples thereof include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and groups in which these groups have a substituent, and preferred are groups represented by formulas (A-1) to (A-20). The arylene group includes groups in which a plurality of these groups are bonded.
[0021] [ka]
[0022] [ka]
[0023] [ka]
[0024] [ka]
[0025] [In the formula, R and R a each independently represents a hydrogen atom, an alkyl group, or an aryl group. Multiple R and R a may be the same or different. a may be bonded to each other to form a ring together with the carbon atoms to which they are attached.
[0026] The "alkoxy group" may be either linear or branched. The number of carbon atoms in a linear alkoxy group, not including the number of carbon atoms in the substituent, is usually 1 to 40, preferably 1 to 20, and more preferably 1 to 10. The number of carbon atoms in a branched alkoxy group, not including the number of carbon atoms in the substituent, is usually 3 to 40, preferably 3 to 20, and more preferably 4 to 10. The alkoxy group may have a substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropyloxy group, a butyloxy group, a hexyloxy group, a 2-ethylhexyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents. The number of carbon atoms in the "cycloalkoxy group" is usually 3 to 40, preferably 3 to 20, and more preferably 4 to 10, not including the number of carbon atoms in the substituents. The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group and groups in which some or all of the hydrogen atoms in the cycloalkoxy group have been substituted with substituents. The number of carbon atoms in the "aryloxy group" is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20, not including the number of carbon atoms in the substituent. The aryloxy group may have a substituent. Examples of the aryloxy group include a phenoxy group, a naphthyloxy group, an anthracenyloxy group, a pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
[0027] A "heterocyclic group" refers to a group obtained by removing, from a heterocycle, one or more hydrogen atoms directly bonded to atoms constituting the ring (carbon atoms or heteroatoms). Among heterocyclic groups, an "aromatic heterocyclic group", which is a group obtained by removing, from an aromatic heterocycle, one or more hydrogen atoms directly bonded to atoms constituting the ring, is preferred. A group obtained by removing, from a heterocycle, p hydrogen atoms (p represents an integer of 1 or more) directly bonded to atoms constituting the ring is also called a "p-valent heterocyclic group". A group obtained by removing, from an aromatic heterocycle, p hydrogen atoms directly bonded to atoms constituting the ring is also called a "p-valent aromatic heterocyclic group".
[0028] Examples of the "aromatic heterocycle" include heterocycles that themselves exhibit aromaticity, such as azole, thiophene, furan, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, and carbazole, as well as heterocycles that do not themselves exhibit aromaticity but are condensed with an aromatic ring, such as phenoxazine, phenothiazine, and benzopyran.
[0029] The number of carbon atoms in the heterocyclic group, not including the number of carbon atoms in the substituent, is usually 1 to 60, preferably 2 to 40, and more preferably 3 to 20. The number of heteroatoms in the heterocyclic group, not including the number of heteroatoms in the substituent, is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
[0030] Examples of the heterocyclic group include monocyclic heterocycles (e.g., furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, tetrazole, pyridine, diazabenzene, and triazine), and polycyclic heterocycles (e.g., bicyclic heterocycles such as azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, benzothiophene dioxide, benzothiophene oxide, and benzopyranone; dibenzofuran, dibenzothiophene, dibenzothiophene dioxide, dibenzothiophene oxide, dibenzopyranone, dibenzoborole, dibenzosilole, dibenzophosphole, dibenzoselenophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydro Tricyclic heterocycles such as phenazine, acridone, phenazaborine, phenophosphazine, phenoselenazine, phenazasiline, azaanthracene, diazaanthracene, azaphenanthrene, and diazaphenanthrene; tetracyclic heterocycles such as hexaazatriphenylene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, and benzonaphthothiophene; dibenzocarbazole, indolocarbazole, indenocarbazole, Examples of heterocyclic groups include 5-ring heterocycles such as carbazolocarbazole, azaindolocarbazole, diazaindenocarbazole, and diazaindenocarbazole; 6-ring heterocycles such as carbazolocarbazole, benzoindolocarbazole, and benzoindenocarbazole; and 7-ring heterocycles such as dibenzoindolocarbazole and dibenzoindenocarbazole. Examples of heterocyclic groups include groups obtained by removing one or more hydrogen atoms directly bonded to atoms constituting the ring from the heterocyclic group. The heterocyclic group may be a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting the ring from a monocyclic heterocycle or a polycyclic heterocycle, and bonding the multiple groups. The heterocyclic group may have a substituent.
[0031] The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34), and includes groups in which a plurality of these groups are bonded.
[0032] [ka]
[0033] [ka]
[0034] [ka]
[0035] [ka]
[0036] [ka]
[0037] [ka]
[0038] [ka]
[0039] [Wherein R and R a has the same meaning as above.]
[0040] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0041] The "amino group" may have a substituent, and is preferably a substituted amino group (i.e., a secondary amino group or a tertiary amino group, more preferably a tertiary amino group). The substituent that the amino group has is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. When the amino group has multiple substituents, they may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded.
[0042] Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, a diarylamino group, and groups in which some or all of the hydrogen atoms in these groups have been further substituted with substituents. Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis(methylphenyl)amino group, a bis(3,5-di-tert-butylphenyl)amino group, and groups in which some or all of the hydrogen atoms in these groups have been further substituted with substituents.
[0043] The "alkenyl group" may be either straight-chain or branched. The number of carbon atoms in a straight-chain alkenyl group, not including the number of carbon atoms in substituents, is usually 2 to 30, preferably 3 to 20, and more preferably 3 to 10. The number of carbon atoms in a branched alkenyl group, not including the number of carbon atoms in substituents, is usually 3 to 30, preferably 4 to 20, and more preferably 4 to 10.
[0044] The number of carbon atoms in the "cycloalkenyl group" is usually 3 to 30, preferably 4 to 20, and more preferably 5 to 10, not including the number of carbon atoms in substituents. The alkenyl group and the cycloalkenyl group may have a substituent. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a substituent. Examples of the cycloalkenyl group include a cyclohexenyl group, a cyclohexadiene group, and a cyclohexadiene group. Examples of the aryl group include a norbornylenyl group, a cyclooctatrienyl group, a norbornylenyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
[0045] The "alkynyl group" may be either linear or branched. The number of carbon atoms in the alkynyl group, not including the carbon atoms of the substituents, is usually 2 to 30, and preferably 3 to 10. The number of carbon atoms in a branched alkynyl group, not including the carbon atoms of the substituents, is usually 4 to 30, and preferably 4 to 10.
[0046] The number of carbon atoms in the "cycloalkynyl group" is usually 4 to 30, and preferably 4 to 10, not including the carbon atoms of the substituents.
[0047] The alkynyl group and the cycloalkynyl group may have a substituent. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a substituent. Examples of the cycloalkynyl group include a cyclooctynyl group and groups in which some or all of the hydrogen atoms in these groups have been substituted with a substituent.
[0048] The "crosslinking group" is a group that can generate a new bond by heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. The crosslinking group is preferably at least one crosslinking group selected from Group A of crosslinking groups (i.e., at least one group selected from the groups represented by Formulae (XL-1) to (XL-19)).
[0049] [ka]
[0050] [In the formula, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n XL represents an integer from 0 to 5. XL When there are multiple n, they may be the same or different. XL When there are a plurality of groups, they may be the same or different. *1 indicates the bonding position. These bridging groups may have a substituent, and when there are a plurality of such substituents, 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.]
[0051] Examples of the "substituent" include a halogen atom, a cyano group, an alkyl group, and a cycloalkyl group. Examples of the substituent include a group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, and a cycloalkynyl group. The substituent may be a bridging group. When multiple substituents are present, they may be the same or different. When multiple substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded, but it is preferable that they do not form a ring.
[0052] Examples of the "divalent group" include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R 0 )-, -B(R 0 )-, a group represented by -P(R 0)-, a group represented by -(O=)P(R 0 )-, a group represented by -O-, a group represented by -S-, a group represented by -Se-, a group represented by -S(=O)-, a group represented by -S(=O)2-, and a group represented by -C(=O)-. The divalent group may be a group in which a plurality of these groups are bonded. The divalent group may have a substituent. When a plurality of the substituents are present, 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. R 0 represents a hydrogen atom or a substituent. R 0 Examples of the substituent include a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, and a cyano group, and are preferably 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 the substituents are present, 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.
[0053] (Phosphorescent compounds) The term "phosphorescent compound" generally refers to a compound that exhibits phosphorescence at room temperature, and is preferably a metal complex that exhibits luminescence from a triplet excited state at room temperature. This metal complex that exhibits luminescence from a triplet excited state has a central metal atom and a ligand.
[0054] Examples of the central metal atom include an atom with an atomic number of 40 or more, which has spin-orbit interaction in the complex and can cause intersystem crossing between the singlet state and the triplet state. Examples of the metal atom include a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, and a platinum atom. An iridium atom or a platinum atom is preferred because the light-emitting element using the composition of this embodiment has an excellent luminance life.
[0055] Examples of the ligand include a neutral or anionic monodentate ligand, or a neutral or anionic polydentate ligand, which forms at least one bond selected from the group consisting of a coordinate bond and a covalent bond with the central metal atom. Examples of the bond between the central metal atom and the ligand include a metal-nitrogen bond, a metal-carbon bond, a metal-oxygen bond, a metal-phosphorus bond, a metal-sulfur bond, and a metal-halogen bond. A polydentate ligand generally refers to a ligand that is at least two and at most six dentate.
[0056] A metal complex represented by formula (M) The phosphorescent compound is preferably a metal complex represented by formula (M).
[0057] M 1 is preferably an iridium atom, since the luminance life of the light-emitting element using the composition of this embodiment is superior. M 1 If is an iridium atom, n M1 is preferably 2 or 3, and more preferably 3. M 1 If is a platinum atom, n M1 is preferably 2. E 1 and E 2 is preferably a carbon atom.
[0058] Ring R M1 is preferably a 5- or 6-membered aromatic heterocycle having one to four nitrogen atoms as ring-constituting atoms, more preferably a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring, an isoquinoline ring, a diazole ring, or a triazole ring, still more preferably a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, an imidazole ring, or a triazole ring, particularly preferably a pyridine ring, a quinoline ring, or an isoquinoline ring, and especially preferably a pyridine ring, and these rings may have a substituent.
[0059] Ring R M2is preferably a 5- or 6-membered aromatic hydrocarbon ring or a 5- or 6-membered aromatic heterocycle, more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a pyrrole ring, a furan ring, or a thiophene ring, still more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyridine ring, or a diazabenzene ring, particularly preferably a benzene ring, a pyridine ring, or a pyrimidine ring, and especially preferably a benzene ring, and these rings may have a substituent.
[0060] Ring R M1 and ring R M2 The substituent that may be substituted by is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group-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, still more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, particularly preferably an alkyl group or an aryl group, and particularly preferably an aryl group, and these groups may further have a substituent.
[0061] Ring R M1 and ring R M2 The substituent that may be further substituted by the substituent that may be substituted by the group is 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 an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and still more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.
[0062] Ring R M1 and the substituents that may be present on the ring R M2 The substituents which may be possessed by the group may be bonded to each other to form a ring together with the atoms to which they are bonded, but it is preferred that they do not form a ring.
[0063] Ring R M1 and ring R M2 The aryl group, monovalent heterocyclic group, or substituted amino group in the substituent that may be contained in the compound (A) is preferably a group represented by formula (D-A'), formula (D-B'), or formula (D-C'), and more preferably a group represented by formula (D-A'), because this provides a light-emitting element using the composition of this embodiment with a longer luminance life.
[0064] [ka]
[0065] [In the formula, m DA1 , m DA2 and m DA3 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Ar DA1 , Ar DA2 and Ar DA3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 and Ar DA3 When there are multiple, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]
[0066] [ka]
[0067] [In the formula, m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and mDA7 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. DA may be the same or different. Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 When there are multiple, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]
[0068] [ka]
[0069] [In the formula, m DA1 represents an integer greater than or equal to 0. Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 When there are multiple, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.]
[0070] In the formula (D-A'), the formula (D-B') and the formula (D-C'), m DA1 , m DA2, m DA3 , m DA4 , m DA5 , m DA6 and m DA7 is usually an integer of 10 or less, preferably an integer of 5 or less, and more preferably 0 or 1. DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
[0071] In the formula (D-A') and the formula (D-B'), G DA is preferably a group represented by formula (GDA-11) to formula (GDA-15), more preferably a group represented by formula (GDA-11) to formula (GDA-14), even more preferably a group represented by formula (GDA-11) or formula (GDA-14), and particularly preferably a group represented by formula (GDA-11).
[0072] [ka]
[0073] [In the formula, * denotes Ar in formula (D-A'). DA1 , Ar in formula (D-B') DA1 , Ar in formula (D-B') DA2 or Ar in formula (D-B') DA3 Represents a bond with ** indicates Ar in formula (D-A'). DA2 , Ar in formula (D-B') DA2 , Ar in formula (D-B') DA4 or Ar in formula (D-B') DA6 Represents a bond with *** represents Ar in formula (D-A'). DA3 , Ar in formula (D-B') DA3 , Ar in formula (D-B') DA5 or Ar in formula (D-B') DA7 Represents a bond with R DA 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 further have a substituent. DA If there are multiple, they may be the same or different.]
[0074] R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups may have a substituent.
[0075] In the formula (D-A'), the formula (D-B') and the formula (D-C'), Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 is preferably a phenylene group, a fluorenediyl group, a carbazolediyl group, or a group in which some or all of the hydrogen atoms in these groups have been substituted with substituents, more preferably a group represented by formula (A-1) to formula (A-3), formula (A-8), formula (A-9), formula (AA-10), formula (AA-11), formula (AA-33) or formula (AA-34), still more preferably a group represented by formula (ArDA-1) to formula (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to formula (ArDA-3), and particularly preferably a group represented by formula (ArDA-1) or formula (ArDA-2), and these groups may have a substituent.
[0076] [ka]
[0077] [In the formula, R DA represents the same meaning as above. R DBrepresents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DB If there are multiple, they may be the same or different.]
[0078] R DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent.
[0079] In the formula (D-A'), the formula (D-B') and the formula (D-C'), T DA is preferably a group represented by formula (TDA-1) to formula (TDA-3), more preferably a group represented by formula (TDA-1).
[0080] [ka]
[0081] [In the formula, R DA and R DB has the same meaning as above.]
[0082] The group represented by formula (D-A') is preferably a group represented by formula (D-A1) to formula (D-A3), and more preferably a group represented by formula (D-A1).
[0083] [ka]
[0084] [In the formula, R p1 , R p2 and R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are a plurality of groups, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. Multiple np1s may be the same or different.
[0085] The group represented by formula (D-B') is preferably a group represented by formula (D-B1) to formula (D-B3), and more preferably a group represented by formula (D-B1).
[0086] [ka]
[0087] [In the formula, R p1 , R p2 and R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are a plurality of groups, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 and np2 may be the same or different.
[0088] The group represented by formula (D-C') is preferably a group represented by formula (D-C1) to formula (D-C4), more preferably a group represented by formula (D-C1) to formula (D-C3), and further A group represented by formula (D-C1) or formula (D-C2) is preferred, and a group represented by formula (D-C1) is particularly preferred.
[0089] [ka]
[0090] [In the formula, R p4 and R p5R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p4 and R p5 When there are a plurality of, they may be the same or different. np4 represents an integer of 0 to 5, and np5 represents an integer of 0 to 4.
[0091] np1 is preferably 0 or 1, more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2. np5 is preferably an integer of 0 to 2, more preferably 0.
[0092] R p1 , R p2 , R p3 , R p4 and R p5 is preferably an alkyl group or a cycloalkyl group.
[0093] Examples of the group represented by formula (DA') include groups represented by formulae (DA-1) to (DA-12).
[0094] [ka]
[0095] [ka]
[0096] [In the formula, R D represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group. D may be the same or different.]
[0097] Examples of the group represented by formula (DB') include groups represented by formulae (DB-1) to (DB-4).
[0098] [ka]
[0099] [In the formula, R D has the same meaning as above.]
[0100] Examples of the group represented by formula (DC') include groups represented by formulae (DC-1) to (DC-13).
[0101] [ka]
[0102] [In the formula, R D has the same meaning as above.]
[0103] R D is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group, and more preferably a tert-butyl group.
[0104] Ring R M1 and ring R M2 At least one ring selected from the group consisting of the following preferably has a substituent, since this provides excellent solubility.
[0105] Ring R M1 and ring R M2The substituent possessed by at least one ring selected from the group consisting of is preferably an alkyl group, a cycloalkyl group, or a group represented by formula (D-A') to formula (D-C'), more preferably an alkyl group or a group represented by formula (D-A') to formula (D-C'), even more preferably a group represented by formula (D-A') to formula (D-C'), and particularly preferably a group represented by formula (D-A'), and these groups may have a substituent.
[0106] -A D1 ---A D2 Examples of the anionic bidentate ligand represented by - include ligands represented by the following formula:
[0107] [ka]
[0108] [Wherein * represents M 1 represents the site of binding to
[0109] As the metal complex represented by formula (M), metal complexes represented by formulae Ir-1 to Ir-5 are preferred, metal complexes represented by formulae Ir-1 to Ir-3 are more preferred, metal complexes represented by formulae Ir-1 or Ir-2 are even more preferred, and metal complexes represented by formula Ir-1 are particularly preferred.
[0110] [ka]
[0111] [In the formula, R D1 , R D2 , R D3 , R D4 , R D5 , R D6 , R D7 , R D8 , R D11 , R D12 , R D13 , R D14 , R D15 , R D16, R D17 , R D18 , R D19 , R D20 , R D21 , R D22 , R D23 , R D24 , R D25 , R D26 , R D31 , R D32 , R D33 , R D34 , R D35 , R D36 and R D37 R each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. D1 , R D2 , R D3 , R D4 , R D5 , R D6 , R D7 , R D8 , R D11 , R D12 , R D13 , R D14 , R D15 , R D16 , R D17 , R D18 , R D19 , R D20 , R D21 , R D22 , R D23 , R D24 , R D25 , R D26 , R D31 , R D32 , R D33 , R D34 , R D35 , R D36 and R D37 When there are a plurality of groups, they may be the same or different. R D1 and R D2 , R D2 and R D3 , R D3 and R D4 , R D4 and R D5 , RD5 and R D6 , R D6 and R D7 , R D7 and R D8 , R D11 and R D12 , R D12 and R D13 , R D1 3 and R D14 , R D14 and R D15 , R D15 and R D16 , R D16 and R D17 , R D17 and R D18 , R D18 and R D19 , R D19 and R D20 , R D22 and R D23 , R D23 and R D24 , R D24 and R D25 , R D25 and R D26 , R D31 and R D32 , R D32 and R D33 , R D33 and R D34 , R D34 and R D35 , R D35 and R D36 , and R D36 and R D37 may be bonded to each other to form a ring together with the atoms to which they are bonded. -A D1 ---A D2 - has the same meaning as above. n D1 represents 1, 2 or 3, and n D2 represents 1 or 2.]
[0112] R in the metal complex represented by formula Ir-1 D1 ~R D8 and R in the metal complex represented by formula Ir-2. D11 ~R D20and R in the metal complex represented by formula Ir-3. D1 ~R D8 and R D11 ~R D20 and R in the metal complex represented by formula Ir-4. D21 ~R D26 and R in the metal complex represented by formula Ir-5 D31 ~R D37 At least one of each is preferably an alkyl group, a cycloalkyl group, or a group represented by formula (D-A') to formula (D-C'), more preferably an alkyl group or a group represented by formula (D-A') to formula (D-C'), even more preferably a group represented by formula (D-A') to formula (D-C'), and particularly preferably a group represented by formula (D-A'), and these groups may have a substituent.
[0113] R D1 ~R D8 , R D11 ~R D26 , and R D31 ~R D37 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, since this results in a longer luminance life of a light-emitting element using the composition of this embodiment, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, even more preferably a hydrogen atom, an alkyl group, or a group represented by formulas (D-A') to (D-C'), particularly preferably a hydrogen atom, or a group represented by formulas (D-A') to (D-C'), and these groups may have a substituent.
[0114] R D22 and R D33is preferably an alkyl group, a cycloalkyl group, or a group represented by formula (D-A') to formula (D-C'), more preferably a group represented by formula (D-A') to formula (D-C'), and even more preferably a group represented by formula (D-C'), since the luminance life of a light-emitting element using the composition of this embodiment is longer. These groups may have a substituent.
[0115] R D1 ~R D8 , R D11 ~R D26 , and R D31 ~R D37 Examples of the substituents that may be possessed by the ring R and the preferred range thereof are as follows: M1 and ring R M2 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.
[0116] R D1 and R D2 , R D2 and R D3 , R D3 and R D4 , R D4 and R D5 , R D5 and R D6 , R D6 and R D7 , R D7 and R D8 , R D11 and R D12 , R D12 and R D13 , R D13 and R D14 , R D14 and R D15 , R D15 and R D16 , R D16 and R D17 , R D17 and R D18 , R D18 and R D19 , R D19 and R D20 , R D22 and R D23 , R D23 and R D24 , R D24 and R D25 , RD25 and R D26 , R D31 and R D32 , R D32 and R D33 , R D33 and R D34 , R D34 and R D35 , R D35 and R D36 , and R D36 and R D37 are preferably not bonded to each other to form a ring together with the atoms to which they are attached.
[0117] The metal complex represented by formula Ir-1 is preferably a metal complex represented by formulas Ir-11 to Ir-13. The metal complex represented by formula Ir-2 is preferably a metal complex represented by formula Ir-2 The metal complex represented by formula Ir-1 is preferably a metal complex represented by formula Ir-3. The metal complex represented by formula Ir-31 to formula Ir-33 is preferably a metal complex represented by formula Ir-41 to formula Ir-43. The metal complex represented by formula Ir-5 is preferably a metal complex represented by formula Ir-51 to formula Ir-53.
[0118] [ka]
[0119] [ka]
[0120] [In the formula, n D2 represents 1 or 2. D represents a group represented by formula (D-A') to formula (D-C'). A plurality of Ds may be the same or different. R DC represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group These groups may have a substituent. DCmay be the same or different. R DD represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DD may be the same or different.]
[0121] Examples of the phosphorescent compound include the metal complexes shown below.
[0122] [ka]
[0123] [ka]
[0124] [ka]
[0125] [ka]
[0126] [ka]
[0127] [ka]
[0128] Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp., American Dye Source, and others. Alternatively, it can be produced by known methods described in documents such as Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985), Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984), WO 2011 / 024761, WO 02 / 44189, and JP 2006-188673 A.
[0129] (Low molecular compound (B)) The low molecular weight compound (B) contains a boron atom, an oxygen atom, a sulfur atom, a selenium atom, and sp 3 The compound is a low molecular weight compound having a fused heterocyclic skeleton (b) containing at least one atom selected from the group consisting of carbon atoms and nitrogen atoms in the ring. In the low molecular weight compound (B), when the fused heterocyclic skeleton (b) contains a nitrogen atom, it is preferable that at least one of the nitrogen atoms contained in the fused heterocyclic skeleton (b) is a nitrogen atom that does not form a double bond, and it is more preferable that all of the nitrogen atoms contained in the fused heterocyclic skeleton (b) are nitrogen atoms that do not form a double bond. The low molecular weight compound (B) is preferably a low molecular weight compound that does not contain a transition metal element (that is, a low molecular weight compound that is composed only of main group elements).
[0130] The number of carbon atoms in the fused heterocyclic skeleton (b) is usually 1 to 60, preferably 5 to 40, and more preferably 10 to 25, not including the number of carbon atoms in the substituent. The number of heteroatoms in the fused heterocyclic skeleton (b), not including the number of heteroatoms in the substituents, is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, even more preferably 2 to 5, and particularly preferably 2 or 3. The number of boron atoms in the fused heterocyclic skeleton (b) is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1, not including the number of boron atoms in the substituents. Oxygen atom, sulfur atom, selenium atom, sp 3The total number of carbon atoms and nitrogen atoms, not including the number of atoms of substituents, is usually 1 to 20, preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 2.
[0131] The fused heterocyclic skeleton (b) preferably contains a boron atom and at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom in the ring, since this reduces the driving voltage of a light-emitting device using the composition of this embodiment. It is more preferable that the fused heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring, and it is even more preferable that the fused heterocyclic skeleton (b) contains a nitrogen atom that does not form a double bond with the boron atom in the ring.
[0132] The fused heterocyclic skeleton (b) is preferably a 3- to 12-cyclic fused heterocyclic skeleton, more preferably a 3- to 6-cyclic fused heterocyclic skeleton, and even more preferably a 5-cyclic fused heterocyclic skeleton, since the driving voltage of the light-emitting device using the composition of this embodiment is lower.
[0133] The fused heterocyclic skeleton (b) can also be said to be a compound having a heterocyclic group (b') containing the fused heterocyclic skeleton (b).
[0134] The heterocyclic group (b') is a group consisting of a boron atom, an oxygen atom, a sulfur atom, a selenium atom, and a sp 3 It may be a group in which one or more hydrogen atoms directly bonded to atoms constituting the ring have been removed from a polycyclic heterocycle containing at least one atom selected from the group consisting of carbon atoms and nitrogen atoms in the ring, and the group may have a substituent. In the heterocyclic group (b'), the polycyclic heterocycle is preferably a polycyclic heterocycle containing a boron atom and at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom in the ring, since this reduces the driving voltage of the light-emitting device using the composition of this embodiment. More preferably, it is a polycyclic heterocycle containing a boron atom and a nitrogen atom in the ring. Even more preferably, it is a polycyclic heterocycle containing a nitrogen atom that does not form a double bond with the boron atom in the ring. In the heterocyclic group (b'), the polycyclic heterocycle is preferably a heterocycle having 3 to 12 rings, more preferably a heterocycle having 3 to 6 rings, and even more preferably a heterocycle having 5 rings, since this lowers the driving voltage of the light-emitting device using the composition of this embodiment.
[0135] The substituent that the heterocyclic group (b') may have is preferably a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, 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, still more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and particularly preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.
[0136] The aryl group in the substituent that the heterocyclic group (b') may have is preferably a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon that is directly bonded to an atom that constitutes the ring. It is a group in which one hydrogen atom has been removed, more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon, still more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, naphthalene, anthracene, phenanthrene, or fluorene, and particularly preferably a phenyl group, and these groups may have a substituent.
[0137] The monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or bicyclic to hexacyclic heterocycle, a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic or tricyclic heterocycle, more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, and particularly preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from pyridine, diazabenzene or triazine, and these groups may have a substituent.
[0138] In the substituted amino group in the substituent that the heterocyclic group (b') may have, 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 may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent that the amino group has are the same as the examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have, respectively.
[0139] The substituent that the heterocyclic group (b') may further have is preferably a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but preferably do not have a further substituent.
[0140] Examples and preferred ranges of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that the heterocyclic group (b') may further have are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that the heterocyclic group (b') may have.
[0141] The term "nitrogen atom not forming a double bond" means a nitrogen atom that is bonded to three other atoms via single bonds. "Containing a nitrogen atom not forming a double bond in the ring" means that the ring contains -N(-R N )-(wherein, R N represents a hydrogen atom or a substituent.) or a group represented by the following formula:
[0142] [ka]
[0143] The low molecular weight compound (B) is preferably a thermally activated delayed fluorescence (TADF) compound, since the driving voltage of the light-emitting device using the composition of this embodiment is lowered. Here, the thermally activated delayed fluorescent compound is a compound having thermally activated delayed fluorescent properties.
[0144] The absolute value of the difference between the energy level of the lowest excited triplet state of the low molecular weight compound (B) and the energy level of the lowest excited singlet state (hereinafter referred to as "ΔE ST ") may be 2.0 eV or less, 1.5 eV or less, 1.0 eV or less, or 0.80 eV or less, but is preferably 0.60 eV or less, more preferably 0.55 eV or less, and even more preferably 0.50 eV or less, since this will result in a lower driving voltage for the light-emitting device using the composition of this embodiment. In addition, ΔE ST may be 0.001 eV or more, 0.01 eV or more, 0.10 eV or more, 0.20 eV or more, 0.30 eV or more, or 0.40 eV or more.
[0145] The molecular weight of the low molecular weight compound (B) is preferably 1×10 2 ~5×10 3 and more preferably 2×10 2 ~3×10 3 and more preferably 3×10 2 ~1.5×10 3 and particularly preferably 4 × 10 2 ~1×10 3 is.
[0146] The low molecular weight compound (B) is preferably a compound represented by formula (1-1), formula (1-2) or formula (1-3), more preferably a compound represented by formula (1-2) or formula (1-3), and even more preferably a compound represented by formula (1-2), because the driving voltage of the light-emitting device using the composition of this embodiment is lower.
[0147] [ka]
[0148] [In the formula, Ar 1 , Ar 2 and Ar 3 each independently represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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. Y 1 represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, an alkylene group, or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, 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. Y 2 and Y 3are each independently a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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. Ry 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. When there are multiple substituents, 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. When there are multiple Ry, they may be the same or different. Y 1 and Ar 1 may be bonded directly or via a divalent group to form a ring. 1 and Ar 2 may be bonded directly or via a divalent group to form a ring. 2 and Ar 1 may be bonded directly or via a divalent group to form a ring. 2 and Ar 3 may be bonded directly or via a divalent group to form a ring. 3 and Ar 2 may be bonded directly or via a divalent group to form a ring. 3 and Ar 3 may be bonded directly or via a divalent group to form a ring.
[0149] Ar 1 , Ar 2 and Ar 3is preferably a group obtained by removing one or more hydrogen atoms directly bonded to a ring-constituting atom from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon or a monocyclic or bicyclic to hexacyclic heterocycle, since this reduces the driving voltage of a light-emitting device using the composition of this embodiment; more preferably a group obtained by removing one or more hydrogen atoms directly bonded to a ring-constituting atom from a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon or a monocyclic, bicyclic, or tricyclic heterocycle; even more preferably a group obtained by removing one or more hydrogen atoms directly bonded to a ring-constituting atom from a monocyclic aromatic hydrocarbon or a monocyclic heterocycle; particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to a ring-constituting atom from benzene, pyridine, or diazabenzene; and particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to a ring-constituting atom from benzene, and these groups may have a substituent. Ar 1 , Ar 2 and Ar 3 The examples and preferred range of the substituents which may be possessed by the heterocyclic group (b') are the same as the examples and preferred range of the substituents which may be possessed by the heterocyclic group (b').
[0150] Y 1 is preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)-, or an alkylene group, since the driving voltage of the light-emitting element using the composition of this embodiment is lower, more preferably an oxygen atom, a sulfur atom, or a group represented by -N(Ry)-, and even more preferably a group represented by -N(Ry)-, and these groups may have a substituent.
[0151] Y 2 and Y 3is preferably a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, an alkylene group, or a cycloalkylene group, since the driving voltage of a light-emitting element using the composition of this embodiment is lower; more preferably a single bond, an oxygen atom, a sulfur atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, or an alkylene group; even more preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)-, or an alkylene group; particularly preferably an oxygen atom, a sulfur atom, or a group represented by -N(Ry)-, and especially preferably a group represented by -N(Ry)-, and these groups may have a substituent.
[0152] Y 2 and Y 3 The arylene group in the formula (I) is preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, even more preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, particularly preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from benzene, naphthalene or fluorene, and particularly preferably a phenylene group, and these groups may have a substituent.
[0153] Y 2 and Y 3 The divalent heterocyclic group in the formula (I) is preferably a group in which two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting the ring have been removed from a monocyclic or bicyclic to hexacyclic heterocyclic ring, more preferably a group in which two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting the ring have been removed from a monocyclic, bicyclic or tricyclic heterocyclic ring, and even more preferably Preferably, it is a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring (preferably carbon atoms) from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, or 5,10-dihydrophenazine, and particularly preferably, it is a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring (preferably carbon atoms) from pyridine, diazabenzene, triazine, carbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, or 5,10-dihydrophenazine, and especially preferably, it is a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring (preferably carbon atoms) from pyridine, diazabenzene, or triazine, and these groups may have a substituent. Y 1 , Y 2 and Y 3 The alkylene group in the formula (I) is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
[0154] Since the driving voltage of the light-emitting device using the composition of this embodiment is lower, Y 1 , Y 2 and Y 3 are preferably all oxygen atoms, sulfur atoms or groups represented by -N(Ry)-, and Y 1 , Y 2 and Y 3 It is more preferable that all of the above are groups represented by -N(Ry)-.
[0155] Y 1 , Y 2 and Y 3 The examples and preferred range of the substituents which may be possessed by the heterocyclic group (b') are the same as the examples and preferred range of the substituents which may be possessed by the heterocyclic group (b').
[0156] Ry is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent. Examples and preferred ranges of the aryl group and monovalent heterocyclic group for Ry are the same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have, respectively. Examples and preferred ranges of the substituents that Ry may have are the same as the examples and preferred ranges of the substituents that the heterocyclic group (b') may have.
[0157] Y 1 and Ar 1 may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). Y 1 and Ar 1 When the groups bond to each other via a divalent group to form a ring, the divalent group is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, or —N(R 0 )-, -B(R 0 )-, a group represented by -O-, a group represented by -S-, or a group represented by -Se-, and more preferably an alkylene group, a cycloalkylene group, -N(R 0 )-, -B(R 0 )-, -O-, -S- or -Se-, and more preferably an alkylene group, -N(R 0 )-, a group represented by -O-, or a group represented by -S-, and particularly preferred are a group represented by -O-, a group represented by -S-, or -N(R 0 )-, and particularly preferably, -N(R 0 )-, and these groups may have a substituent. Y 1 and Ar 1and Y are bonded to each other via a divalent group to form a ring. Examples and preferred ranges of the arylene group, divalent heterocyclic group, and alkylene group in the divalent group are respectively listed below. 2 and Y 3 The examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in the above are the same as those in the above. Y 1 and Ar 1 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the substituents that the divalent group may have are as follows: 2 and Y 3 The examples and preferred ranges of the substituents that may be possessed by the group are the same as those of the substituents that may be possessed by the group. Y 1 and Ar 1 and R in the divalent group when they are bonded to form a ring via a divalent group 0 Examples and preferred ranges of are the same as those of Ry.
[0158] Y 1 and Ar 2 and may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). 1 and Ar 2 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group include: 1 and Ar 1 and are bonded via a divalent group to form a ring, the examples and preferred ranges of which are the same as those of the divalent group. Y 2 and Ar 1 and may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). 2 and Ar 1 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group include: 1 and Ar 1 and are bonded via a divalent group to form a ring, the examples and preferred ranges of which are the same as those of the divalent group. Y 2 and Ar 3 and may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). 2 and Ar 3 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group include: 1 and Ar 1 and are bonded via a divalent group to form a ring, the examples and preferred ranges of which are the same as those of the divalent group. Y 3 and Ar 2 and may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). 3 and Ar 2 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group include: 1 and Ar 1 and are bonded via a divalent group to form a ring, the examples and preferred ranges of which are the same as those of the divalent group. Y 3 and Ar 3 and may be bonded directly or via a divalent group to form a ring, but it is preferable that they do not form a ring, as this facilitates the synthesis of the low molecular weight compound (B). 3 and Ar 3 When Y and Y are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group include: 1 and Ar 1 and are bonded via a divalent group to form a ring, the examples and preferred ranges of which are the same as those of the divalent group.
[0159] Examples of the low molecular weight compound (B) include compounds represented by the following formula: 1 represents an oxygen atom or a sulfur atom. 1 When there are multiple groups, they may be the same or different.
[0160] [ka]
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[0162] The maximum peak wavelength of the emission spectrum of the low molecular weight compound (B) at 25°C is preferably 380 nm or more, more preferably 400 nm or more, even more preferably 420 nm or more, and particularly preferably 440 nm or more. The maximum peak wavelength of the emission spectrum of the low molecular weight compound (B) at 25°C is preferably 750 nm or less, more preferably 620 nm or less, even more preferably 570 nm or less, particularly preferably 495 nm or less, and especially preferably 480 nm or less. The half width of the maximum peak of the emission spectrum of the low molecular weight compound (B) at 25° C. is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 30 nm or less, and particularly preferably 25 nm or less. The maximum peak wavelength of the emission spectrum of the low molecular weight compound (B) at room temperature was measured by dissolving the low molecular weight compound (B) in an organic solvent such as xylene, toluene, chloroform, or tetrahydrofuran to prepare a dilute solution (1 × 10 -6 Mass%~1×10 -3 % by mass, can be evaluated by measuring the PL spectrum of the dilute solution at room temperature. Xylene is preferred as the organic solvent for dissolving the low molecular weight compound (B).
[0163] (polymer compound) A structural unit represented by formula (X) Polymer compound 1 and polymer compound 2 (hereinafter, these may be collectively referred to as "polymer compound (I)") preferably contain a structural unit represented by formula (X), because polymer compound (I) has excellent hole transport properties and the driving voltage of a light-emitting device using the composition of this embodiment is lowered.
[0164] aX1 is preferably an integer of 2 or less, more preferably 1, since the luminance life of a light-emitting device using the composition of this embodiment is excellent. a X2 is preferably an integer of 2 or less, and more preferably 0, since the luminance life of a light-emitting device using the composition of this embodiment is excellent. R X1 , R X2 and R X3 is preferably an alkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.
[0165] Ar X1 and Ar X3 The arylene group represented by the formula (A-1) is particularly preferably a group represented by formula (A-1) or formula (A-9), and particularly preferably a group represented by formula (A-1), and these groups may have a substituent. Ar X1 and Ar X3 The divalent heterocyclic group represented by the formula (AA-1), (AA-2) or (AA-7) to (AA-26) is particularly preferred, and these groups may have a substituent. Ar X1 and Ar X3 is preferably an arylene group which may have a substituent. Ar X2 and Ar X4 The arylene group represented by the formula (A-1), (A-6), (A-7), (A-9) to (A-11) or (A-19) is particularly preferably a group, and these groups may have a substituent.
[0166] Ar X2 and Ar X4 A particularly preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 The particularly preferred range is the same as that of the divalent heterocyclic group represented by the following formula: Ar X2 and Ar X4In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the particularly preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, Ar X1 and Ar X3 The particularly preferred ranges are the same as the particularly preferred ranges of the arylene group and divalent heterocyclic group represented by the following formula:
[0167] Ar X2 and Ar X4 Examples of the divalent group represented by the formula (I) in which at least one arylene group and at least one divalent heterocyclic group are directly bonded include groups represented by the formula (I), which may have a substituent.
[0168] [ka]
[0169] [In the formula, R XX represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.]
[0170] R XX is preferably an alkyl group or an aryl group, and these groups may have a substituent.
[0171] Ar X2 and Ar X4 is preferably an arylene group which may have a substituent. Ar X1 ~Ar X4 and R X1 ~R X3 The substituent that the group represented by the formula (I) may have is preferably an alkyl group or an aryl group, and these groups may further have a substituent.
[0172] The structural unit represented by formula (X) is preferably a structural unit represented by formulas (X-1) to (X-7), more preferably a structural unit represented by formulas (X-3) to (X-7), and even more preferably a structural unit represented by formulas (X-3) to (X-6).
[0173] [ka]
[0174] [ka]
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[0177] [In the formula, R X4 and R X5 each independently represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group, and these groups may have a substituent. Multiple Rs X4 may be the same or different. 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 atoms to which they are attached.
[0178] Specific examples of the constitutional unit represented by formula (X) include constitutional units represented by formulas (X1-1) to (X1-19), and preferably constitutional units represented by formulas (X1-6) to (X1-14).
[0179] [ka]
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[0187] When the polymer compound (I) contains a structural unit represented by formula (X), The content of the structural unit represented by formula (X) in the polymer compound (I) may be within a range that allows the polymer compound (I) to exhibit its functions. When the polymer compound (I) contains a structural unit represented by formula (X), the content of the structural unit represented by formula (X) in the polymer compound (I) is, for example, 0.01 to 100 mol % relative to the total content of the structural units contained in the polymer compound (I). Since the hole transport properties of the polymer compound (I) are excellent and the driving voltage of a light-emitting device using the composition of this embodiment is lower, the content is preferably 0.05 to 90 mol %, more preferably 0.1 to 70 mol %, even more preferably 0.2 to 50 mol %, particularly preferably 0.5 to 30 mol %, and particularly preferably 1 to 10 mol %. In the polymer compound (I), the structural unit represented by formula (X) may be contained in the polymer compound (I) either alone or in combination of two or more types.
[0188] A structural unit represented by the formula (Y) The polymer compound (I) preferably contains a constitutional unit represented by formula (Y), since this leads to a lower driving voltage of a light-emitting device using the composition of this embodiment.
[0189] Ar Y1 The arylene group represented by the formula (I) is preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, still more preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, and particularly preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from benzene, phenanthrene, dihydrophenanthrene or fluorene, and these groups may have a substituent.
[0190] Ar Y1The divalent heterocyclic group represented by the formula (I) is preferably a group in which two hydrogen atoms directly bonded to atoms constituting the ring have been removed from a monocyclic or bicyclic to hexacyclic heterocycle, more preferably a group in which two hydrogen atoms directly bonded to atoms constituting the ring have been removed from a monocyclic, bicyclic or tricyclic heterocycle, and even more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, or phenothiazine, because the driving voltage of the light-emitting element using the composition of this embodiment is lower. , 9,10-dihydroacridine, or 5,10-dihydrophenazine, by removing two hydrogen atoms directly bonded to atoms constituting the ring (preferably carbon atoms or nitrogen atoms, more preferably carbon atoms), and particularly preferred are groups obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring (preferably carbon atoms or nitrogen atoms, more preferably carbon atoms) from pyridine, diazabenzene, triazine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, or phenothiazine, and these groups may have a substituent.
[0191] Ar Y1 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, Ar Y1 The preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:
[0192] Ar Y1 In the above, examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include groups represented by the following formulae, and these groups may have a substituent.
[0193] [ka]
[0194] Ar Y1is preferably an arylene group which may have a substituent, since the driving voltage of the light-emitting device using the composition of this embodiment is lowered.
[0195] Ar Y1 The substituent that the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, even more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and particularly preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.
[0196] Ar Y1 The aryl group in the substituent that may be possessed by the group represented by the formula (I) is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, even more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, and particularly preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from benzene, phenanthrene, dihydrophenanthrene or fluorene, and these groups may further have a substituent, because this reduces the driving voltage of a light-emitting element using the composition of this embodiment.
[0197] Ar Y1The monovalent heterocyclic group in the substituent that may be included in the group represented by the formula (I) is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic or bicyclic to hexacyclic heterocycle, more preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring has been removed from a monocyclic, bicyclic or tricyclic heterocycle, and even more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, It is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring (preferably a carbon atom or a nitrogen atom) from phen, phenoxazine, phenothiazine, 9,10-dihydroacridine, or 5,10-dihydrophenazine, and is particularly preferably a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring (preferably a carbon atom or a nitrogen atom) from pyridine, diazabenzene, triazine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, or phenothiazine, and these groups may further have a substituent.
[0198] Ar Y1 In the substituted amino group in the substituent that the group represented by the formula (I) may have, 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 may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent that the amino group has are respectively given as Ar Y1 It is expressed as The examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the group may have are the same as those of the aryl group and monovalent heterocyclic group.
[0199] Ar Y1The substituent that may be further possessed by the substituent that the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent, but preferably do not have a further substituent.
[0200] Ar Y1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be further substituted by the substituent that may be substituted by the group represented by the formula: Y1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have.
[0201] The structural unit represented by formula (Y) is preferably a structural unit represented by formula (Y-1) or formula (Y-2), since the driving voltage of the light-emitting device using the composition of this embodiment is lowered.
[0202] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably a hydrogen atom or an alkyl group, and these groups may have a substituent.
[0203] In formula (Y-1), R Y1 At least one of (preferably R Y1At least two of the above) are preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, since the driving voltage of a light-emitting element using the composition of this embodiment is lower, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, even more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group, and these groups may have a substituent.
[0204] R Y2 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since the driving voltage of the light-emitting element using the composition of this embodiment is lower, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and even more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent.
[0205] R Y1 and R Y2 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in Y1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have. R Y1 and R Y2 Examples of the substituents that may be possessed by Ar and the preferred ranges thereof are as follows: Y1 The examples and preferred ranges of the substituents that may be possessed by the group represented by the formula:
[0206] X Y1 is preferably -C(R Y2 )2- or -C(R Y2 )2-C(R Y2 )2-, and more preferably, -C(R Y2 )2- is a group represented by the formula:
[0207] Examples of the structural unit represented by formula (Y) include those represented by formulas (Y-101) to (Y-141): structural units comprising at least one type of divalent heterocyclic group represented by formulas (Y-201) to (Y-209); and structural units comprising a divalent group in which at least one type of arylene group and at least one type of divalent heterocyclic group are directly bonded to each other, represented by formulas (Y-301) to (Y-306).
[0208] [ka]
[0209] [ka]
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[0221] When the polymer compound (I) contains a structural unit represented by formula (Y), the content of the structural unit represented by formula (Y) contained in the polymer compound (I) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains a structural unit represented by formula (Y), the content of the structural unit represented by formula (Y) contained in the polymer compound (I) is, for example, 1 to 100 mol % relative to the total content of structural units contained in the polymer compound (I). Since this further reduces the driving voltage of a light-emitting device using the composition of this embodiment, the content is preferably 10 to 100 mol %, more preferably 30 to 100 mol %, even more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, and particularly preferably 90 to 100 mol %. In the polymer compound (I), the structural unit represented by formula (Y) may be contained in the polymer compound (I) either alone or in combination of two or more types.
[0222] The polymer compound (I) preferably contains a structural unit represented by formula (X) and a structural unit represented by formula (Y), because the polymer compound (I) has excellent hole transport properties and the driving voltage of a light-emitting device using the composition of this embodiment is further reduced. When the polymer compound (I) contains a structural unit represented by formula (X) and a structural unit represented by formula (Y), the total content of the structural unit represented by formula (X) and the structural unit represented by formula (Y) contained in the polymer compound (I) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains a structural unit represented by formula (X) and a structural unit represented by formula (Y), the total content of the structural unit represented by formula (X) and the structural unit represented by formula (Y) contained in the polymer compound (I) is, for example, 1 to 100 mol %, and is preferably 10 to 100 mol %, more preferably 30 to 100 mol %, even more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, and particularly preferably 90 to 100 mol %, because this provides excellent hole transport properties for the polymer compound (I) and further reduces the driving voltage of a light-emitting device using the composition of this embodiment.
[0223] A structural unit represented by the formula (Z) Since the luminance life of a light-emitting device using the composition of this embodiment is excellent, it is preferable that the polymer compound (I) contains a structural unit represented by formula (Z). Note that the structural unit represented by formula (Z) does not include a structural unit represented by formula (Y).
[0224] Ar Z In the divalent heterocyclic group having a group represented by -N= in the ring represented by the formula (I), the number of groups represented by -N= is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and even more preferably 3.
[0225] Ar Z In the divalent heterocyclic group having a group represented by -N= in the ring represented by the formula (I), the number of carbon atoms constituting the ring is usually 1 to 60, preferably 2 to 30, more preferably 3 to 15, and even more preferably 3 to 5.
[0226] Ar ZExamples of the divalent heterocyclic group having a group represented by -N= in the ring represented by the formula (I) include a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, a tetraazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, a tetraaza Examples of the ring include an anthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a triazaphenanthrene ring, a tetraazaphenanthrene ring, and a ring in which an aromatic ring is condensed with any of these heterocycles, and groups in which two hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring have been removed. Preferably, the ring is a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazole ring, a benzotriazole ring, or a benzazole ring, since this will provide a light-emitting element using the composition of the present embodiment with a longer luminance life. a benzoxadiazole ring, a benzothiadiazole ring, a benzothiazole ring, a benzoxazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, a tetraazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, a tetraazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a triazaphenanthrene ring, or a tetraazaphenanthrene ring; and more preferably a group in which two hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a diazole ring, triazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, or triazaphenanthrene ring, and even more preferably a pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring,It is a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a diazanaphthalene ring, a triazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, or a triazaphenanthrene ring, and is particularly preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a pyridine ring, a diazabenzene ring, or a triazine ring, and is particularly preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a triazine ring, and these groups may have a substituent.
[0227] Since the synthesis of polymer compound (I) becomes easy, Ar Z The substituent that may be substituted by the alkyl group is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a 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; still more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group; particularly preferably an alkyl group, a cycloalkyl group, or an aryl group; and particularly preferably an aryl group, and these groups may further have a substituent. Since the luminance life of the light-emitting device using the composition of this embodiment is superior, Ar Z The substituent that may be substituted by the alkyl group is 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 an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an aryl group or a monovalent heterocyclic group, and particularly preferably an aryl group, and these groups may further have a substituent.
[0228] Ar Z When there are a plurality of substituents that may be possessed by the group, they are preferably not bonded to each other to form a ring together with the atoms to which they are bonded.
[0229] Ar ZThe substituent that may be further substituted by the substituent may be an alkyl group. , a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is preferred, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is more preferred, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is even more preferred, an alkyl group or an aryl group is particularly preferred, and an alkyl group is particularly preferred, and these groups may further have a substituent.
[0230] Ar Z is preferably a group represented by formula (ArZ-1) to formula (ArZ-12), more preferably a group represented by formula (ArZ-1) to formula (ArZ-9), still more preferably a group represented by formula (ArZ-1) to formula (ArZ-5), particularly preferably a group represented by formula (ArZ-1), formula (ArZ-2) or formula (ArZ-4), and particularly preferably a group represented by formula (ArZ-4), since the luminance life of a light-emitting element using the composition of this embodiment is longer.
[0231] [ka]
[0232] [In the formula, R 1Z represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or a bond, and these groups may have a substituent. 1Z may be the same or different. However, if there are multiple R 1Z Of these, two are Ar Z1 or Ar Z2 is a bond that bonds to .]
[0233] R 1Z When R is not a bond, it becomes easier to synthesize polymer compounds. 1Zis preferably a hydrogen atom, 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 a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, even more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably a hydrogen atom or an aryl group, and these groups may have a substituent. R 1Z When is other than a bond, the luminance life of the light-emitting device using the composition of this embodiment is superior. Therefore, R 1Z is preferably a hydrogen atom, 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 a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, even more preferably a hydrogen atom, an aryl group, or a monovalent heterocyclic group, and particularly preferably a hydrogen atom or an aryl group, and these groups may have a substituent.
[0234] R 1Z Examples of the substituents that may be possessed by Ar and the preferred ranges thereof are as follows: Z The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.
[0235] Ar Z1 and Ar Z2 The arylene group in the formula (A-1) is preferably a group represented by formula (A-1) to formula (A-10), formula (A-19) or formula (A-20), more preferably a group represented by formula (A-1) to formula (A-7), formula (A-9) or formula (A-19), still more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), and particularly preferably a group represented by formula (A-1) or formula (A-2), since the luminance life of a light-emitting device using the composition of this embodiment is longer.
[0236] Ar Z1 and Ar Z2 Examples and preferred ranges of the divalent heterocyclic group in ArY1 The examples and preferred ranges are the same as those of the divalent heterocyclic group represented by the following formula:
[0237] Ar Z1 and Ar Z2 Examples of the substituents that may be possessed by Ar and the preferred range thereof are as described above. Z The examples and preferred ranges of the substituents that may be possessed by Ar are the same as those of Ar Z1 and Ar Z2 Examples of the substituents that may be further substituted by the substituents that may be substituted by Ar Z The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.
[0238] Ar Z1 and Ar Z2 is preferably an arylene group which may have a substituent.
[0239] n Z1 and n Z2 is preferably an integer of 0 or more and 3 or less, more preferably 1 or 2, and even more preferably 1.
[0240] The structural unit represented by the formula (Z) is preferably a structural unit represented by the formula (ZA), since the luminance life of the light-emitting device using the composition of this embodiment is superior.
[0241] [ka]
[0242] [In the formula, Ar Z1 , Ar Z2 , n Z1 and n Z2 represents the same meaning as above. Z 1 is -C(R 3Z )= or -N=. Three Z 1 may be the same or different. However, if there are three Z 1At least one of these is a group represented by -N=. R 2Z and R 3Z are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituent, and represents a substituted amino group or a halogen atom, and these groups may have a substituent.]
[0243] There are three Zs 1 Among these, it is preferred that at least two of them are groups represented by -N=, and it is more preferred that all of them are groups represented by -N=.
[0244] R 2Z is 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, since this facilitates the synthesis of the polymer compound, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, even more preferably an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an aryl group, and these groups may have a substituent. R 2Z is 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, since this provides a light-emitting element using the composition of this embodiment with a longer luminance life; more preferably an aryl group, a monovalent heterocyclic group, or a substituted amino group; even more preferably an aryl group or a monovalent heterocyclic group; and particularly preferably an aryl group, and these groups may further have a substituent.
[0245] R 3Zis preferably a hydrogen atom, 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 a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, even more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups may have a substituent.
[0246] R 2Z and R 3Z Examples of the substituents that may be possessed by Ar and the preferred ranges thereof are as follows: Z The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.
[0247] The structural unit represented by formula (ZA) is preferably a structural unit represented by formula (Z-A1) to formula (Z-A4), more preferably a structural unit represented by formula (Z-A1) or formula (Z-A3), and even more preferably a structural unit represented by formula (Z-A1), because the luminance life of the light-emitting element using the composition of this embodiment is longer.
[0248] [ka]
[0249] [In the formula, R 2Z and R 3Z has the same meaning as above.]
[0250] Examples of the structural unit represented by formula (Z) include structural units represented by formulas (Z-1) to (Z-47), and preferred are structural units represented by formulas (Z-1) to (Z-28) or (Z-41) to (Z-47).
[0251] [ka]
[0252] [ka]
[0253]
change
[0254]
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[0255]
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[0256]
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[0257]
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[0258]
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[0259]
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[0260]
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[0261]
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[0262]
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[0263] [ka]
[0264] [In the formula, Z 2 represents a group represented by -CH= or a group represented by -N=. 2 may be the same or different. However, if there are multiple Z 2 At least one of these is a group represented by -N=. Z 3 represents a group represented by -O- or a group represented by -S-. 3 may be the same or different.]
[0265] Multiple Zs 2 Among these, it is preferred that at least two of them are groups represented by -N=, and it is more preferred that all of them are groups represented by -N=.
[0266] The content of the structural unit represented by formula (Z) is preferably 0.01 or more, because the luminance life of the light-emitting element using the composition of this embodiment is superior. It is preferably 0.1 to 50 mol %, more preferably 1 to 30 mol %, and even more preferably 5 to 15 mol %, based on the total amount of units.
[0267] The polymer compound containing the constitutional unit represented by formula (Z) may contain only one type of constitutional unit represented by formula (Z), or may contain two or more types of constitutional units represented by formula (Z).
[0268] A polymer compound containing a structural unit represented by formula (Z) preferably further contains a structural unit represented by formula (Y) (different from the structural unit represented by formula (Z)) because the luminance life of a light-emitting device using the composition of this embodiment is superior. Furthermore, a polymer compound containing a structural unit represented by formula (Z) preferably further contains a structural unit represented by formula (X) because the polymer compound has excellent hole transport properties.
[0269] A polymer compound containing a structural unit represented by formula (Z) has excellent hole transport properties, and the luminance life of a light-emitting element using the composition of this embodiment is superior. Therefore, it is preferable that the polymer compound further contains a structural unit represented by formula (X) and a structural unit represented by formula (Y).
[0270] Structural unit (A) The structural unit (A) is a structural unit having a group in which one or more hydrogen atoms have been removed from a phosphorescent compound, and is preferably a structural unit having a group in which one or more hydrogen atoms have been removed from a metal complex represented by formula (M). When the polymer compound (I) contains the structural unit (A), the structural unit (A) is preferably a structural unit having a group obtained by removing from 1 to 5 hydrogen atoms from a metal complex represented by formula (M), more preferably a structural unit having a group obtained by removing from 1 to 3 hydrogen atoms from a metal complex represented by formula (M), and even more preferably a structural unit having a group obtained by removing from a metal complex represented by formula (M) one or two hydrogen atoms. When the polymer compound (I) contains the structural unit (A), the structural unit (A) is preferably a structural unit represented by formula (AP-1), formula (AP-2) or formula (AP-3), since this facilitates synthesis of the polymer compound (I) and reduces the driving voltage of a light-emitting device using the composition of the present embodiment, more preferably a structural unit represented by formula (AP-1) or formula (AP-2), and even more preferably a structural unit represented by formula (AP-1).
[0271] [ka]
[0272] [In the formula, M AP1 represents a group in which one hydrogen atom has been removed from a metal complex represented by formula (M). M AP2 represents a group obtained by removing two hydrogen atoms from a metal complex represented by formula (M). M AP3 represents a group in which three hydrogen atoms have been removed from a metal complex represented by formula (M). L AP1 are each independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R AP1 )-, an oxygen atom, or a sulfur atom, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different. They may be bonded to each other to form a ring together with the atoms to which they are bonded. AP1 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. When a plurality of such substituents are present, 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. L AP1 When there are a plurality of groups, they may be the same or different. n AP1 represents an integer between 0 and 10. Ar AP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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.
[0273] L AP1 Examples and preferred ranges of L BP1 The examples and preferred ranges are the same as those of the above. R AP1 Examples and preferred ranges of R BP1 The examples and preferred ranges are the same as those of the above. n AP1 Examples and preferred ranges of n BP1 The examples and preferred ranges are the same as those of the above. Ar AP1 Examples and preferred ranges of Ar BP1 The examples and preferred ranges are the same as those of the above.
[0274] Examples of the structural unit (A) include structural units represented by formulae (1G-1) to (1G-13), (2G-1) to (2G-16), (3G-1) to (3G-24), and (4G-1) to (4G-8).
[0275] [ka]
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[0289] [In the formula, R p represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and these groups may have a substituent, and are preferably a methyl group, a tert-butyl group, an n-hexyl group, a 2-ethylhexyl group, a group represented by formula (Rp-1), or a 2-ethylhexyloxy group, and more preferably a tert-butyl group or a group represented by formula (Rp-1). De represents a group represented by formula (D-A') to formula (D-C'). A plurality of De may be the same or different.
[0290] [ka]
[0291] When the polymer compound (I) contains the structural unit (A), it is preferable that the polymer compound (I) further contains at least one structural unit selected from the group consisting of the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y), because this will result in a lower driving voltage for a light-emitting device using the composition of this embodiment. That is, when the polymer compound (I) contains the structural unit (A), it is preferable that the polymer compound (I) is a polymer compound that contains the structural unit (A) and at least one structural unit selected from the group consisting of the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y). When the polymer compound (I) contains at least one structural unit selected from the group consisting of structural units represented by the aforementioned formula (X) and structural units represented by the aforementioned formula (Y), and the structural unit (A), it is preferable that the structural unit (A) is different from the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y).
[0292] When the polymer compound (I) contains the structural unit (A), the polymer compound (I) has excellent hole transport properties, and the driving voltage of a light-emitting device using the composition of this embodiment is lowered. Therefore, it is preferable that the polymer compound (I) further contains a structural unit represented by the above-mentioned formula (X). When the polymer compound (I) contains the structural unit (A), it is preferable that the polymer compound (I) further contains a structural unit represented by the above-mentioned formula (Y), since this will result in a lower driving voltage for a light-emitting device using the composition of this embodiment. When the polymer compound (I) contains the structural unit (A), the polymer compound (I) has excellent hole transport properties and the driving voltage of a light-emitting device using the composition of the present embodiment is lowered. Therefore, it is preferable that the polymer compound (I) further contains a structural unit represented by the above-mentioned formula (X) and a structural unit represented by the above-mentioned formula (Y).
[0293] When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) in the polymer compound (I) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) in the polymer compound (I) may be within a range that allows the polymer compound (I) to function. The content of is, for example, 0.01 to 99.9 mol % relative to the total content of structural units contained in the polymer compound (I). Since the hole transport property is excellent and the driving voltage of a light-emitting device using the composition of this embodiment is lower, the content is preferably 0.05 to 90 mol %, more preferably 0.1 to 70 mol %, even more preferably 0.2 to 50 mol %, particularly preferably 0.5 to 30 mol %, and especially preferably 1 to 10 mol %. When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the above-mentioned formula (X), the polymer compound (I) may contain only one type of structural unit represented by the above-mentioned formula (X), or may contain two or more types of structural units.
[0294] When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is, for example, 0.1 to 99.99 mol % relative to the total content of the structural units contained in the polymer compound (I). Since the driving voltage of the light-emitting device using the composition of this embodiment is lower, the content is preferably 1 to 99.9 mol %, more preferably 10 to 99.5 mol %, even more preferably 30 to 99 mol %, particularly preferably 50 to 95 mol %, and especially preferably 70 to 90 mol %. When the polymer compound (I) contains the structural unit (A) and the structural unit represented by the above-mentioned formula (Y), the polymer compound (I) may contain only one type of structural unit represented by formula (Y), or may contain two or more types of structural units represented by formula (Y).
[0295] When the polymer compound (I) contains a structural unit represented by formula (X) and / or a structural unit represented by formula (Y), and the structural unit (A), the total content of the structural unit represented by formula (X), the structural unit represented by formula (Y), and the structural unit (A) may be within a range that allows the polymer compound (I) to exhibit its functions. When the polymer compound (I) contains a structural unit represented by formula (X) and / or a structural unit represented by formula (Y), and the structural unit (A), the total content of the structural unit represented by formula (X), the structural unit represented by formula (Y), and the structural unit (A) relative to the total content of the structural units contained in the polymer compound (I) is, for example, 1 to 100 mol %. Because this results in excellent hole transport properties for the polymer compound (I) and a lower driving voltage for a light-emitting device using the composition of this embodiment, the total content is preferably 10 to 100 mol %, more preferably 30 to 100 mol %, even more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, and especially preferably 90 to 100 mol %. When the polymer compound (I) contains the structural unit represented by the above formula (X) and / or the structural unit represented by the above formula (Y), and the structural unit (A), the polymer compound (I) may contain only one type of structural unit represented by formula (X) and / or the structural unit represented by formula (Y), or may contain two or more types of structural units represented by formula (X) and / or formula (Y).
[0296] ·Constituent unit (B) The structural unit (B) is a structural unit having a group in which one or more hydrogen atoms have been removed from the low molecular weight compound (B). When the polymer compound (I) contains a structural unit (B), the structural unit (B) is preferably a structural unit having a group obtained by removing from the low molecular weight compound (B) at least one and at most five hydrogen atoms, more preferably a structural unit having a group obtained by removing from the low molecular weight compound (B) at least one and at most three hydrogen atoms, and even more preferably a structural unit having a group obtained by removing from the low molecular weight compound (B) at least one hydrogen atom, and even more preferably a structural unit having a group obtained by removing from the low molecular weight compound (B) at least one hydrogen atom. When the polymer compound (I) contains the structural unit (B), the structural unit (B) is preferably a structural unit represented by formula (BP-1), formula (BP-2) or formula (BP-3), and more preferably a structural unit represented by formula (BP-1) or formula (BP-2), because this facilitates synthesis of the polymer compound (I) and reduces the driving voltage of a light-emitting device using the composition of this embodiment. It is a unit of composition.
[0297] [ka]
[0298] [In the formula, M BP1 represents a group obtained by removing one hydrogen atom from the low molecular weight compound (B). M BP2 represents a group obtained by removing two hydrogen atoms from the low molecular weight compound (B). M BP3 represents a group obtained by removing three hydrogen atoms from the low molecular weight compound (B). L BP1 are each independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R BP1 )-, an oxygen atom, or a sulfur atom, and these groups may have a substituent. When a plurality of such substituents are present, 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. R BP1 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. When a plurality of such substituents are present, 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. L BP1 When there are a plurality of groups, they may be the same or different. n BP1 represents an integer between 0 and 10. Ar BP1represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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.
[0299] L BP1 is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, more preferably an alkylene group or an arylene group, and even more preferably an arylene group, and these groups may have a substituent. L BP1 Examples and preferred ranges of the arylene group and the divalent heterocyclic group in Y1 The examples and preferred ranges of the arylene group and divalent heterocyclic group are the same as those in the above. L BP1 The alkylene group in the formula (I) is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent. R BP1 Examples and preferred ranges of R X1 ~R X3 The examples and preferred ranges are the same as those of the above.
[0300] n BP1 is preferably an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0.
[0301] Ar BP1 Examples of the hydrocarbon group in Ar include an aromatic hydrocarbon group which may have a substituent and an aliphatic hydrocarbon group which may have a substituent. BP1 The hydrocarbon group in the formula (I) includes groups in which a plurality of these groups are bonded.
[0302] Ar BP1 In the above, the aliphatic hydrocarbon group is an alkylene group or a cycloalkylene group. Hydrogen atom n from the group BP1 Preferably, the alkylene group is a group obtained by removing n hydrogen atoms.BP1 These groups may have a substituent. Examples and preferred ranges of the alkylene group include a methylene group, an ethylene group, and a propylene group, and more preferably a methylene group. These groups may have a substituent.
[0303] Ar BP1 In the above, the aromatic hydrocarbon group is a group having n hydrogen atoms from an arylene group. BP1 Examples of the arylene group and a preferred range thereof include Ar Y1 Examples of the arylene group and preferred ranges thereof are as follows:
[0304] Ar BP1 As the heterocyclic group in BP1 Examples of the divalent heterocyclic group and a preferred range thereof include Ar Y1 Examples of the divalent heterocyclic group and preferred ranges thereof are as follows:
[0305] L BP1 and Ar BP1 Examples of the substituents that may be substituted by Ar Y1 The examples and preferred ranges of the substituents that may be possessed by the group represented by the formula:
[0306] Examples of the structural unit (B) include structural units represented by the following formula:
[0307] [ka]
[0308] [ka]
[0309] [In the formula, R TSis a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may further have a substituent. TS may be the same or different.]
[0310] R TS Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in Y1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by the following formula may have. R TS Examples of the substituents that may be possessed by Ar and their preferred ranges are Y1 The examples and preferred ranges of the substituents that the group represented by the following formula may have are the same as those of the substituents that the group may further have.
[0311] When the polymer compound (I) contains the structural unit (B), the polymer compound (I) preferably further contains at least one structural unit selected from the group consisting of the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y), because this reduces the driving voltage of a light-emitting device using the composition of this embodiment. That is, when the polymer compound (I) contains the structural unit (B), the polymer compound (I) is preferably a polymer compound that contains the structural unit (B) and at least one structural unit selected from the group consisting of the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y). When the polymer compound (I) contains at least one structural unit selected from the group consisting of structural units represented by the aforementioned formula (X) and structural units represented by the aforementioned formula (Y), and structural unit (B), it is preferable that structural unit (B) is different from the structural unit represented by the aforementioned formula (X) and the structural unit represented by the aforementioned formula (Y).
[0312] When the polymer compound (I) contains the structural unit (B), it is preferable that the polymer compound (I) further contains a structural unit represented by the above-mentioned formula (X), because this will result in excellent hole transport properties of the polymer compound (I) and a lower driving voltage for a light-emitting device using the composition of this embodiment. When the polymer compound (I) contains the structural unit (B), it is preferable that the polymer compound (I) further contains a structural unit represented by the above-mentioned formula (Y), since this will result in a lower driving voltage for a light-emitting device using the composition of this embodiment. When the polymer compound (I) contains the structural unit (B), the polymer compound (I) preferably further contains a structural unit represented by the above formula (X) and a structural unit represented by the above formula (Y), because this will result in excellent hole transport properties of the polymer compound (I) and a light-emitting element using the composition of the present embodiment with a further reduced driving voltage.
[0313] When the polymer compound (I) contains the structural unit (B) and the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains the structural unit (B) and the structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) relative to the total content of the structural units contained in the polymer compound (I) is, for example, 0.01 to 99.9 mol %. Since the hole transport properties of the polymer compound (I) are excellent and the driving voltage of the light-emitting device using the composition of this embodiment is lower, the content is preferably 0.05 to 90 mol %, more preferably 0.1 to 70 mol %, even more preferably 0.2 to 50 mol %, particularly preferably 0.5 to 30 mol %, and particularly preferably 1 to 10 mol %. When the polymer compound (I) contains the structural unit (B), the structural unit represented by the above formula (X) may contain only one type, or two or more types, of the structural unit.
[0314] When the polymer compound (I) contains the structural unit (B) and the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains the structural unit (B) and the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is, for example, 1 to 99.99 mol % relative to the total content of the structural units contained in the polymer compound (I). Since this reduces the driving voltage of a light-emitting device using the composition of this embodiment, the content is preferably 10 to 99.95 mol %, more preferably 30 to 99.9 mol %, even more preferably 50 to 99.8 mol %, particularly preferably 70 to 99.5 mol %, and especially preferably 90 to 99 mol %. When the polymer compound (I) contains the structural unit (B), the structural unit represented by the above formula (Y) may contain only one type, or two or more types, of structural units.
[0315] When the polymer compound (I) contains a structural unit represented by the aforementioned formula (X) and / or a structural unit represented by the aforementioned formula (Y), and the structural unit (B), the total content of the structural unit represented by the aforementioned formula (X), the structural unit represented by the aforementioned formula (Y), and the structural unit (B) may be within a range in which the polymer compound (I) can exhibit its functions. When the polymer compound (I) contains a structural unit represented by the above formula (X) and / or a structural unit represented by the above formula (Y), and the structural unit (B), the total content of the structural unit represented by the above formula (X), the structural unit represented by the above formula (Y), and the structural unit (B) relative to the total content of the structural units contained in the polymer compound (I) is, for example, 1 to 100 mol %. Because this results in excellent hole transport properties for the polymer compound (I) and a lower driving voltage for a light-emitting device using the composition of this embodiment, the total content is preferably 10 to 100 mol %, more preferably 30 to 100 mol %, even more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, and particularly preferably 90 to 100 mol %. When the polymer compound (I) contains a structural unit represented by the above formula (X) and / or a structural unit represented by the above formula (Y), and the structural unit (B), the polymer compound (I) may contain only one type of structural unit represented by the above formula (X) and / or the above structural unit represented by the above formula (Y), or may contain two or more types of structural units represented by the above formula (X) and / or the above structural unit represented by the above formula (Y).
[0316] When the polymer compound (I) contains the structural unit represented by the formula (X) and / or the structural unit represented by the formula (Y), and the structural unit (A) and the structural unit (B), In this case, the total content of the structural unit represented by formula (X), the structural unit represented by formula (Y), the structural unit (A), and the structural unit (B) may be within a range that allows the polymer compound (I) to function. When the polymer compound (I) contains the structural unit represented by formula (X) and / or the structural unit represented by formula (Y), and the structural unit (A) and the structural unit (B), the total content of the structural unit represented by formula (X), the structural unit represented by formula (Y), the structural unit (A), and the structural unit (B) is, for example, 1 to 100 mol% relative to the total content of the structural units contained in the polymer compound (I). Since the hole transport properties of the polymer compound (I) are excellent and the driving voltage of a light-emitting device using the composition of this embodiment is lower, the total content is preferably 10 to 100 mol%, more preferably 30 to 100 mol%, even more preferably 50 to 100 mol%, particularly preferably 70 to 100 mol%, and particularly preferably 90 to 100 mol%. When the polymer compound (I) contains the structural unit represented by the above formula (X) and / or the structural unit represented by the above formula (Y), as well as the structural unit (A) and the structural unit (B), the polymer compound (I) may contain only one type of structural unit represented by the above formula (X) and / or the structural unit represented by the above formula (Y), or may contain two or more types of structural units.
[0317] Examples of polymer compound (I) include polymer compounds HP-1 to HP-3, AP-1 to AP-4, BP-1 to BP-4, and CP-1 to CP-4. Here, "other" refers to structural units other than the structural unit represented by formula (X), the structural unit represented by formula (Y), the structural unit (A), and the structural unit (B).
[0318] [Table 1]
[0319] [In the table, p, q, r, s, and t represent the molar ratio (mol %) of each structural unit. p+q+r+s+t=100, and 70≦p+q+r+s≦100.]
[0320] The polymer compound (I) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, but is preferably a copolymer obtained by copolymerizing a plurality of raw material monomers.
[0321] The polymer compound 1 has a large weight-average molecular weight, and the polymerization reaction takes a long time. When the polymer compound 1 contains the structural unit (A) or the structural unit (B), the structural unit (A) and the structural unit (B) are likely to chemically deteriorate due to side reactions in the polymerization reaction. Therefore, it is preferable that the polymer compound 1 does not have the structural unit (A) or the structural unit (B). In other words, it is preferable that the polymer compound 1 consists only of the structural unit represented by the aforementioned formula (X) and / or the structural unit represented by the aforementioned formula (Y). Preferably, it is composed solely of constitutional units represented by formula (Y), and even more preferably it is composed solely of constitutional units represented by formula (Y-1) or formula (Y-2).
[0322] The weight average molecular weight of the polymer compound 1 in terms of polystyrene is preferably 2.0×10 5 ~1.0×10 6 and more preferably 2.8 × 10 5 ~1.0×10 6 and more preferably 2.8 × 10 5~8.0×10 5 and particularly preferably 2.8 × 10 5 ~6.0×10 5 is.
[0323] Since the polymer compound 2 has a small weight-average molecular weight and does not require long-term polymerization, it may have the structural unit (A) and / or the structural unit (B), but it is preferable that it does not have the structural unit (A) and the structural unit (B). That is, the polymer compound 2 preferably consists only of the structural unit represented by the above formula (X) and / or the structural unit represented by the above formula (Y), and the formula It is more preferable that the polymer compound 2 consists only of structural units represented by (Y). Furthermore, the polymer compound 2 may differ from the polymer compound 1 in some or all of the types of structural units, or in the composition ratio of the structural units.
[0324] The weight average molecular weight of the polymer compound 2 in terms of polystyrene is preferably 1.0×10 4 Over 2.0 x 10 5 and more preferably less than 1.0 × 10 4 Over 1.5 x 10 5 and more preferably 1.0 × 10 4 Over 1.1 x 10 5 It is particularly preferably 1.0 × 10 4 Over 1.0 x 10 5 The following is the result.
[0325] (Method for producing polymer compound (I)) The polymer compound (I) can be produced by a known polymerization method described in, for example, Chem. Rev., Vol. 109, pp. 897-1091 (2009), and examples thereof include polymerization methods by coupling reactions using transition metal catalysts, such as Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction, and Kumada reaction.
[0326] In the above polymerization method, examples of the method for charging the monomers include a method in which the entire amount of the monomers is charged into the reaction system all at once, a method in which a part of the monomers is charged and reacted, and then the remaining monomers are charged all at once, continuously or in portions, and a method in which the monomers are charged continuously or in portions. Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst. Post-treatment of the polymerization reaction can be carried out by any of known methods, such as removing water-soluble impurities by liquid separation, or adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying it, either alone or in combination. When the purity of the polymer compound (I) is low, it can be purified by a conventional method such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, or column chromatography.
[0327] (solvent) The composition of the present embodiment includes a solvent (A) that satisfies at least one of the requirements (i) and (ii). The solvent (A) is a compound selected from the group consisting of a phosphorescent compound and a low-molecular-weight compound (B). The solvent is preferably a solvent that can dissolve at least one selected from the group consisting of polymer compound 1 and polymer compound 2, and does not react with these compounds in the composition. In addition, solvent (A) is preferably a solvent that satisfies requirement (i), and more preferably a solvent that satisfies both requirements (i) and (ii), since it can more effectively stabilize the inkjet ejection of polymer compound 1.
[0328] The composition of this embodiment may contain, in addition to the solvent (A), another solvent (B) that does not satisfy either requirement (i) or requirement (ii). The solvent (A) may be used alone or in combination of two or more. The other solvent (B) may be used alone or in combination of two or more. When a mixed solvent of two or more solvents (A) or a mixed solvent of one or more solvents (A) and one or more other solvents (B) is used as the solvent, the boiling point at 1 atmosphere of each solvent or mixed solvent is preferably 60 to 280°C, more preferably 80 to 280°C, so that evaporation of the solvent during storage of the composition can be suppressed and the solvent can be suppressed from remaining in the film described below. More preferably, the boiling point of at least one solvent is 180 to 280°C.
[0329] The content of solvent (A) in the solvent contained in the composition of this embodiment is preferably 50 to 100% by mass, more preferably 60 to 90% by mass, and even more preferably 70 to 80% by mass, since this can improve the inkjet properties of the composition of this embodiment.
[0330] The solvent contained in the composition of the present embodiment is preferably a liquid at 25° C. and 1 atmosphere. Examples of the solvent (A) and the other solvent (B) include aromatic hydrocarbons, aromatic ethers, aliphatic hydrocarbons, aliphatic ethers, alcohols, ketones, amides, esters, and carbonates.
[0331] The aromatic hydrocarbon is preferably benzene having 8 to 14 carbon atoms per molecule and having 1 to 3 substituents. The substituent is preferably a linear or branched unsubstituted alkyl group having 1 to 8 carbon atoms, a cyclopentyl group, a methylcyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a cycloheptyl group, or a methylcycloheptyl group. The alkyl groups may be bonded to each other to form a ring. Such compounds have a boiling point within a preferred range, and the phosphorescent compound, low molecular weight compound (B), polymer compound 1, and polymer compound 2, which are solid at 25°C and 1 atmospheric pressure, have good solubility. Specific examples of preferable aromatic hydrocarbons include toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, n-propylbenzene, cumene, n-butylbenzene, tert-butylbenzene, n-pentylbenzene, cyclopentylbenzene, 2-methylcyclopentylbenzene, 3-methylcyclopentylbenzene, n-hexylbenzene, cyclohexylbenzene, 2-methylcyclohexylbenzene, 3-methylcyclohexylbenzene, 4-methylcyclohexylbenzene, n-heptylbenzene, cycloheptylbenzene, 2-methylcycloheptylbenzene, 3-methylcycloheptylbenzene, 4-methylcycloheptylbenzene, n-octylbenzene, and tetralin. Among aromatic hydrocarbons, aromatic carbon rings such as toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, tetramethylbenzene, n-propylbenzene, cumene, n-butylbenzene, n-pentylbenzene, cyclopentylbenzene, n-hexylbenzene, cyclohexylbenzene, n-heptylbenzene, n-octylbenzene, and tetralin, and compounds containing a carbon atom directly bonded to an aromatic carbon ring and having a hydrogen atom bonded to the carbon atom, are preferred.
[0332] Aromatic ethers have 7 to 12 carbon atoms in one molecule, and those with 4 or less carbon atoms Ethers in which a phenyl group, which may be substituted with an unsubstituted alkyl group, and an unsubstituted alkyl group having 4 or less carbon atoms are bonded via an ether bond are preferred. Such compounds have a boiling point within a preferred range and exhibit excellent solubility for phosphorescent compounds. Specific examples of preferred aromatic ethers include anisole, ethoxybenzene, 1-propoxybenzene, 2-propoxybenzene, 1-butoxybenzene, 2-butoxybenzene, (2-methyl)propoxybenzene, tert-butoxybenzene, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2-ethoxytoluene, 3-ethoxytoluene, and 4-ethoxytoluene. Specific examples of particularly preferred aromatic ethers include anisole, ethoxybenzene, 2-propoxybenzene, tert-butoxybenzene, 2-methoxytoluene, 3-methoxytoluene, and 4-methoxytoluene.
[0333] The aliphatic hydrocarbon preferably has a carbon number in one molecule in the range of 5 to 20. Of these, linear, branched, and cyclic saturated hydrocarbons are particularly preferred, and examples thereof include hexane, heptane, octane, nonane, decane, cyclopentane, methylcyclopentane, cyclohexane, methylcyclohexane, and bicyclohexyl.
[0334] The aliphatic ether is preferably an ether having 5 to 12 carbon atoms and 1 to 4 oxygen atoms in one molecule, and particularly preferably a linear, branched, or cyclic saturated aliphatic ether, such as diisopropyl ether, methyl tert-butyl ether, di-n-butyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, or triethylene glycol dimethyl ether.
[0335] The alcohol preferably has 2 to 15 carbon atoms in one molecule, such as ethanol, propanol, butanol, pentanol, cyclopentanol, hexanol, cyclohexanol, heptanol, octanol, benzyl alcohol, phenylethanol, ethylene glycol, propylene glycol, diethylene glycol monomethyl ether, propanediol, and glycerin.
[0336] The ketone is preferably a ketone having 3 to 12 carbon atoms in one molecule, and particularly preferably a ketone having no alkene or alkyne moiety. Examples thereof include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, 1-hexanone, 2-hexanone, 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, phenylacetone, acetylacetone, acetonylacetone, acetophenone, methyl naphthyl ketone, and isophorone.
[0337] Preferred amides include 1-methyl-2-pyrrolidone, 1-ethyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, and 1,3-dimethyl-2-imidazolidinone.
[0338] The ester is preferably an ester having 4 to 12 carbon atoms in one molecule, and examples thereof include butyl acetate, ethyl acetate, isopropyl acetate, pentyl acetate, isopentyl acetate, amyl acetate, ethyl propionate, ethyl butyrate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl-3-ethoxypyrobionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propyl formate, propyl lactate, ethyl phenylacetate, ethyl benzoate, β-propiolactone, γ-butyrolactone, and δ-valerolactone.
[0339] The carbonate is preferably a carbonate having 4 to 15 carbon atoms in one molecule, for example, Examples include dimethyl carbonate, diethyl carbonate, ethylene carbonate, and propylene carbonate.
[0340] The solvent is preferably an aromatic hydrocarbon, an aromatic ether, or a mixed solvent of an aromatic hydrocarbon and an aromatic ether, which can dissolve the polymer compound having an aryl moiety and the phosphorescent compound well.
[0341] The solvent is preferably purified before producing the composition. This purification process can remove oxides contained in the solvent, as well as antioxidants, light stabilizers, and other additives that are undesirable for light-emitting devices and that were added during the solvent production process or accidentally mixed in. Preferred purification methods include distillation, column purification using silica gel, alumina, ion exchange resin, activated carbon, or adsorption. The purified solvent is preferably stored in an additive-free resin container, a fluorine-based resin container, a glass container, a metal container, or the like. To prevent oxidation degradation during storage, the gas phase of the solvent container may be purged with an inert gas, or the solvent may be stored at a temperature of 25°C or below. An additive for preventing oxidation degradation may be added immediately after the purification process is completed. In this case, the amount of additive added is preferably 0.1 to 10,000 ppm relative to the mass of the solvent. During solvent storage, nitrogen substitution, low-temperature storage, and additive addition may be performed independently or in combination.
[0342] In the ink, the content of the solvent is usually 1,000 to 1,000,000 parts by mass, preferably 2,000 to 1,000,000 parts by mass, more preferably 3,500 to 100,000 parts by mass, and particularly preferably 5,000 to 10,000 parts by mass, where the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B) is taken as 100 parts by mass.
[0343] In the composition of this embodiment, the content of polymer compound 1 is typically 0.01 to 99 parts by mass, where the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B) is taken as 100 parts by mass. In order to further improve the inkjet dischargeability of the composition of this embodiment, the content of polymer compound 1 is preferably 0.05 to 50 parts by mass, more preferably 0.1 to 30 parts by mass, even more preferably 0.3 to 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass.
[0344] In the composition of this embodiment, the content of polymer compound 2 is typically 0.01 to 99 parts by mass, where the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B) is taken as 100 parts by mass. Since the driving voltage of a light-emitting device using the composition of this embodiment becomes lower, the content is preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, even more preferably 1 to 70 parts by mass, particularly preferably 5 to 60 parts by mass, and particularly preferably 10 to 50 parts by mass.
[0345] In the composition of this embodiment, the content of the phosphorescent compound may be in a range that allows the composition to function properly. In the composition of this embodiment, the content of the phosphorescent compound is, for example, 0.01 to 99 parts by mass, where the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B) is taken as 100 parts by mass. Since the driving voltage of a light-emitting device using the composition of this embodiment becomes lower, the content is preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, even more preferably 1 to 70 parts by mass, particularly preferably 5 to 50 parts by mass, and particularly preferably 10 to 30 parts by mass.
[0346] In the composition of this embodiment, the content of the low molecular weight compound (B) may be within a range in which the composition can exhibit its functions. In the composition of this embodiment, the content of the low molecular weight compound (B) is the same as that of the polymer compound 1. When the total content of the child compound 2, the phosphorescent compound, and the low molecular weight compound (B) is taken as 100 parts by mass, the content is, for example, 0.01 to 99 parts by mass. Since the driving voltage of the light-emitting device using the composition of this embodiment becomes lower, the content is preferably 0.01 to 90 parts by mass, more preferably 0.05 to 70 parts by mass, even more preferably 0.1 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, and especially preferably 1 to 25 parts by mass.
[0347] (antioxidant) The antioxidant may be any compound that is soluble in the same solvent as polymer compound 1, polymer compound 2, the phosphorescent compound, and low molecular weight compound (B) and does not inhibit light emission and charge transport, and examples of the antioxidant include phenol-based antioxidants and phosphorus-based antioxidants. When the composition of the present embodiment contains an antioxidant, the content of the antioxidant is usually 0.001 to 10 parts by mass, relative to 100 parts by mass of the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B). The antioxidants may be used alone or in combination of two or more.
[0348] (hole transport material) Hole transport materials are classified into low molecular weight compounds and high molecular weight compounds. The hole transport material may have a crosslinking group. Examples of low molecular weight compounds include aromatic amine compounds such as triphenylamine and its derivatives, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (α-NPD), and N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD).
[0349] Examples of the polymer compound include polyvinylcarbazole and its derivatives, and polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain. The polymer compound may also be a compound to which an electron-accepting moiety is bonded, such as fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone.
[0350] When the composition of the present embodiment contains a hole transport material, the content of the hole transport material is usually 1 to 1,000 parts by mass, relative to 100 parts by mass of the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B). The hole transport material may be used alone or in combination of two or more kinds.
[0351] (electron transport material) Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds. The electron transport material may have a crosslinking group.
[0352] Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, as well as derivatives thereof.
[0353] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.
[0354] When the composition of the present embodiment contains an electron transport material, the content of the electron transport material is usually 1 to 1,000 parts by mass, relative to 100 parts by mass of the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B). The electron transporting materials may be used alone or in combination of two or more.
[0355] (Hole injection material and electron injection material) The hole injection material and the electron injection material are each classified into a low molecular weight compound and a high molecular weight compound. The hole injection material and the electron injection material may have a crosslinking group.
[0356] 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.
[0357] Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, polyquinoxaline, and derivatives thereof; and conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain.
[0358] When the composition of the present embodiment contains a hole injection material and / or an electron injection material, the content of each of the hole injection material and the electron injection material is usually 1 to 1,000 parts by mass, relative to 100 parts by mass of the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B). The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.
[0359] Ion doping The hole injection material or electron injection material may be doped with ions. For example, when the hole injection material or electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1×10 S / cm to 1×10 S / cm. In order to adjust the electrical conductivity of the conductive polymer to fall within this range, the conductive polymer can be doped with an appropriate amount of ions.
[0360] The type of ion doped into the hole injection material or electron injection material may be, for example, an anion for the hole injection material, or a cation for the electron injection material. Examples of anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions. The doping ions may be used singly or in combination of two or more kinds.
[0361] (luminescent material) Light-emitting materials are classified into low molecular weight compounds and high molecular weight compounds. The light-emitting material may have a crosslinking group. Examples of low molecular weight compounds include naphthalene and its derivatives, anthracene and its derivatives, and perylene and its derivatives. Examples of the polymer compound include polymer compounds containing a constitutional unit represented by formula (Y) and / or a constitutional unit represented by formula (X).
[0362] (film) The film is a film formed using the composition of the present embodiment.
[0363] When the composition of the present embodiment contains a light-emitting material, the contents of the hole injection material and the electron injection material are each typically 1 to 1,000 parts by mass, relative to 100 parts by mass of the total content of polymer compound 1, polymer compound 2, phosphorescent compound, and low molecular weight compound (B). The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.
[0364] The film is suitable as a light-emitting layer in a light-emitting device.
[0365] The film can be produced using an ink by a wet method such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, or nozzle coating.
[0366] The thickness of the film is usually 1 nm to 10 μm.
[0367] (light-emitting element) The light-emitting device of this embodiment is a light-emitting device fabricated using the composition of this embodiment. The light-emitting device of this embodiment has, for example, electrodes consisting of an anode and a cathode, and a layer formed using the composition of this embodiment between the electrodes.
[0368] The layer formed using the composition of this embodiment is typically one or more layers selected from the group consisting of a light-emitting layer, a hole-transport layer, a hole-injection layer, an electron-transport layer, and an electron-injection layer, and is preferably a light-emitting layer. These layers each contain a light-emitting material, a hole-transport material, a hole-injection material, an electron-transport material, and an electron-injection material. These layers can be formed using the same method as for producing the above-mentioned film, by dissolving the light-emitting material, hole-transport material, hole-injection material, electron-transport material, and electron-injection material in the above-mentioned solvent to prepare an ink.
[0369] The light-emitting element has a light-emitting layer between an anode and a cathode. From the viewpoint of hole injection and hole transport properties, the light-emitting element of this embodiment preferably has at least one hole injection layer and hole transport layer between the anode and the light-emitting layer, and from the viewpoint of electron injection and electron transport properties, preferably has at least one electron injection layer and electron transport layer between the cathode and the light-emitting layer.
[0370] Examples of materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer, and electron injection layer include the composition of this embodiment as well as the hole transport material, electron transport material, light-emitting material, hole injection material, and electron injection material described above, respectively.
[0371] When the materials for the hole transport layer, electron transport layer, and light-emitting layer are soluble in a solvent used to form the hole transport layer, electron transport layer, and layer adjacent to the light-emitting layer in the fabrication of a light-emitting device, the materials preferably have a crosslinking group to prevent the materials from dissolving in the solvent. After forming each layer using a material having a crosslinking group, the layer can be made insoluble by crosslinking the crosslinking group.
[0372] In the light-emitting element of this embodiment, examples of methods for forming each layer, such as the light-emitting layer, hole transport layer, electron transport layer, hole injection layer, and electron injection layer, include, when a low-molecular-weight compound is used, a vacuum deposition method from a powder, and a method of film formation from a solution or molten state; and when a high-molecular-weight compound is used, examples of methods for film formation from a solution or molten state are used.
[0373] The order, number and thickness of the layers to be stacked are adjusted taking into consideration the external quantum efficiency and luminance life.
[0374] The substrate in the light-emitting element may be any substrate on which electrodes can be formed and which is not chemically changed when an organic layer is formed, such as a substrate made of a material such as glass, plastic, silicon, etc. In the case of an opaque substrate, it is preferable that the electrode farthest from the substrate is transparent or translucent.
[0375] Examples of materials for the anode include conductive metal oxides and translucent metals, and preferred are indium oxide, zinc oxide, and tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, and copper.
[0376] Cathode materials include, for example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these; alloys of one or more of these with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of alloys include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The anode and cathode may each have a laminated structure of two or more layers.
[0377] The light-emitting device of this embodiment is useful for applications such as displays and lighting. [Example]
[0378] Hereinafter, one embodiment of the present disclosure will be described in more detail with reference to examples, but the present disclosure is not limited to these examples.
[0379] In the examples, the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound was determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. The SEC measurement conditions were as follows: The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL of the solution was injected into the SEC. The mobile phase was run at a flow rate of 2.0 mL / min. The column used was a PLgel MIXED-B (manufactured by Polymer Laboratories). The detector used was a UV-VIS detector (manufactured by Shimadzu Corporation, product name: SPD-10Avp).
[0380] <Synthesis of Compounds S1 to S4> Compounds S1 and S4 were synthesized according to the method described in JP-A-2010-189630. Compound S2 was synthesized according to the method described in WO 2015 / 008851. Compound S3 was synthesized according to the method described in WO 2012 / 086671.
[0381] [ka]
[0382] <Synthesis of polymer compounds P1 and P2> Polymer compound P1 and polymer compound P2 were synthesized according to the method described in WO 2013 / 191088.
[0383] [Table 2]
[0384] <Synthesis of polymer compound P3> Polymer compound P3 was synthesized according to the method described in JP-A-2012-036388.
[0385] [Table 3]
[0386] <Synthesis of polymer compound P4> Polymer compound P4 was synthesized according to the method described in JP 2019-195057 A.
[0387] [Table 4]
[0388] <Synthesis of metal complex MC1> Metal complex MC1 was synthesized according to the method described in WO 2009 / 131255.
[0389] [ka]
[0390] Example 1 Preparation and Evaluation of Composition 1 (Preparation of solvent 1) Solvent 1 was prepared by mixing cyclohexylbenzene (boiling point 236° C.) and xylene (boiling point 140° C.) in a ratio of xylene / cyclohexylbenzene=70% by mass / 30% by mass.
[0391] (Preparation of Composition 1) Composition 1 was prepared by dissolving polymer compound P1, polymer compound P3, and metal complex MC1 (polymer compound P1 / polymer compound P3 / metal complex MC1 = 3% by mass / 50% by mass / 47% by mass) in solvent 1 at a concentration of 2.0% by mass.
[0392] (Evaluation of ejection properties) The inkjet ejection properties were evaluated by observing the ink ejection state using a FUJIFILM Dimatix droplet observation device DMP-2831 (Samba 3pL (LCP) cartridge box) under ejection conditions of a head temperature of 28°C and a frequency of 1 kHz using stroboscopic photography. If the droplets coalesced without splitting and flew at a position 800 μm from the nozzle, it was marked as ◯, and if this did not apply, it was marked as ×.
[0393] Example 2 Preparation and Evaluation of Composition 2 Composition 2 was prepared in the same manner as in Example 1 (preparation of composition 1), except that "polymer compound P4" was used instead of "polymer compound P3". The ejection properties were evaluated in the same manner as in Example 1 (evaluation of ejection properties), except that "Composition 2" was used instead of "Composition 1".
[0394] Comparative Example 1: Preparation and evaluation of composition 5 Composition 5 was prepared in the same manner as in Example 1 (preparation of composition 1), except that "polymer compound P4" was used instead of "polymer compound P1". The ejection properties were evaluated in the same manner as in Example 1 (evaluation of ejection properties), except that "Composition 5" was used instead of "Composition 1".
[0395] Comparative Example 2: Preparation and evaluation of composition 6 Composition 6 was prepared in the same manner as in Example 1 (preparation of composition 1), except that "xylene" was used instead of "solvent 1" in Example 1. In Example 1 (evaluation of ejection properties), "Composition 6" was used instead of "Composition 1". The dischargeability was evaluated in the same manner as in Example 1 except for the above.
[0396] Comparative Example 3: Preparation and evaluation of composition 7 Composition 7 was prepared by dissolving polymer compound P2, polymer compound P4, and metal complex MC1 (polymer compound P2 / polymer compound P4 / metal complex MC1 = 3% by mass / 50% by mass / 47% by mass) in xylene at a concentration of 2.0% by mass. The ejection properties were evaluated in the same manner as in Example 1 (evaluation of ejection properties), except that "Composition 7" was used instead of "Composition 1".
[0397] [Table 5]
[0398] As is clear from Table 5, the weight average molecular weight of polymer compound 1 in terms of polystyrene is 2.0 × 10 5 The composition in which the weight average molecular weight of the polymer compound 1 in terms of polystyrene is 2.0 × 10 5 It can be seen that the ejection properties are superior to those of the comparative compositions containing compositions having a viscosity of less than 1000 MPa.
[0399] As is clear from Table 5, the composition containing a solvent with a boiling point of 200°C or higher has superior ejection properties compared to the comparative composition containing a composition that does not contain a solvent with a boiling point of 200°C or higher.
Claims
1. at least one compound selected from the group consisting of a phosphorescent compound and a low molecular weight compound (B); Polymer compound 1, Polymer compound 2, A solvent; A composition comprising: The low molecular weight compound (B) contains a boron atom, an oxygen atom, a sulfur atom, a selenium atom, sp 3 a low molecular weight compound having a fused heterocyclic skeleton (b) containing at least one atom selected from the group consisting of a carbon atom and a nitrogen atom in the ring, The polymer compound 1 includes at least one of a structural unit represented by formula (X), a structural unit represented by formula (Y), a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B), and a structural unit having a group obtained by removing one or more hydrogen atoms from the phosphorescent compound, and has a weight-average molecular weight in terms of polystyrene of 2.0 × 10 5 The polymer compound is as described above. The polymer compound 2 includes at least one of a structural unit represented by formula (X), a structural unit represented by formula (Y), a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B), and a structural unit having a group obtained by removing one or more hydrogen atoms from the phosphorescent compound, and has a weight-average molecular weight in terms of polystyrene of 2.0 × 10 5 a polymer compound having a molecular weight of less than The composition, wherein the solvent satisfies at least one of requirements (i) and (ii). (i) The boiling point is 200°C or higher. (ii) has a cycloalkyl group; 【Chemistry 1】 [In the formula, a X1 and a X2 each independently represents an integer of 0 or more. Ar X1 and Ar X3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, 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. Ar X2 and Ar X4 each independently 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 groups may have a substituent. When a plurality of such substituents are present, 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. X2 When a plurality of Ar are present, they may be the same or different. X4 When there are a plurality of groups, they may be the same or different. R X1 , R X2 and R X3 R each independently 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. When a plurality of such substituents are present, 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. X2 When there are a plurality of R, they may be the same or different. X3 When there are multiple groups, they may be the same or different. 【Chemistry 2】 [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 to each other, and these groups may have a substituent. When a plurality of such substituents are present, 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.]
2. The composition according to claim 1 , wherein the polymer compound 1 consists solely of a constitutional unit represented by formula (Y):
3. 2. The composition according to claim 1, wherein the polymer compound 1 consists solely of a constitutional unit represented by formula (Y-1) or formula (Y-2). 【Transformation 3】 [In the formula, R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, 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. Y1 may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. X Y1 is -C(R Y2 ) 2 -, -C(R Y2 ) = C(R Y2 ) - or -C(R Y2 ) 2 -C(R Y2 ) 2 represents a group represented by -. Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, and these groups may have a substituent. When there are multiple such substituents, 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. Y2 may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
4. The composition according to claim 1 , wherein the polymer compound 2 comprises a constitutional unit represented by formula (Z): 【Chemistry 4】 [In the formula, Ar Z represents a divalent heterocyclic group having a group represented by -N= within the ring, and the group may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ar Z1 and Ar Z2 Each of Ar independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Z1 When a plurality of Ar are present, they may be the same or different. Z2 When there are multiple groups, they may be the same or different. n Z1 and n Z2 each independently represents an integer of 0 or more and 5 or less.
5. The composition of claim 1 , wherein the phosphorescent compound is represented by formula (M): 【Transformation 5】 [In the formula, M 1 represents an iridium atom or a platinum atom. n M1 represents an integer of 1 or more, and n M2 represents an integer of 0 or more. 1 When is an iridium atom, n M1 +n M2 is 3, and M 1 When is a platinum atom, n M1 +n M2 is 2. E 1 and E 2 each independently represents a carbon atom or a nitrogen atom. 1 and E 2 At least one of the groups is a carbon atom. Ring R M1 represents an aromatic heterocycle, and this ring may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R M1 When there are multiple groups, they may be the same or different. Ring R M2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring R M2 When there are multiple groups, they may be the same or different. Ring R M1 and the substituents which may be present on the ring R M2 The substituents which may be possessed by the group may be bonded to each other to form a ring together with the atoms to which they are bonded. -A D1 ---A D2 - represents an anionic bidentate ligand. D1 and A D2 are each independently, M 1 represents a carbon atom, an oxygen atom, or a nitrogen atom bonded to the atom, and these atoms may be atoms constituting a ring. D1 ---A D2 If there are multiple -s, may be the same or different.]
6. Hole transport materials, hole injection materials, electron transport materials, electron injection materials, light emitting materials (excluding those corresponding to the phosphorescent compounds described above).
2. The composition according to claim 1, further comprising at least one selected from the group consisting of an antioxidant and an anti-oxidant.
7. A light-emitting device comprising the composition according to any one of claims 1 to 6.
Citation Information
Patent Citations
Composition, method for preparing film, and functional element and method for preparing the same
WO2000059267A1