Composition and light-emitting element using the same
A polymer compound composition with boron and heteroatoms improves the external quantum efficiency of light-emitting devices, addressing inefficiencies in existing technologies and facilitating better device performance.
Patent Information
- Application Number
- JP2023210432
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-12-13
- Publication Date
- 2025-06-25
AI Technical Summary
There is room for improvement in the external quantum efficiency of existing light-emitting devices, particularly those using certain polymer compositions.
A composition containing two or more polymer compounds, at least one of which includes a boron atom and other heteroatoms like oxygen, sulfur, or selenium, with specific molecular weight and side chain carbon atom ratios, is used to enhance the external quantum efficiency of light-emitting devices.
The proposed composition leads to the development of light-emitting devices with improved external quantum efficiency, facilitating easier production and enhancing performance.
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Abstract
Description
Technical Field
[0001] The present invention relates to a composition and a light-emitting device using the same.
Background Art
[0002] Light-emitting devices such as organic electroluminescence devices can be suitably used, for example, in displays and lighting. As a light-emitting material used in the light-emitting layer of a light-emitting device, for example, Patent Document 1 discloses a composition containing a polymer compound including a structural unit B0. Further, for example, Patent Document 2 discloses a composition containing a polymer compound including a structural unit B0.
[0003]
Chemical Formula
Prior Art Documents
Patent Documents
[0004]
Patent Document 1
Patent Document 2
Summary of the Invention
Problems to be Solved by the Invention
[0005] However, there is room for improvement in the external quantum efficiency of the light-emitting device manufactured using the above composition. Therefore, an object of the present invention is to provide a composition useful for manufacturing a light-emitting device having excellent external quantum efficiency.
Means for Solving the Problems
[0006] The present invention provides the following [1] to
[12] .
[0007] [1] A composition containing two or more polymer compounds, Among the two or more polymer compounds, at least one is a polymer compound (B), The polymer compound (B) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, sp 3 A polymer compound containing a structural unit (B) having a group obtained by removing one or more hydrogen atoms from a low molecular compound (B) having a condensed heterocyclic skeleton (b) containing at least one selected from the group consisting of a carbon atom and a nitrogen atom in the ring, Let the ratio of the content of each polymer compound contained in the composition to the total content of all polymer compounds contained in the composition be W1, let the total molecular weight of all structural units constituting each polymer compound be M1, and let the sp 2 Total number of carbon atoms of the side chains possessed by all structural units constituting each polymer compound be C sp2 When it is set, the sum X of the values of (W1 × C sp2 × 1000) / M1 for each polymer compound sp2 Is 15 or less, for example 0 or more and 15 or less, 1 or more and 15 or less, 2 or more and 15 or less, 3 or more and 15 or less, preferably 5 or more and 15 or less, more preferably 7 or more and 14.8 or less, still more preferably 9 or more and 14.6 or less, particularly preferably 10 or more and 14.5 or less, said composition.
[0008] [2] Among the two or more polymer compounds, at least one is a polymer compound (A), The composition according to [1], wherein the polymer compound (A) is a polymer compound containing at least one structural unit selected from the group consisting of a structural unit represented by formula (Y) and a structural unit represented by formula (X).
[0009]
Chemical formula
[0010] [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 substituents. When there are a plurality of these 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 respectively bonded.
[0011]
Chemical formula
[0012] [In the formula, a X1 and a X2 each independently represent an integer of 0 or more. Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have substituents. When there are a plurality of these 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 respectively bonded. Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have substituents. When there are a plurality of these 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 respectively bonded. Ar X2 When there are a plurality of them, they may be the same or different from each other. Ar X4 When there are a plurality of them, they may be the same or different from each other. R X1 , R X2 and R X3each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have substituents. When a plurality of these 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 respectively bonded. R X2 When a plurality of R X3 are present, they may be the same or different.]
[0013] [3] The composition according to [1] or [2], wherein the condensed heterocyclic skeleton (b) contains in the ring at least one selected from the group consisting of a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom.
[0014] [4] The composition according to [3], wherein the condensed heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.
[0015] [5] The composition according to any one of [1] to [4], wherein the low molecular weight compound (B) is a compound represented by formula (1-1), a compound represented by formula (1-2) or a compound represented by formula (1-3).
[0016]
Chemical formula
[0017] [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 substituents. When a plurality of these 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 respectively bonded. Y 1represents 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 substituents. 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 respectively bonded. Y 2 and Y 3 each independently represents 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 substituents. 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 respectively 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 substituents. 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 respectively bonded. When there are a plurality of Ry, they may be the same or different. Y 1 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. Y 1 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. Y 2 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. Y 2 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring. Y 3 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. Y 3 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring.]
[0018] [6] Said Y1 and the Y 2 and the Y 3 are a group represented by an oxygen atom, a sulfur atom or -N(Ry)-, the composition according to [5].
[0019] [7] the Y 1 and the Y 2 and the Y 3 are a group represented by -N(Ry)-, the composition according to [6].
[0020] [8] The structural unit (B) is a structural unit represented by formula (BP-1), a structural unit represented by formula (BP-2) or a structural unit represented by formula (BP-3), the composition according to any one of [1] to [7].
[0021]
Chemical formula
[0022] [In the formula, M BP1 represents a group obtained by removing one hydrogen atom from the low molecular compound (B). M BP2 represents a group obtained by removing two hydrogen atoms from the low molecular compound (B). M BP3 represents a group obtained by removing three hydrogen atoms from the low molecular compound (B). M BP1 , M BP2 , and M BP3 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 respectively bonded. L BP1 are each independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R BP1represents a group represented by [])-, an oxygen atom or a sulfur atom, and these groups may have substituents. When a plurality of these 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 respectively 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 substituents. When a plurality of these 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 respectively bonded. L BP1 When a plurality of Ls are present, they may be the same or different from each other. n BP1 represents an integer of 0 or more and 10 or less. Ar BP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have substituents. When a plurality of these 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 respectively bonded.]
[0023] [9] The composition according to any one of [1] to [8], wherein the polymer compound (B) further contains at least one structural unit selected from the group consisting of a structural unit represented by the formula (Y) and a structural unit represented by the formula (X).
Chemical formula
[0024] [In the formula, Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have substituents. When a plurality of these 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 respectively bonded.]
[0025]
Chemical formula
[0026] [wherein, 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 substituents. When a plurality of these 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 each 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 substituents. When a plurality of these 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 each bonded. When a plurality of Ar X2 are present, they may be the same or different from each other. When a plurality of Ar X4 are present, they may be the same or different from each other. R X1 R X2 and R X3 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 substituents. When a plurality of these 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 each bonded. When a plurality of R X2 are present, they may be the same or different from each other. When a plurality of R X3 are present, they may be the same or different from each other.]
[0027]
[10] The total number of sp 3 carbon atoms in the side chains possessed by all the constituent units constituting each of the above polymer compounds is C sp3 and (W1 × C sp3The sum of the values of (×1000) / M1 is X sp3 When X sp2 / X sp3 is less than 0.55, preferably 0.20 or more and less than 0.55, more preferably 0.30 or more and 0.50 or less, still more preferably 0.32 or more and 0.49 or less, the composition according to any one of [1] to [9].
[0028]
[11] The composition according to any one of [1] to
[10] , further containing 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, an antioxidant, and a solvent.
[0029]
[12] A light-emitting device containing the composition according to any one of [1] to
[10] .
Advantages of the Invention
[0030] According to the present invention, a composition useful for manufacturing a light-emitting device with high external quantum efficiency can be provided. Further, according to the present invention, a light-emitting device containing this composition can be provided.
Embodiments for Carrying Out the Invention
[0031] Hereinafter, preferred embodiments of the present invention will be described in detail.
[0032] <Explanation of Common Terms> Terms commonly used in this specification have the following meanings unless otherwise specified.
[0033] "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 protium atom. In the formula representing the metal complex, the solid line representing the bond with the central metal means an ionic bond, a covalent bond, or a coordination bond.
[0034] The term "low-molecular compound" refers to a compound that has no molecular weight distribution and has a molecular weight of 1×10 4 or less, and means the following compounds. The term "high-molecular compound" refers to a polymer that has a molecular weight distribution and a number-average molecular weight in terms of polystyrene of 1×10 3 or more (for example, 1×10 3 to 1×10 8 ). The term "constitutional unit" means a unit that is present in one or more in a high-molecular compound. Constitutional units contained in two or more in a high-molecular compound are generally also referred to as "repeating units". The high-molecular compound may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms. When the terminal group of the high-molecular compound remains as a polymerization active group, if the high-molecular compound is used in the production of a light-emitting element, the light-emitting characteristics and the like may deteriorate. Therefore, it is preferably a stable group. As the terminal group of the high-molecular compound, preferably, it is a group conjugated with the main chain of the high-molecular compound. For example, an aryl group or a monovalent heterocyclic group bonded to the main chain of the high-molecular compound via a carbon-carbon bond can be mentioned.
[0035] The "alkyl group" may be either linear or branched. The number of carbon atoms of the linear alkyl group, excluding the number of carbon atoms of the substituent, is usually 1 to 50, preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10. The number of carbon atoms of the branched alkyl group, excluding the number of carbon atoms of the substituent, is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, and still more preferably 1 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, and a dodecyl group. Further, the alkyl group may be a group in which some or all of the hydrogen atoms in these groups are 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, a 6-ethyloxyhexyl group).
[0036] The number of carbon atoms of the "cycloalkyl group", excluding the number of carbon atoms of the substituent, is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, and still more preferably 4 to 10. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent.
[0037] The number of carbon atoms of the "alkylene group", excluding the number of carbon atoms of the substituent, is usually 1 to 50, preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10. 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 a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0038] The number of carbon atoms of the "cycloalkylene group", excluding the number of carbon atoms of the substituent, is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, and still more preferably 4 to 10. The cycloalkylene group may have a substituent. Examples of the cycloalkylene group include a cyclohexylene group and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent.
[0039] The "alkenyl group" may be either linear or branched. The number of carbon atoms in the linear alkenyl group, excluding the carbon atoms of the substituent, is usually 2 to 30, preferably 3 to 20. The number of carbon atoms in the branched alkenyl group, excluding the carbon atoms of the substituent, is usually 3 to 30, preferably 4 to 20. The alkenyl group may have a substituent. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-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 a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0040] The number of carbon atoms in the "cycloalkenyl group", excluding the carbon atoms of the substituent, is usually 3 to 30, preferably 4 to 20. The cycloalkenyl group may have a substituent. Examples of the cycloalkenyl group include a 5-cyclohexenyl group and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0041] The "alkynyl group" may be either linear or branched. The number of carbon atoms in the linear alkynyl group, excluding the carbon atoms of the substituent, is usually 2 to 20, preferably 3 to 20. The number of carbon atoms in the branched alkynyl group, excluding the carbon atoms of the substituent, is usually 4 to 30, preferably 4 to 20. The alkynyl 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 a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0042] The number of carbon atoms in the "cycloalkynyl group", excluding the carbon atoms of the substituent, is usually 4 to 30, preferably 4 to 20. The cycloalkynyl group may have a substituent. Examples of the cycloalkynyl group include a 5-cyclohexynyl group and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0043] The "alkoxy group" may be either linear or branched. The number of carbon atoms in the linear alkoxy group, excluding the number of carbon atoms of the substituent, is usually 1 to 40, preferably 4 to 10. The number of carbon atoms in the branched alkoxy group, excluding the number of carbon atoms of the substituent, is usually 3 to 40, preferably 4 to 10. The alkoxy group may have a substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0044] The number of carbon atoms in the "cycloalkoxy group", excluding the number of carbon atoms of the substituent, is usually 3 to 40, preferably 4 to 10. The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent.
[0045] The number of carbon atoms in the "aryloxy group", excluding the number of carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 48. The aryloxy group may have a substituent. Examples of the aryloxy group include a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1-pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.
[0046] The "aromatic hydrocarbon group" means a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to the carbon atom constituting the ring from an aromatic hydrocarbon is also referred to as an "aryl group". A group obtained by removing two hydrogen atoms directly bonded to the carbon atom constituting the ring from an aromatic hydrocarbon is also referred to as an "arylene group". The number of carbon atoms of the aromatic hydrocarbon group, excluding the number of carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20.
[0047] Examples of the "aromatic hydrocarbon group" include monocyclic aromatic hydrocarbons (e.g., benzene), or polycyclic aromatic hydrocarbons (e.g., bicyclic aromatic hydrocarbons such as naphthalene, indene, naphthoquinone, indenone, and tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthraquinone, and fluorenone; tetracyclic aromatic hydrocarbons such as benzoanthracene, benzophenanthrene, benzofluorene, pyrene, and fluoranthene; pentacyclic aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, perylene, and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene; and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene). Also included are groups obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from these, and groups in which some or all of the hydrogen atoms in the group are substituted with substituents. The aromatic hydrocarbon group includes groups in which a plurality of these groups are bonded. The aromatic hydrocarbon group may have a substituent.
[0048] The aryl group may have a substituent. Examples of the aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and a group in which some or all of the hydrogen atoms in these groups are substituted with a group substituted with a substituent.
[0049] The arylene group may have a substituent. Examples of the arylene group include a phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrenediyl group, dihydrophenanthrenediyl group, naphthacenediyl group, fluorenediyl group, pyrenediyl group, perylenediyl group, chrysenediyl group, and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent. The arylene group includes a group in which a plurality of these groups are bonded. The arylene group is preferably a group represented by formula (A-1) to formula (A-20).
[0050] [Chemical formula]
[0051] [Chemical formula]
[0052] [Chemical formula]
[0053] [Chemical formula] [In the formula, R and R aEach 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 substituents. 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 respectively bonded. A plurality of R's 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 respectively bonded. A plurality of R a 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 respectively bonded. R and R a may be bonded to each other to form a ring together with the atoms to which they are respectively bonded.]
[0054] The "heterocyclic group" means a group obtained by removing one or more hydrogen atoms directly bonded to an atom (carbon atom or hetero atom) constituting the ring from a heterocyclic compound. Among heterocyclic groups, an "aromatic heterocyclic group" which is a group obtained by removing one or more hydrogen atoms directly bonded to an atom constituting the ring from an aromatic heterocyclic compound is preferred. A group obtained by removing p hydrogen atoms (p represents an integer of 1 or more) directly bonded to an atom constituting the ring from a heterocyclic compound is also referred to as a "p-valent heterocyclic group". A group obtained by removing p hydrogen atoms directly bonded to an atom constituting the ring from an aromatic heterocyclic compound is also referred to as a "p-valent aromatic heterocyclic group".
[0055] Examples of the "aromatic heterocyclic compound" include compounds in which the heterocycle itself has aromaticity, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, and compounds in which an aromatic ring is condensed to a heterocycle even if the heterocycle itself does not have aromaticity, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran.
[0056] The number of carbon atoms in the heterocyclic group, excluding the number of carbon atoms in the substituent, is usually from 1 to 60, preferably from 2 to 40, more preferably from 3 to 20. The number of heteroatoms in the heterocyclic group, excluding the number of heteroatoms in the substituent, is usually from 1 to 30, preferably from 1 to 10, more preferably from 1 to 5, and still more preferably from 1 to 3.
[0057] Examples of the heterocyclic group include a monocyclic heterocyclic compound (e.g., furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, tetrazole, pyridine, diazabenzene, and triazine), or a polycyclic heterocyclic compound (e.g., azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, benzothiophene dioxide, benzothiophene oxide, and benzopyranone, etc., bicyclic heterocyclic compounds; dibenzofuran, dibenzothiophene, dibenzothiophene dioxide, dibenzothiophene oxide, dibenzopyranone, dibenzoborole, dibenzosilole, dibenzophosphole, dibenzoselenophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, phenazaborine, phenophosphazine, phenaselenazine, phenazasiline, azaanthracene, diazaanthracene, azaphenanthrene, and diazaphenanthrene, etc., tricyclic heterocyclic compounds; hexaazatriphenylene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, and benzonaphthothiophene, etc., tetracyclic heterocyclic compounds; dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole, and diazaindenocarbazole, etc., pentacyclic heterocyclic compounds; carbazolocarbazole, benzoindolocarbazole, and benzoindenocarbazole, etc., hexacyclic heterocyclic compounds; and dibenzoindolocarbazole and dibenzoindenocarbazole, etc., heptacyclic heterocyclic compounds). Examples also include a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring, and a group in which some or all of the hydrogen atoms in the group are substituted with substituents. The heterocyclic group includes a group in which a plurality of these groups are bonded. The heterocyclic group may have a substituent.
[0058] The monovalent heterocyclic group may have a substituent. Examples of the monovalent heterocyclic group include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and a group in which some or all of the hydrogen atoms in these groups are substituted with substituents.
[0059] The divalent heterocyclic group may have a substituent. Examples of the divalent heterocyclic group include a divalent group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting a ring from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole, and a group in which some or all of the hydrogen atoms in the group are substituted with substituents. The divalent heterocyclic group includes a group in which a plurality of these groups are bonded. The divalent heterocyclic group is preferably a group represented by Formula (AA-1) to Formula (AA-34).
[0060]
Chemical formula
[0061]
Chemical formula
[0062]
Chemical formula
[0063]
Chemical formula
[0064]
Chemical formula
[0065] [Chemistry]
[0066] [Chemistry]
[0067] [In the formula, R and R a represent the same meaning as described above.]
[0068] The "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0069] The "amino group" may have a substituent, and a substituted amino group (that is, a secondary amino group or a tertiary amino group, preferably a tertiary amino group) is preferred. As the substituent of the amino group, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferred, and these groups may have a substituent. When there are a plurality of substituents of the amino group, 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 each is bonded.
[0070] The substituted amino group may have a substituent. Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, a diarylamino group, and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0071] 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 a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[0072] The "crosslinking group" is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc., and is preferably a group represented by any of formula (B-1) to formula (B-17). These groups may have substituents.
Chemical formula
[0073] Examples of the "substituent" include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, and a cycloalkynyl group. The substituent may be a crosslinking group. When there are a plurality of substituents, they may be the same or different. Further, when there are a plurality of substituents, they may be bonded to each other to form a ring together with the atoms to which they are respectively bonded, but it is preferable that no ring is formed.
[0074] Examples of the "divalent group" include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R 0 )-, a group represented by -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 includes a group in which a plurality of these groups are bonded. The divalent group may have substituents. 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 respectively bonded. R 0 represents a hydrogen atom or a substituent. R 0Examples 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. Preferably, they are a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have substituents. When there are a plurality of these 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 respectively bonded.
[0075] [Composition of the present embodiment] The composition of the present embodiment is a composition containing two or more kinds of polymer compounds, and among the two or more kinds of polymer compounds, at least one kind is a composition containing a polymer compound (B). All of the two or more kinds of polymer compounds contained in the composition of the present embodiment may be the polymer compound (B).
[0076] The types of polymer compounds contained in the composition of the present embodiment may be within the range in which the functions of the composition of the present embodiment are exhibited. The number of types of polymer compounds contained in the composition of the present embodiment is, for example, 2 or more and 30 or less. Since the production of the composition of the present embodiment is facilitated and the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 2 or more and 20 or less, more preferably 2 or more and 10 or less, still more preferably 2 or more and 5 or less, and particularly preferably 2 or 3.
[0077] The composition of the present embodiment may contain only one kind of the polymer compound (B), or may contain two or more kinds.
[0078] The types of the polymer compound (B) contained in the composition of the present embodiment may be within the range in which the functions of the composition of the present embodiment are exhibited. The number of types of the polymer compound (B) contained in the composition of the present embodiment is, for example, 1 or more and 30 or less. Since the production of the composition of the present embodiment is facilitated and the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, still more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less, and especially preferably 1 or 2 types.
[0079] <Polymer compound (B)> The polymer compound (B) is a group obtained by removing one or more hydrogen atoms from a low-molecular compound (B) having a condensed heterocyclic skeleton (b) containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an sp 3 carbon atom and a nitrogen atom in the ring (hereinafter also referred to as "heterocyclic group (b')"). It is a polymer compound containing a structural unit (B).
[0080] (Low-molecular compound (B)) The low-molecular compound (B) is a low-molecular compound having a condensed heterocyclic skeleton (b) containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an sp 3 carbon atom and a nitrogen atom in the ring. The low-molecular compound (B) may have a substituent. Examples of the substituent that the low-molecular compound (B) may have include the same substituents as the substituents that the heterocyclic group (b') described later may have. The condensed heterocyclic skeleton (b) may have a substituent. Examples of the substituent that the condensed heterocyclic skeleton (b) may have include the same substituents as the substituents that the heterocyclic group (b') described later may have. The low-molecular compound (B) may be a compound consisting only of the condensed heterocyclic skeleton (b), or a compound in which a substituent (for example, an aryl group and a monovalent heterocyclic group, etc.) is substituted on the condensed heterocyclic skeleton (b). In the low-molecular compound (B), when the condensed heterocyclic skeleton (b) contains a nitrogen atom, at least one of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) is preferably a nitrogen atom that does not form a double bond, and more preferably all of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) are nitrogen atoms that do not form a double bond. The low-molecular compound (B) is preferably a low-molecular compound that does not contain a transition metal element (that is, a low-molecular compound composed of only typical elements). The group obtained by removing one or more hydrogen atoms from the low-molecular compound (B) may be, for example, a group obtained by removing one or more hydrogen atoms from the condensed heterocyclic skeleton (b), or a group obtained by removing one or more hydrogen atoms from a substituent (for example, an aryl group or a monovalent heterocyclic group) substituted on the condensed heterocyclic skeleton (b).
[0081] The molecular weight of the low-molecular compound (B) is preferably 1×10 2 ~5×10 3 and more preferably 2×10 2 ~3×10 3 and still more preferably 3×10 2 ~1.5×10 3 and particularly preferably 4×10 2 ~1×10 3
[0082] (Constituent unit (B)) The constituent unit (B) may have only one type of heterocyclic group (b’), or may have two or more types. The number of carbon atoms of the condensed heterocyclic skeleton (b), excluding the number of carbon atoms of the substituent, is usually 1 to 60, preferably 5 to 40, more preferably 10 to 30, and still more preferably 15 to 20. The number of heteroatoms of the condensed heterocyclic skeleton (b), excluding the number of heteroatoms of the substituent, is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, still more preferably 2 to 5, and particularly preferably 2 or 3. The number of boron atoms in the condensed heterocyclic ring skeleton (b), excluding the boron atoms of the substituents, is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1. The total number of oxygen atoms, sulfur atoms, selenium atoms, sp 3 The total number of carbon atoms and nitrogen atoms in the condensed heterocyclic ring skeleton (b), excluding the atomic numbers of the substituents, is usually 1 to 20, preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 1 or 2.
[0083] Since the condensed heterocyclic ring skeleton (b) makes the external quantum efficiency of the light-emitting element of the present embodiment more excellent, it preferably contains at least one selected from the group consisting of a boron atom and an oxygen atom, a sulfur atom, and a nitrogen atom in the ring, more preferably contains a boron atom and a nitrogen atom in the ring, and still more preferably contains a boron atom and a nitrogen atom that does not form a double bond in the ring.
[0084] Since the condensed heterocyclic ring skeleton (b) makes the external quantum efficiency of the light-emitting element of the present embodiment more excellent, it is preferably a 3- to 12-membered condensed heterocyclic ring skeleton, more preferably a 3- to 6-membered condensed heterocyclic ring skeleton, and still more preferably a 5-membered condensed heterocyclic ring skeleton.
[0085] Preferred examples of the substituent that the heterocyclic group (b') may have include 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 preferred are 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 preferred are an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group. Particularly preferred are an alkyl group, a cycloalkyl group, an aryl group, or a substituted amino group. These groups may further have a substituent.
[0086] In the substituent that the complex ring group (b') may have, as the aryl group, preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, still more preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from benzene, naphthalene, anthracene, phenanthrene or fluorene, particularly preferably, it is a phenyl group, and these groups may have a substituent.
[0087] In the substituent that the complex ring group (b') may have, as the monovalent complex ring group, preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from a monocyclic or bicyclic to hexacyclic heterocyclic compound, more preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from a monocyclic, bicyclic or tricyclic heterocyclic compound, still more preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, particularly preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting the ring from pyridine, diazabenzene or triazine, and these groups may have a substituent.
[0088] In the substituent amino group that the complex ring group (b') may have, as the substituent that the amino group has, an aryl group or a monovalent complex ring group is preferable, and an aryl group is more preferable, and these groups may further have a substituent. Examples and preferable ranges of the aryl group and the monovalent complex ring group in the substituent that the amino group has are the same as the examples and preferable ranges of the aryl group and the monovalent complex ring group in the substituent that the complex ring group (b') may have, respectively.
[0089] Examples of the substituent that the substituent that the complex ring group (b') may further have may further have include 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 complex ring group, or a substituted amino group, preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent complex ring group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, or an aryl group, still more preferably an alkyl group or a cycloalkyl group, particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent, but preferably do not have a further substituent. Examples and preferred ranges of the aryl group, the monovalent complex ring group, and the substituted amino group in the substituent that the substituent that the complex ring group (b') may further have may further have are the same as the examples and preferred ranges of the aryl group, the monovalent complex ring group, and the substituted amino group in the substituent that the complex ring group (b') may further have, respectively.
[0090] The "nitrogen atom not forming a double bond" means a nitrogen atom bonded to three other atoms by single bonds respectively. "Containing a nitrogen atom not forming a double bond in the ring" means containing -N(-R N )- (wherein R N represents a hydrogen atom or a substituent) or a formula:
[0091]
Chemical formula
[0092] Since the synthesis of the polymer compound (B) is easy and the external quantum efficiency of the light-emitting device of this embodiment is more excellent, the constitutional unit (B) is a constitutional unit having a group obtained by removing 1 to 5 hydrogen atoms from the low molecular compound (B), more preferably a constitutional unit having a group obtained by removing 1 to 3 hydrogen atoms from the low molecular compound (B), still more preferably a constitutional unit having a group obtained by removing 1 or 2 hydrogen atoms from the low molecular compound (B), and particularly preferably a constitutional unit having a group obtained by removing 2 hydrogen atoms from the low molecular compound (B).
[0093] The structural unit (B) is preferably a structural unit represented by formula (BP-1), formula (BP-2) or formula (BP-3) because the polymer compound (B) is easy to synthesize and the external quantum efficiency of the light-emitting element of the present embodiment is more excellent. More preferably, it is a structural unit represented by formula (BP-1) or formula (BP-2), and still more preferably, it is a structural unit represented by formula (BP-2).
[0094] 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, still more preferably an arylene group, and these groups may have substituents. L BP1 Examples and preferred ranges of the arylene group and the divalent heterocyclic group in are the same as the examples and preferred ranges of the arylene group and the divalent heterocyclic group in Ar described later. Y1 Examples and preferred ranges of the arylene group and the divalent heterocyclic group in are the same as the examples and preferred ranges of the arylene group and the divalent heterocyclic group in Ar described later. L BP1 As the alkylene group in, preferably, it is a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have substituents. R BP1 Examples and preferred ranges of are the same as the examples and preferred ranges of R~R described later. X1 ~R X3 Examples and preferred ranges of are the same as the examples and preferred ranges of R~R described later.
[0095] n BP1 is preferably an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and still more preferably 0.
[0096] Ar BP1 Examples of the hydrocarbon group in include an aromatic hydrocarbon group which may have a substituent and an aliphatic hydrocarbon group which may have a substituent. The hydrocarbon group in Ar includes a group in which a plurality of these groups are bonded. BP1 Examples of the hydrocarbon group in include an aromatic hydrocarbon group which may have a substituent and an aliphatic hydrocarbon group which may have a substituent. The hydrocarbon group in Ar includes a group in which a plurality of these groups are bonded. Ar BP1In this case, examples of the aliphatic hydrocarbon group include a group obtained by removing one hydrogen atom from an alkylene group or a cycloalkylene group, preferably a group obtained by removing one hydrogen atom from an alkylene group, and these groups may have a substituent. Examples and preferred ranges of this alkylene group are the same as those of the alkylene group in L BP1 and the preferred ranges are the same as those of the alkylene group in BP1 . Ar BP1 In this case, examples of the aromatic hydrocarbon group include a group obtained by removing one hydrogen atom from an arylene group, and this group may have a substituent. Examples and preferred ranges of this arylene group are the same as those of the arylene group in Ar Y1 described later and the preferred ranges are the same as those of the arylene group in Y1 . Ar BP1 In this case, examples of the heterocyclic group include a group obtained by removing one hydrogen atom from a divalent heterocyclic group, and this group may have a substituent. Examples and preferred ranges of this divalent heterocyclic group are the same as those of the divalent heterocyclic group in Ar Y1 described later and the preferred ranges are the same as those of the divalent heterocyclic group in Y1 . L BP1 and Ar BP1 Examples and preferred examples of the substituent that L Y1 and Ar may have are the same as those of the substituent that the group represented by Ar
[0097] The low-molecular compound (B) is preferably a compound represented by the formula (1-1), the formula (1-2) or the formula (1-3) because the external quantum efficiency of the light-emitting element of this embodiment is more excellent, more preferably a compound represented by the formula (1-2) or the formula (1-3), and still more preferably a compound represented by the formula (1-2).
[0098] Ar 1 Ar 2 and Ar 3Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon or a monocyclic or bicyclic to hexacyclic heterocyclic compound. More preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon or a monocyclic, bicyclic or tricyclic heterocyclic compound. Even more preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic aromatic hydrocarbon or a monocyclic heterocyclic compound. Particularly preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from benzene, pyridine or diazabenzene. Most preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from benzene. These groups may have substituents. Ar 1 , Ar 2 and Ar 3 Examples and preferred ranges of the substituents that [[ID=]] may have are the same as the examples and preferred ranges of the substituents that the heterocyclic group (b') may have.
[0099] Y 1 Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group. More preferably, it is an oxygen atom, a sulfur atom or a group represented by -N(Ry)-. Even more preferably, it is a group represented by -N(Ry)-. These groups may have substituents.
[0100] Y 2 and Y 3Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is 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, 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, still 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)-. These groups may have substituents.
[0101] Y 2 and Y 3 The arylene group in and Y is preferably a group obtained by removing two hydrogen atoms directly bonded to the 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 the carbon 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 the 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 the carbon atoms constituting the ring from benzene, naphthalene or fluorene, and especially preferably a phenylene group. These groups may have substituents. Y 2 and Y 3The divalent heterocyclic group in the formula (I) is preferably a group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting the ring from a monocyclic or bicyclic to hexacyclic heterocyclic compound, more preferably a group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting the ring from a monocyclic, bicyclic or tricyclic heterocyclic compound, and even more preferably a group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting the ring from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine. ), particularly preferably a group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting the ring from pyridine, diazabenzene, triazine, carbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine, and particularly preferably a group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting the ring from pyridine, diazabenzene or triazine, and these groups may have a substituent. Y 1 , Y 2 and Y 3 The alkylene group in is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
[0102] Since the external quantum efficiency of the light emitting device of this embodiment is superior, Y 1 , Y 2 and Y 3 are preferably all oxygen atoms, sulfur atoms, or groups represented by -N(Ry)-, 1 , Y 2 and Y 3 It is more preferable that all of the above are a group represented by -N(Ry)-.
[0103] Y 1 , Y 2 and Y3 Examples and preferred ranges of substituents which may be possessed are the same as those of the substituents which the heterocyclic group (b') may have.
[0104] 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, still more preferably an aryl group, and these groups may have substituents. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in Ry are the same as those of the aryl group and the monovalent heterocyclic group in the substituents which the heterocyclic group (b') may have, respectively. Examples and preferred ranges of substituents which Ry may have are the same as those of the substituents which the heterocyclic group (b') may have.
[0105] Y 1 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring, but it is preferable not to form a ring because the synthesis of the polymer compound (B) is easy. Y 1 and Ar 1 When Y and Ar are bonded 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, a group represented by -N(R 0 ), a group represented by -B(R 0 ), a group represented by -O-, a group represented by -S- or a group represented by -Se-, more preferably an alkylene group, a cycloalkylene group, a group represented by -N(R 0 ), a group represented by -B(R 0 ), a group represented by -O-, a group represented by -S- or a group represented by -Se-, still more preferably an alkylene group, a group represented by -N(R 0 ), a group represented by -O- or a group represented by -S-, particularly preferably a group represented by -O-, a group represented by -S- or a group represented by -N(R 0 ), and especially preferably a group represented by -N(R 0)-represented groups, and these groups may have substituents. Y 1 and Ar 1 When Y and Ar are bonded 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 the same as the examples and preferred ranges of the arylene group, divalent heterocyclic group, and alkylene group in Y 2 and Y 3 respectively. Y 1 and Ar 1 When Y and Ar are bonded via a divalent group to form a ring, examples and preferred ranges of the substituents that the divalent group may have are the same as the examples and preferred ranges of the substituents that Y 2 and Y 3 may have respectively. Y 1 and Ar 1 When Y and Ar are bonded via a divalent group to form a ring, examples and preferred ranges of R 0 in the divalent group are the same as the examples and preferred ranges of Ry. Y 1 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring, but it is preferred not to form a ring because the synthesis of the polymer compound (B) is easy. Y 1 and Ar 2 When Y and Ar are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group are the same as the examples and preferred ranges of the divalent group when Y 1 and Ar 1 are bonded via a divalent group to form a ring. Y 2 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring, but it is preferred not to form a ring because the synthesis of the polymer compound (B) is easy. Y 2 and Ar 1 When Y and Ar are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group are the same as the examples and preferred ranges of the divalent group when Y 1 and Ar 1This is the same as the examples and preferred ranges of the divalent groups in the case where they are bonded via a divalent group to form a ring. Y 2 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring, but it is preferable not to form a ring because the synthesis of the polymer compound (B) is easy. Y 2 and Ar 3 In the case where they are bonded via a divalent group to form a ring, the examples and preferred ranges of the divalent groups are Y 1 and Ar 1 This is the same as the examples and preferred ranges of the divalent groups in the case where they are bonded via a divalent group to form a ring. Y 3 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring, but it is preferable not to form a ring because the synthesis of the polymer compound (B) is easy. Y 3 and Ar 2 In the case where they are bonded via a divalent group to form a ring, the examples and preferred ranges of the divalent groups are Y 1 and Ar 1 This is the same as the examples and preferred ranges of the divalent groups in the case where they are bonded via a divalent group to form a ring. Y 3 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring, but it is preferable not to form a ring because the synthesis of the polymer compound (B) is easy. Y 3 and Ar 3 In the case where they are bonded via a divalent group to form a ring, the examples and preferred ranges of the divalent groups are Y 1 and Ar 1 This is the same as the examples and preferred ranges of the divalent groups in the case where they are bonded via a divalent group to form a ring.
[0106] The constituent unit (B) is a constituent unit having a group obtained by removing one to three hydrogen atoms from a compound represented by the formula (1-1), formula (1-2) or formula (1-3), and is preferably a constituent unit represented by the formula (BP-1), formula (BP-2) or formula (BP-3). It is more preferably a constituent unit having a group obtained by removing one or two hydrogen atoms from a compound represented by the formula (1-2) or formula (1-3), and is a constituent unit represented by the formula (BP-1) or formula (BP-2). Even more preferably, it is a constituent unit having a group obtained by removing two hydrogen atoms from a compound represented by the formula (1-2), and is a constituent unit represented by the formula (BP-2).
[0107] Examples of the constituent unit (B) include constituent units represented by the following formula.
[0108] [Chemical formula]
[0109] [Chemical formula]
[0110] [Chemical formula] [In the formula, R TS is 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 substituents. When there are a plurality of R TS , they may be the same or different.]
[0111] R TS Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R TSExamples and preferred ranges of substituents which may be possessed are the same as those of substituents which may be further possessed by substituents which may be possessed by the heterocyclic group (b’).
[0112] The content of the structural unit (B) contained in the polymer compound (B) may be in a range in which the function as the polymer compound (B) is exhibited. The content of the structural unit (B) contained in the polymer compound (B) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (B). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0.5 to 30 mol%, and especially preferably 1 to 10 mol%. The structural unit (B) may be contained alone by 1 type in the polymer compound (B), or may be contained by 2 types or more. In addition, when the polymer compound (B) contains 2 types or more of the structural units (B), the content represents the total content thereof.
[0113] (Other structural units) Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, the polymer compound (B) preferably further contains at least 1 type of structural unit selected from the group consisting of the structural unit represented by the formula (Y) and the structural unit represented by the formula (X). However, the structural unit represented by the formula (Y) and the structural unit represented by the formula (X) are different from the structural unit (B). Further, the structural unit represented by the formula (Y) is different from the structural unit represented by the formula (X).
[0114] Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, the polymer compound (B) preferably further contains the structural unit represented by the formula (Y) described later. Further, since the hole-transporting property of the polymer compound (B) is excellent, the polymer compound (B) preferably further contains the structural unit represented by the formula (X). Since the external quantum efficiency of the light-emitting element of the present embodiment is further excellent and the hole-transporting property of the polymer compound (B) is excellent, the polymer compound (B) preferably further contains the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).
[0115] · The structural unit represented by formula (Y) Ar Y1 The arylene group represented by is preferably a group represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A-13) or formula (A-19), more preferably a group represented by formula (A-1), formula (A-7), formula (A-9) or formula (A-19), and still more preferably a group represented by formula (A-1) or formula (A-9), and these groups may have substituents.
[0116] Ar Y1 The divalent heterocyclic group represented by is preferably a group represented by formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) or formula (AA-20), more preferably a group represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20), and these groups may have substituents.
[0117] Ar Y1 In the divalent group in which at least one arylene group represented by and at least one divalent heterocyclic group are directly bonded, the preferable ranges of the arylene group and the divalent heterocyclic group are the same as the preferable ranges of the arylene group and the divalent heterocyclic group represented by Ar Y1 respectively.
[0118] Ar Y1 Examples of the divalent group in which at least one arylene group represented by and at least one divalent heterocyclic group are directly bonded include the same as the divalent group in which at least one arylene group represented by the later-described Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded.
[0119] Ar Y1 The substituent that the group represented by may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have substituents.
[0120] Examples of the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10). From the viewpoint of the external quantum efficiency of the light-emitting element of this embodiment, the structural units represented by formulas (Y-1) to (Y-3) are preferable. From the viewpoint of electron transport property, the structural units represented by formulas (Y-4) to (Y-7) are preferable. From the viewpoint of hole transport property, the structural units represented by formulas (Y-8) to (Y-10) are preferable.
[0121]
Chemical formula
[0122] [In the formula, R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have substituents. A plurality of R Y1 may be the same or different, and adjacent R Y1 's may be bonded to each other to form a ring together with the carbon atoms to which they are respectively bonded.]
[0123] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have substituents.
[0124] The structural unit represented by formula (Y-1) is preferably the structural unit represented by formula (Y-1’).
[0125]
Chemical formula
[0126] [In the formula, R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have substituents. A plurality of R Y11 may be the same or different.]
[0127] R Y11 is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have substituents.
[0128]
Chemical formula
[0129] [In the formula, R Y1 represents the same meaning as described above. X Y1 is a group represented by -C(R Y2 )2-, -C(R Y2 )=C(R Y2 )- or C(R Y2 )2-C(R Y2 )2-. R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have substituents. When there are a plurality of R Y2 , they may be the same or different, and R Y2 s may be bonded to each other to form a ring together with the carbon atoms to which they are respectively bonded.]
[0130] R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have substituents.
[0131] X Y1 In, the two Rs in the group represented by -C(R Y2 )2- Y2The combination of R is preferably such that both are alkyl groups or cycloalkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group or monovalent heterocyclic group, more preferably such that both are alkyl groups or both are aryl groups, and these groups may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 The group represented by 2- is preferably a group represented by formulae (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have a substituent.
[0132] [ka]
[0133] X Y1 In the above, -C(R Y2 )=C(R Y2 Two R in the group represented by Y2 The combination of the above is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent.
[0134] X Y1 In the above, -C(R Y2 )2-C(R Y2 )2-, where R Y2 is preferably an alkyl group or a cycloalkyl group which may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 )2-C(R Y2 The group represented by (Y-)2- is preferably a group represented by formulae (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups may have a substituent.
[0135]
Chem.
[0136] [In the formula, R Y2 represents the same meaning as described above.]
[0137] The structural unit represented by formula (Y-2) is preferably the structural unit represented by formula (Y-2’).
[0138]
Chem.
[0139] [In the formula, RY1 and XY1 represent the same meaning as described above.]
[0140]
Chem.
[0141] [In the formula, R Y1 and X Y1 represent the same meaning as described above.]
[0142] The structural unit represented by formula (Y-3) is preferably the structural unit represented by formula (Y-3’).
[0143]
Chem.
[0144] [In the formula, R Y11 and X Y1 represent the same meaning as described above.]
[0145]
Chem.
[0146]
Chem.
[0147] [In the formula, R Y1 represents the same meaning as described above. R Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have substituents.]
[0148] RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have substituents.
[0149] The structural unit represented by formula (Y-4) is preferably the structural unit represented by formula (Y-4’), and the structural unit represented by formula (Y-6) is preferably the structural unit represented by formula (Y-6’).
[0150] [Chemical formula]
[0151] [In the formula, RY1 and RY3 represent the same meaning as described above.]
[0152] [Chemical formula] [In the formula, R Y1 represents the same meaning as described above. R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have substituents.]
[0153] R Y4is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have substituents.
[0154] Examples of the structural unit represented by the formula (Y) include a structural unit composed of an arylene group represented by the formulas (Y-101) to (Y-141), a structural unit composed of a divalent heterocyclic group represented by the formulas (Y-201) to (Y-202), and a structural unit composed of a divalent group in which at least one arylene group represented by the formulas (Y-301) to (Y-306) and at least one divalent heterocyclic group are directly bonded.
[0155]
Chemical formula
[0156]
Chemical formula
[0157]
Chemical formula
[0158]
Chemical formula
[0159]
Chemical formula
[0160]
Chemical formula
[0161]
Chemical formula
[0162] [Chemical]
[0163] [Chemical]
[0164] [Chemical]
[0165] [Chemical]
[0166] [Chemical]
[0167] When the high molecular compound (B) contains a structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) may be within the range in which the functions of the high molecular compound (B) are exhibited.
[0168] When the high molecular compound (B) contains a structural unit represented by the formula (Y) and Ar in the formula (Y) Y1 is an arylene group, the content of the structural unit represented by the formula (Y) contained in the high molecular compound (B) is, for example, 0.01 to 99.99 mol% with respect to the total amount of the structural units contained in the high molecular compound (B). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 1 to 99.9 mol%, more preferably 10 to 99.5 mol%, still more preferably 30 to 99 mol%, particularly preferably 50 to 98 mol%, and especially preferably 70 to 97 mol%. In addition, when the high molecular compound (B) contains two or more structural units represented by the formula (Y), the content represents the total content.
[0169] When the high molecular compound (B) contains a structural unit represented by the formula (Y) and Ar in the formula (Y)Y1 When it is 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, the content of the structural unit represented by the formula (Y) contained in the polymer compound (B) is, for example, 0.01 to 99.99 mol% with respect to the total amount of the structural units contained in the polymer compound (B). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.05 to 99 mol%, more preferably 0.1 to 90 mol%, still more preferably 0.5 to 70 mol%, particularly preferably 1 to 50 mol%, and especially preferably 2 to 20 mol%. When the polymer compound (B) contains two or more structural units represented by the formula (Y), the content represents the total content.
[0170] In the polymer compound (B), the structural unit represented by the formula (Y) may be contained alone or in two or more kinds.
[0171] [Structural unit represented by formula (X)] a X1 Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 2 or less, more preferably 0 or 1, and still more preferably 0.
[0172] a X2 Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 2 or less, more preferably 0 or 1, and still more preferably 0.
[0173] R X1 R X2 and R X3 are 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, still more preferably an aryl group, and these groups may have substituents.
[0174] Ar X1 and Ar X3The arylene group represented by is preferably a group represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), or formula (A-19), more preferably a group represented by formula (A-1) or formula (A-9), still more preferably a group represented by formula (A-1), and these groups may have substituents.
[0175] Ar X1 and Ar X3 The divalent heterocyclic group represented by is preferably a group represented by formula (AA-1), formula (AA-2), or formula (AA-7) to formula (AA-26), and these groups may have substituents.
[0176] Ar X1 and Ar X3 is preferably an arylene group which may have substituents.
[0177] Ar X2 and Ar X4 The arylene group represented by is preferably a group represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), or formula (A-19), more preferably a group represented by formula (A-1), formula (A-7), formula (A-9), or formula (A-19), and these groups may have substituents.
[0178] Ar X2 and Ar X4 The preferred range of the divalent heterocyclic group represented by is the same as the preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group represented by are directly bonded, the preferred range and more preferred range of the arylene group and the divalent heterocyclic group are the same as the preferred range and more preferred range of the arylene group and the divalent heterocyclic group represented by Ar
[0179] Ar X2 and Ar X4 respectively. X1 and Ar X3 The preferred range and more preferred range of the arylene group and the divalent heterocyclic group represented by are the same as the preferred range and more preferred range of the arylene group and the divalent heterocyclic group represented by Ar
[0180] Ar X2 and Ar X4 Examples of the divalent group in which at least one arylene group represented by and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulas, and these groups may have substituents.
[0181] [Chemical formula]
[0182] [In the formula, R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have substituents.]
[0183] R XX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have substituents.
[0184] Ar X2 and Ar X4 are preferably arylene groups which may have substituents.
[0185] Ar X1 ~Ar X4 and R X1 ~R X3 Preferred examples of the substituents that the groups represented by may have are alkyl groups, cycloalkyl groups or aryl groups, and these groups may further have substituents.
[0186] The structural unit represented by formula (X) is preferably a structural unit represented by formula (X-1) to (X-7), more preferably a structural unit represented by formula (X-1) and formula (X-3) to (X-7), still more preferably a structural unit represented by formula (X-1) and formula (X-3) to (X-6), and even more preferably a structural unit represented by formula (X-1).
[0187] [Chemical formula]
[0188] [Chemical formula]
[0189] [Chemical formula]
[0190] [Chemical formula]
[0191] [In the formula, R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or a cyano group, and these groups may have substituents. A plurality of R X4 may be the same or different. A plurality of R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.]
[0192] Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-23), and preferably structural units represented by formula (X1-1) and formulas (X1-6) to (X1-14).
[0193] [Chemical formula]
[0194] [Chemical formula]
[0195] [Chemical]
[0196] [Chemical]
[0197] [Chemical]
[0198] [Chemical]
[0199] [Chemical]
[0200] When the polymer compound (B) contains a structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) may be within the range where the function as the polymer compound (B) is exhibited. When the polymer compound (B) contains a structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) contained in the polymer compound (B) is, for example, 0.01 to 99.99 mol% with respect to the total amount of the structural units contained in the polymer compound (B). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent and the hole-transporting property of the polymer compound (B) is more excellent, it is preferably 0.05 to 99 mol%, more preferably 0.1 to 90 mol%, still more preferably 0.5 to 70 mol%, particularly preferably 1 to 50 mol%, and especially preferably 2 to 20 mol%. In addition, when the polymer compound (B) contains two or more structural units represented by the formula (X), the content represents the total content.
[0201] In the polymer compound (B), the structural unit represented by the formula (X) may be contained only as one kind, or may be contained as two or more kinds.
[0202] When the polymer compound (B) contains a structural unit represented by the formula (X) and / or a structural unit represented by the formula (Y), and when it contains the structural unit (B), the total content of the structural unit represented by the formula (X), the structural unit represented by the formula (Y), and the structural unit (B) may be within the range where the function as the polymer compound (B) is exhibited. When the polymer compound (B) contains a structural unit represented by the formula (X) and / or a structural unit represented by the formula (Y), and the structural unit (B), the total content of the structural unit represented by the formula (X), the structural unit represented by the formula (Y), and the structural unit (B) is, for example, 1 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (B). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent and the hole-transporting property of the polymer compound (B) is excellent, it is preferably 10 to 100 mol%, more preferably 30 to 100 mol%, still more preferably 50 to 100 mol%, particularly preferably 70 to 100 mol%, and especially preferably 90 to 100 mol%.
[0203] (Examples of the polymer compound (B), etc.) Examples of the polymer compound (B) include, for example, polymer compounds (BP-1) to (BP-8). Here, the "other" structural unit means a structural unit other than the structural unit (B), the structural unit represented by the formula (Y), and the structural unit represented by the formula (X).
[0204] [Table 1]
[0205] [In the table, p b , q b , r b , s b and t b represent the molar ratios of the respective structural units. p b +q b +r b +s b +t b = 100, and 100 ≥ p b +q b +r b +s b ≥ 70.]
[0206] The polymer compound (B) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms, but is preferably a copolymer.
[0207] The number average molecular weight of the polymer compound (B) in terms of polystyrene is preferably 5×10 3 ~1×10 6 and more preferably 1×10 4 ~5×10 5 and even more preferably 3×10 4 ~1.5×10 5 . The weight average molecular weight of the polymer compound (B) in terms of polystyrene is preferably 1×10 4 ~2×10 6 and more preferably 2×10 4 ~1×10 6 and even more preferably 5×10 4 ~5×10 5 . When the number average molecular weight and the weight average molecular weight of the polymer compound (B) in terms of polystyrene are within the above ranges, the film-forming property of the composition of the present embodiment is likely to be improved.
[0208] (Method for producing the polymer compound (B)) The polymer compound (B) can be produced by the same method as the method for producing the polymer compound (A) described later.
[0209] <Polymer compound (A)> The composition of the present embodiment is a composition containing two or more polymer compounds, and at least one of the two or more polymer compounds may be a polymer compound (A). That is, the composition of the present embodiment may be a composition containing one or more polymer compounds (B) and one or more polymer compounds (A). However, the polymer compound (A) is different from the polymer compound (B), and the polymer compound (A) is a polymer compound that does not contain the constituent unit (B).
[0210] All the polymer compounds contained in the composition of the present embodiment may be only two or more types of polymer compounds (B), or may be one or more types of polymer compounds (B) and one or more types of polymer compounds (A). However, since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, preferably, they are one or more types of polymer compounds (B) and one or more types of polymer compounds (A). That is, since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, the composition of the present embodiment is preferably a composition containing one or more types of polymer compounds (B) and one or more types of polymer compounds (A).
[0211] When the composition of the present embodiment contains a polymer compound (A), the type of the polymer compound (A) contained in the composition of the present embodiment may be within the range in which the function as the composition of the present embodiment is exhibited. When the composition of the present embodiment contains a polymer compound (A), the type of the polymer compound (A) contained in the composition of the present embodiment is, for example, one or more and 30 or less, and the production of the composition of the present embodiment becomes easy, and since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, preferably it is one or more and 20 or less, more preferably one or more and 10 or less, still more preferably one or more and 5 or less, particularly preferably one or more and 3 or less, and most preferably one or two.
[0212] The polymer compound (A) is not particularly limited as long as it is a polymer compound that exhibits the function as the polymer compound (A). Examples of the polymer compound (A) include the polymer compounds exemplified in the sections of hole transport materials, hole injection materials, electron transport materials, electron injection materials, and light-emitting materials described below, and polymer compounds containing at least one structural unit selected from the group consisting of the structural unit represented by formula (Y) and the structural unit represented by formula (X). Since the external quantum yield of the light-emitting device of the present embodiment is more excellent, the polymer compound (A) is preferably a polymer compound containing at least one structural unit selected from the group consisting of the structural unit represented by the formula (Y) and the structural unit represented by the formula (X), and more preferably a polymer compound containing the structural unit represented by the formula (Y). The polymer compound (A) may be a single type of polymer compound, or a combination of a plurality of types of polymer compounds may be used.
[0213] Since the external quantum efficiency of the light-emitting device of the present embodiment is more excellent, the polymer compound (A) preferably contains the structural unit represented by the formula (Y). Further, since the hole-transporting property of the polymer compound (A) is excellent, the polymer compound (A) preferably contains the structural unit represented by the formula (X). Since the external quantum efficiency of the light-emitting device of the present embodiment is more excellent and the hole-transporting property of the polymer compound (A) is excellent, the polymer compound (A) preferably contains the structural unit represented by the formula (Y) and the structural unit represented by the formula (X). Examples and preferred ranges of the structural units represented by the formula (Y) and the formula (Y) that the polymer compound (A) may contain are the same as the examples and preferred ranges of the structural units represented by the formula (Y) and the formula (Y) that the polymer compound (B) may contain. Examples and preferred ranges of the structural units represented by the formula (X) and the formula (X) that the polymer compound (A) may contain are the same as the examples and preferred ranges of the structural units represented by the formula (X) and the formula (X) that the polymer compound (B) may contain.
[0214] When the polymer compound (A) contains a structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) may be within the range in which the functions of the polymer compound (A) are exhibited. When the polymer compound (A) contains a structural unit represented by the formula (X), the content of the structural unit represented by the formula (X) contained in the polymer compound (A) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (A). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent and the hole-transporting property of the polymer compound (A) is excellent, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0.5 to 30 mol%, and especially preferably 1 to 10 mol%. In addition, when the polymer compound (A) contains two or more kinds of structural units represented by the formula (X), the content represents the total content thereof. The structural unit represented by the formula (X) may be contained only in one kind or two or more kinds in the polymer compound (A).
[0215] When the polymer compound (A) contains a structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) may be within the range in which the functions of the polymer compound (A) are exhibited. When the polymer compound (A) contains a structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) contained in the polymer compound (A) is, for example, 0.1 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (A). Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 1 to 100 mol%, more preferably 10 to 100 mol%, still more preferably 30 to 100 mol%, particularly preferably 50 to 100 mol%, and especially preferably 70 to 100 mol%. In addition, when the polymer compound (A) contains two or more kinds of structural units represented by the formula (Y), the content represents the total content thereof. The structural unit represented by the formula (Y) may be contained only in one kind or two or more kinds in the polymer compound (A).
[0216] When the polymer compound (A) contains a structural unit represented by the formula (X) and / or a structural unit represented by the formula (Y), the total content of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) may be within the range in which the function of the polymer compound (A) is exhibited. When the polymer compound (A) contains a structural unit represented by the formula (X) and / or a structural unit represented by the formula (Y), the total content of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) contained in the polymer compound (A) is, for example, 1 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (A). Since the polymer compound (A) has excellent hole transport properties and the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 10 to 100 mol%, more preferably 30 to 100 mol%, still more preferably 50 to 100 mol%, particularly preferably 70 to 100 mol%, and especially preferably 90 to 100 mol%.
[0217] Examples of the polymer compound (A) include polymer compounds AP-1 to AP-7. Here, "others" means structural units other than the structural unit represented by the formula (X), the structural unit represented by the formula (Y), and the structural unit represented by the formula (B).
[0218] [Table 2]
[0219] [In the table, p a , q a , r a and s a represent the molar ratio (mol%) of each structural unit. p a +q a +r a +s a = 100, and 70 ≤ p a +q a +r a ≤ 100.]
[0220] The polymer compound (A) 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.
[0221] The number average molecular weight of the polymer compound (A) in terms of polystyrene is preferably 5×10 3 ~1×10 6 and more preferably 1×10 4 ~5×10 5 and still more preferably 3×10 4 ~1.5×10 5 The weight average molecular weight of the polymer compound (A) in terms of polystyrene is preferably 1×10 4 ~2×10 6 and more preferably 2×10 4 ~1×10 6 and still more preferably 5×10 4 ~5×10 5
[0222] (Method for producing the polymer compound (A)) The polymer compound (A) can be produced, for example, using known polymerization methods described in Chemical Review, Vol. 109, pp. 897-1091 (2009), International Publication No. 1998 / 011150, International Publication No. 2013 / 191088, Japanese Patent Application Laid-Open No. 2012-036388, Japanese Patent Application Laid-Open No. 2014-148663, Japanese Patent Application Laid-Open No. 2010-196040, Japanese Patent Application Laid-Open No. 2010-260879, etc. In other words, for example, it can be produced using polymerization methods such as coupling reactions using transition metal catalysts such as Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction, and Kumada reaction.
[0223] In the above polymerization method, examples of the method of charging monomers include a method of charging the entire amount of monomers into the reaction system at once, a method of charging a part of the monomers, reacting them, and then charging the remaining monomers all at once, continuously, or in portions, and a method of charging the monomers continuously or in portions.
[0224] Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.
[0225] The post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, a method of adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitated precipitate, and then drying, etc., alone or in combination. When the purity of the polymer compound (A) is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, and column chromatography.
[0226] <Other components> The composition of this embodiment may further contain 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, and an antioxidant. However, the light-emitting material, hole transport material, hole injection material, electron transport material, electron injection material, and antioxidant further contained in the composition of this embodiment are low molecular compounds.
[0227] (Hole transport material) The hole transport material is classified into a low molecular compound and a high molecular compound, and the high molecular compound is preferable, and the high molecular compound having a cross-linking group is more preferable.
[0228] Examples of the low molecular compound 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). Examples of the high molecular compound include polyvinylcarbazole and its derivatives; polyarylene having an aromatic amine structure in the side chain or main chain and its derivatives. The high molecular compound may be a compound to which an electron-accepting site is bonded. Examples of the electron-accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, and fullerene is preferable.
[0229] When the composition of the present embodiment contains a hole transport material that is a low molecular weight compound, the content of the hole transport material is usually 0.01 to 99 parts by mass, preferably 0.05 to 90 parts by mass, more preferably 0.1 to 70 parts by mass, still more preferably 0.2 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, and most preferably 1 to 10 parts by mass, when the total solid content contained in the composition of the present embodiment is 100 parts by mass.
[0230] In the composition of the present embodiment, the hole transport material may be used alone or in combination of two or more.
[0231] (Electron transport material) The electron transport material is classified into a low molecular weight compound and a high molecular weight compound. The electron transport material may have a crosslinking group.
[0232] Examples of the low molecular weight compound include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, and derivatives thereof.
[0233] Examples of the high molecular weight compound include polyphenylene, polyfluorene, and derivatives thereof. The high molecular weight compound may be doped with a metal.
[0234] When the composition of the present embodiment contains an electron transport material that is a low molecular weight compound, the content of the electron transport material is usually 0.01 to 99 parts by mass, preferably 0.05 to 90 parts by mass, more preferably 0.1 to 70 parts by mass, still more preferably 0.2 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, and most preferably 1 to 10 parts by mass, when the total solid content contained in the composition of the present embodiment is 100 parts by mass.
[0235] In the composition of the present embodiment, the electron transport material may be used alone or in combination of two or more kinds.
[0236] (Hole injection material and electron injection material) The hole injection material and the electron injection material are each classified into a low molecular compound and a high molecular compound. The hole injection material and the electron injection material may have a crosslinking group.
[0237] Examples of the low molecular compound 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.
[0238] Examples of the high molecular compound include conductive polymers such as polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, and polyquinoxaline, and derivatives thereof; and polymers containing an aromatic amine structure in the main chain or side chain.
[0239] When the composition of the present embodiment contains a hole injection material that is a low molecular compound or an electron injection material that is a low molecular compound, the content of the hole injection material and the electron injection material is usually 0.01 to 99 parts by mass, preferably 0.05 to 90 parts by mass, more preferably 0.1 to 70 parts by mass, still more preferably 0.2 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, and most preferably 1 to 10 parts by mass, when the total solid content contained in the composition of the present embodiment is 100 parts by mass.
[0240] In the composition of the present embodiment, the hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.
[0241] (Ion doping) When the hole injection material or the electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1×10 -5 S / cm to 1×10 3It is S / cm. In order to set the electric conductivity of the conductive polymer within such a range, an appropriate amount of ions can be doped into the conductive polymer.
[0242] The type of ions to be doped is anions if it is a hole injection material and cations if it is an 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.
[0243] The ions to be doped may be only one kind or two or more kinds.
[0244] (Luminescent material) The luminescent material is classified into a low molecular compound and a high molecular compound. The luminescent material may have a crosslinking group.
[0245] Examples of the low molecular compound include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and luminescent complexes having iridium, platinum, or europium as a central metal.
[0246] Examples of the high molecular compound include high molecular compounds containing a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a group represented by formula (X), a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, etc.
[0247] The luminescent material may contain a low molecular compound and a high molecular compound, and preferably contains a luminescent complex and / or a high molecular compound.
[0248] Examples of the luminescent complex include the metal complexes shown below.
[0249]
Chemical formula
[0250] [Chemical formula]
[0251] [Chemical formula]
[0252] [Chemical formula]
[0253] [Chemical formula]
[0254] When the composition of the present embodiment contains a light-emitting material that is a low-molecular compound, the content of the light-emitting material is usually 0.01 to 99 parts by mass, preferably 0.05 to 90 parts by mass, more preferably 0.1 to 70 parts by mass, still more preferably 0.2 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, and most preferably 1 to 10 parts by mass, when the total amount of solids contained in the composition of the present embodiment is 100 parts by mass.
[0255] The light-emitting material may be used alone or in combination of two or more.
[0256] (Antioxidant) The antioxidant may be a compound that is soluble in the same solvent as the high-molecular compound contained in the composition of the present embodiment and does not inhibit light emission and charge transport. Examples thereof include phenolic antioxidants and phosphorus-based antioxidants.
[0257] When the composition of the present embodiment contains an antioxidant that is a low-molecular compound, the content of the antioxidant is usually 0.000001 to 10 parts by mass when the total amount of solids contained in the composition of the present embodiment is 100 parts by mass.
[0258] The antioxidant may be used alone or in combination of two or more kinds.
[0259] The composition of this embodiment may further contain a solvent. A composition containing at least two or more polymer compounds including a polymer compound (B) and a solvent (hereinafter sometimes referred to as "ink") is suitable for producing a light-emitting element using a printing method such as an inkjet printing method or a nozzle printing method.
[0260] The viscosity of the ink may be adjusted according to the type of the printing method. When applied to a printing method in which a solution such as an inkjet printing method passes through a discharge device, in order to prevent clogging and flight deflection during discharge, it is preferably 1 to 20 mPa·s at 25°C.
[0261] The solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorinated solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide.
[0262] In the ink, when the total content of all the polymer compounds contained in the composition of the present embodiment is 100 parts by mass, the content of the solvent is usually 1000 to 100000 parts by mass, preferably 2000 to 20000 parts by mass.
[0263] The solvent may be used alone or in combination of two or more.
[0264] <Polymer compound in the composition> The ratio (W1) of the content of each polymer compound in the composition of the present embodiment means the mass fraction of the component when the total content of all the polymer compounds contained in the composition of the present embodiment is 1.
[0265] W1 may be, for example, 0.001 or more, 0.01 or more, 0.02 or more, 0.03 or more, 0.04 or more. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.05 or more, more preferably 0.10 or more. Further, W1 may be, for example, less than 1, 0.99 or less, 0.98 or less, 0.97 or less, 0.96 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.80 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably less than 0.80, more preferably 0.79 or less, still more preferably 0.75 or less, and particularly preferably 0.70 or less.
[0266] In one embodiment of the present invention, the said W 1It may be, for example, 0.001 or more and less than 1, 0.001 or more and 0.99 or less, 0.01 or more and 0.98 or less, 0.01 or more and 0.97 or less, 0.02 or more and 0.96 or less, 0.02 or more and 0.95 or less, 0.03 or more and 0.90 or less, 0.03 or more and 0.85 or less, 0.04 or more and 0.80 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 0.05 or more and less than 0.80, more preferably 0.05 or more and 0.79 or less, still more preferably 0.10 or more and 0.75 or less, and particularly preferably 0.10 or more and 0.70 or less.
[0267] In the composition of this embodiment, the ratio (W1 B ) of the content of each polymer compound (B), when the total amount of the contents of all the polymer compounds contained in the composition is taken as 1, may be, for example, 0.01 or more, 0.02 or more, 0.03 or more, 0.04 or more. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 0.05 or more, more preferably 0.10 or more, still more preferably 0.15 or more, particularly preferably 0.20 or more, especially preferably 0.25 or more, especially more preferably 0.30 or more, especially still more preferably 0.35 or more, especially particularly preferably 0.40 or more. Also, in the composition of this embodiment, the ratio (W1 B ) of the content of each polymer compound (B), when the total amount of the contents of all the polymer compounds contained in the composition is taken as 1, may be, for example, less than 1, 0.99 or less, 0.98 or less, 0.97 or less, 0.96 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.80 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably less than 0.80, more preferably 0.79 or less, still more preferably 0.75 or less, and particularly preferably 0.70 or less.
[0268] In one embodiment of the present invention, the W1 B may be, for example, 0.01 or more and less than 1, may be 0.01 or more and 0.99 or less, may be 0.02 or more and 0.98 or less, may be 0.02 or more and 0.97 or less, may be 0.02 or more and 0.96 or less, may be 0.03 or more and 0.95 or less, may be 0.03 or more and 0.90 or less, may be 0.04 or more and 0.85 or less, may be 0.04 or more and 0.80 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 0.05 or more and less than 0.80, more preferably 0.10 or more and less than 0.80, still more preferably 0.15 or more and 0.79 or less, particularly preferably 0.20 or more and 0.79 or less, especially preferably 0.25 or more and 0.75 or less, even more preferably 0.30 or more and 0.75 or less, still more preferably 0.35 or more and 0.70 or less, and particularly preferably 0.40 or more and 0.70 or less.
[0269] In the composition of the present embodiment, when the total content of the polymer compound (B) is set to 1 based on the total amount of the contents of all the polymer compounds contained in the composition, for example, it may be 0.01 or more, may be 0.02 or more, may be 0.03 or more, may be 0.04 or more. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.05 or more, more preferably 0.10 or more, still more preferably 0.15 or more, particularly preferably 0.20 or more, especially preferably 0.25 or more, especially more preferably 0.30 or more, especially still more preferably 0.35 or more, and especially particularly preferably 0.40 or more. Further, in the composition of the present embodiment, when the total content of the polymer compound (B) is set to 1 based on the total amount of the contents of all the polymer compounds contained in the composition, it is 1 or less, for example, it may be less than 1, may be 0.99 or less, may be 0.98 or less, may be 0.97 or less, may be 0.96 or less, may be 0.95 or less, may be 0.90 or less, may be 0.85 or less, may be 0.80 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably less than 0.80, more preferably 0.79 or less, still more preferably 0.75 or less, and particularly preferably 0.70 or less.
[0270] In one embodiment of the present invention, when the total content of the polymer compound (B) in the composition of this embodiment is based on the total amount of the contents of all polymer compounds contained in the composition being 1, for example, it is 0.01 or more and 1 or less, it may be 0.01 or more and less than 1, it may be 0.02 or more and 0.99 or less, it may be 0.02 or more and 0.98 or less, it may be 0.02 or more and 0.97 or less, it may be 0.03 or more and 0.96 or less, it may be 0.03 or more and 0.95 or less, it may be 0.03 or more and 0.90 or less, it may be 0.04 or more and 0.85 or less, it may be 0.04 or more and 0.80 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, preferably it is 0.05 or more and less than 0.80, more preferably it is 0.10 or more and less than 0.80, still more preferably it is 0.15 or more and 0.79 or less, particularly preferably it is 0.20 or more and 0.79 or less, especially preferably it is 0.25 or more and 0.75 or less, even more preferably it is 0.30 or more and 0.75 or less, still more preferably it is 0.35 or more and 0.70 or less, and particularly preferably it is 0.40 or more and 0.70 or less.
[0271] In the composition of this embodiment, the ratio (W1 A ) of the content of each polymer compound (A) is, when the total amount of the contents of all polymer compounds contained in the composition is 1, for example, it may be 0, or it may be more than 0. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, preferably it is 0.01 or more, more preferably it is 0.02 or more, still more preferably it is 0.03 or more, particularly preferably it is 0.04 or more, especially preferably it is 0.05 or more, and even more preferably it is 0.10 or more. Also, in the composition of this embodiment, the ratio (W1 A) When the total content of all the polymer compounds contained in the composition is taken as 1, for example, it may be less than 1, may be 0.99 or less, may be 0.98 or less, may be 0.97 or less, may be 0.96 or less, may be 0.95 or less, may be 0.90 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.85 or less, more preferably 0.80 or less, still more preferably 0.75 or less, particularly preferably 0.70 or less, especially preferably 0.65 or less, especially more preferably 0.60 or less, especially still more preferably 0.55 or less, and especially particularly preferably 0.50 or less.
[0272] In one embodiment of the present invention, the above W1 A may be, for example, 0, or may be more than 0 and less than 1, may be more than 0 and 0.99 or less, may be more than 0 and 0.98 or less, may be more than 0 and 0.97 or less, may be more than 0 and 0.96 or less, may be more than 0 and 0.95 or less, may be more than 0 and 0.90 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.01 or more and 0.85 or less, more preferably 0.01 or more and 0.80 or less, still more preferably 0.02 or more and 0.75 or less, particularly preferably 0.03 or more and 0.70 or less, especially preferably 0.04 or more and 0.65 or less, especially more preferably 0.05 or more and 0.60 or less, especially still more preferably 0.10 or more and 0.55 or less, and especially particularly preferably 0.10 or more and 0.50 or less.
[0273] In the composition of the present embodiment, when the total content of the polymer compound (A) is set to 1 with respect to the total amount of the contents of all the polymer compounds contained in the composition, for example, it may be 0, may exceed 0, may be 0.01 or more, may be 0.02 or more, may be 0.03 or more, may be 0.04 or more, may be 0.05 or more, may be 0.10 or more, may be 0.15 or more, may be 0.20 or more. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably more than 0.20, more preferably 0.21 or more, still more preferably 0.25 or more, and particularly preferably 0.30 or more. Further, in the composition of the present embodiment, when the total content of the polymer compound (A) is set to 1 with respect to the total amount of the contents of all the polymer compounds contained in the composition, for example, it may be less than 1, may be 0.99 or less, may be 0.98 or less, may be 0.97 or less, may be 0.96 or less, may be 0.95 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 0.90 or less, more preferably 0.85 or less, still more preferably 0.80 or less, particularly preferably 0.75 or less, especially preferably 0.70 or less, especially more preferably 0.65 or less, and especially still more preferably 0.60 or less.
[0274] In one embodiment of the present invention, when the total content of the polymer compound (A) in the composition of this embodiment is set to 1 based on the total content of all the polymer compounds contained in the composition, for example, it may be 0, may be more than 0 and less than 1, may be 0.01 or more and less than 1, may be 0.02 or more and 0.99 or less, may be 0.03 or more and 0.99 or less, may be 0.04 or more and 0.98 or less, may be 0.05 or more and 0.97 or less, may be 0.10 or more and 0.96 or less, may be 0.15 or more and 0.95 or less, may be 0.20 or more and 0.95 or less. Since the external quantum efficiency of the light-emitting device of this embodiment is more excellent, it is preferably more than 0.20 and 0.90 or less, more preferably more than 0.20 and 0.85 or less, still more preferably 0.21 or more and 0.80 or less, particularly preferably 0.21 or more and 0.75 or less, especially preferably 0.25 or more and 0.70 or less, and especially more preferably 0.25 or more and 0.65 or less, and especially still more preferably 0.30 or more and 0.60 or less.
[0275] In the composition of this embodiment, the content of all the polymer compounds contained in the composition of this embodiment may be, for example, 1 to 100% by mass based on the total solid content contained in the composition of this embodiment. Since the external quantum efficiency of the light-emitting device of this embodiment is more excellent, it is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 50 to 100% by mass, particularly preferably 70 to 100% by mass, and especially preferably 90 to 100% by mass.
[0276] <X of the composition sp2 > In the composition of this embodiment, the ratio of the content of each polymer compound contained in the composition to the total content of all the polymer compounds contained in the composition is defined as W1, the total molecular weight of all the structural units constituting each polymer compound is defined as M1, and all the structural units constituting each polymer compound have side chains with sp 2 The total number of carbon atoms is C sp2 When defined as such, for each polymer compound, (W1 × C sp2The sum X of the values of (×1000) / M1 sp2 is 15 or less. In the present invention, X of the composition sp2 means the total average number of sp carbon atoms in the side chains per 1000 of the molecular weight of all the polymer compounds contained in the composition. 2 In the present invention, the main chain of the polymer compound means a monocyclic ring constituting the main chain, a condensed ring constituting the main chain, and atoms up to those constituting the main chain, and the side chain of the polymer compound means a group (for example, a substituent) bonded to the main chain.
[0277] Regarding specific examples of the main chain and side chain of the polymer compound in the present invention, the compounds PM5, PM6, and PM7 constituting the polymer compound P1 described later will be described in detail as examples.
[0278] Among the structural units included in the polymer compound P1, in the structural unit corresponding to the compound PM5, the main chain of the polymer compound is a phenylene group constituting the main chain, and the side chain is two hexyl groups. Among the structural units included in the polymer compound P1, in the structural unit corresponding to the compound PM6, the main chain of the polymer compound is two phenylene groups and a 5-membered heterocyclic group constituting the main chain, and the side chain is four methyl groups, two tert-butyl groups, and a bis(3,5-di-tert-butylphenyl)amino group. Among the structural units included in the polymer compound P1, in the structural unit corresponding to the compound PM7, the main chain of the polymer compound is two phenylene groups and a fluorenediyl group constituting the main chain, and the side chain is four methyl groups and two hexylphenyl groups.
[0279] As a result of studying the external quantum efficiency of the light-emitting element, the present inventors have found that the side chain in the polymer compound in the composition used for manufacturing the light-emitting element, particularly the influence of the sp carbon atoms in the side chain, is significant. 2 Regarding the number of sp carbon atoms, further study has revealed that for the sp carbon atoms, 2 the total average number of sp carbon atoms in the side chains per 1000 of the molecular weight of all the polymer compounds contained in the composition 2 X of the composition, which is the total average number of carbon atoms sp2 Surprisingly, it has been found that when X is 15 or less, the external quantum efficiency of a light-emitting device manufactured using the composition can be improved. Incidentally, X of the composition described in Patent Document 1, for which there was room for improvement in external quantum efficiency sp2 was 15.5, and X of the composition described in Patent Document 2 sp2 was 15.8 or 16.0.
[0280] X of the composition sp2 By setting X to 15 or less, the reason why the external quantum efficiency of a light-emitting device manufactured from the composition can be improved is not clear. For example, when X sp2 is reduced to 15 or less, the amount of electrons in the light-emitting device decreases, the balance between the amount of electrons and the amount of holes in the light-emitting device becomes good, and it is conceivable that the external quantum efficiency improves.
[0281] X of the composition of the present embodiment sp2 can be obtained, for example, by the following method. For each constituent unit constituting the polymer compound, the sum of the values obtained by multiplying the molar ratio of that constituent unit to the total moles of all constituent units excluding the end groups by the molecular weight of that constituent unit is defined as M1. For each constituent unit, the total sp 2 carbon atom number of the side chain sp2 is defined as C sp2 Then, X of the composition of the present embodiment sp2 is the sum of (W1 × C
[0282] × 1000) / M1 for each polymer compound. The molecular weights of the constituent units constituting the polymer compound in the composition of the present embodiment can be calculated, for example, using the Molecular Weight value of ChemDraw (manufactured by Huerinks).
[0283] The total sp 2 carbon atom number (C sp2 ) of the side chains possessed by all the constituent units constituting the polymer compound in the composition of the present embodiment refers to the sp contained in substituents other than the atoms, monocycles, and condensed rings that form the main chain of each polymer compound contained in the composition.2 Means the total number of carbon atoms.
[0284] X of the composition of this embodiment sp2 A specific calculation method will be described in detail by taking as an example a composition of a polymer compound P1, a polymer compound P2, and a polymer compound P3 described later (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40% by mass / 50% by mass / 10% by mass, hereinafter also referred to as "composition (A)").
[0285] The ratio of the content of each polymer compound in the composition (A) is as follows. W1 P1 = 0.40 W1 P2 = 0.50 W1 P3 = 0.10 [In the formula, W1 P1 represents the ratio of the content of the polymer compound P1 in the composition (A), W1 P2 represents the ratio of the content of the polymer compound P2 in the composition (A), and W1 P3 represents the ratio of the content of the polymer compound P3 in the composition (A).]
[0286] The polymer compound P1 is a copolymer in which the structural units derived from the compound PM5, the structural units derived from the compound PM6, and the structural units derived from the compound PM7 are composed in a molar ratio of 45:5:50 based on the theoretical values obtained from the amounts of the charged raw materials. The molecular weight of the structural unit derived from the compound PM5 is 244.42, the molecular weight of the structural unit derived from the compound PM6 is 978.27, and the molecular weight of the structural unit derived from the compound PM7 is 693.03. The sp 2 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM5 is 0, and the sp 2 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM6 is 12, and the sp 2 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM7 is 12. The structural units derived from compound PM5 and compound PM7 are both structural units represented by formula (Y), and the structural unit derived from compound PM6 is a structural unit represented by structural unit (B).
[0287] In terms of the theoretical value determined from the amount of the charged raw materials, the polymer compound P2 is a copolymer composed of the structural unit derived from compound PM3 and the structural unit derived from compound PM8 at a molar ratio of 70:30. The molecular weight of the structural unit derived from compound PM3 is 388.64, and the molecular weight of the structural unit derived from compound PM8 is 104.15. The sp 2 number of carbon atoms in the side chain contained in the structural unit derived from compound PM3 is 0, and the sp 2 number of carbon atoms in the side chain contained in the structural unit derived from compound PM8 is 0. The structural units derived from compound PM3 and compound PM8 are both structural units represented by formula (Y).
[0288] In terms of the theoretical value determined from the amount of the charged raw materials, the polymer compound P3 is a copolymer composed of the structural unit derived from compound PM10, the structural unit derived from compound PM9, and the structural unit derived from compound PM11 at a molar ratio of 50:20:30. The molecular weight of the structural unit derived from compound PM10 is 789.12, the molecular weight of the structural unit derived from compound PM9 is 789.12, and the molecular weight of the structural unit derived from compound PM11 is 925.19. The sp 2 number of carbon atoms in the side chain contained in the structural unit derived from compound PM10 is 36, the sp 2 number of carbon atoms in the side chain contained in the structural unit derived from compound PM9 is 36, and the sp 2 number of carbon atoms in the side chain contained in the structural unit derived from compound PM11 is 60. The structural units derived from compound PM10, compound PM9, and compound PM11 are all structural units represented by formula (Y).
[0289] The sum of the molecular weights of all the constituent units constituting the polymer compound is determined as follows. M1 P1 =(244.42×0.45)+(978.27×0.05)+(693.03×0.50)=505.42 M1 P2 =(388.64×0.70)+(104.15×0.30)=303.29 M1 P3 =(789.12×0.50)+(789.12×0.20)+(925.19×0.30)=829.94 [In the formula, M1 P1 represents the sum of the molecular weights of all the constituent units constituting the polymer compound P1, M1 P2 represents the sum of the molecular weights of all the constituent units constituting the polymer compound P2, M1 P3 represents the sum of the molecular weights of all the constituent units constituting the polymer compound P3.]
[0290] The total number of sp 2 carbon atoms in the side chains possessed by all the constituent units constituting the polymer compound is determined as follows. C sp2,P1 =(0×0.45)+(12×0.05)+(12×0.50)=6.6 C sp2,P2 =(0×0.70)+(0×0.30)=0 C sp2,P3 =(36×0.50)+(36×0.20)+(60×0.30)=43.2 [In the formula, C sp2,P1 represents the total number of sp 2 carbon atoms in the side chains possessed by all the constituent units constituting the polymer compound P1, C sp2,P2 represents the total number of sp 2 carbon atoms in the side chains possessed by all the constituent units constituting the polymer compound P2, C sp2,P3 represents the total number of sp 2 carbon atoms in the side chains possessed by all the constituent units constituting the polymer compound P3.]
[0291] X of the composition (A) sp2 is determined as follows. X sp2 =(W1P1 ×C sp2,P1 ×1000) / M1 P1 +(W1 P2 ×C sp2,P2 ×1000) / M1 P2 +(W1 P3 ×C sp2,P3 ×1000) / M1 P3 =(0.40×6.6×1000) / 505.42+(0.50×0×1000) / 303.29+(0.10×43.2×1000) / 829.94 = 10.4
[0292] <X of the composition sp3 > In the present invention, X of the composition sp3 means the total average number of sp carbon atoms in the side chains per 1000 of the molecular weight of all the polymer compounds contained in the composition. 3 X of the composition of the present embodiment sp3 can be determined, for example, by the following method. For each structural unit constituting the polymer compound, the sum of the values obtained by multiplying the molar ratio of the structural unit to the total moles of all the structural units excluding the end groups by the molecular weight of the structural unit is defined as M1, and the total number of sp carbon atoms in the side chains determined for each structural unit is C 3 sp3 Then, X of the composition of the present embodiment sp3 is the sum of (W1×Csp3×1000) / M1 in each polymer compound.
[0293] The total number of sp carbon atoms in the side chains possessed by all the structural units constituting the polymer compound in the composition of the present embodiment (C 3 ) means the total number of sp carbon atoms contained in substituents other than the atoms, monocycles, and condensed rings forming the main chain of each polymer compound contained in the composition. sp3 3
[0294] X of the composition of the present embodiment sp3 The calculation method of sp2 is the same as that used for calculating X of the composition, except that "sp 2 carbon atom number" is replaced by "sp3 Except for using the "number of carbon atoms", the X of the composition is calculated sp2 in the same way as the calculation method of X of the composition, and X of the composition sp3 can be calculated. A specific calculation method will be described in detail by taking the composition (A) as an example.
[0295] In the polymer compound P1, the number of sp3 carbon atoms in the side chain contained in the structural unit derived from the compound PM5 is 12, and the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM6 is 28, and the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM7 is 16.
[0296] In the polymer compound P2, the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM3 is 16, and the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM8 is 2.
[0297] In the polymer compound P3, the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM10 is 12, and the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM9 is 12, and the sp 3 number of carbon atoms in the side chain contained in the structural unit derived from the compound PM11 is 0.
[0298] The total number of sp 3 carbon atoms in the side chains possessed by all the structural units constituting the polymer compound is obtained as follows. C sp3,P1 =(12×0.45)+(28×0.05)+(16×0.50)=14.8 C sp3,P2 =(16×0.70)+(2×0.30)=11.8 C sp3,P3 =(12×0.50)+(12×0.20)+(0×0.30)=8.4 [In the formula, C sp3,P1 is the sp of the side chains possessed by all the structural units constituting the polymer compound P13 Total number of carbon atoms, C sp3,P2 is the sp of the side chain possessed by all the constituent units constituting the polymer compound P2 3 Total number of carbon atoms, C sp3,P3 is the sp of the side chain possessed by all the constituent units constituting the polymer compound P3 3 represents the total number of carbon atoms.]
[0299] X of the composition (A) sp3 is determined as follows. X sp3 =(W1 P1 ×C sp3,P1 ×1000) / M1 P1 +(W1 P2 ×C sp3,P2 ×1000) / M1 P2 +(W1 P3 ×C sp3,P3 ×1000) / M1 P3 =(0.40×14.8×1000) / 505.42+(0.50×11.8×1000) / 303.29+(0.10×8.4×1000) / 829.94=32.2
[0300] C sp2 may be, for example, 0 or more and 5000 or less, 0 or more and 2000 or less, 0 or more and 1000 or less, 0 or more and 500 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent and the production of the polymer compound of this embodiment is easy, it is preferably 0 or more and 200 or less, more preferably 0 or more and 150 or less, still more preferably 0 or more and 100 or less, particularly preferably 0 or more and 80 or less, especially preferably 0 or more and 60 or less, especially more preferably 0 or more and 50 or less, and especially still more preferably 0 or more and 45 or less.
[0301] Since M1 has a more excellent external quantum efficiency of the light-emitting element of the present embodiment and an excellent stability of the polymer compound of the present embodiment, it is preferably 100 or more, more preferably 150 or more, still more preferably 200 or more, particularly preferably 250 or more, and especially preferably 300 or more. Further, M1 may be, for example, 10000 or less, 8000 or less, 6000 or less, or 4000 or less. Since the light-emitting element of the present embodiment has a more excellent external quantum efficiency and the production of the polymer compound of the present embodiment is easy, it is preferably 2000 or less, more preferably 1500 or less, still more preferably 1000 or less.
[0302] In one embodiment of the present invention, M1 may be, for example, 100 or more and 10000 or less, 100 or more and 8000 or less, 100 or more and 6000 or less, or 100 or more and 4000 or less. Since the light-emitting element of the present embodiment has a more excellent external quantum efficiency, it is preferably 100 or more and 2000 or less, more preferably 150 or more and 2000 or less, still more preferably 200 or more and 1500 or less, particularly preferably 250 or more and 1500 or less, and especially preferably 300 or more and 1000 or less.
[0303] C sp3 For example, C may be more than 0, 0.01 or more, 0.1 or more, or 0.5 or more. Since the light-emitting element of the present embodiment has a more excellent external quantum efficiency and the solubility of the polymer compound of the present embodiment is excellent, it is preferably 1 or more, more preferably 3 or more, still more preferably 5 or more, particularly preferably 7 or more, and especially preferably 8 or more. Further, C sp3For example, it may be 5000 or less, 2000 or less, 1000 or less, 500 or less, 200 or less, 150 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent and the production of the polymer compound of the present embodiment is easy, it is preferably 100 or less, more preferably 80 or less, still more preferably 60 or less, particularly preferably 50 or less, especially preferably 40 or less, especially more preferably 30 or less, especially still more preferably 20 or less, especially particularly preferably 15 or less.
[0304] In one embodiment of the present invention, the above-mentioned C sp3 For example, it may be more than 0 and 5000 or less, 0.01 or more and 2000 or less, 0.1 or more and 1000 or less, 0.1 or more and 500 or less, 0.5 or more and 200 or less, 0.5 or more and 150 or less. Since the external quantum efficiency of the light-emitting element of the present embodiment is more excellent, it is preferably 1 or more and 100 or less, more preferably 3 or more and 80 or less, still more preferably 5 or more and 60 or less, particularly preferably 5 or more and 50 or less, especially preferably 7 or more and 40 or less, especially more preferably 7 or more and 30 or less, especially still more preferably 8 or more and 20 or less, especially particularly preferably 8 or more and 15 or less.
[0305] <X of the composition sp2 / X sp3 > In the present invention, X of the composition sp2 / X sp3 means the ratio of the number of sp 3 carbon atoms in the side chains of all the polymer compounds contained in the composition to the number of sp 2 carbon atoms in the side chains of all the polymer compounds contained in the composition.
[0306] X of the composition of the present embodiment sp2 / X sp3 The specific calculation method of will be described in detail by taking the composition (A) as an example.
[0307] X of composition (A) sp2 / X sp3 is determined as follows. X sp2 / X sp3 =10.4 / 32.2 = 0.32
[0308] In the composition of this embodiment, X of the composition sp2 is 15 or less, and for example, it may be less than 15. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 14.8 or less, more preferably 14.6 or less, and still more preferably 14.5 or less. Also, in the composition of this embodiment, X of the composition sp2 may be, for example, 0 or more, more than 0, 0.1 or more, 0.2 or more, 0.5 or more, 1 or more, 2 or more, 3 or more. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 5 or more, more preferably 6 or more, still more preferably 7 or more, particularly preferably 8 or more, especially preferably 9 or more, and especially more preferably 10 or more. When X of the composition sp2 is below the above upper limit, it is easy to improve the external quantum efficiency of the light-emitting element of this embodiment. Also, when X of the composition sp2 is above the above lower limit, it is easy to improve the external quantum efficiency of the light-emitting element of this embodiment.
[0309] In one embodiment of the present invention, in the composition of this embodiment, X of the composition sp2 may be 0 or more and 15 or less, 1 or more and 15 or less, 2 or more and 15 or less, 3 or more and 15 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 5 or more and 15 or less, more preferably 7 or more and 14.8 or less, still more preferably 9 or more and 14.6 or less, and particularly preferably 10 or more and 14.5 or less.
[0310] In the composition of this embodiment, X of the composition sp2 / X sp3may be, for example, 100 or less, 50 or less, 20 or less, 10 or less, 7 or less, 5 or less, 3 or less, 1 or less, 0.80 or less, 0.60 or less, 0.55 or less. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably less than 0.55, more preferably 0.54 or less, still more preferably 0.52 or less, particularly preferably 0.50 or less, and especially preferably 0.49 or less. Further, in the composition of this embodiment, X of the composition sp2 / X sp3 may be, for example, 0 or more, more than 0, 0.01 or more, 0.05 or more, 0.10 or more, 0.15 or more. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably 0.20 or more, more preferably 0.25 or more, still more preferably 0.30 or more, and particularly preferably 0.32 or more. X of the composition sp2 / X sp3 being below the above upper limit makes it easy to improve the external quantum efficiency of the light-emitting element of this embodiment. Also, when X of the composition sp2 / X sp3 is above the above lower limit, it is easy to improve the external quantum efficiency of the light-emitting element of this embodiment.
[0311] In one embodiment of the present invention, in the composition of this embodiment, X of the composition sp2 / X sp3 may be, for example, from 0 to 100, from 0.01 to 10, from 0.05 to 5, from 0.1 to 1, from 0.15 to 0.55. Since the external quantum efficiency of the light-emitting element of this embodiment is more excellent, it is preferably from 0.20 to less than 0.55, more preferably from 0.30 to 0.50, still more preferably from 0.32 to 0.49.
[0312] [Film] The composition of this embodiment is suitably used for manufacturing a film. The film comprises the composition of this embodiment.
[0313] The film is suitable as a light-emitting layer in a light-emitting device.
[0314] The film can be produced using ink, for example, by 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.
[0315] The thickness of the film is usually 1 nm to 10 μm.
[0316] [Light-emitting device] The light-emitting device of this embodiment is a light-emitting device containing the composition of this embodiment. As the configuration of the light-emitting device of this embodiment, for example, it has electrodes composed of an anode and a cathode, and a layer containing the composition of this embodiment provided between the electrodes.
[0317] [Layer structure] The layer containing the composition of this embodiment is usually one or more of a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, preferably a light-emitting layer. Each of these layers contains a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material. Each of these layers can dissolve the light-emitting material, the hole transport material, the hole injection material, the electron transport material, and the electron injection material in the above-mentioned solvent to prepare ink for use, and can be formed using the same method as the production of the above-mentioned film.
[0318] The light-emitting element has a light-emitting layer between an anode and a cathode. From the viewpoints of hole injection property and hole transport property, the light-emitting element of the present embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light-emitting layer, and from the viewpoints of electron injection property and electron transport property, it preferably has at least one layer of an electron injection layer and an electron transport layer between the cathode and the light-emitting layer.
[0319] Examples of the materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer, and electron injection layer include, in addition to the compositions of the present embodiment, the above-described hole transport material, electron transport material, light-emitting material, hole injection material, and electron injection material, respectively.
[0320] When the materials for the hole transport layer, electron transport layer, and light-emitting layer are dissolved in the solvent used for forming the layers adjacent to the hole transport layer, electron transport layer, and light-emitting layer, respectively, in the production of the light-emitting element, it is preferable that the materials have a crosslinking group in order to avoid the dissolution of the materials in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
[0321] In the light-emitting element of the present embodiment, as the formation method of each layer such as the light-emitting layer, hole transport layer, electron transport layer, hole injection layer, and electron injection layer, when using a low molecular compound, for example, a vacuum evaporation method from powder, a method by film formation from a solution or a molten state can be mentioned, and when using a high molecular compound, for example, a method by film formation from a solution or a molten state can be mentioned.
[0322] The order, number, and thickness of the laminated layers are adjusted in consideration of the external quantum efficiency and luminance lifetime.
[0323] [Substrate / Electrode] The substrate in the light-emitting element may be a substrate on which an electrode can be formed and that does not chemically change when an organic layer is formed, for example, a substrate made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, it is preferable that the electrode farthest from the substrate is transparent or translucent.
[0324] Examples of the anode material include conductive metal oxides and translucent metals. Preferably, they are indium oxide, zinc oxide, tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; a composite of silver, palladium, and copper (APC); NESA, gold, platinum, silver, and copper.
[0325] Examples of the cathode material include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of them; alloys of one or more of them and one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the 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 the cathode may each have a laminated structure of two or more layers.
[0326] [Use] In order to obtain planar light emission using a light-emitting element, a planar anode and cathode may be arranged to overlap. In order to obtain patterned light emission, there are a method of installing a mask provided with a patterned window on the surface of a planar light-emitting element, a method of forming a layer to be a non-light-emitting portion extremely thick to make it substantially non-light-emitting, and a method of forming the anode or cathode, or both electrodes, in a pattern. By forming a pattern by any of these methods and arranging some electrodes so that they can be independently turned on and off, a segment type display device capable of displaying numbers, characters, etc. can be obtained. In order to obtain a dot matrix display device, both the anode and cathode may be formed in stripe shapes and arranged to be orthogonal. By a method of separately coating a plurality of types of polymer compounds having different emission colors or a method using a color filter or a fluorescence conversion filter, partial color display and multi-color display are possible. The dot matrix display device can be driven passively or can be driven actively in combination with a TFT or the like. These display devices can be used for displays of computers, televisions, mobile terminals, etc. The planar light-emitting element can be suitably used as a planar light source for the backlight of a liquid crystal display device or as a planar illumination light source. By using a flexible substrate, it can also be used as a curved light source and display device.
Example
[0327] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.
[0328] In the examples, the number average molecular weight (Mn) in terms of polystyrene and the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound were determined by the following size exclusion chromatography (SEC) using tetrahydrofuran in the mobile phase. The measurement conditions for SEC are as follows.
[0329] <Measurement conditions> The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 μL was injected into SEC. The mobile phase was flowed at a flow rate of 1.0 mL / min. As the column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. As the detector, a UV-VIS detector (manufactured by Tosoh Corporation, product name: UV-8320GPC) was used.
[0330] NMR was measured by the following method. 5 to 10 mg of the measurement sample was dissolved in about 0.5 mL of deuterated chloroform (CDCl3), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol or deuterated methylene chloride, and measured using an NMR apparatus (manufactured by Agilent, product name: INOVA300 or MERCURY 400VX).
[0331] As an index of the purity of the compound, the value of the HPLC area percentage was used. This value was taken as the value at UV = 254 nm in HPLC (manufactured by Shimadzu Corporation, product name: LC-20A) unless otherwise specified. At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2% by weight, and 1 to 10 μL was injected into HPLC according to the concentration. The mobile phase of HPLC was used while changing the ratio of acetonitrile / tetrahydrofuran from 100 / 0 to 0 / 100 (volume ratio), and flowed at a flow rate of 1.0 mL / min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance was used. As the detector, a photodiode array detector (manufactured by Shimadzu Corporation, product name: SPD-M20A) was used.
[0332] <Synthesis Examples PM1 to PM11: Synthesis and Obtaining of Compounds PM1 to PM11> Compound PM1 was synthesized according to the method described in JP-A-2011-174062. Compound PM2 was synthesized according to the method described in WO 2005 / 049546. Compound PM3 was synthesized according to the method described in International Publication No. 2002 / 045184. Compound PM4 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2008-106241. Compound PM5 was synthesized according to the method described in Japanese Patent Application Laid-Open No. 2010-189630. Compound PM6 was synthesized according to the method described in International Publication No. 2019 / 004248. Compound PM7 was synthesized according to the method described in International Publication No. 2015 / 008851. Compound PM8 manufactured by Tokyo Chemical Industry Co., Ltd. was used. Compounds PM9 and PM10 were synthesized according to the method described in International Publication No. 2022 / 181075.
[0333]
Chemical formula
[0334]
Chemical formula
[0335]
Chemical formula
[0336]
Chemical formula
[0337] <Synthesis Example 1> Synthesis of Compound PM11
Chemical formula
[0338] (Stage 1: Synthesis of Compound PM11B) After making the inside of the reaction vessel a nitrogen atmosphere, compound PM11A (19.2 g) and dichloromethane (285 mL) were added, and the mixture was cooled to 0°C. To this, sulfuric acid (8.7 g) was slowly added, and the mixture was stirred at 0°C for 1 hour. To this, a solution prepared by dissolving iodine monochloride (41.46 g) in dichloromethane (95 mL) was slowly added dropwise, and the mixture was stirred at 0°C for 1 hour. After dropping an aqueous sodium sulfite solution, the temperature was raised to room temperature. Dichloromethane was added, and the obtained organic layer was separated and washed 4 times with ion-exchanged water. After adding magnesium sulfate for dehydration, filtration was performed, and the obtained solution was concentrated under reduced pressure to obtain a crude product. By washing the crude product with methanol, compound PM11B (25.9 g) was obtained as a white solid. The HPLC area percentage value of compound PM11B was 99.5% or more.
[0339] (Stage2: Synthesis of compound PM11C) After making the inside of the reaction vessel a nitrogen atmosphere, compound PM11B (24.33 g), 3-biphenylboronic acid (24.75 g), tetrakis(triphenylphosphine)palladium(0) (3.44 g), potassium carbonate (49.35 g), ion-exchanged water (243 mL), ethanol (73 mL), and toluene (243 mL) were added, and the mixture was stirred at 75°C for 22 hours. After cooling the obtained reaction solution to room temperature, filtration was performed using a filter pad with celite, and the aqueous layer was removed from the obtained filtrate. After washing the obtained organic layer with ion-exchanged water, filtration was performed, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized from a mixed solvent of toluene / ethanol and dried under reduced pressure at 50°C to obtain compound PM11C (22.0 g). The LC area percentage value of compound PM11C was 99.5% or more. This operation was repeated to obtain a required amount of compound PM11C.
[0340] (Stage3: Synthesis of compound PM11D) After setting the inside of the reaction vessel to a nitrogen atmosphere, compound PM11C (56.04 g) and tetrahydrofuran (715 mL) were added, and the mixture was cooled to -70°C. Thereto, 1.0 M sec-butyllithium n-hexane / cyclohexane solution (1021 mL) was slowly added, and the mixture was stirred at -70°C for 1 hour. Thereto, compound PM9A (20.43 g) and tetrahydrofuran (305 mL) were slowly added dropwise, and then the mixture was stirred at -65°C for 1 hour. After slowly adding methanol, the resulting reaction solution was brought to room temperature, ion-exchanged water and toluene were added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, dried over magnesium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (a mixed solvent of toluene and n-hexane) and dried under reduced pressure at 50°C to obtain compound PM11D (56.6 g). The LC area percentage value of compound PM11D was 99.5% or more.
[0341] (Stage 4: Synthesis of compound PM11) After setting the inside of the reaction vessel to a nitrogen atmosphere, compound PM11D (30.6 g) and toluene (920 mL) were added, and the mixture was cooled to 0°C. Thereto, sulfuric acid (2.7 g) was slowly added, and the mixture was stirred at 0°C for 2 hours. Ion-exchanged water was slowly added, and after cooling the resulting reaction solution to room temperature, the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized from a mixed solvent of toluene / acetonitrile and dried under reduced pressure at 50°C to obtain compound PM11 (26.1 g). The LC area percentage value of compound PM11 was 99.5% or more.
[0342] <Synthesis Example 2> Synthesis of Polymer Compound IP1 Polymer compound IP1 was synthesized by the method described in JP-A-2012-144722 using compound PM1, compound PM2, compound PM3, and compound PM4. The Mn of polymer compound IP1 was 7.6×10 4 and the Mw was 3.2×10 5
[0343] In terms of the theoretical value determined from the amounts of the charged raw materials, the polymer compound IP1 is a copolymer composed of a structural unit derived from the compound PM1, a structural unit derived from the compound PM2, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM4, with a molar ratio of 50:30:12.5:7.5.
[0344] <Synthesis Example 3> Synthesis of Polymer Compound P1 After making the inside of the reaction vessel an inert gas atmosphere, compound PM5 (0.3070 g), compound PM7 (0.6403 g), compound PM6 (0.0927 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.27 mg), and toluene (31 mL) were added and heated to 80°C. Then, a 20% by mass aqueous solution of tetraethylammonium hydroxide (15.7 g) was added dropwise thereto and refluxed for 6 hours. Then, phenylboronic acid (45.7 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.27 mg) were added thereto and stirred at 80°C for 3 hours. After cooling the reaction mixture, an aqueous solution of sodium diethyldithiocarbamate was added and stirred at 40°C for 1 hour. After cooling the reaction solution and removing the aqueous layer, the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. When the obtained solution was dropped into methanol and stirred, a precipitate was formed. The precipitate was dissolved in toluene (44 mL), alumina (27 g) was added and stirred for 3 hours, and then the obtained suspension was purified by passing it through a silica gel column. When the obtained solution was dropped into methanol and stirred, a precipitate was formed. The precipitate was collected by filtration and dried to obtain 0.52 g of the polymer compound P1. The Mn of the polymer compound P1 was 6.3×10 4 and the Mw was 1.5×10 5 5 It was.
[0345] In terms of the theoretical value determined from the amounts of the charged raw materials, the polymer compound P1 is a copolymer composed of a structural unit derived from the compound PM5, a structural unit derived from the compound PM6, and a structural unit derived from the compound PM7, with a molar ratio of 45:5:50.
[0346] <Synthesis Example 4> Synthesis of Polymer Compound P2 The polymer compound P2 was synthesized by the method described in JP-A-2004-2654 using the compound PM3 and the compound PM8. The Mn of the polymer compound P2 was 1.7×10 5 and the Mw was 5.0×10 5 .
[0347] The polymer compound P2 is a copolymer in which the structural unit derived from the compound PM3 and the structural unit derived from the compound PM8 are composed at a molar ratio of 70:30, based on the theoretical value calculated from the amounts of the charged raw materials.
[0348] <Synthesis Example 5> Synthesis of Polymer Compound P3 After making the inside of the reaction vessel an inert gas atmosphere, 2.57 g of the compound PM10, 1.18 g of the compound PM9, 2.00 g of the compound PM11, 0.22 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, and 180 mL of toluene were added and heated to 80°C. To the reaction solution, an aqueous solution of 20% by mass tetraethylammonium hydroxide (83 mL) was added dropwise and refluxed for 3 hours. After the reaction, 0.10 g of phenylboronic acid and 0.15 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto and refluxed for 3 hours. Then, the reaction solution was cooled to room temperature, the aqueous layer was removed, and then washed once with ion-exchanged water, once with a 0.15% by mass aqueous solution of sodium N,N-diethyldithiocarbamate, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained solution was dehydrated under reduced pressure to obtain a toluene solution from which water was removed. This toluene solution was purified by passing it through an alumina column through which toluene had been previously passed. When the purified solution was dropped into methanol and stirred, a precipitate was formed, so the precipitate was collected by filtration and dried to obtain 1.18 g of the polymer compound P3. The Mn of the polymer compound P3 was 4.1×10 4 and the Mw was 7.9×10 4 .
[0349] In terms of the theoretical value determined from the amount of charged raw materials, the polymer compound P3 is a copolymer composed of a structural unit derived from the compound PM10, a structural unit derived from the compound PM9, and a structural unit derived from the compound PM11 at a molar ratio of 50:20:30.
[0350] <Example D1> (Formation of Anode and Hole Injection Layer) An anode was formed by forming an ITO film on a glass substrate with a thickness of 45 nm by sputtering. ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was spin-coated on the anode with a thickness of 35 nm and heated on a hot plate at 240 °C for 15 minutes in an air atmosphere. Thereby, a hole injection layer was formed.
[0351] (Formation of Hole Transport Layer) Polymer compound IP1 was dissolved in xylene at a concentration of 0.70% by mass. Using the obtained xylene solution, a film was formed on the hole injection layer with a thickness of 20 nm by spin coating, and a hole transport layer was formed by heating on a hot plate at 200 °C for 30 minutes in a nitrogen gas atmosphere.
[0352] (Formation of Light Emitting Layer) Polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40% by mass / 50% by mass / 10% by mass) were dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film was formed on the hole transport layer with a thickness of 60 nm by spin coating, and a light emitting layer was formed by heating at 170 °C for 10 minutes in a nitrogen gas atmosphere.
[0353] (Formation of Cathode) The substrate on which the light emitting layer was formed was depressurized to 1.0×10 -4 Pa or less in an evaporation apparatus, and then, as a cathode, about 4 nm of sodium fluoride was evaporated on the light emitting layer, and then about 80 nm of aluminum was evaporated on the sodium fluoride layer. After evaporation, the glass substrate was used for sealing to fabricate a light emitting device D1.
[0354] (Evaluation of Light-Emitting Element) By applying a voltage to the light-emitting element D1, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. The current density was 1 mA / cm 2 and the device was driven at a constant current to measure the external quantum efficiency.
[0355] For the composition of the polymer compound P1, the polymer compound P2, and the polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40 mass% / 50 mass% / 10 mass%) in Example D1, X sp2 was 10.4, and X sp2 / X sp3 was 0.32.
[0356] <Example D2> Fabrication and Evaluation of Light-Emitting Element D2 A light-emitting element D2 was fabricated in the same manner as in Example D1, except that "the polymer compound P1, the polymer compound P2, and the polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 50 mass% / 40 mass% / 10 mass%)" was used instead of "the polymer compound P1, the polymer compound P2, and the polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40 mass% / 50 mass% / 10 mass%)" in Example D1.
[0357] By applying a voltage to the light-emitting element D2, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. The current density was 1 mA / cm 2 and the device was driven at a constant current to measure the external quantum efficiency.
[0358] For the composition of the polymer compound P1, the polymer compound P2, and the polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 50 mass% / 40 mass% / 10 mass%) in Example D2, X sp2 was 11.7, and X sp2 / X sp3 was 0.38.
[0359] <Example D3> Fabrication and Evaluation of Light-Emitting Element D3 In Example D1, an EL element D3 was fabricated in the same manner as in Example D1, except that “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 60% by mass / 30% by mass / 10% by mass)” was used instead of “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40% by mass / 50% by mass / 10% by mass)”.
[0360] By applying a voltage to the EL element D3, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. The current density was set to 1 mA / cm 2 and the device was driven at a constant current, and the external quantum efficiency was measured.
[0361] In Example D3, the X value of the composition of polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 60% by mass / 30% by mass / 10% by mass) sp2 was 13.0, and the value of X sp2 / X sp3 was 0.43.
[0362] <Example D4> Fabrication and Evaluation of EL Element D4 In Example D1, an EL element D4 was fabricated in the same manner as in Example D1, except that “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 70% by mass / 20% by mass / 10% by mass)” was used instead of “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40% by mass / 50% by mass / 10% by mass)”.
[0363] By applying a voltage to the EL element D4, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. The current density was set to 1 mA / cm 2 and the device was driven at a constant current, and the external quantum efficiency was measured.
[0364] In Example D4, X of the composition of polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 70% by mass / 20% by mass / 10% by mass) sp2 is 14.3, and X sp2 / X sp3 is 0.49.
[0365] <Comparative Example CD1> Fabrication and Evaluation of Light-Emitting Element CD1 A light-emitting element CD1 was fabricated in the same manner as in Example D1, except that “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 80% by mass / 10% by mass / 10% by mass)” was used instead of “polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 40% by mass / 50% by mass / 10% by mass)” in Example D1.
[0366] By applying a voltage to the light-emitting element CD1, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. The current density was 1 mA / cm 2 and the device was driven at a constant current to measure the external quantum efficiency.
[0367] In Comparative Example CD1, X of the composition of polymer compound P1, polymer compound P2, and polymer compound P3 (polymer compound P1 / polymer compound P2 / polymer compound P3 = 80% by mass / 10% by mass / 10% by mass) sp2 is 15.7, and X sp2 / X sp3 is 0.55.
[0368] <Comparative Example CD2> Fabrication and Evaluation of Light-Emitting Element CD2 In Example D1, except that “Polymer Compound P1, Polymer Compound P2, and Polymer Compound P3 (Polymer Compound P1 / Polymer Compound P2 / Polymer Compound P3 = 40% by mass / 50% by mass / 10% by mass)” was replaced with “Polymer Compound P1, Polymer Compound P2, and Polymer Compound P3 (Polymer Compound P1 / Polymer Compound P2 / Polymer Compound P3 = 85% by mass / 5% by mass / 10% by mass)”, a light-emitting element CD2 was fabricated in the same manner as in Example D1.
[0369] By applying a voltage to the light-emitting element CD2, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. At a current density of 1 mA / cm 2 it was driven at a constant current, and the external quantum efficiency was measured.
[0370] In Comparative Example CD2, X of the composition of Polymer Compound P1, Polymer Compound P2, and Polymer Compound P3 (Polymer Compound P1 / Polymer Compound P2 / Polymer Compound P3 = 80% by mass / 10% by mass / 10% by mass) sp2 was 16.3, and X sp2 / X sp3 was 0.59.
[0371] The results of Examples D1 to D4, Comparative Examples CD1 and CD2 are shown in Table 3. In Table 3, the external quantum efficiency indicates the relative values of the external quantum efficiencies of light-emitting elements D1 to D4 and CD2 when the external quantum efficiency of light-emitting element CD1 is taken as 1.0.
[0372]
Table 3
Claims
1. A composition containing two or more kinds of polymer compounds, wherein at least one of the two or more kinds of polymer compounds is a polymer compound (B). The polymer compound (B) is a polymer compound containing a structural unit (B) having a group obtained by removing one or more hydrogen atoms from a low molecular compound (B) having a condensed heterocyclic skeleton (b) containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an sp 3 carbon atom and a nitrogen atom in the ring, Let W be the ratio of the content of each polymer compound contained in the composition to the total content of all the polymer compounds contained in the composition. 1 Let M be the total molecular weight of all the constituent units constituting each polymer compound. 1 Let C be the total number of sp 2 carbon atoms in the side chains possessed by all the constituent units constituting each polymer compound. sp2 When 1 the sum X sp2 of (W × C × 1000) / M 1 for each polymer compound is 15 or less, the composition. sp2
2. wherein at least one of the two or more kinds of polymer compounds is a polymer compound (A), and the polymer compound (A) is a polymer compound containing at least one structural unit selected from the group consisting of a structural unit represented by formula (Y) and a structural unit represented by formula (X). The composition according to claim 1. 【Chemical 1】 [In the formula, Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have substituents. 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 respectively bonded.] 【Chemical 2】 [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 substituents. When a plurality of these 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 each 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 substituents. When there are a plurality of these 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 each bonded. Ar X2 When there are a plurality of them, they may be the same or different from each other. Ar X4 When there are a plurality of them, they may be the same or different from each other. R X1 、 R X2 and R X3 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 substituents. 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 respectively bonded. When there are a plurality of R X2 's, they may be the same or different. When there are a plurality of R X3 's, they may be the same or different. ]
3. The composition according to claim 1, wherein the condensed heterocyclic skeleton (b) contains, in the ring, a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom.
4. The composition according to claim 3, wherein the condensed heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.
5. The composition according to claim 1, wherein the low molecular compound (B) is a compound represented by formula (1-1), a compound represented by formula (1-2), or a compound represented by formula (1-3). 【Chemical 3】 [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 substituents. When a plurality of these 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 each 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 substituents. When a plurality of these 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 respectively bonded. Y 2 and Y 3 each independently represents 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 substituents. When a plurality of these 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 respectively 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 substituents. When a plurality of these 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 respectively bonded. When a plurality of Ry are present, they may be the same or different. Y 1 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. Y 1 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. Y 2 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. Y 2 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring. Y 3 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. Y 3 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring. ]
6. said Y 1 said Y 2 and said Y 3 The composition according to claim 5, wherein said Y, said Y and said Y are each a group represented by an oxygen atom, a sulfur atom or -N(Ry)-.
7. Said Y 1 、said Y 2 and said Y 3 is a group represented by -N(Ry)-, the composition according to claim 6.
8. The composition according to claim 1, wherein the structural unit (B) is a structural unit represented by formula (BP-1), a structural unit represented by formula (BP-2), or a structural unit represented by formula (BP-3). 【Chemical 4】 [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). M BP1 、 M BP2 、 and, M BP3 may have substituents. When there are a plurality of such substituents, they may be the same or different, and may combine with each other to form a ring together with the atoms to which they are attached. L BP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R BP1 ), an oxygen atom or a sulfur atom, and these groups may have substituents. When a plurality of these 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 substituents. When a plurality of these 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. When a plurality of L BP1 are present, they may be the same or different from each other. n BP1 represents an integer of 0 or more and 10 or less. Ar BP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have substituents. When a plurality of these 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 each bonded.]
9. The composition according to claim 1, wherein the polymer compound (B) further contains at least one structural unit selected from the group consisting of a structural unit represented by formula (Y) and a structural unit represented by formula (X). [Chemical Formula 5] [In the formula, Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have substituents. When there are a plurality of these 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 respectively bonded.] 【Chemical Formula 6】 [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 substituents. When a plurality of these 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 each 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 substituents. When a plurality of these 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 each bonded. Ar X2 When a plurality of Ar are present, they may be the same or different from each other. Ar X4 When a plurality of Ar are present, they may be the same or different from each other. R X1 , R X2 and R X3 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 substituents. 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 respectively bonded. When a plurality of R X2 are present, they may be the same or different. When a plurality of R X3 are present, they may be the same or different. ]
10. The sum of the carbon atoms of all the constituent units constituting each of the above polymer compounds is C 3 and the (W sp3 × C 1 × 1000) / M sp3 value of each of the above polymer compounds is X 1 When the sum of the values of X sp3 is X sp2 / X sp3 is less than 0.55, the composition according to claim 1.
11. The composition according to any one of claims 1 to 10, further containing 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, an antioxidant, and a solvent.
12. A light emitting device containing the composition according to any one of claims 1 to 10.
Citation Information
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