Composition and light-emitting element using the same
A polymer compound composition with boron-containing heterocyclic skeletons reduces the driving voltage of light-emitting devices, improving efficiency and production ease.
Patent Information
- Application Number
- JP2023210440
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-12-13
- Publication Date
- 2025-06-25
AI Technical Summary
Existing light-emitting devices have high driving voltages, necessitating a composition that can reduce this to achieve more efficient operation.
A composition comprising two or more polymer compounds, at least one of which contains a boron atom and specific heterocyclic skeletons, with defined molecular weight ratios and side chain carbon content, is used to formulate a light-emitting device.
The composition results in a light-emitting device with a significantly lower driving voltage, enhancing efficiency and ease of production.
Smart Images

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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 reducing the driving voltage 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 a sufficiently low driving voltage.
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 calculated as such, the sum X of the values of (W1 × C sp2 × 1000) / M1 for each polymer compound sp2 is 17 or more, for example, 17 or more and 50 or less, 17.2 or more and 48 or less, preferably 17.5 or more and 45 or less, more preferably 17.5 or more and 35 or less, still more preferably 17.8 or more and 30 or less, and particularly preferably 18 or more and 27 or less, the 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's are present, they may be the same or different. R X3 When a plurality of R's 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 a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
[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 the 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 the 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 the 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] The above-mentioned Y1 and the above Y 2 and the above Y 3 is a group represented by an oxygen atom, a sulfur atom or -N(Ry)-, the composition according to [5].
[0019] [7] the above Y 1 the above Y 2 and the above Y 3 is a group represented by -N(Ry)-, the composition according to [6].
[0020] [8] The above 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 above low-molecular compound (B). M BP2 represents a group obtained by removing two hydrogen atoms from the above low-molecular compound (B). M BP3 represents a group obtained by removing three hydrogen atoms from the above low-molecular compound (B). M BP1 , M BP2 , and M BP3 may have a substituent. When a plurality of such substituents exist, 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 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. 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 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. L BP1 When there are a plurality of them, 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 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.]
[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 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.]
[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 respectively 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 respectively 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 respectively 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, for each of the above polymer compounds, (W1 × C sp3The sum of the values of (×1000) / M1 is X sp3 When X sp2 / X sp3 is 0.5 or more, for example, 0.50 or more and 100 or less, 0.52 or more and 50 or less, 0.53 or more and 20 or less, preferably 0.55 or more and 3 or less, more preferably 0.58 or more and 2.50 or less, still more preferably 0.60 or more and 2 or less, even more preferably 0.63 or more and 1.50 or less, particularly preferably 0.63 or more and 1.10 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 a sufficiently low driving voltage can be provided. Further, according to the present invention, a light-emitting device containing this composition can be provided.
Modes 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 "low molecular weight compound" has no molecular weight distribution and a molecular weight of 1×10 4 means the following compounds. The "high molecular weight compound" 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 ~1×10 8 ) and means a polymer. The "structural unit" means a unit that exists one or more times in the high molecular weight compound. The structural units contained two or more times in the high molecular weight compound are generally also called "repeating units". The high molecular weight compound may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms. If the end group of the high molecular weight compound remains as the polymerization active group as it is, when the high molecular weight compound is used in the production of a light emitting element, the light emitting characteristics and the like may deteriorate, so it is preferably a stable group. As the end group of the high molecular weight compound, preferably, it is a group conjugated with the main chain of the high molecular weight compound. For example, an aryl group or a monovalent heterocyclic group bonded to the main chain of the high molecular weight compound through 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, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, 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, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 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 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 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 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 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 a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.
[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 a monocyclic aromatic hydrocarbon (e.g., benzene), or a polycyclic aromatic hydrocarbon (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).) From these, a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring, and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent are included. The aromatic hydrocarbon group includes a group in which these groups are bonded in plurality. 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, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, a 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, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and 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 Rs 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 Rs 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 form a ring together with the atoms to which they are respectively bonded.]
[0054] The term "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 heterocyclic ring itself exhibits 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 the heterocyclic ring even though the heterocyclic ring itself does not exhibit 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, 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 formulas (B-1) to (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 they do not form a ring.
[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 polymer compounds, and among the two or more polymer compounds, at least one is a composition containing a polymer compound (B). All of the two or more polymer compounds contained in the composition of the present embodiment may be 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 types of polymer compounds contained in the composition of the present embodiment are, for example, two or more and 30 or less. Since the production of the composition of the present embodiment becomes easy and the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably two or more and 20 or less, more preferably two or more and 10 or less, still more preferably two or more and 5 or less, and particularly preferably two or three.
[0077] The composition of the present embodiment may contain only one kind of polymer compound (B), or may contain two or more kinds.
[0078] The types of 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 becomes easy and the driving voltage of the light-emitting element of the present embodiment becomes lower, 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 (hereinafter, also referred to as "heterocyclic group (b')") 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 boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, a sp 3 carbon atom and a nitrogen atom in the ring.
[0080] (Low-molecular compound (B)) The low-molecular compound (B) is a low-molecular compound having a condensed heterocyclic skeleton (b) containing 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, a selenium atom, a 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 weight 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 weight compound (B) is preferably a low molecular weight compound that does not contain a transition metal element (that is, a low molecular weight compound composed of only typical elements). The group obtained by removing one or more hydrogen atoms from the low molecular weight 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 weight compound (B) is preferably 1×10 2 ~5×10 3 and more preferably 2×10 2 ~3×10 3 and even more preferably 3×10 2 ~1.5×10 3 and particularly preferably 4×10 2 ~1×10 3 as follows.
[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 in the condensed heterocyclic skeleton (b), excluding the number of carbon atoms in the substituent, is usually 1 to 60, preferably 5 to 40, more preferably 10 to 30, and even more preferably 15 to 20. The number of heteroatoms in the condensed heterocyclic skeleton (b), excluding the number of heteroatoms in the substituent, is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, even more preferably 2 to 5, and particularly preferably 2 or 3. The number of boron atoms in the fused heterocyclic ring skeleton (b) is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1, excluding the number of boron atoms in the substituent. The total number of oxygen atoms, sulfur atoms, selenium atoms, sp 3 The total number of carbon atoms and nitrogen atoms in the fused heterocyclic ring skeleton (b) 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, excluding the number of atoms in the substituent.
[0083] Since the driving voltage of the light-emitting device of the present embodiment is lowered, the fused heterocyclic ring skeleton (b) 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 not forming a double bond in the ring.
[0084] Since the driving voltage of the light-emitting device of the present embodiment is further lowered, the fused heterocyclic ring skeleton (b) is preferably a 3- to 12-membered fused heterocyclic ring skeleton, more preferably a 3- to 6-membered fused heterocyclic ring skeleton, and still more preferably a 5-membered fused 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 preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, particularly preferably an alkyl group, a cycloalkyl group, an aryl group, or a substituted amino group, and 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 in the substituent 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, 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 which the substituent that the heterocyclic group (b') may 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 heterocyclic group or a substituted amino group, preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic 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 have no further substituent. Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which the substituent that the heterocyclic group (b') may have may further have are the same as the examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent that the heterocyclic group (b') may have, respectively.
[0090] The "nitrogen atom not forming a double bond" means a nitrogen atom bonded to three other atoms by single bonds respectively. The "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 group represented by the formula:
[0091]
Chemical formula
[0092] Since the synthesis of the polymer compound (B) is easy and the driving voltage of the light-emitting device of the present embodiment is lower, 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), 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 synthesis of the polymer compound (B) is easy and the driving voltage of the light-emitting element of the present embodiment becomes lower. 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 respectively. L BP1 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 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 respectively.
[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 Ar BP1 In 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 of the examples of the alkylene group in BP1 are the same. 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 and the preferred ranges of the examples of the arylene group in Y1 are included. Ar BP1 Examples of the heterocyclic group in BP1 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 and the preferred ranges of the examples of the divalent heterocyclic group in Y1 are included. L BP1 and Ar BP1 Examples and preferred examples of the substituents that L Y1 and Ar may have are the same as the examples and preferred ranges of the substituents that the group represented by Ar
[0097] The low molecular weight compound (B) is preferably a compound represented by formula (1-1), formula (1-2) or formula (1-3) because the driving voltage of the light emitting element of the present embodiment becomes lower, more preferably a compound represented by formula (1-2) or formula (1-3), and still more preferably a compound represented by formula (1-2).
[0098] Ar 1 Ar 2 and Ar 3Since the driving voltage of the light-emitting element of the present embodiment is lower, 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 1 , Ar, 2 and Ar 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 driving voltage of the light-emitting element of the present embodiment is lower, 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 driving voltage of the light-emitting element of this embodiment is lower, 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 most 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 most 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 driving voltage of the light emitting device of this embodiment is lower, Y 1 , Y 2 and Y 3 are preferably all oxygen atoms, sulfur atoms, or groups represented by -N(Ry)-, 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 the substituents that may be present are the same as the examples and preferred ranges of the substituents that may be present in the heterocyclic group (b').
[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 the examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituents that may be present in the heterocyclic group (b'), respectively. Examples and preferred ranges of the substituents that may be present in Ry are the same as the examples and preferred ranges of the substituents that may be present in the heterocyclic group (b').
[0105] Y 1 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 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)-represents a group, and these groups may have substituents. Y 1 and Ar 1 When they 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 those of the arylene group, divalent heterocyclic group, and alkylene group in 2 Y 3 and Y Y 1 and Ar 1 When they 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 those of the substituents that 2 Y 3 and Y Y 1 and Ar 1 When they 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 those 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 they are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group are the same as those of the divalent group when 1 Y 1 and Ar 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 they are bonded via a divalent group to form a ring, examples and preferred ranges of the divalent group are the same as those of the divalent group when 1 Y 1is the same as the example and preferred range of the divalent group in the case of forming a ring by bonding through a divalent group. Y 2 and Ar 3 may be directly bonded or bonded through a divalent group to form a ring, but since the synthesis of the polymer compound (B) is easy, it is preferably not to form a ring. Y 2 and Ar 3 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are Y 1 and Ar 1 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are the same as those in the case of Y Y 3 and Ar 2 may be directly bonded or bonded through a divalent group to form a ring, but since the synthesis of the polymer compound (B) is easy, it is preferably not to form a ring. Y 3 and Ar 2 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are Y 1 and Ar 1 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are the same as those of Y 3 and Ar 3 may be directly bonded or bonded through a divalent group to form a ring, but since the synthesis of the polymer compound (B) is easy, it is preferably not to form a ring. Y 3 and Ar 3 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are Y 1 and Ar 1 When and Ar are bonded through a divalent group to form a ring, the example and preferred range of the divalent group are the same.
[0106] The structural unit (B) is a structural unit having a group obtained by removing one to three hydrogen atoms from a compound represented by the above formula (1-1), formula (1-2) or formula (1-3), and is preferably a structural unit represented by formula (BP-1), formula (BP-2) or formula (BP-3). It is more preferably a structural unit having a group obtained by removing one or two hydrogen atoms from a compound represented by the above formula (1-2) or formula (1-3), and is a structural unit represented by the above formula (BP-1) or formula (BP-2). It is still more preferably a structural unit having a group obtained by removing two hydrogen atoms from a compound represented by formula (1-2), and is a structural unit represented by formula (BP-2).
[0107] Examples of the structural unit (B) include structural units represented by the following formulae.
[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. A plurality of R TS 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 are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the heterocyclic group (b') may have, respectively. R TSExamples of substituents that may be present and preferred ranges thereof are the same as those of substituents that may be further present in substituents that may be present in the heterocyclic group (b’).
[0112] The content of the structural unit (B) contained in the polymer compound (B) may be within 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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 in the polymer compound (B), or may be contained in two or more kinds. In addition, when two or more kinds of structural units (B) are contained in the polymer compound (B), the content represents the total content thereof.
[0113] (Other structural units) Since the driving voltage of the light-emitting element of the present embodiment becomes lower, the polymer compound (B) preferably further contains at least one structural unit selected from the group consisting of the structural unit represented by the following formula (Y) and the structural unit represented by the following 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 driving voltage of the light-emitting element of the present embodiment becomes lower, the polymer compound (B) preferably further contains the structural unit represented by the following formula (Y). 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 following formula (X). Since the driving voltage of the light-emitting element of the present embodiment becomes even lower, the polymer compound (B) preferably further contains the structural unit represented by the following formula (Y) and the structural unit represented by the following 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), 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 ones as the divalent groups in which at least one arylene group represented by the following 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 driving voltage of the light-emitting element of the present 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 may be bonded to each other to form a ring together with the carbon atoms to which they are 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 a 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] RY11 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 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 combination of two R Y2 s in the group represented by -C(R Y2 )2- is preferably both an alkyl group or a cycloalkyl group, both an aryl group, both a monovalent heterocyclic group, or one is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably both are alkyl groups or both are aryl groups, and these groups may have substituents. The two R Y2may 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] [ka]
[0136] [In the formula, R Y2 has the same meaning as above.]
[0137] The structural unit represented by the formula (Y-2) is preferably the structural unit represented by the formula (Y-2’).
[0138]
Chemical formula
[0139] [In the formula, R Y1 and X Y1 have the same meanings as described above.]
[0140]
Chemical formula
[0141] [In the formula, R Y1 and X Y1 have the same meanings as described above.]
[0142] The structural unit represented by the formula (Y-3) is preferably the structural unit represented by the formula (Y-3’).
[0143]
Chemical formula
[0144] [In the formula, R Y11 and X Y1 have the same meanings as described above.]
[0145]
Chemical formula
[0146]
Chemical formula
[0147] [In the formula, R Y1 has the same meaning as described above. R Y3represents 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] R Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, 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, R Y1 and R Y3 represent the same meaning as described above.
[0152]
Chemical formula
[0153] R Y4 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.
[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]
Chem.
[0156]
Chem.
[0157]
Chem.
[0158]
Chem.
[0159]
Chem.
[0160]
Chem.
[0161]
Chem.
[0162]
Chem.
[0163]
Chem.
[0164]
Chem.
[0165]
Chem.
[0166]
Chem.
[0167] When the polymer 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 polymer compound (B) are exhibited.
[0168] The polymer compound (B) contains a structural unit represented by the formula (Y), and Ar in the formula (Y) Y1 When is an arylene group, 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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 polymer compound (B) contains two or more structural units represented by the formula (Y), the content represents the total content.
[0169] The polymer compound (B) contains a structural unit represented by the formula (Y), and Ar in the formula (Y) Y1is 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 formula (Y) contained in the polymer compound (B) is, for example, 0.01 to 99.99 mol% relative to the total amount of structural units contained in the polymer compound (B). Since the driving voltage of the light-emitting device of this embodiment is lowered, the content is preferably 0.05 to 99 mol%, more preferably 0.1 to 90 mol%, even more preferably 0.5 to 70 mol%, particularly preferably 1 to 50 mol%, and particularly preferably 2 to 20 mol%. Note that when two or more structural units represented by formula (Y) are contained in the polymer compound (B), the content represents the total content thereof.
[0170] The polymer compound (B) may contain only one type of constitutional unit represented by formula (Y), or may contain two or more types.
[0171] A structural unit represented by the formula (X) a X1 is preferably 2 or less, more preferably 0 or 1, and even more preferably 0, since the driving voltage of the light-emitting element of this embodiment becomes lower.
[0172] a X2 is preferably 2 or less, more preferably 0 or 1, and even more preferably 0, since the driving voltage of the light-emitting element of this embodiment becomes lower.
[0173] R X1 , R X2 and R X3 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent.
[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 represented by and at least one divalent heterocyclic group 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 and the more preferred range of the arylene group and the divalent heterocyclic group represented by .
[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 Examples of the substituents which the groups represented by may have are preferably an alkyl group, a cycloalkyl group or an aryl group, 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 of 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 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 kinds of 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 in one kind, or may be contained in 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 in which 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 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) 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 driving voltage of the light-emitting element of the present embodiment becomes lower 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] (Exemplification of Polymer Compound (B), etc.) Examples of the polymer compound (B) include 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 indicate 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, and a graft copolymer, or may be in 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 below.
[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) preferably does not contain the structural 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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 functions as the composition of the present embodiment can be 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. Since the production of the composition of the present embodiment becomes easy and the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 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 functions as the polymer compound (A). Examples of the polymer compound (A) include the polymer compounds exemplified in the sections of the hole transport material, hole injection material, electron transport material, electron injection material, and light-emitting material described below, and polymer compounds 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). Since the driving voltage of the light-emitting element of the present embodiment becomes lower, 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 multiple types of polymer compounds may be used.
[0213] Since the driving voltage of the light-emitting element of the present embodiment becomes lower, 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 further contains the structural unit represented by the formula (X). Since the driving voltage of the light-emitting element of the present embodiment becomes lower and the hole-transporting property of the polymer compound (A) is excellent, the polymer compound (A) preferably further 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) can 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) can contain. Examples and preferred ranges of the structural units represented by the formula (X) and the formula (X) that the polymer compound (A) can 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) can contain.
[0214] When the polymer compound (A) contains a structural unit represented by the formula (X), the total content of the structural unit represented by the formula (X) may be within the range in which the function of the polymer compound (A) is 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 driving voltage of the light-emitting element of the present embodiment becomes lower 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 function of the polymer compound (A) is 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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) can be 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-transporting properties and the driving voltage of the light-emitting element of the present embodiment is lower, 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 most preferably 90 to 100 mol%.
[0217] Examples of the polymer compound (A) include polymer compounds AP-1 to AP-7. Here, "others" means a structural unit 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 types 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 even 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 even 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 a polymerization method such as a coupling reaction using a transition metal catalyst such as Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction, and Kumada reaction.
[0223] In the said polymerization method, examples of the method for 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 preferred, and the high molecular compound having a crosslinking group is more preferred.
[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 preferred.
[0229] When the composition of the present embodiment contains a hole transport material that is a low molecular 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 amount of solids 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) Electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may have a crosslinking group.
[0232] Examples of the low molecular 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 compound include polyphenylene, polyfluorene, and derivatives thereof. The high molecular 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 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 amount of solids contained in the composition of the present embodiment is 100 parts by mass.
[0235] In the composition of this 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; polymers containing an aromatic amine structure in the main chain or side chain.
[0239] When the composition of this 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 this embodiment is 100 parts by mass.
[0240] In the composition of this embodiment, the hole injection material and the electron injection material may 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 electric conductivity of the conductive polymer is preferably 1×10 -5 S / cm~1×10 3It is S / cm. In order to make the electrical 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, for example, polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include, for example, 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 the 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 the 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, for example, the metal complexes shown below.
[0249]
Chemical formula
[0250]
Chem.
[0251]
Chem.
[0252]
Chem.
[0253]
Chem.
[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 (hereinafter sometimes referred to as "ink") containing at least two or more kinds of polymer compounds including a polymer compound (B) and a solvent 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 amount 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 amount of the contents 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 driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 0.05 or more, more preferably 0.10 or more. Also, 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. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably less than 0.95, more preferably 0.94 or less, still more preferably 0.93 or less, particularly preferably 0.92 or less, especially preferably 0.91 or less, and especially more preferably 0.90 or less.
[0266] In one embodiment of the present invention, W1 may be, for example, not less than 0.001 and less than 1, not less than 0.01 and not more than 0.99, not less than 0.02 and not more than 0.98, not less than 0.03 and not more than 0.97, not less than 0.04 and not more than 0.96, not less than 0.04 and not more than 0.95. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably not less than 0.05 and less than 0.95, more preferably not less than 0.05 and not more than 0.94, still more preferably not less than 0.05 and not more than 0.93, particularly preferably not less than 0.10 and not more than 0.92, especially preferably not less than 0.10 and not more than 0.91, and even more preferably not less than 0.10 and not more than 0.90.
[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, not less than 0.01, not less than 0.02, not less than 0.03, not less than 0.04. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably not less than 0.05, more preferably not less than 0.10, still more preferably not less than 0.20, particularly preferably not less than 0.30, especially preferably not less than 0.40, and even more preferably not less than 0.50, still more preferably not less than 0.60, and particularly preferably not less than 0.70. 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, not more than 0.99, not more than 0.98, not more than 0.97, not more than 0.96, not more than 0.95. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably less than 0.95, more preferably not more than 0.94, still more preferably not more than 0.93, particularly preferably not more than 0.92, especially preferably not more than 0.91, and even more preferably not more than 0.90.
[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 0.03 or more and 0.97 or less, may be 0.04 or more and 0.96 or less, may be 0.04 or more and 0.95 or less. For example, since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably 0.05 or more and less than 0.95, more preferably 0.10 or more and 0.94 or less, still more preferably 0.20 or more and 0.94 or less, particularly preferably 0.30 or more and 0.93 or less, especially preferably 0.40 or more and 0.93 or less, especially more preferably 0.50 or more and 0.92 or less, especially still more preferably 0.60 or more and 0.91 or less, especially particularly preferably 0.70 or more and 0.90 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, 0.02 or more, 0.03 or more, 0.04 or more. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 0.05 or more, more preferably 0.10 or more, still more preferably 0.20 or more, particularly preferably 0.30 or more, especially preferably 0.40 or more, even more preferably 0.50 or more, still more preferably 0.60 or more, and particularly preferably 0.70 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, and for example, it may be less than 1, 0.99 or less, 0.98 or less, 0.97 or less, 0.96 or less, 0.95 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably less than 0.95, more preferably 0.94 or less, still more preferably 0.93 or less, particularly preferably 0.92 or less, especially preferably 0.91 or less, and even more preferably 0.90 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 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 and 1 or less, may be 0.01 or more and less than 1, may be 0.02 or more and 0.99 or less, may be 0.02 or more and 0.98 or less, may be 0.03 or more and 0.97 or less, may be 0.03 or more and 0.96 or less, may be 0.04 or more and 0.95 or less. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably 0.05 or more and less than 0.95, more preferably 0.10 or more and less than 0.95, still more preferably 0.20 or more and 0.94 or less, particularly preferably 0.30 or more and 0.94 or less, especially preferably 0.40 or more and 0.93 or less, especially more preferably 0.50 or more and 0.92 or less, especially still more preferably 0.60 or more and 0.91 or less, and especially particularly preferably 0.70 or more and 0.90 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 the polymer compounds contained in the composition is set to 1, for example, it may be 0, or may exceed 0. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably 0.01 or more, more preferably 0.02 or more, still more preferably 0.03 or more, particularly preferably 0.04 or more, especially preferably 0.05 or more, and especially more preferably 0.10 or more. Further, 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 driving voltage of the light-emitting element of this embodiment becomes lower, 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 0.60 or less, especially more preferably 0.50 or less, especially still more preferably 0.40 or less, and especially particularly preferably 0.30 or less.
[0272] In one embodiment of the present invention, the above-mentioned W1 A may be, for example, 0, 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 driving voltage of the light-emitting element of this embodiment becomes lower, 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 0.02 or more and 0.70 or less, especially preferably 0.03 or more and 0.60 or less, especially more preferably 0.04 or more and 0.50 or less, especially still more preferably 0.05 or more and 0.40 or less, and especially particularly preferably 0.10 or more and 0.30 or less.
[0273] In the composition of the present embodiment, when the total content of the polymer compound (A) is set to 1 based on the total amount of the contents of all the polymer compounds contained in the composition, it may be, for example, 0, or may exceed 0. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 0.01 or more, more preferably 0.02 or more, still more preferably 0.03 or more, particularly preferably 0.04 or more, especially preferably 0.05 or more, and especially more preferably 0.10 or more. Further, in the composition of the present embodiment, when the total content of the polymer compound (A) is set to 1 based on the total amount of the contents of all the polymer compounds contained in the composition, it may be, for example, 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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 0.60 or less, especially more preferably 0.50 or less, especially still more preferably 0.40 or less, and especially particularly preferably 0.30 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 taken as 1 with respect to the total content of all polymer compounds contained in the composition, for example, it may be 0, 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 driving voltage of the light-emitting element of this embodiment becomes lower, 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 0.02 or more and 0.70 or less, especially preferably 0.03 or more and 0.60 or less, especially more preferably 0.04 or more and 0.50 or less, especially still more preferably 0.05 or more and 0.40 or less, and especially particularly preferably 0.10 or more and 0.30 or less.
[0275] In the composition of this embodiment, the content of all polymer compounds contained in the composition of this embodiment may be, for example, 1 to 100% by mass with respect to the total solid content contained in the composition of this embodiment. Since the driving voltage of the light-emitting element of this embodiment becomes lower, 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 polymer compounds contained in the composition is defined as W1, the total molecular weight of all constituent units constituting each polymer compound is defined as M1, and the total number of carbon atoms of the side chains possessed by all constituent units constituting each polymer compound is defined as C. 2 When C sp2 is used, the sum X sp2 of the values of (W1 × C sp2 × 1000) / M1 for each polymer compound is 17 or more. In the present invention, X of the composition sp2 means the total average number of sp carbon atoms 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] Specific examples of the main chain and side chain of the polymer compound in the present invention will be described in detail by taking compounds PM5, PM6, PM7, and PM8 constituting the polymer compound P1, which will be described later, as examples.
[0278] Among the structural units contained in the polymer compound P1, in the structural unit corresponding to the compound PM5, the main chain of the polymer compound is a fluorenediyl group constituting the main chain, and the side chain is two hexylphenyl groups. Among the structural units contained 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 nitrogen atom constituting the main chain, and the side chain is a 4-(sec-butyl)phenyl group. Among the structural units contained 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 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 contained in the polymer compound P1, in the structural unit corresponding to the compound PM8, the main chain of the polymer compound is a fluorenediyl group constituting the main chain, and the side chain is two hexylphenyl groups.
[0279] As a result of studying the driving voltage of the light-emitting element, the present inventors have obtained the finding that the side chain in the polymer compound in the composition used for manufacturing the light-emitting element, particularly the influence of the number of sp carbon atoms possessed by the side chain, is great. The present inventors have found that the above-mentioned sp 2 2Regarding the number of carbon atoms, further investigation revealed that for every 1000 molecular weight of all the polymer compounds contained in the composition, the sum average of the number of sp 2 carbon atoms in the side chains of the composition, which is X sp2 , when it is 17 or more, surprisingly, it was found that the driving voltage of the light-emitting device manufactured using the composition can be reduced. Note that the X sp2 of the composition described in Patent Document 1, which had room for improvement in the driving voltage, was 15.5, and the X sp2 of the composition described in Patent Document 2 was 15.8 or 16.0.
[0280] When the X sp2 of the composition is 17 or more, the reason why the driving voltage of the light-emitting device manufactured from the composition can be reduced is not clear, but when the X sp2 is increased to 17 or more, the number of sp 2 carbon atoms in the side chains of the polymer compounds contained in the composition increases, which may smooth the movement of electrons in the light-emitting device, including the movement between each polymer chain contained in the composition, making it easier for current to flow through the light-emitting device and reducing the driving voltage of the light-emitting device.
[0281] The X sp2 of the composition of this embodiment can be obtained, 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 that structural unit to the total moles of all structural units excluding the end groups by the molecular weight of that structural unit is defined as M1. For each structural unit, the total number of sp 2 carbon atoms in the side chains is defined as C sp2 . Then, the X sp2 of the composition of this embodiment is the sum of (W1 × C sp2 × 1000) / M1 for each polymer compound.
[0282] The molecular weight of each structural unit constituting the polymer compound can be calculated, for example, using the value of Molecular Weight in ChemDraw (manufactured by Huylinks).
[0283] The sum of the sp carbon atoms in the side chains of all the constituent units that make up the polymer compound in the composition of this embodiment 2 The total number of carbon atoms (C sp2 ) means the sum of the sp carbon atoms contained in substituents other than the atoms, monocyclic rings and condensed rings that form the main chain of each polymer compound contained in the composition. 2
[0284] The specific calculation method of X of the composition of this embodiment sp2 will be described in detail by taking as an example the composition of the polymer compound P1 described below and the polymer compound P2 described below (polymer compound P1 / polymer compound P2 = 70% by mass / 30% 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 = 0.70 W1 P2 = 0.30 [In the formula, W1 P1 represents the ratio of the content of the polymer compound P1 in the composition (A), and W1 P2 represents the ratio of the content of the polymer compound P2 in the composition (A).]
[0286] The polymer compound P1 is a copolymer in which the constituent units derived from the compound PM5, the constituent units derived from the compound PM6, the constituent units derived from the compound PM7, and the constituent units derived from the compound PM8 are composed in a molar ratio of 44:5:1:50, based on the theoretical value obtained from the amount of the charged raw materials. The molecular weight of the constituent unit derived from the compound PM5 is 388.64, the molecular weight of the constituent unit derived from the compound PM6 is 299.42, the molecular weight of the constituent unit derived from the compound PM7 is 978.27, and the molecular weight of the constituent unit derived from the compound PM8 is 484.73. The number of sp carbon atoms in the side chain contained in the constituent unit derived from the compound PM5 is 0, and the number of sp carbon atoms in the side chain contained in the constituent unit derived from the compound PM6 is 6. The number of sp carbon atoms in the side chain contained in the constituent unit derived from the compound PM7 2 2 2 The number of carbon atoms is 12, and the sp of the side chain contained in the structural unit derived from compound PM8 2 The number of carbon atoms is 12. The structural units derived from compound PM5 and compound PM8 are both structural units represented by formula (Y), the structural unit derived from compound PM6 is a structural unit represented by formula (X), and the structural unit derived from compound PM7 is a structural unit represented by structural unit (B).
[0287] In terms of the theoretical value obtained from the amount of charged raw materials, the polymer compound P2 is a copolymer composed of a structural unit derived from compound PM10, a structural unit derived from compound PM9, and a structural unit derived from compound PM11 in 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 of the side chain contained in the structural unit derived from compound PM10 2 The number of carbon atoms is 36, and the sp of the side chain contained in the structural unit derived from compound PM9 2 The number of carbon atoms is 36, and the sp of the side chain contained in the structural unit derived from compound PM11 2 The number of carbon atoms is 60. The structural units derived from compound PM10, compound PM9, and compound PM11 are all structural units represented by formula (Y).
[0288] The sum of the molecular weights of all the structural units constituting the polymer compound is obtained as follows. M1 P1 =(388.64×0.44)+(299.42×0.05)+(978.27×0.01)+(484.73×0.50)=438.12 M1 P2 =(789.12×0.50)+(789.12×0.20)+(925.19×0.30)=829.94 [wherein, M1 P1is the sum of the molecular weights of all the constituent units that make up the polymer compound P1, M1 P2 represents the sum of the molecular weights of all the constituent units that make up the polymer compound P2.]
[0289] The total number of sp carbon atoms in the side chains of all the constituent units that make up the polymer compound 2 is determined as follows. C sp2,P1 =(0×0.44)+(6×0.05)+(12×0.01)+(12×0.50)=6.42 C sp2,P2 =(36×0.50)+(36×0.20)+(60×0.30)=43.2 [In the formula, C sp2,P1 is the total number of sp carbon atoms in the side chains of all the constituent units that make up the polymer compound P1, C 2 is the total number of sp carbon atoms in the side chains of all the constituent units that make up the polymer compound P2.] sp2,P2 represents the total number of sp carbon atoms in the side chains of all the constituent units that make up the polymer compound P2.] 2
[0290] The X of the composition (A) sp2 is determined as follows. X sp2 =(W1 P1 ×C sp2,P1 ×1000) / M1 P1 +(W1 P2 ×C sp2,P2 ×1000) / M1 P2 =(0.70×6.42×1000) / 438.12+(0.30×43.2×1000) / 829.94=25.9
[0291] <X of the composition sp3 > In the present invention, the X of the composition sp3 means the total average number of sp carbon atoms in the side chains per 1000 of the molecular weights of all the polymer compounds contained in the composition. 3 The X of the composition of this embodiment sp3 can be determined, 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 the constituent unit to the total moles of all constituent units excluding the end groups by the molecular weight of the constituent unit is defined as M1. For each constituent unit, the sp of the side chain determined 3 The total number of carbon atoms is C sp3 Then, X of the composition of this embodiment sp3 is the sum of (W1 × C sp3 × 1000) / M1 in each polymer compound.
[0292] The sp of the side chains possessed by all the constituent units constituting the polymer compound in the composition of this embodiment 3 The total number of carbon atoms (C sp3 ) means the total number of sp 3 carbon atoms contained in substituents other than the atoms, monocyclic rings, and condensed rings forming the main chain of each polymer compound contained in the composition.
[0293] X of the composition of this embodiment sp3 can be calculated in the same manner as the calculation method of X of the composition, except that "sp sp2 carbon atom number" is used instead of "sp 2 carbon atom number" used in the calculation of X of the composition. 3 That is, X of the composition can be calculated in the same way as the calculation method of X of the composition, except that "sp sp2 carbon atom number" is used. sp3 A specific calculation method will be described in detail by taking composition (A) as an example.
[0294] In polymer compound P1, the sp 3 carbon atom number of the side chain contained in the constituent unit derived from compound PM5 is 16, and the sp 3 carbon atom number of the side chain contained in the constituent unit derived from compound PM6 is 4. The sp 3 carbon atom number of the side chain contained in the constituent unit derived from compound PM7 is 28, and the sp 3 carbon atom number of the side chain contained in the constituent unit derived from compound PM8 is 12.
[0295] In polymer compound P2, the sp 3The number of carbon atoms is 12, and the sp of the side chain contained in the structural unit derived from compound PM9 3 The number of carbon atoms is 12, and the sp of the side chain contained in the structural unit derived from compound PM11 3 The number of carbon atoms is 0.
[0296] The sp of the side chain possessed by all the structural units constituting the polymer compound 3 The total sum of the number of carbon atoms is obtained as follows. C sp3,P1 =(16×0.44)+(4×0.05)+(28×0.01)+(12×0.50)=13.52 C sp3,P2 =(12×0.50)+(12×0.20)+(0×0.30)=8.4 [In the formula, C sp3,P1 represents the total sum of the number of carbon atoms of the sp of the side chain possessed by all the structural units constituting the polymer compound P1, and C 3 represents the total sum of the number of carbon atoms of the sp of the side chain possessed by all the structural units constituting the polymer compound P2.] sp3,P2 is the total number of carbon atoms of the sp of the side chain possessed by all the structural units that make up the polymer compound P2 3
[0297] X of the composition (A) sp3 is obtained as follows. X sp3 =(W1 P1 ×C sp3,P1 ×1000) / M1 P1 +(W1 P2 ×C sp3,P2 ×1000) / M1 P2 =(0.70×13.52×1000) / 438.12+(0.30×8.4×1000) / 829.94=24.6
[0298] C sp2 It 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, or 0 or more and 500 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower and the production of the polymer compound of the present 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, and especially more preferably 0 or more and 50 or less, and especially still more preferably 0 or more and 45 or less.
[0299] Since M1 makes the driving voltage of the light-emitting element of the present embodiment lower and the stability of the polymer compound of the present embodiment excellent, 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. Also, M1 may be, for example, 10000 or less, 8000 or less, 6000 or less, or 4000 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower and the production of the polymer compound of the present embodiment is easy, it is preferably 2000 or less, more preferably 1500 or less, and still more preferably 1000 or less.
[0300] 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 driving voltage of the light-emitting element of the present embodiment becomes lower, 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.
[0301] C sp3is, for example, greater than 0, may be 0.01 or more, may be 0.1 or more, may be 0.5 or more. Since the driving voltage of the light-emitting element of the present embodiment becomes lower 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. Also, C sp3 is, for example, may be 5000 or less, may be 2000 or less, may be 1000 or less, may be 500 or less, may be 200 or less, may be 150 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower 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, and especially particularly preferably 15 or less.
[0302] In one embodiment of the present invention, the C sp3 is, for example, may be greater than 0 and 5000 or less, may be 0.01 or more and 2000 or less, may be 0.1 or more and 1000 or less, may be 0.1 or more and 500 or less, may be 0.5 or more and 200 or less, may be 0.5 or more and 150 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, 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, and especially particularly preferably 8 or more and 15 or less.
[0303] <X of the composition sp2 / X sp3 > In the present invention, X of the composition sp2 / X sp3 is the sp of the side chains of all the polymer compounds contained in the composition 3The ratio of the sp carbon atoms in the side chains of all the polymer compounds contained in the composition to the number of carbon atoms. 2 means.
[0304] The X of the composition of this embodiment sp2 / X sp3 The specific calculation method of will be described in detail by taking the composition (A) as an example.
[0305] The X of the composition (A) sp2 / X sp3 is obtained as follows. X sp2 / X sp3 =25.9 / 24.6 = 1.05
[0306] In the composition of this embodiment, the X of the composition sp2 is, for example, 17 or more, may be higher than 17, may be 17.2 or more. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably 17.5 or more, more preferably 17.8 or more, and still more preferably 18 or more. Also, in the composition of the present invention, the X of the composition sp2 may be, for example, 50 or less, may be less than 50, may be 49 or less, may be 48 or less, may be 47 or less, may be 46 or less. Since the driving voltage of the light-emitting element of this embodiment becomes lower, it is preferably 45 or less, more preferably 42 or less, still more preferably 40 or less, particularly preferably 35 or less, especially preferably 30 or less, and especially more preferably 27 or less. When the X of the composition sp2 is above the above lower limit, the driving voltage of the light-emitting element of this embodiment tends to be low. Also, when the X of the composition sp2 is below the above upper limit, the driving voltage of the light-emitting element of this embodiment tends to be low.
[0307] In one embodiment of the present invention, in the composition of this embodiment, the X of the composition sp2It may be 17 or more and 50 or less, may be 17.2 or more and 48 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 17.5 or more and 45 or less, more preferably 17.5 or more and 35 or less, still more preferably 17.8 or more and 30 or less, and particularly preferably 18 or more and 27 or less.
[0308] In the composition of the present embodiment, X of the composition sp2 / X sp3 may be, for example, 0.50 or more, may be 0.52 or more, may be 0.53 or more, may be 0.54 or more. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 0.55 or more, more preferably 0.58 or more, still more preferably 0.60 or more, and particularly preferably 0.63 or more. Also, in the composition of the present invention, X of the composition sp2 / X sp3 may be, for example, 100 or less, may be 50 or less, may be 20 or less, may be 10 or less, may be 7 or less, may be 5 or less, may be 4 or less. Since the driving voltage of the light-emitting element of the present embodiment becomes lower, it is preferably 3 or less, more preferably 2.50 or less, still more preferably 2 or less, and particularly preferably 1.50 or less, and particularly preferably 1.10 or less. When X of the composition sp2 / X sp3 is above the above lower limit, the driving voltage of the light-emitting element of the present embodiment is likely to be low. Also, when X of the composition sp2 is below the above upper limit, the driving voltage of the light-emitting element of the present embodiment is likely to be low.
[0309] In one embodiment of the present invention, in the composition of the present embodiment, X of the composition sp2 / X sp3For example, it may be 0.50 or more and 100 or less, may be 0.52 or more and 50 or less, may be 0.53 or more and 20 or less. Since the driving voltage of the light-emitting element of the present embodiment is lower, it is preferably 0.55 or more and 3 or less, more preferably 0.58 or more and 2.50 or less, still more preferably 0.60 or more and 2 or less, even more preferably 0.63 or more and 1.50 or less, and particularly preferably 0.63 or more and 1.10 or less.
[0310] [Film] The composition of the present embodiment is suitably used for manufacturing a film. The film comprises the composition of the present embodiment.
[0311] The film is suitable as a light-emitting layer in a light-emitting element.
[0312] The film can be produced using ink, for example, by spin coating, casting, micro gravure 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.
[0313] The thickness of the film is usually 1 nm to 10 μm.
[0314] [Light-emitting element] The light-emitting element of the present embodiment is a light-emitting element containing the composition of the present embodiment. As the configuration of the light-emitting element of the present embodiment, for example, it has electrodes composed of an anode and a cathode, and a layer containing the composition of the present embodiment provided between the electrodes.
[0315] [Layer configuration] The layer containing the composition of the present embodiment is usually one or more layers of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and preferably a light-emitting layer. Each of these layers contains a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. Each of these layers can be formed by dissolving the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material in the above-described solvent to prepare an ink and using the same method as the above-described film production.
[0316] The light-emitting device 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 device of the present embodiment preferably has at least one layer of a hole-injecting layer and a hole-transporting layer between the anode and the light-emitting layer, and from the viewpoints of electron injection property and electron transport property, preferably has at least one layer of an electron-injecting layer and an electron-transporting layer between the cathode and the light-emitting layer.
[0317] Examples of the materials for the hole-transporting layer, the electron-transporting layer, the light-emitting layer, the hole-injecting layer, and the electron-injecting layer include the above-described hole-transporting material, electron-transporting material, light-emitting material, hole-injecting material, and electron-injecting material, respectively, in addition to the composition of the present embodiment.
[0318] When the materials for the hole-transporting layer, the electron-transporting layer, and the light-emitting layer are dissolved in the solvent used when forming the layers adjacent to the hole-transporting layer, the electron-transporting layer, and the light-emitting layer, respectively, in the production of the light-emitting device, it is preferable that the materials have a crosslinking group in order to avoid the materials being dissolved in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
[0319] In the light-emitting device of the present embodiment, as a method for forming each layer such as the light-emitting layer, the hole-transporting layer, the electron-transporting layer, the hole-injecting layer, and the electron-injecting layer, when 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.
[0320] The order, number, and thickness of the stacked layers are adjusted in consideration of the external quantum efficiency and luminance lifetime.
[0321] <Substrate / Electrode> The substrate in the light-emitting element may be any substrate on which an electrode can be formed and that does not chemically change when forming the organic layer. For example, it is 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.
[0322] Examples of the anode material include conductive metal oxides and translucent metals. Preferably, 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.
[0323] 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 alloy 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 stacked structure of two or more layers.
[0324] [Use] In order to obtain planar light emission using a light-emitting element, a planar anode and cathode may be arranged so as 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 so as to be orthogonal. By a method of separately applying 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
[0325] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.
[0326] 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.
[0327] <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.
[0328] 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).
[0329] 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.
[0330] <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. WO 2002 / 045184. Compound PM4 was synthesized according to the method described in JP-A-2008-106241. For compound PM5, a commercially available product was used. Compound PM6 was synthesized according to the method described in International Publication No. WO 2016 / 031639. Compound PM7 was synthesized according to the method described in International Publication No. WO 2019 / 004248. Compound PM8 was synthesized according to the method described in International Publication No. WO 2009 / 131255. Compounds PM9 and PM10 were synthesized according to the method described in International Publication No. WO 2022 / 181075.
[0331]
Chemical formula
[0332]
Chemical formula
[0333]
Chemical formula
[0334]
Chemical formula
[0335] <Synthesis Example 1> Synthesis of Compound PM11
Chemical formula
[0336] (Stage 1: Synthesis of Compound PM11B) After setting the inside of the reaction vessel to a nitrogen atmosphere, compound PM11A (19.2 g) and dichloromethane (285 mL) were added and cooled to 0°C. Sulfuric acid (8.7 g) was slowly added thereto, and the mixture was stirred at 0°C for 1 hour. A solution prepared by dissolving iodine monochloride (41.46 g) in dichloromethane (95 mL) was slowly added dropwise thereto, 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.
[0337] (Stage2: Synthesis of compound PM11C) After setting the inside of the reaction vessel to 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 and filtering, 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.
[0338] (Stage3: Synthesis of compound PM11D) After making the inside of the reaction vessel 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.
[0339] (Stage4: Synthesis of compound PM11) After making the inside of the reaction vessel 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 the resulting reaction solution was cooled 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.
[0340] <Synthesis Example 2> Synthesis of Polymer Compound IP1 The 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 the polymer compound IP1 was 7.6×10 4 and the Mw was 3.2×10 5 .
[0341] In terms of the theoretical value determined from the amount of 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 in a molar ratio of 50:30:12.5:7.5.
[0342] <Synthesis Example 3> Synthesis of Polymer Compound P1 The polymer compound P1 was synthesized by the method described in International Publication No. 2019 / 004248 using the compound PM5, the compound PM6, the compound PM7, and the compound PM8. The Mn of the polymer compound P1 is 7.7×10 4 and the Mw is 1.7×10 5 was.
[0343] In terms of the theoretical value determined from the amount of 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, a structural unit derived from the compound PM7, and a structural unit derived from the compound PM8 in a molar ratio of 44:5:1:50.
[0344] <Synthesis Example 4> Synthesis of Polymer Compound P2 After making the inside of the reaction vessel an inert gas atmosphere, compound PM10 (2.57 g), compound PM9 (1.18 g), compound PM11 (2.00 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.22 mg) and toluene (180 mL) were added and heated to 80°C. To the reaction solution, an aqueous 20 mass% tetraethylammonium hydroxide solution (83 mL) was added dropwise and refluxed for 3 hours. After the reaction, phenylboronic acid (0.10 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.15 mg) 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 mass% aqueous sodium N,N-diethyldithiocarbamate solution, twice with 10 mass% hydrochloric acid, twice with 3 mass% aqueous ammonia solution, 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. The precipitate was collected by filtration and dried to obtain a polymer compound P2 (1.18 g). The Mn of the polymer compound P2 was 4.1×10 4 and the Mw was 7.9×10 4 It was
[0345] The polymer compound P2 is a copolymer in which a structural unit derived from compound PM10, a structural unit derived from compound PM9, and a structural unit derived from compound PM11 are composed at a molar ratio of 50:20:30, based on the theoretical value determined from the amount of the charged raw materials.
[0346] <Example D1> (Formation of Anode and Hole Injection Layer) An anode was formed by forming an ITO film on a glass substrate to a thickness of 45 nm by sputtering. ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film on the anode to a thickness of 35 nm by spin coating, and heated on a hot plate at 240°C for 15 minutes in an air atmosphere. Thereby, a hole injection layer was formed.
[0347] (Formation of Hole Transport Layer) The polymer compound IP1 was dissolved in xylene at a concentration of 0.70% by mass. Using the obtained xylene solution, a film was formed with a thickness of 20 nm on the hole injection layer by spin coating, and in a nitrogen gas atmosphere, it was heated on a hot plate at 200 °C for 30 minutes to form a hole transport layer.
[0348] (Formation of Light Emitting Layer) The polymer compound P1 and the polymer compound P2 (polymer compound P1 / polymer compound P2 = 70% by mass / 30% by mass) were dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film was formed with a thickness of 60 nm on the hole transport layer by spin coating, and in a nitrogen gas atmosphere, it was heated at 170 °C for 10 minutes to form a light emitting layer.
[0349] (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.
[0350] (Evaluation of Light Emitting Device) By applying a voltage to the light emitting device D1, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. It was driven at a constant current density of 200 mA / cm 2 and the driving voltage was measured.
[0351] In Example D1, the X sp2 of the composition of the polymer compound P1 and the polymer compound P2 (polymer compound P1 / polymer compound P2 = 70% by mass / 30% by mass) is 25.9, and X sp2 / X sp3 is 1.05.
[0352] <Example D2> Fabrication and Evaluation of Light Emitting Device D2 In Example D1, a light-emitting device D2 was fabricated in the same manner as in Example D1, except that "polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 80% by mass / 20% by mass)" was used instead of "polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 70% by mass / 30% by mass)".
[0353] By applying a voltage to the light-emitting device D2, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. At a current density of 200 mA / cm 2 constant current driving was performed, and the driving voltage was measured.
[0354] In Example D2, X of the composition of polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 80% by mass / 20% by mass) sp2 was 22.1, and X sp2 / X sp3 was 0.83.
[0355] <Example D3> Fabrication and evaluation of the light-emitting device D3 In Example D1, a light-emitting device D3 was fabricated in the same manner as in Example D1, except that "polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 90% by mass / 10% by mass)" was used instead of "polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 70% by mass / 30% by mass)".
[0356] By applying a voltage to the light-emitting device D3, EL emission having a maximum peak wavelength of the emission spectrum at 450 nm was observed. At a current density of 200 mA / cm 2 constant current driving was performed, and the driving voltage was measured.
[0357] In Example D3, X of the composition of polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 90% by mass / 10% by mass) sp2 was 18.4, and X sp2 / X sp3 was 0.64.
[0358] <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 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 99% by mass / 1% by mass)” was used instead of “polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 70% by mass / 30% by mass)” in Example D1.
[0359] 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. At a current density of 200 mA / cm 2 constant current driving was performed, and the driving voltage was measured.
[0360] In Comparative Example CD1, X of the composition of polymer compound P1 and polymer compound P2 (polymer compound P1 / polymer compound P2 = 99% by mass / 1% by mass) sp2 is 15.0, and X sp2 / X sp3 is 0.49.
[0361] The results of Examples D1 to D3 and Comparative Example CD1 are shown in Table 3. In Table 3, the driving voltage difference [V] indicates the difference between the driving voltages of light-emitting elements D1 to D3 with respect to the driving voltage of light-emitting element CD1.
[0362]
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 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, and is a polymer compound containing a constitutional unit (B). 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 constitutional 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 constitutional units constituting each polymer compound. sp2 When 1 X is the sum of the values of (W sp2 × C 1 × 1000) / M for each polymer compound. sp2 The composition, wherein X is 17 or more.
2. wherein at least one of the two or more kinds of polymer compounds is a polymer compound (A), The composition according to claim 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). 【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 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.] 【Chemical Formula 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 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 each is 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 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 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. ]
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 Formula 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 is a group represented by an oxygen atom, a sulfur atom or -N(Ry)-, the composition according to claim 5.
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 Formula 4】 [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 weight 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 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 respectively 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 each 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 each bonded. When a plurality of L BP1 are present, they may be the same or different from each other. n BP1 represents an integer from 0 to 10 inclusive. Ar BP1 represents a hydrocarbon group or a 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.]
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 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.] [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 each is 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 respectively 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. 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 of each of the above polymer compounds is C 3 and is denoted as C sp3 For each of the above polymer compounds, when the value of (W 1 × C sp3 × 1000) / M 1 is summed up to X sp3 and when X sp2 / X sp3 is 0.5 or more, 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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