Color conversion material, ink using the same, color conversion film, light-emitting device, and display device

Abstract

To provide a color conversion material with superior luminance life.SOLUTION: A color conversion material for converting incident light into light of a wavelength longer than that of the incident light is provided, the color conversion material containing a compound (A) having a condensed aromatic hydrocarbon skeleton with six or more condensed rings.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a color conversion material, an ink, a color conversion film, a light-emitting device, and a display device using the same.

Background Art

[0002] As one of the techniques for multi-coloring light from a light source, there is a color conversion method. The color conversion method is a method of multi-coloring light by providing a color conversion film including a color conversion material that absorbs incident light and emits light having a wavelength distribution different from the absorption wavelength to a light source such as a light-emitting element. By combining such a color conversion film with a blue light source, red light, green light, and blue light can be obtained from the blue light source, and white light can also be obtained from these three primary color lights. Therefore, the color conversion material can be applied to liquid crystal display devices, electroluminescence (EL) display devices, lighting devices, and the like.

[0003] As the color conversion material, those containing inorganic phosphor fine particles made of quantum dots have been known. However, the color conversion material using quantum dots has problems in the process such as being vulnerable to heat, water, and oxygen, being difficult to handle, and having poor workability. Therefore, in recent years, a technique of using an organic material as the color conversion material has also been proposed.

[0004] For example, Patent Document 1 discloses a color conversion material composition including a fluorescent dye composed of a hetero polycyclic compound such as a phenylnaphthoxazole derivative and a benzofuran-1,2-naphthoquinone derivative, and a binder material. According to Patent Document 1, the color conversion film produced from this color conversion material composition does not deteriorate in color conversion performance even after long-term use, and there is no problem that the dye precipitates during storage and becomes unusable.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, the color conversion film produced using conventional organic color conversion materials has a problem that its luminance significantly decreases with long-term use, and its luminance life is not at a practical level even when applied to various devices such as light-emitting devices and display devices. An object of the present disclosure is to provide a color conversion material having excellent luminance life.

Means for Solving the Problems

[0007] The inventors of the present invention have conducted extensive studies to solve the above problems. As a result, they have found that in a color conversion material that converts incident light into light with a longer wavelength, the luminance life can be improved by using a compound (A) having a specific condensed aromatic hydrocarbon skeleton. That is, the gist of the present disclosure includes the following.

[0008] 〔1〕 A color conversion material that converts incident light into light with a longer wavelength than the incident light, the color conversion material including a compound (A) having a condensed aromatic hydrocarbon skeleton in which 6 or more rings are condensed. 〔2〕 The color conversion material according to 〔1〕, wherein the condensed aromatic hydrocarbon skeleton is a skeleton in which 6 to 8 rings are condensed. Color conversion material. 〔3〕 The color conversion material according to 〔1〕 or 〔2〕, wherein the condensed aromatic hydrocarbon skeleton is a skeleton in which only 6-membered rings are condensed. 〔4〕 The color conversion material according to any one of 〔1〕 to 〔3〕, wherein the condensed aromatic hydrocarbon skeleton has a structure represented by formula (1) or formula (2).

Chemical formula

[10] , comprising one or more compounds (B) selected from the group consisting of the following low molecular weight compound (B) and the following high molecular weight compound (B) and satisfying condition III. Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound satisfying the following condition I. High molecular weight compound (B): The high molecular weight compound (B) is a high molecular weight compound containing a structural unit (B) satisfying the following condition II. (Condition I) The energy level of the lowest singlet excited state of the low molecular weight compound (A)>the energy level of the lowest singlet excited state of the low molecular weight compound (B) (Condition II) The energy level of the lowest singlet excited state of the low molecular weight compound (A)>the energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (B) (Condition III) The molar content of the low molecular weight compound (A) per unit mass>[the molar content of the structural unit (B) per unit mass + the molar content of the low molecular weight compound (B) per unit mass] The structural unit (B) is a structural unit derived from an organoboron compound, The color conversion material according to

[11] , wherein the low molecular weight compound (B) is an organoboron compound.

[13] ​​​The color conversion material according to

[12] , wherein the organic boron compound is a low molecular weight compound represented by any one of formulas (7) to (9).

Chemical formula

[14] An ink containing the color conversion material according to any one of [1] to

[13] and a solvent.

[15] A color conversion film that converts incident light into light having a longer wavelength than the incident light, the color conversion film containing the color conversion material according to any one of [1] to

[13] .

[16] A light-emitting device containing the color conversion material according to any one of [1] to

[13] .

[17] A display device containing the color conversion material according to any one of [1] to

[13] . [Advantages of the Invention]

[0009] According to the present disclosure, a color conversion material excellent in luminance lifetime can be provided. [Modes for Carrying Out the Invention]

[0010] Hereinafter, embodiments of the present disclosure will be described in detail. The following description is an example (representative example) of the embodiments of the present disclosure, and the present disclosure is not limited to these contents as long as it does not exceed the gist thereof.

[0011] [Explanation of Common Terms] Terms commonly used in the present disclosure have the following meanings unless otherwise specified.

[0012] Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, Bu and n-Bu represent a normal butyl group, t-Bu represents a tert-butyl group, C6H 13 and nC6H 13 represents a normal hexyl group, C8H 17 and nC8H 17 represents a normal octyl group.

[0013] A hydrogen atom may be a deuterium atom or a light hydrogen atom.

[0014] In a formula representing a metal complex (including a boron complex), a solid line representing a bond with a central metal means a covalent bond or a coordination bond.

[0015] "High molecular compound" means a polymer having a molecular weight distribution and a number average molecular weight (Mn) in terms of polystyrene of 1×10 3 ~1×10 8 .

[0016] "Low molecular compound" means a compound having no molecular weight distribution and a molecular weight of 1×10 4 or less.

[0017] "Constituent unit" means a unit that exists in one or more in a high molecular compound. Two or more constituent units existing in a high molecular compound are generally also called "repeating units".

[0018] "Alkyl group" may be either straight-chain or branched and may have a substituent. The number of carbon atoms of a straight-chain alkyl group, excluding the number of carbon atoms of the substituent, is usually 1 to 50, preferably 2 to 30, more preferably 3 to 20, and still more preferably 4 to 8. The number of carbon atoms of a branched alkyl group, excluding the number of carbon atoms of the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.

[0019] Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group, tetradecyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, and fluorine atom (for example, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3-(4-methylphenyl)propyl group, 3-(3,5-di-hexylphenyl)propyl group, and 6-ethyloxyhexyl group), etc.

[0020] ​ The "cycloalkyl group" may have a substituent. The number of carbon atoms in the cycloalkyl group, excluding the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20.

[0021] Examples of the cycloalkyl group include a cyclopropyl group, a cyclohexyl group, a cyclohexylmethyl group, a cyclohexylethyl group, a norbornyl group, and an adamantyl group.

[0022] The "alkylene group" may have a substituent. The number of carbon atoms in the alkylene group, excluding the number of carbon atoms in the substituent, is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 5.

[0023] Examples of the alkylene group include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylmethylmethylene group, a phenylmethylene group, a diphenylmethylene group, a bis(trifluoromethyl)methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, and an octylene group.

[0024] The "cycloalkylene group" may have a substituent. The number of carbon atoms in the cycloalkylene group, excluding the number of carbon atoms in the substituent, is usually 3 to 20, preferably 6 to 10.

[0025] Examples of the cycloalkylene group include a 1,1-cyclopropylene group, a 1,2-cyclopropylene group, a 1,1-cyclobutylene group, a 1,1-cyclohexylene group, a 1,4-cyclohexylene group, a 3,3-dimethyl-5-methyl-1,1-cyclopropylene diyl group, and a 1,3-adamantane diyl group.

[0026] "Aryl hydrocarbon group" means a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from an aryl hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to the carbon atom constituting the ring from an aryl 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 aryl hydrocarbon is also referred to as an "arylene group".

[0027] The number of carbon atoms in the aryl hydrocarbon group, excluding the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, still more preferably 6 to 18.

[0028] Examples of the "aryl hydrocarbon group" include monocyclic aryl hydrocarbons (e.g., benzene), and polycyclic aryl hydrocarbons (e.g., bicyclic aryl hydrocarbons such as naphthalene and indene; tricyclic aryl hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, and fluorene; tetracyclic aryl hydrocarbons such as triphenylene, naphthacene, benzofluorene, pyrene, chrysene, and fluoranthene; pentacyclic aryl hydrocarbons such as dibenzofluorene, perylene, and benzofluoranthene; hexacyclic aryl hydrocarbons such as spirobifluorene; heptacyclic aryl hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene; and octacyclic aryl hydrocarbons such as dibenzospirobifluorene); and groups obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring therefrom. These groups may have substituents. The aryl hydrocarbon group includes groups in which a plurality of these groups are bonded.

[0029] "Aryl group" means the remaining atomic group obtained by removing one hydrogen atom directly bonded to the carbon atom constituting the ring from an aryl hydrocarbon. The aryl group may have a substituent. The number of carbon atoms in the aryl group, excluding the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, still more preferably 6 to 20, and particularly preferably 6 to 10.

[0030] Examples of the aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, benzophenanthryl group, benzoanthracenyl group, chrysenyl group, fluoranthenyl group, triphenylenyl group, benzofluoranthenyl group, dibenzoanthracenyl group, perylenyl group, helicenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as an alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, and fluorine atom.

[0031] The "arylene group" means a remaining atomic group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The arylene group may have a substituent. The number of carbon atoms in the arylene group, excluding the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18.

[0032] Examples of the arylene group include a phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrenediyl group, dihydrophenanthrenediyl group, naphthacenediyl group, fluorenediyl group, pyrenediyl group, perylenediyl group, chrysenediyl group, and groups in which these groups have a substituent, and preferably a group represented by any one of Formula (Ar-1) to Formula (Ar-20). The arylene group includes a group in which a plurality of these groups are bonded.

[0033]

Chemical formula

[0034]

Chemical formula

[0035] [Chemical formula]

[0036] [Chemical formula]

[0037] [In the formula, R and R a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. A plurality of R and R a may each be the same or different, and R 's may be bonded to each other to form a ring together with the atoms to which they are attached.] a

[0038] The "alkoxy group" may be either linear or branched and may have a substituent. The number of carbon atoms in the linear alkoxy group, excluding the carbon atoms of the substituent, is usually 1 to 40, preferably 1 to 20, more 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 20, more preferably 4 to 10.

[0039] 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 groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and a fluorine atom.

[0040] ​The "cycloalkoxy group" may have a substituent. 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.

[0041] Examples of the cycloalkoxy group include a cyclohexyloxy group.

[0042] The "aryloxy group" may have a substituent. 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, more preferably 6 to 40.

[0043] Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, a 1-pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and a fluorine atom.

[0044] The "arylthio group" may have a substituent. The number of carbon atoms in the arylthio group, excluding the carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 48, more preferably 6 to 40.

[0045] Examples of the arylthio group include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 1-anthracenylthio group, a 9-anthracenylthio group, a 1-pyrenylthio group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and a fluorine atom.

[0046] The "heterocyclic group of valence p" (where p represents an integer of 1 or more) means the remaining atomic group obtained by removing p hydrogen atoms out of the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from a heterocyclic compound. Among the heterocyclic groups of valence p, the "heterocyclic aromatic group of valence p", which is the remaining atomic group obtained by removing p hydrogen atoms out of the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from an aromatic heterocyclic compound, is preferred. The monovalent aromatic heterocyclic group is also referred to as a "heteroaryl group". The heterocyclic group of valence p may have a substituent.

[0047] The "aromatic heterocyclic compound" means compounds in which the heterocyclic ring itself, such as oxadiazole, thiadiazole, thiazole, ox azole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, and dibenzophosphole, exhibits aromaticity; and compounds in which, even though the heterocyclic ring itself, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, and benzopyran, does not exhibit aromaticity, an aromatic ring is fused to the heterocyclic ring.

[0048] The carbon number of the monovalent heterocyclic group, excluding the carbon number of the substituent, is usually 2 to 60, preferably 4 to 20.

[0049] Examples of the monovalent heterocyclic group include a thienyl group, a furyl group, a pyranyl group, a pyrrolyl group, a pyridyl group, a piperidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a naphthyridinyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzocarbazolyl group, a carbolinyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a dihydroindenocarbazolyl group, a benzoquinolinyl group, an acridinyl group, a dibenzoacridinyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, a phenanthrolinyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, and a cycloalkoxy group. The naphthyridinyl group is preferably any one of a 1,5-naphthyridinyl group, a 1,6-naphthyridinyl group, a 1,7-naphthyridinyl group, a 1,8-naphthyridinyl group, a 2,6-naphthyridinyl group, and a 2,7-naphthyridinyl group.

[0050] The number of carbon atoms of the divalent heterocyclic group, excluding the number of carbon atoms of the substituent, is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15.

[0051] Examples of the divalent heterocyclic group include divalent groups obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, and triazole. The divalent heterocyclic group includes groups in which a plurality of these groups are bonded.

[0052] "Alkenyl group" may be either linear or branched, and may have a substituent. 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.

[0053] "Cycloalkenyl group" may have a substituent. 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.

[0054] Examples of the alkenyl group and the cycloalkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl group, cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, and groups in which these groups have a substituent.

[0055] "Alkynyl group" may be either linear or branched, and may have a substituent. The number of carbon atoms in the 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.

[0056] "Cycloalkynyl group" may have a substituent. 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.

[0057] Examples of the alkynyl group and the cycloalkynyl 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 groups in which these groups have a substituent.

[0058] "Halogen atom" means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0059] The "amino group" may have a substituent and is preferably a substituted amino group. Preferred substituents of the amino group include an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. The number of carbon atoms of the substituted amino group is usually 1 to 30, preferably 2 to 18, more preferably 2 to 12.

[0060] Examples of the substituted amino group include dialkylamino groups such as dimethylamino group and diethylamino group; dicycloalkylamino groups such as dicyclohexylamino group; and diarylamino groups such as diphenylamino group, bis(4-methylphenyl)amino group, bis(4-tert-butylphenyl)amino group, and bis(3,5-di-tert-butylphenyl)amino group; and the like.

[0061] "Oxycarbonyl group" is a group represented by -COOR b where R b represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, preferably an alkyl group or an aryl group, more preferably an alkyl group. The number of carbon atoms of the oxycarbonyl group is usually 2 to 60, preferably 2 to 40, more preferably 2 to 20, still more preferably 2 to 10.

[0062] Examples of the oxycarbonyl group include alkyloxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, trifluoromethoxycarbonyl group, and pentafluoroethoxycarbonyl group; cyclohexyloxycarbonyl groups such as cyclohexyloxycarbonyl group; aryloxycarbonyl groups such as phenoxycarbonyl group and naphthoxycarbonyl group; and heteroaryloxycarbonyl groups such as pyridyloxycarbonyl group; and the like.

[0063] The "silyl group" may have a substituent and is preferably a substituted silyl group. Preferred substituents of the silyl group include an alkyl group, an alkenyl group, and an aryl group. Examples of the substituted silyl group include dialkylsilyl group, trialkylsilyl group, aryldialkylsilyl group, alkyldiarylsilyl group, and triarylsilyl group. The number of carbon atoms of the substituted silyl group is preferably 1 to 30.

[0064] Examples of the silyl group include trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, propyldimethylsilyl group, vinyldimethylsilyl group, phenyldimethylsilyl group, tert-butyldiphenylsilyl group, triphenylsilyl group, and trinaphthylsilyl group and the like.

[0065] The "siloxanyl group" refers to, for example, a silicon compound group via an ether bond such as a trimethylsiloxanyl group.

[0066] The "borryl group" may have a substituent and is preferably a substituted boryl group. Examples of the substituent of the boryl group include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryloxy group, an alkoxy group, and a hydroxyl group, etc., and preferably an aryl group or an aryloxy group.

[0067] The "sulfonic acid group" may have a substituent and is preferably a substituted sulfonic acid group. Examples of the substituent of the sulfonic acid group include a halogen atom, an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, and an alkoxy group, etc., and preferably an alkyl group or an aryl group. The substituted sulfonic acid group when the substituent is an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkoxy group, etc. is also referred to as a "sulfonic acid ester group". The carbon number of the substituted sulfonic acid group is usually 0 to 30, preferably 1 to 18, more preferably 2 to 12.

[0068] The "amide group" may have a substituent and is preferably a substituted amide group. As the substituent of the amide group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred. The carbon number of the substituted amide group is usually 1 to 30, preferably 2 to 18, more preferably 2 to 12.

[0069] The "sulfonamide group" may have a substituent and is preferably a substituted sulfonamide group. As the substituent of the sulfonamide group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferred. The carbon number of the substituted sulfonamide group is usually 1 to 30, preferably 2 to 18, more preferably 2 to 12.

[0070] The "acyl group" may have a substituent and is preferably a substituted acyl group. As the substituent of the substituted acyl group, an alkyl group, an aryl group or a monovalent heterocyclic group is preferred. The carbon number of the substituted acyl group is usually 1 to 30, preferably 2 to 18, more preferably 2 to 12.

[0071] The "sulfonyl group" is -SO2R b and represents a group. R b has the same meaning as described above, and the preferred range is also the same. The number of carbon atoms in the sulfonyl group is usually 1 to 20, preferably 1 to 12, more preferably 2 to 8.

[0072] The "substituent" refers to 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, a cycloalkynyl group, a hydroxyl group, a thiol group, an alkylthio group, an aryloxy group, an arylthio group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a sulfonic acid group, or a phosphine oxide group, preferably 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, or a cycloalkynyl group, more preferably a halogen atom, an aryl group, or a heteroaryl group. These substituents may further have substituents.

[0073] The descriptions of "X or more and Y or less" and "X to Y" representing numerical ranges mean a numerical range including the lower limit X and the upper limit Y which are the endpoints. When the lower limit value and the upper limit value of the numerical range are separately described, the numerical range can be a combination of any lower limit value and any upper limit value.

[0074] [1. Color conversion material] The color conversion material according to the first embodiment of the present disclosure includes a compound (A) having a condensed aromatic hydrocarbon skeleton in which 6 or more rings are condensed. The color conversion material of this embodiment is a color conversion material that converts incident light into light having a longer wavelength than the incident light, for example, a material that converts blue light from a light source into green light or red light.

[0075] Since the color conversion material of this embodiment is excellent in luminance lifetime, it can be suitably used as a color conversion material for light-emitting devices and display devices.

[0076] In a preferred embodiment, the color conversion material of this embodiment exhibits sufficient color conversion efficiency. Specifically, the color conversion efficiency of the color conversion material of this embodiment determined by the following method is preferably 20 to 100%, more preferably 40 to 100%, still more preferably 50 to 100%, particularly preferably more than 50% and 100% or less, most preferably 60 to 95%, and even more preferably 70 to 90% at an excitation wavelength of 460 nm.

[0077] The color conversion efficiency of the color conversion material is evaluated using a film-like measurement sample having a certain thickness as shown below.

[0078] The measurement sample is prepared by forming a color conversion layer on a synthetic quartz glass substrate by applying a solution containing the color conversion material to the synthetic quartz glass substrate by spin coating and drying. The solution used for spin coating is prepared by dissolving the color conversion material in an organic solvent such as xylene or toluene at a concentration of 1 to 3% by mass. Spin coating is performed at a rotational speed of 1000 to 4000 rpm so that the thickness of the resulting film after drying is 100 nm.

[0079] For the evaluation of the color conversion efficiency, an evaluation apparatus (for example, the absolute PL quantum yield measurement apparatus C9920-02 manufactured by Hamamatsu Photonics) is used. The light emitted from the xenon lamp of the excitation light source is spectroscopically analyzed by the evaluation apparatus, and the measurement sample installed in the integrating sphere is caused to emit light. The light collected by the integrating sphere is wavelength-dispersed and photometrically measured by a multichannel spectroscope to obtain an emission spectrum. For the calculation of the color conversion efficiency, first, the reference excitation light is measured using a synthetic quartz glass substrate on which no color conversion layer is formed, and from the sample (measurement sample) on which the color conversion layer is formed, the sample emission and the sample excitation light remaining without being absorbed are measured. Next, based on the measurement results, the number of photons of each light is determined, and the color conversion material is calculated by the following formula (i).

[0080]

Number

[0081] η: Color conversion efficiency m: Number of photons of excitation light irradiated on the sample m’: Number of photons of excitation light remaining without being absorbed n: Number of photons emitted from the sample as light

[0082] The total content of compound (A) in the color conversion material of this embodiment is preferably 50% by mass or more, more preferably 70% by mass or more, and usually 100% or less. Since the polymer compound (AB) described later is also compound (A), when the color conversion material of this embodiment contains the polymer compound (AB) described later, the content of the polymer compound (AB) is treated as the content of compound (A).

[0083] 〔1-1. Compound (A)〕 The color conversion material of this embodiment may contain compound (A) alone or in combination of two or more. Compound (A) is a compound having at least one condensed aromatic hydrocarbon skeleton in which 6 or more rings are condensed per molecule.

[0084] The condensed aromatic hydrocarbon skeleton is a skeleton composed of only carbon atoms and hydrogen atoms and does not contain heteroatoms such as boron atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0085] The condensed aromatic hydrocarbon skeleton preferably has a skeleton in which 6 to 14 rings are condensed, more preferably a skeleton in which 6 to 10 rings are condensed, and even more preferably a skeleton in which 6 to 8 rings are condensed.

[0086] The ring constituting the condensed aromatic hydrocarbon skeleton is preferably a 5- to 8-membered ring, more preferably a 5-membered ring or a 7-membered ring, and still more preferably a 6-membered ring, from the viewpoints of the luminance lifetime and ease of synthesis of the color conversion material of the present embodiment. It is particularly preferable that the condensed aromatic hydrocarbon skeleton is a skeleton condensed with only 6-membered rings.

[0087] Compound (A) may be a compound consisting only of a condensed aromatic hydrocarbon skeleton, a compound in which a hydrogen atom directly bonded to a carbon atom constituting a condensed ring of the condensed aromatic hydrocarbon skeleton is substituted with a substituent, or a polymer compound containing a structural unit derived from these compounds. The substituent that may be introduced into the condensed aromatic hydrocarbon skeleton may contain a heteroatom, but preferably does not contain a heteroatom.

[0088] As the substituent that may be introduced into the condensed aromatic hydrocarbon skeleton, since the color conversion material of the present embodiment has an excellent luminance lifetime, it is preferably an alkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and more preferably an alkyl group or an aryl group.

[0089] Preferred condensed aromatic hydrocarbon skeletons include those having a structure represented by formula (1) or formula (2) and condensed with two or more rings in this structure. The condensation position of the structure represented by formula (1) or formula (2) and the aforementioned two or more rings is not particularly limited.

[0090] From the viewpoints of the luminance lifetime and ease of synthesis of the color conversion material of the present embodiment, the number of rings condensed with the structure represented by formula (1) or formula (2) is preferably 2 to 10, more preferably 2 to 6, and still more preferably 2 to 4.

[0091] As the condensed aromatic hydrocarbon skeleton having a structure represented by formula (1) or formula (2), a condensed aromatic hydrocarbon skeleton represented by any of formula (3’) to formula (6’) is preferable.

[0092]

Chemical formula

[0093] Compound (A) may be a low-molecular compound having the condensed aromatic hydrocarbon skeleton described above (hereinafter also referred to as "low-molecular compound (A)"), or may be a high-molecular compound having the condensed aromatic hydrocarbon skeleton described above (hereinafter also referred to as "high-molecular compound (A)").

[0094] [1-1-1. Low-molecular compound (A)] The low-molecular compound (A) is preferably a compound having a structure represented by formula (1) or formula (2), and more preferably a condensed aromatic hydrocarbon represented by any of formulas (3) to (6). Each of the condensed aromatic hydrocarbons represented by any of formulas (3) to (6) is a compound having a condensed aromatic hydrocarbon skeleton represented by any of formulas (3') to (6'). The substituents that the condensed aromatic hydrocarbon represented by any of formulas (3) to (6) may have are synonymous with the substituents that may be introduced into the condensed aromatic hydrocarbon skeleton described above, and the preferred embodiments are also the same.

[0095] Examples of the low-molecular compound (A) include compounds represented by the following formulas and compounds further having substituents bonded thereto.

[0096] [Chemical formula]

[0097] [Chemical formula]

[0098] [Chemical formula]

[0099] [Chemical formula]

[0100] [Chemical]

[0101] [1-1-2. Method for Producing Low-Molecular Compound (A)] The low-molecular compound (A) can be produced by any method that combines known organic synthesis reactions or reactions analogous thereto. Examples of such methods include those described in Macromolecules, Vol. 39, No. 17, pp. 5696-5704 (2006), Journal of Physical Chemistry A (J. Phys. Chem. A), Vol. 109, pp. 5696-5704 (2005), etc., or methods analogous thereto.

[0102] [1-1-3. High-Molecular Compound (A)] The high-molecular compound (A) contains one or more structural units (A) having the condensed aromatic hydrocarbon skeleton described above. The high-molecular compound (A) may contain the structural unit (A) in any of the main chain, side chain, and terminal, but since the luminance lifetime of the color conversion material of the present embodiment is excellent, it is preferable that the structural unit (A) is contained in the main chain as a repeating unit.

[0103] The high-molecular compound (A) may contain one or more other structural units other than the structural unit (A). The other structural units may be any structural units that do not have the condensed aromatic hydrocarbon skeleton described above, but the structural unit (Y), the structural unit (Z), and the structural unit (B) described later are preferable. Note that the structural unit (A), the structural unit (Y), the structural unit (Z), and the structural unit (B) are different from each other.

[0104] (Structural Unit (A)) The constitutional unit (A) is a constitutional unit having the condensed aromatic hydrocarbon skeleton described above. The constitutional unit (A) is preferably a constitutional unit obtained by removing x or more hydrogen atoms from the low-molecular compound (A), more preferably a constitutional unit obtained by removing x or more hydrogen atoms from a compound having a structure represented by the formula (1) or the formula (2), and even more preferably a constitutional unit obtained by removing x or more hydrogen atoms from a condensed aromatic hydrocarbon represented by any one of the formulas (3) to (6). Here, x is an integer of 1 or more, and from the viewpoint of the ease of synthesis of the polymer compound (A), it is preferably 1 to 3, more preferably 1 or 2, and even more preferably 2. The low-molecular compound (A) from which the constitutional unit of the polymer compound (A) is derived has the same meaning as the low-molecular compound (A) described in the above [1-1-1. Low-molecular compound (A)], and the preferred embodiments thereof are also the same.

[0105] The hydrogen atom removed from the low-molecular compound (A) may be a hydrogen atom directly bonded to the condensed aromatic hydrocarbon skeleton, or may be a hydrogen atom possessed by a substituent introduced into the condensed aromatic hydrocarbon skeleton, but is preferably a hydrogen atom directly bonded to the condensed aromatic hydrocarbon skeleton.

[0106] When the low-molecular compound (A) is a condensed aromatic hydrocarbon represented by the formula (3), the constitutional unit obtained by removing x hydrogen atoms from the low-molecular compound (A) is preferably a constitutional unit obtained by removing x hydrogen atoms from a position selected from the group consisting of the 2nd, 4th, 6th, 8th, 10th, 12th positions of the condensed aromatic hydrocarbon represented by the formula (3) and the substituents directly bonded to these positions, and more preferably a constitutional unit obtained by removing x hydrogen atoms from a position selected from the group consisting of the 6th and 12th positions.

[0107] When the low-molecular compound (A) is a condensed aromatic hydrocarbon represented by the formula (4), the structural unit formed by removing x hydrogen atoms from the low-molecular compound (A) is preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 2-position, 6-position, 10-position, 14-position of the condensed aromatic hydrocarbon represented by the formula (4), and substituents directly bonded to these positions, and more preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 2-position and 10-position.

[0108] When the low-molecular compound (A) is a condensed aromatic hydrocarbon represented by the formula (5), the structural unit formed by removing x hydrogen atoms from the low-molecular compound (A) is preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 5-position, 6-position, 11-position, and 12-position of the condensed aromatic hydrocarbon represented by the formula (5), and substituents directly bonded to these positions, and more preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 5-position and 12-position.

[0109] When the low-molecular compound (A) is a condensed aromatic hydrocarbon represented by the formula (6), the structural unit formed by removing x hydrogen atoms from the low-molecular compound (A) is preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 7-position and 16-position of the condensed aromatic hydrocarbon represented by the formula (6), and more preferably a structural unit formed by removing x hydrogen atoms from positions selected from the group consisting of the 7-position and 16-position.

[0110] Examples of the structural unit (A) include structural units represented by the formulas (AM-1) to (AM-71), and structural units further having substituents bonded thereto.

[0111]

Chemical formula

[0112]

Chemical formula

[0113]

Chem.

[0114]

Chem.

[0115]

Chem.

[0116] The total content of the constituent unit (A) in the polymer compound (A) is preferably 25 to 100 mol%, more preferably 30 to 99.99 mol%, still more preferably 40 to 90 mol%, particularly preferably 45 to 80 mol%, and most preferably 47 to 70 mol% with respect to the total amount of all the constituent units contained in the polymer compound (A), because the stability of the polymer compound (A) is excellent.

[0117] (Constituent unit (Y)) The polymer compound (A) may contain a constituent unit (Y) represented by the following formula as another constituent unit other than the constituent unit (A). When the polymer compound (A) contains the constituent unit (Y), the constituent unit (Y) may be contained in either the main chain or the side chain of the polymer compound (A). It is preferable that the constituent unit (Y) is contained in the main chain as a repeating unit, and it is more preferable that the constituent unit (Y) is contained in the main chain as a repeating unit together with the constituent unit (A). Note that the constituent unit (Y) is a constituent unit that does not satisfy the conditions (II) and (III) described later.

[0118]

Chem.

[0119] [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. These groups may have substituents.

[0120] Ar Y1 The arylene group represented by Y1 may be any group that does not have the condensed aromatic hydrocarbon skeleton described above, but is preferably a group represented by any of formula (Ar-1), formula (Ar-2), formula (Ar-4) to formula (Ar-7), formula (Ar-9) to formula (Ar-11), formula (Ar-13), formula (Ar-15) to formula (Ar-17), and formula (Ar-19), more preferably a group represented by any of formula (Ar-1), formula (Ar-4), formula (Ar-5), formula (Ar-7), formula (Ar-9) to formula (Ar-11), and formula (Ar-19), and even more preferably a group represented by any of formula (Ar-1), formula (Ar-9), and formula (Ar-10). These groups may have substituents.

[0121] Ar Y1 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, represented by Y1 , the preferred ranges of the arylene group and the divalent heterocyclic group are the same as the preferred ranges of the arylene group represented by Ar Y1 and the preferred range of the divalent heterocyclic group represented by Ar Y1 respectively.

[0122] Ar Y1 The substituents that the group represented by Y1 may have are preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or an aryl group, and even more preferably an alkyl group. These groups may further have substituents.

[0123] Examples of the structural unit (Y) include a structural unit represented by formula (Y-1) or formula (Y-2). From the viewpoint of the luminance lifetime of the color conversion material of the present embodiment, a structural unit represented by formula (Y-2) is preferred.

[0124] [Chemistry]

[0125] [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. These groups may have substituents. When there are a plurality of R Y1 , they may be the same or different, and adjacent R Y1 s may be bonded to each other to form a ring together with the carbon atoms to which they are attached.]

[0126] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. These groups may have substituents.

[0127] [Chemistry]

[0128] [In the formula, R Y1 represents the same meaning as described above. X Y1 represents 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. 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 attached.]

[0129] R Y2is 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 further preferably an alkyl group or an aryl group. These groups may have a substituent.

[0130] X Y1 In the above, -C(R Y2 )2-, where R Y2 The combination of is preferably such that both are alkyl groups or cycloalkyl groups; both are aryl groups; both are monovalent heterocyclic groups; or one is an alkyl group or cycloalkyl group and the other is an aryl group or monovalent heterocyclic group; more preferably, both are aryl groups; or one is an alkyl group or cycloalkyl group and the other is an aryl group; and even more preferably, both are aryl groups. These groups may have a substituent. When two R Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 The group represented by 2- is preferably a group represented by any one of formulae (Y-A1) to (Y-A5), and more preferably a group represented by formula (Y-A4). These groups may have a substituent.

[0131] [ka]

[0132] X Y1 In the above, -C(R Y2 )=C(R Y2 Two R in the group represented by Y2 The combination is preferably such that both are alkyl or cycloalkyl groups; or one is an alkyl group. and the other is an aryl group or a cycloalkyl group. These groups may have a substituent.

[0133] As the structural unit (Y), for example, a structural unit composed of an arylene group represented by Formula (Y-101) to Formula (Y-139) is preferable.

[0134]

Chem.

[0135]

Chem.

[0136]

Chem.

[0137]

Chem.

[0138]

Chem.

[0139]

Chem.

[0140]

Chem.

[0141]

Chem.

[0142]

Chem.

[0143] When the polymer compound (A) contains the structural unit (Y), the total content of the structural unit (Y) in the polymer compound (A) is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol%, particularly preferably 20 to 55 mol%, and most preferably 30 to 53 mol% with respect to the total amount of all the structural units contained in the polymer compound (A), because the stability of the polymer compound (A) is excellent.

[0144] (Structural unit (Z)) The polymer compound (A) may contain, as other structural units than the structural unit (A), a structural unit (Z) represented by the following formula. When the polymer compound (A) contains the structural unit (Z), the structural unit (Z) may be contained in either the main chain or the side chain of the polymer compound (A), but it is preferably contained in the main chain as a repeating unit, and more preferably contained in the main chain as a repeating unit together with the structural unit (A). Note that the structural unit (Z) is a structural unit that does not satisfy the conditions (II) and (III) described later.

[0145] [Chemical formula]

[0146] [In the formula, Ar Y1 represents the same meaning as described above. Alk Z1 represents an alkylene group or a cycloalkylene group. These groups may have substituents.]

[0147] Examples of the structural unit (Z) include a structural unit represented by the formula (Z-1) or the formula (Z-2). From the viewpoint of the luminance lifetime of the color conversion material of the present embodiment, the structural unit represented by the formula (Z-1) is preferable.

[0148] [Chemical formula]

[0149] [In the formula, R Y1 represents the same meaning as described above. R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group. These groups may have substituents.]

[0150] R XX is preferably a hydrogen atom or an alkyl group.

[0151] As the structural unit (Z), for example, the structural units represented by formula (Y-401) to formula (Y-415) are preferable.

[0152]

Chemical formula

[0153]

Chemical formula

[0154]

Chemical formula

[0155]

Chemical formula

[0156] When the polymer compound (A) contains the structural unit (Z), the total content of the structural unit (Z) in the polymer compound (A) is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol%, particularly preferably 20 to 55 mol%, and most preferably 30 to 53 mol% with respect to the total amount of all the structural units contained in the polymer compound (A), because the stability of the polymer compound (A) is excellent.

[0157] 〔1-2. Compound (B)〕 The color conversion material of this embodiment preferably contains compound (B) and satisfies the following condition III. When compound (A) is a low-molecular compound (A), compound (B) is one or more compounds selected from the group consisting of the following low-molecular compound (B) and the following high-molecular compound (B). When compound (A) is a high-molecular compound (A), compound (B) is one or more compounds selected from the group consisting of the following low-molecular compound (B), the following high-molecular compound (AB), and the following high-molecular compound (B).

[0158] Low-molecular compound (B): The low-molecular compound (B) is a low-molecular compound that satisfies the following condition I. High-molecular compound (AB): The high-molecular compound (AB) is a high-molecular compound containing the above-mentioned structural unit (A) and a structural unit (B) that satisfies the following condition II, and also corresponds to the high-molecular compound (A). High-molecular compound (B): The high-molecular compound (B) is a high-molecular compound containing a structural unit (B) that satisfies the following condition II (however, excluding those corresponding to the above-mentioned high-molecular compound (A)).

[0159] (Condition I) When compound (A) is a low-molecular compound (A): The energy level of the lowest singlet excited state of the low-molecular compound (A)>The energy level of the lowest singlet excited state of the low-molecular compound (B) When compound (A) is a high-molecular compound (A): The energy of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (A) Level>The energy level of the lowest singlet excited state of the low-molecular compound (B)

[0160] (Condition II) The energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (A)>The energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (B)

[0161] (Condition III) When compound (A) is a low-molecular compound (A): The molar content of the low-molecular compound (A) per unit mass > [the molar content of the structural unit (B) per unit mass + the molar content of the low-molecular compound (B) per unit mass]. When the compound (A) is a high-molecular compound (A): The molar content of the structural unit (A) per unit mass > [the molar content of the structural unit (B) per unit mass + the molar content of the low-molecular compound (B) per unit mass]

[0162] The compound (B) is a compound that can function as a light-emitting dye. The compound (B) is preferably a compound that emits green light (wavelength 500 - 570 nm) or red light (wavelength 620 - 780 nm).

[0163] The compound (B) may be used alone, or two or more kinds may be used in combination at any combination and ratio. Since the color conversion efficiency of the color conversion material is further improved by cascade energy transfer, it is preferable to contain 1 to 4 kinds of the compound (B), and more preferably to contain 1 to 2 kinds of the compound (B).

[0164] A preferred embodiment of the color conversion material containing the compound (B) includes the high-molecular compound (A) and one or more compounds (B) selected from the group consisting of the low-molecular compound (B), the high-molecular compound (AB), and the high-molecular compound (B), satisfies condition III, and the compound (B) contains two or more compounds and / or structural units selected from the group consisting of the low-molecular compound (B) and the structural unit (B).

[0165] The energy levels of the lowest singlet excited states of various compounds are determined by the following method. First, the ground state of the compound is structurally optimized by the density functional method at the B3LYP level. At this time, 6-31G(d) is used as the basis function. Then, using the obtained structurally optimized structure, the energy levels of the lowest singlet excited states of the compound are calculated by the time-dependent density functional method at the B3LYP level. However, when an atom for which 6-31G(d) cannot be used is included, LANL2DZ is used for that atom. Note that Gaussian16 is used as the quantum chemistry calculation program for the calculation.

[0166] When the color conversion material of the present embodiment contains the compound (B), the total content of the compound (B) in the color conversion material only needs to satisfy the condition III, but is preferably 0.001 to 20% by mass, more preferably 0.01 to 10% by mass, and still more preferably 0.01 to 5% by mass. However, when the compound (B) contains the polymer compound (AB), the content of the polymer compound (AB) is treated as the content of the compound (A).

[0167] [1-2-1. Low molecular weight compound (B)] The low molecular weight compound (B) only needs to satisfy the condition I, but is preferably an organic boron compound. Further, the organic boron compound is preferably a low molecular weight compound represented by any of the formulas (7) to (9), and more preferably a low molecular weight compound represented by the formula (7) or the formula (9).

[0168] (Low molecular weight compound represented by formula (7) or formula (8)) The number of carbon atoms in the aromatic hydrocarbon rings represented by the A ring, B ring, and C ring, excluding the number of carbon atoms in the substituents, is usually 6 to 60, preferably 6 to 18, more preferably 6 to 10, and still more preferably 6. Examples of the aromatic hydrocarbon ring include benzene, fluorene, naphthalene, anthracene, and phenanthrene, and benzene is preferred.

[0169] The number of carbon atoms in the aromatic heterocyclic rings represented by Ring A, Ring B, and Ring C, excluding the number of carbon atoms in the substituents, is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15. Examples of the aromatic heterocyclic ring include pyridine, diazabenzene, azanaphthalene, diazanaphthalene, carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, and thiophene.

[0170] As the substituents that Ring A, Ring B, and Ring C may have, since the color conversion efficiency of this embodiment is more excellent, they are preferably an alkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and more preferably an alkyl group, an aryl group, or a substituted amino group. These groups may have substituents.

[0171] The more detailed structures (CA, CB, and CC) of Ring A, Ring B, and Ring C will be described below.

[0172]

Chemical formula

[0173] Examples of the detailed structure (CA) of Ring A include structures represented by Formula (CA01) to Formula (CA38). Since the color conversion efficiency of this embodiment is more excellent, the structure is preferably represented by Formula (CA01) to Formula (CA19), more preferably represented by Formula (CA01) to Formula (CA05), and even more preferably represented by Formula (CA01).

[0174]

Chemical formula

[0175]

Chemical formula

[0176]

Chemical formula

[0177] [Chemical formula]

[0178] [In the formula, R Y2 and R a represent the same meaning as described above. R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. These groups may have substituents. When there are a plurality of R Y4 's, they may be the same or different. The hydrogen atom in the formula may be replaced by a substituent that the A ring may have.]

[0179] As the detailed structure (CB) of the B ring, for example, the structures represented by formula (CB01) to formula (CB24) can be mentioned. Since the color conversion efficiency of this embodiment is more excellent, the structure represented by formula (CB01) to formula (CB13) is preferable, the structure represented by formula (CB01) to formula (CB05) is more preferable, and the structure represented by formula (CB01) is even more preferable.

[0180] [Chemical formula]

[0181] [Chemical formula]

[0182] [Chemical formula]

[0183] [In the formula, R Y2 , R Y4 and R a represent the same meaning as described above. The hydrogen atom may be replaced by a substituent that the B ring may have. In formula (7), * is bonded to a hydrogen atom or a substituent, In formula (8), * is Y 3 and represents the bonding position with.]

[0184] Specific examples of the structure of the C ring (CC) include structures represented by formula (CC01) to formula (CC24), preferably structures represented by formula (CC01) to formula (CC13), more preferably structures represented by formula (CC01) to formula (CC05), and even more preferably the structure represented by formula (CC01).

[0185] [Chemical formula]

[0186] [Chemical formula]

[0187] [Chemical formula]

[0188] [In the formula, R Y2 , R Y4 and R a have the same meaning as described above. The hydrogen atom may be replaced by a substituent that the C ring may have. In formula (7), * is bonded to a hydrogen atom or a substituent, In formula (8), * is Y 3 and represents the bonding position with.]

[0189] In formula (CA02) to formula (CA05), formula (CB02) to formula (CB05), and formula (CC02) to formula (CC05), the two R's in the group represented by -C(R Y2 )2- Y2The combination is preferably such that both are an alkyl group or a cycloalkyl group; both are an aryl group; both are 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, one is an alkyl group or a cycloalkyl group and the other is an aryl group. These groups may have substituents. -C(R Y2 )2- In the group represented by, the two R Y2 are bonded to each other to form a ring together with the carbon atom, and the group represented by -C(R Y2 )2- is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4). These groups may have substituents.

[0190] [Chemical formula]

[0191] In formula (CA09) to formula (CA12), formula (CB08) to formula (CB10), and formula (CC08) to formula (CC10), -C(R Y2 )=C(R Y2 )- In the group represented by, the two R Y2 The combination is preferably such that both are an alkyl group or a cycloalkyl group; or one is an alkyl group or a cycloalkyl group and the other is an aryl group; These groups may have substituents.

[0192] In formula (CA20) to formula (CA26), formula (CB14) to formula (CB18), and formula (CC14) to formula (CC18), 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. These groups may have substituents.

[0193] In the low-molecular compound represented by the formula (7) or the formula (8), as the combination of the A ring, the B ring, and the C ring, since the color conversion efficiency of the present embodiment is more excellent, preferably, the A ring has a structure represented by the formula (CA01) to the formula (CA05), the B ring has a structure represented by the formula (CB01) to the formula (CB05), and the C ring has a structure represented by the formula (CC01) to the formula (CC05). More preferably, the A ring has a structure represented by the formula (CA01), the B ring has a structure represented by the formula (CB01) to the formula (CB05), and the C ring has a structure represented by the formula (CC01) to the formula (CC05). Even more preferably, the A ring has a structure represented by the formula (CA01), the B ring has a structure represented by the formula (CB01), and the C ring has a structure represented by the formula (CC01).

[0194] Y 2 and Y 3 is preferably -N(-Ry)- or a sulfur atom, and more preferably -N(-Ry)-

[0195] Y 2 and Y 3 At least one of them is preferably -N(-Ry)- because the color conversion efficiency of the present embodiment is more excellent. Y 2 and Y 3 It is more preferable that both are -N(-Ry)-

[0196] Ry is preferably a hydrogen atom, an aryl group which may have a substituent, or a monovalent heterocyclic group which may have a substituent because the color conversion efficiency of the present embodiment is more excellent. More preferably, it is a hydrogen atom or an aryl group which may have a substituent. Even more preferably, it is an aryl group which may have a substituent

[0197] When Ry is bonded to the A ring, the B ring, or the C ring via a linking group, examples of the linking group include a direct bond; a divalent group such as -O-, -S-, -CH2-; a trivalent group such as a boron atom; and the like

[0198] When Ry is bonded to the A ring, B ring, or C ring via a trivalent group, usually, the A ring is linked to the substituent on the A ring, the B ring is linked to the substituent on the B ring, or the C ring is linked to the substituent on the C ring.

[0199] As the low-molecular-weight compound represented by formula (7) or formula (8), for example, a compound represented by the following formula is preferable.

[0200] [Chemical formula]

[0201] (Method for producing the low-molecular-weight compound represented by formula (7) or formula (8)) The low-molecular-weight compound represented by formula (7) or formula (8) is available from Aldrich, Luminescence Technology Corp., etc. Otherwise, for example, it can be synthesized according to the methods described in WO 2007 / 063754, WO 2008 / 056746, WO 2011 / 032686, WO 2012 / 096263, JP-A-2009-227663, JP-A-2010-275255, Advanced Materials, Vol. 26, pp. 7931-7958, 2014.

[0202] (Low-molecular-weight compound represented by formula (9)) R 1 ~R 9 The number of carbon atoms of the alkyl group represented by is preferably 1 to 20, more preferably 1 to 8, from the viewpoints of availability and cost.

[0203] R 1 ~R 9 The number of carbon atoms of the cycloalkyl group represented by is preferably in the range of 3 to 20.

[0204] R 1 ~R 9 The number of carbon atoms of the monovalent heterocyclic group represented by is preferably 2 to 20.

[0205] R 1~R 9 The number of carbon atoms in the alkenyl group represented by is preferably 2 to 20.

[0206] R 1 ~R 9 The number of carbon atoms in the cycloalkenyl group represented by is preferably 3 to 30, more preferably 4 to 20.

[0207] R 1 ~R 9 The number of carbon atoms in the alkynyl group represented by is preferably 2 to 20.

[0208] R 1 ~R 9 The number of carbon atoms in the alkoxy group represented by is preferably 1 to 20.

[0209] R 1 ~R 9 The number of carbon atoms in the alkylthio group represented by is preferably 1 to 20.

[0210] R 1 ~R 9 The number of carbon atoms in the aryloxy group represented by is preferably 6 to 40.

[0211] R 1 ~R 9 The number of carbon atoms in the arylthio group represented by is preferably 6 to 40.

[0212] R 1 ~R 9 The number of carbon atoms in the aryl group represented by is preferably 6 to 40, more preferably 6 to 30.

[0213] R 1 ~R 9The aryl group represented by is preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, pyrenyl group, fluoranthenyl group, or triphenylenyl group, more preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, or anthracenyl group, still more preferably a phenyl group, biphenyl group, terphenyl group, or naphthyl group, particularly preferably a phenyl group, biphenyl group, or terphenyl group, and most preferably a phenyl group.

[0214] R 1 ~R 9 When the aryl group represented by is further substituted with an aryl group, the aryl group as the substituent is preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, or anthracenyl group, more preferably a phenyl group, biphenyl group, terphenyl group, or naphthyl group, and still more preferably a phenyl group.

[0215] R 1 ~R 9 The number of carbon atoms of the heteroaryl group represented by is preferably 2 to 40, more preferably 2 to 30.

[0216] R 1 ~R 9 The heteroaryl group represented by is preferably a pyridyl group, furanyl group, thienyl group, quinolinyl group, pyrimidyl group, triazinyl group, benzofuranyl group, benzothienyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, or phenanthrolinyl group, more preferably a pyridyl group, furanyl group, thienyl group, or quinolinyl group, and still more preferably a pyridyl group.

[0217] When the heteroaryl group is further substituted with a heteroaryl group, the heteroaryl group as the substituent is preferably a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group, more preferably a pyridyl group, a furanyl group, a thienyl group, or a quinolinyl group, and even more preferably a pyridyl group.

[0218] When the amino group is a substituted amino group, the substituent of the amino group is preferably an aryl group, a heteroaryl group, or an alkyl group. The aryl group as the substituent is preferably a phenyl group or a naphthyl group. The heteroaryl group as the substituent is preferably a pyridyl group or a quinolinyl group. R 1 ~R 9 The number of carbon atoms of the substituted amino group represented by is preferably 2 to 50, more preferably 6 to 40, and even more preferably 6 to 30.

[0219] The phosphine oxide group is a group represented by -P(=O)R 10 R 11 is a group represented by. R 10 and R 11 are the same as R 1 ~R 9 represents the same meaning.

[0220] R 1 ~R 9The substituents it has include, in addition to the above-mentioned substituents, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a sulfonic acid group, and a phosphine oxide group. These substituents may further have substituents.

[0221] R 1 ~R 9 When adjacent groups of R 1 ~R 9 are bonded directly or via a linking group to form a ring, it means that any two adjacent groups among R 1 and R 2 are bonded to each other to form a conjugated or non-conjugated ring. The atoms constituting this ring may contain a heteroatom selected from nitrogen, oxygen, sulfur, phosphorus, and silicon. Further, these rings may be condensed with another ring.

[0222] The low-molecular compound represented by formula (9) exhibits a high luminescence quantum yield and has a small half-value width of the emission spectrum, so that both efficient color conversion and high color purity can be achieved. Further, the low-molecular compound represented by formula (9) can adjust various properties and physical properties such as luminescence efficiency, color purity, thermal stability, light stability, and dispersibility by having appropriate R 1 ~R 9 . For example, compared with the case where all of R 1 , R 3 , R 4 and R 6 are hydrogen, the case where at least one of R 1 , R 3 , R 4 and R 6 is an alkyl group, an aryl group, or a heteroaryl group shows higher thermal stability and light stability.

[0223] R 1, R 3 , R 4 and R 6 When at least one of them is an alkyl group, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Among these, from the viewpoint of improving thermal stability, the alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group. Also, from the viewpoint of preventing concentration quenching and improving the luminescence quantum yield, the alkyl group is preferably a sterically bulky tert-butyl group. Further, from the viewpoints of ease of synthesis and availability of raw materials, the alkyl group is preferably a methyl group.

[0224] R 1 , R 3 , R 4 and R 6 When at least one of them is an aryl group, the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, more preferably a phenyl group or a biphenyl group, and even more preferably a phenyl group.

[0225] R 1 , R 3 , R 4 and R 6 When at least one of them is a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a quinolinyl group, or a thienyl group, more preferably a pyridyl group or a quinolinyl group, and even more preferably a pyridyl group. preferably.

[0226] R 1 , R 3 , R 4 and R 6 From the viewpoint of enhancing solubility in the solvent, all of them are preferably alkyl groups. In this case, from the viewpoints of ease of synthesis and availability of raw materials, the alkyl group is preferably a methyl group.

[0227] R 1 、R 3 、R 4 and R 6 are preferably an aryl group or a heteroaryl group, more preferably an aryl group, from the viewpoint of obtaining high thermal stability and light stability.

[0228] There are substituents that improve multiple properties, but the substituents that exhibit sufficient performance in all cases are limited. In particular, it is difficult to achieve both high luminous efficiency and high color purity. Therefore, by introducing a plurality of types of substituents into the low-molecular compound represented by the formula (9), it is possible to obtain a compound with balanced luminescence characteristics and color purity.

[0229] In particular, when all of R 1 、R 3 、R 4 and R 6 are aryl groups, for example, R 1 ≠R 4 、R 3 ≠R 6 、R 1 ≠R 3 or R 4 ≠R 6 etc., it is preferable that R 1 、R 3 、R 4 and R 6 are not the same group as each other. Here, "≠" indicates that the groups have different structures. For example, R 1 ≠R 4 means that R 1 and R 4 are groups with different structures. As a result, the low-molecular compound represented by the formula (9) has both an aryl group that affects color purity and an aryl group that affects luminous efficiency, enabling fine adjustment.

[0230] Among them, R 1 ≠R 3 or R 4 ≠R 6It is preferable from the viewpoint of improving the luminous efficiency and color purity in a well-balanced manner. In this case, for the low-molecular compound represented by the formula (9), one or more aryl groups that affect the color purity can be introduced into the pyrrole rings on both sides, and aryl groups that affect the luminous efficiency can be introduced at other positions, so that both of these properties can be improved to the maximum extent. Also, R 1 ≠R 3 or R 4 ≠R 6 In the case of, from the viewpoint of improving both the heat resistance and the color purity, it is more preferable that R 1 =R 6 and R 3 =R 4 is.

[0231] As the aryl group that mainly affects the color purity, an aryl group substituted with an electron-donating group is preferable. An electron-donating group is a group that donates electrons to the substituted atomic group by an inductive effect or a resonance effect in organic electronics theory. Examples of electron-donating groups include those having a negative value as the substituent constant (σp (para)) of the Hammett rule. The substituent constant (σp (para)) of the Hammett rule can be cited from the 5th revised edition of the Basic Edition of Chemical Handbook (page II-380).

[0232] Specific examples of the electron-donating group include, for example, an alkyl group (σp of methyl group: -0.17), an alkoxy group (σp of methoxy group: -0.27), and an amino group (-NH2's σp: -0.66), etc. The electron-donating group is preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, and more preferably a methyl group, an ethyl group, a tert-butyl group, or a methoxy group. Among these, from the viewpoint of good dispersibility and preventing quenching due to aggregation of molecules, the electron-donating group is preferably a tert-butyl group or a methoxy group. Also, from the viewpoint of mainly improving the luminous efficiency, the electron-donating group is preferably a bulky group such as a tert-butyl group and a methoxy group.

[0233] The substitution position of the electron-donating group in the aryl group is preferably the meta or para position with respect to the bond position with the pyrromethene skeleton, since it is necessary to suppress bond twisting in order to increase the photostability of the low molecular weight compound represented by formula (9).

[0234] R 1 , R 3 , R 4 and R 6 When all of R are aryl groups, 1 , R 3 , R 4 and R 6 is preferably a phenyl group. 1 , R 3 , R 4 and R 6 are more preferably selected from the following Ar-1 to Ar-6. In this case, R 1 , R 3 , R 4 and R 6 The combination is not particularly limited.

[0235] [ka]

[0236] R 2 and R 5 is preferably a hydrogen atom, an alkyl group, a carbonyl group, an oxycarbonyl group, or an aryl group. Among these, from the viewpoint of obtaining high thermal stability, R 2 and R 5 is preferably hydrogen or an alkyl group. From the viewpoint of easily obtaining a narrow half-width in the emission spectrum, R 2 and R 5 is preferably a hydrogen atom.

[0237] R 8 and R 9is preferably an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a fluorine atom, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group, a fluorine-containing aryl group, a fluorine-containing alkoxy group, a fluorine-containing aryloxy group, or a cyano group. Among these, since it is stable against excitation light and a higher fluorescence quantum yield can be obtained, R 8 and R 9 are preferably a fluorine atom, a cyano group, or a fluorine-containing aryl group. From the viewpoint of easy synthesis, R 8 and R 9 are preferably a fluorine atom or a cyano group. Further, from the viewpoint of improving durability, it is preferable that one or both of R 8 and R 9 is a cyano group.

[0238] Here, the fluorine-containing aryl group is an aryl group containing fluorine, and examples thereof include a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group. The fluorine-containing heteroaryl group is a heteroaryl group containing fluorine, and examples thereof include a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group. The fluorine-containing alkyl group is an alkyl group containing fluorine, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.

[0239] Further, in formula (9), X is preferably C-R 7 from the viewpoint of photo-stability. When X is C-R 7 , the substituent R 7 greatly affects the decrease in the emission intensity of the low-molecular compound represented by formula (9) over time. Specifically, when R 7 is hydrogen, since the reactivity of this site is high, this site easily reacts with moisture and oxygen in the air. This causes the decomposition of the low-molecular compound represented by formula (9). Also, R 7When the substituent is one with a high degree of freedom of movement of the molecular chain, such as an alkyl group for example, the reactivity decreases. However, in the color conversion film described later, the low molecular compound represented by the formula (9) aggregates over time, resulting in a decrease in the emission intensity due to concentration quenching. Therefore, R 7 is preferably a group that is rigid and has a low degree of freedom of movement and is less likely to cause aggregation. Specifically, it is preferably an aryl group or a heteroaryl group.

[0240] From the viewpoint of giving a higher fluorescence quantum yield, being less likely to thermally decompose, and having good photostability, X is C-R 7 and R 7 is preferably an aryl group. The aryl group preferably does not affect the emission wavelength and is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group.

[0241] Furthermore, in order to enhance the photostability of the low molecular compound represented by the formula (9), it is necessary to appropriately suppress the torsion of the carbon-carbon bond between R 7 and the pyromethene skeleton. If the torsion of the carbon-carbon bond between R 7 and the pyromethene skeleton is excessively large, the reactivity with respect to the excitation light increases and the photostability decreases, for example. From such a viewpoint, R 7 is preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, more preferably a phenyl group, a biphenyl group, or a terphenyl group, and even more preferably a phenyl group.

[0242] Also, R 7 is preferably a moderately bulky substituent from the viewpoint of suppressing molecular aggregation and improving the emission efficiency and durability.

[0243] A more preferable example of such a bulky substituent is the structure of R 7 represented by the formula (10).

[0244]

Chemical formula

[0245] In formula (10), r is selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a sulfonic acid group, and a phosphine oxide group. These groups may have substituents. k is an integer from 1 to 3. When k is 2 or more, the plurality of r's may be the same or different.

[0246] From the viewpoint of being able to provide a higher luminescence quantum yield, r is preferably an aryl group. Among these aryl groups, particularly, a phenyl group and a naphthyl group can be given as preferred examples. When r is an aryl group, k in formula (10) is preferably 1 or 2, and more preferably 2 from the viewpoint of further suppressing the aggregation of the molecule. Furthermore, when k is 2 or more, at least one of r is preferably substituted with an alkyl group, and more preferably substituted with a methyl group, an ethyl group, or a tert-butyl group from the viewpoint of thermal stability.

[0247] Also, from the viewpoints of controlling the fluorescence wavelength and absorption wavelength or enhancing the compatibility with the solvent, r is preferably an alkyl group, an alkoxy group, or a halogen atom, and more preferably a methyl group, an ethyl group, a tert-butyl group, or a methoxy group. Also, from the viewpoint of enhancing the dispersibility and preventing quenching due to the aggregation of the molecules, r is preferably a tert-butyl group or a methoxy group.

[0248] Also, as another embodiment of the low molecular weight compound represented by formula (9), R 1 ~R 7It is preferable that at least one of them is an electron-withdrawing group. In particular, R 1 ~R 6 at least one of which is an electron -withdrawing group; R 7 is an electron-withdrawing group; or R 1 ~R 6 at least one of which is an electron-withdrawing group, and R 7 is an electron-withdrawing group; is preferable. By introducing an electron-withdrawing group into the pyromethene skeleton of the low-molecular compound represented by the formula (9), the electron density of the pyromethene skeleton can be significantly decreased. Thereby, the stability of the above compound against oxygen is further improved, and as a result, the durability of the low-molecular compound represented by the formula (9) can be further improved.

[0249] An electron-withdrawing group is also referred to as an electron-accepting group. In organic electronic theory, it is an atomic group that attracts electrons from the substituted atomic group by an inductive effect or a resonance effect. Examples of electron-withdrawing groups include those having a positive value as the substituent constant (σp (para)) of the Hammett rule. The substituent constant (σp (para)) of the Hammett rule can be cited from the 5th revised edition of the Basic Edition of Chemical Handbook (page II-380). Although the phenyl group also has an example of taking a positive value as described above, in the present disclosure, the phenyl group is not included in the electron-withdrawing group.

[0250] Examples of electron-withdrawing groups include, for example, -F (σp: +0.06), -Cl (σp: +0.23), -Br (σp: +0.23), -I (σp: +0.18), -CO2R 12 (σp: when R 12 is an ethyl group +0.45), -CONH2 (σp: +0.38), -COR 12 (σp: when R 12 is a methyl group +0.49), -CF3 (σp: +0.50), -SO2R 12 (σp: when R 12 is a methyl group +0.69), and -NO2 (σp: +0.81), etc. R 12Each independently represents a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 ring-forming carbon atoms, a heterocyclic group having 5 to 30 ring-forming atoms, an alkyl group having 1 to 30 carbon atoms, or a cycloalkyl group having 1 to 30 carbon atoms.

[0251] In formula (9), R 2 and R 5 It is preferable that at least one of them is an electron-withdrawing group. R in formula (9) 2 and R 5 are substitution positions that greatly affect the electron density of the pyromethene skeleton. By introducing an electron-withdrawing group into R 2 and R 5 the electron density of the pyromethene skeleton can be efficiently reduced, and the stability against oxygen is further improved, so that the durability can be further improved.

[0252] Furthermore, in formula (9), it is more preferable that R 2 and R 5 are electron-withdrawing groups. This is because the stability of the low-molecular compound represented by formula (9) against oxygen is further improved, and the durability can be greatly improved.

[0253] As the electron-withdrawing group, a group containing a fluorine atom is preferable. By being a group containing a fluorine atom, the electron density of the pyromethene skeleton can be further reduced, the stability of the low-molecular compound represented by formula (9) against oxygen is improved, and the durability can be improved.

[0254] Preferable electron-withdrawing groups include fluorine, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, an acyl group, an oxycarbonyl group, an amide group, a sulfonyl group, a sulfonic acid ester group, a sulfonamide group, and a cyano group. These electron-withdrawing groups are preferable because they are chemically difficult to decompose.

[0255] More preferable electron-withdrawing groups include fluorine-containing alkyl groups, acyl groups, oxycarbonyl groups, amide groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, and cyano groups. This is because these electron-withdrawing groups prevent concentration quenching and lead to the effect of improving the luminescence quantum yield. Among these, the particularly preferable electron-withdrawing group is the oxycarbonyl group.

[0256] Even more preferable electron-withdrawing groups include fluorine-containing acyl groups, fluorine-containing ester groups, fluorine-containing amide groups, fluorine-containing sulfonyl groups, fluorine-containing sulfonic acid ester groups, and fluorine-containing sul fonamide groups. These electron-withdrawing groups can efficiently reduce the electron density of the pyromethene boron complex skeleton, and as a result of improving the stability of the low-molecular-weight compound represented by formula (9) against oxygen, the durability of the low-molecular-weight compound represented by formula (9) can be further improved.

[0257] Among them, from the viewpoint of improving durability without reducing color purity, it is preferable that at least one of R 2 and R 5 is an oxycarbonyl group. In particular, from the viewpoint of improving durability, it is more preferable that both R 2 and R 5 are oxycarbonyl groups.

[0258] One preferable example of the low-molecular-weight compound represented by formula (9) is a case where R 1 , R 3 , R 4 and R 6 are alkyl groups, X is C-R 7 , and R 7 is a group represented by formula (10). In this case, r in formula (10) is particularly preferably a phenyl group.

[0259] Also, another preferable example of the low-molecular-weight compound represented by formula (9) is a case where R 1 , R 3 , R 4 and R 6is selected from the above-mentioned Ar-1 to Ar-6, and X is C-R 7 wherein 7 R is a group represented by the formula (10). In this case, r in the formula (10) is preferably a tert-butyl group or a methoxy group, and more preferably a methoxy group.

[0260] Another preferred example of the low molecular weight compound represented by the formula (9) is that 1 R 3 R 4 and R 6 are alkyl groups, R 2 and R 5 are oxycarbonyl groups, X is C-R 7 wherein 7 R is a group represented by the formula (10). In this case, r in the formula (10) is particularly preferably a phenyl group.

[0261] Another preferred example of the low molecular weight compound represented by the formula (9) is that 1 R 3 R 4 and R 6 are selected from the above-mentioned Ar-1 to Ar-6, R 2 and R 5 are oxycarbonyl groups, X is C-R 7 wherein 7 R is a group represented by the formula (10). In this case, 7 r in the formula (10) is preferably a tert-butyl group or a methoxy group, and more preferably a methoxy group.

[0262] As the low molecular weight compound represented by the formula (9), for example, a compound represented by the following formula is preferred.

[0263]

Chemical formula

[0264]

Chemical formula

[0265] [Chemical]

[0266] [Chemical]

[0267] [Chemical]

[0268] [Chemical]

[0269] [Chemical]

[0270] [Chemical]

[0271] [Chemical]

[0272] [Chemical]

[0273] (Method for producing the low molecular weight compound represented by formula (9)) The low molecular weight compound represented by formula (9) can be synthesized, for example, by the method described in JP-T-8-509471 or JP-A-2000-208262. That is, the target product can be obtained by reacting a pyromethene compound with a metal salt in the presence of a base.

[0274] A low molecular weight compound represented by formula (9), wherein R in the formula 8 and R 9 The pyromethene-boron fluoride complex in which is a fluorine atom is described, for example, in J. Org. Chem., vol. 64, No. 21, pp. 7813-7819 (1999), Angew. Chem., Int. Ed. Engl., vol. 36, pp. 1333-1335 (1997), etc. It can be synthesized according to the method described. That is, after heating the compound represented by formula (11) and the compound represented by formula (12) in 1,2-dichloroethane in the presence of phosphorus oxychloride, the compound represented by formula (9) is obtained by reacting with the compound represented by formula (13) in 1,2-dichloroethane in the presence of triethylamine. A low molecular weight compound can be synthesized. In formulas (11) to (13), R 1 ~R 9 is the same as the above description, and J represents a halogen atom.

[0275]

Chemical formula

[0276] Furthermore, when introducing an aryl group or a heteroaryl group, a method of forming a carbon-carbon bond using a coupling reaction between a halogenated derivative and a boronic acid or a boronic acid esterified derivative can be mentioned. Similarly, when introducing an amino group or a carbazolyl group, for example, a method of forming a carbon-nitrogen bond using a coupling reaction between a halogenated derivative and an amine or a carbazole derivative under a metal catalyst such as palladium can be mentioned.

[0277] 〔1-2-2. High molecular compound (AB)〕 The high molecular compound (AB) is a high molecular compound (AB) containing one or more of the above-described structural units (A) and one or more of the structural units (B) that satisfy condition II, and also corresponds to the high molecular compound (A). The high molecular compound (AB) may contain these structural units in any of the main chain, side chain, and terminal, but it is preferable to contain these structural units as repeating units in the main chain.

[0278] The structural unit (A) in the polymer compound (AB) has the same meaning as the structural unit (A) in the polymer compound (A), and the preferred embodiments are also the same.

[0279] The polymer compound (AB) may contain one or more other units other than the structural unit (A) and the structural unit (B). As the other structural units, the above-described structural unit (Y) and structural unit (Z) are preferred. The structural unit (Y) and the structural unit (Z) in the polymer compound (AB) have the same meaning as the structural unit (Y) and the structural unit (Z) in the polymer compound (A), respectively, and the preferred embodiments are also the same.

[0280] The structural unit (B) contained in the polymer compound (AB) is a structural unit that satisfies Condition II. The structural unit (B) is a structural unit different from the structural unit (A), and thus does not have the above-described condensed aromatic hydrocarbon skeleton. The structural unit (B) is preferably a structural unit derived from an organoboron compound, and more preferably a structural unit derived from a low-molecular compound represented by any one of Formula (7) to Formula (9). In the structural unit derived from the low-molecular compound represented by any one of Formula (7) to Formula (9), the low-molecular compound represented by any one of Formula (7) to Formula (9) has the same meaning as the low-molecular compound represented by any one of Formula (7) to Formula (9) shown as the low-molecular compound (B), and the preferred embodiments are also the same.

[0281] Since the total content of the structural unit (A) in the polymer compound (AB) is excellent in the stability of the polymer compound (AB), it is preferably 25 to 100 mol%, more preferably 30 to 99.99 mol%, still more preferably 40 to 90 mol%, particularly preferably 45 to 80 mol%, and especially preferably 47 to 70 mol% with respect to the total amount of all the structural units contained in the polymer compound (AB).

[0282] The total content of the constituent unit (B) in the polymer compound (AB) is preferably 0.001 to 20 mol%, more preferably 0.01 to 10 mol%, still more preferably 0.01 to 5 mol%, based on the total amount of all constituent units contained in the polymer compound (AB), because the stability of the polymer compound (AB) is excellent.

[0283] When the polymer compound (AB) contains the constituent unit (Y), the total content of the constituent unit (Y) in the polymer compound (AB) is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol%, particularly preferably 20 to 55 mol%, and most preferably 30 to 53 mol%, based on the total amount of all constituent units contained in the polymer compound (AB), because the stability of the polymer compound (AB) is excellent.

[0284] When the polymer compound (AB) contains the constituent unit (Z), the total content of the constituent unit (Z) in the polymer compound (AB) is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol%, particularly preferably 20 to 55 mol%, and most preferably 30 to 53 mol%, based on the total amount of all constituent units contained in the polymer compound (AB), because the stability of the polymer compound (AB) is excellent.

[0285] (Constituent unit derived from the low molecular compound represented by formula (7) or formula (8)) The constituent unit derived from the low molecular compound represented by formula (7) or formula (8), which is a preferred embodiment of the constituent unit (B), is a constituent unit obtained by removing y or more hydrogen atoms from the low molecular compound represented by formula (7) or formula (8). Here, y is an integer of 1 or more. Among the y hydrogen atoms removed from the low molecular compound represented by formula (7) or formula (8), 1 or more may be hydrogen atoms of the substituent. From the viewpoint of the ease of synthesis of the polymer compound, y is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 2.

[0286] As the structural unit derived from the low molecular weight compound represented by formula (7) or formula (8), for example, the structural units represented by formula (3-101) to formula (3-129) are preferable.

[0287]

Chem.

[0288]

Chem.

[0289]

Chem.

[0290]

Chem.

[0291]

Chem.

[0292]

Chem.

[0293]

Chem.

[0294] (Structural unit derived from the low molecular weight compound represented by formula (9)) The structural unit derived from the low-molecular compound represented by formula (9), which is a preferred embodiment of the structural unit (B), is a structural unit obtained by removing z or more hydrogen atoms from the low-molecular compound represented by formula (9). Here, z is an integer of 1 or more. Among the z hydrogen atoms removed from the low-molecular compound represented by formula (9), 1 or more may be hydrogen atoms of the substituent. From the viewpoint of ease of synthesis of the polymer compound, z is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 2.

[0295] As the structural unit derived from the low-molecular compound represented by formula (9), for example, the structural units represented by formula (BM-1) to formula (BM-11) are preferred.

[0296] [Chemical formula]

[0297] [1-2-3. Polymer compound (B)] The polymer compound (B) is a polymer compound (B) containing one or more of the above-described structural units (B). The polymer compound (B) may contain the structural unit (B) in any of the main chain, side chain, and terminal, but it is preferred to contain the structural unit (B) in the main chain as a repeating unit.

[0298] The structural unit (B) in the polymer compound (B) has the same meaning as the structural unit (B) in the polymer compound (AB), and its preferred embodiments are also the same.

[0299] The polymer compound (B) may contain one or more other units in addition to the structural unit (B). As the other structural units, the above-described structural units (Y) and (Z) are preferable. The structural units (Y) and (Z) in the polymer compound (B) are synonymous with the structural units (Y) and (Z) in the polymer compound (A), respectively, and their preferred embodiments are also the same. However, the polymer compound (B) is a compound that does not correspond to the polymer compound (A). Therefore, the structural units contained in the polymer compound (B) are units that do not have the above-described condensed aromatic hydrocarbon skeleton, that is, structural units that do not correspond to the structural unit (A).

[0300] Since the total content of the structural unit (B) in the polymer compound (B) is excellent in the stability of the polymer compound (B), it is preferably 0.001 to 20 mol%, more preferably 0.01 to 10 mol%, still more preferably 0.01 to 5 mol% with respect to the total amount of all the structural units contained in the polymer compound (B).

[0301] When the polymer compound (B) contains the structural unit (Y), since the total content of the structural unit (Y) in the polymer compound (B) is excellent in the stability of the polymer compound (B), it is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol% with respect to the total amount of all the structural units contained in the polymer compound (B).

[0302] When the polymer compound (B) contains the structural unit (Z), since the total content of the structural unit (Z) in the polymer compound (B) is excellent in the stability of the polymer compound (B), it is preferably 0.01 to 75 mol%, more preferably 0.01 to 70 mol%, still more preferably 10 to 60 mol% with respect to the total amount of all the structural units contained in the polymer compound (B).

[0303] [1-3. Composition Examples of Polymer Compound (A) and Polymer Compound (B)] Examples of the polymer compound (A) include polymer compounds PA-1 to PA-9 and PAB-1 to PAB-9 shown in Table 1. Note that PAB-1 to PAB-9 correspond to the polymer compound (AB) among the polymer compounds (A). Examples of the polymer compound (B) include polymer compounds PB-1 to PB-9 shown in Table 1.

[0304]

Table 1

[0305] The polymer compound (A) and 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 are preferably copolymers obtained by copolymerizing a plurality of types of raw material monomers.

[0306] The number average molecular weight (Mn) in terms of polystyrene of the polymer compound (A) and the polymer compound (B) is preferably 1.0×10 3 ~1.0×10 7 , more preferably 5.0×10 4 ~1.0×10 6 , still more preferably 1.0×10 4 ~5.0×10 5 and particularly preferably 2. 0×10 4 ~2.0×10 5 . The weight average molecular weight (Mw) in terms of polystyrene of the polymer compound (A) is preferably 1.0×10 3 ~1.0×10 7 , more preferably 5.0×10 4 ~1.0×10 6 , still more preferably 1.0×10 4 ~5.0×10 5 and particularly preferably 5.0×10 4 ~3.0×10 5 . In the present disclosure, the number average molecular weight and weight average molecular weight of the polymer compound are determined by size exclusion chromatography (SEC) as shown in the examples described later.

[0307] [1-4. Method for Producing Polymer Compound (A) and Polymer Compound (B)] The polymer compound (A) and the polymer compound (B) can be produced using known polymerization methods described in Chemical Reviews, Vol. 109, pp. 897-1091 (2009), etc. Known polymerization methods include, in addition to the above, polymerization methods by coupling reactions using transition metal catalysts such as Suzuki reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction, and Kumada reaction.

[0308] In the above polymerization method, as a method for charging monomers, there are a method of charging the total 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 at once, continuously, or in portions, and a method of charging the monomers continuously or in portions.

[0309] Examples of the transition metal catalyst include palladium catalysts and nickel catalysts.

[0310] The post-treatment of the polymerization reaction is carried out by known methods, 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 (AB) and the polymer compound (B) is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

[0311] In the examples described later, as an example of the method for producing the polymer compound (A), a polymerization method using a Suzuki coupling reaction using a palladium catalyst is shown.

[0312] [1-5. Other Components] The color conversion material of this embodiment may contain, as necessary and within a range that does not inhibit the effects of the present disclosure, one or more light-emitting materials such as coumarin dyes, rhodamine dyes, inorganic phosphors, fluorescent pigments, fluorescent dyes, quantum dots; and other components such as additives contained in the inks described later.

[0313] However, it is preferable that the color conversion material of this embodiment does not substantially contain a transition metal complex. "Does not substantially contain a transition metal complex" means that the color conversion material is not intentionally blended with a transition metal complex. For example, it does not exclude an embodiment in which the color conversion material unavoidably contains a transition metal complex used in the synthesis of a polymer compound. Specifically, the content of the transition metal complex in the color conversion material of this embodiment is preferably 1% by mass or less, more preferably 1.0×10 -2 % by mass or less.

[0314] The total content of other components in the color conversion material of this embodiment depends on the absorbance of compound (A), the transmittance of the color conversion film to be formed, etc., but is 1.0×10 with respect to a total of 100 parts by mass of compound (A) and compound (B). -3 ~30 parts by mass is preferable, 1.0×10 -2 ~15 parts by mass is more preferable, and 1.0×10 -1 ~10 parts by mass is even more preferable.

[0315] 〔2. Ink〕 The ink according to the second embodiment of the present disclosure contains the color conversion material of the first embodiment and a solvent. The ink of this embodiment is suitable for producing a color conversion film using a printing method such as an inkjet printing method and a nozzle printing method.

[0316] The viscosity of the ink of this embodiment may be adjusted according to the type of printing method. However, when applying it 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.

[0317] 〔2-1. Solvent〕 The solvent contained in the ink of this embodiment 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; etc. The solvent may be used alone or in combination of two or more.

[0318] The content of the solvent in the ink of this embodiment is usually 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass, based on 100 parts by mass in total of the compound (A) and the compound (B) contained in the color conversion material of this embodiment.

[0319] 〔2-2. Binder Resin〕 The ink of this embodiment may contain a binder resin in order to improve coatability, transparency, or heat resistance. Further, the ink of this embodiment may contain a curing agent and a curing accelerator together with the binder resin.

[0320] When the ink of this embodiment contains a binder, the content of the binder resin in the ink is usually 10 to 200 parts by mass, preferably 20 to 100 parts by mass, based on 100 parts by mass in total of the compound (A) and the compound (B) contained in the color conversion material of this embodiment.

[0321] Examples of the binder resin include known ones such as acrylic resin, methacrylic resin, polyimide resin, polyamide resin, polyurethane resin, epoxy resin, phenol resin, silicone resin, polyurea resin, fluororesin, polycarbonate resin, polyolefin resin, polyester resin, polystyrene resin, melamine resin, and cellulose. The binder resin may be used alone or in combination of two or more.

[0322] From the viewpoint of transparency, the binder resin is preferably at least one selected from the group consisting of acrylic resin, methacrylic resin, epoxy resin, silicone resin, and polyester resin. From the viewpoint of heat resistance, the binder resin is preferably at least one selected from the group consisting of acrylic resin, methacrylic resin, and polyester resin.

[0323] [2-3. Additives] The ink of this embodiment may contain one or more additives such as a binder resin, an antioxidant, a surface conditioner, a light stabilizer, a plasticizer, and light-scattering particles, if necessary.

[0324] When the ink contains additives, the total content of the additives in the ink is preferably 1.0×10 -3 to 30 parts by mass, more preferably 1.0×10 -2 to 15 parts by mass, and even more preferably 1.0×10 -1 to 10 parts by mass, based on 100 parts by mass in total of the compound (A) and the compound (B).

[0325] (Antioxidant) Examples of the antioxidant include phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol; and phosphorus antioxidants such as tris(2,4-di-tert-butylphenyl) phosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite; and the like. The antioxidant may be used alone or in combination of two or more.

[0326] (Surface conditioner) From the viewpoint of improving the surface smoothness of the color conversion film, the ink of the present embodiment preferably contains a surface conditioner. Examples of the surface conditioner include an antifoaming agent and a leveling agent, and specifically, an acrylic resin; a polysiloxane such as polydimethylsiloxane; a silicone oil; and a fluorine compound; and the like. The surface conditioner may be used alone or in combination of two or more.

[0327] (Light stabilizer) Examples of the light stabilizer include a tertiary amine, a catechol derivative, and a nickel compound. The light stabilizer may be used alone or in combination of two or more.

[0328] (Plasticizer) Examples of the plasticizer include dibutyl phthalate, dioctyl phthalate, and tricresyl; and the like. The plasticizer may be used alone or in combination of two or more.

[0329] (Light scattering particles) From the viewpoint of improving the light extraction efficiency, the ink of the present embodiment preferably contains light scattering particles. Examples of the light scattering particles include glass particles, titania particles, silica particles, alumina particles, silicone resin particles, zirconia particles, ceria particles, aluminum nitride particles, silicon carbide particles, silicon nitride particles, barium titanate particles, and acrylic resin particles; and the like. The light scattering particles may be used alone or in combination of two or more.

[0330] [3. Color conversion film] The color conversion film according to the third embodiment of the present disclosure includes the color conversion material of the first embodiment, and is a color conversion film that converts incident light into light having a longer wavelength than the incident light.

[0331] The thickness of the color conversion film of this embodiment may be appropriately set within a range in which incident light can be converted into a desired wavelength. Specifically, the thickness of the color conversion film is preferably 10 nm to 500 μm, more preferably 50 nm to 100 μm or less, and even more preferably 100 nm to 10 μm or less.

[0332] An example of the manufacturing method of the color conversion film of this embodiment will be described. The color conversion film of this embodiment can be manufactured by a method including a coating step of coating the ink of the second embodiment on a substrate and a drying step of drying the ink on the substrate. When the ink contains a thermosetting resin as a binder resin, the method may include a thermosetting step of heating and curing the thermosetting resin after the coating step. Further, when the ink contains a photocurable resin as a binder resin, the method may include a photocuring step of photocuring the photocurable resin after the coating step.

[0333] As the coating method of the ink in the coating step, known coating methods such as spin coating method, casting method, microgravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, and nozzle coating method can be appropriately adopted. For example, when forming or patterning a plurality of red conversion films and a plurality of green conversion films in a plurality of regions defined by partitions (banks), it is preferable to apply the ink by an inkjet printing method. The inkjet printing method is a coating method excellent in ink utilization efficiency and cost because ink is ejected only to necessary portions.

[0334] In the drying process, the drying method of the ink can be appropriately adopted from known drying methods such as hot air drying and infrared drying. The drying conditions are preferably a heating temperature of 40 to 200 °C and a heating time of 1 minute to 3 hours, and more preferably a heating temperature of 80 to 150 °C and a heating time of 1 minute to 1 hour.

[0335] After the color conversion film is produced, the color conversion film may be transferred to another substrate as needed. In this case, as simple methods, there are a method of performing replacement using a hot plate; and a method using a vacuum laminator or a dry film laminator; etc.

[0336] [4. Light-emitting device and display device] The color conversion material according to the first embodiment can be suitably used for applications of a light-emitting device or a display device, and particularly can be suitably used for a display device. In a display device, even if the light-emitting element has a long life, there is a problem that the image quality deteriorates as the luminance of the color conversion material decreases with the passage of the driving time. However, since the color conversion material according to the first embodiment has a long luminance life, it is possible to maintain the image quality of the display device for a long time.

[0337] The light-emitting device and the display device may include the color conversion material according to the first embodiment, but preferably include the color conversion film according to the third embodiment including the color conversion material.

[0338] In the light-emitting device and the display device, the color conversion material may be arranged so as to be in contact with the light source, or may be arranged on the light source via an arbitrary member or space. Examples of any member include various substrates and color filters. By using the color conversion film and the color filter of the third embodiment together, the color purity can be adjusted more easily. As the color filter, for example, known color filters containing pigments such as perylene pigments, lake pigments, azo pigments, quinacridone pigments, anthraquinone pigments, anthracene pigments, isoindoline pigments, isoindolinone pigments, phthalocyanine pigments, triphenylmethane basic dyes, indanthrone pigments, indophenol pigments, cyanine pigments, and dioxazine pigments can be used.

[0339] Examples of the main configurations of the light-emitting device and the display device having the color conversion film are shown below. (1) Light source / Color conversion film (2) Light source / Substrate / Color conversion film (3) Light source / Color conversion film / Substrate (4) Light source / Transparent substrate / Color conversion film / Substrate (5) Light source / Color conversion film / Color filter (6) Light source / Substrate / Color conversion film / Color filter (7) Light source / Color conversion film / Substrate / Color filter (8) Light source / Substrate / Color conversion film / Substrate / Color filter (9) Light source / Substrate / Color conversion film / Color filter / Substrate (10) Light source / Color conversion film / Color filter / Substrate

[0340] In addition to the above components, the light-emitting device and the display device of this embodiment preferably have optical films such as a diffusion plate, a reflection film, a conversion film, a polarization reflection film, a brightness enhancement film, and a light guide film as needed; and functional layers such as a light shielding layer, a planarization layer, and a gas barrier layer; etc. Further, when the display device is a liquid crystal display device, the display device preferably includes a liquid crystal cell provided with a color filter and further has the above-described optical film.

[0341] The light source can be any excitation light as long as it emits light that can be absorbed by the color conversion material. The light source that emits light that can be absorbed by the color conversion material is preferably a light source having a maximum emission at a wavelength of 400 to 500 nm, more preferably a light source having a maximum emission at a wavelength of 450 to 460 nm. Specific light sources include, for example, hot cathode tubes, cold cathode tubes, inorganic EL elements, organic EL elements, LED elements, and fluorescent lamps, and preferably LED elements. Further, when the light emitting device is used for a display device and illumination, from the viewpoint of enhancing the color purity of blue light, the light source is more preferably an LED element having a maximum emission in the above-described wavelength range. The light source may have a single emission peak or may have a plurality of emission peaks, but in order to enhance the color purity of light, it is preferably a light source having a single emission peak. Further, the light source may be a combination of a plurality of light sources having different emission peaks.

[0342] Examples of the display device include a liquid crystal display device and an organic EL display device, and preferably an organic EL display device. When the display device is a liquid crystal display device, the above-described light emitting device is preferably used as a backlight. When the display device is an organic EL display device, the above-described light emitting device is preferably used as a light emitting element for displaying an image, for example, in a matrix method and a segment method.

Example

[0343] Hereinafter, the present disclosure will be described in more detail with reference to examples, but the present disclosure is not limited to the following examples.

[0344] <Number average molecular weight and weight average molecular weight> In the examples, the number average molecular weight (Mn) 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 as a mobile phase. The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, 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.

[0345] <nmr> NMR was measured by the following method. 5 to 10 mg of the measurement sample was dissolved in approximately 0.5 mL of deuterated chloroform (CDCl3) or deuterated methylene chloride (CD2Cl2), and measured using an NMR apparatus (manufactured by Agilent Technologies, Inc. , product name: INOVA300 or MERCURY 400VX).

[0346] <Purity> As an index of the purity of the compound, the value of the HPLC area percentage was used. Unless otherwise specified, this value was the value at UV = 254 nm measured by HPLC (manufactured by Shimadzu Corporation, product name: LC-20A). 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 mass, and 1 to 10 μL was injected into HPLC according to the concentration. For the mobile phase of HPLC, the ratio of acetonitrile / tetrahydrofuran was changed from 100 / 0 to 0 / 100 (volume ratio) and used, and it was 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.

[0347] <lc-ms> LC-MS was measured by the following method. The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (manufactured by Agilent Technologies, Inc., trade name: 1100 LCMSD). The mobile phase of LC-MS was used while changing the ratio of acetonitrile and tetrahydrofuran, and flowed at a flow rate of 0.2 mL / min. As the column, L-column 2 ODS (3 μm) (manufactured by the Chemical Substances Evaluation and Research Institute, general incorporated foundation, inner diameter 2.1 mm, length 100 mm, particle size 3 μm) was used.

[0348] <tlc-ms> TLC-MS was measured by the following method. The measurement sample was dissolved in any one of solvents such as toluene, tetrahydrofuran or chloroform at an arbitrary concentration, applied onto a TLC plate for DART (manufactured by Techno Applications Co., Ltd., product name: YSK5-100), and measured using TLC-MS (manufactured by JEOL Ltd., product name: JMS-T100TD (The AccuTOF TLC)). The temperature of the helium gas during measurement was adjusted in the range of 200 to 400 °C.

[0349] <Evaluation of Luminance Lifetime> (Apparatus for Evaluating Luminance Lifetime) The evaluation of the luminance lifetime was performed by irradiating excitation light from the side of the synthetic quartz glass substrate of the measurement sample described later to cause the measurement sample to emit light. As the excitation light source, a laser diode NDB4216E (wavelength 450 to 460 nm) manufactured by Nichia Chemical Industries, Ltd. was used, and as the laser driver, ALP-7033CC of DATA SYSTEM was used. For measuring the light emission from the measurement sample, a color luminance meter CHROMA METER CS-200 manufactured by Konica Minolta, which is a light emission luminance measuring device, was used. A short-wavelength non-transmissive filter was installed at the photometric entrance of the light emission luminance measuring device so that light with a wavelength of 470 nm or less was not photometrically measured.

[0350] (Adjustment of Excitation Light Intensity of Excitation Light Source) In the evaluation of the luminance lifetime, the excitation light intensity of the excitation light source was adjusted so that the number of photons absorbed by each measurement sample described later was the same.

[0351] In order to calculate the condition under which the number of photons absorbed by each measurement sample is the same, Equation (I), Equation (II), and Equation (III) were used.

[0352] First, when the organic compound layer (color conversion layer) has the same thickness, the number of photons absorbed by the measurement sample is calculated from Equation (I).

[0353]

Equation

[0354] n ex-ab is the number of photons absorbed [pieces], and I ex is the intensity of the excitation light incident on the organic compound layer contained in the measurement sample, and I' ex is the intensity of the excitation light transmitted through the organic compound layer, and ε ph-ex is the energy per photon at the excitation light wavelength, and T represents the transmittance. Here, the transmittance indicated by T was measured using a Cary Series manufactured by Agilent Technologies, Inc. Specifically, the range of wavelengths from 300 to 700 nm was measured in 1 nm steps, and T was calculated from the simple average value in the range of wavelengths from 453 to 458 nm of the measurement data.

[0355] Second, under the above conditions, n representing the number of photons absorbed calculated from formula (I) ex-ab must be the same number (constant). That is, formula (II) is required.

[0356]

Equation

[0357] Substitute formula (II) into formula (I) and transform the formula by summarizing the constants, etc., then formula (III) is obtained, and the excitation light intensity can be determined from the transmittance of the measurement sample at the excitation light wavelength. That is, if const. in formula (III) is kept constant, I at which the number of photons absorbed by each measurement sample becomes the same from the transmittance T ex can be calculated.

[0358]

Equation

[0359] For example, when a certain measurement sample has a transmittance T1 = 0.2 (20%) and the light emission is measured with an excitation light intensity of I ex = 200 mW, the excitation light intensity for measurement using another measurement sample with a transmittance T2 = 0.25 (25%) while keeping the number of photons absorbed the same is calculated as follows. I ex =(1 - 0.2) / (1 - 0.25)×200 = 213.3 (mW)

[0360] <Synthesis Example 1: Synthesis of Compound 1D>

Chemical formula

[0361] (Stage 1: Synthesis of Compound 1A) After making the inside of the reaction vessel an argon atmosphere, 2,2'-(1,6-pyrenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] (91.0 g), methyl 5-bromo-2-iodobenzoate (143.5 g), tetrabutylammonium bromide (6.5 g), tetrakis(triphenylphosphine)palladium(0) (11.6 g), tris(dibenzylideneacetone)dipalladium(0) (3.1 g), potassium carbonate (77.1 g), ion-exchanged water (231 mL), and toluene (1366 mL) were added to the reaction vessel, the temperature was raised to 90°C, and the mixture was stirred at 90°C for 42 hours. After cooling the obtained reaction solution to 25°C, methanol (2731 mL) was added and filtered. The obtained solid was washed with hexane and then dried under reduced pressure at 50°C to obtain Compound 1A (122.8 g). The LC area percentage value of Compound 1A was 95.3%.

[0362] 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.23 (s, 2H), 8 .17 (d, 2H), 8.00 (d, 2H), 7.84 - 7.78 (m, 4H), 7.72 (d, 2H), 7.41 - 7.34 (m, 2H), 3.39 (s, 3H), 3.35 (s, 3H)

[0363] (Stage 2: Synthesis of Compound 1B) After making the inside of the reaction vessel an argon atmosphere, 3-bromo-3'-hexyl-1,1'-biphenyl (44.1 g) and tetrahydrofuran (441 mL) were added to the reaction vessel and cooled to -70°C. Thereto, a 1.6 M n-butyllithium hexane solution (88 mL) was slowly added, and the mixture was stirred at -70°C for 30 minutes. Thereto, Compound 1A (18.5 g) was added, the temperature was raised to 0°C, and the mixture was stirred for 1 hour. Thereafter, ion-exchanged water (370 mL) and toluene (370 mL) were added, the obtained reaction solution was heated to 25°C, and the aqueous layer was removed. The obtained organic layer was washed twice with ion-exchanged water, the obtained organic layer was 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 recrystallized from a mixed solvent of toluene and hexane. The obtained solid was recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50°C to obtain Compound 1B (30.0 g). The LC area percentage value of Compound 1B was 96.3%.

[0364] 1 1H-NMR (400 MHz, CD2Cl2) δ (ppm) = 7.79 (m, 4H), 7.58 (d, 4H), 7.47 - 7.01 (m, 38H), 2.59 - 2.41 (m, 10H), 1.60 - 1.50 (m, 8H), 1.33 - 1.19 (m, 24H), 0.88 - 0.78 (m, 12H)

[0365] (Stage 3: Synthesis of Compound 1C) After making the inside of the reaction vessel an argon atmosphere, Compound 1B (29.9 g) and methylene chloride (600 mL) were added to the reaction vessel and cooled to -70°C. Thereto, methanesulfonic acid (0.4 mL) was added, and the temperature was raised to 25°C while stirring. Thereafter, the mixture was allowed to stand at 25°C for 18 hours. Ion-exchanged water (299 mL) was added to the obtained reaction solution, and the aqueous layer was removed. The obtained organic layer was 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 (toluene) and dried under reduced pressure at 50°C to obtain Compound 1C (25.8 g). The LC area percentage value of Compound 1B was 97.3%.

[0366] 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.54 (d, 2H), 8.10 (q, 4H), 7.83 (s, 2H), 7.58 (q, 2H), 7.47 - 7.36 (m, 8H), 7.32 (d, 2H), 7.26 (t, 4H), 7.19 - 7.20 (m, 12H), 7.04 - 7.02 (m, 8H), 2.47 (t, 8H), 1.51 - 1.43 (m, 8H), 1.25 - 1.15 (m, 24H), 0.81 - 0.79 (m, 12H)

[0367] (Stage 4: Synthesis of Compound 1D) After making the inside of the reaction vessel a nitrogen atmosphere, Compound 1C (12.0 g), bis(pinacolato)diboron (6.2 g), potassium acetate (4.8 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.2 g), and 1,2-dimethoxyethane (120 mL) were added to the reaction vessel, the temperature was raised to 85 °C, and the mixture was stirred at 85 °C for 2 hours. After cooling the resulting reaction solution to 25 °C, toluene (120 mL) was added and the mixture was filtered through silica gel. To the resulting filtrate, ion-exchanged water (120 mL) was added and the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water and the resulting organic layer was concentrated under reduced pressure to obtain a crude product. Toluene (408 mL) was added to the obtained crude product and it was dissolved by raising the temperature to 50 °C. Activated carbon (2.6 g) was added to the dissolved solution and the mixture was filtered through silica gel. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was repeatedly recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50 °C to obtain Compound 1D (13.7 g). The LC area percentage value of Compound 1D was 98.3%.

[0368] 1 1H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.61 - 8.59 (d, 2H), 8.23 - 8.21 (d, 2H), 8.11 - 8.20 (d, 2H), 7.83 (d, 2H), 7.76 (s, 2H), 7.64 (s, 2H), 7.46 - 7.40 (m, 8H), 7.25 (t, 4H), 7.16 - 7.13 (m, 12H), 7.05 - 6.99 (m, 8H), 2.47 (t, 8H), 1.50 - 1.41 (m, 8H), 1.31 - 1.11 (m, 48H), 0.83 - 0.79 (m, 12H)

[0369] <Synthesis Example 2: Synthesis of Compound 2D>

Chemical Structure

[0370] (stage 1: Synthesis of Compound 2A) After making the inside of the reaction vessel a nitrogen atmosphere, 1-bromo-3,5-dihexylbenzene (50.0 g), bis(pinacolato)diboron (42.9 g), potassium acetate (22.6 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (2.5 g), and 1,2-dimethoxyethane (500 mL) were added to the reaction vessel, the temperature was raised to 85°C, and the mixture was stirred at 85°C for 4 hours. Potassium acetate (22.6 g) was added to the resulting reaction solution, the temperature was raised to 95°C, and the mixture was stirred at 95°C for 3 hours. After cooling the resulting reaction solution to 25°C, ion-exchanged water (500 mL) and normal heptane (250 mL) were added, and the aqueous layer was removed. Activated carbon (10 g) was added to the resulting organic layer, and silica gel filtration was performed. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. Acetonitrile (80 mL) cooled to 0°C was added to the obtained crude product, the mixture was stirred at 0°C for 30 minutes, and then filtered. The obtained solid was recrystallized from acetonitrile and dried under reduced pressure at 50°C to obtain Compound 2A (44.4 g). The LC area percentage value of Compound 2A was 98.7%. The above operation was repeated to secure the required amount of Compound 2A.

[0371] 1 H-NMR (400 MHz, CDCl3) δ (ppm) = 7.44 (s, 2H), 7.09 (s, 1H), 2.59 - 2.55 (t, 4H), 1.61 (m, 4H), 1.29 (m, 24H), 0.87 (m, 6H)

[0372] (stage 2: Synthesis of Compound 2B) After making the inside of the reaction vessel an argon atmosphere, Compound 2A (46.0 g), Vat Orange 3 (27.3 g), 40 mass% tetrabutylammonium hydroxide aqueous solution (114 mL), 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (0.5 g), tris(dibenzylideneacetone)dipalladium(0) (0.4 g), and toluene (655 mL) were added, the temperature was raised to 80 °C, and the mixture was stirred at 80 °C for 3 hours. After cooling the resulting reaction solution to 25 °C, toluene (300 mL) and ion-exchanged water (300 mL) were added, and the aqueous layer was removed. The obtained organic layer was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized from a mixed solvent of toluene and acetonitrile and dried under reduced pressure at 50 °C to obtain a crude product. The obtained crude product was recrystallized from ethyl acetate and isopropyl alcohol and dried under reduced pressure at 50 °C to obtain Compound 2B (27.8 g). The LC area percentage value of Compound 2B was 95.6%.

[0373] LC-MS (APCI positive): m / z = 795.4 [M + H] + 1 H-NMR (400 MHz, CDCl3) δ (ppm) = 8.76 (dd, 2H), 8.47 (s, 2H), 8.41 (dd, 2H), 7.82 (dd, 2H), 7.26 - 7.24 (m, 4H), 7.18 (brs, 2H), 2.74 (t, 8H), 1.77 - 1.70 (m, 8H), 1.46 - 1.32 (m, 24H), 0.93 (t, 12H)

[0374] (stage 3: Synthesis of Compound 2C) After making the inside of the reaction vessel a nitrogen atmosphere, 2B (15.0 g) of the compound, a 1 molar concentration borane-tetrahydrofuran complex solution (70 mL), and tetrahydrofuran (300 mL) were added to the reaction vessel, and the mixture was stirred at 25 °C for 20 hours. To the resulting reaction solution, a 1 molar concentration borane-tetrahydrofuran complex solution (35 mL) was added, and the mixture was stirred at 25 °C for 3 hours. Methanol (73 mL) was added to the resulting reaction solution, and the mixture was filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was washed with a mixed solvent of hexane and ethyl acetate and dried under reduced pressure at 50 °C to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), and then dried under reduced pressure at 50 °C to obtain 2C (2.7 g) of the compound. The LC area percentage value of compound 2C was 99.3%.

[0375] LC-MS (APCI positive): m / z = 765.4 [M+H] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.89 (s, 2H), 8.59 (d, 2H), 8.32 (d, 2H), 8.18 (s, 2H), 8.12 (t, 2H), 7.44 (d, 4H), 7.20 (brs, 2H), 2.77 (t, 8H), 1.81 - 1.74 (m, 8H), 1.51 - 1.32 (m, 24H), 0.94 (t, 12H)

[0376] (stage4: Synthesis of compound 2D) After making the inside of the reaction vessel a nitrogen atmosphere, 2C (2.7 g) of the compound and methylene chloride (102 mL) were added to the reaction vessel, and the mixture was cooled to 0 °C. N-Bromosuccinimide (1.3 g) and methylene chloride (3 mL) were added to the resulting reaction solution, and the mixture was stirred at 0 °C for 5 hours and at 40 °C for 20 hours. After cooling the resulting reaction solution to 25 °C, a saturated aqueous sodium sulfite solution (33 mL) and methylene chloride (20 mL) were added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, and the obtained organic layer was filtered. The obtained solid was dried under reduced pressure at 50 °C Thus, a crude product was obtained. The obtained solid was recrystallized repeatedly with toluene and filtered under reduced pressure at 50 °C to obtain Compound 2D (2.5 g). The LC area percentage value of Compound 2D was 98.9%.

[0377] LC-MS (APCI positive): m / z = 765.4 [M+H] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 9.17 (d, 2H), 8.74 (s, 2H), 8.40 (d, 2H), 8.23 (t, 2H), 7.43 - 7.41 (m, 4H), 7.24 (s, 2H), 2.79 (t, 8H), 1.82 - 1.75 (m, 8H), 1.52 - 1.33 (m, 24H), 0.94 (t, 12H)

[0378] <Synthesis Example 3: Synthesis of Compound 3E>

Chemical Structure

[0379] (stage1: Synthesis of Compound 3A) After making the inside of the reaction vessel a nitrogen atmosphere, 1,4-dibromonaphthalene (10.0 g), bis(pinacolato)diboron (26.6 g), potassium acetate (20.6 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1.3 g), and 1,2-dimethoxyethane (115 mL) were added to the reaction vessel, the temperature was raised to 85 °C, and the mixture was stirred at 85 °C for 30 minutes. After cooling the obtained reaction solution to 25 °C, ion-exchanged water (100 mL) was added and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, and the obtained organic layer was concentrated under reduced pressure to obtain a crude product. Acetonitrile (80 mL) was added to the obtained crude product, the mixture was stirred at 25 °C for 1 hour, and then filtered. The obtained solid was dried under reduced pressure at 50 °C to obtain Compound 3A (8.1 g). The LC area percentage value of Compound 3A was 97.3%.

[0380] TLC-MS (DART positive): m / z = 380 [M+H] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.69 (q, 2H), 7.96 (s, 2H), 7.47 (q, 2H), 1.39 (s, 24H)

[0381] (stage 2: Synthesis of Compound 3B) After making the inside of the reaction vessel an argon atmosphere, Compound 3A (6.5 g), methyl 5-bromo-2-iodobenzoate (12.8 g), tetrabutylammonium bromide (0.6 g), tetrakis(triphenylphosphine)palladium(0) (0.2 g), tris(dibenzylideneacetone)dipalladium(0) (49 mg), potassium carbonate (6.6 g), ion-exchanged water (20 mL), and toluene (98 mL) were added to the reaction vessel, the temperature was raised to 90 °C, and the mixture was stirred at 90 °C for 20 hours. After cooling the obtained reaction solution to 25 °C, ion-exchanged water (20 mL) was 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 crude product was washed with hexane to obtain a solid. The obtained solid was purified by silica gel column chromatography (toluene) and then dried under reduced pressure at 50 °C to obtain Compound 3B (6.0 g). The LC area percentage value of Compound 3B was 99.3%.

[0382] TLC-MS (DART positive): m / z = 555 [M+H] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.21 - 8.13 (d, 2H), 7.75 (d, 2H), 7.46 (m, 2H), 7.35 - 7.28 (m, 6H), 3.41 (m, 6H)

[0383] (stage 3: Synthesis of Compound 3C) After making the inside of the reaction vessel a nitrogen atmosphere, 1-bromo-3-hexylbenzene (11.7 g) and tetrahydrofuran (117 mL) were added to the reaction vessel and cooled to -60°C. A 1.6 M n-butyllithium hexane solution (30 mL) was slowly added thereto, and the mixture was stirred at -60°C for 30 minutes. Compound 3B (5.5 g) was added thereto, the temperature was raised to 0°C, and the mixture was stirred for 2 hours. Thereafter, ion-exchanged water (110 mL) and toluene (110 mL) were added, the resulting reaction solution was heated to 25°C, and the aqueous layer was removed. The obtained organic layer was washed twice with ion-exchanged water, the obtained organic layer was 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 hexane and chloroform), and then dried under reduced pressure at 50°C to obtain Compound 3C (9.1 g). The LC area percentage value of Compound 3C was 96.3%.

[0384] 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 7.46 - 7.44 (q, 2H), 7.26 - 7.18 (m, 4H), 7.12 - 7.06 (m, 8H), 7.02 - 6.97 (d, 4H), 6.94 (s, 2H), 6.88 - 6.79 (m, 6H), 6.47 (t, 2H), 2.61 - 2.42 (m, 8H), 2.42 (s, 2H), 1.50 (m, 8H), 1.23 (m, 24H), 0.88 - 0.76 (m, 12H)

[0385] (stage4: Synthesis of Compound 3D) After making the inside of the reaction vessel an argon atmosphere, Compound 3C (8.7 g) and methylene chloride (174 mL) were added to the reaction vessel and cooled to -70°C. Methanesulfonic acid (0.1 mL) was added thereto, and the temperature was slowly raised to 25°C while stirring. Thereafter, it was allowed to stand at 25°C for 12 hours. Ion-exchanged water (261 mL) was added thereto, and the aqueous layer was removed. The obtained organic layer was 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 hexane), and then dried under reduced pressure at 50°C to obtain a crude product. The obtained crude product was recrystallized from a mixed solvent of ethyl acetate and methanol to obtain Compound 3D (4.1 g). The LC area percentage value of Compound 3D was 97.9%.

[0386] LC-MS (APCI positive): m / z = 1118.2 [M+NH4] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.08 (s, 2H), 7.93 (d, 2H), 7.47 (d, 2H), 7.19 (s, 2H), 7.10 - 6.93 (m, 10H), 6.77 (s, 4H), 6.65 (d, 4H), 2.41 (t, 8H), 1.41 (m, 8H), 1.16 (m, 24H), 0.78 (t, 12H)

[0387] (stage5: Synthesis of Compound 3E) After setting the inside of the reaction vessel to a nitrogen atmosphere, compound 3D (2.0 g), bis(pinacolato)diboron (1.4 g), potassium acetate (1.1 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (65 mg), and 1,2-dimethoxyethane (23 mL) were added to the reaction vessel, the temperature was raised to 85°C, and the mixture was stirred at 85°C for 3 hours. After cooling the resulting reaction solution to 25°C, ion-exchanged water (20 mL) was added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, and the obtained organic layer was concentrated under reduced pressure to obtain a crude product. The obtained crude product was washed with methanol and then dried under reduced pressure at 50°C to obtain compound 3E (2.1 g). The LC area percentage value of compound 1A was 97.0%.

[0388] LC-MS (APCI positive): m / z = 1214.6 [M+NH4] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm): 8.19 (s, 2H), 8.08 (d, 2H), 7.75 (d, 2H), 7.52 (s, 2H), 7.06 (m, 4H), 7.02 (m, 4H), 6.91 (s, 2H), 6.83 (s, 4H), 6.63 (d, 4H), 2.39 (t, 8H), 1.41 (m, 8H), 1.27 (s, 24H), 1.15 (m, 24H), 0.74 (t, 12H)

[0389] <Synthesis Example 4: Synthesis of Compound 4D>

Chemical formula

[0390] (Stage 1: Synthesis of Compound 4A) After setting the inside of the reaction vessel to a nitrogen atmosphere, 6,12-dibromocresene (239.4 g), bis(pinacolato)diboron (377.9 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (22.3 g), potassium acetate (365.1 g) and dehydrated THF (2690 mL) were added, and the temperature was raised to 65°C It was stirred at 65 °C for 14 hours. The obtained reaction solution was concentrated under reduced pressure to obtain a crude product. To the obtained crude product, ion-exchanged water (2.4 L) was added, stirred at 25 °C for 20 minutes, and filtered. To the obtained solid, THF (1.2 L) was added, the temperature was lowered to 0 °C, stirred at 0 °C for 20 minutes, and then filtered. The obtained solid was dried under reduced pressure at 40 °C to obtain Compound 4A (273.0 g). The LC area percentage value of Compound 4A was 98.3%.

[0391] 1 1H-NMR (400 MHz, CD2Cl2) δ (ppm) = 9.33 (s, 2H), 8.90 (t, 4H), 7.73 - 7.63 (m, 4H), 1.47 (s, 24H)

[0392] (Stage 2: Synthesis of Compound 4B) After making the inside of the reaction vessel a nitrogen atmosphere, Compound 4A (150.0 g), methyl 5-bromo-2-iodobenzoate (233.4 g), tetrabutylammonium bromide (10.0 g), tetrakis(triphenylphosphine)palladium(0) (3.6 g), tris(dibenzylideneacetone)dipalladium(0) (889 mg), potassium carbonate (120.1 g), ion-exchanged water (360 mL), and toluene (227 mL) were added to the reaction vessel, the temperature was raised to 90 °C, and stirred at 90 °C for 29 hours. After the obtained reaction solution was cooled to 25 °C, the precipitated insoluble matter was filtered. The obtained solid was washed with methanol to obtain a crude product. The obtained crude product was recrystallized from toluene and washed with hexane. The obtained solid was dried under reduced pressure at 50 °C to obtain Compound 4C (135.8 g). The LC area percentage value of Compound 4C was 99.2%.

[0393] 1 1H-NMR (400 MHz, CD2Cl2) δ (ppm) = 8.76 - 8.73 (d, 2H), 8.54 (d, 2H), 8.25 (d, 2H), 7.87 - 7.81 (m, 2H), 7.67 (t, 2H), 7.57 - 7.49 (m, 4H), 7.45 - 7.42 (m, 2H), 3.40 - 3.38 (d, 6H)

[0394] (Stage 3: Synthesis of Compound 4C) After making the inside of the reaction vessel a nitrogen atmosphere, 3-bromo-3'-hexyl-1,1'-biphenyl (72.1 g) and tetrahydrofuran (690 mL) were added to the reaction vessel and cooled to -65°C. A 1.6 M n-butyllithium hexane solution (142 mL) was slowly added thereto, and the mixture was stirred at -65°C for 2 hours. Compound 4B (30.2 g) was added thereto, the temperature was raised to 0°C, and the mixture was stirred for 3 hours. Thereafter, ion-exchanged water (1.4 L) and toluene (1.4 L) were added, the obtained reaction solution was heated to 25°C, and then the aqueous layer was removed. The obtained organic layer was washed twice with ion-exchanged water, the obtained organic layer was 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 hexane and toluene), and then dried under reduced pressure at 50°C to obtain Compound 4C (42.3 g). The LC area percentage value of Compound 4C was 94.2%. The above operation was repeated to secure the required amount of Compound 4C.

[0395] (Stage 4: Synthesis of Compound 4D) After making the inside of the reaction vessel an argon atmosphere, Compound 4C (46.6 g), methylene chloride (93 mL) and methanesulfonic acid (1.7 g) were added to the reaction vessel and stirred at 25°C for 2 hours. Methanesulfonic acid (1.2 g) was added thereto and stirred at 25°C for 2 hours. Ion-exchanged water (1.4 L) was added to the obtained reaction solution, and the aqueous layer was removed. The obtained organic layer was washed twice with ion-exchanged water, the obtained organic layer was 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 recrystallized from a mixed solvent of toluene and hexane and dried under reduced pressure at 50°C to obtain Compound 4D (41.5 g). The LC area percentage value of Compound 4C was 99.9%.

[0396] LC-MS (APCI positive): m / z = 1506.4 [M+NH4] + 1 H-NMR (400 MHz, CD2Cl2) δ (ppm) = 9.30 (s, 2H), 8.86 - 8.84 (d, 2H), 8.25 - 8.23 (d, 2H), 7.72 (t, 2H), 7.64 - 7.61 (m, 2H), 7.44 - 7.71 (m, 28H), 7.06 - 7.04 (m, 4H), 6.94 - 6.92 (d, 4H), 2.53 - 2.49 (t, 8H), 1.50 - 1.47 (m, 8H), 1.23 - 1.22 (m, 24H), 0.84 - 0.81 (m, 12H)

[0397] <Low-molecular-weight compounds M1 - M2> Compound M1 was synthesized according to the method described in International Publication No. WO 2019 / 004248. Compound M2 was synthesized according to the method described in International Publication No. WO 2021 / 015177.

[0398]

Chemical Structure

[0399] <Synthesis Example 5: Synthesis of Low-molecular-weight Compound M3>

Chemical Structure

[0400] (Synthesis of Low-molecular-weight Compound M3) After making the inside of the reaction vessel a nitrogen atmosphere, 1.0 g of Compound 1C, 173 mg of phenylboronic acid, 1.1 mg of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.8 mg of tris(dibenzylideneacetone)dipalladium(0), 1.3 mL of a 40% by mass aqueous solution of tetrabutylammonium hydroxide, 4 mL of ion-exchanged water, and 20 mL of toluene were added to the reaction vessel, the temperature was raised to 100 °C, and the mixture was stirred at 100 °C for 4 hours. After cooling the obtained reaction solution to 25 °C, 10 mL of toluene and 10 mL of ion-exchanged water 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. After dissolving the crude product in heptane, it was filtered through silica gel, and the filtrate was dried under reduced pressure at 50 °C. The obtained solid was washed with acetonitrile and dried under reduced pressure at 50 °C to obtain 0.9 g of low molecular weight compound M3. The LC area percentage value of low molecular weight compound M3 was 97.4%.

[0401] LC-MS(APCI positive): m / z = 1474.4 [M] + 1 H-NMR(400 MHz, CD2Cl2) δ(ppm) = 8.62 - 7.00 (m, 36H), 2.43 (t, 8H), 1.49 - 1.41 (m, 8H), 1.23 - 1.18 (m, 24H), 0.82 - 0.78 (t, 12H)

[0402] <Compounds PM1 to PM8> Compound PM2 and Compound PM3 were synthesized according to the method described in JP-A-2011-174062. Compound PM4 and Compound PM5 were synthesized according to the method analogous to that described in WO 02 / 045184. Compound PM6 was synthesized according to the method described in WO 2010 / 013006. Compound PM7 was synthesized according to the method described in JP-A-2012-255117. Compound PM8 was synthesized according to the method described on pages 4323 - 4331 of Journal of Chemistry Vol.70 (2005).

[0403] [Chemical formula]

[0404] [Synthesis Example 6: Synthesis of Compound PM9] [Chemical formula]

[0405] (stage1: Synthesis of Compound PM9A) After making the inside of the reaction vessel under a nitrogen atmosphere, 3,6 - di - tert - butylcarbazole (79.1 g), potassium tert - butoxide (30.3 g) and N - dimethylformamide (700 mL) were added. Thereto, 1,2 - dibromo - 3,4 - difluorobenzene (35.0 g) was added and stirred at 140 °C for 3 hours. The reaction solution was cooled to room temperature, water and toluene were added, and after stirring at room temperature, the aqueous layer was separated. The obtained organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain a crude product. Recrystallization using chloroform and ethanol and recrystallization using toluene and ethanol were performed, and drying under reduced pressure at 50 °C gave Compound PM9A (73.8 g). The LC area percentage value of Compound PM9A was 98.1%.

[0406] (stage2: Synthesis of Compound PM9B) After making the inside of the reaction vessel a nitrogen atmosphere, compound PM9A (73.0 g), 3,6-dichlorocarbazole (32.7 g), and xylene (730 mL) were added. Cuprous iodide (8.79 g) and sodium tert-butoxide (26.6 g) were added thereto, and the mixture was stirred at 130 °C for 21 hours. The reaction solution was cooled to room temperature, water and toluene were added, and after stirring at room temperature, the aqueous layer was separated. The obtained organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene) to obtain compound PM9B (21.6 g). The LC area percentage value of compound PM9B was 95.5%.

[0407] (stage3: Synthesis of compound PM9C) After making the inside of the reaction vessel a nitrogen atmosphere, compound PM9B (18.1 g) and xylene (724 mL) were added, cooled to -40 °C, and 1.6 M n-butyllithium hexane solution (14.6 mL) was added dropwise, followed by stirring for 1 hour. Boron tribromide (9.59 g) was added, the temperature was raised to 0 °C, and after stirring for 1 hour, diisopropylethylamine (9.89 mL) was further added, followed by stirring for 1 hour. The temperature was raised to 130 °C and stirred for 7 hours. After cooling the reaction solution, diisopropylethylamine and 10 mass% aqueous sodium sulfite solution were added and stirred for 30 minutes. Water and toluene were added, and after stirring at room temperature, the aqueous layer was separated. The obtained organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain a crude product. Recrystallization was performed twice using xylene and acetonitrile, and the product was dried under reduced pressure at 50 °C to obtain compound PM9C (9.50 g). The LC area percentage value of compound PM9C was 98.6%.

[0408] (stage4: Synthesis of compound PM9) After making the inside of the reaction vessel an argon gas atmosphere, compound PM9A (8.50 g), bis(pinacolato)diboron (7.40 g), toluene (130 mL), 1,2-dimethoxyethane (170 mL), and potassium acetate (5.72 g) were added and stirred. Tris(dibenzylideneacetone)dipalladium(0) (279 mg) and dicyclohexyl(2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)phosphine (463 mg) were added thereto, and the mixture was stirred at 85 °C for 5 hours. After cooling to room temperature, toluene was added, and filtration was performed through a filter covered with silica gel. The filtrate was concentrated to obtain a crude product. Recrystallization using tetrahydrofuran and acetonitrile and recrystallization using toluene and acetonitrile were performed, and drying under reduced pressure at 50 °C gave compound PM9 (8.74 g). The HPLC area percentage value of compound S2 was 99.6%.

[0409] 1 H-NMR (400 MHz, CDCl3) δ (ppm) = 9.61 (s, 1H), 9.16 (d, 1H), 8.91 (s, 1H), 8.81 (s, 1H), 8.53 (dd, 2H), 8.31 (d, 1H), 8.23 (d, 1H), 8.08 (dd, 1H), 7.94 (d, 2H), 7.67 (d, 2H), 7.22 (m, 2H), 6.61 (d, 1H), 6.25 (dd, 1H), 1.68 (s, 9H), 1.48 (s, 9H), 1.44 (s, 9H), 1.38 (s, 24H), 1.24 (s, 9H)

[0410] <Synthesis Example 7: Synthesis of Compound PM10>

Chemical Structure

[0411] (stage1: Synthesis of Compound PM10A) After making the inside of the reaction vessel a nitrogen atmosphere, 3,5-dibromobenzaldehyde (14.0 g), 2,4-diphenyl-1H-pyrrole (23.2 g) and methylene chloride (560 mL) were added to the reaction vessel and cooled to 0°C. Trifluoroacetic acid (3.7 mL) was added to the resulting reaction solution, and the mixture was stirred at 0°C for 4 hours. An aqueous sodium hydrogen carbonate solution with a concentration of 1 mol / L (726 mL) was added dropwise to the resulting reaction solution. Chloroform was added to the resulting reaction solution, and the aqueous layer was removed. The resulting organic layer was dried over magnesium sulfate and then filtered. The resulting 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 hexane), and then dried under reduced pressure at 50°C to obtain compound PM10A (11.9 g). The LC area percentage value of compound PM10A was 97.7%.

[0412] 1 H-NMR (400 MHz, CDCl3) δ (ppm) = 8.17 (s, 4H), 7.56 - 7.06 (m, 19H), 6.71 (s, 2H), 5.92 (s, 1H)

[0413] (stage2: Synthesis of compound PM10B) After making the inside of the reaction vessel a nitrogen atmosphere, compound PMA10A (150 mg) and methylene chloride (476.4 mL) were added to the reaction vessel and cooled to 0°C. To the resulting reaction solution, 2,3- dichloro-5,6-dicyano-1,4-benzoquinone (4.3 g) was added, and the mixture was stirred at 0°C for 3 hours. An aqueous sodium hydrogen carbonate solution with a concentration of 1 mol / L (237 mL) was added dropwise to the resulting reaction solution. Chloroform was added to the resulting reaction solution, and the aqueous layer was removed. The resulting organic layer was dried over magnesium sulfate and then filtered. The resulting 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 hexane), and then dried under reduced pressure at 50°C to obtain compound PM10B (0.8 g). The LC area percentage value of compound PM10B was 85.8%. The above operation was repeated to ensure the required amount of compound PM10B.

[0414] 1 1H-NMR (400 MHz, CDCl3) δ (ppm) = 7.97 (d, 4H), 7.95 - 7.41 (m, 6H), 7.04 - 6.82 (m, 15H)

[0415] (Stage 3: Synthesis of Compound PM10) After making the inside of the reaction vessel a nitrogen atmosphere, Compound PM10B (1.4 g), triethylamine (1.0 g), boron trifluoride diethyl ether complex (3.9 mL), and toluene (70 mL) were added to the reaction vessel, the temperature was raised to 80°C, and the mixture was stirred at 80°C for 3 hours. Boron trifluoride diethyl ether complex (8 mL) was added to the resulting reaction solution, and the mixture was stirred at 80°C for 4 hours. After cooling the resulting reaction solution to 25°C, a 1 molar aqueous sodium hydrogen carbonate solution (30 mL) was added dropwise. Toluene was added to the resulting reaction solution, and the aqueous layer was removed. The resulting organic layer was dried over magnesium sulfate and then filtered. The resulting 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 hexane), and then concentrated under reduced pressure at 50°C to obtain a crude product. The crude product was recrystallized from ethyl acetate and methanol and dried under reduced pressure at 50°C to obtain Compound PM10 (850 mg). The LC area percentage value of Compound PM10 was 99.9%.

[0416] 1 1H-NMR (400 MHz, CDCl3) δ (ppm) = 7.89 - 7.87 (m, 4H), 7.46 - 7.41 (m, 6H), 7.05 - 7.00 (m, 6H), 6.92 - 6.91 (m, 3H), 6.84 - 6.81 (m, 4H), 6.52 (s, 2H)

[0417] <Example 1> Synthesis of Polymer Compound P1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound 1D (3.093 g), Compound PM1 (0.708 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.81 mg), and toluene (61 mL) were added to the reaction vessel, and the temperature was raised to 80°C. (Step 2) 20 wt% tetraethylammonium hydroxide (61 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (122 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (5.32 mg) were added thereto, and the mixture was refluxed for 3 hours. (Step 4) Thereafter, the temperature of the reaction solution was lowered to 25 °C. After removing the aqueous layer, the solution was washed once with ion-exchanged water, twice with 10 wt% hydrochloric acid, twice with 3 wt% aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. Since precipitation occurred, it was filtered and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was added dropwise to methanol and stirred. Since precipitation occurred, the precipitate was filtered and dried to obtain a polymer compound P1 (2.30 g). The Mn of the polymer compound P1 was 3.6×10 4 and the Mw was 8.7×10 4 .

[0418] The polymer compound P1 is a copolymer composed of a structural unit derived from compound 1D and a structural unit derived from compound PM1 in a molar ratio of 50:50, based on the theoretical value calculated from the amount of the charged raw materials.

[0419] <Example 2> Synthesis of Polymer Compound P2 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound 4D (1.52 g), compound PM3 (0.874 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.85 mg), and toluene (41 mL) were added to the reaction vessel, and the temperature was raised to 80 °C. (Step 2) 20 wt% tetraethylammonium hydroxide (41 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (243 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (2.66 mg) were added thereto, and the mixture was refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C. After removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was dropped into methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a polymer compound P2 (1.68 g). The Mn of the polymer compound P2 was 7.5×10 4 and the Mw was 2.1×10 5 .

[0420] The polymer compound P2 is a copolymer composed of a structural unit derived from compound 4D and a structural unit derived from compound PM3 in a molar ratio of 50:50, based on the theoretical value calculated from the amount of the charged raw materials.

[0421] <Example 3> Synthesis of Polymer Compound P3 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 0.698 g of compound 2D, 0.655 g of compound PM3, 0.60 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, and 22 mL of toluene were added to the reaction vessel, and the temperature was raised to 80 °C. (Step 2) 11 mL of 20% by mass tetraethylammonium hydroxide was dropped into the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, 45.7 mg of phenylboronic acid and 1.93 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto, and the mixture was refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C. After removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was dropped into methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a polymer compound P3 (0.90 g). The Mn of the polymer compound P3 was 5.1×10 4 and the Mw was 1.4×10 5 .

[0422] The polymer compound P3 is a copolymer composed of a structural unit derived from compound 2D and a structural unit derived from compound PM3 in a molar ratio of 50:50, which is the theoretical value calculated from the amount of the charged raw materials.

[0423] <Example 4> Synthesis of Polymer Compound P4 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound 3E (0.535 g), compound PM2 (0.365 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.36 mg), and toluene (15 mL) were added to the reaction vessel and heated to 80 °C. (Step 2) 20% by mass tetraethylammonium hydroxide (15 mL) was dropped into the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (27.4 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.21 mg) were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C, and after removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. As a result, precipitation occurred. Therefore, it was filtered and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been previously passed through with toluene. The purified solution was dropped into methanol and stirred. As a result, precipitation occurred. Therefore, the precipitate was filtered and dried to obtain a polymer compound P4 (0.49 g). The Mn of the polymer compound P4 was 1.1×10 5 and the Mw was 2.4×10 5 .

[0424] The polymer compound P4 is a copolymer composed of a structural unit derived from compound 3E and a structural unit derived from compound PM2 in a molar ratio of 50:50, which is the theoretical value calculated from the amount of the charged raw materials.

[0425] <Example 5> Synthesis of Polymer Compound P5 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 1.23 g of compound 1D, 0.301 g of compound PM1, 0.054 g of compound PM9, 0.72 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, and 26 mL of toluene were added to the reaction vessel, and the temperature was raised to 80 °C. (Step 2) 26 mL of 20% by mass tetraethylammonium hydroxide was dropped into the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, 51.8 mg of phenylboronic acid and 2.30 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C. After removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. As a result, a precipitate was formed, which was then collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was dropped into methanol and stirred. As a result, a precipitate was formed, and the precipitate was collected by filtration and dried to obtain a polymer compound P5 (0.70 g). The Mn of the polymer compound P5 was 2.9×10 4 and the Mw was 6.6×10 4 .

[0426] The polymer compound P5 is a copolymer composed of a structural unit derived from compound 1D, a structural unit derived from compound PM1, and a structural unit derived from compound PM9 in a molar ratio of 47:50:3, based on the theoretical value determined from the amount of the charged raw materials.

[0427] <Example 6> Synthesis of Polymer Compound P6 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 1.52 g of compound 4D, 0.819 g of compound PM3, 0.064 g of compound PM9, 0.85 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, and 41 mL of toluene were added to the reaction vessel and heated to 80 °C. (Step 2) 20 mL of 20% by mass tetraethylammonium hydroxide was added dropwise to the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, 243 mg of phenylboronic acid and 2.66 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C. After removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was added dropwise to methanol and stirred. As a result, a precipitate was formed. The precipitate was collected by filtration and dried to obtain a polymer compound P6 (1.37 g). The Mn of the polymer compound P6 was 7.1×10 4 and the Mw was 1.7×10 5 .

[0428] The polymer compound P6 is a copolymer composed of a structural unit derived from compound 4D, a structural unit derived from compound PM3, and a structural unit derived from compound PM9 in a molar ratio of 50:47:3, which is the theoretical value calculated from the amounts of the charged raw materials.

[0429] <Example 7> Synthesis of Polymer Compound P7 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound 2D (0.785 g), compound PM3 (0.695 g), compound PM9 (0.054 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.72 mg), and toluene (25 mL) were added to the reaction vessel and heated to 80 °C. (Step 2) 25 mL of 20% by mass tetraethylammonium hydroxide was added dropwise to the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (51.8 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (2.42 mg) were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C, and after removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. As a result, precipitation occurred, so it was filtered and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been previously passed through with toluene. The purified solution was dropped into methanol and stirred. As a result, precipitation occurred, so the precipitate was filtered and dried to obtain a polymer compound P7 (0.90 g). The Mn of the polymer compound P7 was 5.3×10 4 and the Mw was 1.3×10 5 .

[0430] The polymer compound P7 is a copolymer composed of a structural unit derived from compound 2D, a structural unit derived from compound PM3, and a structural unit derived from compound PM9 in a molar ratio of 50:47:3, based on the theoretical value determined from the amount of the charged raw materials.

[0431] <Example 8> Synthesis of Polymer Compound P8 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound 3E (0.557 g), compound PM2 (0.406 g), compound PM9 (0.032 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.48 mg), and toluene (16 mL) were added to the reaction vessel, and the temperature was raised to 80 °C. (Step 2) 20% by mass tetraethylammonium hydroxide (16 mL) was dropped into the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (30.5 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.33 mg) were added thereto and refluxed for 3 hours . (Step 4) Subsequently, the reaction solution was cooled to 25°C. After removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. As a precipitate formed, it was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was added dropwise to methanol and stirred. As a precipitate formed, the precipitate was collected by filtration and dried to obtain a polymer compound P8 (0.52 g). The Mn of the polymer compound P8 was 6.2×10 4 and the Mw was 1.3×10 5 .

[0432] The polymer compound P8 is a copolymer composed of structural units derived from compound 3E, structural units derived from compound PM2, and structural units derived from compound PM9 in a molar ratio of 47:50:3, which is the theoretical value calculated from the amount of the charged raw materials.

[0433] <Example 9> Synthesis of Polymer Compound P9 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 1.56 g of compound 1D, 0.333 g of compound PM1, 0.044 g of compound PM10, 29.7 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, 15 mL of toluene, and 15 mL of tetrahydrofuran were added to the reaction vessel and heated to 80°C. (Step 2) 16 mL of a 30% by mass aqueous cesium carbonate solution was added dropwise to the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, 61.0 mg of phenylboronic acid and 4.60 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25°C. After removing the aqueous layer, it was washed three times with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. As a precipitate formed, it was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was added dropwise to methanol and stirred. As a precipitate formed, the precipitate was collected by filtration and dried to obtain 0.77 g of the polymer compound P9. The Mn of the polymer compound P9 was 4.3×10 4 and the Mw was 1.0×10 5 .

[0434] The polymer compound P9 is a copolymer composed of structural units derived from compound 1D, structural units derived from compound PM1, and structural units derived from compound PM10 in a molar ratio of 50:47:3, based on the theoretical value calculated from the amount of the charged raw materials.

[0435] <Example 10> Synthesis of Polymer Compound P10 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 1.48 g of compound 3E, 0.957 g of compound PM2, 0.055 g of compound PM10, 37.2 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, 20 mL of toluene, and 20 mL of tetrahydrofuran were added to the reaction vessel and heated to 80°C. (Step 2) 20 mL of a 30% by mass aqueous cesium carbonate solution was added dropwise to the reaction solution and refluxed for 5 hours. (Step 3) After the reaction, 76.2 mg of phenylboronic acid and 17.5 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto and refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25°C. After removing the aqueous layer, it was washed three times with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. As a precipitate formed, it was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was added dropwise to methanol When stirred, precipitation occurred. The precipitate was filtered off and dried to obtain 1.01 g of polymer compound P10. The Mn of polymer compound P10 was 1.1×10 5 and the Mw was 1.8×10 5 .

[0436] Polymer compound P10 is a copolymer composed of a structural unit derived from compound 3E, a structural unit derived from compound PM2, and a structural unit derived from compound PM10 in a molar ratio of 50:47:3, based on the theoretical value calculated from the amounts of the charged raw materials.

[0437] <Comparative Example 1> Synthesis of Polymer Compound P11 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, 0.655 g of compound PM3, 0.587 g of compound PM7, 0.60 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium, and 19 mL of toluene were added to the reaction vessel, and the temperature was raised to 80°C. (Step 2) 19 mL of 20% by mass tetraethylammonium hydroxide was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, 45.7 mg of phenylboronic acid and 1.93 mg of dichlorobis(tris-o-methoxyphenylphosphine)palladium were added thereto, and the mixture was refluxed for 3 hours. (Step 4) Thereafter, the temperature of the reaction solution was lowered to 25°C. After removing the aqueous layer, the organic layer was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred. Since precipitation occurred, the precipitate was filtered off and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column through which toluene had been previously passed. The purified solution was added dropwise to methanol and stirred. Since precipitation occurred, the precipitate was filtered off and dried to obtain 0.76 g of polymer compound P11. The Mn of polymer compound P11 was 1.2×10 5 and the Mw was 3.8×10 5 .

[0438] The polymer compound P11 is a copolymer composed of a structural unit derived from compound PM3 and a structural unit derived from compound PM7 in a molar ratio of 50:50 based on the theoretical value determined from the amounts of the charged raw materials.

[0439] <Comparative Example 2> Synthesis of Polymer Compound P12 The polymer compound P12 was synthesized by the method described in JP-A-2011-181900 using compound PM4, compound PM5, and compound PM8. The polymer compound P12 is the same polymer compound as polymer compound 4 described in JP-A-2011-181900.

[0440] The polymer compound P12 is a copolymer composed of the total of the structural units derived from compound PM4 and the structural units derived from compound PM5 and the structural units derived from compound PM8 in a molar ratio of 95:5 based on the theoretical value determined from the amounts of the charged raw materials.

[0441] <Comparative Example 3> Synthesis of Polymer Compound P13 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound PM3 (0.873 g), compound PM6 (0.675 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.85 mg), and toluene (24 mL) were added to the reaction vessel, and the temperature was raised to 80°C. (Step 2) 20% by mass tetraethylammonium hydroxide (12 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (61.0 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (2.66 mg) were added thereto, and the mixture was refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25 °C, and after removing the aqueous layer, it was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with ion-exchanged water. The obtained organic layer was dropped into methanol and stirred. Since precipitation occurred, it was filtered and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing it through an alumina column that had been pre-passed with toluene. The purified solution was dropped into methanol and stirred. Since precipitation occurred, the precipitate was filtered and dried to obtain a polymer compound P13 (0.80 g). The Mn of the polymer compound P13 was 3.5×10 4 and the Mw was 8.5×10 4 .

[0442] The polymer compound P13 is a copolymer composed of a structural unit derived from the compound PM3 and a structural unit derived from the compound PM6 in a molar ratio of 50:50, which is the theoretical value calculated from the amount of the charged raw materials.

[0443] <Example Measurement Example 1> Evaluation of Luminance Lifetime The polymer compound P1 was dissolved in toluene to a concentration of 2.4% by mass to obtain an ink.

[0444] The toluene solution obtained above was applied onto a synthetic quartz glass substrate by spin coating so that the thickness after drying was 100 nm, and an organic compound layer was formed by heating at 150 °C for 10 minutes in a nitrogen atmosphere (oxygen mass concentration 10 ppm or less, water mass concentration 10 ppm or less).

[0445] The substrate having the organic compound layer formed thereon was placed in a vapor deposition machine and depressurized to 1.0×10 -4 Pa or less, and then about 30 nm of sodium fluoride was vapor-deposited. After vapor deposition, a measurement sample 1 was prepared by sealing with a glass substrate in a nitrogen atmosphere (oxygen mass concentration 10 ppm or less, water mass concentration 10 ppm or less).

[0446] The excitation light intensity of the excitation light source for Measurement Sample 1 was determined by the method described above using Equation (III). The emission luminance obtained when Measurement Sample 1 was irradiated with excitation light was 1398 cd / m 2 . While keeping the excitation light intensity constant, Measurement Sample 1 was continuously made to emit light, and the time until the emission luminance became 60% of the emission luminance at the start of measurement (hereinafter referred to as "LT60") was measured. The results are shown in Table 2.

[0447] When the color conversion efficiency of Measurement Sample 1 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 40%.

[0448] <Measurement Example 2> Evaluation of Luminance Lifetime A measurement sample 2 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that a polymer compound P2 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0449] When the emission luminance of Measurement Sample 2 was measured at an excitation light intensity at which the photon absorption amount was constant with Measurement Sample 1, it was 2533 cd / m 2 . Thereafter, while keeping the excitation light intensity constant, Measurement Sample 2 was continuously made to emit light, and "LT60" was measured. The results are shown in Table 2.

[0450] When the color conversion efficiency of Measurement Sample 2 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 73%. <Measurement Example 3> Evaluation of Luminance Lifetime A measurement sample 3 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that a polymer compound P3 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0451] When the emission luminance of Measurement Sample 3 was measured at an excitation light intensity at which the photon absorption amount was constant with Measurement Sample 1, it was 1639 cd / m 2 . Thereafter, while keeping the excitation light intensity constant, Measurement Sample 3 was continuously made to emit light, and "LT60" was measured. The results are shown in Table 2.

[0452] When measuring the color conversion efficiency of measurement sample 3 at an excitation wavelength of 460 nm, the color conversion efficiency was 41%.

[0453] <Example of actual measurement 4> Evaluation of luminance lifetime A measurement sample 4 was prepared and the luminance lifetime was evaluated in the same manner as in Example of actual measurement 1, except that a polymer compound P4 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0454] When measuring the emission luminance of measurement sample 4 at an excitation light intensity at which the photon absorption amount is constant with measurement sample 1, it was 2852 cd / m 2 Then, measurement sample 4 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0455] When measuring the color conversion efficiency of measurement sample 4 at an excitation wavelength of 460 nm, the color conversion efficiency was 58%.

[0456] <Example of actual measurement 5> Evaluation of luminance lifetime A measurement sample 5 was prepared and the luminance lifetime was evaluated in the same manner as in Example of actual measurement 1, except that a polymer compound P5 was dissolved in xylene to a concentration of 2.4% by mass to prepare an ink.

[0457] When measuring the emission luminance of measurement sample 5 at an excitation light intensity at which the photon absorption amount is constant with measurement sample 1, it was 4370 cd / m 2 Then, measurement sample 5 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0458] When measuring the color conversion efficiency of measurement sample 5 at an excitation wavelength of 460 nm, the color conversion efficiency was 77%.

[0459] <Example of actual measurement 6> Evaluation of luminance lifetime A measurement sample 6 was prepared and the luminance lifetime was evaluated in the same manner as in Example of actual measurement 1, except that a polymer compound P6 was dissolved in xylene to a concentration of 1.2% by mass to prepare an ink.

[0460] When the emission luminance of measurement sample 6 was measured with an excitation light intensity at which the photon absorption amount of measurement sample 1 was constant, it was 7675 cd / m 2 After that, measurement sample 6 was continuously made to emit light while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0461] When the color conversion efficiency of measurement sample 6 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 87%.

[0462] <Measurement Example 7> Evaluation of Luminance Lifetime A measurement sample 7 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the polymer compound P7 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0463] When the emission luminance of measurement sample 7 was measured with an excitation light intensity at which the photon absorption amount of measurement sample 1 was constant, it was 4597 cd / m 2 After that, measurement sample 7 was continuously made to emit light while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0464] When the color conversion efficiency of measurement sample 7 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 75% was.

[0465] <Measurement Example 8> Evaluation of Luminance Lifetime A measurement sample 8 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the polymer compound P8 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0466] When the emission luminance of measurement sample 8 was measured with an excitation light intensity at which the photon absorption amount of measurement sample 1 was constant, it was 5692 cd / m 2 After that, measurement sample 8 was continuously made to emit light while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0467] When the color conversion efficiency of measurement sample 8 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 83%.

[0468] <Example of Actual Measurement 9> Evaluation of Luminance Lifetime A measurement sample 9 was prepared and the luminance lifetime was evaluated in the same manner as in Example of Actual Measurement 1, except that a polymer compound P9 was dissolved in xylene to a concentration of 2.4% by mass to prepare an ink.

[0469] When the emission luminance of measurement sample 9 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 604 cd / m 2 Thereafter, measurement sample 9 was continuously made to emit light while keeping the excitation light intensity constant, and “LT60” was measured. The results are shown in Table 2.

[0470] When the color conversion efficiency of measurement sample 9 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 45%.

[0471] <Example of Actual Measurement 10> Evaluation of Luminance Lifetime A measurement sample 10 was prepared and the luminance lifetime was evaluated in the same manner as in Example of Actual Measurement 1, except that a polymer compound P10 was dissolved in xylene to a concentration of 2% by mass to prepare an ink.

[0472] When the emission luminance of measurement sample 10 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 678 cd / m 2 Thereafter, measurement sample 10 was continuously made to emit light while keeping the excitation light intensity constant, and “LT60” was measured. The results are shown in Table 2.

[0473] When the color conversion efficiency of measurement sample 10 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 66%.

[0474] <Example of Actual Measurement 11> Measurement of Luminance Lifetime A 2.4 mass% xylene solution prepared by adding 3% of low molecular weight compound M1 to high molecular weight compound P1 was prepared by the following method. First, a xylene solution in which high molecular weight compound P1 was dissolved at a concentration of 2.4 mass% was prepared. Separately, a xylene solution in which low molecular weight compound M1 was dissolved at a concentration of 2.4 mass% was prepared. These solutions were mixed so that the mass ratio of the solution of high molecular weight compound P1 to the solution of low molecular weight compound M1 was 97:3 to obtain the solution.

[0475] A measurement sample 11 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0476] When the emission luminance of measurement sample 11 was measured with the same excitation light intensity at which the photon absorption amount was constant as that of measurement sample 1, it was 2900 cd / m 2 Then, measurement sample 11 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0477] When the color conversion efficiency of measurement sample 11 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 61%. It was.

[0478] <Measurement Example 12> Measurement of Luminance Lifetime A 2 mass% xylene solution prepared by adding 3% of low molecular weight compound M1 to high molecular weight compound P2 was prepared in the same manner as in Measurement Example 11.

[0479] A measurement sample 12 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0480] When the emission luminance of measurement sample 12 was measured with the same excitation light intensity at which the photon absorption amount was constant as that of measurement sample 1, it was 3554 cd / m 2 Then, measurement sample 12 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0481] When the color conversion efficiency of measurement sample 12 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 72%.

[0482] <Example of Measurement 13> Measurement of Luminance Lifetime A 2.4 mass% xylene solution prepared by adding 3% of the low molecular weight compound M1 to the polymer compound P3 was prepared in the same manner as in Example of Measurement 11.

[0483] A measurement sample 13 was prepared and the luminance lifetime was evaluated in the same manner as in Example of Measurement 1, except that the xylene solution obtained above was used.

[0484] When the emission luminance of the measurement sample 13 was measured at an excitation light intensity at which the photon absorption amount was constant with the measurement sample 1, it was 3033 cd / m 2 It was. Thereafter, the measurement sample 13 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0485] When the color conversion efficiency of the measurement sample 13 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 53%.

[0486] <Example of Measurement 14> Measurement of Luminance Lifetime A 2 mass% xylene solution prepared by adding 3% of the low molecular weight compound M1 to the polymer compound P4 was prepared in the same manner as in Example of Measurement 11.

[0487] A measurement sample 14 was prepared and the luminance lifetime was evaluated in the same manner as in Example of Measurement 1, except that the xylene solution obtained above was used.

[0488] When the emission luminance of the measurement sample 14 was measured at an excitation light intensity at which the photon absorption amount was constant with the measurement sample 1, it was 4021 cd / m 2 It was. Thereafter, the measurement sample 14 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0489] When the color conversion efficiency of the measurement sample 14 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 69%.

[0490] <Example of Measurement 15> Measurement of Luminance Lifetime A 2.4 mass% xylene solution prepared by adding 3% of the low molecular weight compound M2 to the high molecular weight compound P1 was prepared in the same manner as in Measurement Example 11.

[0491] A measurement sample 15 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0492] When the emission luminance of measurement sample 15 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 503 cd / m 2 After that, measurement sample 15 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0493] When the color conversion efficiency of measurement sample 15 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 56%.

[0494] <Measurement Example 16> Measurement of Luminance Lifetime A 2 mass% xylene solution prepared by adding 3% of the low molecular weight compound M2 to the high molecular weight compound P2 was prepared in the same manner as in Measurement Example 11.

[0495] A measurement sample 16 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0496] When the emission luminance of measurement sample 16 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 417 cd / m 2 After that, measurement sample 16 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0497] When the color conversion efficiency of measurement sample 16 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 74%.

[0498] <Measurement Example 17> Measurement of Luminance Lifetime A 2.4 mass% xylene solution prepared by adding 3% of the low molecular weight compound M2 to the high molecular weight compound P3 was prepared in the same manner as in Measurement Example 11.

[0499] A measurement sample 17 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0500] When the emission luminance of measurement sample 17 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 409 cd / m 2 After that, measurement sample 17 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0501] When the color conversion efficiency of measurement sample 17 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 55%.

[0502] <Measurement Example 18> Measurement of Luminance Lifetime A 2% by mass xylene solution in which 3% of low molecular compound M2 was added to polymer compound P4 was prepared in the same manner as in Measurement Example 11.

[0503] A measurement sample 18 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0504] When the emission luminance of measurement sample 18 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 616 cd / m 2 After that, measurement sample 18 was continuously emitted while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0505] When the color conversion efficiency of measurement sample 18 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 62%.

[0506] <Measurement Example 19> Evaluation of Luminance Lifetime A measurement sample 19 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that an ink was prepared by dissolving low molecular compound M3 in xylene at a concentration of 3.7% by mass.

[0507] When the emission luminance of the measurement sample 19 is measured at the excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 699 cd / m 2 After that, the measurement sample 19 was allowed to emit light continuously while keeping the excitation light intensity constant, and the "LT60" was measured. The results are shown in Table 2.

[0508] When the color conversion efficiency of the measurement sample 19 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 23%.

[0509] <Measurement Example 20> Luminance Life Measurement A 3.5% by mass xylene solution in which 3% of the low molecular weight compound M1 was added to the low molecular weight compound M3 was prepared in the same manner as in Example 11 of Measurement.

[0510] A measurement sample 20 was prepared in the same manner as in Example Measurement 1, except that the xylene solution obtained above was used, and the luminance lifetime was evaluated.

[0511] When the emission luminance of the measurement sample 20 is measured at the excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 2367 cd / m 2 Thereafter, the measurement sample 20 was allowed to emit light continuously while keeping the excitation light intensity constant, and the "LT60" was measured. The results are shown in Table 2.

[0512] When the color conversion efficiency of the measurement sample 20 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 67%.

[0513] <Measurement Example 21> Luminance Life Measurement A 3% by mass xylene solution in which the low molecular weight compound M3 was added with 3% of the low molecular weight compound M2 was prepared in the same manner as in Example 11 of Measurement.

[0514] A measurement sample 21 was prepared in the same manner as in Example Measurement 1, except that the xylene solution obtained above was used, and the luminance lifetime was evaluated.

[0515] When the emission luminance of the measurement sample 21 is measured at the excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 343 cd / m 2 Subsequently, while keeping the excitation light intensity constant, the measurement sample 21 was continuously caused to emit light, and "LT60" was measured. The results are shown in Table 2.

[0516] When the color conversion efficiency of the measurement sample 21 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 63%.

[0517] <Comparative Measurement Example 1> Evaluation of Luminance Lifetime A measurement sample 22 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the polymer compound P11 was dissolved in xylene to a concentration of 1.6% by mass to prepare an ink.

[0518] When the emission luminance of the measurement sample 22 was measured at an excitation light intensity at which the photon absorption amount was constant with the measurement sample 1, it was 1758 cd / m 2 Subsequently, while keeping the excitation light intensity constant, the measurement sample 22 was continuously caused to emit light, and "LT60" was measured. The results are shown in Table 2.

[0519] When the color conversion efficiency of the measurement sample 22 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 65%.

[0520] <Comparative Measurement Example 2> Evaluation of Luminance Lifetime A measurement sample 23 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the polymer compound P12 was dissolved in xylene to a concentration of 2.4% by mass to prepare an ink.

[0521] An attempt was made to measure the emission luminance of the measurement sample 23 at an excitation light intensity at which the photon absorption amount was constant with the measurement sample 1, but no emission was observed and "LT60" could not be measured.

[0522] When the color conversion efficiency of the measurement sample 23 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 30%.

[0523] <Comparative Measurement Example 3> Evaluation of Luminance Lifetime A measurement sample 24 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the polymer compound P13 was dissolved in xylene to a concentration of 2.4% by mass to prepare an ink.

[0524] When the emission luminance of the measurement sample 24 was measured at an excitation light intensity at which the photon absorption amount was constant with that of the measurement sample 1, it was 2425 cd / m 2 Thereafter, the measurement sample 24 was continuously caused to emit light while maintaining the excitation light intensity constant, and “LT60” was measured. The results are shown in Table 2.

[0525] When the color conversion efficiency of the measurement sample 24 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 60%.

[0526] <Comparative Measurement Example 4> Measurement of Luminance Lifetime A 2.4% by mass xylene solution in which 3% of the low molecular compound M1 was added to the polymer compound P13 was prepared in the same manner as in Measurement Example 11.

[0527] A measurement sample 25 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the above-obtained xylene solution was used.

[0528] When the emission luminance of the measurement sample 25 was measured at an excitation light intensity at which the photon absorption amount was constant with that of the measurement sample 1, it was 3176 cd / m 2 Thereafter, the measurement sample 25 was continuously caused to emit light while maintaining the excitation light intensity constant, and “LT60” was measured. The results are shown in Table 2.

[0529] When the color conversion efficiency of the measurement sample 25 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 53%.

[0530] <Comparative Measurement Example 5> Measurement of Luminance Lifetime A 2.4% by mass xylene solution in which 3% of the low molecular compound M2 was added to the polymer compound P13 was prepared in the same manner as in Measurement Example 11.

[0531] A measurement sample 26 was prepared and the luminance lifetime was evaluated in the same manner as in Measurement Example 1, except that the xylene solution obtained above was used.

[0532] When the emission luminance of measurement sample 26 was measured at an excitation light intensity at which the photon absorption amount was constant with measurement sample 1, it was 639 cd / m 2 After that, measurement sample 26 was continuously made to emit light while keeping the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0533] When the color conversion efficiency of measurement sample 26 was measured at an excitation wavelength of 460 nm, the color conversion efficiency was 58% It was.

[0534]

Table 2

[0535] From these results, it can be seen that the color conversion material containing the compound (A) having a condensed aromatic hydrocarbon skeleton in which 6 or more rings are condensed has a longer luminance lifetime than any of the color conversion materials containing a condensed heterocyclic compound in which less than 6 rings are condensed, a condensed heterocyclic compound in which 6 or more rings are condensed, and a compound having a condensed aromatic hydrocarbon skeleton in which less than 6 rings are condensed.

Industrial Applicability

[0536] According to the embodiment of the present disclosure, a color conversion material excellent in luminance lifetime can be provided. Therefore, by applying such a color conversion material to a light-emitting device, it is possible to improve the stability of light emission. Further, such a light-emitting device is suitable for a display device. < / nmr>

Claims

1. A color conversion material that converts incident light into light having a longer wavelength than the incident light, the color conversion material comprising a compound (A) having a condensed aromatic hydrocarbon skeleton in which six or more rings are condensed.

2. The color conversion material according to claim 1, wherein the condensed aromatic hydrocarbon skeleton is a skeleton in which 6 to 8 rings are condensed.

3. The color conversion material according to claim 1, wherein the condensed aromatic hydrocarbon skeleton is a skeleton in which only six-membered rings are condensed.

4. The color conversion material according to claim 1, wherein the condensed aromatic hydrocarbon skeleton has a structure represented by formula (1) or formula (2). 【Chemical 1】

5. The color conversion material according to claim 1, wherein the compound (A) is a polymer compound (A) containing a structural unit (A) having the condensed aromatic hydrocarbon skeleton.

6. The color conversion material according to claim 5, wherein the structural unit (A) is a structural unit obtained by removing one or more hydrogen atoms from a condensed aromatic hydrocarbon represented by any one of formulas (3) to (6). 【Chemical 2】 [In the formula, the hydrogen atom directly bonded to the carbon atom constituting the condensed ring may be substituted with a substituent.]

7. The color conversion material according to claim 5, comprising one or more compounds (B) selected from the group consisting of the following low molecular compound (B), the following polymer compound (AB), and the following polymer compound (B), and satisfying condition III. Low molecular compound (B): The low molecular compound (B) is a low molecular compound that satisfies the following condition I. Polymer compound (AB): The polymer compound (AB) is a polymer compound containing the structural unit (A) and a structural unit (B) that satisfies the following condition II, and also corresponds to the polymer compound (A). Polymer compound (B): The polymer compound (B) is a polymer compound (B) containing a structural unit (B) that satisfies the following condition II (however, excluding those corresponding to the polymer compound (A)). (Condition I) The energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (A)> The energy level of the lowest singlet excited state of the low molecular compound (B) (Condition II) The energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (A)> The energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the structural unit (B) (Condition III) The molar content of the constitutional unit (A) per unit mass > [the molar content of the constitutional unit (B) per unit mass + the molar content of the low-molecular compound (B) per unit mass]

8. The constitutional unit (B) is a constitutional unit derived from an organic boron compound, The color conversion material according to claim 7, wherein the low-molecular compound (B) is an organic boron compound.

9. The color conversion material according to claim 8, wherein the organic boron compound is a low-molecular compound represented by any one of formulas (7) to (9). 【Chemical Formula 3】 [In the formula, Ring A, Ring B, and Ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have substituents. X represents a boron atom, a phosphorus atom, P=O, P=S, an aluminum atom, a gallium atom, an arsenic atom, Si-Rx, or Ge-Rx. Rx represents an aryl group or an alkyl group. These groups may have substituents. Y １ represents N—Ry, a sulfur atom or a selenium atom. Y ２ and Y ３ each independently represents an oxygen atom, N—Ry, a sulfur atom or a selenium atom. Ry represents a hydrogen atom, an aryl group, a monovalent heterocyclic group, or an alkyl group. These groups may have substituents. When there are a plurality of Rys, they may be the same or different. Ry may be bonded to Ring A, Ring B, or Ring C directly or via a linking group. X represents C-R ７ or N. R １ to R ９ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, or a phosphine oxide group. These groups may have substituents. R １ to R ９ The adjacent groups of may be bonded directly or via a linking group to form a ring.]

10. The color conversion material according to claim 1, wherein the compound (A) is a low-molecular compound (A) having the condensed aromatic hydrocarbon skeleton.

11. The color conversion material according to claim 10, comprising at least one compound (B) selected from the group consisting of the following low-molecular compound (B) and the following high-molecular compound (B) and satisfying Condition III. Low-molecular compound (B): The low-molecular compound (B) is a low-molecular compound satisfying the following Condition I. High-molecular compound (B): The high-molecular compound (B) is a high-molecular compound containing a constitutional unit (B) satisfying the following Condition II. (Condition I) The energy level of the lowest singlet excited state of the low-molecular compound (A) > the energy level of the lowest singlet excited state of the low-molecular compound (B) (Condition II) The energy level of the lowest singlet excited state of the low-molecular compound (A) > the energy level of the lowest singlet excited state of the compound in which a hydrogen atom is bonded to the bond of the constitutional unit (B) (Condition III) The molar content of the low-molecular compound (A) per unit mass > [the molar content of the constitutional unit (B) per unit mass + the molar content of the low-molecular compound (B) per unit mass]

12. The constitutional unit (B) is a constitutional unit derived from an organic boron compound, The color conversion material according to claim 11, wherein the low molecular compound (B) is an organic boron compound.

13. The color conversion material according to claim 12, wherein the organic boron compound is a low molecular compound represented by any one of formulas (7) to (9). 【Chemical Formula 4】 [In the formula, Ring A, Ring B, and Ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have substituents. X represents a boron atom, a phosphorus atom, P=O, P=S, an aluminum atom, a gallium atom, an arsenic atom, Si-Rx, or Ge-Rx. Rx represents an aryl group or an alkyl group. These groups may have substituents. Y １ represents N—Ry, a sulfur atom or a selenium atom. Y ２ and Y ３ each independently represents an oxygen atom, N—Ry, a sulfur atom or a selenium atom. Ry represents a hydrogen atom, an aryl group, a monovalent heterocyclic group, or an alkyl group. These groups may have substituents. When a plurality of Rys are present, they may be the same or different. Ry may be bonded to the Ring A, the Ring B, or the Ring C directly or via a linking group. X represents C-R ７ or N R １ to R ９ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, or a phosphine oxide group. These groups may have substituents. R １ to R ９ The adjacent groups of may be bonded directly or via a linking group to form a ring. ]

14. An ink containing the color conversion material according to any one of claims 1 to 13 and a solvent.

15. A color conversion film that converts incident light into light having a longer wavelength than the incident light, the color conversion film containing the color conversion material according to any one of claims 1 to 13.

16. A light-emitting device containing the color conversion material according to any one of claims 1 to 13.

17. A display device containing the color conversion material according to any one of claims 1 to 13.

Images