Color conversion material, and ink, color conversion film, light-emitting device, and display device each including same

Abstract

Provided is a color conversion material having an excellent luminance life.　The color conversion material converts incident light into light having a longer wavelength than the incident light. The color conversion material includes a compound (A) having a fused aromatic hydrocarbon skeleton in which six or more rings have been fused together.

Description

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

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

[0002] One technique for multicoloring light from a light source is the color conversion method. The color conversion method is a method for multicoloring light by attaching a color conversion film containing a color conversion material that absorbs incident light and emits light with 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, green, and blue light can be obtained from the blue light source, and white light can also be obtained from these three primary colors. Therefore, color conversion materials can be applied to liquid crystal display devices, electroluminescence (EL) display devices, lighting devices, etc.

[0003] Known color conversion materials include inorganic fluorescent particles made of quantum dots, but color conversion materials using quantum dots are vulnerable to heat, water, and oxygen, making them difficult to handle and causing problems in the process, such as poor workability. Therefore, in recent years, techniques have been proposed that use organic materials as color conversion materials.

[0004] For example, Patent Document 1 discloses a color-changing material composition containing a fluorescent dye consisting of a heteropolycyclic compound such as a phenylnaphthoxazole derivative and a benzofurano-1,2-naphthoquinone derivative, and a binder material. According to Patent Document 1, a color-changing film made from this color-changing material composition does not deteriorate in color-changing performance even when used for a long period of time, and does not suffer from the problem of the dye precipitating during storage, making the film unusable.

[0005] Japanese Patent Application Laid-Open No. 2004-263179

[0006] However, color-changing films manufactured using conventional organic color-changing materials have a problem in that their luminance decreases significantly over time, and their 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-changing material having an excellent luminance life.

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

[0008] [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 fused aromatic hydrocarbon skeleton with six or more rings fused together. [2] The color conversion material according to [1], wherein the fused aromatic hydrocarbon skeleton is a skeleton with six to eight rings fused together. [3] The color conversion material according to [1] or [2], wherein the fused aromatic hydrocarbon skeleton is a skeleton with only six-membered rings fused together. [4] The color conversion material according to any one of [1] to [3], wherein the fused aromatic hydrocarbon skeleton has a structure represented by formula (1) or formula (2). [5] The color-converting material according to any one of [1] to [4], wherein the compound (A) is a polymer compound (A) containing a structural unit (A) having a condensed aromatic hydrocarbon skeleton. [6] The color-converting material according to [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). [In the formula, a hydrogen atom directly bonded to a carbon atom constituting the fused ring may be substituted with a substituent.] [7] The color conversion material according to [5] or [6], comprising one or more compounds (B) selected from the group consisting of the following low molecular weight compound (B), the following polymer compound (AB), and the following polymer compound (B), and satisfying condition III. Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound satisfying condition I below. Polymer compound (AB): The polymer compound (AB) is a polymer compound comprising the structural unit (A) and a structural unit (B) satisfying condition II below, and also corresponds to the polymer compound (A). Polymer compound (B): The polymer compound (B) is a polymer compound (B) comprising a structural unit (B) satisfying condition II below (excluding those corresponding to the polymer compound (A)). (Condition I) The energy level of the lowest singlet excited state of a compound having a hydrogen atom bonded to a bond of the structural unit (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 a compound having a hydrogen atom bonded to a bond of the structural unit (A) > the energy level of the lowest singlet excited state of a compound having a hydrogen atom bonded to a bond of the structural unit (B). (Condition III) 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 weight compound (B) per unit mass]. [8] The color conversion material according to [7], wherein the structural unit (B) is a structural unit derived from an organoboron compound, and the low molecular weight compound (B) is an organoboron compound. [9] The color conversion material according to [8], wherein the organoboron compound is a low molecular weight compound represented by any one of formulas (7) to (9). [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 a substituent. 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 a substituent. Y １ represents N-Ry, a sulfur atom, or a selenium atom. ２and 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 a substituent. When a plurality of Ry's are present, they may be the same or different. Ry's may be bonded to the A ring, the B ring, or the C ring directly or via a linking group. X represents C-R ７ or N. １ ~R ９ R each independently represent 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 a substituent. １ ~R ９Adjacent groups may be bonded to each other directly or via a linking group to form a ring.]

[10] The color conversion material according to any one of [1] to [4], wherein the compound (A) is a low molecular weight compound (A) having a condensed aromatic hydrocarbon skeleton.

[11] The color conversion material according to

[10] , which contains one or more compounds (B) selected from the group consisting of the following low molecular weight compounds (B) and the following polymer compounds (B), and satisfies condition III. Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound that satisfies the following condition I. Polymer compound (B): The polymer compound (B) is a polymer compound containing a structural unit (B) that satisfies 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 a compound obtained by bonding a hydrogen atom to a 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].

[12] The color conversion material according to

[11] , wherein the structural unit (B) is a structural unit derived from an organoboron compound, and the low molecular weight compound (B) is an organoboron compound.

[13] The color conversion material according to

[12] , wherein the organoboron compound is a low molecular weight compound represented by any one of formulas (7) to (9). [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 a substituent. 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 a substituent. Y １ represents N-Ry, a sulfur atom, or a selenium atom. ２ and Y ３each 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 a substituent. When a plurality of Ry's are present, they may be the same or different. Ry's may be bonded to the A ring, the B ring, or the C ring directly or via a linking group. X represents C-R ７ or N. １ ~R ９ R each independently represent 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 a substituent. １ ~R ９ Adjacent groups may be bonded to each other directly or via a linking group to form a ring.]

[14] An ink comprising 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 with a longer wavelength than the incident light, the color conversion film comprising the color conversion material according to any one of [1] to

[13] .

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

[13] .

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

[13] .

[0009] According to the present disclosure, it is possible to provide a color conversion material that is excellent in luminance life.

[0010] The following describes in detail embodiments of the present disclosure. The following description is an example (typical example) of an embodiment of the present disclosure, and the present disclosure is not limited to the contents thereof as long as it does not depart from the gist of the present disclosure.

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

[0012] Me is a methyl group, Et is an ethyl group, i-Pr is an isopropyl group, Bu and n-Bu are normal butyl groups, t-Bu is a tert-butyl group, C ６ H １３ and nC ６ H １３ is a normal hexyl group, C ８ H １７ and nC ８ H １７ represents a normal octyl group.

[0013] The hydrogen atom may be a deuterium atom or a proton atom.

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

[0015] The term "polymer compound" refers to a compound having a molecular weight distribution and a polystyrene-equivalent number average molecular weight (Mn) of 1×10 ３ ~1 x 10 ８ The polymer is defined as:

[0016] A "low molecular weight compound" is a compound that does not have a molecular weight distribution and has a molecular weight of 1×10 ４ The following compounds are meant:

[0017] The term "structural unit" refers to a unit that exists in a polymer compound in one or more instances. A structural unit that exists in a polymer compound in two or more instances is generally also called a "repeating unit."

[0018] The "alkyl group" may be either linear or branched, and may have a substituent. The number of carbon atoms in a linear alkyl group, not including the number of carbon atoms in the substituent, is usually 1 to 50, preferably 2 to 30, more preferably 3 to 20, and even more preferably 4 to 8. The number of carbon atoms in a branched alkyl group, not including the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.

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

[0020] The "cycloalkyl group" may have a substituent. The number of carbon atoms in the cycloalkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms in the substituent.

[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, not including 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 is usually 3 to 20, and preferably 6 to 10, not including the number of carbon atoms in the substituent.

[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-cyclopropylenediyl group, and a 1,3-adamantanediyl group.

[0026] An "aromatic hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon is also called an "aryl group." A group obtained by removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon is also called an "arylene group."

[0027] The number of carbon atoms in the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, and even more preferably 6 to 18, not including the number of carbon atoms in the substituents.

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

[0029] The term "aryl group" refers to the atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The aryl group may have a substituent. The number of carbon atoms in the aryl group, not including the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, even more preferably 6 to 20, and particularly preferably 6 to 10.

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

[0031] The term "arylene group" refers to the atomic group remaining after 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, not including the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.

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

[0033]

[0034]

[0035]

[0036]

[0037] [Wherein R and R ａ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. ａ may be the same or different, R ａ may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0038] The "alkoxy group" may be either straight-chain or branched, and may have a substituent. The number of carbon atoms in a straight-chain alkoxy group, not including the number of carbon atoms in the substituent, is usually 1 to 40, preferably 1 to 20, and more preferably 4 to 10. The number of carbon atoms in a branched alkoxy group, not including the number of carbon atoms in the substituent, is usually 3 to 40, preferably 4 to 20, and 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 have been substituted with substituents such as a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a fluorine atom.

[0040] The "cycloalkoxy group" may have a substituent. The number of carbon atoms in the cycloalkoxy group is usually 3 to 40, preferably 4 to 10, not including the carbon atoms in the substituent.

[0041] An example of the cycloalkoxy group is a cyclohexyloxy group.

[0042] The "aryloxy group" may have a substituent. The number of carbon atoms in the aryloxy group is usually 6 to 60, preferably 6 to 48, and more preferably 6 to 40, not including the number of carbon atoms in the substituent.

[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 have been substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a fluorine atom.

[0044] The "arylthio group" may have a substituent. The number of carbon atoms in the arylthio group is usually 6 to 60, preferably 6 to 48, and more preferably 6 to 40, not including the number of carbon atoms in the substituent.

[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 have been substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a fluorine atom.

[0046] A "p-valent heterocyclic group" (p represents an integer of 1 or more) refers to the atomic group remaining after removing p hydrogen atoms from a heterocyclic compound among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms that constitute the ring. Among p-valent heterocyclic groups, a "p-valent aromatic heterocyclic group" is preferred, which is the atomic group remaining after removing p hydrogen atoms from an aromatic heterocyclic compound among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms that constitute the ring. A monovalent aromatic heterocyclic group is also called a "heteroaryl group". The p-valent heterocyclic group may have a substituent.

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

[0048] The number of carbon atoms in the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the number of carbon atoms in the substituent.

[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 isoquinolinyl group, a benzophenone ... Examples of the naphthyridinyl group include 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 have been substituted with substituents such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, etc. 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 divalent heterocyclic group has usually 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 4 to 15 carbon atoms, not including the carbon atoms of the substituents.

[0051] Examples of divalent heterocyclic groups include divalent groups obtained by removing two hydrogen atoms from the carbon atoms or hetero atoms that constitute the ring of pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, and triazole. Divalent heterocyclic groups include groups in which multiple of these groups are bonded.

[0052] The "alkenyl group" may be either straight-chain or branched, and may have a substituent. The number of carbon atoms in a straight-chain alkenyl group, not including the number of carbon atoms in the substituent, is usually 2 to 30, preferably 3 to 20. The number of carbon atoms in a branched alkenyl group, not including the number of carbon atoms in the substituent, is usually 3 to 30, preferably 4 to 20.

[0053] The "cycloalkenyl group" may have a substituent. The number of carbon atoms in the cycloalkenyl group is usually 3 to 30, preferably 4 to 20, not including the carbon atoms in the substituent.

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

[0055] The "alkynyl group" may be either linear or branched, and may have a substituent. The number of carbon atoms in an alkynyl group, not including the carbon atoms of the substituent, is usually 2 to 20, preferably 3 to 20. The number of carbon atoms in a branched alkynyl group, not including the carbon atoms of the substituent, is usually 4 to 30, preferably 4 to 20.

[0056] The "cycloalkynyl group" may have a substituent. The number of carbon atoms in the cycloalkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atoms of the substituent.

[0057] Examples of the alkynyl group and cycloalkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which these groups have a substituent.

[0058] The term "halogen atom" refers to 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. The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. The number of carbon atoms in the substituted amino group is usually 1 to 30, preferably 2 to 18, and more preferably 2 to 12.

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

[0061] An "oxycarbonyl group" is -COOR ｂ R is a group represented by the formula: 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 in the oxycarbonyl group is usually 2 to 60, preferably 2 to 40, more preferably 2 to 20, and even more preferably 2 to 10.

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

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

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

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

[0066] The "boryl group" may have a substituent, and is preferably a substituted boryl group. Examples of the substituent that the boryl group has 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, and the like, and the aryl group or aryloxy group is preferred.

[0067] The "sulfonic acid group" may have a substituent, and is preferably a substituted sulfonic acid group. Examples of the substituent on the sulfonic acid group include a halogen atom, an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, and an alkoxy group, and preferably an alkyl group or an aryl group. A substituted sulfonic acid group in which the substituent is an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkoxy group, or the like is also called a "sulfonate ester group." The number of carbon atoms in the substituted sulfonic acid group is usually 0 to 30, preferably 1 to 18, and more preferably 2 to 12.

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

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

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

[0071] A "sulfonyl group" is —SO ２ R ｂ R is a group represented by the formula: ｂ has the same meaning as 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, and 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 a substituent.

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

[0074] [1. Color conversion material] The color conversion material according to the first embodiment of the present disclosure contains a compound (A) having a fused aromatic hydrocarbon skeleton in which six or more rings are fused. The color conversion material of this embodiment is a color conversion material that converts incident light into light with 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] The color conversion material of this embodiment has an excellent luminance life, and can therefore 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, as determined by the following method, at an excitation wavelength of 460 nm is preferably 20 to 100%, more preferably 40 to 100%, even more preferably 50 to 100%, particularly preferably more than 50% and 100% or less, particularly preferably 60 to 95%, and even more preferably 70 to 90%.

[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 applying a solution containing a color conversion material to a synthetic quartz glass substrate by spin coating and drying it to form a color conversion layer on the synthetic quartz glass substrate. 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. The spin coating is performed at a rotation speed of 1000 to 4000 rpm so that the resulting film has a thickness of 100 nm after drying.

[0079] To evaluate the color conversion efficiency, an evaluation device (for example, an absolute PL quantum yield measurement device C9920-02 manufactured by Hamamatsu Photonics KK) is used. The evaluation device disperses light emitted from a xenon lamp, which is an excitation light source, causing a measurement sample placed in an integrating sphere to emit light. The light collected by the integrating sphere is wavelength-resolved and photometrically measured using a multichannel spectrometer to obtain an emission spectrum. To calculate the color conversion efficiency, first, a reference excitation light is measured using a synthetic quartz glass substrate without a color conversion layer, and then the sample emission and the unabsorbed remaining sample excitation light are measured from a sample (measurement sample) on which a color conversion layer is formed. Next, the number of photons of each light is determined based on the measurement results, and the color conversion material is calculated using the following formula (i):

[0080]

[0081] η: Color conversion efficiency m: Number of photons of excitation light irradiated onto 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-converting material of this embodiment is preferably 50% by mass or more, more preferably 70% by mass or more, and usually 100% or less. Note that, since the polymer compound (AB) described later is also compound (A), when the color-converting material of this embodiment contains the polymer compound (AB) described later, the content of 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 one or more types of compound (A). Compound (A) is a compound having one or more fused aromatic hydrocarbon skeletons in which six or more rings are fused per molecule.

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

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

[0086] From the viewpoint of the luminance life and ease of synthesis of the color conversion material of this embodiment, the ring constituting the fused aromatic hydrocarbon skeleton is preferably a 5- to 8-membered ring, more preferably a 5- or 7-membered ring, and even more preferably a 6-membered ring. It is particularly preferable that the fused aromatic hydrocarbon skeleton is a skeleton in which only 6-membered rings are fused.

[0087] Compound (A) may be a compound consisting of only a fused aromatic hydrocarbon skeleton, or a compound in which the hydrogen atoms directly bonded to the carbon atoms constituting the fused rings of the fused aromatic hydrocarbon skeleton are substituted with substituents, or a polymer compound containing structural units derived from these compounds. The substituents that may be introduced into the fused aromatic hydrocarbon skeleton may contain heteroatoms, but preferably do not contain heteroatoms.

[0088] The substituent that may be introduced into the condensed aromatic hydrocarbon skeleton 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, because the luminance life of the color conversion material of this embodiment is excellent.

[0089] A preferred fused aromatic hydrocarbon skeleton is a skeleton having a structure represented by formula (1) or (2) and fused with two or more rings. The fusion positions of the structure represented by formula (1) or (2) with the two or more rings are not particularly limited.

[0090] The number of rings fused with the structure represented by formula (1) or formula (2) is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 4, from the viewpoints of the luminance life and ease of synthesis of the color conversion material of this embodiment.

[0091] The fused aromatic hydrocarbon skeleton having the structure represented by formula (1) or formula (2) is preferably a fused aromatic hydrocarbon skeleton represented by any one of formulas (3') to (6').

[0092]

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

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

[0095] Examples of the low molecular weight compound (A) include compounds represented by the following formulas and compounds in which a substituent is further bonded to the compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

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

[0102] [1-1-3. Polymer Compound (A)] The polymer compound (A) contains one or more structural units (A) having the above-described condensed aromatic hydrocarbon skeleton. The polymer compound (A) may contain the structural unit (A) in the main chain, side chain, or at the terminals. However, since the luminance life of the color conversion material of this embodiment is excellent, it is preferable that the structural unit (A) be contained as a repeating unit in the main chain.

[0103] The polymer compound (A) may contain one or more structural units other than the structural unit (A). The other structural units may be any of the structural units not having the above-mentioned condensed aromatic hydrocarbon skeleton, but the structural unit (Y), the structural unit (Z), and the structural unit (B) described below are preferred. The structural unit (A), the structural unit (Y), the structural unit (Z), and the structural unit (B) are different from one another.

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

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

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

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

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

[0109] When the low molecular weight compound (A) is a fused aromatic hydrocarbon represented by formula (6), the structural unit obtained by removing x hydrogen atoms from the low molecular weight compound (A) is preferably a structural unit obtained by removing x hydrogen atoms from positions selected from the group consisting of the 2-, 3-, 7-, 11-, 12-, and 16-positions of the fused aromatic hydrocarbon represented by formula (6) and substituents directly bonded to these positions, and more preferably a structural unit obtained by removing x hydrogen atoms from positions selected from the group consisting of the 7- and 16-positions.

[0110] Examples of the structural unit (A) include structural units represented by formulae (AM-1) to (AM-71), and structural units in which a substituent is further bonded to these structural units.

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] The total content of the structural units (A) in the polymer compound (A) is preferably 25 to 100 mol %, more preferably 30 to 99.99 mol %, even more preferably 40 to 90 mol %, particularly preferably 45 to 80 mol %, and especially preferably 47 to 70 mol %, relative to the total amount of all structural units contained in the polymer compound (A), since this results in excellent stability of the polymer compound (A).

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

[0118]

[0119] [In the formula, Ar Ｙ１ represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. These groups may have a substituent.]

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

[0121] Ar Ｙ１ In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the preferred range of the arylene group and the preferred range of the divalent heterocyclic group are respectively represented by Ar Ｙ１ The preferred range of the arylene group represented by Ｙ１ The preferred range is the same as that of the divalent heterocyclic group represented by the following formula:

[0122] Ar Ｙ１ The substituent that the group represented by the formula (I) may have is 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 a substituent.

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

[0124]

[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 a substituent. Ｙ１ may be the same or different, and adjacent R Ｙ１ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

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

[0127]

[0128] [In the formula, R Ｙ１ represents the same meaning as above. Ｙ１ is -C(R Ｙ２ ) ２ -, -C(R Ｙ２ ) = C(R Ｙ２) - or -C(R Ｙ２ ) ２ -C(R Ｙ２ ) ２ represents a group represented by -. Ｙ２ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group. These groups may have a substituent. Ｙ２ may be the same or different, R Ｙ２ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0129] R Ｙ２ is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably an alkyl group or an aryl group. These groups may have a substituent.

[0130] X Ｙ１ In the formula, -C(R Ｙ２ ) ２ Two R in the group represented by - 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, and R Ｙ２ When —C(R Ｙ２ ) ２ The group represented by - 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]

[0132] X Ｙ１In the formula, -C(R Ｙ２ ) = C(R Ｙ２ Two R Ｙ２ The combination of the above is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group. These groups may have a substituent.

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

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[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 %, even more preferably 10 to 60 mol %, particularly preferably 20 to 55 mol %, and especially preferably 30 to 53 mol %, relative to the total amount of all structural units contained in the polymer compound (A), in order to achieve excellent stability of the polymer compound (A).

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

[0145]

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

[0147] Examples of the structural unit (Z) include structural units represented by formula (Z-1) or formula (Z-2). From the viewpoint of the luminance life of the color conversion material of this embodiment, the structural unit represented by formula (Z-1) is preferred.

[0148]

[0149] [In the formula, R Ｙ１ has the same meaning as above. 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 a substituent.]

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

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

[0152]

[0153]

[0154]

[0155]

[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 %, even more preferably 10 to 60 mol %, particularly preferably 20 to 55 mol %, and especially preferably 30 to 53 mol %, relative to the total amount of all structural units contained in the polymer compound (A), since this results in excellent stability of the polymer compound (A).

[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 weight compound (A), compound (B) is one or more compounds selected from the group consisting of the following low molecular weight compound (B) and the following polymer compound (B). When compound (A) is a polymer compound (A), compound (B) is one or more compounds selected from the group consisting of the following low molecular weight compound (B), the following polymer compound (AB), and the following polymer compound (B).

[0158] Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound that satisfies the following condition I. Polymer compound (AB): The polymer compound (AB) is a polymer compound that includes the structural unit (A) and a structural unit (B) that satisfies the following condition II, and also falls under the category of polymer compound (A). Polymer compound (B): The polymer compound (B) is a polymer compound that includes a structural unit (B) that satisfies the following condition II (excluding those that fall under the category of polymer compound (A)).

[0159] (Condition I) When compound (A) is a low molecular weight compound (A): the energy level of the lowest singlet excited state of low molecular weight compound (A) > the energy level of the lowest singlet excited state of low molecular weight compound (B). When compound (A) is a high molecular weight compound (A): the energy level of the lowest singlet excited state of a compound formed by bonding a hydrogen atom to a bond of structural unit (A) > the energy level of the lowest singlet excited state of low molecular weight compound (B).

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

[0161] (Condition III) When the compound (A) is a low molecular weight compound (A): 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]. When the compound (A) is a high molecular weight 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 weight compound (B) per unit mass].

[0162] Compound (B) is a compound that can function as a luminescent dye, and is preferably a compound that emits green light (wavelength 500 to 570 nm) or red light (wavelength 620 to 780 nm).

[0163] The compound (B) may be used alone or in any combination and ratio of two or more. The color conversion material preferably contains one to four types of compound (B), and more preferably one to two types of compound (B), because the color conversion efficiency is further improved by cascade energy transfer.

[0164] A preferred embodiment of the color conversion material containing compound (B) is a color conversion material that contains a polymer compound (A) and one or more compounds (B) selected from the group consisting of a low molecular weight compound (B), polymer compounds (AB), and polymer compounds (B), satisfies condition III, and in which compound (B) contains two or more compounds and / or structural units selected from the group consisting of low molecular weight compounds (B) and structural units (B).

[0165] The energy level of the lowest singlet excited state of various compounds is determined by the following method. First, the ground state of the compound is structurally optimized using B3LYP-level density functional theory. 6-31G(d) is used as the basis function. Then, using the resulting structurally optimized structure, the energy level of the lowest singlet excited state of the compound is calculated using B3LYP-level time-dependent density functional theory. However, if the compound contains an atom for which 6-31G(d) cannot be used, LANL2DZ is used for that atom. The quantum chemistry calculation program used for the calculation is Gaussian 16.

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

[0167] [1-2-1. Low Molecular Weight Compound (B)] The low molecular weight compound (B) is preferably an organoboron compound as long as it satisfies condition I. The organoboron compound is preferably a low molecular weight compound represented by any one of formulas (7) to (9), and more preferably a low molecular weight compound represented by formula (7) or formula (9).

[0168] (Low Molecular Weight Compound Represented by Formula (7) or (8)) The number of carbon atoms in the aromatic hydrocarbon rings represented by Ring A, Ring B, and Ring C, not including the number of carbon atoms in substituents, is usually 6 to 60, preferably 6 to 18, more preferably 6 to 10, and even more preferably 6. Examples of aromatic hydrocarbon rings include benzene, fluorene, naphthalene, anthracene, and phenanthrene, and benzene is preferred.

[0169] The number of carbon atoms in the aromatic heterocycle represented by ring A, ring B, and ring C, not including 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 aromatic heterocycles include pyridine, diazabenzene, azanaphthalene, diazanaphthalene, carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, and thiophene.

[0170] The substituents that may be contained in the ring A, ring B, and ring C 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, because these groups provide a more excellent color conversion efficiency in this embodiment.

[0171] The more detailed structures of the A ring, B ring and C ring (CA, CB and CC) are explained below.

[0172]

[0173] Specific examples of the structure (CA) of the A ring include structures represented by formulae (CA01) to (CA38). In order to achieve better color conversion efficiency in this embodiment, the structures represented by formulae (CA01) to (CA19) are preferred, the structures represented by formulae (CA01) to (CA05) are more preferred, and the structure represented by formula (CA01) is even more preferred.

[0174]

[0175]

[0176]

[0177]

[0178] [In the formula, R Ｙ２ and R ａ has the same meaning as above. Ｙ４ represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. These groups may have a substituent. R Ｙ４When a plurality of are present, they may be the same or different. A hydrogen atom in the formula may be replaced by a substituent that ring A may have.]

[0179] Specific examples of the structure (CB) of the B ring include structures represented by formulae (CB01) to (CB24). In order to achieve better color conversion efficiency in this embodiment, the structures represented by formulae (CB01) to (CB13) are preferred, the structures represented by formulae (CB01) to (CB05) are more preferred, and the structure represented by formula (CB01) is even more preferred.

[0180]

[0181]

[0182]

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

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

[0185]

[0186]

[0187]

[0188] [In the formula, R Ｙ２ , R Ｙ４ and R ａhas the same meaning as 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, and in formula (8), * is bonded to Y ３ represents the bonding position with

[0189] In the formulae (CA02) to (CA05), (CB02) to (CB05), and (CC02) to (CC05), —C(R Ｙ２ ) ２ Two R in the group represented by - 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; and more preferably one is an alkyl group or cycloalkyl group and the other is an aryl group. These groups may have a substituent. -C(R Ｙ２ ) ２ Two R in the group represented by - Ｙ２ are bonded to each other to form a ring together with the carbon atoms, -C(R Ｙ２ ) ２ The group represented by - 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 a substituent.

[0190]

[0191] In the formulae (CA09) to (CA12), (CB08) to (CB10), and (CC08) to (CC10), —C(R Ｙ２ ) = C(R Ｙ２ Two R Ｙ２ The combination of the above is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group. These groups may have a substituent.

[0192] In formulae (CA20) to (CA26), formulae (CB14) to (CB18), and formulae (CC14) to (CC18), R Ｙ４is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.

[0193] In the low molecular weight compound represented by formula (7) or formula (8), the combination of ring A, ring B, and ring C is preferably a structure represented by formulas (CA01) to (CA05), ring B is a structure represented by formulas (CB01) to (CB05), and ring C is a structure represented by formulas (CC01) to (CC05), since the color conversion efficiency of this embodiment is more excellent; more preferably, ring A is a structure represented by formula (CA01), ring B is a structure represented by formulas (CB01) to (CB05), and ring C is a structure represented by formulas (CC01) to (CC05); and even more preferably, ring A is a structure represented by formula (CA01), ring B is a structure represented by formula (CB01), and ring C is a structure represented by formula (CC01).

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

[0195] Y ２ and Y ３ At least one of the above is preferably —N(—Ry)—, since this embodiment has a higher color conversion efficiency. ２ and Y ３ It is more preferable that both of the groups 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, since this embodiment provides a more excellent color conversion efficiency, more preferably a hydrogen atom or an aryl group which may have a substituent, and even more preferably an aryl group which may have a substituent.

[0197] When Ry is bonded to ring A, ring B or ring C via a linking group, examples of the linking group include a direct bond; —O—, —S—, —CH ２- and other divalent groups; and trivalent groups such as a boron atom; and the like.

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

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

[0200]

[0201] (Method for producing a 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. In addition, for example, WO 2007 / 063754, WO 2008 / 056746, WO 2011 / 032686, WO 2012 / 096263, JP 2009-227663 A, JP 2010-275255 A, Advanced Materials, Vol. 26, pp. 7931-7958, 2014 It can be synthesized in accordance with the method described.

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

[0203] R １ ~R ９ The cycloalkyl group represented by the formula (I) preferably has 3 to 20 carbon atoms.

[0204] R １ ~R ９ The monovalent heterocyclic group represented by the formula (I) preferably has 2 to 20 carbon atoms.

[0205] R １ ~R ９ The alkenyl group represented by the formula (I) preferably has 2 to 20 carbon atoms.

[0206] R １~R ９ The cycloalkenyl group represented by the formula (I) preferably has 3 to 30 carbon atoms, more preferably 4 to 20 carbon atoms.

[0207] R １ ~R ９ The alkynyl group represented by the formula (I) preferably has 2 to 20 carbon atoms.

[0208] R １ ~R ９ The alkoxy group represented by the formula (I) preferably has 1 to 20 carbon atoms.

[0209] R １ ~R ９ The alkylthio group represented by the formula (I) preferably has 1 to 20 carbon atoms.

[0210] R １ ~R ９ The aryloxy group represented by the formula (I) preferably has 6 to 40 carbon atoms.

[0211] R １ ~R ９ The arylthio group represented by the formula (I) preferably has 6 to 40 carbon atoms.

[0212] R １ ~R ９ The aryl group represented by the formula (I) preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms.

[0213] R １ ~R ９ The aryl group represented by the formula (I) 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 especially preferably a phenyl group.

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

[0215] R １ ~R ９ The heteroaryl group represented by the formula (I) preferably has 2 to 40 carbon atoms, and more preferably 2 to 30 carbon atoms.

[0216] R １ ~R ９ The heteroaryl group represented by the formula (I) 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.

[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 on 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 substituted amino group represented by the formula (I) preferably has 2 to 50 carbon atoms, more preferably 6 to 40 carbon atoms, and even more preferably 6 to 30 carbon atoms.

[0219] The phosphine oxide group is —P(═O)R １０ R １１ R is a group represented by the formula: １０ and R １１ is R １ ~R ９ It has the same meaning as:

[0220] R １ ~R ９ The substituents that may be contained in the alkyl group include, but are not limited to, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryloxy groups, arylthio groups, aryl groups, halogen atoms, cyano groups, aldehyde groups, carbonyl groups, carboxy groups, oxycarbonyl groups, carbamoyl groups, amino groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, sulfonic acid groups, and phosphine oxide groups. These substituents may further contain a substituent.

[0221] R １ ~R ９ The fact that adjacent groups of R are bonded to each other directly or via a linking group to form a ring means that R １ ~R ９ Any two adjacent groups (e.g., 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. Furthermore, these rings may be fused with another ring.

[0222] The low molecular weight compound represented by formula (9) exhibits a high luminescence quantum yield and a small half-width of the emission spectrum, and therefore can achieve both efficient color conversion and high color purity. Furthermore, the low molecular weight compound represented by formula (9) can be obtained by combining an appropriate R １ ~R ９ By having R, various characteristics and physical properties such as luminous efficiency, color purity, thermal stability, light stability, and dispersibility can be adjusted. １ , R ３ , R ４ and R ６ Compared to when all are hydrogen, R １ , R ３ , R ４ and R ６ When at least one of is an alkyl group, an aryl group, or a heteroaryl group, the compound exhibits higher thermal stability and light stability.

[0223] R １ , R ３ , R ４ and R ６ When at least one of the groups 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, or a hexyl group. Of 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. Furthermore, from the viewpoint of preventing concentration quenching and improving luminescence quantum yield, the alkyl group is preferably a sterically bulky tert-butyl group. Furthermore, from the viewpoint of ease of synthesis and ease of raw material availability, the alkyl group is preferably a methyl group.

[0224] R １ , R ３ , R ４ and R ６ When at least one of the groups 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 the groups 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.

[0226] R １ , R ３ , R ４ and R ６ In view of increasing the solubility in a solvent, it is preferable that each of the alkyl groups is an alkyl group. In this case, it is preferable that the alkyl group is a methyl group in view of ease of synthesis and availability of raw materials.

[0227] R １ , R ３ , R ４ and R ６ is 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] Although some substituents improve multiple properties, only a limited number of substituents exhibit sufficient performance in all areas. It is particularly difficult to achieve both high luminous efficiency and high color purity. Therefore, by introducing multiple types of substituents into the low-molecular-weight compound represented by formula (9), it is possible to obtain a compound with a well-balanced luminous property, color purity, etc.

[0229] In particular, R １ , R ３ , R ４ and R ６ are all aryl groups, for example, R １ ≠R ４ , R ３ ≠R ６ , R １ ≠R ３ or R ４ ≠R ６ For example, R １ , R ３ , R ４ and R ６are preferably not the same groups. Here, "≠" indicates that they are groups with different structures. For example, R １ ≠R ４ is R １ and R ４ This means that the low molecular weight compound represented by formula (9) has both an aryl group that affects color purity and an aryl group that affects luminous efficiency, allowing for fine adjustment.

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

[0231] The aryl group that mainly affects color purity is preferably an aryl group substituted with an electron-donating group. In organic electronics theory, an electron-donating group is an atomic group that donates electrons to the substituted atomic group due to the inductive effect or resonance effect. Examples of electron-donating groups include those whose Hammett's rule substituent constant (σp(para)) takes a negative value. The Hammett's rule substituent constant (σp(para)) can be cited from the Revised 5th Edition of the Basic Chemistry Handbook (II-380 pages).

[0232] Specific examples of the electron-donating group include an alkyl group (σp of a methyl group: −0.17), an alkoxy group (σp of a methoxy group: −0.27), and an amino group (—NH ２Examples include σp of -0.66). 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 viewpoints of improving dispersibility and preventing quenching due to aggregation of molecules, the electron-donating group is preferably a tert-butyl group or a methoxy group. Furthermore, mainly from the viewpoint of improving luminous efficiency, the electron-donating group is preferably a bulky group such as a tert-butyl group or a methoxy group.

[0233] The substitution position of the electron-donating group in the aryl group is preferably the meta or para position relative to the bond position with the pyrromethene skeleton, since it is necessary to suppress bond twisting in order to enhance 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. １ , R ３ , R ４ and R ６ The combination is not particularly limited.

[0235]

[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 ２and R ５ is preferably a hydrogen atom.

[0237] R ８ and R ９ is 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, R is preferred because it is stable to excitation light and can provide a higher fluorescence quantum yield. ８ and R ９ is preferably a fluorine atom, a cyano group, or a fluorine-containing aryl group. ８ and R ９ is preferably a fluorine atom or a cyano group. ８ and R ９ Preferably, one or both of the groups is a cyano group.

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

[0239] In addition, in formula (9), X is C-R ７ From the viewpoint of light stability, it is preferable that X is C—R ７ When the formula (9) is a formula (9), the decrease in the luminescence intensity over time of the low molecular weight compound represented by the formula (9) can be suppressed by the substituent R ７ Specifically, R ７ When R is hydrogen, this site is highly reactive and easily reacts with moisture and oxygen in the air. This causes the decomposition of the low molecular weight compound represented by formula (9). ７When R is a substituent with a large degree of freedom of movement of the molecular chain, such as an alkyl group, the reactivity decreases, but the low molecular weight compound represented by formula (9) aggregates over time in the color-changing film described later, resulting in a decrease in luminescence intensity due to concentration quenching. ７ is preferably a group that is rigid and has a small degree of freedom of movement, making it unlikely to cause aggregation, and specifically is preferably an aryl group or a heteroaryl group.

[0240] From the viewpoints of providing a higher fluorescence quantum yield, being less susceptible to thermal decomposition, and photostability, X is preferably C-R ７ and R ７ is preferably an aryl group. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group, in order not to impair the emission wavelength.

[0241] Furthermore, in order to enhance the photostability of the low molecular weight compound represented by formula (9), R ７ It is necessary to moderately suppress the twisting of the carbon-carbon bond of the pyrromethene skeleton. ７ If the twist of the carbon-carbon bond of the pyrromethene skeleton is too large, the reactivity to excitation light increases, and the photostability decreases. 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 suitably bulky substituent from the viewpoint of suppressing molecular aggregation and improving luminous efficiency and durability.

[0243] More preferred examples of such bulky substituents include R ７ The structure is as follows.

[0244]

[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 a substituent. k is an integer of 1 to 3. When k is 2 or more, multiple 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 preferred examples include a phenyl group and a naphthyl group. 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 molecular aggregation. 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] From the viewpoints of controlling the fluorescence wavelength or absorption wavelength and improving compatibility with solvents, 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. From the viewpoints of improving dispersibility and preventing quenching due to molecular aggregation, r is preferably a tert-butyl group or a methoxy group.

[0248] In addition, as another embodiment of the low molecular weight compound represented by formula (9), R １ ~R ７ It is preferred that at least one of R is an electron-withdrawing group. １ ~R ６ At least one of R is an electron-withdrawing group; ７ is an electron-withdrawing group; or R １ ~R ６At least one of R is an electron-withdrawing group, and ７ is an electron-withdrawing group. By introducing an electron-withdrawing group into the pyrromethene skeleton of the low-molecular-weight compound represented by formula (9), the electron density of the pyrromethene skeleton can be significantly reduced. This further improves the stability of the compound against oxygen, and as a result, the durability of the low-molecular-weight compound represented by formula (9) can be further improved.

[0249] An electron-withdrawing group, also known as an electron-accepting group, is an atomic group that attracts electrons from a substituted atomic group due to an inductive effect or a resonance effect in organic electronics. Examples of electron-withdrawing groups include those whose Hammett's substituent constant (σp(para)) is a positive value. The Hammett's substituent constant (σp(para)) can be cited from the revised 5th edition of the Basic Chemistry Handbook (page II-380). Note that, although there are examples in which a phenyl group also takes a positive value as described above, in the present disclosure, phenyl groups are not included in the electron-withdrawing groups.

[0250] Examples of the electron-withdrawing group include -F (σp: +0.06), -Cl (σp: +0.23), -Br (σp: +0.23), -I (σp: +0.18), and -CO ２ R １２ (σp:R １２ is an ethyl group, +0.45), -CONH ２ (σp: +0.38), -COR １２ (σp:R １２ is a methyl group, +0.49), -CF ３ (σp: +0.50), -SO ２ R １２ (σp:R １２ is a methyl group, +0.69), and -NO ２ (σp: +0.81) and the like. １２ each independently represents a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a heterocyclic group having 5 to 30 ring 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 R in formula (9) is an electron-withdrawing group.２ and R ５ is a substitution position that greatly affects the electron density of the pyrromethene skeleton, and R ２ and R ５ By introducing an electron-withdrawing group into the compound, the electron density of the pyrromethene skeleton can be efficiently reduced, and the stability against oxygen can be further improved, thereby further improving durability.

[0252] Furthermore, in formula (9), R ２ and R ５ is more preferably an electron-withdrawing group, because this further improves the stability of the low-molecular-weight compound represented by formula (9) against oxygen, thereby significantly improving durability.

[0253] The electron-withdrawing group is preferably a group containing a fluorine atom, which can further reduce the electron density of the pyrromethene skeleton, improve the stability of the low-molecular-weight compound represented by formula (9) against oxygen, and improve durability.

[0254] Preferred 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 sulfonate ester group, a sulfonamide group, and a cyano group. These electron-withdrawing groups are preferred because they are difficult to chemically decompose.

[0255] More preferred electron-withdrawing groups include fluorine-containing alkyl groups, acyl groups, oxycarbonyl groups, amide groups, sulfonyl groups, sulfonate ester groups, sulfonamide groups, and cyano groups. These electron-withdrawing groups prevent concentration quenching and improve the luminescence quantum yield. Among these, the most preferred electron-withdrawing group is the oxycarbonyl group.

[0256] More preferred electron-withdrawing groups include a fluorine-containing acyl group, a fluorine-containing ester group, a fluorine-containing amide group, a fluorine-containing sulfonyl group, a fluorine-containing sulfonate ester group, and a fluorine-containing sulfonamide group. These electron-withdrawing groups efficiently reduce the electron density of the pyrromethene boron complex skeleton and improve the stability of the low-molecular-weight compound represented by formula (9) against oxygen, thereby further improving the durability of the low-molecular-weight compound represented by formula (9).

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

[0258] One preferred example of the low molecular weight compound represented by formula (9) is R １ , R ３ , R ４ and R ６ is an alkyl group, and X is C—R ７ and R ７ is a group represented by formula (10): In this case, it is particularly preferable that r in formula (10) is a phenyl group.

[0259] Another preferred example of the low molecular weight compound represented by formula (9) is R １ , R ３ , R ４ and R ６ is selected from Ar-1 to Ar-6 above, and X is C-R ７ and R ７ is a group represented by formula (10): In this case, r in 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 formula (9) is R １ , R ３ , R ４ and R ６is an alkyl group, and R ２ and R ５ is an oxycarbonyl group, and X is C—R ７ and R ７ is a group represented by formula (10): In this case, it is particularly preferable that r in formula (10) is a phenyl group.

[0261] Another preferred example of the low molecular weight compound represented by formula (9) is R １ , R ３ , R ４ and R ６ is selected from Ar-1 to Ar-6 above, and R ２ and R ５ is an oxycarbonyl group, and X is C—R ７ and R ７ is a group represented by formula (10). In this case, R ７ In formula (10), r 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 formula (9), for example, a compound represented by the following formula is preferred.

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] (Method for Producing a 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-A-8-509471 or JP-A-2000-208262. That is, the target compound can be obtained by reacting a pyrromethene compound with a metal salt in the presence of a base.

[0274] A low molecular weight compound represented by formula (9), wherein R ８ and R ９ A pyrromethene-boron fluoride complex in which R is a fluorine atom can be synthesized in accordance with the methods described, for example, in J. Org. Chem., vol. 64, No. 21, pp. 7813-7819 (1999) and Angew. Chem., Int. Ed. Engl., vol. 36, pp. 1333-1335 (1997). That is, a compound represented by formula (11) and a compound represented by formula (12) are heated in 1,2-dichloroethane in the presence of phosphorus oxychloride, and then reacted with a compound represented by formula (13) in 1,2-dichloroethane in the presence of triethylamine, thereby synthesizing a low molecular weight compound represented by formula (9). In formulas (11) to (13), R １ ~R ９ is the same as described above, and J represents a halogen atom.

[0275]

[0276] Furthermore, when introducing an aryl group or a heteroaryl group, a carbon-carbon bond can be formed by a coupling reaction between a halogenated derivative and a boronic acid or a boronate ester derivative. Similarly, when introducing an amino group or a carbazolyl group, a carbon-nitrogen bond can be formed by a coupling reaction between a halogenated derivative and an amine or a carbazole derivative in the presence of a metal catalyst such as palladium.

[0277] [1-2-2. Polymer compound (AB)] The polymer compound (AB) is a polymer compound (AB) that contains one or more of the above-mentioned structural units (A) and one or more structural units (B) that satisfy condition II, and also corresponds to the polymer compound (A). The polymer compound (AB) may contain these structural units in the main chain, side chain, or terminal, but it is preferable that the main chain contains these structural units as repeating units.

[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 thereof are also the same.

[0279] The polymer compound (AB) may contain one or more units other than the structural unit (A) and the structural unit (B). As such other structural units, the aforementioned structural unit (Y) and structural unit (Z) are preferred. The structural unit (Y) and structural unit (Z) in the polymer compound (AB) have the same meanings as the structural unit (Y) and structural unit (Z) in the polymer compound (A), respectively, and the preferred embodiments thereof 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 therefore does not have the above-mentioned fused 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 weight compound represented by any one of formulas (7) to (9). In the structural unit derived from a low molecular weight compound represented by any one of formulas (7) to (9), the low molecular weight compound represented by any one of formulas (7) to (9) is synonymous with the low molecular weight compound represented by any one of formulas (7) to (9) shown as low molecular weight compound (B), and preferred embodiments thereof are also the same.

[0281] The total content of the structural unit (A) in the polymer compound (AB) is preferably 25 to 100 mol %, more preferably 30 to 99.99 mol %, even more preferably 40 to 90 mol %, particularly preferably 45 to 80 mol %, and especially preferably 47 to 70 mol %, relative to the total amount of all structural units contained in the polymer compound (AB), since this results in excellent stability of the polymer compound (AB).

[0282] The total content of the structural unit (B) in the polymer compound (AB) is preferably 0.001 to 20 mol %, more preferably 0.01 to 10 mol %, and even more preferably 0.01 to 5 mol %, relative to the total amount of all structural units contained in the polymer compound (AB), since this results in excellent stability of the polymer compound (AB).

[0283] When the polymer compound (AB) contains the structural unit (Y), the total content of the structural unit (Y) in the polymer compound (AB) is preferably 0.01 to 75 mol %, more preferably 0.01 to 70 mol %, even more preferably 10 to 60 mol %, particularly preferably 20 to 55 mol %, and especially preferably 30 to 53 mol %, relative to the total amount of all structural units contained in the polymer compound (AB), in order to achieve excellent stability of the polymer compound (AB).

[0284] When the polymer compound (AB) contains the structural unit (Z), the total content of the structural unit (Z) in the polymer compound (AB) is preferably 0.01 to 75 mol %, more preferably 0.01 to 70 mol %, even more preferably 10 to 60 mol %, particularly preferably 20 to 55 mol %, and especially preferably 30 to 53 mol %, relative to the total amount of all structural units contained in the polymer compound (AB), since this results in excellent stability of the polymer compound (AB).

[0285] (Structural Unit Derived from a Low Molecular Weight Compound Represented by Formula (7) or Formula (8)) A structural unit derived from a low molecular weight compound represented by Formula (7) or Formula (8), which is a preferred embodiment of structural unit (B), is a structural unit obtained by removing y or more hydrogen atoms from a low molecular weight compound represented by Formula (7) or Formula (8). Here, y is an integer of 1 or greater. It should be noted that one or more of the y hydrogen atoms removed from the low molecular weight compound represented by Formula (7) or Formula (8) may be hydrogen atoms possessed by a substituent. From the viewpoint of ease of synthesis of the polymer compound, y is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 2.

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

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] (Structural Unit Derived from a Low Molecular Weight Compound Represented by Formula (9)) A structural unit derived from a low molecular weight compound represented by formula (9), which is a preferred embodiment of structural unit (B), is a structural unit obtained by removing z or more hydrogen atoms from a low molecular weight compound represented by formula (9). Here, z is an integer of 1 or greater. It should be noted that one or more of the z hydrogen atoms removed from the low molecular weight compound represented by formula (9) may be hydrogen atoms possessed by a substituent. From the viewpoint of ease of synthesis of the polymer compound, z is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 2.

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

[0296]

[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 the main chain, side chain, or at the terminal, but preferably contains the structural unit (B) as a repeating unit in the main chain.

[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 the preferred embodiments thereof are also the same.

[0299] The polymer compound (B) may contain one or more units other than the structural unit (B). The other structural units are preferably the structural unit (Y) and the structural unit (Z) described above. The structural unit (Y) and the structural unit (Z) in the polymer compound (B) have the same meanings as the structural unit (Y) and the structural unit (Z) in the polymer compound (A), respectively, and the preferred embodiments thereof are also the same. However, the polymer compound (B) is a compound that does not fall under the category of the polymer compound (A), and therefore, the structural units contained in the polymer compound (B) are units that do not have the above-described condensed aromatic hydrocarbon skeleton, i.e., structural units that do not fall under the category of the structural unit (A).

[0300] The total content of the structural units (B) in the polymer compound (B) is preferably 0.001 to 20 mol %, more preferably 0.01 to 10 mol %, and even more preferably 0.01 to 5 mol %, relative to the total amount of all structural units contained in the polymer compound (B), since this results in excellent stability of the polymer compound (B).

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

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

[0303] [1-3. Compositional 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. PAB-1 to PAB-9 correspond to polymer compounds (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]

[0305] The polymer compound (A) and the polymer compound (B) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other embodiments, but are preferably copolymers obtained by copolymerizing a plurality of raw material monomers.

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

[0307] [1-4. Production Method of Polymer Compound (A) and Polymer Compound (B)] Polymer compound (A) and polymer compound (B) can be produced using known polymerization methods such as those described in Chem. Rev., Vol. 109, pp. 897-1091 (2009). In addition to the above, known polymerization methods include polymerization methods using 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, examples of the method for charging the monomers include a method in which the entire amount of the monomers is charged into the reaction system all at once, a method in which a part of the monomers is charged and reacted, and then the remaining monomers are charged all at once, continuously or in portions, and a method in which the monomers are charged continuously or in portions.

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

[0310] Post-treatment of the polymerization reaction can be carried out by any of known methods, such as a method of removing water-soluble impurities by liquid separation, and a method of adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying it, either alone or in combination. When the purity of the polymer compound (AB) and the polymer compound (B) is low, they can be purified by a conventional method such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

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

[0312] [1-5. Other Components] The color conversion material of the present embodiment may contain one or more other components, such as a coumarin-based dye, a rhodamine-based dye, an inorganic fluorescent material, a fluorescent pigment, a fluorescent dye, a luminescent material such as quantum dots, and additives contained in inks described below, as needed, within the scope of not impairing the effects of the present disclosure.

[0313] However, it is preferable that the color conversion material of this embodiment is substantially free of transition metal complexes. "Substantially free of transition metal complexes" means that transition metal complexes are not intentionally blended into the color conversion material, and does not exclude, for example, a case where the color conversion material inevitably 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 mass % or less, more preferably 1.0 × 10 －２ It is less than % by mass.

[0314] The total content of other components in the color-changing material of this embodiment depends on the absorbance of the compound (A) and the transmittance of the color-changing film to be formed, but is generally 1.0 × 10 relative to 100 parts by mass of the total of the compound (A) and the compound (B). －３ Preferably, the amount is 1.0×10 to 30 parts by mass. －２ More preferably, the amount is 1.0×10 to 15 parts by mass. －１ It is more preferably up to 10 parts by mass.

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

[0316] The viscosity of the ink of this embodiment may be adjusted depending on the type of printing method. When the ink is applied to a printing method in which the solution passes through a discharge device, such as inkjet printing, the viscosity is preferably 1 to 20 mPa s at 25°C in order to prevent clogging and deflection of the ink when discharged.

[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 chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon-based solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; and fatty solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bicyclohexyl. Examples of the solvent include aromatic hydrocarbon solvents, 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. The solvents 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, and preferably 2,000 to 20,000 parts by mass, relative to 100 parts by mass of the total of compound (A) and 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 to improve coatability, transparency, or heat resistance. The ink of this embodiment may also 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, and preferably 20 to 100 parts by mass, relative to 100 parts by mass of the total of compound (A) and compound (B) contained in the color conversion material of this embodiment.

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

[0322] From the viewpoint of transparency, the binder resin is preferably one or more selected from the group consisting of acrylic resin, methacrylic resin, epoxy resin, silicone resin, and polyester resin, and from the viewpoint of heat resistance, it is preferably one or more 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 binder resins, antioxidants, surface conditioners, light stabilizers, plasticizers, and light-scattering particles, as needed.

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

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

[0326] (Surface Conditioning Agent) The ink of this embodiment preferably contains a surface conditioner from the viewpoint of improving the surface smoothness of the color-changing film. Examples of the surface conditioner include antifoaming agents and leveling agents, and specific examples include acrylic resins; polysiloxanes such as polydimethylsiloxane; silicone oils; and fluorine compounds. The surface conditioners may be used alone or in combination of two or more.

[0327] (Light Stabilizer) Examples of the light stabilizer include tertiary amines, catechol derivatives, and nickel compounds. The light stabilizers may be used alone or in combination of two or more.

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

[0329] (Light-Scattering Particles) From the viewpoint of improving light extraction efficiency, the ink of this 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. The light-scattering particles may be used alone or in combination of two or more types.

[0330] 3. Color Conversion Film A color conversion film according to a third embodiment of the present disclosure includes the color conversion material of the first embodiment, and converts incident light into light with a longer wavelength than the incident light.

[0331] The thickness of the color-changing film of this embodiment may be set appropriately within a range that allows incident light to be converted to a desired wavelength. Specifically, the thickness of the color-changing 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 a method for manufacturing a color-changing film of this embodiment will be described. The color-changing film of this embodiment can be manufactured by a method including a coating step of coating the ink of the second embodiment described above onto a substrate, and a drying step of drying the ink on the substrate. If the ink contains a thermosetting resin as a binder resin, the method may include a heat-curing step of heat-curing the thermosetting resin after the coating step. Furthermore, if the ink contains a photocurable resin as a binder resin, the method may include a photo-curing step of photo-curing the photocurable resin after the coating step.

[0333] The ink application method in the application step can be appropriately selected from known application methods such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, and nozzle coating. For example, when multiple red conversion films and multiple green conversion films are formed in multiple regions defined by partition walls (banks) or in a pattern, it is preferable to apply the ink by inkjet printing. Inkjet printing ejects ink only in the required areas, making it a coating method that is excellent in terms of ink utilization efficiency and cost.

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

[0335] After the color-changing film is produced, it may be transferred to another substrate as needed. In this case, simple methods include a method of transferring the film using a hot plate, and a method using a vacuum laminator or a dry film laminator.

[0336] [4. Light-emitting device and display device] The color conversion material according to the first embodiment can be suitably used for applications of light-emitting devices or display devices, and particularly suitable for use in display devices. Display devices have a problem in that even if the light-emitting element has a long life, the image quality deteriorates as the luminance of the color conversion material decreases over the course of operation. However, the color conversion material according to the first embodiment has a long luminance life, and therefore can maintain the image quality of the display device for a long period of time.

[0337] The light emitting device and the display device may be any device that includes the color conversion material of the first embodiment, but preferably includes the color conversion film of the third embodiment that includes the color conversion material.

[0338] In the light-emitting device and the display device, the color conversion material may be disposed in contact with the light source, or may be disposed above the light source via an optional component or space. Examples of optional components include various substrates and color filters. By using the color conversion film of the third embodiment in combination with a color filter, color purity can be more easily adjusted. Examples of color filters that can be used include 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.

[0339] Representative examples of the main configurations of light-emitting devices and display devices having color conversion films 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-mentioned components, the light-emitting device and display device of this embodiment preferably also include, as necessary, optical films such as a diffuser plate, a reflective film, a polarizing film, a polarizing reflective film, a brightness-enhancing film, and a light-guiding film; and functional layers such as a light-shielding layer, a planarizing layer, and a gas barrier layer. Furthermore, when the display device is a liquid crystal display device, it is preferable that the display device includes a liquid crystal cell equipped with a color filter, and further includes the above-mentioned optical film.

[0341] The light source can be any excitation light that emits light that can be absorbed by the color conversion material. A light source that emits light that can be absorbed by the color conversion material is preferably a light source that has a maximum emission wavelength of 400 to 500 nm, more preferably a light source that has a maximum emission 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 LED elements are preferred. Furthermore, when the light-emitting device is used for display devices and lighting, from the viewpoint of enhancing the color purity of blue light, the light source is more preferably an LED element that has a maximum emission wavelength in the above-mentioned wavelength range. The light source may have a single emission peak or multiple emission peaks, but a single emission peak is preferred to enhance the color purity of the light. Furthermore, the light source may be a combination of multiple light sources with different emission peaks.

[0342] Examples of the display device include a liquid crystal display device and an organic EL display device, and an organic EL display device is preferred. When the display device is a liquid crystal display device, the above-mentioned light-emitting device is preferably used as a backlight. When the display device is an organic EL display device, the above-mentioned light-emitting device is preferably used as a light-emitting element that displays an image, for example, in a matrix system or a segment system.

[0343] The present disclosure will be described in more detail below 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 polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of a polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of approximately 0.05% by mass, and 10 μL was injected into the SEC. The mobile phase was run at a flow rate of 1.0 mL / min. A PLgel MIXED-B (manufactured by Polymer Laboratories) was used as the column. A UV-VIS detector (manufactured by Tosoh Corporation, product name: UV-8320GPC) was used as the detector.

[0345] <NMR> NMR was measured by the following method: 5 to 10 mg of a measurement sample was dissolved in about 0.5 mL of deuterated chloroform (CDCl ３ ) or methylene dichloride (CD ２ Cl ２ The solution was dissolved in 100 ml of 100% ethanol and measured using an NMR apparatus (trade name: INOVA300 or MERCURY 400VX, manufactured by Agilent Technologies, Inc.).

[0346] <Purity> The area percentage value of high-performance liquid chromatography (HPLC) was used as an index of compound purity. Unless otherwise specified, this value is the value at UV = 254 nm using an HPLC (Shimadzu Corporation, product name: LC-20A). In this case, the compound to be measured was dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2 mass%, and 1 to 10 μL was injected into the HPLC depending on the concentration. The mobile phase for HPLC was an acetonitrile / tetrahydrofuran mixture, the ratio of which was varied from 100 / 0 to 0 / 100 (volume ratio), and the mixture was run at a flow rate of 1.0 mL / min. The column used was a Kaseisorb LC ODS 2000 (Tokyo Chemical Industry Co., Ltd.) or an ODS column with equivalent performance. The detector used was a photodiode array detector (Shimadzu Corporation, product name: SPD-M20A).

[0347] <LC-MS> LC-MS was measured using the following method. The sample to be measured was dissolved in chloroform or tetrahydrofuran to a concentration of approximately 2 mg / mL, and approximately 1 μL was injected into an LC-MS (Agilent Technologies, Inc., product name: 1100LCMSD). The mobile phase for LC-MS was a mixture of acetonitrile and tetrahydrofuran, varying in ratio, at a flow rate of 0.2 mL / min. The column used was an L-column 2 ODS (3 μm) column (Chemicals Evaluation and Research Institute, Inc., inner diameter 2.1 mm, length 100 mm, particle size 3 μm).

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

[0349] <Evaluation of Luminance Life> (Apparatus for Evaluating Luminance Life) Luminance life was evaluated by irradiating excitation light from the synthetic quartz glass substrate side of the measurement sample described below, causing the measurement sample to emit light. As the excitation light source, a laser diode NDB4216E (wavelength 450-460 nm) manufactured by Nichia Corporation was used, and as the laser driver, an ALP-7033CC manufactured by DATA SYSTEM was used. To measure the light emitted from the measurement sample, a chromatic luminance meter CHROMA METER CS-200 manufactured by Konica Minolta, Inc. was used as an emission luminance measuring device. A short-wavelength non-transmitting filter was installed at the photometric entrance of the emission luminance measuring device to prevent light with a wavelength of 470 nm or less from being measured.

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

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

[0352] First, the number of photons absorbed by the measurement sample can be calculated from formula (I) assuming that the organic compound layer (color conversion layer) has the same thickness.

[0353]

[0354] n ｅｘ－ａｂ is the number of absorbed photons, 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 represents the energy per photon at the excitation light wavelength, and T represents the transmittance. Here, the transmittance represented by T was measured using a Cary Series manufactured by Agilent Technologies, Inc. Specifically, measurements were taken in 1-nm steps over a wavelength range of 300 to 700 nm, and T was calculated from the simple average value of the measurement data over a wavelength range of 453 to 458 nm.

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

[0356]

[0357] By substituting Equation (II) into Equation (I) and rearranging the constants, Equation (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 the const. in Equation (III) is kept constant, the transmittance T is used to determine the value I at which the number of photons absorbed by each measurement sample is the same. ｅｘ can be calculated.

[0358]

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

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

[0361] (Stage 1: Synthesis of Compound 1A) After creating an argon atmosphere in a reaction vessel, 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, and the mixture was heated to 90°C and stirred at 90°C for 42 hours. The resulting reaction solution was cooled to 25°C, and then methanol (2731 mL) was added and the mixture was 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 (400MHz, CD ２ Cl ２ ) 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 creating an argon atmosphere inside the reaction vessel, 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. A 1.6 M n-butyllithium hexane solution (88 mL) was slowly added thereto, and the mixture was stirred at -70°C for 30 minutes. Compound 1A (18.5 g) was added thereto, and the mixture was heated to 0°C and then stirred for 1 hour. Subsequently, ion-exchanged water (370 mL) and toluene (370 mL) were added, and the resulting reaction solution was heated to 25°C, after which the aqueous layer was removed. The resulting organic layer was washed twice with ion-exchanged water, dried over magnesium sulfate, and then filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was recrystallized from a mixed solvent of toluene and hexane. The resulting 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 H-NMR (400MHz, CD ２ Cl ２ ) 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 creating an argon atmosphere in a reaction vessel, Compound 1B (29.9 g) and methylene chloride (600 mL) were added to the reaction vessel and cooled to -70°C. Methanesulfonic acid (0.4 mL) was added thereto, and the temperature was raised to 25°C with stirring. The mixture was then allowed to stand at 25°C for 18 hours. Ion-exchanged water (299 mL) 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 resulting crude product was purified by silica gel column chromatography (toluene) and then 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 (400MHz, CD ２ Cl ２ ) 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 creating a nitrogen atmosphere inside a reaction vessel, 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, heated to 85°C, and stirred at 85°C for 2 hours. The resulting reaction solution was cooled to 25°C, and then toluene (120 mL) was added and the mixture was filtered through silica gel. Ion-exchanged water (120 mL) was added to the resulting filtrate, 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 resulting crude product, and the mixture was dissolved by heating to 50°C. Activated carbon (2.6 g) was added to the solution, and the mixture was filtered through silica gel. The 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 H-NMR (400MHz, CD ２ Cl ２) 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>

[0370] (Stage 1: Synthesis of Compound 2A) After creating a nitrogen atmosphere inside a reaction vessel, 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, and the mixture was heated to 85°C and stirred at 85°C for 4 hours. Potassium acetate (22.6 g) was added to the resulting reaction solution, and the mixture was heated to 95°C and 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 the mixture was subjected to silica gel filtration. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. Acetonitrile (80 mL) cooled to 0°C was added to the resulting crude product, and the mixture was stirred at 0°C for 30 minutes and filtered. The resulting solid was recrystallized with 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 procedure was repeated to obtain the required amount of compound 2A.

[0371] １ H-NMR (400MHz, CDCl ３ ) 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 creating an argon atmosphere inside a reaction vessel, Compound 2A (46.0 g), Vat Orange 3 (27.3 g), 40% by mass aqueous tetrabutylammonium hydroxide solution (114 mL), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.5 g), tris(dibenzylideneacetone)dipalladium(0) (0.4 g), and toluene (655 mL) were added to the reaction vessel, and the mixture was heated to 80°C and stirred at 80°C for 3 hours. The resulting reaction solution was cooled to 25°C, and then toluene (300 mL) and ion-exchanged water (300 mL) were added, and the aqueous layer was removed. The resulting organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then filtered. The resulting 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 resulting 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 (400MHz, CDCl ３ ) 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 creating a nitrogen atmosphere in the reaction vessel, Compound 2B (15.0 g), a 1 molar borane-tetrahydrofuran complex solution (70 mL), and tetrahydrofuran (300 mL) were added to the reaction vessel and stirred at 25°C for 20 hours. To the resulting reaction solution, a 1 molar borane-tetrahydrofuran complex solution (35 mL) was added and 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 resulting 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 resulting crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and then dried under reduced pressure at 50°C to obtain Compound 2C (2.7 g). 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 (400MHz, CD ２ Cl ２ ) 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, 4 H), 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] (Stage 4: Synthesis of Compound 2D) After creating a nitrogen atmosphere in the reaction vessel, compound 2C (2.7 g) and methylene chloride (102 mL) were added to the reaction vessel and 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, saturated aqueous sodium sulfite solution (33 mL) and methylene chloride (20 mL) were added, and the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water and filtered. The resulting solid was dried under reduced pressure at 50°C to obtain a crude product. The resulting solid was repeatedly recrystallized from 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 (400MHz, CD ２ Cl ２ ) 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>

[0379] (Stage 1: Synthesis of Compound 3A) After creating a nitrogen atmosphere inside a reaction vessel, 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, and the mixture was heated to 85°C and stirred at 85°C for 30 minutes. The resulting reaction solution was cooled to 25°C, and then ion-exchanged water (100 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. Acetonitrile (80 mL) was added to the resulting crude product, and the mixture was stirred at 25°C for 1 hour and filtered. The resulting 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 (400MHz, CD ２ Cl ２ ) 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 creating an argon atmosphere inside a reaction vessel, 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, and the mixture was heated to 90°C and stirred at 90°C for 20 hours. The resulting reaction solution was cooled to 25°C, and then ion-exchanged water (20 mL) was added, and the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water, dried over magnesium sulfate, and then filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was washed with hexane to obtain a solid. The resulting 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 (400MHz, CD ２ Cl ２ ) 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 creating a nitrogen atmosphere in the reaction vessel, 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, and the mixture was heated to 0°C and stirred for 2 hours. Subsequently, ion-exchanged water (110 mL) and toluene (110 mL) were added, and the resulting reaction solution was heated to 25°C, after which the aqueous layer was removed. The resulting organic layer was washed twice with ion-exchanged water, and 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 resulting crude product was purified by silica gel column chromatography (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 (400MHz, CD ２ Cl ２ ) 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] (Stage 4: Synthesis of Compound 3D) After creating an argon atmosphere in a reaction vessel, 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. with stirring. The mixture was then allowed to stand at 25° C. for 12 hours. Ion-exchanged water (261 mL) was added thereto, 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 resulting crude product was purified by silica gel column chromatography (mixed solvent of toluene and hexane) and then dried under reduced pressure at 50° C. to obtain a crude product. The resulting 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+NH ４ ] ＋ １ H-NMR (400MHz, 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] (Stage 5: Synthesis of Compound 3E) After creating a nitrogen atmosphere in a reaction vessel, 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, and the mixture was heated to 85°C and stirred at 85°C for 3 hours. The resulting reaction solution was cooled to 25°C, and then ion-exchanged water (20 mL) was added, and the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water and concentrated under reduced pressure to obtain a crude product. The resulting 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+NH ４ ] ＋ １ H-NMR (400MHz, CD ２ Cl ２ ) 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, 2 H), 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

[0390] (Stage 1: Synthesis of Compound 4A) After creating a nitrogen atmosphere in a reaction vessel, 6,12-dibromochrysene (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 mixture was heated to 65°C and stirred at 65°C for 14 hours. The resulting reaction solution was concentrated under reduced pressure to obtain a crude product. Ion-exchanged water (2.4 L) was added to the resulting crude product, and the mixture was stirred at 25°C for 20 minutes and filtered. THF (1.2 L) was added to the resulting solid, and the mixture was cooled to 0°C, stirred at 0°C for 20 minutes, and then filtered. The resulting 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 H-NMR (400MHz, CD ２ Cl ２ ) 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 creating a nitrogen atmosphere in a reaction vessel, 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, and the mixture was heated to 90°C and stirred at 90°C for 29 hours. The resulting reaction solution was cooled to 25°C, and the precipitated insoluble matter was filtered. The resulting solid was washed with methanol to obtain a crude product. The resulting crude product was recrystallized from toluene and washed with hexane. The resulting 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 H-NMR (400MHz, CD ２ Cl２ ) 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 creating a nitrogen atmosphere inside the reaction vessel, 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, and the mixture was heated to 0°C and then stirred for 3 hours. Subsequently, ion-exchanged water (1.4 L) and toluene (1.4 L) were added, and the resulting reaction solution was heated to 25°C, after which the aqueous layer was removed. The resulting organic layer was washed twice with ion-exchanged water, dried over magnesium sulfate, and then filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (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 procedure was repeated to obtain the required amount of compound 4C.

[0395] (Stage 4: Synthesis of Compound 4D) After creating an argon atmosphere in the reaction vessel, 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, 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+NH ４ ] ＋ １ H-NMR (400MHz, CD ２ Cl ２ ) 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 and M2> Compound M1 was synthesized according to the method described in WO 2019 / 004248. Compound M2 was synthesized according to the method described in WO 2021 / 015177.

[0398]

[0399] Synthesis Example 5: Synthesis of small molecule compound M3

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

[0401] LC-MS (APCI positive): m / z=1474.4 [M] ＋ １ H-NMR (400MHz, CD ２ Cl ２ ) 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> Compounds PM2 and PM3 were synthesized according to the method described in JP 2011-174062 A. Compounds PM4 and PM5 were synthesized according to the method described in WO 02 / 045184 A. Compound PM6 was synthesized according to the method described in WO 2010 / 013006 A. Compound PM7 was synthesized according to the method described in JP 2012-255117 A. Compound PM8 was synthesized according to the method described in Journal of Chemistry, Vol. 70 (2005), pp. 4323-4331 A.

[0403]

[0404] Synthesis Example 6: Synthesis of Compound PM9

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

[0406] (Stage 2: Synthesis of Compound PM9B) After a nitrogen atmosphere was placed in a reaction vessel, compound PM9A (73.0 g), 3,6-dichlorocarbazole (32.7 g), and xylene (730 mL) were added. Copper(I) 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, and water and toluene were added. After stirring at room temperature, the aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (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] (Stage 3: Synthesis of Compound PM9C) After the reaction vessel was emptied under 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 and stirred for 1 hour. Boron tribromide (9.59 g) was added, and the mixture was heated to 0°C and stirred for 1 hour. Diisopropylethylamine (9.89 mL) was then added, and the mixture was stirred for 1 hour. The mixture was heated to 130°C and stirred for 7 hours. After cooling the reaction solution, diisopropylethylamine and a 10% by mass aqueous solution of sodium sulfite were added, and the mixture was stirred for 30 minutes. Water and toluene were added, and the mixture was stirred at room temperature, after which the aqueous layer was separated. The resulting organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain a crude product. The product was recrystallized twice using xylene and acetonitrile, and 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] (Stage 4: Synthesis of Compound PM9) After the inside of a reaction vessel was purged with argon gas, 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 the mixture was filtered through a filter fitted with silica gel. The filtrate was concentrated to obtain a crude product. The mixture was recrystallized using tetrahydrofuran and acetonitrile, and then recrystallized using toluene and acetonitrile, and dried under reduced pressure at 50°C to obtain compound PM9 (8.74 g). The HPLC area percentage value of compound S2 was 99.6%.

[0409] １ H-NMR (400MHz, CDCl ３) 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

[0411] (Stage 1: Synthesis of Compound PM10A) After creating a nitrogen atmosphere inside a reaction vessel, 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. A 1 molar aqueous solution of sodium bicarbonate (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 resulting crude product was purified by silica gel column chromatography (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 (400MHz, CDCl ３ ) δ (ppm) = 8.17 (s, 4H), 7.56-7.06 (m, 19H), 6.71 (s, 2H), 5.92 (s, 1H)

[0413] (Stage 2: Synthesis of Compound PM10B) After creating a nitrogen atmosphere in a reaction vessel, Compound PMA10A (150 mg) and methylene chloride (476.4 mL) were added to the reaction vessel and cooled to 0°C. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (4.3 g) was added to the resulting reaction solution, and the mixture was stirred at 0°C for 3 hours. A 1 molar aqueous solution of sodium bicarbonate (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 resulting crude product was purified by silica gel column chromatography (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 procedure was repeated to obtain the required amount of compound PM10B.

[0414] １ H-NMR (400MHz, CDCl ３ ) 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 creating a nitrogen atmosphere in the reaction vessel, 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 the temperature of the resulting reaction solution was lowered to 25°C, a 1 molar aqueous sodium bicarbonate 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 resulting crude product was purified by silica gel column chromatography (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 H-NMR (400MHz, CDCl ３ ) 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 creating an inert gas atmosphere in a reaction vessel, 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 heated to 80°C. (Step 2) 20% by mass 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 reaction solution was cooled to 25°C, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had been passed in advance. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P1 (2.30 g). The Mn of polymer compound P1 was 3.6 × 10 ４ and Mw is 8.7 × 10 ４ It was.

[0418] Polymer compound P1 is a copolymer composed of structural units derived from compound 1D and structural units derived from compound PM1 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0419] Example 2 Synthesis of Polymer Compound P2 (Step 1) After creating an inert gas atmosphere in a reaction vessel, 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% by mass 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, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had been passed in advance. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P2 (1.68 g). The Mn of polymer compound P2 was 7.5 × 10 ４ and Mw is 2.1 × 10 ５ It was.

[0420] Polymer compound P2 is a copolymer composed of structural units derived from compound 4D and structural units derived from compound PM3 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the raw materials charged.

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

[0422] Polymer compound P3 is a copolymer composed of structural units derived from compound 2D and structural units derived from compound PM3 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0423] Example 4 Synthesis of Polymer Compound P4 (Step 1) After creating an inert gas atmosphere in a reaction vessel, 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 added dropwise to the reaction solution, and the mixture was 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 the mixture was refluxed for 3 hours. (Step 4) The reaction solution was then cooled to 25°C, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had been passed in advance. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P4 (0.49 g). The Mn of polymer compound P4 was 1.1 × 10 ５ and Mw is 2.4 × 10 ５ It was.

[0424] Polymer compound P4 is a copolymer composed of structural units derived from compound 3E and structural units derived from compound PM2 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the charged raw materials.

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

[0426] Polymer compound P5 is a copolymer composed of structural units derived from compound 1D, structural units derived from compound PM1, and structural units derived from compound PM9 in a molar ratio of 47:50:3, according to the theoretical value calculated from the amounts of the raw materials charged.

[0427] Example 6 Synthesis of Polymer Compound P6 (Step 1) After creating an inert gas atmosphere in a reaction vessel, Compound 4D (1.52 g), Compound PM3 (0.819 g), Compound PM9 (0.064 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.85 mg), and toluene (41 mL) were added to the reaction vessel and heated to 80°C. (Step 2) 20% by mass tetraethylammonium hydroxide (20 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) The reaction solution was then cooled to 25°C, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had been passed in advance. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P6 (1.37 g). The Mn of polymer compound P6 was 7.1 × 10 ４ and Mw is 1.7 × 10 ５ It was.

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

[0429] Example 7 Synthesis of Polymer Compound P7 (Step 1) After creating an inert gas atmosphere in a reaction vessel, 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 the temperature was raised to 80°C. (Step 2) 20% by mass tetraethylammonium hydroxide (25 mL) was added dropwise to the reaction solution, and the mixture was 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 the mixture was refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25°C, and the aqueous layer was removed. The solution was then washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had previously been passed. The purified solution was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P7 (0.90 g). The Mn of polymer compound P7 was 5.3 × 10 ４ and Mw is 1.3 × 10 ５ It was.

[0430] Polymer compound P7 is a copolymer composed of structural units derived from compound 2D, structural units derived from compound PM3, and structural units derived from compound PM9 in a molar ratio of 50:47:3, according to the theoretical value calculated from the amounts of the raw materials charged.

[0431] Example 8 Synthesis of Polymer Compound P8 (Step 1) After creating an inert gas atmosphere in a reaction vessel, 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 added dropwise to the reaction solution, and the mixture was 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 the mixture was refluxed for 3 hours. (Step 4) Thereafter, the reaction solution was cooled to 25°C, and the aqueous layer was removed. The mixture was then washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The resulting organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The resulting solid was dissolved in toluene and purified by passing through an alumina column through which toluene had previously been passed. The purified solution was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P8 (0.52 g). The Mn of polymer compound P8 was 6.2 × 10 ４ and Mw is 1.3 × 10 ５ It was.

[0432] 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, according to the theoretical value calculated from the amounts of the charged raw materials.

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

[0434] 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, according to the theoretical value calculated from the amounts of the raw materials charged.

[0435] Example 10 Synthesis of Polymer Compound P10 (Step 1) After creating an inert gas atmosphere in a reaction vessel, Compound 3E (1.48 g), Compound PM2 (0.957 g), Compound PM10 (0.055 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (37.2 mg), toluene (20 mL), and tetrahydrofuran (20 mL) were added to the reaction vessel and heated to 80°C. (Step 2) A 30% by mass aqueous cesium carbonate solution (20 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours. (Step 3) After the reaction, phenylboronic acid (76.2 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (17.5 mg) were added thereto, and the mixture was refluxed for 3 hours. (Step 4) The reaction solution was then cooled to 25°C, the aqueous layer was removed, and the mixture was washed three times with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was then filtered and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had previously been passed. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was then filtered and dried to obtain polymer compound P10 (1.01 g). The Mn of polymer compound P10 was 1.1 × 10 ５ and Mw is 1.8 × 10 ５ It was.

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

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

[0438] Polymer compound P11 is a copolymer composed of structural units derived from compound PM3 and structural units derived from compound PM7 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the raw materials charged.

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

[0440] Polymer compound P12 is a copolymer composed of the sum of structural units derived from compound PM4 and structural units derived from compound PM5 and structural units derived from compound PM8 in a molar ratio of 95:5, according to the theoretical value calculated from the amounts of the charged raw materials.

[0441] Comparative Example 3: Synthesis of Polymer Compound P13 (Step 1) After creating an inert gas atmosphere in a reaction vessel, 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 heated 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) The reaction solution was then cooled to 25°C, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, twice with 10% by mass hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with ion-exchanged water. The obtained organic layer was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain a solid. The obtained solid was dissolved in toluene and purified by passing through an alumina column through which toluene had been passed in advance. The purified liquid was added dropwise to methanol and stirred, resulting in the formation of a precipitate, which was collected by filtration and dried to obtain polymer compound P13 (0.80 g). The Mn of polymer compound P13 was 3.5 × 10 ４ and Mw is 8.5 × 10 ４ It was.

[0442] Polymer compound P13 is a copolymer composed of structural units derived from compound PM3 and structural units derived from compound PM6 in a molar ratio of 50:50, according to the theoretical value calculated from the amounts of the raw materials charged.

[0443] <Measurement Example 1> Evaluation of Luminance Lifetime 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 to a synthetic quartz glass substrate by spin coating so that the thickness after drying would be 100 nm, and the substrate was heated at 150°C for 10 minutes in a nitrogen atmosphere (oxygen mass concentration 10 ppm or less, moisture mass concentration 10 ppm or less) to form an organic compound layer.

[0445] The substrate on which the organic compound layer was formed was placed in a deposition machine. －４ After reducing the pressure to 100 Pa or less, sodium fluoride was vapor-deposited to a thickness of about 30 nm. After the vapor deposition, the container was sealed using a glass substrate in a nitrogen atmosphere (oxygen mass concentration 10 ppm or less, moisture mass concentration 10 ppm or less), thereby preparing measurement sample 1.

[0446] The excitation light intensity of the excitation light source for the measurement sample 1 was determined by the above-mentioned method using formula (III). The luminance obtained when the measurement sample 1 was irradiated with the excitation light was 1398 cd / m ２ The measurement sample 1 was allowed to emit light continuously while the excitation light intensity was kept constant, and the time until the emission luminance reached 60% of the emission luminance at the start of the measurement (hereinafter referred to as "LT60") was measured. The results are shown in Table 2.

[0447] When the color conversion efficiency of the 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 lifespan Measurement sample 2 was prepared in the same manner as in Measurement Example 1, except that the polymer compound P2 was dissolved in xylene to a concentration of 2 mass % to prepare an ink, and the luminance lifespan was evaluated.

[0449] When the luminance of the measurement sample 2 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 2533 cd / m ２ Thereafter, the measurement sample 2 was allowed to continuously emit light while the excitation light intensity was kept constant, 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 life Measurement sample 3 was prepared in the same manner as in Measurement Example 1, except that polymer compound P3 was dissolved in xylene to a concentration of 2 mass % to prepare an ink, and the luminance life was evaluated.

[0451] When the luminance of the measurement sample 3 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 1639 cd / m ２ Thereafter, the measurement sample 3 was allowed to continuously emit light while maintaining the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

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

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

[0454] When the luminance of the measurement sample 4 was measured at the excitation light intensity at which the amount of photon absorption was constant with that of the measurement sample 1, it was found to be 2852 cd / m ２ Thereafter, the measurement sample 4 was allowed to continuously emit light while maintaining the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

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

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

[0457] When the luminance of the measurement sample 5 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 4370 cd / m ２ Thereafter, the measurement sample 5 was allowed to continuously emit light while maintaining the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

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

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

[0460] When the luminance of the measurement sample 6 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 7675 cd / m ２ Thereafter, the measurement sample 6 was allowed to continuously emit light while maintaining the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

[0461] When the color conversion efficiency of the 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 lifespan Measurement sample 7 was prepared in the same manner as in Measurement Example 1, except that the polymer compound P7 was dissolved in xylene to a concentration of 2 mass % to prepare an ink, and the luminance lifespan was evaluated.

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

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

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

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

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

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

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

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

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

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

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

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

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

[0476] When the luminance of the measurement sample 11 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 2900 cd / m ２ Thereafter, the measurement sample 11 was allowed to emit light continuously while the excitation light intensity was kept constant, and "LT60" was measured. The results are shown in Table 2.

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

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

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

[0480] When the luminance of the measurement sample 12 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 3554 cd / m ２ Thereafter, the measurement sample 12 was allowed to continuously emit light while maintaining the excitation light intensity constant, and "LT60" was measured. The results are shown in Table 2.

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

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

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

[0484] When the luminance of the measurement sample 13 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 3033 cd / m ２Thereafter, the measurement sample 13 was allowed to continuously emit light while maintaining 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] Measurement Example 14 Measurement of Luminance Lifetime A 2% by mass xylene solution of polymer compound P4 and 3% low molecular weight compound M1 was prepared in the same manner as in Measurement Example 11.

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

[0488] When the luminance of the measurement sample 14 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 4021 cd / m ２ Thereafter, the measurement sample 14 was allowed to continuously emit light while maintaining 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] Measurement Example 15 Measurement of Luminance Lifetime A 2.4 mass % xylene solution of polymer compound P1 to which 3% of low molecular compound M2 was added was prepared in the same manner as in Measurement Example 11.

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

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

[0493] When the color conversion efficiency of the 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% by mass xylene solution of high molecular compound P2 to which low molecular compound M2 was added at 3% was prepared in the same manner as in Measurement Example 11.

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

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

[0497] When the color conversion efficiency of the 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 of polymer compound P3 and 3% low molecular weight compound M2 was prepared in the same manner as in Measurement Example 11.

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

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

[0501] When the color conversion efficiency of the 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 of polymer compound P4 and 3% low molecular compound M2 was prepared in the same manner as in Measurement Example 11.

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

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

[0505] When the color conversion efficiency of the 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 lifespan Measurement sample 19 was prepared in the same manner as in Measurement Example 1, except that the low molecular weight compound M3 was dissolved in xylene to a concentration of 3.7 mass % to prepare an ink, and the luminance lifespan was evaluated.

[0507] When the luminance of the measurement sample 19 was measured at an excitation light intensity at which the amount of photon absorption was constant with that of the measurement sample 1, it was 699 cd / m ２ Thereafter, the measurement sample 19 was allowed to emit light continuously while the excitation light intensity was kept constant, and "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 Measurement of Luminance Lifetime A 3.5 mass % xylene solution of low molecular weight compound M3 to which 3% of low molecular weight compound M1 was added was prepared in the same manner as in Measurement Example 11.

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

[0511] When the luminance of the measurement sample 20 is measured at an 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 continuously emit light while maintaining the excitation light intensity constant, and "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 Measurement of Luminance Lifetime A 3% by mass xylene solution of low molecular weight compound M3 and 3% low molecular weight compound M2 was prepared in the same manner as in Measurement Example 11.

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

[0515] When the luminance of the measurement sample 21 is measured at an 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 Thereafter, the measurement sample 21 was allowed to emit light continuously while the excitation light intensity was kept constant, 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 Life A measurement sample 22 was prepared in the same manner as in Example Measurement Example 1, except that the polymer compound P11 was dissolved in xylene to a concentration of 1.6 mass % to prepare an ink, and the luminance life was evaluated.

[0518] When the luminance of the measurement sample 22 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 1758 cd / m ２ Thereafter, the measurement sample 22 was allowed to continuously emit light while maintaining the excitation light intensity constant, 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 life A measurement sample 23 was prepared in the same manner as in Example 1, except that the polymer compound P12 was dissolved in xylene to a concentration of 2.4 mass % to prepare an ink, and the luminance life was evaluated.

[0521] An attempt was made to measure the luminance of the measurement sample 23 at an excitation light intensity that would result in a constant amount of photon absorption compared to the measurement sample 1, but no luminescence was observed, and it was not possible to measure "LT60."

[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 life A measurement sample 24 was prepared in the same manner as in Example 1, except that the polymer compound P13 was dissolved in xylene to a concentration of 2.4 mass % to prepare an ink, and the luminance life was evaluated.

[0524] When the luminance of the measurement sample 24 is measured at an excitation light intensity at which the amount of photon absorption becomes constant with that of the measurement sample 1, it is 2425 cd / m ２ Thereafter, the measurement sample 24 was allowed to continuously 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 mass % xylene solution of polymer compound P13 and 3% low molecular weight compound M1 was prepared in the same manner as in Example 11.

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

[0528] When the luminance of the measurement sample 25 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 3176 cd / m ２ Thereafter, the measurement sample 25 was allowed to emit light continuously while the excitation light intensity was kept 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 mass % xylene solution of polymer compound P13 and 3% low molecular weight compound M2 was prepared in the same manner as in Example 11.

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

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

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

[0534]

[0535] These results show that the color conversion material containing compound (A) having a fused aromatic hydrocarbon skeleton with six or more fused rings has a longer luminance life than any of the color conversion materials containing fused heterocyclic compounds having fewer than six fused rings, fused heterocyclic compounds having six or more fused rings, and compounds having a fused aromatic hydrocarbon skeleton with fewer than six fused rings.

[0536] According to an embodiment of the present disclosure, a color conversion material having excellent luminance life 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. Furthermore, such a light-emitting device is suitable for a display device.

Claims

1. A color conversion material that converts incident light into light with a longer wavelength than the incident light, 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-changing 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).

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

6. The color-changing 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). [In the formula, a hydrogen atom directly bonded to a carbon atom constituting a fused ring may be substituted with a substituent.] 7. The color conversion material according to claim 5, which contains one or more compounds (B) selected from the group consisting of the following low molecular weight compound (B), the following polymer compound (AB) and the following polymer compound (B), and satisfies condition III. Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound that satisfies the following condition I. Polymer compound (AB): The polymer compound (AB) is a polymer compound that includes 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) that includes a structural unit (B) that satisfies the following condition II (however, excluding those that fall under the polymer compound (A)). (Condition I) The energy level of the lowest singlet excited state of a compound having a hydrogen atom bonded to a bond of the structural unit (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 a compound having a hydrogen atom bonded to a bond of the structural unit (A)>the energy level of the lowest singlet excited state of a compound having a hydrogen atom bonded to a bond of the structural unit (B). (Condition III) 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 weight compound (B) per unit mass].

8. The color conversion material according to claim 7, wherein the structural unit (B) is a structural unit derived from an organoboron compound, and the low molecular weight compound (B) is an organoboron compound.

9. The color conversion material according to claim 8, wherein the organic boron compound is a low molecular weight compound represented by any one of formulas (7) to (9). [In the formula, ring A, ring B and ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. 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 a substituent. Y １ represents N-Ry, a sulfur atom or a selenium atom. 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 a substituent. When a plurality of Ry's are present, they may be the same or different. Ry may be bonded to the A ring, the B ring, or the C ring directly or via a linking group. X represents a C-R ７ or N. １ ~R ９ R 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 a substituent. R １ ~R ９ Adjacent groups may be bonded to each other directly or via a linking group to form a ring.

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

11. The color conversion material according to claim 10, comprising one or more compounds (B) selected from the group consisting of the following low molecular weight compounds (B) and the following polymer compounds (B), and satisfying condition III. Low molecular weight compound (B): The low molecular weight compound (B) is a low molecular weight compound that satisfies the following condition I. Polymer compound (B): The polymer compound (B) is a polymer compound containing a structural unit (B) that satisfies the following condition II. (Condition I) Energy level of the lowest singlet excited state of the low molecular weight compound (A) > Energy level of the lowest singlet excited state of the low molecular weight compound (B) (Condition II) Energy level of the lowest singlet excited state of the low molecular weight compound (A) > Energy level of the lowest singlet excited state of a compound in which a hydrogen atom is bonded to a bond of the structural unit (B) (Condition III) Molar content of the low molecular weight compound (A) per unit mass > [molar content of the structural unit (B) per unit mass + molar content of the low molecular weight compound (B) per unit mass] 12. The color conversion material according to claim 11, wherein the structural unit (B) is a structural unit derived from an organoboron compound, and the low molecular weight compound (B) is an organoboron compound.

13. The color conversion material according to claim 12, wherein the organic boron compound is a low molecular weight compound represented by any one of formulas (7) to (9). [In the formula, ring A, ring B and ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. 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 a substituent. Y １ represents N-Ry, a sulfur atom or a selenium atom. 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 a substituent. When a plurality of Ry's are present, they may be the same or different. Ry may be bonded to the A ring, the B ring, or the C ring directly or via a linking group. X represents a C-R ７ or N. １ ~R ９ R 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 a substituent. R １ ~R ９ Adjacent groups may be bonded to each other directly or via a linking group to form a ring.

14. An ink comprising 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 with a longer wavelength than the incident light, comprising the color conversion material according to any one of claims 1 to 13.

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

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

Images