WO2022255428A1 - Composé aromatique, élément électroluminescent organique, composition et procédé de production d'élément électroluminescent organique - Google Patents

Composé aromatique, élément électroluminescent organique, composition et procédé de production d'élément électroluminescent organique Download PDF

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WO2022255428A1
WO2022255428A1 PCT/JP2022/022397 JP2022022397W WO2022255428A1 WO 2022255428 A1 WO2022255428 A1 WO 2022255428A1 JP 2022022397 W JP2022022397 W JP 2022022397W WO 2022255428 A1 WO2022255428 A1 WO 2022255428A1
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group
ring
optionally substituted
carbon atoms
formula
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PCT/JP2022/022397
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Japanese (ja)
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司 長谷川
一毅 岡部
延軍 李
大輔 弘
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三菱ケミカル株式会社
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Priority to KR1020237041516A priority Critical patent/KR20240016969A/ko
Priority to JP2023525903A priority patent/JPWO2022255428A1/ja
Priority to CN202280039377.0A priority patent/CN117480156A/zh
Publication of WO2022255428A1 publication Critical patent/WO2022255428A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • the present invention provides an aromatic compound that can be used in an organic electroluminescent device (hereinafter sometimes referred to as "OLED” or “device”), an organic electroluminescent device having the compound, and the organic electroluminescent device.
  • OLED organic electroluminescent device
  • the present invention relates to a display device and a lighting device, a composition containing the compound and the solvent, a method for forming a thin film, and a method for manufacturing an organic electroluminescent device.
  • OLED organic electroluminescent device
  • An organic electroluminescent device typically has a hole-injection layer, a hole-transport layer, an organic light-emitting layer, an electron-transport layer, etc. between an anode and a cathode. Materials suitable for each of these layers are being developed, and the development of red, green, and blue emission colors is progressing.
  • coating-type OLEDs which are more efficient in material utilization than conventional evaporation-type OLEDs and can reduce manufacturing costs.
  • Patent Document 1 reports an OLED material using an aromatic compound containing a triazine structure, such as the following compound (C-1), as a charge transport material for a phosphorescent compound.
  • Patent Document 2 reports an OLED material using an aromatic compound containing a triazine and a spirobifluorene structure, such as compounds (C-2) to (C-4) below, as a material for the life improving layer.
  • the above compound (C-1) has a glass transition temperature as low as 93°C and does not have sufficient heat resistance.
  • the above compounds (C-2) to (C-4) are used as the charge transport material of the light-emitting layer, the electron mobility is insufficient and the device efficiency and device life are low.
  • the durability to alcohol solvents for laminating a thin film by a wet film forming method using an alcohol solvent on the thin film formed from the above compounds (C-1) to (C-4) is not sufficient. .
  • the present invention has been made in view of the above-mentioned conventional circumstances, and provides an aromatic compound having excellent heat resistance, excellent solubility, excellent electron transport properties, and excellent durability to alcohol solvents in thin films.
  • the challenge is to
  • the present invention also provides an organic electroluminescent device containing the compound, a display device and a lighting device comprising the organic electroluminescent device, a composition containing the compound and a solvent, a method for forming a thin film, and a method for manufacturing an organic electroluminescent device.
  • the task is to provide
  • alcohol solvent may be referred to as “alcohol-based solvent” or “alcohol-based solvent”.
  • the gist of the present invention is as follows ⁇ 1> to ⁇ 21>.
  • G 1 and G 2 each independently represent formula (3) below, and G 3 represents formula (4) below.
  • L 2 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked
  • Ar 2 is an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted monovalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted monovalent aromatic hydrocarbon groups having 60 or less carbon atoms and optionally substituted monovalent heteroaromatic groups having 60 or less carbon atoms is a group to which the group is linked
  • a2 represents an integer of 1 to 5;
  • L 3 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked, a3 represents an integer of 1 to 5; ) ⁇ 2> The aromatic compound according to ⁇ 1>, wherein G 1 is represented by the following formula (2).
  • L 1 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked
  • Ar 1 is an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted monovalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted monovalent aromatic hydrocarbon groups having 60 or less carbon atoms and optionally substituted monovalent heteroaromatic groups having 60 or less carbon atoms is a group to which the group is linked
  • a 1 represents an integer of 0 to 5;
  • ⁇ 4> The aromatic compound according to ⁇ 2> or ⁇ 3>, wherein L 1 to L 3 are each independently a 1,3-phenylene group or a 1,4-phenylene group.
  • ⁇ 5> The aromatic compound according to any one of ⁇ 1> to ⁇ 4>, which has a molecular weight of 1200 or more.
  • ⁇ 6> An organic electroluminescence device having an anode and a cathode on a substrate and an organic layer between the anode and the cathode, The organic layer has a layer containing an organic electroluminescence device material, An organic electroluminescent device, wherein the organic electroluminescent device material is the aromatic compound according to any one of ⁇ 1> to ⁇ 5>.
  • ⁇ 7> The organic electroluminescent device according to ⁇ 6>, wherein the layer containing the organic electroluminescent device material is a light-emitting layer.
  • a display device comprising the organic electroluminescent element according to ⁇ 6> or ⁇ 7>.
  • a lighting device comprising the organic electroluminescent element according to ⁇ 6> or ⁇ 7>.
  • composition for an organic electroluminescence device comprising the aromatic compound according to any one of ⁇ 1> to ⁇ 5> and a solvent.
  • composition for an organic electroluminescence device according to ⁇ 10> further comprising a phosphorescent material and a charge transport material.
  • the charge-transporting material is a compound represented by the following formula (240) or a compound represented by the following formula (260).
  • Ar 611 and Ar 612 each independently represent an optionally substituted monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • R 611 and R 612 are each independently a deuterium atom, a halogen atom, or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • G represents a single bond or an optionally substituted divalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • n 611 and n 612 are each independently an integer of 0-4.
  • each of Ar 21 to Ar 35 is independently a hydrogen atom, an optionally substituted phenyl group or an optionally substituted phenyl group, 2 to 10, unbranched or It represents a branched and linked monovalent group.
  • each of Ar 611 and Ar 612 in the formula (240) is independently a monovalent group in which a plurality of optionally substituted benzene rings are bonded in a chain or branched manner A composition for an electroluminescence device.
  • R 611 and R 612 in formula (240) are each independently an optionally substituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms.
  • a composition for an organic electroluminescence device ⁇ 15> The composition for an organic electroluminescence element according to any one of ⁇ 12> to ⁇ 14>, wherein n 611 and n 612 in formula (240) are each independently 0 or 1.
  • Ar 21 , Ar 25 , Ar 26 , Ar 30 , Ar 31 and Ar 35 are hydrogen atoms
  • Ar 22 to Ar 24 , Ar 27 to Ar 29 , and Ar 32 to Ar 34 are hydrogen atoms, phenyl groups, or structures selected from the following formulas (261-1) to (261-9).
  • the composition for an organic electroluminescence element according to ⁇ 12>, wherein these structures may have the substituents.
  • a method for forming a thin film comprising a step of forming a film from the composition for an organic electroluminescent device according to any one of ⁇ 10> to ⁇ 16> by a wet film-forming method.
  • a method for producing an organic electroluminescence device having an anode and a cathode on a substrate and an organic layer between the anode and the cathode comprising: A method for producing an organic electroluminescent device, comprising forming the organic layer by a wet film-forming method using the composition for an organic electroluminescent device according to any one of ⁇ 10> to ⁇ 16>.
  • the solvent contained in the electron transport layer composition is an alcohol solvent.
  • an aromatic compound having excellent heat resistance, excellent solubility, excellent electron transport properties, and excellent durability to alcohol solvents in thin films.
  • an organic electroluminescent device having the compound, a display device and a lighting device having the organic electroluminescent device, a composition containing the compound and a solvent, a method for forming a thin film, and a method for manufacturing an organic electroluminescent device are provided. can provide.
  • FIG. 1 is a cross-sectional view schematically showing an example of the structure of the organic electroluminescence device of the present invention.
  • the aromatic compound of the present invention is represented by the following formula (1).
  • G 1 and G 2 each independently represent formula (3) below, and G 3 represents formula (4) below.
  • L 2 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked
  • Ar 2 is an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted monovalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted monovalent aromatic hydrocarbon groups having 60 or less carbon atoms and optionally substituted monovalent heteroaromatic groups having 60 or less carbon atoms is a group to which the group is linked
  • a2 represents an integer of 1 to 5;
  • L 3 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked, a3 represents an integer of 1 to 5; )
  • G1 is preferably represented by the following formula (2).
  • L 1 is an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted divalent C 60 or less aromatic hydrocarbon groups and optionally substituted divalent C 60 or less heteroaromatic groups is a group to which the group is linked
  • Ar 1 is an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted monovalent heteroaromatic group having 60 or less carbon atoms, or A plurality of groups selected from optionally substituted monovalent aromatic hydrocarbon groups having 60 or less carbon atoms and optionally substituted monovalent heteroaromatic groups having 60 or less carbon atoms is a group to which the group is linked
  • a 1 represents an integer of 0 to 5;
  • the aromatic compound of the present invention has a spirobifluorene structure represented by formula (4), and therefore has a high glass transition temperature.
  • the aromatic compound of the present invention since the triazine skeleton and the spirobifluorene structure are bonded via a structure larger than that of biphenyl, steric hindrance due to the spirobifluorene structure can be suppressed and the electron transport property is high.
  • the aromatic compound of the present invention has a biphenyl group to which the spirobifluorene structure represented by formula (4) is bonded at the meta position, and thus has high solubility. Since the compound of the present invention has a large molecular weight and at least one spirobifluorene structure, it has excellent resistance to alcohol solvents after film formation.
  • the LUMO orbital is easily localized in the triazine structure represented by formula (1), and the HOMO orbital is localized in the spirobifluorene structure represented by formula (3). It is easy to be tarnished and the durability can be improved.
  • aromatic compound of the present invention it is possible to easily provide an organic electroluminescence device that has excellent driving stability and can be driven at a low driving voltage and with high efficiency.
  • the organic electroluminescent device of the present invention containing the aromatic compound of the present invention has excellent electrochemical stability, low driving voltage and high efficiency. Therefore, the organic electroluminescence device of the present invention can be used as a flat panel display (for example, an OA computer display or a wall-mounted TV), an in-vehicle display device, a mobile phone display, or a light source (for example, a copier (light sources for liquid crystal displays and instruments, backlight sources for instruments), display boards, and indicator lamps, and their technical value is great.
  • a flat panel display for example, an OA computer display or a wall-mounted TV
  • an in-vehicle display device for example, a mobile phone display, or a light source (for example, a copier (light sources for liquid crystal displays and instruments, backlight sources for instruments), display boards, and indicator lamps, and their technical value is great.
  • Ar 1 and Ar 2 each independently represent an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms and an optionally substituted monovalent carbon number of 60 or less or an optionally substituted monovalent aromatic hydrocarbon group having 60 or less carbon atoms and an optionally substituted monovalent heteroaromatic group having 60 or less carbon atoms represents a group in which a plurality of groups selected from groups are linked;
  • Examples of monovalent aromatic hydrocarbon groups having 60 or less carbon atoms include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, tetraphenylene ring, chrysene ring, pyrene ring, benzanthracene ring, perylene ring, biphenyl ring, or a monovalent group of a terphenyl ring.
  • Examples of monovalent heteroaromatic groups having 60 or less carbon atoms include furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring , pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quino
  • a phenyl group a group in which a plurality of phenyl groups are linked, or a naphthyl group, and more preferably a phenyl group or a group in which a plurality of phenyl groups are linked.
  • L 1 , L 2 , L 3 > L 1 , L 2 and L 3 are each independently an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms, an optionally substituted divalent carbon
  • a heteroaromatic group having a number of 60 or less, or an optionally substituted divalent aromatic hydrocarbon group having 60 or less carbon atoms and an optionally substituted divalent carbon number of 60 or less represents a group in which a plurality of groups selected from heteroaromatic groups are linked.
  • divalent aromatic hydrocarbon groups having 60 or less carbon atoms examples include divalent benzene ring, naphthalene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene ring, benzanthracene ring, or perylene ring. group.
  • divalent heteroaromatic groups having 60 or less carbon atoms include furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring , pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline
  • a phenyl group a group in which a plurality of phenyl groups are linked, or a naphthyl group, and more preferably a phenyl group or a group in which a plurality of phenyl groups are linked.
  • a 1,3-phenylene group or a 1,4-phenylene group is more preferable.
  • a 1 represents an integer of 0 to 5
  • a 2 and a 3 each independently represent an integer of 1 to 5
  • a1 and a3 are preferably 3 or less, more preferably 2 or less, particularly preferably 1
  • a2 is preferably 4 or less, further preferably 3 or less.
  • a plurality of L 1 to L 3 may be the same or different.
  • At least one of (L 1 ) a1 , (L 2 ) a2 and (L 3 ) a3 is a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), from the viewpoint of compound solubility and durability. ) and at least one partial structure selected from the partial structure represented by the following formula (13).
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • At least one of (L 1 ) a1 , (L 2 ) a2 and (L 3 ) a3 has at least the partial structure represented by formula (11) or the partial structure represented by formula (12). have. More preferably, each of (L 1 ) a1 , (L 2 ) a2 and (L 3 ) a3 has at least the partial structure represented by formula (11) or the partial structure represented by formula (12). Particularly preferably, (L 2 ) a2 has a partial structure represented by formula (11) and a partial structure represented by formula (12).
  • Formula (12) is preferably the following formula (12-2).
  • Formula (12) is more preferably formula (12-3) below.
  • the partial structure represented by formula (11) and the partial structure represented by formula (12) it is more preferable to have at least one partial structure selected from the following formulas (14) to (18), which is a structure containing a plurality of structures selected from:
  • the structure containing a plurality of structures selected from the partial structure represented by the formula (11) and the partial structure represented by the formula (12) is, for example, the formula (14), such as the following formula (14a), the formula It is a partial structure having one partial structure represented by (11) and two partial structures represented by formula (12).
  • At least one of (L 1 ) a1 , (L 2 ) a2 and (L 3 ) a3 is at least the partial structure represented by formula (14) or the moiety represented by formula (15) have a structure.
  • Formula (14) is preferably the following formula (14-2).
  • Formula (14) is more preferably formula (14-3) below.
  • Formula (15) is preferably the following formula (15-2).
  • Formula (15) is more preferably formula (15-3) below.
  • Formula (17) is preferably the following formula (17-2).
  • Formula (18) is preferably the following formula (18-2).
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • formulas (14) to (20) formulas (14-3) and (15-3) are preferred, and formula (14-3) is more preferred.
  • Substituent group Z includes an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, and a cyano group. , an aralkyl group, an aromatic hydrocarbon group, or a heteroaromatic group.
  • the alkyl group includes, for example, a methyl group, an ethyl group, a branched, straight-chain or cyclic propyl group, a branched, straight-chain or cyclic butyl group, a branched, straight-chain or cyclic pentyl group, a branched, straight-chain or cyclic A hexyl group, a branched, straight-chain or cyclic octyl group, a branched, straight-chain or cyclic nonyl group, a branched, straight-chain or cyclic dodecyl group, etc., usually having 1 or more carbon atoms, preferably 4 or more, and usually Linear, branched or cyclic alkyl groups with 24 or less, preferably 10 or less are mentioned.
  • a methyl group, an ethyl group, a branched, linear or cyclic propyl group, and a branched, linear or cyclic butyl group are preferred, and a branched propyl group is particularly preferred.
  • alkenyl groups include alkenyl groups having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less carbon atoms such as vinyl groups.
  • alkynyl groups include alkynyl groups having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less carbon atoms such as ethynyl groups.
  • alkoxy groups include alkoxy groups having usually 1 or more carbon atoms and usually 24 or less, preferably 12 or less carbon atoms such as methoxy and ethoxy groups.
  • the aryloxy group includes, for example, an aryloxy group or heteroaryl having usually 4 or more, preferably 5 or more carbon atoms and usually 36 or less, preferably 24 or less, such as phenoxy group, naphthoxy group, pyridyloxy group, etc.
  • An oxy group can be mentioned.
  • the alkoxycarbonyl group includes, for example, an alkoxycarbonyl group having usually 2 or more carbon atoms, usually 24 or less, preferably 12 or less, such as a methoxycarbonyl group and an ethoxycarbonyl group.
  • the acyl group includes, for example, an acyl group having usually 2 or more carbon atoms, usually 24 or less, preferably 12 or less, such as an acetyl group and a benzoyl group.
  • halogen atoms include halogen atoms such as fluorine atoms and chlorine atoms.
  • the haloalkyl group includes, for example, a haloalkyl group having usually 1 or more carbon atoms, usually 12 or less, preferably 6 or less, such as a trifluoromethyl group.
  • the alkylthio group includes, for example, an alkylthio group having usually 1 or more carbon atoms, usually 24 or less, preferably 12 or less, such as a methylthio group or an ethylthio group.
  • arylthio group examples include arylthio groups having usually 4 or more, preferably 5 or more carbon atoms and usually 36 or less, preferably 24 or less carbon atoms such as phenylthio, naphthylthio, and pyridylthio groups.
  • the silyl group includes, for example, a silyl group having usually 2 or more, preferably 3 or more carbon atoms, and usually 36 or less, preferably 24 or less carbon atoms such as trimethylsilyl group and triphenylsilyl group.
  • Siloxy groups include, for example, siloxy groups having usually 2 or more, preferably 3 or more carbon atoms and usually 36 or less, preferably 24 or less carbon atoms such as trimethylsiloxy and triphenylsiloxy groups.
  • aralkyl groups include benzyl, 2-phenylethyl, 2-phenylpropyl-2-yl, 2-phenylbutyl-2-yl, 3-phenylpentyl-3-yl, 3-phenyl- 1-propyl group, 4-phenyl-1-butyl group, 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group, 7-phenyl-1-heptyl group, 8-phenyl-1-octyl group, etc. and an aralkyl group having usually 7 or more, preferably 9 or more carbon atoms and usually 30 or less, preferably 18 or less, more preferably 10 or less carbon atoms.
  • aromatic hydrocarbon group examples include, for example, benzene ring, naphthalene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene ring, benzanthracene ring, or perylene ring.
  • An aromatic hydrocarbon group having a number of 30 or less, preferably 18 or less, more preferably 10 or less can be mentioned.
  • heteroaromatic groups include furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrolo imidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, A pyrimidine ring, a triazine ring, a quinoline ring, an iso
  • an alkyl group, an alkoxy group, an aralkyl group and an aromatic hydrocarbon group are preferable, and an alkyl group having 10 or less carbon atoms, an aralkyl group having 30 or less carbon atoms, and an aralkyl group having 30 or less carbon atoms are more preferable.
  • each substituent in the substituent group Z may further have a substituent.
  • additional substituents the same substituents as those described above (substituent group Z) can be used.
  • the substituents in the substituent group Z preferably have no further substituents.
  • the molecular weight of the aromatic compound of the present invention is preferably 1,000 or more, more preferably 1,100 or more, most preferably 1,200 or more, and preferably 5,000 or less, more preferably 4,000 or less, and particularly preferably 3,000 or less. Yes, and most preferably 2000 or less.
  • the aromatic compound of the present invention can be produced, for example, according to the method described in Examples.
  • the aromatic compound of the present invention is preferably used as an organic electroluminescent element material for an organic layer of an organic electroluminescent element, and the organic layer is preferably a light-emitting layer.
  • An organic electroluminescent device can have, for example, an anode and a cathode on a substrate, and an organic layer between the anode and the cathode.
  • the aromatic compound of the present invention is used in the light-emitting layer, it is preferably used as a host material for the light-emitting layer.
  • the organic layer containing the aromatic compound of the present invention may be formed by a vapor deposition method or by a wet film formation method.
  • the aromatic compound of the present invention when used in the organic layer of an organic electroluminescent device, the aromatic compound of the present invention is also referred to as a material for organic electroluminescent devices.
  • composition When the organic layer containing the aromatic compound of the present invention is formed by a wet film formation method, at least the aromatic compound represented by the formula (1) and a solvent (hereinafter sometimes referred to as "organic solvent” ) is wet film-formed. That is, the composition of the present invention contains at least the aromatic compound represented by formula (1) and an organic solvent.
  • composition of the present invention is suitably used as a composition for organic electroluminescent elements for forming organic electroluminescent elements.
  • the composition of the present invention preferably further contains a luminescent material, and is suitably used as a composition for forming a luminescent layer of an organic electroluminescent device.
  • a luminescent material a phosphorescent luminescent material is preferable.
  • the composition of the present invention preferably further contains a light-emitting material and a charge-transporting material, and is suitably used as a composition for forming a light-emitting layer of an organic electroluminescence device.
  • a luminescent material a phosphorescent luminescent material is preferable.
  • Organic solvent contained in the composition of the present invention is a volatile liquid component used for forming the layer containing the aromatic compound of the present invention by wet film formation.
  • the organic solvent is not particularly limited as long as it is an organic solvent in which the aromatic compound of the present invention, which is the solute, and the luminescent material described later are well dissolved.
  • Preferred organic solvents include, for example, alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin and bicyclohexane; aromatic hydrocarbons such as toluene, xylene, mesitylene, phenylcyclohexane, tetralin and methylnaphthalene; Halogenated aromatic hydrocarbons such as chlorobenzene and trichlorobenzene; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3 - aromatic ethers such as dimethylanisole, 2,4-dimethylanisole and diphenyl ether; aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, prop
  • alkanes, aromatic hydrocarbons, aromatic ethers, and aromatic esters are preferred, and aromatic hydrocarbons, aromatic ethers, and aromatic esters are more preferred. , aromatic hydrocarbons and aromatic esters are particularly preferred.
  • One type of these organic solvents may be used alone, or two or more types may be used in any combination and ratio.
  • the boiling point of the organic solvent used is usually 80°C or higher, preferably 100°C or higher, more preferably 120°C or higher, and usually 380°C or lower, preferably 350°C or lower, more preferably 330°C or lower. If the boiling point of the organic solvent is below this range, the film formation stability may decrease due to evaporation of the solvent from the composition during wet film formation. If the boiling point of the organic solvent exceeds this range, there is a possibility that the film formation stability will decrease due to the residual solvent after film formation during wet film formation.
  • a uniform coating film can be produced. If the number of organic solvents having a boiling point of 150° C. or higher is less than one, it is considered that a uniform film may not be formed during coating.
  • the composition of the present invention is preferably a composition for forming a light-emitting layer, and in this case, it preferably further contains a light-emitting material.
  • a luminescent material refers to a component that mainly emits light in the composition for an organic electroluminescent element of the present invention, and corresponds to a dopant component in an organic electroluminescent device.
  • the light-emitting material a known material can be applied, and a fluorescent light-emitting material or a phosphorescent light-emitting material can be used singly or in combination, but from the viewpoint of internal quantum efficiency, phosphorescent light-emitting materials are preferable.
  • phosphorescent material is a material that emits light from an excited triplet state.
  • metal complex compounds containing Ir, Pt, Eu, etc. are typical examples, and materials containing metal complexes are preferable as the structure of the material.
  • the long-period periodic table (unless otherwise specified, the long-period periodic table ) include Werner-type complexes or organometallic complex compounds containing a metal selected from Groups 7 to 11 as a central metal.
  • a compound represented by the following formula (201) or a compound represented by the following formula (205) is preferable, and a compound represented by the following formula (201) is more preferable.
  • M is a metal selected from Groups 7 to 11 of the periodic table, such as ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, gold, and europium.
  • Ring A1 represents an optionally substituted aromatic hydrocarbon ring structure or an optionally substituted aromatic heterocyclic ring structure.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • R 201 and R 202 each independently represent a structure represented by formula (202) above, and "*" represents bonding to ring A1 or ring A2.
  • R 201 and R 202 may be the same or different, and when multiple R 201 and R 202 are present, they may be the same or different.
  • Ar 201 and Ar 203 each independently represent an optionally substituted aromatic hydrocarbon ring structure or an optionally substituted aromatic heterocyclic ring structure.
  • Ar 202 is an optionally substituted aromatic hydrocarbon ring structure, an optionally substituted aromatic heterocyclic ring structure, or an optionally substituted aliphatic hydrocarbon structure represents
  • the substituents bonded to ring A1, the substituents bonded to ring A2, or the substituents bonded to ring A1 and the substituents bonded to ring A2 may be bonded to each other to form a ring.
  • B 201 -L 200 -B 202 represents an anionic bidentate ligand.
  • B 201 and B 202 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • L 200 represents a single bond or an atomic group forming a bidentate ligand together with B 201 and B 202 .
  • B 201 -L 200 -B 202 When there are multiple groups of B 201 -L 200 -B 202 , they may be the same or different.
  • i1 and i2 each independently represent an integer of 0 or more and 12 or less.
  • i3 is an integer greater than or equal to 0 up to the number that can be substituted for Ar 202 .
  • j is an integer greater than or equal to 0 up to the number that can be substituted for Ar 201 .
  • k1 and k2 are each independently an integer of 0 or more, with the upper limit being the number that can be substituted on ring A1 and ring A2.
  • m is an integer of 1-3.
  • the aromatic hydrocarbon ring for ring A1 is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and specifically includes a benzene ring, naphthalene ring, anthracene ring, triphenylyl ring, acenaphthene ring, fluoranthene ring, A fluorene ring is preferred.
  • the aromatic heterocyclic ring in ring A1 is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing any one of a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, more preferably a furan ring or a benzofuran ring. , thiophene ring, and benzothiophene ring.
  • the ring A1 is more preferably a benzene ring, a naphthalene ring or a fluorene ring, particularly preferably a benzene ring or a fluorene ring, most preferably a benzene ring.
  • the aromatic heterocyclic ring in ring A2 is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing either a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, oxazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, Naphthyridine ring, phenanthridine ring, More preferred are pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, benzothiazole ring, benzoxazole ring, quinoline ring, isoquinoline ring, quinoxaline ring and quinazoline ring,
  • a preferred combination of ring A1 and ring A2 is represented by (ring A1-ring A2), (benzene ring-pyridine ring), (benzene ring-quinoline ring), (benzene ring-quinoxaline ring), (benzene ring-quinazoline ring), (benzene ring-imidazole ring), (benzene ring-benzothiazole ring) .
  • the substituents that ring A1 and ring A2 may have may be arbitrarily selected, but are preferably one or more substituents selected from the group S of substituents described below.
  • the aromatic hydrocarbon ring structure is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms, Specifically, benzene ring, naphthalene ring, anthracene ring, triphenylyl ring, acenaphthene ring, fluoranthene ring, and fluorene ring are preferred. More preferably, a benzene ring, a naphthalene ring, or a fluorene ring, A benzene ring is most preferred.
  • Ar 201 , Ar 202 and Ar 203 is a fluorene ring optionally having a substituent
  • the 9- and 9′-positions of the fluorene ring have a substituent or are bonded to the adjacent structure. preferably.
  • Ar 201 , Ar 202 and Ar 203 is a benzene ring optionally having a substituent
  • at least one benzene ring is preferably bonded to the adjacent structure at the ortho- or meta-position.
  • at least one benzene ring is attached to the adjacent structure at the meta position.
  • the aromatic heterocyclic ring structure is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing either a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, oxazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, phenanthridine ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, More preferred are pyridine ring, pyrimidine ring, triazine ring, carbazole
  • Ar 201 , Ar 202 and Ar 203 is a carbazole ring optionally having a substituent
  • the N-position of the carbazole ring may have a substituent or be bonded to an adjacent structure. preferable.
  • the aliphatic hydrocarbon structure is an aliphatic hydrocarbon structure having a linear, branched, or cyclic structure, preferably an aliphatic hydrocarbon having 1 to 24 carbon atoms, more preferably aliphatic hydrocarbons having 1 to 12 carbon atoms, More preferred are aliphatic hydrocarbons having 1 to 8 carbon atoms.
  • i1 and i2 are each independently preferably an integer of 1-12, more preferably an integer of 1-8, more preferably an integer of 1-6. Within this range, improved solubility and improved charge transport properties can be expected.
  • i3 preferably represents an integer of 0 to 5, more preferably an integer of 0 to 2, more preferably 0 or 1.
  • j preferably represents an integer of 0 to 2, more preferably 0 or 1.
  • k1 and k2 preferably represent integers of 0 to 3, more preferably integers of 1 to 3, more preferably 1 or 2, and particularly preferably 1.
  • the substituents that Ar 201 , Ar 202 and Ar 203 may have can be arbitrarily selected, but are preferably one or more substituents selected from the group S of substituents described later, more preferably hydrogen It is an atom, an alkyl group or an aryl group, particularly preferably a hydrogen atom or an alkyl group, most preferably unsubstituted (hydrogen atom).
  • the substituent is preferably a group selected from the following substituent group S.
  • An alkoxy group preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 12 carbon atoms, and still more preferably an alkoxy group having 1 to 6 carbon atoms.
  • an aryloxy group preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 14 carbon atoms, still more preferably an aryloxy group having 6 to 12 carbon atoms, particularly preferably an aryloxy group having 6 carbon atoms; aryloxy group.
  • a heteroaryloxy group preferably a heteroaryloxy group having 3 to 20 carbon atoms, more preferably a heteroaryloxy group having 3 to 12 carbon atoms.
  • an alkylamino group preferably an alkylamino group having 1 to 20 carbon atoms, more preferably an alkylamino group having 1 to 12 carbon atoms;
  • An arylamino group preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group having 6 to 24 carbon atoms.
  • An aralkyl group preferably an aralkyl group having 7 to 40 carbon atoms, more preferably an aralkyl group having 7 to 18 carbon atoms, and still more preferably an aralkyl group having 7 to 12 carbon atoms.
  • a heteroaralkyl group preferably a heteroaralkyl group having 7 to 40 carbon atoms, more preferably a heteroaralkyl group having 7 to 18 carbon atoms.
  • an alkenyl group preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 12 carbon atoms, still more preferably an alkenyl group having 2 to 8 carbon atoms, particularly preferably an alkenyl group having 2 to 6 carbon atoms .
  • An alkynyl group preferably an alkynyl group having 2 to 20 carbon atoms, more preferably an alkynyl group having 2 to 12 carbon atoms.
  • an aryl group preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms, still more preferably an aryl group having 6 to 18 carbon atoms, particularly preferably an aryl group having 6 to 14 carbon atoms .
  • a heteroaryl group preferably a heteroaryl group having 3 to 30 carbon atoms, more preferably a heteroaryl group having 3 to 24 carbon atoms, still more preferably a heteroaryl group having 3 to 18 carbon atoms, particularly preferably 3 to 3 carbon atoms 14 heteroaryl groups.
  • alkylsilyl group preferably an alkylsilyl group having 1 to 20 carbon atoms, more preferably an alkylsilyl group having 1 to 12 carbon atoms.
  • An arylsilyl group preferably an arylsilyl group in which the aryl group has 6 to 20 carbon atoms, more preferably an arylsilyl group in which the aryl group has 6 to 14 carbon atoms.
  • an alkylcarbonyl group preferably an alkylcarbonyl group having 2 to 20 carbon atoms
  • - an arylcarbonyl group preferably an arylcarbonyl group having 7 to 20 carbon atoms
  • one or more hydrogen atoms may be replaced with fluorine atoms, or one or more hydrogen atoms may be replaced with deuterium atoms.
  • aryl is an aromatic hydrocarbon and heteroaryl is an aromatic heterocycle.
  • an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and at least one hydrogen atom of these groups is fluorine.
  • substituent group S may further have a substituent selected from the substituent group S as a substituent.
  • Preferred groups, more preferred groups, further preferred groups, particularly preferred groups, and most preferred groups of the substituents which may be present are the same as the preferred groups in Substituent Group S and the like.
  • Ar 201 is a benzene ring structure, i1 is 1 to 6, and at least one of the benzene rings is bonded to the adjacent structure at the ortho- or meta-position. This structure is expected to improve the solubility and the charge transport property.
  • Ar 201 is an aromatic hydrocarbon structure or an aromatic heterocyclic structure, i1 is 1 to 6, Ar 202 is an aliphatic hydrocarbon structure, i2 is 1-12, preferably 3-8, Ar 203 is a benzene ring structure and i3 is 0 or 1.
  • Ar 201 is preferably the above aromatic hydrocarbon structure, more preferably a structure in which 1 to 5 benzene rings are linked, and more preferably one benzene ring. This structure is expected to improve the solubility and the charge transport property.
  • Ar 201 and Ar 202 are benzene ring structures
  • Ar 203 is a biphenyl or terphenyl structure
  • i1 and i2 are 1 to 6
  • i3 is 2
  • j is 2. This structure is expected to improve the solubility and the charge transport property.
  • R 211 , R 212 and R 213 represent substituents.
  • the substituent is not particularly limited, it is preferably a group selected from the substituent group S described above.
  • Ring B3 represents an aromatic heterocyclic structure containing a nitrogen atom, which may have a substituent.
  • Ring B3 is preferably a pyridine ring.
  • the substituent that ring B3 may have is not particularly limited, it is preferably a group selected from the substituent group S described above.
  • phosphorescent material represented by formula (201) is not particularly limited, specific examples include the following structures.
  • Me means a methyl group and Ph means a phenyl group.
  • M2 represents a metal and T represents a carbon or nitrogen atom.
  • R 92 to R 95 each independently represent a substituent. However, when T is a nitrogen atom, R94 and R95 do not exist.
  • M2 represents a metal.
  • Specific examples include metals selected from groups 7 to 11 of the periodic table. Among them, ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold are preferred, and divalent metals such as platinum and palladium are particularly preferred.
  • R 92 and R 93 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, a cyano group, an amino group, an acyl group, an alkoxycarbonyl group, a carboxyl group, represents an alkoxy group, an alkylamino group, an aralkylamino group, a haloalkyl group, a hydroxyl group, an aryloxy group, an aromatic hydrocarbon group or an aromatic heterocyclic group;
  • R94 and R95 each independently represent a substituent represented by the same examples as R92 and R93 . Also, when T is a nitrogen atom, there is no R94 or R95 directly bonded to said T.
  • R 92 to R 95 may further have a substituent.
  • Substituents can be the aforementioned substituents exemplified for R 92 and R 93 .
  • any two or more groups selected from R 92 to R 95 may be linked together to form a ring.
  • the molecular weight of the phosphorescent material is preferably 5,000 or less, more preferably 4,000 or less, and particularly preferably 3,000 or less. Further, the molecular weight of the phosphorescent material is usually 1000 or more, preferably 1100 or more, more preferably 1200 or more. It is believed that within this molecular weight range, the phosphorescent light-emitting materials do not aggregate with each other and are uniformly mixed with the compound of the present invention and/or other charge-transporting materials, so that a light-emitting layer with high light-emitting efficiency can be obtained.
  • the molecular weight of the phosphorescent light-emitting material has a high Tg, melting point, decomposition temperature, etc., and the phosphorescent light-emitting material and the formed light-emitting layer have excellent heat resistance, and the film quality due to gas generation, recrystallization, molecular migration, etc. A large value is preferable from the viewpoint that it is difficult to cause a decrease in the concentration of impurities and an increase in the concentration of impurities due to thermal decomposition of the material.
  • the molecular weight of the phosphorescent light-emitting material is preferably small in terms of facilitating purification of the organic compound.
  • composition of the present invention is a composition for forming a light-emitting layer, it preferably contains a charge-transporting material other than the aromatic compound of the present invention as a further host material in addition to the aromatic compound of the present invention.
  • the charge-transporting material used as the host material of the light-emitting layer is a material having a skeleton with excellent charge-transporting properties, and is selected from electron-transporting materials, hole-transporting materials, and bipolar materials capable of transporting both electrons and holes. preferably Furthermore, in the present invention, the charge transport material also includes a material that adjusts the charge transport property.
  • skeletons with excellent charge transport properties include aromatic structures, aromatic amine structures, triarylamine structures, dibenzofuran structures, naphthalene structures, phenanthrene structures, phthalocyanine structures, porphyrin structures, thiophene structures, benzylphenyl structures, fluorene structure, quinacridone structure, triphenylene structure, carbazole structure, pyrene structure, anthracene structure, phenanthroline structure, quinoline structure, pyridine structure, pyrimidine structure, triazine structure, oxadiazole structure, imidazole structure, and the like.
  • the compound represented by the formula (1) functions as an electron-transporting material, it is preferable to further include a hole-transporting material as a charge-transporting material.
  • a hole-transporting material is a compound having a structure with excellent hole-transporting properties, and among the skeletons with excellent charge-transporting properties, a carbazole structure, a dibenzofuran structure, a triarylamine structure, a naphthalene structure, a phenanthrene structure, or a pyrene structure. is preferable as a structure having excellent hole-transporting properties, and a carbazole structure, a dibenzofuran structure, or a triarylamine structure is more preferable. Particularly preferred is a compound represented by formula (240) described later.
  • the charge-transporting material used as the host material of the light-emitting layer is preferably a compound having a condensed ring structure of three or more rings, and at least a compound having two or more condensed ring structures of three or more rings or a condensed ring of five or more rings.
  • Compounds having one are more preferred. These compounds increase the rigidity of the molecules, making it easier to obtain the effect of suppressing the degree of molecular motion in response to heat.
  • the 3 or more condensed rings and the 5 or more condensed rings preferably have an aromatic hydrocarbon ring or an aromatic heterocyclic ring from the viewpoint of charge transportability and material durability.
  • condensed ring structures having three or more rings include anthracene structure, phenanthrene structure, pyrene structure, chrysene structure, naphthacene structure, triphenylene structure, fluorene structure, benzofluorene structure, indenofluorene structure, indolofluorene structure, Carbazole structure, indenocarbazole structure, indolocarbazole structure, dibenzofuran structure, dibenzothiophene structure and the like.
  • a carbazole structure or an indolocarbazole structure is more preferred from the viewpoint of resistance to electric charge.
  • the material for adjusting the charge-transporting property is preferably a compound represented by the formula (260) described later, which is a compound having a structure in which a large number of benzene rings are linked.
  • this compound By including this compound as a host material, it is thought that the excitons generated in the light-emitting layer are efficiently recombined to increase the light-emitting efficiency. deterioration is suppressed, and the driving life is lengthened.
  • composition of the present invention is a composition for forming a light-emitting layer
  • a compound represented by the formula (240) described later and/or the formula (260) described later It is preferable to contain a compound represented by as a charge transport material. Inclusion of such a compound as an additional host material is preferable from the viewpoint of charge balance adjustment in the light-emitting layer and from the viewpoint of luminous efficiency.
  • the charge-transporting material used as the host material of the light-emitting layer is preferably a polymeric material from the viewpoint of excellent flexibility.
  • a light-emitting layer formed using a material having excellent flexibility is preferable as a light-emitting layer of an organic electroluminescent device formed on a flexible substrate.
  • the charge-transporting material used as the host material contained in the light-emitting layer is a polymeric material, the molecular weight is preferably 5,000 or more and 1,000,000 or less, more preferably 10,000 or more and 500,000 or less, It is more preferably 10,000 or more and 100,000 or less.
  • the charge transport material used as the host material of the light emitting layer is easy to synthesize and purify, easy to design the electron transport performance and hole transport performance, and easy to adjust the viscosity when dissolved in a solvent. From the viewpoint of, it is preferably a low molecular weight.
  • the charge-transporting material used as the host material contained in the light-emitting layer is a low-molecular-weight material
  • the molecular weight is preferably 5,000 or less, more preferably 4,000 or less, and particularly preferably 3,000 or less.
  • a wet film formation method is preferably 1,000 or more, more preferably 1,100 or more, and particularly preferably 1,200 or more.
  • Ar 611 and Ar 612 each independently represent an optionally substituted monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • R 611 and R 612 are each independently a deuterium atom, a halogen atom, or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • G represents a single bond or an optionally substituted divalent aromatic hydrocarbon group having 6 to 50 carbon atoms
  • n 611 and n 612 are each independently an integer of 0-4.
  • Ar 611 and Ar 612 each independently represent an optionally substituted monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms.
  • the number of carbon atoms in the aromatic hydrocarbon group is preferably 6-50, more preferably 6-30, still more preferably 6-18.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, naphthalene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene ring, benzanthracene ring, perylene ring, and the like, which usually have 6 carbon atoms.
  • Ar 611 and Ar 612 are preferably each independently a phenyl group, a monovalent group in which a plurality of benzene rings are bonded in a chain or branched manner; a monovalent group in which one or more benzene rings and at least one naphthalene ring are linked in a chain or branched manner; a monovalent group in which one or more benzene rings and at least one phenanthrene ring are linked in a chain or branch, or a monovalent group in which one or more benzene rings and at least one tetraphenylene ring are linked in a chain or branched manner; and more preferably a monovalent group in which a plurality of benzene rings are bonded in a chain or branched manner, and in any case, the order of bonding is not critical.
  • Ar 611 and Ar 612 are each independently particularly preferably a monovalent group in which a plurality of optionally substituted benzene rings are bonded in a chain or branched manner, and each independently represents a plurality of benzene Most preferably, the ring is a multi-chain or branched monovalent group.
  • the number of bonded benzene rings, naphthalene rings, phenanthrene rings and tetraphenylene rings is usually 2-8, preferably 2-5, as described above.
  • a monovalent structure in which 1 to 4 benzene rings are connected a monovalent structure in which 1 to 4 benzene rings and a naphthalene ring are connected, 1 in which 1 to 4 benzene rings and a phenanthrene ring are connected
  • aromatic hydrocarbon groups may have substituents.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically can be selected from the substituent group Z2.
  • Preferred substituents are the preferred substituents of the substituent group Z2.
  • At least one of Ar 611 and Ar 612 preferably has at least one partial structure selected from the following formulas (72-1) to (72-7) from the viewpoint of compound solubility and durability.
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • At least one of Ar 611 and Ar 612 has at least one partial structure selected from formulas (72-1) to (72-4) and formula (72-7). More preferably, each of Ar 611 and Ar 612 has at least one partial structure selected from formulas (72-1) to (72-3) and formula (72-7). Particularly preferably, each of Ar 611 and Ar 612 has at least one partial structure selected from formula (72-1), formula (72-2) and formula (72-7).
  • Formula (72-2) is preferably the following formula (72-2-2).
  • the formula (72-2) is more preferably the following formula (72-2-3).
  • the partial structure that at least one of Ar 611 and Ar 612 preferably has is the partial structure represented by formula (72-1) and the partial structure represented by formula (72-2).
  • R 611 and R 612 are independently a deuterium atom, a halogen atom such as a fluorine atom, or an optionally substituted monovalent aromatic hydrocarbon having 6 to 50 carbon atoms.
  • a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent is preferred.
  • the aromatic hydrocarbon group is preferably a monovalent group having an aromatic hydrocarbon structure having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 10 carbon atoms.
  • Specific examples of the monovalent aromatic hydrocarbon group are the same as those of Ar 611 , and the same is true of the preferred aromatic hydrocarbon group, and the phenyl group is particularly preferred.
  • aromatic hydrocarbon groups may have a substituent.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically can be selected from the group of substituents Z2 described later. Preferred substituents are the preferred substituents of the substituent group Z2 described later.
  • n611 , n612 > n 611 and n 612 are each independently an integer of 0-4. It is preferably 0 to 2, more preferably 0 or 1.
  • Substituent group Z2 includes an alkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylalkylamino group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, A group consisting of an arylthio group, a silyl group, a siloxy group, a cyano group, an aromatic hydrocarbon group, and an aromatic heterocyclic group. These substituents may contain any structure of linear, branched and cyclic.
  • substituent group Z2 include the following structures. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, dodecyl group, etc.
  • the number of carbon atoms is usually 1 or more, preferably 4 or more, usually 24 or less, preferably 12 or less, more preferably 8 or less, and still more preferably 6 or less, linear, branched , or a cyclic alkyl group;
  • an aryloxy group or heteroaryloxy group having usually 4 or more carbon atoms, preferably 5 or more carbon atoms, usually 36 or less, preferably 24 or less carbon atoms such as phenoxy group, naphthoxy group, pyridyloxy group, etc.
  • an alkyl group, an alkoxy group, a diarylamino group, an aromatic hydrocarbon group, or an aromatic heterocyclic group is preferred.
  • the substituent is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, more preferably an aromatic hydrocarbon group, and further preferably has no substituent.
  • the substituent is preferably an alkyl group or an alkoxy group.
  • each substituent in the substituent group Z2 may further have a substituent.
  • substituent group Z2 examples include the same substituents as those described above (substituent group Z2).
  • Each substituent that the substituent group Z2 may have is preferably an alkyl group having 8 or less carbon atoms, an alkoxy group having 8 or less carbon atoms, or a phenyl group, more preferably an alkyl group having 6 or less carbon atoms, It is an alkoxy group having 6 or less carbon atoms or a phenyl group, and each substituent in the substituent group Z2 more preferably does not have a further substituent from the viewpoint of charge transport properties.
  • ⁇ G> G represents a single bond or an optionally substituted divalent aromatic hydrocarbon group having 6 to 50 carbon atoms.
  • the number of carbon atoms in the aromatic hydrocarbon group of G is preferably 6-50, more preferably 6-30, more preferably 6-18.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, naphthalene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene ring, benzanthracene ring, perylene ring, and the like, which usually have 6 carbon atoms.
  • G is preferably single bond, a phenylene group, a divalent group in which a plurality of benzene rings are bonded in a chain or branched manner; a divalent group in which one or more benzene rings and at least one naphthalene ring are linked in a chain or branched manner; a divalent group in which one or more benzene rings and at least one phenanthrene ring are linked in a chain or branched manner, or a divalent group in which one or more benzene rings and at least one tetraphenylene ring are linked in a chain or branched manner; and more preferably a divalent group in which a plurality of benzene rings are bonded in a chain or branched manner, and in any case, the order of bonding does not matter.
  • the number of bonded benzene rings, naphthalene rings, phenanthrene rings and tetraphenylene rings is usually 2-8, preferably 2-5, as described above.
  • a bivalent structure in which 1 to 4 benzene rings are linked a bivalent structure in which 1 to 4 benzene rings and a naphthalene ring are linked, 1 to 4 benzene rings and a phenanthrene ring are linked It is a bivalent structure, or a bivalent structure in which 1 to 4 benzene rings and a tetraphenylene ring are linked.
  • aromatic hydrocarbon groups may have substituents.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically can be selected from the substituent group Z2.
  • Preferred substituents are the preferred substituents of the substituent group Z2.
  • the compound represented by the formula (240) is a low-molecular-weight material, and has a molecular weight of preferably 3,000 or less, more preferably 2,500 or less, still more preferably 2,000 or less, and particularly preferably 1 , 500 or less, usually 300 or more, preferably 350 or more, more preferably 400 or more.
  • composition for forming a light-emitting layer of the present invention may contain only one compound represented by the formula (240), or may contain two or more compounds.
  • composition for forming a light-emitting layer of the present invention contains a compound represented by the following formula (260).
  • each of Ar 21 to Ar 35 is independently a hydrogen atom, an optionally substituted phenyl group or an optionally substituted phenyl group, 2 to 10, unbranched or It represents a branched and linked monovalent group.
  • Ar 21 to Ar 35 are optionally substituted phenyl groups or 2 to 10 optionally substituted phenyl groups are unbranched or branched and linked monovalent
  • the substituent that the phenyl group may have when it is a group is preferably an alkyl group.
  • alkyl group as a substituent usually has 1 or more and 12 or less carbon atoms, preferably 8 or less, more preferably 6 or less, and more preferably 4 or less, linear, branched or cyclic Alkyl group, specifically methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group , a cyclohexyl group, and a 2-ethylhexyl group.
  • Ar 21 , Ar 25 , Ar 26 , Ar 30 , Ar 31 and Ar 35 are preferably hydrogen atoms.
  • at least one of Ar 22 to Ar 24 is a phenyl group which may have a substituent or 2 to 10 phenyl groups which may have a substituent, which are unbranched or branched and linked 1 and/or at least one of Ar 22 to Ar 24 and at least one of Ar 27 to Ar 29 is a phenyl group optionally having the substituent or having the substituent It is preferably an unbranched or branched monovalent group having 2 to 10 phenyl groups which may be substituted.
  • Ar 22 to Ar 24 , Ar 27 to Ar 29 and Ar 32 to Ar 34 are selected from hydrogen atoms, phenyl groups, and the following formulas (261-1) to (261-9) is either
  • These structures may have the substituents described above, and may be substituted with alkyl groups as the substituents, for example. From the viewpoint of improving the solubility, it is preferably substituted with an alkyl group. From the viewpoint of charge transportability and durability during driving of the device, it is preferable not to have a substituent.
  • the compound represented by the formula (260) is a low-molecular-weight material, and has a molecular weight of preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1 , 500 or less, usually 300 or more, preferably 350 or more, more preferably 400 or more.
  • the compound represented by formula (260) is not particularly limited, and examples thereof include the following compounds.
  • composition for forming a light-emitting layer of the present invention may contain only one compound represented by the formula (260), or may contain two or more compounds.
  • composition for organic electroluminescence elements of the present invention may contain various other solvents, if necessary, in addition to the solvent and luminescent material described above.
  • other solvents include amides such as N,N-dimethylformamide and N,N-dimethylacetamide, and dimethylsulfoxide.
  • composition for organic electroluminescence elements of the present invention may contain various additives such as a leveling agent and an antifoaming agent.
  • a photocurable resin or a thermosetting resin is used for the purpose of curing and insolubilizing after film formation. can also be included.
  • the solid content concentration in the composition for organic electroluminescent elements is usually 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and still more preferably 0.5% by mass or more,
  • the content is most preferably 1% by mass or more, and usually 80% by mass or less, preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, and most preferably 20% by mass or less.
  • the solid content concentration is within this range, it is easy to form a thin film having a desired film thickness with a uniform thickness, which is preferable.
  • the preferred compounding ratio of the aromatic hydrocarbon compound of the present invention to all the host materials contained in the light-emitting layer is as follows. All host materials refer to all host materials other than the aromatic hydrocarbon compound of the present invention and the aromatic hydrocarbon compound of the present invention.
  • the mass ratio of the compound of the present invention to the mass of all host materials of 100 is 5 or more. , preferably 10 or more, more preferably 15 or more, more preferably 20 or more, particularly preferably 30 or more, 99 or less, preferably 95 or less, further preferably 90 or less, more preferably 80 or less, particularly preferably is 70 or less.
  • the molar ratio of the compound of the present invention to the total host material is preferably 5 mol% or more. is 10 mol% or more, more preferably 20 mol% or more, more preferably 25 mol% or more, particularly preferably 30 mol% or more, 90 mol% or less, preferably 80 mol% or less, more preferably is 70 mol % or less, particularly preferably 60 mol % or less.
  • the mass ratio of the light-emitting material to the mass of all host materials of 100 is 0.1.
  • it is preferably 0.5 or more, more preferably 1 or more, most preferably 2 or more, 100 or less, preferably 60 or less, further preferably 50 or less, most preferably 40 or less. If this ratio falls below the lower limit or exceeds the upper limit, the luminous efficiency may drop significantly.
  • composition for an organic electroluminescent element of the present invention is a solute comprising the aromatic compound of the present invention, the above-mentioned luminescent material as necessary, and various additives such as a leveling agent and an antifoaming agent that can be added as necessary. is prepared by dissolving in a suitable solvent.
  • the solute is usually dissolved while stirring the liquid.
  • the dissolution step may be performed at room temperature, but if the dissolution rate is slow, the dissolution may be performed by heating.
  • a filtering step such as filtering may be performed as necessary.
  • composition properties, physical properties, etc. moisture concentration
  • moisture concentration moisture concentration
  • the amount of water contained in the composition of the present invention is usually 1% by mass or less, preferably 0.1% by mass or less, and more preferably 0.01% by mass or less.
  • the composition of the present invention is preferably in a uniform liquid state at room temperature in order to improve stability in a wet film formation process, for example, ejection stability from a nozzle in an inkjet film formation method.
  • the uniform liquid state at room temperature means that the composition is a liquid consisting of a uniform phase and does not contain a particle component having a particle size of 0.1 ⁇ m or more in the composition.
  • the viscosity of the composition of the present invention at 25° C. is usually 2 mPa ⁇ s or more, preferably 3 mPa ⁇ s or more, more preferably 5 mPa ⁇ s or more, and usually 1000 mPa ⁇ s or less, preferably 100 mPa ⁇ s or less. , more preferably 50 mPa ⁇ s or less.
  • the surface tension of the composition of the present invention is high, the wettability of the film-forming liquid to the substrate is lowered, the leveling property of the liquid film is poor, and the film-forming surface is easily disturbed during drying. may occur
  • the surface tension of the composition of the present invention at 20°C is usually less than 50 mN/m, preferably less than 40 mN/m.
  • the vapor pressure of the composition of the present invention at 25°C is usually 50 mmHg or less, preferably 10 mmHg or less, more preferably 1 mmHg or less.
  • a film forming method using the composition of the present invention is a wet film forming method.
  • the wet film-forming method is a method in which a composition is applied to form a liquid film, dried to remove the organic solvent, and a film is formed.
  • the composition of the present invention is a composition for an organic electroluminescence device
  • the organic layer of the organic electroluminescence device can be formed by a thin film forming method comprising a step of forming a film from the composition by a wet film formation method.
  • the composition of the present invention contains a light-emitting material, a light-emitting layer can be formed by this method.
  • coating methods include spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet, nozzle printing, screen printing, and gravure. It refers to a method of forming a film by employing a wet film-forming method such as a printing method or a flexographic printing method, and drying the coating film.
  • a wet film-forming method such as a printing method or a flexographic printing method, and drying the coating film.
  • the spin coating method, the spray coating method, the inkjet method, the nozzle printing method, and the like are preferable.
  • an inkjet method or a nozzle printing method is preferable, and an inkjet method is particularly preferable.
  • drying method is not particularly limited, natural drying, reduced pressure drying, heat drying, or reduced pressure drying while heating can be used as appropriate. Heat drying may be carried out in order to further remove residual organic solvent after natural drying or vacuum drying.
  • the reduced pressure drying is carried out at a pressure equal to or lower than the vapor pressure of the organic solvent contained in the composition for forming the light-emitting layer.
  • the heating method is not particularly limited, but heating with a hot plate, heating in an oven, infrared heating, etc. can be used.
  • the heating time is generally 80° C. or higher, preferably 100° C. or higher, more preferably 110° C. or higher, and preferably 200° C. or lower, more preferably 150° C. or lower.
  • the heating time is usually 1 minute or longer, preferably 2 minutes or longer, usually 60 minutes or shorter, preferably 30 minutes or shorter, and more preferably 20 minutes or shorter.
  • an electron transport layer is formed on the light emitting layer.
  • composition for forming an electron transport layer in the invention contains at least an electron transport layer material and a solvent.
  • a solvent for the composition for forming the electron transport layer an alcohol-based solvent is preferable.
  • an electron transport layer material of the electron transport layer-forming composition an electron transport material soluble in the alcohol solvent is preferable.
  • aliphatic alcohols with 3 or more carbon atoms are preferred. Aliphatic alcohols having 6 or more carbon atoms are more preferable because they easily dissolve the electron-transporting material, have a moderately high boiling point, and easily form a flat film.
  • Preferred aliphatic alcohol solvents include 1-butanol, isobutyl alcohol, 2-hexanol, 1,2-hexanediol, 1-hexanol, 1-heptanol, 3,5,5-trimethyl-1-hexanol, 2-methyl-2- Pentanol, 4-methyl-3-heptanol, 3-methyl-2-pentanol, 4-methyl-1-pentanol, 1-nonen-3-ol, 4-heptanol, 1-methoxy-2-propanol, 3-methyl-1-pentane tanol, 4-octanol, 3,3-diethoxy-1-propanol, 3-(methylamino)-1-propanol and the like.
  • a solvent two or more of these alcohols may be mixed.
  • FIG. 1 shows a schematic diagram (cross section) of a structural example of the organic electroluminescence device 8 .
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transport layer
  • 5 is a light emitting layer
  • 6 is an electron transport layer
  • 7 is a cathode.
  • the substrate 1 serves as a support for the organic electroluminescence element, and is usually made of a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, or the like. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate and polysulfone are preferred.
  • the substrate is preferably made of a material having a high gas barrier property because deterioration of the organic electroluminescence element due to outside air is unlikely to occur. Therefore, especially when using a material having low gas barrier properties such as a synthetic resin substrate, it is preferable to provide a dense silicon oxide film or the like on at least one side of the substrate to improve the gas barrier properties.
  • the anode 2 has the function of injecting holes into the layer on the light-emitting layer 5 side.
  • Anode 2 is typically made of metals such as aluminum, gold, silver, nickel, palladium, platinum; metal oxides such as indium and/or tin oxide; metal halides such as copper iodide; carbon black and poly(3 -methylthiophene), polypyrrole, and polyaniline.
  • metals such as aluminum, gold, silver, nickel, palladium, platinum
  • metal oxides such as indium and/or tin oxide
  • metal halides such as copper iodide
  • the formation of the anode 2 is usually carried out by dry methods such as sputtering and vacuum deposition.
  • an appropriate binder resin solution may be used. It can also be formed by dispersing and coating on a substrate.
  • a conductive polymer a thin film can be formed directly on a substrate by electrolytic polymerization, or an anode can be formed by coating a conductive polymer on a substrate (Appl. Phys. Lett., 60 2711, 1992).
  • the anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, different conductive materials may be laminated on the first layer of the anode.
  • the thickness of the anode 2 may be determined according to the required transparency and material. When particularly high transparency is required, the thickness is preferably such that the visible light transmittance is 60% or more, and more preferably the thickness is such that the visible light transmittance is 80% or more.
  • the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
  • the thickness of the anode 2 may be arbitrarily set according to the required strength, etc. In this case, the thickness of the anode 2 may be the same as that of the substrate.
  • the impurity on the anode 2 is removed and its ionization potential is changed by treating with ultraviolet rays/ozone, oxygen plasma, argon plasma, etc. before the film formation. is preferably adjusted to improve the hole injection property.
  • a layer that functions to transport holes from the anode 2 side to the light emitting layer 5 side is usually called a hole injection transport layer or a hole transport layer.
  • the layer closer to the anode side may be called the hole injection layer 3 .
  • the hole injection layer 3 is preferably formed in order to enhance the function of transporting holes from the anode 2 to the light emitting layer 5 side.
  • the hole injection layer 3 is usually formed on the anode 2 .
  • the thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
  • the method for forming the hole injection layer may be a vacuum deposition method or a wet film formation method. From the viewpoint of excellent film-forming properties, it is preferable to form the film by a wet film-forming method.
  • a general method for forming a hole injection layer will be described below. preferably formed.
  • the composition for forming a hole injection layer usually contains a hole-transporting compound for a hole-injection layer that becomes the hole-injection layer 3 .
  • the hole injection layer-forming composition usually further contains a solvent. It is preferable that the composition for forming a hole injection layer has a high hole-transporting property and can efficiently transport the injected holes. For this reason, it is preferable that the hole mobility is large and that impurities that become traps are less likely to occur during manufacture or use. Moreover, it is preferable that it has excellent stability, a small ionization potential, and a high transparency to visible light.
  • the hole injection layer when the hole injection layer is in contact with the light-emitting layer, it is preferable to use a material that does not quench light emitted from the light-emitting layer or that forms an exciplex with the light-emitting layer so as not to lower the light emission efficiency.
  • the hole-transporting compound for the hole-injection layer is preferably a compound having an ionization potential of 4.5 eV to 6.0 eV from the viewpoint of a charge injection barrier from the anode to the hole-injection layer.
  • hole-transporting compounds include aromatic amine-based compounds, phthalocyanine-based compounds, porphyrin-based compounds, oligothiophene-based compounds, polythiophene-based compounds, benzylphenyl-based compounds, and tertiary amines linked with fluorene groups. compounds, hydrazone-based compounds, silazane-based compounds, quinacridone-based compounds, and the like.
  • aromatic amine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, in terms of amorphousness and visible light transparency.
  • the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure, and includes a compound having a group derived from an aromatic tertiary amine.
  • the type of the aromatic tertiary amine compound is not particularly limited, but from the viewpoint of easily obtaining uniform light emission due to the surface smoothing effect, a polymer compound having a weight average molecular weight of 1000 or more and 1000000 or less (polymeric compound in which repeating units are linked) ) is preferably used.
  • a film-forming composition (hole injection Layer-forming composition) is prepared. Then, the hole injection layer 3 is formed by coating the hole injection layer forming composition on the layer (usually the anode) corresponding to the lower layer of the hole injection layer to form a film and drying it.
  • the concentration of the hole-transporting compound in the hole-injection layer-forming composition is arbitrary as long as it does not significantly impair the effects of the present invention. , a higher value is preferable from the viewpoint that defects are less likely to occur in the hole injection layer. Specifically, it is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, particularly preferably 0.5% by mass or more, and on the other hand, 70% by mass. is preferably 60% by mass or less, and particularly preferably 50% by mass or less.
  • solvents examples include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, and amide-based solvents.
  • ether-based solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole. , phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole and 2,4-dimethylanisole.
  • aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole.
  • PGMEA propylene glycol-1-monomethyl ether acetate
  • 1,2-dimethoxybenzene 1,3-dimethoxybenzen
  • ester-based solvents include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.
  • aromatic hydrocarbon solvents examples include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, and methylnaphthalene. be done.
  • amide-based solvents examples include N,N-dimethylformamide and N,N-dimethylacetamide.
  • dimethyl sulfoxide and the like can also be used.
  • Formation of the hole injection layer 3 by a wet film-forming method is usually carried out by preparing a composition for forming a hole injection layer and then applying it on a layer corresponding to the lower layer of the hole injection layer 3 (usually the anode 2). It is carried out by coating and forming a film on the surface and drying it.
  • the coating film is usually dried by heating, drying under reduced pressure, or the like.
  • the hole injection layer 3 is formed by a vacuum deposition method
  • one or more of the constituent materials of the hole injection layer 3 are usually placed in a crucible placed in a vacuum vessel (two or more materials are placed in separate crucibles), and the inside of the vacuum chamber is evacuated to about 10 ⁇ 4 Pa by a vacuum pump.
  • the crucible is heated (usually each crucible is heated when two or more materials are used) to evaporate while controlling the amount of evaporation of the material in the crucible (when two or more materials are used, (usually independently controlling the amount of evaporation) to form a hole-injecting layer on the anode on the substrate placed facing the crucible.
  • a mixture thereof can be placed in a crucible, heated and evaporated to form the hole injection layer.
  • the degree of vacuum during vapor deposition is not limited as long as it does not significantly impair the effects of the present invention. 12.0 ⁇ 10 ⁇ 4 Pa) or less.
  • the vapor deposition rate is not limited as long as it does not significantly impair the effects of the present invention, but is usually 0.1 ⁇ /second or more and 5.0 ⁇ /second or less.
  • the film formation temperature during vapor deposition is not limited as long as the effects of the present invention are not significantly impaired, but is preferably 10° C. or higher and 50° C. or lower.
  • hole injection layer 3 may be crosslinked in the same manner as the hole transport layer 4 described later.
  • the hole transport layer 4 is a layer that functions to transport holes from the anode 2 side to the light emitting layer 5 side.
  • the hole transport layer 4 is not an essential layer in the organic electroluminescent device of the present invention, but it is preferable to form this layer in terms of enhancing the function of transporting holes from the anode 2 to the light emitting layer 5. .
  • the hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5 . Further, when the hole injection layer 3 described above is present, it is formed between the hole injection layer 3 and the light emitting layer 5 .
  • the film thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and is usually 300 nm or less, preferably 100 nm or less.
  • a material that forms the hole transport layer 4 is preferably a material that has a high hole transport property and can efficiently transport the injected holes. Therefore, it is preferable that the ionization potential is low, the transparency to visible light is high, the hole mobility is high, the stability is excellent, and impurities that act as traps are less likely to occur during manufacture or use. In many cases, since the hole transport layer 4 is in contact with the light emitting layer 5, it does not quench the light emitted from the light emitting layer 5 or form an exciplex with the light emitting layer 5 to reduce the efficiency. is preferred.
  • any material can be used as long as it is a material conventionally used as a constituent material of a hole transport layer.
  • compounds include those exemplified.
  • polyvinylcarbazole derivatives polyarylamine derivatives, polyvinyltriphenylamine derivatives, polyfluorene derivatives, polyarylene derivatives, polyarylene ether sulfone derivatives containing tetraphenylbenzidine, polyarylene vinylene derivatives, polysiloxane derivatives, polythiophenes. derivatives, poly(p-phenylene vinylene) derivatives and the like.
  • These may be alternating copolymers, random polymers, block polymers or graft copolymers.
  • a polymer having a branched main chain and three or more terminal portions, or a so-called dendrimer may be used.
  • polyarylamine derivatives and polyarylene derivatives are preferred.
  • a polymer containing a repeating unit represented by the following formula (II) is preferred.
  • a polymer composed of repeating units represented by the following formula (II) is preferable, and in this case, Ar a or Ar b may be different in each repeating unit.
  • Ar a and Ar b each independently represent an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group .
  • polyarylene derivatives include polymers having arylene groups such as optionally substituted aromatic hydrocarbon groups or optionally substituted aromatic heterocyclic groups in their repeating units.
  • polyarylene derivative a polymer having repeating units represented by the following formula (III-1) and/or the following formula (III-2) is preferable.
  • R a , R b , R c and R d are each independently an alkyl group, an alkoxy group, a phenylalkyl group, a phenylalkoxy group, a phenyl group, a phenoxy group, an alkylphenyl group, represents an alkoxyphenyl group, an alkylcarbonyl group, an alkoxycarbonyl group or a carboxy group, and t and s each independently represents an integer of 0 to 3.
  • t or s is 2 or more, a plurality of groups contained in one molecule may be the same or different, and adjacent Ra or Rb may form a ring.
  • R e and R f are each independently synonymous with R a , R b , R c or R d in formula (III-1) above.
  • r and u are each independently represents an integer of 0 to 3. When r or u is 2 or more, a plurality of R e and R f contained in one molecule may be the same or different, and adjacent R e or R f may form a ring together, and X represents an atom or a group of atoms constituting a 5- or 6-membered ring.
  • X include an oxygen atom, an optionally substituted boron atom, an optionally substituted nitrogen atom, an optionally substituted silicon atom, and an optionally substituted an optionally substituted phosphorus atom, an optionally substituted sulfur atom, an optionally substituted carbon atom, or a group formed by combining these atoms.
  • polyarylene derivative has a repeating unit represented by the following formula (III-3) in addition to the repeating unit represented by the above formula (III-1) and/or the above formula (III-2). is preferred.
  • Ar c to Ar i each independently represent an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group; and v and w each independently represent 0 or 1.
  • a composition for forming a hole transport layer is prepared in the same manner as in the formation of the hole injection layer 3, and after wet film formation, heat drying is performed. .
  • the hole-transporting layer-forming composition contains a solvent in addition to the hole-transporting compound described above.
  • the solvent to be used is the same as that used for the composition for forming the hole injection layer.
  • the film formation conditions, heat drying conditions, etc. are the same as in the case of forming the hole injection layer 3 .
  • the film forming conditions and the like are the same as in the case of forming the hole injection layer 3 described above.
  • the hole-transporting layer 4 may contain various light-emitting materials, electron-transporting compounds, binder resins, coatability improvers, etc., in addition to the above hole-transporting compounds.
  • the hole transport layer 4 may be a layer formed by cross-linking a cross-linking compound.
  • the crosslinkable compound is a compound having a crosslinkable group, and forms a network polymer compound by crosslinking.
  • crosslinkable groups include groups derived from cyclic ethers such as oxetane and epoxy; groups derived from unsaturated double bonds such as vinyl, trifluorovinyl, styryl, acryl, methacryloyl, and cinnamoyl; Examples thereof include groups derived from cyclobutene.
  • the crosslinkable compound may be a monomer, oligomer, or polymer.
  • the crosslinkable compound may have only one type, or may have two or more types in any combination and ratio.
  • a hole-transporting compound having a crosslinkable group is preferably used as the crosslinkable compound.
  • the hole-transporting compound include those exemplified above, and examples of the cross-linking compound include those in which a cross-linking group is bonded to the main chain or side chain of these hole-transporting compounds. be done.
  • the crosslinkable group is preferably bonded to the main chain via a linking group such as an alkylene group.
  • the hole-transporting compound is preferably a polymer containing a repeating unit having a crosslinkable group. is preferably a polymer having repeating units linked directly or via a linking group.
  • a composition for forming a hole transport layer is usually prepared by dissolving or dispersing the cross-linking compound in a solvent, and the film is formed by wet film formation. to cross-link.
  • the film thickness of the hole transport layer 4 thus formed is usually 5 nm or more, preferably 10 nm or more, and usually 300 nm or less, preferably 100 nm or less.
  • the light-emitting layer 5 is a layer that functions to emit light by being excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 7 when an electric field is applied between a pair of electrodes. .
  • the light-emitting layer 5 is a layer formed between the anode 2 and the cathode 7, and the light-emitting layer is formed between the hole-injection layer and the cathode, if there is a hole-injection layer on the anode, and the anode If there is a hole-transport layer on top, it is formed between the hole-transport layer and the cathode.
  • the organic electroluminescent device in the present invention preferably contains the aromatic compound and the luminescent material of the present invention as the luminescent layer.
  • the film thickness of the light-emitting layer 5 is arbitrary as long as it does not significantly impair the effects of the present invention. However, a thicker film is preferable because defects are less likely to occur in the film. . Therefore, it is preferably 3 nm or more, more preferably 5 nm or more, and on the other hand, it is usually preferably 200 nm or less, more preferably 100 nm or less.
  • the light-emitting layer 5 contains at least a material having light-emitting properties (light-emitting material), and preferably contains one or more host materials.
  • a hole-blocking layer may be provided between the light-emitting layer 5 and an electron-injecting layer, which will be described later.
  • the hole-blocking layer is a layer laminated on the light-emitting layer 5 so as to be in contact with the interface of the light-emitting layer 5 on the cathode 7 side.
  • This hole-blocking layer has the role of blocking holes moving from the anode 2 from reaching the cathode 7 and the role of efficiently transporting electrons injected from the cathode 7 toward the light-emitting layer 5.
  • the physical properties required for the material constituting the hole blocking layer include high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and an excited triplet level (T 1 ). is high.
  • Examples of materials for the hole blocking layer that satisfy these conditions include bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl-8-quinolinolato)(triphenylsilanolate)aluminum, and the like.
  • mixed ligand complexes bis (2-methyl-8-quinolato) aluminum- ⁇ -oxo-bis- (2-methyl-8-quinolato) aluminum binuclear metal complexes such as metal complexes, distyrylbiphenyl derivatives and the like Styryl compounds (JP-A-11-242996), triazole derivatives such as 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole ( JP-A-7-41759), phenanthroline derivatives such as bathocuproine (JP-A-10-79297), and the like.
  • the compound having at least one pyridine ring substituted at the 2,4,6 positions described in WO 2005/022962 is also preferable as a material for the hole blocking layer.
  • the hole blocking layer There are no restrictions on the method of forming the hole blocking layer. Therefore, it can be formed by a wet film forming method, a vapor deposition method, or other methods.
  • the thickness of the hole-blocking layer is arbitrary as long as it does not significantly impair the effects of the present invention, but it is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less. .
  • the electron transport layer 6 is provided between the light emitting layer 5 and the cathode 7 for the purpose of further improving the current efficiency of the device.
  • the electron transport layer 6 is made of a compound that can efficiently transport electrons injected from the cathode 7 toward the light emitting layer 5 between electrodes to which an electric field is applied.
  • the electron-transporting compound used in the electron-transporting layer 6 is a compound that has high electron injection efficiency from the cathode 7, high electron mobility, and can efficiently transport the injected electrons. is required.
  • the electron-transporting compound used in the electron-transporting layer include, for example, a metal complex such as an aluminum complex of 8-hydroxyquinoline (Japanese Patent Laid-Open No. 59-194393), 10-hydroxybenzo[h] quinoline metal complexes, oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, trisbenzimidazolylbenzene (US Patent No. 5645948), quinoxaline compounds (Japanese Patent Laid-Open No.
  • the film thickness of the electron transport layer 6 is usually 1 nm or more, preferably 5 nm or more, and is usually 300 nm or less, preferably 100 nm or less.
  • the electron transport layer 6 is formed on the hole blocking layer by a wet film forming method or a vacuum vapor deposition method in the same manner as described above.
  • a vacuum deposition method is usually used.
  • the electron transport layer can be formed on the light-emitting layer containing the aromatic compound of the invention by a wet film-forming method.
  • the electron injection layer may be provided to efficiently inject electrons injected from the cathode 7 into the electron transport layer 6 or the light emitting layer 5 .
  • the material forming the electron injection layer be a metal with a low work function.
  • examples thereof include alkali metals such as sodium and cesium, alkaline earth metals such as barium and calcium, and the like.
  • the film thickness is preferably 0.1 nm or more and 5 nm or less.
  • an organic electron-transporting material typified by a nitrogen-containing heterocyclic compound such as bathophenanthroline or a metal complex such as an aluminum complex of 8-hydroxyquinoline is doped with an alkali metal such as sodium, potassium, cesium, lithium or rubidium ( JP-A-10-270171, JP-A-2002-100478, JP-A-2002-100482, etc.) also improves electron injection and transport properties and achieves excellent film quality. It is preferable because it enables
  • the thickness of the electron injection layer is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.
  • the electron injection layer is formed by laminating the light emitting layer 5 or the hole blocking layer or the electron transport layer 6 thereon by a wet film forming method or a vacuum deposition method.
  • the details of the wet film formation method are the same as those of the light-emitting layer described above.
  • the hole-blocking layer, electron-transporting layer, and electron-injecting layer are formed into a single layer by co-doping the electron-transporting material and the lithium complex.
  • the cathode 7 plays a role of injecting electrons into a layer (an electron injection layer, a light-emitting layer, or the like) on the light-emitting layer 5 side.
  • the material of the cathode 7 it is possible to use the material used for the anode 2, but in terms of efficient electron injection, it is preferable to use a metal with a low work function, such as tin or magnesium. , indium, calcium, aluminum, and silver, or alloys thereof. Specific examples include low work function alloy electrodes such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys.
  • the cathode made of a metal with a low work function by stacking a metal layer that has a high work function and is stable against the atmosphere on the cathode.
  • Metals to be laminated include, for example, metals such as aluminum, silver, copper, nickel, chromium, gold, and platinum.
  • the film thickness of the cathode is usually the same as that of the anode.
  • the organic electroluminescence device of the present invention may further have other layers as long as they do not significantly impair the effects of the present invention. That is, it may have any of the other layers described above between the anode and cathode.
  • the organic electroluminescence device of the present invention has a structure opposite to that described above. It is also possible to laminate the injection layer and the anode in this order.
  • the organic electroluminescent element of the present invention When the organic electroluminescent element of the present invention is applied to an organic electroluminescent device, it may be used as a single organic electroluminescent element or may be used in a configuration in which a plurality of organic electroluminescent elements are arranged in an array. A configuration in which anodes and cathodes are arranged in an XY matrix may be used.
  • An organic electroluminescent device uses the composition for an organic electroluminescent device described above.
  • An organic electroluminescent device can have, for example, an anode and a cathode on a substrate, and an organic layer between the anode and the cathode.
  • One aspect of the method for producing an organic electroluminescent device of the present invention can include a step of forming an organic layer by a wet film-forming method using the composition for an organic electroluminescent device described above.
  • the organic layer can be, for example, an emissive layer.
  • the organic layer includes a light-emitting layer and an electron-transporting layer, and the light-emitting layer is formed by a wet film-forming method using the composition for an organic electroluminescent device described above. and a step of forming the electron transport layer by a wet film-forming method using an electron transport layer composition containing an electron transport material and a solvent, in this order.
  • the solvent contained in the electron transport layer composition can be an alcohol solvent.
  • the electron transport layer formed by the wet film formation method can be formed so as to be directly laminated on the light emitting layer formed by the wet film formation method.
  • the organic EL display device (organic electroluminescence element display device or display device) of the present invention comprises the organic electroluminescence element of the present invention.
  • the type and structure of the organic EL display device of the present invention are not particularly limited, and the organic electroluminescence device of the present invention can be assembled according to a conventional method.
  • the organic EL display device of the present invention can be manufactured by the method described in "Organic EL Display” (Ohmsha, August 20, 2004, by Shizuo Tokito, Chihaya Adachi, and Hideyuki Murata). can be formed.
  • the organic EL lighting (organic electroluminescence device lighting or lighting device) of the present invention comprises the organic electroluminescence device of the present invention.
  • the type and structure of the organic EL lighting of the present invention are not particularly limited, and the organic electroluminescence device of the present invention can be assembled according to a conventional method.
  • compound 1-f (7.8 g, 11.7 mmol) and compound 1-g (7.7 g, 10.6 mmol) were subjected to nitrogen bubbling in THF (50 mL), tripotassium phosphate aqueous solution (2. 0 mol/L, 15 mL) were sequentially added. After that, Pd(PPh 3 ) 4 (0.12 g, 0.11 mmol) was added, and the mixture was heated and stirred at 75° C. for 4 hours. After cooling to room temperature, a saturated aqueous sodium chloride solution and 1N dilute hydrochloric acid were added, and extraction was performed using dichloromethane.
  • compound 2-e 3.3 g, 9.28 mmol
  • compound 2-f 3.6 g, 9.28 mmol
  • nitrogen bubbling toluene 40 mL
  • ethanol 20 mL
  • triphosphate A potassium aqueous solution (2.0 mol/L, 20 mL) was added in order.
  • Pd(PPh 3 ) 4 (0.11 g, 0.093 mmol) was added and heated with stirring at 90° C. for 4 hours. After cooling to room temperature, a saturated sodium chloride aqueous solution was added, and extraction was performed using toluene.
  • the compounds (H-1) to (H-3) of the present invention and the comparative compound (C-2) had a solubility in CHB of 12.0% by mass or more.
  • the substrate on which the compound film was formed was set in a spin coater, 150 ⁇ l of the test solvent was dropped onto the substrate, and after dropping, the substrate was allowed to stand for 60 seconds to conduct a solvent resistance test.
  • the substrate was spun at 1500 rpm for 30 seconds and then at 4000 rpm for 30 seconds to spin out the dropped solvent.
  • This substrate was dried on a hot plate at 100° C. for 10 minutes.
  • the film thickness change before and after the solvent resistance test was estimated from each film thickness difference.
  • the film thickness after film formation of each compound and the test solvent used are as follows.
  • Comparative compound (C-1) A film of 54 nm was formed using the comparative compound (C-1), and a solvent resistance test was conducted using 1-butanol as the test solvent.
  • the solvent resistance of the compound after film formation was evaluated based on the following criteria. ⁇ : No decrease in film thickness was observed. x: A film thickness reduction of 5 nm or more was observed. Table 3 shows the results of the solvent resistance test.
  • Example 1 An organic electroluminescence device was produced by the following method.
  • An indium tin oxide (ITO) transparent conductive film deposited on a glass substrate to a thickness of 50 nm (manufactured by Geomatec, a sputter-deposited product) was subjected to a 2 mm-wide stripe using ordinary photolithography and etching with hydrochloric acid. was patterned to form an anode.
  • the substrate on which the ITO pattern is formed in this manner is washed with ultrasonic waves using an aqueous solution of surfactant, washed with ultrapure water, ultrasonically washed with ultrapure water, and washed with ultrapure water in this order, and then dried with compressed air.
  • composition for forming a hole injection layer 3.0% by weight of a hole-transporting polymer compound having a repeating structure of the following formula (P-1) and 0.6% by weight of an electron-accepting compound (HI-1) was dissolved in ethyl benzoate to prepare a composition.
  • This solution was spin-coated on the substrate in the atmosphere and dried on a hot plate in the atmosphere at 240° C. for 30 minutes to form a uniform thin film with a thickness of 40 nm, which was used as a hole injection layer.
  • a charge-transporting polymer compound having the following structural formula (HT-1) was dissolved in 1,3,5-trimethylbenzene to prepare a 2.0% by weight solution.
  • This solution was spin-coated on the substrate on which the hole injection layer was coated in a nitrogen glove box, and dried on a hot plate in the nitrogen glove box at 230° C. for 30 minutes to form a uniform thin film with a thickness of 40 nm. was formed to form a hole transport layer.
  • This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been applied and dried on a hot plate in the nitrogen glove box at 120° C. for 20 minutes to form a uniform thin film with a thickness of 40 nm. was formed to form a light-emitting layer.
  • the substrate on which up to the light-emitting layer was formed was placed in a vacuum deposition apparatus, and the inside of the apparatus was evacuated to 2 ⁇ 10 ⁇ 4 Pa or less.
  • the following structural formula (ET-1) and 8-hydroxyquinolinolatritium were co-deposited on the light-emitting layer at a film thickness ratio of 2:3 by a vacuum vapor deposition method to form an electron-transporting layer having a film thickness of 30 nm. formed.
  • a striped shadow mask with a width of 2 mm was adhered to the substrate so as to be orthogonal to the ITO stripes of the anode as a mask for cathode evaporation, and aluminum was heated with a molybdenum boat to form an aluminum layer with a thickness of 80 nm. formed to form the cathode.
  • an organic electroluminescence device having a light-emitting area of 2 mm ⁇ 2 mm was obtained.
  • Example 2 An organic electroluminescence device was produced in the same manner as in Example 1, except that the compound (H-2) of the present invention was used instead of the compound (H-1) as the material for the light-emitting layer.
  • Example 3 An organic electroluminescence device was produced in the same manner as in Example 1, except that the compound (H-3) of the present invention was used instead of the compound (H-1) as the material for the light-emitting layer.
  • Example 1 An organic electroluminescence device was produced in the same manner as in Example 1, except that the comparative compound (C-2) was used instead of the compound (H-1) as the material of the light-emitting layer.
  • Example 4 An organic electroluminescence device was produced in the same manner as in Example 1, except that the light-emitting layer was formed as follows. As materials for the light-emitting layer, the compound (H-1) was 2.7% by weight, the following compound (HH-2) was 2.7% by weight, and the compound (D-1) was cyclohexyl at a concentration of 1.6% by weight. It was made to melt
  • the composition for forming a light emitting layer was spin-coated on the substrate on which the hole transport layer was formed in a nitrogen glove box, dried on a hot plate in the nitrogen glove box at 120 ° C. for 20 minutes, and a uniform film thickness of 70 nm. A thin film was formed to form a light-emitting layer.
  • Example 5 An organic electroluminescence device was produced in the same manner as in Example 4, except that the compound (H-2) of the present invention was used instead of the compound (H-1) as the material for the light-emitting layer.
  • Example 6 An organic electroluminescence device was produced in the same manner as in Example 4, except that the compound (H-3) of the present invention was used instead of the compound (H-1) as the material for the light-emitting layer.
  • Comparative Example 2 An organic electroluminescence device was produced in the same manner as in Example 4, except that the comparative compound (C-2) was used instead of the compound (H-1) as the material of the light-emitting layer.
  • the present invention can provide an aromatic compound having excellent heat resistance, excellent solubility, excellent electron transport properties, and excellent resistance to alcohol solvents in thin films.
  • the present invention also provides an organic electroluminescent device containing the compound, a display device and a lighting device comprising the organic electroluminescent device, a composition containing the compound and a solvent, a method for forming a thin film, and a method for manufacturing an organic electroluminescent device. can provide.

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Abstract

La présente invention aborde le problème de la fourniture d'un composé aromatique qui présente une excellente résistance à la chaleur, une excellente solubilité et d'excellentes propriétés de transport d'électrons et qui permet d'obtenir des films minces présentant une excellente résistance aux solvants alcooliques. La présente invention concerne : un composé aromatique représenté par la formule (1) ; un élément électroluminescent organique comprenant une couche organique qui comprend le composé aromatique en tant que matériau pour des éléments électroluminescents organiques ; une composition pour éléments électroluminescents organiques qui comprend le composé aromatique et un solvant ; et un procédé de production de l'élément électroluminescent organique. (Dans la formule (1), G1, G2 et G3 ont respectivement les mêmes significations que celles définies dans la description).
PCT/JP2022/022397 2021-06-04 2022-06-01 Composé aromatique, élément électroluminescent organique, composition et procédé de production d'élément électroluminescent organique WO2022255428A1 (fr)

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JP2023525903A JPWO2022255428A1 (fr) 2021-06-04 2022-06-01
CN202280039377.0A CN117480156A (zh) 2021-06-04 2022-06-01 芳香族化合物、有机电致发光元件、组合物及有机电致发光元件的制造方法

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