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WO2015194429A1 - Solvant permettant la fabrication d'éléments électroluminescents organiques - Google Patents

Solvant permettant la fabrication d'éléments électroluminescents organiques Download PDF

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Publication number
WO2015194429A1
WO2015194429A1 PCT/JP2015/066703 JP2015066703W WO2015194429A1 WO 2015194429 A1 WO2015194429 A1 WO 2015194429A1 JP 2015066703 W JP2015066703 W JP 2015066703W WO 2015194429 A1 WO2015194429 A1 WO 2015194429A1
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group
ring
solvent
formula
organic
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English (en)
Japanese (ja)
Inventor
鈴木陽二
横尾健
赤井泰之
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Daicel Corp
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Daicel Corp
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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
    • H10K50/80—Constructional details
    • 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

Definitions

  • the present invention relates to a solvent for producing an organic EL device excellent in solubility of an organic semiconductor material, and a composition for producing an organic EL device comprising the solvent for producing an organic EL device and an organic semiconductor material.
  • Organic electroluminescence (sometimes referred to as “organic EL” in this specification) element is a light emitting device formed of an organic semiconductor material, and emits light by excitons generated by recombination of electrons and holes.
  • a method for forming an organic EL element by applying an organic semiconductor material by ink jet printing, spin coating or the like has attracted attention.
  • the coating method it is possible to easily form a film by applying a coating solution to a substrate and then removing the solvent in the coating solution, so that it is highly productive and energy-saving, and can be easily applied to a large area device. Is excellent.
  • organic semiconductor material used for forming the organic EL element examples include 4,4′-bis (N-carbazolyl) -1,1′-biphenyl (CBP), poly [(9,9-dioctylfluoronyl-2).
  • carbazole biphenyl Since carbazole biphenyl has poor solubility in a solvent, it is not possible to prepare a composition for manufacturing an organic EL device in which an organic semiconductor material is dissolved at a high concentration, and it is difficult to form a thick organic layer. It was.
  • Patent Document 2 describes introducing a solubilization site into an organic semiconductor material
  • Patent Document 3 describes introducing a leaving substituent that imparts solubility to the organic semiconductor material.
  • phase transition and stability decrease occur due to the introduction of the solubilized site.
  • a detachable substituent that imparts solubility is eliminated by heating during dissolution.
  • the object of the present invention is excellent in the solubility of the organic semiconductor material, and by dissolving the organic semiconductor material, a composition for producing an organic EL element for forming an organic EL element by a coating method can be formed. It is in providing the solvent for organic electroluminescent element manufacture.
  • Another object of the present invention is to provide an organic EL device manufacturing composition for forming an organic EL device on a plastic substrate by a coating method by dissolving the organic semiconductor material with excellent solubility of the organic semiconductor material. It is providing the solvent for organic electroluminescent element manufacture which can be formed.
  • Another object of the present invention is to provide a composition for producing an organic EL device capable of forming an organic EL device by a coating method.
  • Another object of the present invention is to provide a composition for producing an organic EL device, which can form an organic EL device on a plastic substrate by a coating method.
  • the following solvent (A) and solvent (B) exhibit high solubility in organic semiconductor materials even at relatively low temperatures, and organic EL containing the solvent.
  • the element manufacturing composition can form an organic EL element by applying a printing method, spin coating method, or the like on a plastic substrate having a lower heat resistance than a glass substrate. It has been found that the material crystallizes by self-organizing action. Furthermore, it discovered that a coating property and a drying property could be improved further if the solvent generally used for an electronic material use was mixed with the said solvent as needed. The present invention has been completed based on these findings.
  • the present invention is a solvent for dissolving an organic semiconductor material, which has the following formula (a): (Wherein R 1 to R 4 are the same or different and are C 1-2 alkyl groups. R 1 and R 4 are bonded to each other to form —N (R 2 ) —C ( ⁇ O) — N (R 3 )-may form a ring) And / or the following formula (b) [Wherein, ring Z represents a ring selected from an aromatic carbocyclic ring, a 5- to 7-membered alicyclic carbocyclic ring, and a 5- to 7-membered heterocyclic ring.
  • R 5 represents an oxo group ( ⁇ O), a thioxy group ( ⁇ S), a —OR a group, a —SR a group, a —O (C ⁇ O) R a group, a —R b O (C ⁇ O) R a group.
  • R a represents a C 1-7 alkyl group, an aryl group, or a group in which the group is bonded via a single bond or a linking group
  • R b represents a C 1-7 alkylene group, an arylene group, or the group described above.
  • R 6 represents a hydrogen atom, a C 1-7 alkyl group, an aryl group, and —OR A group selected from a group (R a is as defined above).
  • R 5 and R 6 may be bonded to each other to form a ring together with the carbon atoms constituting ring Z]
  • the solvent for organic electroluminescent element manufacture containing the solvent (B) represented by these is provided.
  • the solvent (A) is 1,1,3,3-tetramethylurea, 1,3-dimethyl-2-imidazolidinone, and 1,3-dimethyl-3,4,5,6.
  • the solvent for producing an organic electroluminescence device which is at least one selected from tetrahydro-2 (1H) pyrimidinone.
  • the solvent (B) may be 2-cyclopentylcyclopentanone, 2-pentylcyclopentanone, 2,3-dihydrobenzofuran, 2,3-dihydro-2-methylbenzofuran, cyclohexyl acetate, 2-methyl
  • the aforementioned is at least one selected from cyclohexyl acetate, 4-t-butylcyclohexyl acetate, 1,2,3,4-tetrahydronaphthalene, 1-oxo-1,2,3,4-tetrahydronaphthalene, and phenylcyclohexane
  • a solvent for producing an organic electroluminescence device is provided.
  • the present invention also provides the organic electroluminescent element manufacturing solvent, wherein the organic semiconductor material is a compound having a structural unit represented by the following formula (1) and / or a compound represented by the following formula (2).
  • the organic semiconductor material is a compound having a structural unit represented by the following formula (1) and / or a compound represented by the following formula (2).
  • Ar 1 may have a substituent, and is a structure selected from an aromatic carbocyclic ring, an aromatic heterocyclic ring, and a ring in which two or more thereof are bonded via a single bond or a linking group.
  • Ar 2 is an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these which may have a substituent, each having a single bond or a linking group.
  • m and n are the same or different and each represents an integer of 1 or more, m Ar 1 and n Ar 2 may be the same or different) (Wherein Ar 3 to Ar 5 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these via a single bond or a linking group.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-1) or a compound represented by the following formula (2-2).
  • a manufacturing solvent is provided.
  • Ar 6 may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these bonded via a single bond or a linking group.
  • a group in which two hydrogen atoms are removed from a structural formula selected from a ring, Ar 7 to Ar 10 are the same or different and may have a substituent, an aromatic carbocycle, an aromatic heterocycle;
  • a group in which one hydrogen atom is removed from a structural formula selected from a ring and a ring in which two or more of these are bonded via a single bond or a linking group is shown.
  • Ar 11 to Ar 13 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these are a single bond or A group obtained by removing two hydrogen atoms from a structural formula selected from a ring bonded through a linking group, Ar 14 to Ar 19 may be the same or different and may have a substituent. A group obtained by removing one hydrogen atom from a structural formula selected from aromatic carbocycles, aromatic heterocycles, and rings in which two or more of these are bonded via a single bond or a linking group)
  • the present invention also provides a compound in which the organic semiconductor material has a structural unit represented by the following formula (1-1), a compound represented by the following formula (2-1-1) to (2-1-5) And the above-mentioned solvent for producing an organic electroluminescence device, which is at least one compound selected from compounds represented by the following formula (2-2-1).
  • the present invention also provides a composition for producing an organic electroluminescence device comprising an organic semiconductor material and the above-mentioned solvent for producing an organic electroluminescence device.
  • the organic semiconductor material is a compound having a structural unit represented by the following formula (1) and / or a compound represented by the following formula (2).
  • Ar 1 may have a substituent, and is a structure selected from an aromatic carbocyclic ring, an aromatic heterocyclic ring, and a ring in which two or more thereof are bonded via a single bond or a linking group.
  • a group in which two hydrogen atoms are removed from the formula, Ar 2 is an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these which may have a substituent, each having a single bond or a linking group.
  • m and n are the same or different and each represents an integer of 1 or more, m Ar 1 and n Ar 2 may be the same or different) (Wherein Ar 3 to Ar 5 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these via a single bond or a linking group.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-1) or a compound represented by the following formula (2-2).
  • a manufacturing composition is provided.
  • Ar 6 may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these bonded via a single bond or a linking group.
  • a group in which two hydrogen atoms are removed from a structural formula selected from a ring, Ar 7 to Ar 10 are the same or different and may have a substituent, an aromatic carbocycle, an aromatic heterocycle;
  • a group in which one hydrogen atom is removed from a structural formula selected from a ring and a ring in which two or more of these are bonded via a single bond or a linking group is shown.
  • Ar 11 to Ar 13 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these are a single bond or A group obtained by removing two hydrogen atoms from a structural formula selected from a ring bonded through a linking group, Ar 14 to Ar 19 may be the same or different and may have a substituent. A group obtained by removing one hydrogen atom from a structural formula selected from aromatic carbocycles, aromatic heterocycles, and rings in which two or more of these are bonded via a single bond or a linking group)
  • the present invention also provides a compound in which the organic semiconductor material has a structural unit represented by the following formula (1-1), a compound represented by the following formula (2-1-1) to (2-1-5) And the above-mentioned composition for producing an organic electroluminescence device, which is at least one compound selected from the compounds represented by the following formula (2-2-1).
  • a solvent for dissolving an organic semiconductor material which comprises a solvent (A) represented by formula (a) and / or a solvent (B) represented by formula (b).
  • the solvent (A) is 1,1,3,3-tetramethylurea, 1,3-dimethyl-2-imidazolidinone, and 1,3-dimethyl-3,4,5,6-tetrahydro-
  • the solvent for producing an organic EL device according to [1] which is at least one selected from 2 (1H) pyrimidinone.
  • the solvent (B) is 2-cyclopentylcyclopentanone, 2-pentylcyclopentanone, 2,3-dihydrobenzofuran, 2,3-dihydro-2-methylbenzofuran, cyclohexyl acetate, 2-methylcyclohexyl acetate, [1] to at least one selected from 4-t-butylcyclohexyl acetate, 1,2,3,4-tetrahydronaphthalene, 1-oxo-1,2,3,4-tetrahydronaphthalene, and phenylcyclohexane [3] The solvent for producing an organic EL device according to any one of [3].
  • a compound in which the organic semiconductor material has a structural unit represented by formula (1-1), compounds represented by formulas (2-1-1) to (2-1-5), and formula (2 -2-1) The composition for producing an organic EL device according to any one of [10] to [12], which is at least one compound selected from the compounds represented by -2-1): [14] The organic EL device according to any one of [10] to [13], wherein the content of the solvent for producing an organic EL device is 50.0 to 99.99% by weight of the total amount of the composition for producing an organic EL device.
  • the solvent for producing an organic EL device of the present invention has high organic semiconductor material solubility even at a relatively low temperature.
  • the composition for organic EL element manufacture of this invention contains the said solvent for organic EL element manufacture, although heat resistance is low compared with a glass substrate, it is a shock-resistant, lightweight and flexible plastic substrate printing method
  • the organic EL element can be directly formed by using a coating method such as spin coating or the like, and a light-weight and flexible display or computer device that is resistant to impact can be formed while greatly reducing costs.
  • the composition for manufacturing an organic EL device of the present invention is applied on a substrate, the organic semiconductor material is crystallized by a self-organizing action, so that an organic semiconductor crystal thin film having high crystallinity is obtained.
  • solvent (A) in the present invention is represented by the above formula (a).
  • R 1 to R 4 are the same or different and are C 1-2 (C 1-2 ) alkyl group. R 1 and R 4 may be bonded to each other to form a ring together with —N (R 2 ) —C ( ⁇ O) —N (R 3 ) — in the formula.
  • the C 1-2 alkyl group in R 1 to R 4 is a methyl group or an ethyl group.
  • Examples of the ring formed by combining R 1 and R 4 together with —N (R 2 ) —C ( ⁇ O) —N (R 3 ) — in the formula include a 2-imidazolidinone ring, 3, Examples include 4,5,6-tetrahydro-2 (1H) pyrimidinone ring.
  • Examples of the solvent (A) in the present invention include 1,1,3,3-tetramethylurea, 1,1,3,3-tetraethylurea, 1,3-dimethyl-2-imidazolidinone, 1,3 -Dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone and the like. These can be used individually by 1 type or in combination of 2 or more types.
  • the solvent for organic EL element production contains the solvent (A) and does not contain the solvent (B) described later
  • the content of the solvent (A) in the total amount of organic EL element production solvent (100% by weight) is, for example, 50% by weight or more (for example, 50 to 100% by weight), preferably 70% by weight or more (for example 70 to 100% by weight), and particularly preferably 80% by weight or more (for example, 80 to 100% by weight), most preferably 90% by weight or more (for example, 90 to 100% by weight).
  • content of a solvent (A) is less than the said range, there exists a tendency for the solubility of an organic-semiconductor material to fall.
  • the solvent (B) in the present invention is a compound containing at least one heteroatom represented by the above formula (b).
  • ring Z represents a ring selected from an aromatic carbocyclic ring, a 5- to 7-membered alicyclic carbocyclic ring, and a 5- to 7-membered heterocyclic ring.
  • the ring examples include an aromatic carbocyclic ring such as a benzene ring; a 5- to 7-membered alicyclic carbocyclic ring (particularly a 5- to 7-membered alkane ring) such as a pentane ring, a hexane ring, and a heptane ring; And 5- to 7-membered heterocycles such as oxolane ring and thiolane ring.
  • aromatic carbocyclic ring such as a benzene ring
  • a 5- to 7-membered alicyclic carbocyclic ring such as a pentane ring, a hexane ring, and a heptane ring
  • 5- to 7-membered heterocycles such as oxolane ring and thiolane ring.
  • R 5 represents an oxo group ( ⁇ O), a thioxy group ( ⁇ S), a —OR a group, a —SR a group, a —O (C ⁇ O) R a group, a —R b O (C ⁇ O) R a group
  • R a represents a C 1-7 alkyl group, an aryl group, or a group in which the group is bonded via a single bond or a linking group
  • R b represents a C 1-7 alkylene group, or An arylene group or a group in which the group is bonded via a single bond or a linking group
  • R 6 represents a group selected from a hydrogen atom, a C 1-7 alkyl group, an aryl group, and an —OR a group (R a is as defined above).
  • Examples of the C 1-7 alkyl group include linear or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups, and C 3-7 carbon atoms such as cyclopentyl groups.
  • a cycloalkyl group can be mentioned.
  • Examples of the aryl group include a phenyl group.
  • Examples of the C 1-7 alkylene group include linear or branched alkylene groups such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, and trimethylene groups, 1,2-cyclopentylene groups, , 3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group, cyclohexylidene group, etc.
  • An alkylene group (including a cycloalkylidene group) and the like can be mentioned.
  • Examples of the arylene group include a phenylene group.
  • linking group examples include a divalent hydrocarbon group, a carbonyl group (—CO—), an ether bond (—O—), a thioether bond (—S—), an ester bond (—COO—), an amide bond ( -CONH-), carbonate bond (-OCOO-), and a group in which a plurality of these are bonded.
  • Examples of the divalent hydrocarbon group include a linear or branched C 1-18 alkylene group such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group, 2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group, cyclohexylidene group, etc. And a C 3-18 cycloalkylene group (including a cycloalkylidene group).
  • a linear or branched C 1-18 alkylene group such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group, 2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group
  • substituted or unsubstituted amino group examples include an amino group; a mono- or di (C 1-3 ) alkyl-substituted amino group such as a methylamino group, an ethylamino group, an isopropylamino group, a dimethylamino group, and a diethylamino group. Can be mentioned.
  • Examples of the ring that R 5 and R 6 may be bonded together to form a carbon atom constituting the ring Z include, for example, cyclopentane, cyclohexane, cycloheptane, benzene, methylbenzene, thiophene, methylthiophene, furan, Mention may be made of methylfuran, dihydrofuran, methyldihydrofuran and the like.
  • the weight average molecular weight of the solvent (B) represented by the formula (b) is, for example, about 350 or less, preferably 70 to 250, particularly preferably 80 to 200.
  • Examples of the solvent (B) in the present invention include 2-methylcyclopentanone, 2-methylcyclohexanone, cyclohexylmethyl ether, cyclohexylamine, methoxybenzene, 1,2-dimethoxybenzene, 2,3-dihydrobenzofuran, 2, 3-dihydro-3-methylbenzofuran, 2-cyclopentylcyclopentanone, 2-pentylcyclopentanone, 2,3-dihydro-2-methylbenzofuran, cyclohexyl acetate, 1-methylcyclohexyl acetate, 4-t-butylcyclohexyl acetate 2-methylcyclohexyl acetate, 1,2,3,4-tetrahydronaphthalene, 1-oxo-1,2,3,4-tetrahydronaphthalene, phenylcyclohexane and the like. These can be used alone or in combination of two or more.
  • the solvent for organic EL device production contains the solvent (B) and does not contain the above-mentioned solvent (A)
  • the content of the solvent (B) in the total amount (100% by weight) of the organic EL device production solvent of the present invention ( The total amount in the case of containing two or more in combination is, for example, 50% by weight or more (eg 50 to 100% by weight), preferably 70% by weight or more (eg 70 to 100% by weight), particularly preferably 80% by weight. Or more (for example, 80 to 100% by weight), most preferably 90% by weight or more (for example, 90 to 100% by weight).
  • content of a solvent (B) is less than the said range, there exists a tendency for the solubility of an organic-semiconductor material to fall.
  • the solvent for organic EL element manufacture contains a solvent (A) and a solvent (B)
  • the content of the solvent (A) and the solvent (B) in the total amount (100% by weight) of the solvent for organic EL element manufacture of the present invention The sum of the amounts is, for example, 50% by weight or more (eg 50 to 100% by weight), preferably 70% by weight or more (eg 70 to 100% by weight), particularly preferably 80% by weight or more (eg 80 to 100% by weight), Most preferably, it is 90% by weight or more (for example, 90 to 100% by weight).
  • the solubility of the organic semiconductor material tends to decrease.
  • solvent (C) examples include (mono, di, tri) alkylene glycol monoalkyl ether, (mono, di) alkylene glycol dialkyl ether, (mono, di) alkylene glycol alkyl ether acetate, and (mono, di) alkylene glycol.
  • Rukoto can. These can be used alone or in combination of two or more.
  • Examples of the (mono, di, tri) alkylene glycol monoalkyl ether include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.
  • Examples of the (mono, di) alkylene glycol dialkyl ether include ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, Propylene glycol dimethyl ether, dipropylene glycol diethyl ether, propylene glycol methyl ethyl ether, propylene glycol methyl n-propyl ether, propylene glycol methyl n-butyl ether, dipropylene glycol methyl ethyl ether, dipropylene glycol methyl n Propyl ether, and dipropylene glycol methyl n- butyl ether.
  • Examples of the (mono, di) alkylene glycol alkyl ether acetate include ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl Ether acetate, diethylene glycol monopropyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether Acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monopropyl ether acetate, and dipropylene glycol monobutyl ether acetate and the like
  • Examples of the (mono, di) alkylene glycol diacetate include ethylene glycol diacetate, diethylene glycol diacetate, propylene glycol diacetate, and dipropylene glycol diacetate.
  • Examples of the (cyclo) alkyl acetate include methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, and butyl acetate.
  • Examples of the C 3-6 alcohol include n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-pentyl alcohol, n-hexyl alcohol, and 2-hexyl alcohol. Can be mentioned.
  • Examples of the C 3-6 alkanediol include 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, and the like.
  • Examples of the C 3-6 alkanediol monoalkyl ether include 3-methoxybutanol.
  • Examples of the C 3-6 alkanediol alkyl ether acetate include 3-methoxybutanol acetate.
  • Examples of the C 3-6 alkanediol diacetate include 1,3-butanediol diacetate, 1,4-butanediol diacetate, and 1,6-hexanediol diacetate.
  • hydroxycarboxylic acid ester examples include methyl lactate and ethyl lactate.
  • hydroxycarboxylic acid diester examples include methyl lactate acetate and ethyl lactate acetate.
  • alkoxycarboxylic acid ester examples include methyl methoxypropionate and ethyl ethoxypropionate.
  • Examples of the cyclic ketone include 4-ketoisophorone.
  • lactones examples include ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -caprolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -acetyl- ⁇ -butyrolactone, and the like.
  • Examples of the cyclic ether include tetrahydrofuran and tetrahydrofurfuryl alcohol.
  • amides examples include dimethylformamide.
  • pyridines examples include pyridine and methylpyridine.
  • aromatic ether examples include veratrol.
  • amines examples include diethylamine and triethylamine.
  • the organic semiconductor material is contained at a high concentration, and coating property, drying property, safety, dispersion
  • the composition for organic EL device manufacture excellent in property, solubility, etc. can be formed.
  • one or more solvents selected from mono C 3-6 alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and C 3-6 alkanediol alkyl ether acetates are used. It is effective to use together.
  • mono C 3-6 alkylene glycol monoalkyl ethers such as propylene glycol monomethyl ether
  • mono-C 3-6 alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate
  • C 3-6 One or two solvents selected from alkanediol monoalkyl ether, C 3-6 alkanediol alkyl ether acetate, hydroxycarboxylic acid ester, hydroxycarboxylic acid diester, C 3-6 alcohol, and C 3-6 alkanediol The combined use is effective.
  • (mono, di) C 3 such as propylene glycol methyl n-propyl ether, propylene glycol methyl n-butyl ether, dipropylene glycol methyl n-propyl ether, dipropylene glycol methyl n-butyl ether, etc. It is effective to use one or more solvents selected from -6 alkylene glycol C 1-2 alkyl C 3-4 alkyl ether and (cyclo) alkyl acetate.
  • the mixing ratio ([solvent (A) + solvent (B)] / [solvent (C)]; weight ratio) is: For example, it is 95/5 to 50/50, preferably 95/5 to 70/30.
  • the ratio of the solvent (C) is higher than that of the solvent (A) and / or the solvent (B), the solubility of the organic semiconductor material tends to decrease.
  • the solvent for producing the organic EL device of the present invention may contain a conventionally used solvent such as toluene, but the content of toluene or the like is, for example, 10% of the total amount of the solvent for producing the organic EL device of the present invention. % By weight or less, preferably 5% by weight or less, particularly preferably 1% by weight or less. If the content of toluene or the like exceeds the above range, safety is lowered, which is not preferable.
  • the solvent for producing an organic EL device of the present invention contains a solvent (A) and / or a solvent (B), it has a high solubility in organic semiconductor materials even at a relatively low temperature.
  • the solubility of the compound having the structural unit represented by the formula (1) at 100 ° C. is, for example, 0.1 part by weight or more, preferably 1 part by weight or more with respect to 100 parts by weight of the organic EL element production solvent. Preferably it is 2 parts by weight or more.
  • the upper limit of solubility is, for example, 30 parts by weight, preferably 20 parts by weight, particularly preferably 15 parts by weight.
  • solubility is, for example, 0.1 part by weight or more, preferably 1 part by weight or more with respect to 100 parts by weight of the solvent for organic EL device production. Preferably it is 2 parts by weight or more.
  • the upper limit of solubility is, for example, 50 parts by weight, preferably 45 parts by weight, particularly preferably 40 parts by weight.
  • the solvent for producing an organic EL element of the present invention is a solvent for dissolving an organic semiconductor material, more specifically, a composition containing the organic semiconductor material dissolved is applied onto a substrate (for example, printing such as ink jet printing). It is a solvent used for dissolving an organic semiconductor material when forming an organic EL device by applying a method such as a spin coating method or a spin coating method.
  • a method such as a spin coating method or a spin coating method.
  • the compound which has a structural unit represented by following formula (1), and / or the compound represented by following formula (2) is preferable. These can be used alone or in combination of two or more.
  • Ar 1 may have a substituent, and is a structure selected from an aromatic carbocyclic ring, an aromatic heterocyclic ring, and a ring in which two or more thereof are bonded via a single bond or a linking group.
  • a group in which two hydrogen atoms are removed from the formula, Ar 2 is an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these which may have a substituent, each having a single bond or a linking group.
  • m and n are the same or different and each represents an integer of 1 or more, m Ar 1 and n Ar 2 may be the same or different) (Wherein Ar 3 to Ar 5 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these via a single bond or a linking group.
  • aromatic carbocycle examples include two benzene rings, indene rings, naphthalene rings, fluorene rings, anthracene rings, phenanthrene rings, perylene rings, tetracene rings, pyrene rings, benzpyrene rings, chrysene rings, and triphenylene rings.
  • aromatic carbocycles examples include polycyclic aromatic carbocycles having 9 to 20 carbon atoms in which the above (preferably 2 to 5) rings are condensed.
  • aromatic heterocycle examples include a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, and a pyrrolopyrazole ring.
  • linking group examples include a divalent hydrocarbon group, a carbonyl group (—CO—), an ether bond (—O—), a thioether bond (—S—), an ester bond (—COO—), an amide bond ( -CONH-), carbonate bond (-OCOO-), and a group in which a plurality of these are bonded.
  • divalent hydrocarbon group examples include, for example, a C 1-4 alkylene group such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group, a 1,2-cyclopentylene group, C 3-18 cycloalkylene such as 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group, cyclohexylidene group, etc.
  • aromatic carbocycle The aromatic carbocycle, the aromatic heterocycle, or a ring in which two or more of these are bonded through a single bond or a linking group (hereinafter sometimes referred to as “aromatic carbocycle etc.”)
  • Suitable substituents include, for example, C 1-12 (preferably C 1-6 ) alkyl groups such as methyl and ethyl groups; C 2-12 (preferably C 2-6 ) alkenyls such as vinyl groups.
  • C 10-24 (preferably C 12-24 ) N, N-diarylamino group; C 7-36 (preferably C 7-24 ) N-aryl-N-alkylamino group such as phenylmethylamino group
  • An acyl group of C 2-24 such as acetyl group or benzoyl group; a halogen atom such as fluorine atom or chlorine atom; C 1-12 such as trifluoromethyl group (preferably C 1- 6 ) a haloalkyl group; a C 1-24 (preferably C 1-12 ) alkylthio group such as a methylthio group or an ethylthio group; a C 4-36 (preferably C 5-24) such as a phenylthio group, a naphthylthio group or a pyridylthio group.
  • Arylthio group or Roariruchio group trialkylsiloxy group C 1-10 (preferably C 1-5) such as trimethylsiloxy group; a trimethylsilyl group, a silyl group of C 2-36 (preferably C 3-24) such as triphenylsilyl group
  • a hydrocarbon group a C 3-36 (preferably C 4-24 ) aromatic heterocyclic group such as a thienyl group and a pyridyl group.
  • the substituent may further have a substituent (for example, the substituents exemplified above).
  • Substituents possessed by the aromatic carbocycle and the like may be bonded together to form a ring together with carbon atoms constituting the aromatic carbocycle and the like.
  • the molecular weight of the substituent that the aromatic carbocycle or the like may have is preferably 500 or less, particularly preferably 250 or less.
  • Ar 1 is a structural formula of an aromatic carbocycle and / or an aromatic heterocycle, which may have a substituent, in that the hole injection property is increased and the driving voltage of the resulting device is decreased.
  • 2 or more aromatic carbocycles and / or aromatic heterocycles (for example, 2 to 5, preferably 2 to 3) which may have the above-described substituent and a group obtained by removing 2 hydrogen atoms from A group in which two hydrogen atoms are removed from the structural formula formed by bonding, particularly from the structural formula selected from a biphenyl ring, a terphenyl ring, and a fluorene ring, which may have a substituent.
  • a group from which two hydrogen atoms have been removed is preferred because of its excellent solubility.
  • the substituent is preferably a C 1-12 alkyl group or a C 1-12 alkoxy group.
  • Ar 2 is preferably a group in which one hydrogen atom is removed from the structural formula of an aromatic carbocyclic ring (particularly a benzene ring) which may have a substituent, from the viewpoint of excellent solubility.
  • the substituent is preferably a C 1-12 alkyl group or a C 1-12 alkoxy group.
  • m and n are integers of 1 or more (for example, 1 to 3). It is preferable that m is 1 and n is 1 in that the hole injection property to the adjacent hole transport layer or the light emitting layer is increased and the driving voltage of the resulting device is decreased. It is preferable that m is 1 and n is 3 in that radical cations are stably generated, the hole injection property from the electrode is high, and the driving voltage of the resulting device is low.
  • the two structural units enclosed in parentheses in the above formula (1) may be block polymerized or random polymerized.
  • the number of repetitions of the structural unit represented by the above formula (1) is, for example, about 7 to 300, and the structure represented by the above formula (1)
  • the compound having a unit has a weight average molecular weight (in terms of polystyrene by GPC) of, for example, about 5,000 to 200,000, preferably 10,000 to 100,000.
  • Ar 3 to Ar 5 each have a group obtained by removing one hydrogen atom from the structural formula of an aromatic carbocyclic ring (in particular, a benzene ring) which may have a substituent, or a substituent.
  • a group in which one hydrogen atom is removed from the structural formula of an aromatic heterocyclic ring (particularly a carbazole ring) which may be used is preferable.
  • the substituent is preferably a C 1-12 (preferably C 1-6 ) alkyl group and / or a C 10-24 (preferably C 12-24 ) diarylamino group.
  • the substituents may be bonded to each other to form a ring together with the nitrogen atom in the formula (2).
  • the molecular weight of the compound represented by the above formula (2) is, for example, about 300 to 5000, preferably 450 to 3000, particularly preferably 450 to 1000.
  • the compound represented by the formula (2) is preferably a compound selected from a compound represented by the following formula (2-1) and a compound represented by the following formula (2-2).
  • Ar 6 may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these bonded via a single bond or a linking group.
  • a group in which two hydrogen atoms are removed from a structural formula selected from a ring, Ar 7 to Ar 10 are the same or different and may have a substituent, an aromatic carbocycle, an aromatic heterocycle;
  • a group in which one hydrogen atom is removed from a structural formula selected from a ring and a ring in which two or more of these are bonded via a single bond or a linking group is shown.
  • Ar 11 to Ar 13 are the same or different and each may have a substituent, an aromatic carbocyclic ring, an aromatic heterocyclic ring, and two or more of these are a single bond or A group obtained by removing two hydrogen atoms from a structural formula selected from a ring bonded through a linking group, Ar 14 to Ar 19 may be the same or different and may have a substituent. A group obtained by removing one hydrogen atom from a structural formula selected from aromatic carbocycles, aromatic heterocycles, and rings in which two or more of these are bonded via a single bond or a linking group)
  • Examples of Ar 6 and Ar 11 to Ar 13 include the same examples as Ar 1 described above.
  • Examples of Ar 7 to Ar 10 and Ar 14 to Ar 19 include the same examples as Ar 3 to Ar 5 described above.
  • Ar 6 is a group in which two hydrogen atoms are removed from the structural formula of an aromatic carbocyclic ring (for example, benzene ring), or two or more (for example 2 Structural formula (for example, biphenyl ring, terphenyl ring structural formula) in which up to 5, preferably 2 to 3 aromatic carbocyclic rings (for example, benzene ring) are bonded via a single bond or a linking group A group in which two hydrogen atoms are removed from is preferable.
  • an aromatic carbocyclic ring for example, benzene ring
  • 2 Structural formula for example, biphenyl ring, terphenyl ring structural formula
  • up to 5, preferably 2 to 3 aromatic carbocyclic rings (for example, benzene ring) are bonded via a single bond or a linking group
  • a group in which two hydrogen atoms are removed from is preferable.
  • Ar 7 to Ar 10 are, among others, a group in which one hydrogen atom is removed from the structural formula of an aromatic carbocyclic ring (in particular, a benzene ring, a phenanthrene ring or an anthracene ring) which may have a substituent, Or the group remove
  • the substituent is preferably a C 1-12 (preferably C 1-6 ) alkyl group and / or a C 6-16 (preferably C 6-10 ) aryl group.
  • Ar 7 and Ar 8 , and Ar 9 and Ar 10 may be bonded to each other to form a ring together with the nitrogen atom to which these Ar groups are bonded.
  • Ar 11 to Ar 13 are particularly preferably groups obtained by removing two hydrogen atoms from the structural formula of an aromatic carbocyclic ring (particularly a benzene ring) which may have a substituent.
  • Ar 14 to Ar 19 are particularly preferably groups in which one hydrogen atom has been removed from the structural formula of an aromatic carbocyclic ring (in particular, a benzene ring) which may have a substituent.
  • the substituent is preferably a C 1-12 (preferably C 1-6 ) alkyl group.
  • Ar 14 and Ar 15 , Ar 16 and Ar 17 , and Ar 18 and Ar 19 may be bonded to each other to form a ring together with the nitrogen atom to which these Ar groups are bonded.
  • organic semiconductor material in the present invention in particular, a compound having a structural unit represented by the following formula (1-1), a compound represented by the following formulas (2-1-1) to (2-1-5), And at least one compound selected from compounds represented by the following formula (2-2-1) is preferred.
  • composition for manufacturing organic EL device is a composition used to form an organic EL device by coating on a substrate (for example, coating by a printing method such as inkjet printing or a spin coating method). And it contains the said organic-semiconductor material and the solvent for organic electroluminescent element manufacture, It is characterized by the above-mentioned.
  • the composition for producing an organic EL device of the present invention is prepared, for example, by mixing the organic semiconductor material and the solvent for producing an organic EL device, and in the atmosphere at a temperature of about 70 to 150 ° C. for 0.1 to 10 hours. It can be prepared by heating to a certain extent.
  • the content of the organic semiconductor material in the composition for producing an organic EL element of the present invention is, for example, when the compound having the structural unit represented by the formula (1-1) is used as the organic semiconductor material.
  • 0.1 part by weight or more preferably 1.0 part by weight or more, and particularly preferably 2.0 part by weight or more with respect to 100 parts by weight of the device manufacturing solvent.
  • the upper limit is, for example, 30 parts by weight, preferably 20 parts by weight, particularly preferably 15 parts by weight.
  • the content of the organic semiconductor material in the composition for manufacturing an organic EL element of the present invention is organic EL element manufacturing.
  • the upper limit is, for example, 30 parts by weight, preferably 20 parts by weight, particularly preferably 15 parts by weight.
  • the content of the organic semiconductor material in the composition for manufacturing an organic EL element of the present invention is organic EL element manufacturing.
  • the upper limit is, for example, 50 parts by weight, preferably 45 parts by weight, particularly preferably 40 parts by weight.
  • the content of the solvent for producing an organic EL element in the composition for producing an organic EL element of the present invention is, for example, 99.99% by weight or less.
  • the lower limit is, for example, 50.0% by weight, preferably 55.0% by weight, particularly preferably 60.0% by weight, and the upper limit is preferably 99.0% by weight, particularly preferably 98.0% by weight. is there.
  • the organic EL device manufacturing solvent content contained in the organic EL device manufacturing composition of the present invention can promote crystallization by the self-organizing action of the organic semiconductor material. It is preferably 1 time (weight) or more, more preferably 1.2 times (weight) or more, and particularly preferably 1.5 times (weight) or more.
  • the upper limit is, for example, 1000 times (weight), preferably 100 times (weight), particularly preferably 50 times (weight).
  • composition for producing an organic EL device of the present invention in addition to the organic semiconductor material and the solvent for producing the organic EL device, components contained in a general composition for producing an organic EL device (for example, epoxy resin, acrylic resin) Resin, cellulose resin, butyral resin, etc.) can be blended as needed.
  • a general composition for producing an organic EL device for example, epoxy resin, acrylic resin
  • Resin for example, cellulose resin, butyral resin, etc.
  • the composition for producing an organic EL device of the present invention can dissolve an organic semiconductor material at a high concentration even at a relatively low temperature. Therefore, although it has lower heat resistance than glass substrates, it can withstand impacts and can directly form organic EL elements on lightweight and flexible plastic substrates, forming impact-resistant, lightweight and flexible displays and computer equipment. can do. Moreover, since the composition for manufacturing an organic EL device of the present invention contains the solvent for manufacturing an organic EL device of the present invention, when applied on a substrate, the organic semiconductor material is crystallized by a self-organizing action and has high crystallinity. A crystal thin film (for example, an organic EL element) is obtained. Furthermore, the organic semiconductor crystal thin film can be easily formed by a simple coating method such as a printing method or a spin coating method, and the cost can be greatly reduced.
  • Example 1 A compound having a structural unit represented by the above formula (1-1) as an organic semiconductor material (poly [(9,9-dioctylfluoronyl-2,7-diyl) -co- (4,4′-N— ( 4-sec-butylphenyl) diphenylamine)], weight average molecular weight: 40000, manufactured by Aldrich Co., Ltd. (hereinafter, sometimes referred to as “TFB”), and 4-t-butyl as a solvent for organic EL device production Cyclohexyl acetate (trade name “BCHXA”, manufactured by Daicel Corporation) was used. Under a 20 ° C.
  • an organic semiconductor material was dispersed in a solvent for producing an organic EL device so that the concentration thereof was 2 wt% to 9 wt%. Then, the composition for organic EL element manufacture was obtained by heating at 100 degreeC for 2 hours under nitrogen atmosphere and light-shielding conditions. The insoluble matter in the obtained composition for manufacturing an organic EL device was visually confirmed, and the solubility of the organic semiconductor material was evaluated according to the following criteria. Evaluation criteria When no insoluble matter is confirmed: ⁇ (Good solubility) When insoluble matter is confirmed: x (poor solubility)
  • Examples 2 to 5 and Comparative Examples 1 to 3 Except having used the solvent for organic EL element manufacture shown in Table 1, the composition for organic EL element manufacture was prepared like Example 1, and the solubility of the organic-semiconductor material was evaluated.
  • BCHXA 4-t-butylcyclohexyl acetate (manufactured by Daicel Corporation)
  • MCHXA 2-methylcyclohexyl acetate (manufactured by Daicel Corporation)
  • THNO 1-oxo-1,2,3,4-tetrahydronaphthalene (manufactured by Daicel Corporation)
  • PECPAN 2-pentylcyclopentanone (manufactured by Daicel Corporation)
  • CCPPAN 2-cyclopentylcyclopentanone (manufactured by Daicel Corporation)
  • Xyl o-xylene (manufactured by Tokyo Chemical Industry Co., Ltd.)
  • ANON cyclohexanone (manufactured by Tokyo Chemical Industry Co., Ltd.)
  • Example 6 Compound (4,4 ′, 4 ′′ -tris [phenyl (m-tolyl) amino] triphenylamine represented by the above formula (2-2-1) as an organic semiconductor material, molecular weight: 789, manufactured by Aldrich Co., Ltd. (Hereinafter, sometimes referred to as “TFA”), and 2,3-dihydro-2-methylbenzofuran (trade name “DHMBF”, manufactured by Daicel Corporation) was used as a solvent for producing an organic EL device. Under a 20 ° C. environment, an organic semiconductor material was dispersed in a solvent for producing an organic EL device so that the concentration thereof was 10 wt% to 30 wt%.
  • composition for organic EL element manufacture was obtained by heating at 100 degreeC for 2 hours under nitrogen atmosphere and light-shielding conditions.
  • the insoluble matter in the obtained composition for manufacturing an organic EL device was visually confirmed, and the solubility of the organic semiconductor material was evaluated based on the above criteria.
  • DHMBF 2,3-dihydro-2-methylbenzofuran (manufactured by Daicel Corporation)
  • THN 1,2,3,4-tetrahydronaphthalene (manufactured by Daicel Corporation)
  • THNO 1-oxo-1,2,3,4-tetrahydronaphthalene (manufactured by Daicel Corporation)
  • PCH Phenylcyclohexane (manufactured by Daicel Corporation)
  • DMTHP 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (manufactured by Daicel Corporation)
  • CCPPAN 2-cyclopentylcyclopentanone (manufactured by Daicel Corporation)
  • CHXA cyclohexyl acetate (manufactured by Daicel Corporation)
  • DMI 1,3-dimethyl-2-imidazolidinone (manufactured by Daicel Corporation)
  • Example 14 As an organic semiconductor material, a compound represented by the above formula (2-1-1) (4,4′-bis (N-carbazolyl) -1,1′-biphenyl, molecular weight: 485, manufactured by Aldrich Co., Ltd., 1) -oxo-1,2,3,4-tetrahydronaphthalene (trade name “THNO”, manufactured by Daicel Corporation) was used as a solvent for producing organic EL elements. . Under a 20 ° C. environment, an organic semiconductor material was dispersed in a solvent for producing an organic EL element so that its concentration was 2 wt% to 10 wt%.
  • composition for organic EL element manufacture was obtained by heating at 100 degreeC for 2 hours under nitrogen atmosphere and light-shielding conditions.
  • the insoluble matter in the obtained composition for manufacturing an organic EL device was visually confirmed, and the solubility of the organic semiconductor material was evaluated based on the above criteria.
  • THNO 1-oxo-1,2,3,4-tetrahydronaphthalene (manufactured by Daicel Corporation)
  • DMTHP 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (manufactured by Daicel Corporation)
  • CCPPAN 2-cyclopentylcyclopentanone (manufactured by Daicel Corporation)
  • THN 1,2,3,4-tetrahydronaphthalene (manufactured by Daicel Corporation)
  • DHMBF 2,3-dihydro-2-methylbenzofuran (manufactured by Daicel Corporation)
  • DMI 1,3-dimethyl-2-imidazolidinone (manufactured by Daicel Corporation)
  • PCH Phenylcyclohexane (manufactured by Daicel Corporation)
  • Tol Toluene (Tokyo Chemical Industry Co., Ltd.)
  • Xyl o
  • organic semiconductor materials equivalent to or better than toluene, xylene and cyclohexanone for example, compounds represented by the formulas (1) and (2), particularly poly [(9,9-dioctylfluoronyl- 2,7-diyl) -co- (4,4′-N- (4-sec-butylphenyl) diphenylamine)] (compound having a structural unit represented by formula (1-1)), 4,4 ′ -Bis (N-carbazolyl) -1,1′-biphenyl (compound represented by the formula (2-1-1)), 4,4 ′, 4 ′′ -tris [phenyl (m-tolyl) amino] triphenyl Amine (compound represented by the formula (2-2-1)) and the like].
  • organic semiconductor materials equivalent to or better than toluene, xylene and cyclohexanone for example, compounds represented by the formulas (1) and (2), particularly poly [(9,9-diocty
  • the solvent for producing an organic EL device of the present invention has high organic semiconductor material solubility even at a relatively low temperature.
  • the composition for organic EL element manufacture of this invention contains the said solvent for organic EL element manufacture, although heat resistance is low compared with a glass substrate, it is a shock-resistant, lightweight and flexible plastic substrate printing method
  • the organic EL element can be directly formed by using a coating method such as spin coating or the like, and a light-weight and flexible display or computer device that is resistant to impact can be formed while greatly reducing costs.
  • the composition for manufacturing an organic EL device of the present invention is applied on a substrate, the organic semiconductor material is crystallized by a self-organizing action, so that an organic semiconductor crystal thin film having high crystallinity is obtained.

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Abstract

La présente invention porte sur : un solvant, permettant la fabrication d'éléments électroluminescents organiques, qui est excellent en termes de dissolution d'un matériau semi-conducteur organique ; et une composition, permettant la fabrication d'éléments électroluminescents organiques, qui contient ledit matériau semi-conducteur organique et le solvant susmentionné permettant la fabrication d'éléments électroluminescents organiques et peut être utilisée pour former un élément électroluminescent organique par le biais d'un procédé de revêtement. Le solvant susmentionné permettant la fabrication d'éléments électroluminescents organiques est un solvant destiné à dissoudre un matériau semi-conducteur organique et est caractérisé par le fait qu'il contient un solvant (A) qui peut être représenté par la formule (a) et/ou un solvant (B) qui peut être représenté par la formule (b). (a) (b)
PCT/JP2015/066703 2014-06-17 2015-06-10 Solvant permettant la fabrication d'éléments électroluminescents organiques Ceased WO2015194429A1 (fr)

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JP2020196721A (ja) * 2017-10-26 2020-12-10 エルジー ディスプレイ カンパニー リミテッド 有機化合物、これを含む発光ダイオードおよび発光装置
JP7088991B2 (ja) 2017-10-26 2022-06-21 エルジー ディスプレイ カンパニー リミテッド 有機化合物、これを含む発光ダイオードおよび発光装置

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