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Organic optical material NEW

外国特許コード F210010321
整理番号 AF29-06WO
掲載日 2021年2月1日
出願国 欧州特許庁(EPO)
出願番号 18848811
公報番号 3674381
出願日 平成30年8月24日(2018.8.24)
公報発行日 令和2年7月1日(2020.7.1)
国際出願番号 JP2018031419
国際公開番号 WO2019039597
国際出願日 平成30年8月24日(2018.8.24)
国際公開日 平成31年2月28日(2019.2.28)
優先権データ
  • 特願2017-161912 (2017.8.25) JP
  • 特願2018-037356 (2018.3.2) JP
  • 2018JP31419 (2018.8.24) WO
発明の名称 (英語) Organic optical material NEW
発明の概要(英語) Provided is a novel donor-acceptor type compound which emits light even in a solid state. The present invention provides an organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein the complex is solid at ordinary temperature; and the organic optical material has a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift having a value corresponding to 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side.
従来技術、競合技術の概要(英語) Background of the Invention
Light emitting organic compounds are used in a wide range of fields such as biological labeling materials, organic electronics materials, chemical sensors, and organic lasers. Novel light emitting materials are under active research and development. In particular, fluorescent organic compounds which emit light by irradiation with X-ray, ultraviolet ray, or visible light may be utilized in organic fluorescent coatings, etc., in addition to the purposes described above.
However, most of molecules generally used as light emitting organic materials are robust and highly planar molecules. Therefore, such molecules intensely emit light in a solution because of less contact or interference between the molecules. By contrast, the molecules in a solid state such as a crystalline state often drastically reduce light emission efficiency because the energy of a released electromagnetic wave is attenuated by the influence of its neighboring planar molecules. Since the light emitting organic materials may be used in a solid state in terms of application, an important challenge thereto is to develop materials which intensely emit light not only in a solution but in a solid state.
Many donor-acceptor type compounds have been reported and are known to exhibit diverse characteristics.
Patent Literature 1 discloses a fluorescence emitting compound comprising a nitrogen-containing aromatic ring having high light emission efficiency not only in a solution state but in a solid state.
Non Patent Literature 1 states that the fluorescence wavelength of a so-called donor-acceptor type compound in which the donor and the acceptor are conjugated with each other can be controlled by causing hydrochloric acid, trifluoroacetic acid, or boron tribromide as an activator to react with the compound.
Non Patent Literature 2 describes various analyses conducted by allowing a boron-containing compound to act on a compound consisting of a dimethylamino group and a pyridine ring, which results in a finding that a dipole moment is increased through the reaction of the nitrogen atom of the pyridine ring with the boron atom. However, the literature does not disclose influence on a fluorescence wavelength.
Citation List
Patent Literature
Patent Literature 1: International Publication No. WO 2014/132704
Non Patent Literature
Non Patent Literature 1: Chem. Sci. 2013, 4, 3288
Non Patent Literature 2: Chem. Mater. 1998, 10, 1355
特許請求の範囲(英語) [claim1]
1. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim2]
2. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the conjugated molecule does not have both one hydrogen atom and one disubstituted amino group at the same time on one of carbon atoms constituting an aliphatic carbon-carbon double bond in its molecule; the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim3]
3. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 15 nm or more from a maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim4]
4. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the conjugated molecule does not have both one hydrogen atom and one disubstituted amino group at the same time on one of carbon atoms constituting an aliphatic carbon-carbon double bond in its molecule; the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 15 nm or more from a maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim5]
5. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 1.5 × 103 cm-1 or more from a maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim6]
6. An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the conjugated molecule does not have both one hydrogen atom and one disubstituted amino group at the same time on one of carbon atoms constituting an aliphatic carbon-carbon double bond in its molecule; the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 1.5 × 103 cm-1 or more from a maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.

[claim7]
7. The organic optical material according to any one of claims 1 to 6, wherein the complex is a complex represented by the following formula (1a):
        W:X ...     (1a)
wherein W represents a conjugated molecule consisting of (A)l, (B)m and (C)n; each A is the same or different and represents an electron donating site; each B is the same or different and represents a conjugated site; each C is the same or different and represents an electron accepting site; : represents a non-covalent interaction; X represents a compound having a proton donating property or an electron pair accepting property; 1 and n each represent a number of 1 to 6; m represents a number of 0 to 6; and C and X are non-covalently bonded.

[claim8]
8. The organic optical material according to claim 7, wherein each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, a monosubstituted amino group, a disubstituted amino group, an alkoxycarbonyl group, a monovalent or divalent aromatic hydrocarbon group, a monovalent or divalent fused polycyclic aromatic hydrocarbon group, a monovalent or divalent saturated or unsaturated heterocyclic group, or a monovalent or divalent saturated or unsaturated fused polycyclic heterocyclic group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent atom or a divalent substituent.

[claim9]
9. The organic optical material according to claim 7, wherein each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a pyrrole group, a phenyl group, a phenylene group, a phenylphenylene group, an anthracene ring group, a phenanthrene ring group, a naphthacene ring group, a triphenylene ring group, a pyrene ring group, a chrysene ring group, a perylene ring group, an oxazole ring group, a thiazole ring group, a porphyrin ring group, a piperazine ring group, or an alkoxycarbonyl group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent substituent.

[claim10]
10. The organic optical material according to claim 7, wherein each A is the same or different and represents a hydroxy group, an optionally alkoxy group-substituted alkoxy group, an optionally alkyl group-substituted silyloxy group, an optionally hydroxy group-substituted phenyl group, a phenylphenylene group, or a substituent having an electron donating property in which at least one hydrogen atom of an aromatic hydrocarbon group is optionally replaced with a substituent.

[claim11]
11. The organic optical material according to claim 7, wherein each B is the same or different and represents a conjugated site having a chemical structure where multiple bonds are linked through a carbon-carbon single bond.

[claim12]
12. The organic optical material according to claim 7, wherein each B is the same or different and represents an alkenylene group, an alkynylene group, a phenylene group, a biphenylene group, a substituent in which at least one of these substituents is bonded to a phenylene group, or a substituent having an electron donating property in which at least one hydrogen atom of each of these groups is optionally replaced with a substituent.

[claim13]
13. The organic optical material according to claim 7, wherein each B is the same or different and represents an alkenylene group, or an optionally diphenylene-substituted vinylene group.

[claim14]
14. The organic optical material according to claim 7, wherein each C is the same or different and represents
(1) a halogen atom,
(2) a nitro group, a phenylamino group, carbene, N-heterocyclic carbene, silylene, N-heterocyclic silylene, nitrene, N-heterocyclic nitrene, a BF2 group, a cyano group, a pyridyl group, a pyridine N-oxy group, an acridine ring group, an acridine N-oxy group, a diazo group, a triazole group, a benzotriazole group, an oxazole group, a benzoxazole group, a thiazole group, a benzothiazole group, a diazole group, a benzodiazole group, an amino group, a monosubstituted amino group, a disubstituted amino group, a pyrazine ring group, a phenazine ring group, a pyrrolidone ring group, a pyridone ring group, an aromatic heterocyclic group, a fused polycyclic aromatic heterocyclic group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent, or
(3) a formyl group, a carbonyl group, a carbodiimide group, a pyrrolidone ring group, a pyridone ring group, a formyl group, a quinone ring group, a quinoline ring group, a naphthoquinone ring group, an anthraquinone ring group, a lactone ring group, an oxycarbonyl group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent.

[claim15]
15. The organic optical material according to claim 7, wherein each C is the same or different and represents a cyano group, a pyridyl group, an acridine ring group, or a lactone ring group.

[claim16]
16. The organic optical material according to claim 7, wherein X is a compound selected from the group consisting of a Bronsted acid, a Lewis acid and a halogen bonding donor.

[claim17]
17. The organic optical material according to claim 7, wherein X is p-toluenesulfonic acid, trifluoromethanesulfonic acid, methanesulfonic acid, triphenylborane, N,N-dialkylimidazolinium-2-halide, halogenoisoindolyl-1,3-dione, 2-halogenobenz[d]isothiazol-3(2H)-one 1,1-dioxide, 2-halogeno-5-nitroisoindolyl-1,3-dione, or 2-halogeno-3,4-dimethylthiazol-3-inium trifluorosulfonate.

[claim18]
18. The organic optical material according to claim 7, wherein X is a Bronsted acid.

[claim19]
19. The organic optical material according to claim 18, wherein the Bronsted acid is a substance capable of losing or donating a proton.

[claim20]
20. The organic optical material according to claim 7, wherein X is a Lewis acid.

[claim21]
21. The organic optical material according to claim 7, wherein X is a halogen bonding donor.

[claim22]
22. The organic optical material according to any one of claims 1 to 6, wherein the complex is a complex represented by the following formula (1b) :
        W:X ...     (1b)
wherein W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1, (C)n2-(B)m2-(A)l2-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1; A represents an electron donating site; B represents a conjugated site; C represents an electron accepting site; : represents a non-covalent interaction; X represents a compound having a proton donating property or an electron pair accepting property; 11 and n1 each represent 1; m1 represents a number of 0 to 2; 12 and n2 each represent 1; m2 represents a number of 0 to 2; m3 represents 1; and C and X are non-covalently bonded.

[claim23]
23. The organic optical material according to any one of claims 1 to 6, wherein the complex is a complex represented by the following formula (1b):
        W:X ...     (1b)
wherein
W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1, (C)n2-(B)m2-(A)12-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1;
each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, a monosubstituted amino group, a disubstituted amino group, an alkoxycarbonyl group, a monovalent or divalent aromatic hydrocarbon group, a monovalent or divalent fused polycyclic aromatic hydrocarbon group, a monovalent or divalent saturated or unsaturated heterocyclic group, or a monovalent or divalent saturated or unsaturated fused polycyclic heterocyclic group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent atom or a divalent substituent;
each B is the same or different and represents a conjugated site having a chemical structure where multiple bonds are linked through a carbon-carbon single bond;
each C is the same or different and represents
(1) a halogen atom,
(2) a nitro group, a phenylamino group, carbene, N-heterocyclic carbene, silylene, N-heterocyclic silylene, nitrene, N-heterocyclic nitrene, a BF2 group, a cyano group, a pyridyl group, a pyridine N-oxy group, an acridine ring group, an acridine N-oxy group, a diazo group, a triazole group, a benzotriazole group, an oxazole group, a benzoxazole group, a thiazole group, a benzothiazole group, a diazole group, a benzodiazole group, a primary amino group, a secondary amino group, a tertiary amino group, a pyrazine ring group, a phenazine ring group, a pyrrolidone ring group, a pyridone ring group, an aromatic heterocyclic group, a fused polycyclic aromatic heterocyclic group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent, or (3) a formyl group, a carbonyl group, a carbodiimide group, a pyrrolidone ring group, a pyridone ring group, a formyl group, a quinone ring group, a quinoline ring group, a naphthoquinone ring group, an anthraquinone ring group, a lactone ring group, an oxycarbonyl group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent;
X represents a compound selected from the group consisting of a Bronsted acid, a Lewis acid and a halogen bonding donor (provided that when X is trifluoroborane or tris(pentafluorophenyl)borane, W is not a conjugated molecule wherein A is a phenyl group having a methoxy group at position 4 or a phenyl group having a dimethylamino group at position 4, B is -CH=CH- or -C≡C-, m is 0 or 1, and C is a pyridine group);
11 and n1 each represent 1; m1 represents a number of 0 to 3; 12 and n2 each represent 1; m2 represents a number of 0 to 3; m3 represents 1; and C and X are non-covalently bonded.

[claim24]
24. The organic optical material according to any one of claims 1 to 6, wherein the complex is a complex represented by the following formula (1b):
        W:X ...     (1b)
wherein
W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1, (C)n2-(B)m2-(A)l2-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1;
each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a pyrrole group, a phenyl group, a phenylene group, a phenylphenylene group, an anthracene ring group, a phenanthrene ring group, a naphthacene ring group, a triphenylene ring group, a pyrene ring group, a chrysene ring group, a perylene ring group, a diethylamino group, an oxazole ring group, a thiazole ring group, a porphyrin ring group, a piperazine ring group, or an alkoxycarbonyl group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent substituent;
each B is the same or different and represents a conjugated site having a chemical structure where multiple bonds are linked through a carbon-carbon single bond;
each C is the same or different and represents
(1) a halogen atom,
(2) a nitro group, a phenylamino group, carbene, N-heterocyclic carbene, silylene, N-heterocyclic silylene, nitrene, N-heterocyclic nitrene, a BF2 group, a cyano group, a pyridyl group, a pyridine N-oxy group, an acridine ring group, an acridine N-oxy group, a diazo group, a triazole group, a benzotriazole group, an oxazole group, a benzoxazole group, a thiazole group, a benzothiazole group, a diazole group, a benzodiazole group, an amino group, a monosubstituted amino group, a disubstituted amino group, a pyrazine ring group, a phenazine ring group, a pyrrolidone ring group, a pyridone ring group, an aromatic heterocyclic group, a fused polycyclic aromatic heterocyclic group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent, or
(3) a formyl group, a carbonyl group, a carbodiimide group, a pyrrolidone ring group, a pyridone ring group, a formyl group, a quinone ring group, a quinoline ring group, a naphthoquinone ring group, an anthraquinone ring group, a lactone ring group, an oxycarbonyl group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent;
X represents a compound selected from the group consisting of a Bronsted acid, a Lewis acid and a halogen bonding donor (provided that when X is trifluoroborane or tris(pentafluorophenyl)borane, W is not a conjugated molecule wherein A is a phenyl group having a methoxy group at position 4 or a phenyl group having a dimethylamino group at position 4, B is -CH=CH- or -C≡C-, m is 0 or 1, and C is a pyridine group);
11 and n1 each represent 1; m1 represents 0; l2 and n2 each represent 1; m2 and m3 each represent 0; and C and X are non-covalently bonded.

[claim25]
25. The organic optical material according to claim 7, wherein the organic optical material is a complex wherein
W represents a conjugated molecule wherein
each A is the same or different and is a hydroxy group, an optionally alkoxy group-substituted alkoxy group, an optionally alkyl group-substituted silyloxy group, an optionally hydroxy group-substituted phenyl group, a phenylphenylene group, or a substituent having an electron donating property in which at least one hydrogen atom of an aromatic hydrocarbon group is optionally replaced with a substituent;
each B is the same or different and is an alkenylene group, or an optionally diphenylene-substituted vinylene group;
each C is the same or different and is a cyano group, a pyridyl group, an acridine ring group, or a lactone ring group;
1 is 1, 2 or 3; n is 1 or 2; and m is 0 or 1; X represents p-toluenesulfonic acid, trifluoromethanesulfonic acid, methanesulfonic acid, triphenylborane, N,N-dialkylimidazolinium-2-halide, 2-halogenoisoindolyl-1,3-dione, 2-halogenobenz[d]isothiazol-3(2H)-one 1,1-dioxide, 2-halogeno-5-nitroisoindolyl-1,3-dione, or 2-halogeno-3,4-dimethylthiazol-3-inium trifluorosulfonate; and
C and X are non-covalently bonded.

[claim26]
26. Use of an organic optical material according to any one of claims 1 to 25 as an optical material which is contained in an optical composition selected from the composition group consisting of a fluorescence emitting composition, a fluorescent coating composition, a wavelength conversion member composition, an organic EL member composition, an organic laser member composition, an organic transistor member composition, an organic solar cell member composition, and a chemical sensor member composition.

[claim27]
27. A mixture comprising two or more organic optical materials according to any one of claims 1 to 25 mixed with each other, or an organic optical material according to any one of claims 1 to 25 mixed with an additional organic optical material.

[claim28]
28. A method for adjusting the color of emitted light, comprising using one or two or more organic optical materials according to any one of claims 1 to 25, or a mixture of the one or two or more organic optical materials with an additional organic optical material.

[claim29]
29. A pi-conjugated compound complex comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein the conjugated molecule does not have both one hydrogen atom and one disubstituted amino group at the same time on one of carbon atoms constituting an aliphatic carbon-carbon double bond in its molecule.

[claim30]
30. The complex according to claim 29, wherein the complex is a complex represented by the following formula (1a):
        W:X ...     (1a)
wherein W represents a conjugated molecule consisting of (A)l, (B)m and (C)n; each A is the same or different and represents an electron donating site; each B is the same or different and represents a conjugated site; each C is the same or different and represents an electron accepting site; : represents a non-covalent interaction; X represents a compound having a proton donating property or an electron pair accepting property; 1 and n each represent a number of 1 to 6; m represents a number of 0 to 6; and C and X are non-covalently bonded.

[claim31]
31. The complex according to claim 30, wherein the complex is a complex represented by the following formula (1b):
        W:X ...     (1b)
wherein W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1, (C)n2-(B)m2-(A)l2-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1; A represents an electron donating site; B represents a conjugated site; C represents an electron accepting site; : represents a non-covalent interaction; X represents a compound having a proton donating property or an electron pair accepting property; l1 and n1 each represent 1; m1 represents a number of 0 to 2; l2 and n2 each represent 1; m2 represents a number of 0 to 2; m3 represents 1; and C and X are non-covalently bonded.

[claim32]
32. The complex according to claim 30, wherein the complex is a complex represented by the following formula (1b):
        W:X ...     (1b)
wherein
W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1, (C)n2-(B)m2-(A)l2-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1;
each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, a monosubstituted amino group, a disubstituted amino group, an alkoxycarbonyl group, a monovalent or divalent aromatic hydrocarbon group, a monovalent or divalent fused polycyclic aromatic hydrocarbon group, a monovalent or divalent saturated or unsaturated heterocyclic group, or a monovalent or divalent saturated or unsaturated fused polycyclic heterocyclic group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent atom or a divalent substituent;
each B is the same or different and represents a conjugated site having a chemical structure where multiple bonds are linked through a carbon-carbon single bond;
each C is the same or different and represents
(1) a halogen atom,
(2) a nitro group, a phenylamino group, carbene, N-heterocyclic carbene, silylene, N-heterocyclic silylene, nitrene, N-heterocyclic nitrene, a BF2 group, a cyano group, a pyridyl group, a pyridine N-oxy group, an acridine ring group, an acridine N-oxy group, a diazo group, a triazole group, a benzotriazole group, an oxazole group, a benzoxazole group, a thiazole group, a benzothiazole group, a diazole group, a benzodiazole group, a primary amino group, a secondary amino group, a tertiary amino group, a pyrazine ring group, a phenazine ring group, a pyrrolidone ring group, a pyridone ring group, an aromatic heterocyclic group, a fused polycyclic aromatic heterocyclic group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent, or
(3) a formyl group, a carbonyl group, a carbodiimide group, a pyrrolidone ring group, a pyridone ring group, a formyl group, a quinone ring group, a quinoline ring group, a naphthoquinone ring group, an anthraquinone ring group, a lactone ring group, an oxycarbonyl group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent;
X represents a compound selected from the group consisting of a Bronsted acid, a Lewis acid and a halogen bonding donor (provided that when X is trifluoroborane or tris(pentafluorophenyl)borane, W is not a conjugated molecule wherein A is a phenyl group having a methoxy group at position 4 or a phenyl group having a dimethylamino group at position 4, B is -CH=CH- or -C≡C-, m is 0 or 1, and C is a pyridine group);
11 and n1 each represent 1; m1 represents a number of 0 to 3; l2 and n2 each represent 1; m2 represents a number of 0 to 3; m3 represents 1; and C and X are non-covalently bonded.

[claim33]
33. The complex according to claim 30, wherein the complex is a complex represented by the following formula (1b):
        W:X ...     (1b)

wherein W represents a conjugated molecule consisting of (A)l1-(B)m1-(C)n1 or (C)n2-(B)m2-(A)l2-(B)m3-(A)l1-(B)m1-(C)n1 or (A)n2-(B)m2-(C)l2-(B)m3-(C)l1-(B)m1-(A)n1;
each A is the same or different and represents a hydroxy group, an alkoxy group, an alkyl group, an alkenyl group, a silyloxy group, a silyl group, an amino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a pyrrole group, a phenyl group, a phenylene group, a phenylphenylene group, an anthracene ring group, a phenanthrene ring group, a naphthacene ring group, a triphenylene ring group, a pyrene ring group, a chrysene ring group, a perylene ring group, a diethylamino group, an oxazole ring group, a thiazole ring group, a porphyrin ring group, a piperazine ring group, or an alkoxycarbonyl group, wherein at least one hydrogen atom of each of these groups is optionally replaced with a substituent, and when a plurality of the same or different groups are present as to each of these groups, the groups are optionally linked through a divalent substituent;
each B is the same or different and represents a conjugated site having a chemical structure where multiple bonds are linked through a carbon-carbon single bond;
each C is the same or different and represents
(1) a halogen atom,
(2) a nitro group, a phenylamino group, carbene, N-heterocyclic carbene, silylene, N-heterocyclic silylene, nitrene, N-heterocyclic nitrene, a BF2 group, a cyano group, a pyridyl group, a pyridine N-oxy group, an acridine ring group, an acridine N-oxy group, a diazo group, a triazole group, a benzotriazole group, an oxazole group, a benzoxazole group, a thiazole group, a benzothiazole group, a diazole group, a benzodiazole group, an amino group, a monosubstituted amino group, a disubstituted amino group, a tertiary amino group, a pyrazine ring group, a phenazine ring group, a pyrrolidone ring group, a pyridone ring group, an aromatic heterocyclic group, a fused polycyclic aromatic heterocyclic group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these groups is replaced with a substituent, or
(3) a formyl group, a carbonyl group, a carbodiimide group, a pyrrolidone ring group, a pyridone ring group, a formyl group, a quinone ring group, a quinoline ring group, a naphthoquinone ring group, an anthraquinone ring group, a lactone ring group, an oxycarbonyl group, or a substituent having an electron accepting property even though at least one hydrogen atom bonded to a carbon atom on each of these gro(...)
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • KUNINOBU YOICHIRO
  • KANAI MOTOMU
  • YAMAKAWA TAKESHI
  • YOSHIGOE YUSUKE
  • WANG ZIJIA
  • NAGASHIMA HIDEO
  • TAHARA ATSUSHI
国際特許分類(IPC)
指定国 Contracting States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Extension States: BA ME
参考情報 (研究プロジェクト等) CREST Creation of Innovative Functions of Intelligent Materials on the Basis of the Element Strategy AREA
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