WO2014021023A1 - 潜在性添加剤及び該添加剤を含有する組成物 - Google Patents
潜在性添加剤及び該添加剤を含有する組成物 Download PDFInfo
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- WO2014021023A1 WO2014021023A1 PCT/JP2013/067091 JP2013067091W WO2014021023A1 WO 2014021023 A1 WO2014021023 A1 WO 2014021023A1 JP 2013067091 W JP2013067091 W JP 2013067091W WO 2014021023 A1 WO2014021023 A1 WO 2014021023A1
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- 0 *C1(c2ccccc2-c2ccccc12)N Chemical compound *C1(c2ccccc2-c2ccccc12)N 0.000 description 3
- GTGICFJJERNWGF-UHFFFAOYSA-N CC(C)(C)c1cc(CN(C(N(Cc(cc2C(C)(C)C)cc(C(C)(C)C)c2OC(OC(C)(C)C)=O)C(N2Cc(cc3C(C)(C)C)cc(C(C)(C)C)c3OC(OC(C)(C)C)=O)=O)=O)C2=O)cc(C(C)(C)C)c1OC(OC(C)(C)C)=O Chemical compound CC(C)(C)c1cc(CN(C(N(Cc(cc2C(C)(C)C)cc(C(C)(C)C)c2OC(OC(C)(C)C)=O)C(N2Cc(cc3C(C)(C)C)cc(C(C)(C)C)c3OC(OC(C)(C)C)=O)=O)=O)C2=O)cc(C(C)(C)C)c1OC(OC(C)(C)C)=O GTGICFJJERNWGF-UHFFFAOYSA-N 0.000 description 1
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to a latent additive that is inactive at room temperature and is activated by heating to a predetermined temperature to exhibit a function, and a composition containing the latent additive. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the composition, and a color filter that uses the colored photosensitive composition.
- Patent Documents 1 to 4 In order to improve the weather resistance and heat resistance of a resin composition, a method of stabilizing by adding an ultraviolet absorber or an antioxidant is known (Patent Documents 1 to 4).
- Patent Document 5 phenolic antioxidants, in particular, have the effect of trapping radicals that greatly affect the deterioration of the polymer, so adding antioxidants into the polymerization system generally acts as a so-called polymerization inhibitor, inhibiting curing.
- JP-A-6-179798 JP 7-109380 A Japanese Patent Laid-Open No. 11-071355 JP 2002-097224 A US5279896A
- an object of the present invention is to provide a latent additive that is inactive at room temperature and is activated by heating to a predetermined temperature to exhibit its function. Another object of the present invention is to provide a composition using the latent additive. Another object of the present invention is to provide a colored photosensitive composition obtained by adding a colorant to the above composition, particularly a colored photosensitive composition suitable for a color filter.
- a compound having a specific protecting group functions effectively as a latent additive, and that a composition using the compound does not cause curing inhibition and has excellent heat resistance.
- a colored photosensitive composition obtained by adding a colorant to the above composition is suitable for a color filter for an image display device such as a liquid crystal display panel without reducing the luminance of an optical filter (particularly a color filter).
- the present invention has been made based on the above findings, and provides a latent additive represented by the following general formula (1).
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an optionally substituted alkyl group having 1 to 40 carbon atoms, or a carbon atom number
- R 4 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to Represents 20 heterocycle-containing groups or trialkylsilyl groups,
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 2 may be bonded to each other to form a benzene ring or a naphthalene ring
- the plurality of R 2 and R 4 may be the same or different
- n represents an integer of 1 to 10
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- X represents a direct bond, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following [Chemical Formula 2],>P ⁇ O,>C ⁇ O,> NR 10 ,> PR 10 , —OR 10 , -SR 10 , -NR 10 R 11, -PR 10 R 11, or an aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent having the same valence as n, An aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms
- this invention provides the composition containing the latent additive represented by the said General formula (1).
- the present invention also provides a colored photosensitive composition obtained by adding a colorant to the above composition, and a color filter using the colored photosensitive composition.
- the present invention also provides novel compounds represented by the following general formulas (2), (6) and (8).
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 201 and R 202 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 204 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to Represents 20 heterocycle-containing groups or trialky
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 202 may be bonded to each other to form a benzene ring or a naphthalene ring
- the plurality of R 202 and R 204 may be the same or different
- X 2 represents an oxygen atom, a sulfur atom, a group represented by the following [Chemical Formula 4],> C ⁇ O, —NH—CO—, —CO—NH—,> NR 12 ,> PR 12 or the following general formula ( 3), (4) or any one of the substituents represented by the group of the following [Chemical Formula 10], wherein R 12 is a hydrogen atom, an aliphatic having 1 to 35 carbon atoms which may have a substituent.
- the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocycle-containing group are a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O.
- O, -S-S-, or -SO 2 - may be replaced by a combination of group selected from the aromatic ring Alternatively, the heterocyclic ring may be condensed with another ring. X 2 may form a ring together with A. )
- Y 1 and Y 5 each independently represent a direct bond and an alkylene group having 1 to 4 carbon atoms
- Y 2 and Y 4 each independently represent an oxygen atom or — NR 13- represents
- R 13 represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms
- Y 3 represents a direct bond
- -NR 16- a divalent carbon atom having 1 to 35 carbon atoms.
- the aromatic ring-containing hydrocarbon group may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- R 14 and R 15 are each independently hydrogen Atoms, alkyl groups having 1 to 8 carbon atoms, aryl groups having 6 to 20 carbon atoms, or 7 carbon atoms
- Arylalkyl group of 20, R 16 the number of hydrogen atoms, aliphatic hydrocarbon group which may carbon atoms 1 to 35 which may have a substituent, which may have a substituent group having a carbon atom 6
- Y 6 and Y 8 are each independently, -NR 17 - or be interrupted by oxygen atoms represent also alkylene group having a carbon number of 1 ⁇ 4, Y 7 are, a direct bond, -O -, - S -, - SO 2 -, - CR 18 R 19 - or below in [formula 7] ⁇ represents any of substituents represented by Chemical formula 9], R 17 is hydrogen Represents an atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 18 and R 19 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.
- R 100 and R 101 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydrogen group, a nitro group, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.
- E represents a number from 1 to 4
- f represents a number from 1 to 4.
- R 21 represents a hydrogen atom, an optionally substituted phenyl group, or a cycloalkyl group having 3 to 10 carbon atoms
- R 22 represents an alkyl group having 1 to 10 carbon atoms
- R 102 and R 103 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.
- i represents a number from 1 to 4
- j represents a number from 1 to 4.
- R 23 and R 24 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent.
- R 31 represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, or an aromatic group having 6 to 35 carbon atoms which may have a substituent.
- Y 9 and Y 10 each independently represents an alkylene group having 1 to 4 carbon atoms.
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 301 and R 302 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 304 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to 2 carbon atoms.
- R 301 , R 302 and R 304 represents 20 heterocycle-containing groups or trialkylsilyl groups
- the methylene group in the alkyl group or arylalkyl group represented by R 301 , R 302 and R 304 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, — CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —O—CO—S—, —S—CO—O—, — CO—NH—, —NH—CO—, —NH—CO—O—, —NR ′ —,> P ⁇ O, —SS—, —SO 2 — or a combination of groups selected from nitrogen atoms
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 302 may be bonded to each other to form a
- Y 11 represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms.
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—,> CO, — CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,> NR 32 ,> PR 32 or an aliphatic group having 1 to 35 carbon atoms which may have a substituent
- R 32 is a hydrogen atom, an aliphatic
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 401 and R 402 each independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 404 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to Represents 20 heterocycle-containing groups or trialky
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 402 may be bonded to each other to form a benzene ring or a naphthalene ring
- the plurality of R 402 and R 404 may be the same or different
- n represents a number from 4 to 6
- represents a substituent represented by the following general formula (10) when n 5
- represents a substituent represented by the following general formula (10) when n 6.
- the substituent represented by General formula (11) is represented.
- X 4 may form a ring together with A, and the aromatic ring or heterocyclic ring may be condensed with another ring. )
- Y 12 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a carbon atom.
- Y 13 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms, or a C 2 to 30 carbon atom group. Represents a heterocyclic ring-containing group, and the aliphatic hydrocarbon group may be replaced by a combination of groups selected from —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
- Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (7).
- Y 14 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 to 35 carbon atoms. Represents a heterocyclic ring-containing group, and the aliphatic hydrocarbon group may be replaced by a combination of groups selected from —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
- Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (7).
- the present invention it is possible to provide a latent additive which is inactive at room temperature and becomes active when heated to a predetermined temperature.
- the composition containing the latent additive is excellent in heat resistance without causing curing inhibition.
- the latent additive represented by the general formula (1) will be described.
- the latent additive is inactive in a pre-baking step at room temperature or 150 ° C., and the protective group is formed by heating at 100 to 250 ° C. or heating at 80 to 200 ° C. in the presence of an acid / base catalyst.
- latent resin additives such as latent antioxidants and latent UV absorbers; latent developer for thermal paper; latent storage stability for thermal paper Agents; latent curing agents and the like.
- the latent additive represented by the general formula (1) has a structure in which n specific groups are bonded to an n-valent specific atom or group represented by X.
- the n groups may be the same as or different from each other.
- the value of n is 1 to 10, and preferably 2 to 6 from the viewpoint of ease of synthesis.
- Examples of the five-membered aromatic ring represented by A in the general formula (1) include cyclopentadiene and ferrocene.
- Examples of the five-membered heterocyclic ring include furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, and pyrazole.
- Imidazole imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazole, isothiazolidine and the like
- the six-membered aromatic ring includes benzene, naphthalene, anthracene, fluorene, perylene, pyrene and the like
- Examples of the six-membered heterocyclic ring include piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine, and triazine. These rings are condensed or substituted with other rings.
- halogen atom represented by R 1 and R 2 include fluorine, chlorine, bromine and iodine.
- Examples of the alkyl group having 1 to 40 carbon atoms represented by R 1 , R 2 and R 4 include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso -Octyl, tert-octyl, adamantyl and the like,
- Examples of the alkoxy group having 1 to 8 carbon atoms represented by R 1 and R 2 include methyloxy, ethyloxy, iso-propyloxy, butyloxy,
- Examples of the aryl group having 6 to 20 carbon atoms represented by R 4 include phenyl, naphthyl, anthracenyl and the like, Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 4 include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl group, etc.
- heterocyclic group having 2 to 20 carbon atoms represented by R 4 examples include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, Benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-di And oxyimidazolidin-3-yl, 2,4-dioxyoxazolidin-3-yl, and the like.
- Examples of the trialkylsilyl group represented by R 4 include trimethylsilane, triethylsilane, and ethyldimethylsilane.
- R 4 those in which —CO—O— is bonded to the terminal on the oxygen atom side of the alkyl group having 1 to 8 carbon atoms are preferable because they effectively exhibit the function as a latent additive.
- Examples of the monovalent aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by X, R 10 and R 11 in the general formula (1) include, for example, methyl, ethyl Propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, Alkyl groups such as heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl
- Examples of the monovalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent include arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl; phenyl, naphthyl Aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio;
- Examples of the monovalent heterocyclic-containing group having 2 to 35 carbon atoms which may have a substituent include pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl , Furyl, furanyl, benzofuranyl, thienyl,
- substituents examples include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl and phenylcarbonyl ( Benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl, etc .; acetyloxy, benzoyloxy, etc.
- ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl
- halogen atoms
- Examples of the group represented by X in the general formula (1) include a group represented by the following general formula (12) when n is 2, and a group represented by the following general formula (7) when n is 3.
- n 4
- the group represented by the following general formula (9) is exemplified.
- n 5
- the group represented by the following general formula (10) is exemplified.
- n 6
- a group represented by the following general formula (11) is exemplified.
- X 1 represents —CR 32 R 33 —, —NR 34 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and an aromatic ring having 6 to 35 carbon atoms.
- the aromatic ring-containing hydrocarbon group having 6 to 35 or the heterocyclic group having 2 to 35 carbon atoms is represented by —O—, —S—, —CO—, —COO—, —OCO— or —NH—, or A linking group of these combinations may be substituted, and R 32 and R 33 may be a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a 7 to 20 carbon atom.
- Z 1 and Z 2 are independently a direct bond, -O -, - -,> CO, -CO-O -, - O-CO -, - SO 2 -, - SS -, - SO -,> NR 35 or> represents PR 35, R 34 and R 35, a hydrogen atom, An aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent, or a substituent Represents an optionally substituted heterocyclic group having 2 to 35 carbon atoms.)
- R 21 represents a hydrogen atom, an optionally substituted phenyl group, or a cycloalkyl group having 3 to 10 carbon atoms
- R 22 represents an alkyl group having 1 to 10 carbon atoms
- R 23 and R 24 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent.
- b represents a number from 0 to 4
- c Represents a number of 0 to 8
- g represents a number of 0 to 4
- h is a number of 0-4, the sum of the number of g and h is 2-4.
- Y 11 represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms.
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—,> CO, — CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,> NR 32 ,> PR 32 or an aliphatic group having 1 to 35 carbon atoms which may have a substituent
- R 32 is a hydrogen atom, an aliphatic
- Y 12 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a carbon atom.
- Represents a heterocyclic ring-containing group having 2 to 35, the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic ring-containing group having 2 to 35 carbon atoms is represented by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH— may be substituted
- Z 1 to Z 4 are each independently Z 1 to Z 3 in formula (7). It is a group in the same range as the group represented.
- Y 13 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms, or a C 2 to 30 carbon atom group.
- Represents a heterocyclic ring-containing group, the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic ring-containing group having 2 to 35 carbon atoms is represented by —COO—, —O—, — OCO—, —NHCO—, —NH— or —CONH— may be substituted
- Z 1 to Z 5 are each independently a group represented by Z 1 to Z 3 in formula (7). It is a group within the same range.
- Y 14 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 to 35 carbon atoms.
- Represents a heterocyclic ring-containing group, the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic ring-containing group having 2 to 35 carbon atoms is represented by —COO—, —O—, — OCO—, —NHCO—, —NH— or —CONH— may be substituted
- Z 1 to Z 6 are each independently a group represented by Z 1 to Z 3 in the general formula (7). It is a group within the same range.
- Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 1 in the general formula (12) include methane, ethane, propane, iso-propane, butane, sec-butane, and tert-butane.
- divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms examples include divalent groups in which groups such as phenylene, naphthylene, and biphenyl are substituted with Z 1 and Z 2 .
- divalent heterocyclic group having 2 to 35 carbon atoms examples include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene, thiolane, and the like. And divalent groups substituted with 1 and Z 2 . These groups may be further substituted with a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 8 carbon atoms.
- Examples of the alkyl group having 1 to 8 carbon atoms represented by R 32 and R 33 in X 1 in the general formula (12) include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t -Butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, t-heptyl, 1-octyl, Isooctyl, t-octyl and the like,
- Examples of the aryl group having 6 to 20 carbon atoms include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylpheny
- Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 21 in the group represented by [Chemical Formula 19] include cyclopropyl, cyclobutyl, cyclopentyl, cyclohebutyl, cyclooctyl and the like, and these groups are carbon. And a group substituted with an alkyl group having 1 to 10 atoms or an alkoxy group having 1 to 10 carbon atoms, and the like.
- Examples of the alkyl group having 1 to 10 carbon atoms, the alkoxy group having 1 to 10 carbon atoms and the halogen atom represented by R 22 include alkyl groups, alkoxy groups and halogen atoms exemplified in the description of the general formula (1).
- alkenyl group having 2 to 10 carbon atoms examples include vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl and the like.
- the alkyl group, alkoxy group and alkenyl group in R 22 may be substituted with a halogen atom, and the substitution position is not limited.
- the alkyl group having 1 to 10 carbon atoms, the aryl group having 6 to 20 carbon atoms, and the arylalkyl group having 7 to 20 carbon atoms in the group represented by [Chemical Formula 21] are represented by the general formula (1 And alkyl groups, aryl groups and arylalkyl groups exemplified in the description of) and groups in which these groups are substituted with halogen atoms.
- aryloxy group having 6 to 20 carbon atoms examples include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyl Oxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4-octylphenyloxy, 4- (2-ethylhexyl) Phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6-dimethylphenyloxy, 3.4-dimethylphenyloxy, 3.5-dimethylphenyloxy , 2,4-ji tert-bu Ruphenyloxy, 2,5-di-tert-butylphen
- heterocycle-containing group having 2 to 20 carbon atoms examples include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene, thiofuran, and the like. Is a group substituted with a halogen atom.
- Examples of the trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11 in the general formula (7) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (12). Include trivalent groups substituted with Z 1 , Z 2 and Z 3 , and these groups include —O—, —S—, —CO—, —CO—O—, —O—CO—. , —SO 2 —, —NH— or a combination thereof, Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms include the aromatic ring-containing hydrocarbon groups exemplified in the description of X 1 in the general formula (12) as Z 1 , Z 2 and Z 3 .
- trivalent heterocyclic group having 2 to 35 carbon atoms examples include those in which the heterocyclic group exemplified in the description of X 1 in the general formula (12) is substituted with Z 1 , Z 2 and Z 3. Valent groups.
- Examples of the tetravalent C1-35 aliphatic hydrocarbon group represented by Y 12 in the general formula (9) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (12). Include tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 , such as —O—, —S—, —CO—, —COO—, —OCO—, —NH— or these May be interrupted by a combination of Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms include the aromatic ring-containing hydrocarbon groups exemplified in the description of X 1 in the general formula (2), Z 1 , Z 2 , Z 3 and A tetravalent group substituted with Z 4 , The tetravalent heterocyclic containing group having a carbon number of 2 to 35, a heterocyclic ring-containing groups exemplified in the description of X 1 in the general formula (2), substituted with
- Examples of the aliphatic hydrocarbon group having 2 to 35 pentavalent carbon atoms represented by Y 13 in the general formula (10) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (2).
- pentavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 and include —O—, —S—, —CO—, —CO—O—, —O—CO.
- Examples of the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms include the aromatic ring-containing hydrocarbon groups exemplified in the description of X 1 in the general formula (12), Z 1 , Z 2 , Z 3 , And pentavalent groups substituted with Z 4 and Z 5 ,
- the heterocyclic group exemplified in the description of X 1 in the general formula (12) is Z 1 , Z 2 , Z 3 , Z 4 and Z And pentavalent group substituted with 5 .
- Examples of the aliphatic hydrocarbon group having 2 to 35 hexavalent carbon atoms represented by Y 14 in the general formula (11) include the aliphatic hydrocarbon groups exemplified in the description of X 1 in the general formula (12). Include hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , and include —O—, —S—, —CO—, —COO—, —OCO—.
- Examples of the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms include the aromatic ring-containing hydrocarbon groups exemplified in the description of X 1 in the general formula (12), Z 1 , Z 2 , Z 3 , And hexavalent groups substituted with Z 4 , Z 5 and Z 6 , As the hexavalent heterocyclic group having 2 to 35 carbon atoms, the heterocyclic group exemplified in the description of X 1 in the general formula (12) is Z 1 , Z 2 , Z 3 , Z 4 , Z And hexavalent groups substituted with 5 and Z 6 .
- Y 1 and Y 5 each independently represent an alkylene group having 1 to 4 carbon atoms
- Y 2 and Y 4 each independently represent an oxygen atom or —NR 13 —.
- R 13 represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms
- Y 3 represents —CR 14 R 15 —, —NR 16 —, a divalent carbon atom of 1 to 35
- the aromatic ring-containing hydrocarbon group or the heterocycle-containing group having 2 to 35 carbon atoms may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
- R 14 and R 15 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, carbon atoms An aryl group or an arylalkyl group having 7 to 20 carbon atoms in ⁇ 20, R 16 is a hydrogen atom, an aliphatic hydrocarbon group which may carbon atoms 1 to 35 which may have a substituent, Represents an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a heterocyclic group containing 2 to 35 carbon atoms which may have a substituent.
- Y 6 and Y 8 are each independently, -NR 17 - or an alkylene group which may having 1 to 4 carbon atoms optionally replaced by an oxygen atom
- Y 7 is directly A bond, —O—, —S—, —SO 2 —, —CR 18 R 19 — or any one of the above-described substituents represented by [Chemical Formula 19] to [Chemical Formula 21], wherein R 17 represents a hydrogen atom; Or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 18 and R 19 each independently represents an alkyl group having 1 to 8 carbon atoms which may be substituted with a hydrogen atom or a halogen atom. .
- R 31 represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, or an aromatic group having 6 to 35 carbon atoms which may have a substituent. This represents a heterocyclic group containing 2 to 35 carbon atoms which may have a ring-containing hydrocarbon group or a substituent.
- Y 9 and Y 10 each independently represents an alkylene group having 1 to 4 carbon atoms.
- R 32 is the same group as R 32 in the general formula (7), and when there are two or more groups in the group, they may be the same or different, and Z 11 represents Z 1 to Z Represents a group in the same range as the group represented by 3. )
- R 32 is the same group as R 32 in the general formula (7), if in the base are two or more, or different, even the same, Z 11 is Z 1 ⁇ Represents a group in the same range as the group represented by Z 3. )
- R 32 is the same group as R 32 in the general formula (7), and when there are two or more groups in the group, they may be the same or different, and Z 10 , Z 11 , Z 12 , Z 13 and Z 14 represent groups in the same range as the groups represented by Z 1 to Z 3. )
- R 32 is the same group as R 32 in the general formula (7), and when there are two or more groups in the group, they may be the same or different, and Z 10 , Z 11 , Z 12 , Z 13 , Z 14 and Z 15 represent groups in the same range as the groups represented by Z 1 to Z 3. )
- Specific examples of the compound represented by the general formula (1) include compounds represented by the following [Chemical Formula 35] to [Chemical Formula 56], but the present invention is not limited to these compounds.
- the method for producing the compound represented by the general formula (1) is not particularly limited.
- JP-A-57-111375, JP-A-3-173743, JP-A-6-128195, JP-A-7-206791, and JP-A-7-7 -252191, JP-T 2004-501128 phenolic compounds produced by the methods described in each publication, acid anhydrides, acid chlorides, Boc reagents, alkyl halide compounds, silyl chloride compounds, allyl ether compounds, etc. It can be obtained by reaction.
- the latent additive of the present invention is used as a latent antioxidant or latent ultraviolet absorber in a photocurable composition, a thermosetting composition, a photosensitive composition, or a polymerizable composition, and also has a latent manifestation. It is also used for heat sensitive materials as colorants.
- the content of the latent additive of the present invention is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
- the content of the latent additive of the present invention is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
- the content of the latent additive of the present invention is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
- the content of the latent additive of the present invention is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
- the photocurable composition is cured by light irradiation, and may be any of a photocationic curable composition, a photoanion curable composition, or a photoradical curable composition. , Radicals generated by photo-radical polymerization initiators during light irradiation without causing the latent additive to trap, and after the heating and activation of the latent antioxidant, radicals generated by oxidation, etc. Is preferable.
- the photo-radical curable composition contains the latent additive of the present invention as a latent antioxidant, and contains a radical polymerizable organic substance and a photo radical polymerization initiator as essential components.
- the radical polymerizable organic substance is a compound that is polymerized or cross-linked by light irradiation in the presence of a radical photopolymerization initiator, preferably a compound having at least one unsaturated double bond in one molecule.
- a radical photopolymerization initiator preferably a compound having at least one unsaturated double bond in one molecule. Examples thereof include acrylate compounds, methacrylate compounds, allyl urethane compounds, unsaturated polyester compounds, styrene compounds, radical polymerizable group-modified silicone oils, vinyl compounds, and the like.
- compounds having a (meth) acryl group are preferred because they are easy to synthesize and obtain, and are easy to handle.
- examples thereof include epoxy (meth) acrylate, urethane (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, and (meth) acrylic acid esters of alcohols.
- the epoxy (meth) acrylate is, for example, an acrylate obtained by reacting a conventionally known aromatic epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin or the like with (meth) acrylic acid.
- a particularly preferred one is a (meth) acrylate of an aromatic epoxy resin, and a polyglycidyl ether of a polyhydric phenol having at least one aromatic nucleus or an alkylene oxide adduct thereof, It is (meth) acrylate obtained by making it react with (meth) acrylic acid.
- (meth) acrylate, epoxy novolak resin and (meth) acryl obtained by reacting glycidyl ether obtained by reaction of bisphenol A or its alkylene oxide adduct with epichlorohydrin with (meth) acrylic acid.
- examples include (meth) acrylates obtained by reacting acids.
- the urethane (meth) acrylate is a (meth) acrylate obtained by reacting a hydroxyl group-containing (meth) acrylic acid ester and an isocyanate group with one or two or more hydroxyl group-containing polyesters or hydroxyl group-containing polyethers, or a hydroxyl group. And (meth) acrylates obtained by reacting the containing (meth) acrylic acid ester with isocyanates.
- the hydroxyl group-containing polyester used here is a hydroxyl group-containing polyester obtained by reaction of one or more aliphatic polyhydric alcohols with one or more polybasic acids
- the aliphatic polyhydric alcohol include 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, triethylene glycol, neopentyl glycol, polyethylene glycol, polypropylene glycol, trimethylolpropane, and glycerin.
- the polybasic acid include adipic acid, terephthalic acid, phthalic anhydride, trimellitic acid, and the like.
- hydroxyl group-containing polyether is a hydroxyl group-containing polyether obtained by adding one or more alkylene oxides to an aliphatic polyhydric alcohol, and the aliphatic polyhydric alcohol includes the compounds described above. The same thing can be illustrated.
- alkylene oxide include ethylene oxide and propylene oxide.
- a hydroxyl group-containing (meth) acrylic acid ester is a hydroxyl group-containing (meth) acrylic acid ester obtained by esterification reaction of an aliphatic polyhydric alcohol and (meth) acrylic acid.
- a hydroxyl group-containing (meth) acrylic acid ester obtained by an esterification reaction of an aliphatic dihydric alcohol and (meth) acrylic acid is particularly preferred.
- 2-hydroxyethyl (meth) An acrylate is mentioned. *
- isocyanates compounds having one or more isocyanate groups in the molecule are preferable, and divalent isocyanate compounds such as tolylene diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate are particularly preferable.
- the polyester (meth) acrylate is preferably a polyester (meth) acrylate obtained by reacting a hydroxyl group-containing polyester with (meth) acrylic acid.
- Preferred as the hydroxyl group-containing polyester used here is an esterification reaction of one or more aliphatic polyhydric alcohols with one or more monobasic acids, polybasic acids, and phenols.
- examples of the aliphatic polyhydric alcohol include the same compounds as those described above.
- monobasic acids include formic acid, acetic acid, butyl carboxylic acid, benzoic acid and the like.
- Examples of the polybasic acid include adipic acid, terephthalic acid, phthalic anhydride, trimellitic acid and the like.
- phenols include phenol, p-nonylphenol, bisphenol A, and the like.
- the polyether (meth) acrylate is a polyether (meth) acrylate obtained by reacting a hydroxyl group-containing polyether with meth (acrylic) acid.
- the hydroxyl group-containing polyether used here is a hydroxyl group-containing polyether obtained by adding one or more alkylene oxides to an aliphatic polyhydric alcohol, The same compounds as those described above can be exemplified.
- the alkylene oxide include ethylene oxide and propylene oxide.
- (meth) acrylic acid ester of alcohols is obtained by reacting an aromatic or aliphatic alcohol having at least one hydroxyl group in the molecule and an alkylene oxide adduct thereof with (meth) acrylic acid.
- (Meth) acrylates such as 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, isoamyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) ) Acrylate, isooctyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanedio Rudi (meth) acrylate, 1,6-hexan
- SA1002 (manufactured by Mitsubishi Chemical Corporation), biscoat 195, biscoat 230, biscoat 260, biscoat 215, biscoat 310, biscoat 214HP, biscoat 295, biscoat 300, biscoat 360, biscoat 360, Biscoat 400, Biscoat 700, Biscoat 540, Biscoat 3000, Viscoat 3700 (above, manufactured by Osaka Organic Chemical Industry Co., Ltd.), Kayarad R-526, HDDA, NPGDA, TPGDA, MANDA, R-551, R-712, R- 604, R-684, PET-30, GPO-303, TMPTA, THE-330, DPHA, DPHA-2H, DPHA-2C, DPHA-2I, D-310, D-330, DPCA-20, DPCA-30, PCA-60, DPCA-120, DN-0075, DN-2475, EB-645, EB-648, EB-3700 (Daicel UCB) T-1420, T-2020, T
- radically polymerizable organic substances may be used alone or in combination of two or more according to the desired performance.
- the photo radical polymerization initiator may be any compound that can initiate radical polymerization upon receiving light irradiation, for example, a ketone such as an acetophenone compound, a benzyl compound, a benzophenone compound, or a thioxanthone compound.
- a ketone such as an acetophenone compound, a benzyl compound, a benzophenone compound, or a thioxanthone compound.
- preferred compounds include oxime compounds and oxime compounds.
- acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, and 2-hydroxymethyl-2.
- benzylic compound examples include benzyl and anisyl.
- benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
- oxime compounds include 1.2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), methanone, (2-methylphenyl) [6-nitro-9- [3- (trimethylsilyl) propyl] -9H-carbazole-3- Yl]-, 1-O-acetyloxime), methanone, (9-ethyl-6-nitro-9H-carbazol-3-yl) (2-methylphenyl), O-acetyloxime, methanone, (9-ethyl- 6-nitro-9H-carbazol-3-yl) [2-methyl-4- (4-morpholinyl) phenyl), O-acetyloxime, methanone, (3,5-dinitrofe ) (9-ethyl,
- thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
- radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium Etc.
- photo radical polymerization initiators can be used alone or in combination of two or more according to the desired performance.
- the radical photopolymerization initiator as described above may be used in a stoichiometric amount with respect to the radical polymerizable organic substance, preferably 0.05 to 10 parts by mass with respect to the radical polymerizable organic substance, More preferably, 0.1 to 10 parts by mass is added. If this range is exceeded, a cured product having sufficient strength may not be obtained, and if it is less than this range, the resin may not be sufficiently cured.
- the thermosetting composition is cured by heating and may be any of a thermal cation curable composition, a thermal anion curable composition, or a thermal radical curable composition. It is preferable because radicals are trapped when the latent antioxidant is heated and activated.
- the thermal radical curable composition contains the latent additive of the present invention as a latent antioxidant and contains the radical polymerizable organic substance and the thermal radical polymerization initiator as essential components.
- thermal radical polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (methylisobutylate), 2,2′-azobis-2,4-dimethylvaleronitrile, Azo initiators such as 1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di (4-t-butylcyclohexyl) )
- Peroxide initiators such as peroxydicarbonate, and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.
- thermosetting composition is dissolved or dispersed in an organic solvent as necessary, and the obtained coating liquid is a known spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, etc. By means, it can be applied on a support substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc., and cured by heating.
- a support substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc.
- the organic solvent is not particularly limited and known and commonly used ones can be used.
- ketones, ethers, amides, alcohols and the like can be preferably used. Specific examples include acetone, methyl ethyl ketone, methyl- n-butyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone, diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, diethylformamide, dimethylacetamide, diethylacetamide, N-methylpyrrolidone, methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, 2- Known solvents such as methoxy-2-propanol and tetraglyme can be used.
- the above-mentioned heat curing is usually performed at a temperature of about 60 ° C. or higher, preferably about 100 to 300 ° C. for about 10 seconds to 3 hours.
- the above-mentioned polymerizable composition is obtained by homopolymerizing or copolymerizing the above radical-polymerizable organic substance by suspension polymerization, continuous polymerization, solution polymerization, emulsion polymerization, bulk polymerization or the like in an organic solvent as necessary.
- the above-mentioned photosensitive composition is a composition whose properties are changed by light irradiation, and a positive resist is one that is soluble to a chemical reaction, and a negative resist is one that is insoluble to a chemical reaction.
- the photosensitive composition contains the latent additive of the present invention as a latent antioxidant, and contains a polymerizable compound having an ethylenically unsaturated bond having an acid value and a radical photopolymerization initiator as essential components.
- Examples of the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid.
- X 41 is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO— or a substituent represented by the above [Chemical Formula 7] to [Chemical Formula 9], wherein the alkylidene group may be substituted with a halogen atom;
- 41 , R 42 , R 43 and R 44 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a halogen atom
- the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom
- r is an integer of 0 to
- polymerizable compounds can be used alone or in combination of two or more, and can be used in combination with a polymerizable compound having an ethylenically unsaturated bond having no acid value. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
- Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, The following compound No. A1-No.
- A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
- a monofunctional or polyfunctional epoxy compound can be used together with the polymerizable compound having an ethylenically unsaturated bond having the acid value.
- the polymerizable compound having an ethylenically unsaturated bond having an acid value preferably has a solid content acid value of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is It is preferable to select so as to satisfy the value.
- Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
- the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers as the polyfunctional epoxy compound because a colored alkali-developable photosensitive composition with better characteristics can be obtained.
- the bisphenol type epoxy compound an epoxy compound represented by the above general formula (I) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
- glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
- novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
- a coloring agent may be further added to the photosensitive composition to form a colored photosensitive composition.
- the cured product of the colored photosensitive composition is suitably used as a color filter.
- the addition amount of the colorant is preferably 0.01 to 50% by mass, and more preferably 0.1 to 30% by mass.
- the colorant examples include dyes and pigments.
- the dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm. , Naphthol compound, quinoline compound, nitro compound, indamine compound, oxazine compound, phthalocyanine compound, cyanine compound, diimmonium compound, cyanoethenyl compound, dicyanostyrene compound, rhodamine compound, perylene compound, polyenenaphtholactam compound, coumarin compound, squarylium compound, croconium Compound, spiropyran compound, spirooxazine compound, merocyanine compound, oxonol compound, styrylation Product, pyrylium compound, rhodanine compound, oxazolone compound, phthalimide compound, cinnoline compound, naphthoquinone compound, azaanthraquinone compound, porphyrin compound
- inorganic pigments or organic pigments can be used.
- inorganic pigment or organic pigment commercially available pigments can also be used.
- a solvent can be further added to the colored photosensitive composition.
- the solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, etc.
- Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate Ester solvents such as n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolv solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; methanol Alcohol solvents such as ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA)
- ketones, ether ester solvents, and the like particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility between the resist and the photopolymerization initiator is good in the photosensitive composition.
- the above-mentioned colored photosensitive composition can further contain an inorganic compound.
- the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
- a dispersant can be added.
- any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
- the colored photosensitive composition includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as cross-linking agents; thickeners can be added.
- thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- plasticizer adhesion promoter
- filler Agents
- leveling agents surface conditioning agents
- antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants
- UV absorbers dispersion aids
- aggregation inhibitors catalysts
- the properties of the cured product of the colored photosensitive composition of the present invention can be improved.
- the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
- Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
- polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
- a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, melamine and the like can be used in combination with the colored photosensitive composition.
- a sulfur atom-containing compound is generally used.
- Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
- the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
- fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
- anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
- silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
- Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
- examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
- the methylol group that is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules to form an oligomer component.
- hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
- alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
- the colored photosensitive composition is a known method such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. It can be applied on the supporting substrate. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
- the active light source used for curing the colored photosensitive composition may be one that emits light having a wavelength of 300 to 450 nm, for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc. Xenon arc or the like can be used.
- the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
- the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
- the colored photosensitive composition is a photocurable paint or varnish, a photocurable adhesive, a printed circuit board, or a color display liquid crystal display such as a color television, PC monitor, portable information terminal, digital camera, etc.
- the colored photosensitive composition is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel.
- the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) irradiating the coating film with active light through a mask having a predetermined pattern shape. It is preferably formed by a step, (3) a step of developing the film after exposure with a developer, and (4) a step of heating the film after development.
- the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
- novel compound of the present invention corresponds to the compounds represented by the following general formula (2), the following general formula (6) and the following general formula (8) among the compounds used in the above-described latent additive of the present invention. To do.
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 201 and R 202 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 204 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to Represents 20 heterocycle-containing groups or trialky
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 202 may be bonded to each other to form a benzene ring or a naphthalene ring
- the plurality of R 202 and R 204 may be the same or different
- X 2 represents an oxygen atom, a sulfur atom, a group represented by the following [Chemical Formula 4],> C ⁇ O, —NH—CO—, —CO—NH—,> NR 12 ,> PR 12 or the following general formula ( 3), (4) or any one of the substituents represented by the group of the following [Chemical Formula 10], wherein R 12 is a hydrogen atom, an aliphatic having 1 to 35 carbon atoms which may have a substituent.
- the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocycle-containing group are a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O.
- O, -S-S-, or -SO 2 - may be replaced by a combination of group selected from the aromatic ring Alternatively, the heterocyclic ring may be condensed with another ring. X 2 may form a ring together with A. )
- Y 1 and Y 5 each independently represent a direct bond and an alkylene group having 1 to 4 carbon atoms
- Y 2 and Y 4 each independently represent an oxygen atom or — NR 13- represents
- R 13 represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms
- Y 3 represents a direct bond
- -NR 16- a divalent carbon atom having 1 to 35 carbon atoms.
- the aromatic ring-containing hydrocarbon group may be replaced by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- R 14 and R 15 are each independently hydrogen Atoms, alkyl groups having 1 to 8 carbon atoms, aryl groups having 6 to 20 carbon atoms, or 7 carbon atoms
- Arylalkyl group of 20, R 16 the number of hydrogen atoms, aliphatic hydrocarbon group which may carbon atoms 1 to 35 which may have a substituent, which may have a substituent group having a carbon atom 6
- Y 6 and Y 8 are each independently, -NR 17 - or be interrupted by oxygen atoms represent also alkylene group having a carbon number of 1 ⁇ 4, Y 7 are, a direct bond, -O -, - S -, - SO 2 -, - CR 18 R 19 - or below in [formula 66] ⁇ represents any of substituents represented by Chemical formula 68], R 17 is hydrogen Represents an atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 18 and R 19 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent.
- R 100 and R 101 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.
- E represents a number from 1 to 4
- f represents a number from 1 to 4.
- R 21 represents a hydrogen atom, an optionally substituted phenyl group, or a cycloalkyl group having 3 to 10 carbon atoms
- R 22 represents an alkyl group having 1 to 10 carbon atoms
- R 102 and R 103 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms.
- i represents a number from 1 to 4
- j represents a number from 1 to 4.
- R 23 and R 24 each independently represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent.
- R 31 represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, or an aromatic group having 6 to 35 carbon atoms which may have a substituent.
- Y 9 and Y 10 each independently represents an alkylene group having 1 to 4 carbon atoms.
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 301 and R 302 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 304 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to 2 carbon atoms.
- R 301 , R 302 and R 304 represents 20 heterocycle-containing groups or trialkylsilyl groups
- the methylene group in the alkyl group or arylalkyl group represented by R 301 , R 302 and R 304 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, — CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —O—CO—S—, —S—CO—O—, — CO—NH—, —NH—CO—, —NH—CO—O—, —NR ′ —,> P ⁇ O, —SS—, —SO 2 — or a combination of groups selected from nitrogen atoms
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 302 may be bonded to each other to form a
- Y 11 represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms.
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—,> CO, — CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,> NR 32 ,> PR 32 or an aliphatic group having 1 to 35 carbon atoms which may have a substituent
- R 32 is a hydrogen atom, an aliphatic
- A represents a 5-membered or 6-membered aromatic ring or heterocyclic ring
- R 401 and R 402 each independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms which may have a substituent, or the number of carbon atoms
- d represents an integer of 1 to 3
- k represents an integer of 1 to 3
- R 404 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 2 to Represents 20 heterocycle-containing groups or trialky
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 402 may be bonded to each other to form a benzene ring or a naphthalene ring
- the plurality of R 402 and R 404 may be the same or different
- n represents a number from 4 to 6
- represents a substituent represented by the following general formula (10) when n 5
- represents a substituent represented by the following general formula (10) when n 6.
- the substituent represented by General formula (11) is represented.
- X 4 may form a ring together with A, and the aromatic ring or heterocyclic ring may be condensed with another ring. )
- Y 12 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a carbon atom.
- Y 13 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms, or a C 2 to 30 carbon atom group. Represents a heterocyclic ring-containing group, and the aliphatic hydrocarbon group may be replaced by a combination of groups selected from —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
- Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (7).
- Y 14 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 to 35 carbon atoms. Represents a heterocyclic ring-containing group, and the aliphatic hydrocarbon group may be replaced by a combination of groups selected from —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—.
- Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (7).
- the obtained white powder crystal was dried under reduced pressure at 60 ° C. for 3 hours to obtain the desired product. It was confirmed by 1 H-NMR and IR that the obtained white powdery crystals were the target product. Moreover, melting
- Example 2-1 and Comparative Example 2-1 Polymerizable composition No. 1 and comparative polymerizable composition No. 1 Preparation of No. 1 In a 50 ml four-necked flask, 2.97 g of methyl methacrylate and 0.03 g of azoisobutyronitrile were added. 1 (Example 2) or Comparative Compound No. 0.01 g of 1 and 7.00 g of toluene were added, and the mixture was stirred at 80 ° C. for 2 hours. GPC was measured and the molecular weight of the polymer was measured. The results are shown in [Table 4].
- the comparative polymerizable composition to which the compound having a phenol group is added may cause polymerization inhibition, whereas the polymerizable composition to which the latent additive of the present invention is added may not cause polymerization inhibition. it is obvious.
- Photosensitive Composition No. 9 and comparative photocurable composition No. 9-No. Preparation of 10 SPC-1000 (manufactured by Showa Denko KK, PGMEA solution with a solid content of 29%) 50.9 g, Aronix M-450 (manufactured by Toagosei Co., Ltd.) 11.9 g, NCI-930 (manufactured by ADEKA) 0.3 g, 34.0 g of PGMEA, 2.9 g of FZ2122 (manufactured by Toray Dow Corning Co., Ltd., PGMEA solution with a solid content of 1%) and 0.81 g of the additive described in [Table 6] were mixed, and stirred until insoluble matter disappeared, and photosensitive Composition No. 9 and comparative photosensitive composition No. 9-No. 10 was obtained.
- thermosetting composition No. 1 and comparative thermosetting composition No. 1 1-No. Preparation of 2 According to the formulation of [Table 7], the resin and the additive were mixed and stirred at 50 ° C. at a stirring speed of 300 to 400 rpm for 1 hour to be uniformly dissolved. 0.75 g of CP-66 (manufactured by ADEKA) was added as a thermal initiator and stirred at a stirring speed of 400 to 500 rpm for 1 hour. In addition, a numerical value represents a mass part.
- the absorbance of the coating film before baking (after exposure) and the absorbance of the coating film after baking at the maximum absorption wavelength ( ⁇ max) of the colorant used were measured, and the absorbance of the coating film before baking (after exposure) was taken as 100.
- the relative strength was evaluated. In addition, it shows that heat resistance is so high that the light absorbency of the coating film after baking is close to 100. The results are shown in [Table 9].
- the colored photosensitive composition of the present invention has higher heat resistance than the comparative colored photosensitive composition because it contains a latent additive. It is.
- the resulting coating film was exposed with an ultra-high pressure mercury lamp through a mask at a gap of 20 ⁇ m (50mJ / cm 2 ⁇ 30mJ / cm 2 every 8 divided up 270mJ / cm 2) to.
- the exposed coating film was developed with an alkali developer and then baked under conditions of 230 ° C. ⁇ 30 min.
- the line width at each exposure dose at a mask opening of 20 ⁇ m was plotted, and the exposure dose at which the line width was 20 ⁇ m was defined as the line width sensitivity.
- the results are shown in [Table 10]. It can be said that the smaller the value, the higher the sensitivity.
- comparative compound No. which is a phenolic antioxidant conventionally used is used.
- Comparative colored photosensitive composition No. 2 using 4 to No. The cured product of No. 6 has a low line width sensitivity and is inhibited from curing, but the colored photosensitive composition No. 6 using the latent antioxidant of the present invention was used.
- 1-No. The cured product of No. 3 has high line width sensitivity and does not inhibit curing.
- the photosensitive composition of the present invention has higher heat resistance than the comparative photosensitive composition because it contains a latent additive.
- comparative compound No. which is a phenolic antioxidant conventionally used is used.
- thermosetting A fluororesin spacer (gap member) having a thickness of 0.5 to 1.0 mm on a glass substrate on which an untreated PET film is attached. ), And a glass substrate that has been subjected to a mold release treatment through this spacer, and the thermosetting composition No. obtained above is stacked. 1 and comparative thermosetting composition No. 1 1-No. 2 was injected. The film was heated in an oven at 150 ° C. for 1 hour and post-cured. It took out from the glass substrate after cooling, and peeled the resin cured film from the glass substrate. The cured product was heated at 200 ° C./1 h to conduct a heat resistance test, and the transmittance of the cured product before and after the heat resistance test was measured with an absorptiometer. The results are shown in [Table 13].
- thermosetting composition No. with the additive of the present invention added. No. 1 and comparative thermosetting composition No. to which a comparative compound was added. 1 is a comparative thermosetting composition No. 1 to which no additive was added. Compared to 2, the transmittance at 400 nm after the heat test is high, and the heat resistance is high. Further, from [Table 14], since the additive of the present invention protects the phenol group, the pot life is longer than that of the comparative compound, and the storage stability is excellent. Therefore, it is clear that the additive of the present invention is suitable for a thermosetting composition.
- Comparative Evaluation Example 7-1 the transmittance increased after firing because the photoradical polymerization initiator that absorbs 365 nm light was thermally decomposed during firing and no longer absorbs 365 nm. Similarly in Evaluation Example 7-1, the radical photopolymerization initiator was thermally decomposed, but the latent additive of the present invention was deprotected after firing and acted as an ultraviolet absorber that absorbs 365 nm light. It is clear.
- the latent additive of the present invention becomes a phenolic additive by heating.
- the latent additive of the present invention is inactive at room temperature and becomes active by heating to a predetermined temperature, and the cured product of the composition containing the latent additive is It is clear that it has excellent heat resistance without causing curing inhibition.
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Abstract
Description
R1及びR2は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R4は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R1、R2及びR4で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-又は-SO2-から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR2同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR2及びR4はそれぞれ同じでも異なっていてもよく、
nは、1~10の整数を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
Xは、直接結合、窒素原子、酸素原子、硫黄原子、リン原子、下記〔化2〕で表される基、>P=O、>C=O、>NR10、>PR10、-OR10、-SR10、-NR10R11又は-PR10R11又はnと同数の価数を有する置換基を有していてもよい炭素原子数1~120の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基、置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、R10及びR11は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基は、炭素一炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、-SO2-又は窒素原子から選ばれた基の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。但し、Xが窒素原子、リン原子又は下記〔化2〕で表される基の場合、nは3であり、Xが酸素原子又は硫黄原子の場合、nは2であり、Xが>C=O、-NH-CO-、-CO-NH-、>NR10又は>PR10の場合、nは2であり、Xが-OR10、-SR10、-NR10R11又は-PR10R11の場合、nが1であり、Xは、Aと一緒になって環を形成していてもよい。)
R201及びR202は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R204は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
該R201、R202及びR204で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR202同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR202及びR204はそれぞれ同じでも異なっていてもよく、
X2は、酸素原子、硫黄原子、下記〔化4〕で表される基、>C=O、-NH-CO-、-CO-NH-、>NR12、>PR12又は下記一般式(3)、(4)あるいは下記[化10]の群で表されるいずれかの置換基を表し、R12は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基は、炭素一炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2-から選ばれた基の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。
X2は、Aと一緒になって環を形成していてもよい。)
R301及びR302は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R304は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R301、R302及びR304で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、-SO2-又は窒素原子から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR302同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR302及びR304はそれぞれ同じでも異なっていてもよく、
X3は、下記一般式(7)で表される置換基を表す。
X3は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
R401及びR402は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R404は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R401、R402及びR404で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR402同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR402及びR404はそれぞれ同じでも異なっていてもよく、
nは4~6の数を表し、
X4は、n=4のとき下記一般式(9)で表される置換基を表し、n=5のとき下記一般式(10)で表される置換基を表し、n=6のとき下記一般式(11)で表される置換基を表す。
X4は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
潜在性添加剤とは、常温あるいは150℃以下のプリベーク工程では不活性であり、100~250℃で加熱するか、あるいは酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して活性となるものであり、具体的には、潜在性酸化防止剤、潜在性紫外線吸収剤等の潜在性樹脂添加剤;感熱紙用潜在性顕色剤;感熱紙用潜在性保存安定剤;潜在性硬化剤等が挙げられる。
R1及びR2で表されるハロゲン原子としては、フッ素、塩素、臭素、ヨウ素が挙げられ、
R1、R2及びR4で表される炭素原子数1~40のアルキル基としては、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、iso-アミル、tert-アミル、シクロペンチル、ヘキシル、2-ヘキシル、3-ヘキシル、シクロヘキシル、4-メチルシクロヘキシル、ヘプチル、2-ヘプチル、3-ヘプチル、iso-ヘプチル、tert-ヘプチル、1-オクチル、iso-オクチル、tert-オクチル、アダマンチル等が挙げられ、
R1及びR2で表される炭素原子数1~8のアルコキシ基としては、メチルオキシ、エチルオキシ、iso-プロピルオキシ、ブチルオキシ、sec-ブチルオキシ、tert-ブチルオキシ、iso-ブチルオキシ、アミルオキシ、iso-アミルオキシ、tert-アミルオキシ、ヘキシルオキシ、2-ヘキシルオキシ、3-ヘキシルオキシ、シクロヘキシルオキシ、4-メチルシクロヘキシルオキシ、ヘプチルオキシ、2-ヘプチルオキシ、3-ヘプチルオキシ、iso-ヘプチルオキシ、tert-ヘプチルオキシ、1-オクチルオキシ、iso-オクチルオキシ、tert-オクチルオキシ等が挙げられ、
R1及びR2で表される炭素原子数1~8のアルキル基及びアルコキシ基を置換する置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられる。
R4で表される炭素原子数6~20のアリール基としては、フェニル、ナフチル、アントラセニル等が挙げられ、
R4で表される炭素原子数7~20のアリールアルキル基としては、ベンジル、フルオレニル、インデニル、9-フルオレニルメチル基等が挙げられ、
R4で表される炭素原子数2~20の複素環含有基としては、ピリジル、ピリミジル、ピリダジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、2-ピロリジノン-1-イル、2-ピペリドン-1-イル、2,4-ジオキシイミダゾリジン-3-イル、2,4-ジオキシオキサゾリジン-3-イル等が挙げられ、
R4で表されるトリアルキルシリル基としては、トリメチルシラン、トリエチルシラン、エチルジメチルシラン等が挙げられる。
R4の中でも、炭素原子数1~8のアルキル基の酸素原子側の末端に-CO-O-が結合しているものが、潜在性添加剤として効率的に機能を発現するので好ましい。
置換基を有してもよい炭素原子数6~35の一価の芳香環含有炭化水素基としては、ベンジル、フェネチル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等のアリールアルキル基;フェニル、ナフチル等のアリール基;フェノキシ、ナフチルオキシ等のアリールオキシ基;フェニルチオ、ナフチルチオ等のアリールチオ基等が挙げられ、
置換基を有してもよい炭素原子数2~35の一価の複素環含有基としては、ピリジル、ピリミジル、ピリダジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、2-ピロリジノン-1-イル、2-ピペリドン-1-イル、2,4-ジオキシイミダゾリジン-3-イル、2,4-ジオキシオキサゾリジン-3-イル、ベンゾトリアゾイル等が挙げられる。
置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられ、これらの基は更に置換されていてもよい。また、カルボキシル基及びスルホ基は塩を形成していてもよい。
二価の炭素原子数6~35の芳香環含有炭化水素基としては、フェニレン、ナフチレン、ビフェニル等の基が、Z1及びZ2で置換された二価の基等が挙げられ、
二価の炭素原子数2~35の複素環含有基としては、ピリジン、ピラジン、ピペリジン、ピペラジン、ピリミジン、ピリダジン、トリアジン、ヘキサヒドロトリアジン、フラン、テトラヒドロフラン、クロマン、キサンテン、チオフェン、チオラン等が、Z1及びZ2で置換された二価の基が挙げられる。
これらの基はハロゲン原子、シアノ基、ニトロ基又は炭素原子数1~8のアルコキシ基でさらに置換されていてもよい。
炭素原子数6~20のアリール基としては、フェニル、ナフチル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-ビニルフェニル、3-iso-プロピルフェニル、4-iso-プロピルフェニル、4-ブチルフェニル、4-iso-ブチルフェニル、4-tert-ブチルフェニル、4-ヘキシルフェニル、4-シクロヘキシルフェニル、4-オクチルフェニル、4-(2-エチルヘキシル)フェニル、2,3-ジメチルフェニル、2,4-ジメチルフェニル、2,5-ジメチルフェニル、2,6-ジメチルフェニル、3,4-ジメチルフェニル、3,5-ジメチルフェニル、2,4-ジ-tert-ブチルフェニル、2,5-ジ-tert-ブチルフェニル、2,6-ジ-tert-ブチルフェニル、2,4-ジ-tert-ペンチルフェニル、2,5-ジ-tert-アミルフェニル、2,4,5-トリメチルフェニル等が挙げられ、
炭素原子数7~20のアリールアルキル基としては、ベンジル、フェネチル、2-フェニルプロパン-2-イル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等が挙げられる。
R22で表される炭素原子数1~10のアルキル基、炭素原子数1~10のアルコキシ基及びハロゲン原子としては、上記一般式(1)の説明で例示したアルキル基、アルコキシ基及びハロゲン原子等が挙げられ、
炭素原子数2~10のアルケニル基としては、ビニル、アリル、1-プロペニル、イソプロペニル、2-ブテニル、1,3-ブタジエニル、2-ペンテニル、2-オクテニル等が挙げられ、
上記R22におけるアルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、その置換位置は制限されない。
炭素原子数6~20のアリールオキシ基としては、フェニルオキシ、ナフチルオキシ、2-メチルフェニルオキシ、3-メチルフェニルオキシ、4-メチルフェニルオキシ、4-ビニルフェニル二オキシ、3-iso-プロピルフェニルオキシ、4-iso-プロピルフェニルオキシ、4-ブチルフェニルオキシ、4-tert-ブチルフェニルオキシ、4-へキシルフェニルオキシ、4-シクロヘキシルフェニルオキシ、4-オクチルフェニルオキシ、4-(2-エチルヘキシル)フェニルオキシ、2,3-ジメチルフェニルオキシ、2,4-ジメチルフェニルオキシ、2,5-ジメチルフェニルオキシ、2.6-ジメチルフェニルオキシ、3.4-ジメチルフェニルオキシ、3.5-ジメチルフェニルオキシ、2,4-ジーtert-ブチルフェニルオキシ、2,5-ジーtert-ブチルフェニルオキシ、2,6-ジーtert-ブチルフェニルオキシ、2.4-ジーtert-ペンチルフェニルオキシ、2,5-tert-アミルフェニルオキシ、4-シクロへキシルフェニルオキシ、2,4,5-トリメチルフェニルオキシ、フェロセニルオキシ等の基及びこれらの基がハロゲン原子で置換された基が奉げられ、
炭素原子数6~20のアリールチオ基としては、上記ハロゲン原子で置換されていてもよい炭素原子数6~20のアリールオキシ基の酸素原子を硫黄原子に置換した基等が奉げられ、
炭素原子数8~20のアリールアルケニル基としては、上記ハロゲン原子で置換されていてもよい炭素原子数6-20のアリールオキシ基の酸素原子をビニル、アリル、1-プロペニル、イソプロペニル、2-ブテニル、1,3-ブタジエニル、2-ペンテニル、2-オクテニル等のアルケニル基で置換した基等が挙げられ、
炭素原子数2-20の複素環含有基としては、ピリジン、ピラジン、ピペリジン、ピペラジン、ピリミジン、ピリダジン、トリアジン、ヘキサヒドロトリアジン、フラン、テトラヒドロフラン、クロマン、キサンテン、チオフェン、チオフラン等の基及びこれらの基がハロゲン原子で置換された基等が挙げられる。
三価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(12)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2及びZ3で置換された三価の基が挙げられ、
三価の炭素原子数2~35の複素環含有基としては、上記一般式(12)におけるX1の説明で例示した複素環含有基が、Z1、Z2及びZ3で置換された三価の基が挙げられる。
四価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(2)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3及びZ4で置換された四価の基が挙げられ、
四価の炭素原子数2~35の複素環含有基としては、上記一般式(2)におけるX1の説明で例示した複素環含有基が、Z1、Z2、Z3及びZ4で置換された四価の基が挙げられる。
五価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(12)におけるX1の説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基が挙げられ、
五価の炭素原子数2~35の複素環含有基としては、上記一般式(12)におけるX1で説明で例示した複素環含有基が、Z1、Z2、Z3、Z4及びZ5で置換された五価の基が挙げられる。
六価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(12)におけるX1で説明で例示した芳香環含有炭化水素基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基が挙げられ、
六価の炭素原子数2~35の複素環含有基としては、上記一般式(12)におけるX1の説明で例示した複素環含有基が、Z1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基が挙げられる。
本発明の潜在性添加剤は、潜在性酸化防止剤あるいは潜在性紫外線吸収剤として光硬化性組成物、熱硬化性組成物、感光性組成物あるいは重合性組成物に用いられる他、潜在性顕色剤として感熱材料にも用いられる。
上記光硬化性組成物において、本発明の潜在性添加剤の含有量は、0.001~20質量%が好ましく、0.005~5質量%がより好ましい。
上記熱硬化性組成物において、本発明の潜在性添加剤の含有量は、0.001~20質量%が好ましく、0.005~5質量%がより好ましい。
上記感光性組成物において、本発明の潜在性添加剤の含有量は、0.001~20質量%が好ましく、0.005~5質量%がより好ましい。
上記重合性組成物において、本発明の潜在性添加剤の含有量は、0.001~20質量%が好ましく、0.005~5質量%がより好ましい。
該光ラジカル硬化性組成物は、本発明の潜在性添加剤を潜在性酸化防止剤として含む他、ラジカル重合性有機物質及び光ラジカル重合開始剤を必須成分とする。
、配合して使用することができる。なお、ラジカル重合性有機物質のうち50質量%以上
が、分子中に(メタ)アクリル基を有する化合物であることが好ましい。
該熱ラジカル硬化性組成物は、本発明の潜在性添加剤を潜在性酸化防止剤として含む他、上記ラジカル重合性有機物質及び熱ラジカル重合開始剤を必須成分とする。
ルグリシジルエーテル、フェニルグリシジルエーテル、p-メトキシグリシジルエーテル、p-ブチルフェノールグリシジルエーテル、クレジルグリシジルエーテル、2-メチルクレジルグリシジルエーテル、4-ノニルフェニルグリシジルエーテル、ベンジルグリシジルエーテル、p-クミルフェニルグリシジルエーテル、トリチルグリシジルエーテル、2,3-エポキシプロピルメタクリレート、エポキシ化大豆油、エポキシ化アマニ油、グリシジルブチレート、ビニルシクロヘキサンモノオキシド、1,2-エポキシ-4-ビニルシクロヘキサン、スチレンオキシド、ピネンオキシド、メチルスチレンオキシド、シクロヘキセンオキシド、プロピレンオキシド、等が挙げられる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4-エポキシ-6-メチルシクロヘキシルメチル-3,4-エポキシ-6-メチルシクロヘキサンカルボキシレート、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、1-エポキシエチル-3,4-エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジル-p-アミノフェノール、N,N-ジグリシジルアニリン等のグリシジルアミン類;1,3-ジグリシジル-5,5-ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物、トリフェニルメタン型エポキシ化合物、ジシクロペンタジエン型エポキシ化合物等を用いることもできる。
上記着色感光性組成物において、着色剤の添加量は、0.01~50質量%が好ましく、0.1~30質量%がより好ましい。
染料としては、380~1200nmに吸収を有する化合物であれば特に限定されないが、例えば、アゾ化合物、アントラキノン化合物、インジゴイド化合物、トリアリールメタン化合物、キサンテン化合物、アリザリン化合物、アクリジン化合物、スチルベン化合物、チアゾール化合物、ナフトール化合物、キノリン化合物、ニトロ化合物、インダミン化合物、オキサジン化合物、フタロシアニン化合物、シアニン化合物、ジインモニウム化合物、シアノエテニル化合物、ジシアノスチレン化合物、ローダミン化合物、ペリレン化合物、ポリエンナフトラクタム化合物、クマリン化合物、スクアリリウム化合物、クロコニウム化合物、スピロピラン化合物、スピロオキサジン化合物、メロシアニン化合物、オキソノール化合物、スチリル化合物、ピリリウム化合物、ローダニン化合物、オキサゾロン化合物、フタルイミド化合物、シンノリン化合物、ナフトキノン化合物、アザアントラキノン化合物、ポルフィリン化合物、アザポルフィリン化合物、ピロメテン化合物、キナクリドン化合物、ジケトピロロピロール化合物、インジゴ化合物、アクリジン化合物、アジン化合物、アゾメチン化合物、アニリン化合物、キナクリドン化合物、キノフタロン化合物、キノンイミン化合物、イリジウム錯体化合物、ユーロピウム錯体化合物等の染料等が挙げられ、これらは複数を混合して用いてもよい。
ルキルエーテル化された化合物を挙げることができる。ここで、アルキルエーテルを構成するアルキル基としては、メチル基、エチル基又はブチル基が挙げられ、互いに同一であってもよいし、異なっていてもよい。また、アルキルエーテル化されていないメチロール基は、一分子内で自己縮合していてもよく、二分子間で縮合して、その結果オリゴマー成分が形成されていてもよい。具体的には、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン、テトラメトキシメチルグリコールウリル、テトラブトキシメチルグリコールウリル等を用いることができる。これらのなかでも、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン等のアルキルエーテル化されたメラミンが好ましい。
R201及びR202は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R204は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
該R201、R202及びR204で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR202同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR202及びR204はそれぞれ同じでも異なっていてもよく、
X2は、酸素原子、硫黄原子、下記〔化4〕で表される基、>C=O、-NH-CO-、-CO-NH-、>NR12、>PR12又は下記一般式(3)、(4)あるいは下記[化10]の群で表されるいずれかの置換基を表し、R12は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基は、炭素一炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2-から選ばれた基の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。
X2は、Aと一緒になって環を形成していてもよい。)
R301及びR302は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R304は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R301、R302及びR304で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、-SO2-又は窒素原子から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR302同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR302及びR304はそれぞれ同じでも異なっていてもよく、
X3は、下記一般式(7)で表される置換基を表す。
X3は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
R401及びR402は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R404は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R401、R402及びR404で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR402同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR402及びR404はそれぞれ同じでも異なっていてもよく、
nは4~6の数を表し、
X4は、n=4のとき下記一般式(9)で表される置換基を表し、n=5のとき下記一般式(10)で表される置換基を表し、n=6のとき下記一般式(11)で表される置換基を表す。
X4は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
フェノール化合物0.01mol、二炭酸ジ-tert-ブチル0.05mol及びピリジン30gを混合し、窒素雰囲気下、室温で4-ジメチルアミノピリジン0.025molを加え、60℃で3時間撹拌した。室温まで冷却後、反応液をイオン交換水150gに注ぎ、クロロホルム200gを加えて油水分離を行った。有機層を無水硫酸ナトリウムで乾燥後、溶媒を留去し、残渣にメタノール100gを加えて晶析を行った。得られた白色粉状結晶を60℃で3時間減圧乾燥させ、目的物を得た。得られた白色粉状結晶が目的物であることは1H-NMR、IRにて確認した。また、融点を測定した。結果を[表1]~[表3]に示す。
製造例1-1と同様にして、化合物No.2~No.10を合成した。
50ml四つ口フラスコに、メタクリル酸メチル2.97g及びアゾイソブチロニトリ ル0.03gを入れ、化合物No.1(実施例2)又は比較化合物No.1を0.01 gとトルエン7.00gを加え、80℃で2時間撹拌した。GPCを測定し重合物の分 子量を測定した。結果を〔表4〕に示す。
<ステップ1>感光性組成物No.1~No.8及び比較感光性組成物No.1~No.8の調製
SPC-1000(昭和電工社製、固形分29%のPGMEA溶液)50.9g、アロニックスM-450(東亜合成社製)11.9g、OXE-01(BASF社製)1.04g、PGMEA34.0g、FZ2122(東レ・ダウコーニング社製、固形分1%のPGMEA溶液)2.9g及び[表5]記載の潜在性添加剤0.81gを混合し、不溶物が無くなるまで撹拌し、感光性組成物No.1~No.8及び比較感光性組成物No.1~No.8を得た。
着色剤0.10gに、PGMEA1.90gを加え、撹拌して溶解させた。
ステップ1で得られた感光性組成物No.1~No.8及び比較感光性組成物No.1~No.8を2.50gとステップ2で得られた着色剤溶液No.1~No.8の1.00gとを[表5]記載のように混合して均一になるまで撹拌し、着色感光性組成物No.1~No.8及び比較着色感光性組成物No.1~No.8を得た。
SPC-1000(昭和電工社製、固形分29%のPGMEA溶液)50.9g、アロニックスM-450(東亜合成社製)11.9g、NCI-930(ADEKA社製)0.3g、PGMEA34.0g、FZ2122(東レ・ダウコーニング社製、固形分1%のPGMEA溶液)2.9g及び[表6]記載の添加剤0.81gを混合し、不溶物が無くなるまで撹拌し、感光性組成物No.9及び比較感光性組成物No.9~No.10を得た。
[表7]の配合に従って樹脂及び添加剤を混合し、50℃で300~400rpmの撹拌速度で1時間撹拌して均一に溶解させた。熱開始剤としてCP-66(ADEKA社製)0.75gを加えて撹拌速度400~500rpmで1時間撹拌した。尚、数値は質量部を表す。
<ステップ1>光硬化性組成物No.1及び比較光硬化性組成物No.1~No.2の調製
SPC-1000(昭和電工社製、固形分29%のPGMEA溶液)49.6g、アロニックスM-450(東亜合成社製)11.5g、OXE-01(BASF社製)1.0g、PGMEA35.0g、FZ2122(東レ・ダウコーニング社製、固形分1%のPGMEA溶液)2.9g及び[表8]記載の添加剤2.0gを混合し、光硬化性組成物No.1及び比較光硬化性組成物No.1~No.2を得た。
上記で得られた着色感光性組成物No.1~No.8並びに比較着色感光性組成物No.1~No.8をガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に超高圧水銀ランプで露光(150mJ/cm2)した。露光後の塗膜を、230℃×30minの条件で焼成した。用いた着色剤の極大吸収波長(λmax)における焼成前(露光後)の塗膜の吸光度と焼成後の塗膜の吸光度を測定し、焼成前(露光後)の塗膜の吸光度を100としたときの相対強度として評価した。尚、焼成後の塗膜の吸光度が100に近いほど耐熱性が高いことを示す。結果を[表9]に示す。
実施例3-1~3-3で調製した着色感光性組成物No.1~No.3並びに比較例3-1~3-3で調製した比較着色感光性組成物No.1~No.3、及び、比較着色感光性組成物No.1~No.3にそれぞれ比較化合物No.2の0.81gを加えた比較着色感光性組成物No.4~No.6を、それぞれガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に20μmのギャップをおいたマスクを介し超高圧水銀ランプで露光(50mJ/cm2~270mJ/cm2まで30mJ/cm2おき8分割)した。露光後の塗膜を、アルカリ現像液で現像を行った後、230℃×30minの条件で焼成した。マスク開口20μmにおいて各露光量での線幅をプロットし、線幅が20μmになる露光量を線幅感度とした。結果を[表10]に示す。尚、値が小さいほど感度が高いと言える。
上記で得られた感光性組成物No.9並びに比較感光性組成物No.9~No.10について、上記評価例1と同様に耐熱性評価を行った。結果を[表11]に示す。
上記で得られた感光性組成物No.9並びに比較感光性組成物No.9~No.10をガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に超高圧水銀ランプで露光(150mJ/cm2)した。露光後の塗膜を、230℃×90minの条件で焼成した。焼成後の塗膜の透過率を測定して評価した。尚、焼成後の塗膜の透過率が100に近いほど耐熱性が高いことを示す。結果を[表11]に示す。
上記で得られた感光性組成物No.9並びに比較感光性組成物No.9~No.10について、上記評価例1と同様に線幅感度の測定を行った。結果を[表12]に示す。
未処理のPETフィルムを貼り付けたガラス基板に、0.5~1.0mm厚のフッ素樹脂スペーサー(間隙部材)を設け、このスペーサーを介して離型処理を施したガラス基板を重ね、上記で得られた熱硬化性組成物No.1及び比較熱硬化性組成物No.1~No.2を注入した。オーブン中150℃で1時間加熱し、ポストキュアを行った。冷却後にガラス基板から取り出し、ガラス基板から樹脂硬化膜を剥離した。硬化物を200℃/1hで加熱して耐熱性試験を行い、耐熱性試験前後の硬化物の透過率を吸光光度計で測定した。結果を[表13]に示す。
上記で得られた熱硬化性組成物No.1及び比較熱硬化性組成物No.1について、冷暗所に放置して、粘度が30%増加するまでの日数を数えてポットライフ評価とした。結果を[表14]に示す。
上記で得られた光硬化性組成物No.1並びに比較光硬化性組成物No.2をガラス基板に410rpm×7secの条件で塗工し、ホットプレートで乾燥(90℃、90sec)させた。得られた塗膜に超高圧水銀ランプで露光(150mJ/cm2)した。露光後の塗膜を、230℃×30minの条件で焼成した。焼成前(露光後)の塗膜の透過率と焼成後の塗膜の365nmにおける透過率を測定した。尚、比較光硬化性組成物No.1は、溶解せず白濁したため評価を行わなかった。結果を[表15]に示す。
化合物No.1を5mg測りとり、熱質量測定装置にて室温から230℃まで昇温(10℃/min)した後、30分間230℃で加熱下においたところ、26質量%の減少が見られた。すなわち、この減少分はt-ブトキシカルボニル基に相当し、加熱により脱保護が行われたことを示唆している。また、1H-NMR、IR測定を行い、フェノールが生成していることを確認した。
Claims (7)
- 下記一般式(1)で表される潜在性添加剤。
R1及びR2は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R4は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R1、R2及びR4で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-又は-SO2-から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR2同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR2及びR4はそれぞれ同じでも異なっていてもよく、
nは、1~10の整数を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
Xは、直接結合、窒素原子、酸素原子、硫黄原子、リン原子、下記〔化2〕で表される基、>P=O、>C=O、>NR10、>PR10、-OR10、-SR10、-NR10R11又は-PR10R11又はnと同数の価数を有する置換基を有していてもよい炭素原子数1~120の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基、置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、R10及びR11は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基は、炭素一炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、-SO2-又は窒素原子から選ばれた基の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。但し、Xが窒素原子、リン原子又は下記〔化2〕で表される基の場合、nは3であり、Xが酸素原子又は硫黄原子の場合、nは2であり、Xが>C=O、-NH-CO-、-CO-NH-、>NR10又は>PR10の場合、nは2であり、Xが-OR10、-SR10、-NR10R11又は-PR10R11の場合、nが1であり、Xは、Aと一緒になって環を形成していてもよい。)
- 上記一般式(1)中、Aがベンゼン環であることを特徴とする請求項1に記載の潜在性添加剤。
- 上記一般式(1)中、R4が炭素原子数2~9のアルコキシカルボニル基であることを特徴とする請求項1又は2に記載の潜在性添加剤。
- 請求項1~3のいずれか1項に記載の潜在性添加剤を含有する組成物。
- 下記一般式(2)で表される化合物。
R201及びR202は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R204は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
該R201、R202及びR204で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR202同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR202及びR204はそれぞれ同じでも異なっていてもよく、
X2は、酸素原子、硫黄原子、下記〔化4〕で表される基、>C=O、-NH-CO-、-CO-NH-、>NR12、>PR12又は下記一般式(3)、(4)あるいは下記[化10]の群で表されるいずれかの置換基を表し、R12は、水素原子、置換基を有していてもよい炭素原子数1~35の脂肪族炭化水素基、置換基を有していてもよい炭素原子数6~35の芳香環含有炭化水素基又は置換基を有していてもよい炭素原子数2~35の複素環含有基を表し、該脂肪族炭化水素基、芳香環含有炭化水素基及び複素環含有基は、炭素一炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2-から選ばれた基の組み合わせで置き換わっていてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。
X2は、Aと一緒になって環を形成していてもよい。)
- 下記一般式(6)で表される化合物。
R301及びR302は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R304は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R301、R302及びR304で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、-SO2-又は窒素原子から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR302同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR302及びR304はそれぞれ同じでも異なっていてもよく、
X3は、下記一般式(7)で表される置換基を表す。
X3は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
- 下記一般式(8)で表される化合物。
R401及びR402は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有していてもよい炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
dは、1~3の整数を表し、
kは、1~3の整数を表し、
R404は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R401、R402及びR404で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-O-CO-S-、-S-CO-O-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、>P=O、-S-S-、又は-SO2から選ばれた基の組み合わせで置き換わっていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR402同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
複数のR402及びR404はそれぞれ同じでも異なっていてもよく、
nは4~6の数を表し、
X4は、n=4のとき下記一般式(9)で表される置換基を表し、n=5のとき下記一般式(10)で表される置換基を表し、n=6のとき下記一般式(11)で表される置換基を表す。
X4は、Aと一緒になって環を形成していてもよく、上記芳香環又は複素環は、他の環と縮合されていてもよい。)
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EP3753997A1 (en) | 2020-12-23 |
KR20200125749A (ko) | 2020-11-04 |
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US20150291772A1 (en) | 2015-10-15 |
TWI598684B (zh) | 2017-09-11 |
EP2881450A4 (en) | 2016-02-10 |
CN104334684B (zh) | 2019-08-27 |
JP6312259B2 (ja) | 2018-04-18 |
CN104334684A (zh) | 2015-02-04 |
CN107817650B (zh) | 2024-07-02 |
KR20150040797A (ko) | 2015-04-15 |
KR102398814B1 (ko) | 2022-05-17 |
EP2881450B1 (en) | 2020-09-09 |
JP6741711B2 (ja) | 2020-08-19 |
KR102171002B1 (ko) | 2020-10-28 |
EP2881450A1 (en) | 2015-06-10 |
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