CN108473609A

CN108473609A - Photosensitive composite and new compound

Info

Publication number: CN108473609A
Application number: CN201780005927.6A
Authority: CN
Inventors: 松井依纯; 冈田光裕
Original assignee: Asahi Denka Kogyo KK
Current assignee: Adeka Corp
Priority date: 2016-03-31
Filing date: 2017-03-23
Publication date: 2018-08-31
Anticipated expiration: 2037-03-23
Also published as: JP6889151B2; KR102316645B1; TWI771294B; JPWO2017170182A1; CN108473609B; TW201806918A; WO2017170182A1; KR20180132599A

Abstract

A kind of photosensitive composite contains the compound with the substituent group represented by the following general formula (1).(in formula, R¹And R²Separately indicate hydrogen atom, halogen atom, cyano, hydroxyl, nitro, carboxyl, sometimes also with substituent group carbon atom number be 1~40 alkyl, carbon atom number be 6~20 aryl, carbon atom number be 7~20 aryl alkyl, carbon atom number be 2~20 contain heterocyclic group or trialkylsilkl, j indicates that 1~3 number, * refer in the parts * and adjacent group bonding.)

Description

Photosensitive composite and new compound

Technical field

The present invention relates to containing with specific structure, at normal temperatures for it is nonactive and as defined in be heated to temperature by It is activated to show the photosensitive composite and new compound of the compound of function.In turn, the present invention relates in the sense Added with the coloring photosensitive combination of colorant and the colour filter of the coloring photosensitive combination has been used in photosensitiveness composition.

Background technology

In order to which the weatherability or heat resistance that make photosensitive composite improve, it is known to add ultra-violet absorber or anti-oxidant Agent and make its stabilized method (Patent Documents 1 to 4).

Since phenolic antioxidant and ultra-violet absorber have the free radical for capturing the deterioration for largely effecting on polymer If effect is worked so add them in polymerization system generally as so-called polymerization inhibitor, cause solidification hinder at Therefore latency additive (patent document 5) is developed for problem.

But used the exhaust of the composition of previous latency additive more, it is dirty that accordingly, there exist heating devices The problem of dye or the physical property of composition decline.There are problems that the pollution of device or the reduction of physical property.In addition, using The solvent resistance of previous its solidfied material of the composition of latency additive is low, therefore causes the dissolution of solidfied material, such as also deposits The problem of the brightness for making colour filter declines.

In addition, in patent document 6, disclosing the triallyl oxybenzene compound useful as curing agent, but do not teach Show the photosensitive composite containing the triallyl oxybenzene compound.

Existing technical literature

Patent document

Patent document 1：Japanese Unexamined Patent Publication 2011-048382 bulletins

Patent document 2：No. 2016/016919 specification of U.S. Patent Application Publication No.

Patent document 3：Japanese Unexamined Patent Publication 2015-108649 bulletins

Patent document 4：Japanese Unexamined Patent Publication 2015-132791 bulletins

Patent document 5：International Publication No. 2014/021023

Patent document 6：Japanese Unexamined Patent Publication 3-232832 bulletins

Invention content

Therefore, it is nonactive at normal temperatures and by being heated to defined temperature the purpose of the present invention is to provide having used And it is activated show the compound of the function as antioxidant or ultra-violet absorber, exhaust less and solidfied material The high photosensitive composite of solvent resistance.In addition, another object of the present invention is to provide add in above-mentioned photosensitive composite There are the coloring photosensitive combination of colorant, particularly the coloring photosensitive combination of suitable colour filter.

Further investigation has been repeated in the inventors of the present invention, as a result recognizes：The chemical combination with specific protecting group is used The exhaust of the photosensitive composite of object is few, and the solvent resistance of its solidfied material is high, recognizes in addition：In above-mentioned photosensitive composite In the brightness of optical filter (especially colour filter) will not be made to decline added with the coloring photosensitive combination of colorant, be suitble to liquid The device used for image display colour filter such as LCD panel, thereby completing the present invention.

The present invention is carried out based on above-mentioned opinion, is provided a kind of photosensitive composite, is contained with the following general formula (1) compound of the substituent group represented by.

[changing 1]

(in formula, R¹And R²It separately indicates hydrogen atom, halogen atom, cyano, hydroxyl, nitro, carboxyl, also have sometimes Alkyl that the carbon atom number of substituted base is 1~40, the aryl that also carbon atom number with substituent group is 6~20 sometimes, sometimes Aryl alkyl that also carbon atom number with substituent group is 7~20, also the carbon atom number with substituent group is 2~20 to contain sometimes Heterocyclic group or trialkylsilkl,

R¹And R²Methylene in represented alkyl or aryl alkyl will be also selected from-O- ,-S- ,-CO- ,-O- sometimes CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO- O- ,-NR '-,-S-S- or-SO₂In group combined under the conditions of oxygen atom is non-conterminous obtained from group replace, R ' tables Show the alkyl that hydrogen atom or carbon atom number are 1~8,

J indicates 1~3 number,

* refer in the parts * and adjacent group bonding.)

Specific implementation mode

Hereinafter, based on preferred embodiment, the present invention is described in detail.

The photosensitive composite of the present invention contains the compound with the substituent group represented by above-mentioned logical formula (I).

In compound with the substituent group represented by above-mentioned logical formula (I), compound represented by the following general formula (I-A) by In especially heat resistance, high and exhaust is few, it is advantageous to.

[changing 2]

(in formula, n indicates 1~10 integer,

X¹Indicate the conjugated group of n valences,

R¹、R²And j is identical as above-mentioned logical formula (I).)

As R¹And R²Represented halogen atom can enumerate fluorine, chlorine, bromine, iodine,

As R¹And R²Represented carbon atom number be 1~20 alkyl, can enumerate methyl, ethyl, propyl, isopropyl, Butyl, sec-butyl, tertiary butyl, isobutyl group, amyl, isopentyl, tertiary pentyl, cyclopenta, hexyl, 2- hexyls, 3- hexyls, hexamethylene Base, 4- methylcyclohexyls, heptyl, 2- heptyl, 3- heptyl, different heptyl, tertiary heptyl, 1- octyls, iso-octyl, t-octyl, adamantane Base etc.,

As R¹And R²The aryl that represented carbon atom number is 6~20, can enumerate phenyl, naphthalene, anthryl, phenanthryl, fluorenes Base, indenyl, 2- aminomethyl phenyls, 3- aminomethyl phenyls, 4- aminomethyl phenyls, 4- ethenylphenyls, 3- isopropyl phenyls, 4- cumenes Base, 4- butyl phenyls, 4- isobutyl phenenyls, 4- tert-butyl-phenyls, 4- hexyls phenyl, 4- cyclohexyl phenyls, 4- octyl phenyls, 4- (2- ethylhexyls) phenyl, 4- stearyls phenyl, 2,3- 3,5-dimethylphenyls, 2,4- 3,5-dimethylphenyls, 2,5- 3,5-dimethylphenyls, 2, 6- 3,5-dimethylphenyls, 3,4- 3,5-dimethylphenyls, 3,5- 3,5-dimethylphenyls, 2,4- di-tert-butyl-phenyls, 2,5- di-tert-butyl-phenyls, 2,6- di-tert-butyl-phenyls, 2,4- di-tert-pentyl-phenyls, 2,5- di-tert-pentyl-phenyls, bis- t-octyl phenyl of 2,5-, 2,4- bis- are withered Base phenyl, 4- cyclohexyl phenyls, (1,1 '-biphenyl) -4- bases, 2,4,5- trimethylphenyls, ferrocenyl etc.,

As R¹And R²The aryl alkyl that represented carbon atom number is 7~20, can enumerate benzyl, 1- methyl-1s-phenyl Ethyl, 1- naphthyl methyls, 9- anthrylmethyls, 9- fluorenyls, 3- phenyl propyls, methyl -2- phenyl-propane -2- bases, diphenyl methyl, Trityl group, phenethyl, styryl, cinnamyl etc.,

As R¹And R²Represented carbon atom number be 2~20 contain heterocyclic group, can enumerate by pyridine ring, pyrimidine ring, Pyridazine ring, piperidine ring, pyranoid ring, pyrazoline ring, triazine ring, pyrrolin ring, quinoline ring, isoquinolin ring, imidazoline ring, benzo miaow Oxazoline ring, triazoline ring, furan nucleus, benzofuran ring, Thiadiazoline ring, thiazoline ring, benzothiazoline ring, thiphene ring, Evil Oxazoline ring, benzoxazole quinoline ring, isothiazoline ring, isoxazoline rings, indole ring, pyrrolidine ring, piperidones ring, dioxane rings etc. Group obtained from heterocycle is combined with methene chain,

As R¹And R²Represented trialkylsilkl can enumerate trimethyl silane, triethylsilane, ethyl two The silicyl that methyl-monosilane etc. is replaced by the alkyl (3 alkyl are identical or different) that carbon atom number is 1~6.

The alkyl for being 1~8 as the carbon atom number represented by R ', can enumerate R¹Satisfaction in represented abovementioned alkyl The alkyl of defined carbon atom number.

As to R¹And R²Aryl that alkyl that represented carbon atom number is 1~40, carbon atom number are 6~20, carbon atom The substituent group replaced containing heterocyclic group that the aryl alkyl or carbon atom number that number is 7~20 are 2~20, can enumerate ethylene The ethylenically unsaturated groups such as base, allyl, acrylic, methacrylic acid group；The halogen atoms such as fluorine, chlorine, bromine, iodine；Acetyl Base, 2- chloracetyls, propiono, caprylyl, acryloyl group, methylacryloyl, phenylcarbonyl group (benzoyl), O-phthalic Acyl group, 4- trifluoromethylbenzoyl, valeryl, salicyl, oxalyl group, stearyl, methoxycarbonyl, ethyoxyl carbonyl The acyl groups such as base, tert-butoxycarbonyl, n-octadecane Epoxide carbonyl, carbamoyl；The acyl-oxygens such as acetoxyl group, benzoyloxy Base；Amino, ethylamino, dimethylamino, diethylamino, butylamino, clopentylamino, 2- ethylhexylaminos, ten Dialkyl amido, anilino-, chlorphenylamino, toluene amido, anisidino, N- metlyl-phenylamines base, diphenyl amino, naphthalene Amino, 2- pyridinylaminos, methyloxycarbonylamino, phenoxycarbonylamino, acetyl-amino, benzoyl-amido, formyl Base amino, valeryl amino, lauroyl amino, carbamoylamino, N, N- Dimethylaminocarbonyls amino, N, N- bis- Ethylaminocarbonylamino, morpholino carbonyl amino, methyloxycarbonylamino, ethoxycarbonylamino group, tert-butoxycarbonyl ammonia Base, n-octadecane Epoxide carbonyl amino, N- methyl methoxycarbonylaminos, phenoxycarbonylamino, sulphamoylamino, N, N- dimethylaminosulfonylaminos, Methylsulfonylamino, butyl sulfuryl amino, phenyl sulfonyl amino etc. replace ammonia Base；Sulfoamido, sulfonyl, carboxyl, cyano, sulfo group, hydroxyl, nitro, sulfydryl, imide, carbamoyl, sulfonamide The salt etc. of base, phosphonic acid base, phosphate or carboxyl, sulfo group, phosphonic acid base, phosphate.

As R¹And R², the aryl that alkyl that hydrogen atom, carbon atom number are 1~8, carbon atom number are 6~12 is due to exhaust It is few, it is advantageous to.R¹And R²Appointing for hydrogen atom or in alkyl, particularly tertiary butyl that the carbon atom number with branch is 1~8 The compound of one is few due to being vented, so further preferably.

In above-mentioned general formula (I-A), X¹Indicate n valences combination base, specifically, for example indicate Direct Bonding, hydrogen atom, Nitrogen-atoms, oxygen atom, sulphur atom, phosphorus atoms, the group represented by following (I-a) or (I-b) ,-CO- ,-NH-CO- ,-CO- NH-、-NR³-、-OR³、-SR³、-NR³R⁴Or with the also carbon atom number with substituent group sometimes with the equal number of valence mumbers of n For 1~120 aliphatic alkyl, sometimes also the carbon atom number with substituent group be 6~35 containing fragrant cyclic hydrocarbon radical or sometimes Also the carbon atom number with substituent group is 2~35 containing heterocyclic group, R³And R⁴It indicates hydrogen atom, also there is substituent group sometimes Aliphatic alkyl that carbon atom number is 1~35, sometimes also the carbon atom number with substituent group be 6~35 containing fragrant cyclic hydrocarbon radical or Sometimes the heterocyclic group that contains that also carbon atom number with substituent group is 2~35, aliphatic alkyl contain fragrant cyclic hydrocarbon radical and contain heterocycle Group sometimes also by selected from carbon-to-carbon double bond ,-O- ,-S- ,-CO- ,-O-CO- ,-CO-O- ,-O-CO-O- ,-S-CO- ,-CO-S- ,- S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-O-CO-NH-、-NR’-、-S-S-、-SO₂Or nitrogen is former Group substitution in son.

Wherein, in X¹In the case of the combination base represented by nitrogen-atoms, phosphorus atoms or following (I-a) or (I-b), n It is 3, in X¹For oxygen atom or sulphur atom ,-CO- ,-NH-CO- ,-CO-NH- or-NR³In the case of, n 2, in X¹For hydrogen original Son ,-OR³、-SR³Or-NR³R⁴In the case of, n 1, X¹Sometimes ring is also formed together with phenyl ring.

[changing 3]

(* refers in the parts * and adjacent group bonding.)

Compound represented by above-mentioned general formula (I-A) has in X¹It is a specific that n is bonded on the combination base of represented n valences Group obtained from structure.The n group is same or different to each other.The value of n is 1~10, excellent from the viewpoint of low exhaust It is selected as 2~6.

As the X in above-mentioned general formula (I-A)¹It is represented, with the equal number of valence mumbers of n, sometimes also with substitution The aliphatic alkyl that the carbon atom number of base is 1~120 can enumerate such as methyl, second as the aliphatic alkyl that n is 1 valence Base, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tertiary butyl, isobutyl group, amyl, isopentyl, tertiary pentyl, cyclopenta, oneself Base, 2- hexyls, 3- hexyls, cyclohexyl, dicyclohexyl, 1- methylcyclohexyls, heptyl, 2- heptyl, 3- heptyl, different heptyl, tertiary heptan The alkyl such as base, n-octyl, iso-octyl, t-octyl, 2- ethylhexyls, nonyl, isononyl, decyl；Methyl oxygroup, ethyl oxygroup, Propyl oxygroup, isopropyl oxygroup, butyl oxygroup, sec-butyl oxygroup, tertiary butyl oxygroup, isobutyl group oxygroup, amyl oxygroup, isopentyl Oxygroup, tertiary pentyl oxygroup, hexyl oxygroup, cyclohexyl oxygroup, heptyl oxygroup, different heptyl oxygroup, tertiary heptyl oxygroup, n-octyl oxygen The alkoxies such as base, iso-octyl oxygroup, t-octyl oxygroup, 2- ethylhexyls oxygroup, nonyl oxygroup, decyl oxygroup；Methyl mercapto, second sulphur Base, rosickyite base, isopropyisulfanyl, butylthio, secondary butylthio, tertiary butylthio, isobutylthio, penta sulfenyl, isopentylthio, penta sulphur of uncle Base, own sulfenyl, cyclohexylthio, sulfenyl in heptan, different sulfenyl in heptan, tertiary sulfenyl in heptan, just pungent sulfenyl, different pungent sulfenyl, tertiary pungent sulfenyl, 2- ethyls The alkylthio groups such as own sulfenyl；Vinyl, 1- methyl ethylenes, 2- methyl ethylenes, 2- acrylic, 1- methyl -3- acrylic, 3- fourths It is alkenyl, 1- methyl -3- cyclobutenyls, isobutenyl, 3- pentenyls, 4- hexenyls, cyclohexenyl group, dicyclohexenyl, heptenyl, pungent The alkenyls such as alkenyl, decene base, 15 carbene bases, eicosylene base, tricosene base；And these groups are by aftermentioned substituent group Group obtained from substitution etc.,

As the aliphatic alkyl that n is divalent, methylene, ethylidene, propylidene, butylidene, butyl diyl etc. can be enumerated Alkylidene；Group obtained from the methene chain of above-mentioned alkylidene is replaced by-O- ,-S- ,-CO-O- ,-O-CO-；Ethylene glycol, third The residue of the glycol such as glycol, butanediol, pentanediol, hexylene glycol；Dithioglycol, dimercaptopropane, succinimide mercaptans, pentane disulfide thioalcohol, oneself The residue of two mercaptan such as two mercaptan；And these groups replaced by aftermentioned substituent group obtained from group etc.,

As the aliphatic alkyl that n is trivalent, such as propylidyne, 1, the alkylidene such as 1,3- butylidyne can be enumerated；And these Group obtained from group is replaced by aftermentioned substituent group.

As with the equal number of valence mumbers of n sometimes also the carbon atom number with substituent group be 6~35 containing fragrance Cyclic hydrocarbon radical can enumerate benzyl, phenethyl, diphenyl methyl, trityl group, benzene as the cyclic hydrocarbon radical containing fragrance that n is 1 valence The aryl alkyls such as vinyl, cinnamyl；The aryl such as phenyl, naphthalene；The aryloxy group such as phenoxy group, naphthoxy；Thiophenyl, naphthalene sulfenyl etc. Arylthio；And these groups replaced by aftermentioned substituent group obtained from group etc.,

As the cyclic hydrocarbon radical containing fragrance that n is divalent, the arlydene such as phenylene, naphthylene can be enumerated；Catechol, bis-phenol etc. The residue of two trifunctional phenols；Tetra- oxaspiros of 2,4,8,10- [5,5] hendecane etc.；And these groups are replaced by aftermentioned substituent group Obtained from group,

As the cyclic hydrocarbon radical containing fragrance that n is trivalent, phenyl -1,3 can be enumerated, 5- trimethylenes and these groups are aftermentioned Substituent group substitution obtained from group.

As with the equal number of valence mumbers of n sometimes also the carbon atom number with substituent group be 2~35 contain heterocycle Group contains heterocyclic group for 1 valence as n, can enumerate pyridyl group, pyrimidine radicals, pyridazinyl, piperidyl, pyranose, pyrazoles Base, triazine radical, pyrrole radicals, quinolyl, isoquinolyl, imidazole radicals, benzimidazolyl, triazolyl, furyl, furyl, benzo Furyl, thienyl, thiophenyl, aisaa benzothiophenyl, thiadiazolyl group, thiazolyl, benzothiazolyl, oxazolyls, benzoxazolyl, Isothiazolyl, isoxazolyl, indyl, 2-Pyrrolidone -1- bases, 2- piperidones -1- bases, bis- oxygroup imidazolidine -3- bases of 2,4-, 2,4- bis- Yang Ji oxazolidine -3- bases, benzotriazole base etc.；And these groups replaced by aftermentioned substituent group obtained from group Deng,

Contain heterocyclic group for divalent as n, can enumerate with pyridine ring, pyrimidine ring, piperidine ring, piperazine ring, triazine The group of ring, furan nucleus, thiphene ring, indole ring etc.；And these groups replaced by aftermentioned substituent group obtained from group,

Contain heterocyclic group for trivalent as n, the group with isocyanuric acid ring, the group with triazine ring can be enumerated； And these groups replaced by aftermentioned substituent group obtained from group.

As R³And R⁴The represented aliphatic alkyl that also carbon atom number with substituent group is 1~35 sometimes, can enumerate Go out above-mentioned X¹Represented aliphatic alkyl and the aliphatic alkyl and carbon as defined in the satisfaction in the combination of above-mentioned substituent group are former The group of subnumber,

As R³And R⁴Represented also has the cyclic hydrocarbon radicals containing fragrance and have that the carbon atom number of substituent group is 6~35 sometimes When also with substituent group carbon atom number be 2~35 contain heterocyclic group, above-mentioned X can be enumerated¹Represented carbon atom number is 6 ~35 containing fragrant cyclic hydrocarbon radical and carbon atom number be 2~35 containing heterocyclic group and by these groups and aftermentioned substituent group The group of carbon atom number as defined in satisfaction in group obtained from conjunction.

As substituent group, the ethylenic bonds such as vinyl, allyl, acrylic, methacrylic acid group unsaturation can be enumerated Group；The halogen atoms such as fluorine, chlorine, bromine, iodine；Acetyl group, 2- chloracetyls, propiono, caprylyl, acryloyl group, metering system Acyl group, phenylcarbonyl group (benzoyl), phthalyl, 4- trifluoromethylbenzoyl, valeryl, salicyl, grass Acyl group, stearyl, methoxycarbonyl, ethoxy carbonyl, tert-butoxycarbonyl, n-octadecane Epoxide carbonyl, carbamoyl Equal acyl groups；The acyloxy such as acetoxyl group, benzoyloxy；Amino, ethylamino, dimethylamino, diethylamino, butyl ammonia Base, clopentylamino, 2- ethylhexylaminos, dodecylamino, anilino-, chlorphenylamino, toluene amido, anisidine Base, N- metlyl-phenylamines base, diphenyl amino, naphthyl-amino, 2- pyridinylaminos, methyloxycarbonylamino, phenyloxycarbonyl ammonia Base, acetyl-amino, benzoyl-amido, Formylamino, valeryl amino, lauroyl amino, carbamoyl ammonia Base, N, N- Dimethylaminocarbonyls amino, N, N- diethylaminocarbonyls amino, morpholino carbonyl amino, methoxycarbonyl ammonia Base, ethoxycarbonylamino group, tertbutyloxycarbonylamino, n-octadecane Epoxide carbonyl amino, N- methyl-methoxycarbonyl ammonia Base, phenoxycarbonylamino, sulphamoylamino, N, N- dimethylaminosulfonylaminos, Methylsulfonylamino, butyl sulphur The substituted-aminos such as acyl amino, phenyl sulfonyl amino；Sulfoamido, sulfonyl, carboxyl, cyano, sulfo group, hydroxyl, nitro, mercapto The salt etc. of base, imide, carbamoyl, sulfoamido, phosphonic acid base, phosphate or carboxyl, sulfo group, phosphonic acid base, phosphate, These groups are also further substituted sometimes.In addition, carboxyl and sulfo group go back forming salt sometimes.

In above-mentioned general formula (I-A), when n is 2~6, X¹It can also be indicated as the following general formula (1)~(5) respectively.

[changing 4]

*-Z¹-Y¹-Z²-* (1)

(in above-mentioned general formula (1), Y¹Indicate singly-bound ,-CR⁵R⁶-、-NR⁷, divalent carbon atom number be 1~35 aliphatic hydrocarbon The aromatic hydrocarbyl or carbon atom number that base, carbon atom number are 6~35 be 2~35 containing heterocyclic group or following (1-1)~ Any substituent group represented by (1-3),

The aliphatic alkyl is sometimes also by-O- ,-S- ,-CO- ,-COO- ,-OCO- ,-NH- ,-SO₂,-CONH- or- NHCO- replaces in conjunction with base obtained from combining them in such a way that oxygen atom is non-conterminous,

Z¹And Z²Separately indicate Direct Bonding ,-O- ,-S-,>CO、-CO-O-、-O-CO-、-SO₂-、-SS-、- SO-、-NR⁷Or-PR⁷,

R⁵、R⁶And R⁷Separately indicate hydrogen atom, the fat that also carbon atom number with substituent group is 1~35 sometimes Race's alkyl, sometimes also the carbon atom number with substituent group be 6~35 aromatic hydrocarbyl or sometimes also with substituent group carbon original Subnumber be 2~35 contain heterocyclic group,

* refer in the parts * and adjacent group bonding.)

[changing 5]

(in above-mentioned formula, R⁸Indicate that hydrogen atom or the sometimes phenyl also with substituent group or carbon atom number are 3~10 Naphthenic base,

R⁹Indicate that alkoxy, carbon atom number that alkyl, carbon atom number that carbon atom number is 1~10 are 1~10 are 2~10 Alkenyl or halogen atom, abovementioned alkyl, alkoxy and alkenyl also have substituent group sometimes,

The integer that f is 0~5,

* refer in the parts * and adjacent group bonding.)

[changing 6]

(* refers in the parts * and adjacent group bonding.)

[changing 7]

(in above-mentioned formula, R¹⁰And R¹¹Separately indicate the alkane that also carbon atom number with substituent group is 1~10 sometimes Base, the aryl that also carbon atom number with substituent group is 6~20 sometimes, also the carbon atom number with substituent group is 6~20 sometimes Aryloxy group, the arylthio that also carbon atom number with substituent group is 6~20 sometimes, the sometimes also carbon atom number with substituent group For 6~20 aromatic yl alkenyl, the aryl alkyl that also carbon atom number with substituent group is 7~20 sometimes, sometimes also with taking The carbon atom number of Dai Ji be 2~20 contain heterocyclic group or halogen atom,

Methylene in the alkyl and aryl alkyl is also replaced by unsaturated bond ,-O- or-S- sometimes,

R¹⁰Sometimes also pass through adjacent R¹⁰Ring is formed each other,

P indicates 0~4 number,

Q indicates 0~8 number,

G indicates 0~4 number,

H indicates 0~4 number,

The number of g and h adds up to 2~4,

* refer in the parts * and adjacent group bonding.)

[changing 8]

(in above-mentioned general formula (2), Y¹¹Indicate that aliphatic alkyl, carbon atom number that the carbon atom number of trivalent is 3~35 are 3~35 Alicyclic alkyl, carbon atom number be 6~35 aromatic hydrocarbyl or carbon atom number be 2~35 contain heterocyclic group,

Z¹、Z²And Z³Separately indicate Direct Bonding ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-SO₂-、- SS-、-SO-、-NR¹²Or-PR¹²,

R¹²It indicates hydrogen atom, the aliphatic alkyl that also carbon atom number with substituent group is 1~35 sometimes, also have sometimes The aromatic hydrocarbyl or also the carbon atom number with substituent group is 2~35 containing miscellaneous sometimes that the carbon atom number of substituent group is 6~35 Cyclic group,

Aliphatic alkyl is sometimes also by carbon-to-carbon double bond ,-O- ,-S- ,-CO- ,-COO- ,-OCO- ,-NH- ,-SO₂-、- CONH- or-NHCO- replaces in conjunction with base obtained from combining them in such a way that oxygen atom is non-conterminous,

* refer in the parts * and adjacent group bonding.)

[changing 9]

(in above-mentioned general formula (3), Y¹²Indicate the aliphatic alkyl, carbon atom that the carbon atom number of carbon atom or 4 valences is 1~35 Number for 6~35 aromatic hydrocarbyl or carbon atom number be 2~35 contain heterocyclic group,

The aliphatic alkyl is sometimes also by carbon-to-carbon double bond ,-O- ,-S- ,-CO- ,-COO- ,-OCO- ,-NH- ,-SO₂-、- CONH- or-NHCO- replaces in conjunction with base obtained from combining them in such a way that oxygen atom is non-conterminous,

Z¹~Z⁴It is and the Z in above-mentioned general formula (2) separately¹~Z³The group of the identical range of represented group,

* refer in the parts * and adjacent group bonding.)

[changing 10]

(in above-mentioned general formula (4), Y¹³Indicate that aliphatic alkyl, carbon atom number that the carbon atom number of 5 valences is 2~35 are 6~20 Aromatic hydrocarbyl or carbon atom number be 2~20 contain heterocyclic group,

Z¹~Z⁵It is and the Z in above-mentioned general formula (2) separately¹~Z³The group of the identical range of represented group,

* refer in the parts * and adjacent group bonding.)

[changing 11]

(in above-mentioned general formula (5), Y¹⁴Indicate that aliphatic alkyl, carbon atom number that the carbon atom number of 6 valences is 2~35 are 6~35 Aromatic hydrocarbyl or carbon atom number be 2~35 contain heterocyclic group,

Z¹~Z⁶It is and the Z in above-mentioned general formula (2) separately¹~Z³The group of the identical range of represented group,

* refer in the parts * and adjacent group bonding.)

In above-mentioned general formula (1), as R⁵、R⁶And R⁷The represented carbon atom number of substituent group that also has sometimes is 1~35 Aliphatic alkyl, can enumerate as the X in above-mentioned general formula (I-A)¹1 valence illustrated by the combination base of represented n valences Aliphatic alkyl and these groups are by as the X indicated in above-mentioned general formula (I-A)¹The group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in group obtained from group substitution illustrated by substituent group,

As R⁵、R⁶And R⁷The represented cyclic hydrocarbon radical containing fragrance that also carbon atom number with substituent group is 6~35 sometimes, It can enumerate as the X in above-mentioned general formula (I-A)¹The cyclic hydrocarbon radical containing fragrance of 1 valence illustrated by the combination base of represented n valences, And these groups are by as the X indicated in above-mentioned general formula (I-A)¹The substituent group institute example of the group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in group obtained from the group substitution shown,

As R⁵、R⁶And R⁷Represented also has the carbon atom number of substituent group for 2~35 containing heterocyclic group sometimes, can It enumerates as the X in above-mentioned general formula (I-A)¹1 valence illustrated by the combination base of represented n valences containing heterocyclic group and this A little groups are by as the X indicated in above-mentioned general formula (I-A)¹Base illustrated by the substituent group of the group of the bonding of represented n valences The group etc. of carbon atom number as defined in satisfaction in group obtained from group's substitution.

In addition, as Y in above-mentioned general formula (1)¹The aliphatic alkyl that the carbon atom number of represented divalent is 1~35, can arrange It enumerates as the X in above-mentioned general formula (I-A)¹The aliphatic alkyl of divalent illustrated by the combination base of represented n valences and these Group is by as the X indicated in above-mentioned general formula (I-A)¹Base illustrated by the substituent group of the group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in group obtained from group's substitution,

As Y¹The cyclic hydrocarbon radical containing fragrance that the carbon atom number of represented divalent is 6~35, can enumerate as above-mentioned general formula (I-A) X in¹The cyclic hydrocarbon radical containing fragrance of divalent illustrated by the combination base of represented n valences and these groups are by as expression X in above-mentioned general formula (I-A)¹Obtained from group substitution illustrated by the substituent group of the group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in group,

As Y¹The carbon atom number of represented divalent, containing heterocyclic group, can be enumerated as above-mentioned general formula for 2~35 (I-A) X in¹The cyclic hydrocarbon radical containing fragrance of divalent illustrated by the combination base of represented n valences and these groups are by as expression X in above-mentioned general formula (I-A)¹Obtained from group substitution illustrated by the substituent group of the group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in group.

In substituent group represented by above-mentioned (1-1), as R⁸The naphthenic base that represented carbon atom number is 3~10, can Cyclopropyl, cyclobutyl, cyclopenta, suberyl, cyclooctyl etc. are enumerated,

As R⁹The alkyl that represented carbon atom number is 1~10, can enumerate as R¹And R²Represented carbon atom number The group etc. of carbon atom number as defined in satisfaction in group illustrated by alkyl for 1~40,

As R⁹The alkoxy that represented carbon atom number is 1~10, can enumerate methyl oxygroup, ethyl oxygroup, propyl Oxygroup, isopropyl oxygroup, butyl oxygroup, sec-butyl oxygroup, tertiary butyl oxygroup, isobutyl group oxygroup, amyl oxygroup, isopentyl oxygen Base, tertiary pentyl oxygroup, hexyl oxygroup, cyclohexyl oxygroup, heptyl oxygroup, different heptyl oxygroup, tertiary heptyl oxygroup, n-octyl oxygroup, Iso-octyl oxygroup, t-octyl oxygroup, 2- ethylhexyls oxygroup, nonyl oxygroup, decyl oxygroup etc.,

Phenyl, naphthenic base, alkyl, alkoxy and alkenyl substituent group with as the X in above-mentioned general formula (I-A)¹Institute's table Group is same illustrated by the substituent group of the combination base of the n valences shown.

In group represented by above-mentioned (1-3), as R¹⁰And R¹¹The represented carbon atom also sometimes with substituent group Number is 1~10 alkyl, can be enumerated as R¹And R²In group illustrated by the alkyl that represented carbon atom number is 1~40 Satisfaction as defined in carbon atom number alkyl etc.,

As R¹⁰And R¹¹The represented aryl that also carbon atom number with substituent group is 6~20 sometimes, can enumerate work For R¹And R²Group etc. illustrated by the aryl that represented carbon atom number is 6~20,

As R¹⁰And R¹¹The represented aryloxy group that also carbon atom number with substituent group is 6~20 sometimes, can enumerate Phenoxy group, naphthoxy, 2- methylphenoxies, 3- methylphenoxies, 4- methylphenoxies, 4- ethenylphenyls oxygroup, 3- isopropyls Phenoxyl, 4- cumenes oxygroup, 4- butyl phenoxies, 4- tert-butyl benzenes oxygroup, 4- hexyls phenoxy group, 4- cyclohexyl benzene oxygen Base, 4- Octylphenoxies, 4- (2- ethylhexyls) phenoxy group, 2,3- dimethyl phenoxies, 2,4- dimethyl phenoxies, 2,5- bis- Methylphenoxy, 2,6- dimethyl phenoxies, 3,4- dimethyl phenoxies, 3,5- dimethyl phenoxies, 2,4- di-tert-butyls Oxygroup, 2,5- di-t-butyls phenoxy group, 2,6- di-t-butyls phenoxy group, bis- tert-amyl benzene oxygroups of 2,4-, 2,5- tert-amyl benzene oxygen The groups such as base, 4- cyclohexyl benzenes oxygroup, 2,4,5- trimethylbenzene oxygroups, ferrocenyl oxygroup,

As R¹⁰And R¹¹The represented arylthio that also carbon atom number with substituent group is 6~20 sometimes, can enumerate The oxygen atom of the aryloxy group that also carbon atom number with substituent group is 6~20 above-mentioned sometimes is substituted by base obtained from sulphur atom Group etc.,

As R¹⁰And R¹¹The represented aromatic yl alkenyl that also carbon atom number with substituent group is 8~20 sometimes, can arrange It enumerates oxygen atom vinyl, allyl, the 1- of the aryloxy group that also carbon atom number with substituent group is 6~20 above-mentioned sometimes Base obtained from the substitution of the alkenyls such as acrylic, isopropenyl, 2- cyclobutenyls, 1,3- butadienyls, 2- pentenyls, 2- octenyls Group etc.,

As R¹⁰And R¹¹The represented aryl alkyl that also carbon atom number with substituent group is 7~20 sometimes, can enumerate Go out as R¹And R²Group etc. illustrated by the aryl alkyl that represented carbon atom number is 7~20,

As R¹⁰And R¹¹Represented sometimes also there is the carbon atom number of substituent group, containing heterocyclic group, can be arranged for 2~20 It enumerates as R¹And R²Represented carbon atom number is 2~20 containing group etc. illustrated by heterocyclic group.

As the Y in above-mentioned general formula (2)¹¹The aliphatic alkyl that the carbon atom number of represented trivalent is 1~35, can enumerate Go out as the X in above-mentioned general formula (I-A)¹The aliphatic alkyl and these bases of trivalent illustrated by the combination base of represented n valences Group is by as the X in above-mentioned general formula (I-A)¹Group substitution illustrated by the substituent group in conjunction with base of represented n valences obtains Group in satisfaction as defined in carbon atom number group etc. by Z¹、Z²And Z³The group etc. of substituted trivalent,

As the Y in above-mentioned general formula (2)¹¹The alicyclic alkyl that the carbon atom number of represented trivalent is 3~35, can enumerate Go out by cyclopenta, cyclohexyl, suberyl, cyclooctyl, cyclodecyl, 1- adamantyls, 2- adamantyls, positive adamantyl, 2- first Adamantyl, norborny, different norborny, perhydro naphthalene, perhydro anthryl, two rings [1.1.0] butyl, two rings [1.1.1] Amyl, two rings [2.1.0] amyl, two rings [3.1.0] hexyl, two rings [2.1.1] hexyl, two rings [2.2.0] hexyl, two rings [4.1.0] heptyl, two rings [3.2.0] heptyl, two rings [3.1.1] heptyl, two rings [2.2.1] heptyl, two rings [5.1.0] octyl, Two rings [4.2.0] octyl, two rings [4.1.1] octyl, two rings [3.3.0] octyl, two rings [3.2.1] octyl, two rings [2.2.2] are pungent Base, spiral shell (4,4) nonyl, spiral shell (4,5) decyl, decahydronaphthalenes, tricyclodecyl, tetracyclododecyl group, cedrol, cyclo-dodecyl etc. The group etc. of trivalent derived from group,

As Y¹¹The cyclic hydrocarbon radical containing fragrance that the carbon atom number of represented trivalent is 6~35, can enumerate as above-mentioned general formula (I-A) X in¹The cyclic hydrocarbon radical containing fragrance of trivalent illustrated by the combination base of represented n valences and these groups are by as above-mentioned X in general formula (I-A)¹Expiring in group obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in foot,

As Y¹¹The carbon atom number of represented trivalent, containing heterocyclic group, can be enumerated as above-mentioned general formula for 2~35 (I-A) X in¹Trivalent illustrated by the combination base of represented n valences is led to containing heterocyclic group and these groups as above-mentioned X in formula (I-A)¹Satisfaction in group obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of defined carbon atom number.

In addition, as R¹²The aliphatic alkyl that also carbon atom number with substituent group is 1~35 represented sometimes, sometimes The aromatic hydrocarbyl and also the carbon atom number with substituent group is 2~35 sometimes that also the carbon atom number with substituent group is 6~35 Contain heterocyclic group, the R in above-mentioned general formula (1) can be enumerated respectively⁵、R⁶And R⁷Explanation in illustrated by aliphatic alkyl, Containing fragrant cyclic hydrocarbon radical, contain heterocyclic group.

As Y in above-mentioned general formula (3)¹²The aliphatic alkyl that the carbon atom number of 4 represented valences is 1~35, can enumerate As the X in above-mentioned general formula (I-A)¹The aliphatic alkyl of 1 valence~trivalent illustrated by the combination base of represented n valences and by this A little groups are by as the X in above-mentioned general formula (I-A)¹Illustrated by the substituent group in conjunction with base of represented n valences group substitution and The group etc. of carbon atom number as defined in satisfaction in the group of 4 valences derived from obtained group,

As Y¹²The cyclic hydrocarbon radical containing fragrance that the carbon atom number of 4 represented valences is 6~35, can enumerate as above-mentioned general formula (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences containing fragrant cyclic hydrocarbon radical and made by these groups For the X in above-mentioned general formula (I-A)¹Group obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of derivative 4 valence,

As Y¹²The carbon atom number of 4 represented valences, containing heterocyclic group, can be enumerated as above-mentioned general formula for 2~35 (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences contains heterocyclic group and by these groups by conduct X in above-mentioned general formula (I-A)¹Group spreads out obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of 4 raw valences.

As the Y in above-mentioned general formula (4)¹³The aliphatic alkyl that the carbon atom number of 5 represented valences is 2~35, can enumerate Go out as the X in above-mentioned general formula (I-A)¹The aliphatic alkyl of 1 valence~trivalent illustrated by the combination base of represented n valences and by These groups are by as the X in above-mentioned general formula (I-A)¹Group illustrated by the substituent group of the combination base of represented n valences replaces Obtained from 5 valences derived from group group in satisfaction as defined in carbon atom number group etc.,

As Y¹⁴The cyclic hydrocarbon radical containing fragrance that the carbon atom number of 5 represented valences is 6~35, can enumerate as above-mentioned general formula (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences containing fragrant cyclic hydrocarbon radical and made by these groups For the X in above-mentioned general formula (I-A)¹Group obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of derivative 5 valence,

As Y¹⁴The carbon atom number of 5 represented valences, containing heterocyclic group, can be enumerated as above-mentioned general formula for 2~35 (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences contains heterocyclic group and by these groups by conduct X in above-mentioned general formula (I-A)¹Group spreads out obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of 5 raw valences.

As the Y in above-mentioned general formula (5)¹⁴The aliphatic alkyl that the carbon atom number of 6 represented valences is 2~35, can enumerate Go out as the X in above-mentioned general formula (I-A)¹The aliphatic alkyl of 1 valence~trivalent illustrated by the combination base of represented n valences and by These groups are by as the X in above-mentioned general formula (I-A)¹Group illustrated by the substituent group of the combination base of represented n valences replaces Obtained from 6 valences derived from group group in satisfaction as defined in carbon atom number group etc.,

As Y¹⁴The cyclic hydrocarbon radical containing fragrance that the carbon atom number of 6 represented valences is 6~35, can enumerate as above-mentioned general formula (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences containing fragrant cyclic hydrocarbon radical and made by these groups For the X in above-mentioned general formula (I-A)¹Group obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of derivative 6 valence,

As Y¹⁴The carbon atom number of 6 represented valences, containing heterocyclic group, can be enumerated as above-mentioned general formula for 2~35 (I-A) X in¹1 valence~trivalent illustrated by the combination base of represented n valences contains heterocyclic group and by these groups by conduct X in above-mentioned general formula (I-A)¹Group spreads out obtained from group substitution illustrated by the substituent group of the combination base of represented n valences The group etc. of carbon atom number as defined in satisfaction in the group of 6 raw valences.

In compound represented by above-mentioned general formula (I-A), the compound represented by the following general formula (II-1)~(II-3) Since heat resistance is got higher, it is advantageous to.

[changing 12]

(in formula, R⁸²、R⁸³And R⁸⁴Separately indicate hydrogen atom, halogen atom, cyano, hydroxyl, nitro, carboxyl or Sometimes it is 7~20 also to have aryl, carbon atom number that alkyl, carbon atom number that the carbon atom number of substituent group is 1~40 are 6~20 Aryl alkyl or carbon atom number be 2~20 contain heterocyclic group, R¹And R²It is identical as above-mentioned logical formula (I).)

[changing 13]

(in formula, r=2~6, X²It is the group represented by above-mentioned general formula (1) in r=2, is above-mentioned general formula in r=3 (2) group represented by is the group represented by above-mentioned general formula (3) in r=4, is above-mentioned general formula (4) in r=5, in r= It is above-mentioned general formula (5), R when 6⁹²And R⁹³Separately indicate hydrogen atom, halogen atom, cyano, hydroxyl, nitro, carboxyl or Sometimes it is 7~20 also to have aryl, carbon atom number that alkyl, carbon atom number that the carbon atom number of substituent group is 1~40 are 6~20 Aryl alkyl or carbon atom number be 2~20 contain heterocyclic group, R¹And R²It is identical as above-mentioned logical formula (I).)

[changing 14]

(in formula, R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸Separately indicate hydrogen atom, halogen atom, cyanogen The virtue that base, hydroxyl, nitro, carboxyl, the alkyl that also carbon atom number with substituent group is 1~40 sometimes, carbon atom number are 6~20 The aryl alkyl or carbon atom number that base, carbon atom number are 7~20 are 2~20 containing heterocyclic group, Y¹、Z¹And Z²With above-mentioned general formula (1) identical.)

As the R in above-mentioned general formula (II-1)⁸²、R⁸³And R⁸⁴Represented halogen atom, the sometimes also carbon with substituent group Aryl alkyl that aryl that alkyl that atomicity is 1~40, carbon atom number are 6~20, carbon atom number are 7~20, carbon atom number For 2~20 containing heterocyclic group, the R in above-mentioned logical formula (I) can be enumerated¹And R²Explanation in illustrated by group.

As the R in above-mentioned general formula (II-2)⁹²And R⁹³Represented halogen atom, also the carbon with substituent group is former sometimes Aryl alkyl that aryl that alkyl that subnumber is 1~40, carbon atom number are 6~20, carbon atom number are 7~20, carbon atom number 2 ~20 contain heterocyclic group, the R in above-mentioned logical formula (I) can be enumerated¹And R²Explanation in illustrated by group.

As the R in above-mentioned general formula (II-3)²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸Represented halogen is former Son also has the aryl that alkyl, carbon atom number that the carbon atom number of substituent group is 1~40 are 6~20, carbon atom number 7 sometimes ~20 aryl alkyl, carbon atom number are 2~20 to contain heterocyclic group, can enumerate the R in above-mentioned logical formula (I)¹And R²Say Group illustrated by bright.

In compound represented by above-mentioned general formula (II-1),

It is preferred that R¹For the carbon atom number with branch be 1~8 alkyl, particularly tertiary butyl, R²For hydrogen atom；It is preferred that R⁸²、R⁸³And R⁸⁴Be separately hydrogen atom, carbon atom number be 1~20 alkyl, carbon atom number be 6~10 aryl, carbon it is former Aryl alkyl that subnumber is 7~12, carbon atom number are 1~10 to contain heterocyclic group, particularly R⁸²、R⁸³And R⁸⁴Any one of For carbon atom number be 1~4 alkyl or carbon atom number be 1~10 contain heterocyclic group.

In compound represented by above-mentioned general formula (II-2),

It is preferred that R¹For the carbon atom number with branch be 1~8 alkyl, particularly tertiary butyl, R²For hydrogen atom；It is preferred that R⁹² And R⁹³Be separately hydrogen atom, carbon atom number be 1~20 alkyl, carbon atom number be 6~10 aryl, carbon atom number be 7~12 aryl alkyl, carbon atom number are 1~10 to contain heterocyclic group, particularly R⁹²Or R⁹³The alkane for being 1~4 for carbon atom number Base or carbon atom number are 1~10 containing heterocyclic group.

In X²In the case of above-mentioned general formula (1), preferably Y¹⁰For sulphur atom, carbon atom number be 1~20 alkylidene, carbon The divalent for being 2~21 containing fragrant cyclic hydrocarbon radical, carbon atom number for the divalent that atomicity is 6~25 contains heterocyclic group, by 2,4,8,10- The group of divalent, particularly carbon atom number are 1~15 derived from four oxaspiros [5,5] hendecane alkylidene, carbon atom number 6 The group containing fragrant cyclic hydrocarbon radical, the divalent derived from 2,4,8,10- tetra- oxaspiro [5,5] hendecanes of~15 divalent,

It is preferred that Z¹And Z²For Direct Bonding ,-CO-O- ,-O-CO- or can also be 1~20 with the carbon atom number of substituent group Aliphatic alkyl, carbon atom number be 6~10 aromatic hydrocarbyl, particularly can also be 1 with the carbon atom number of substituent group ~8 aliphatic alkyl.

In X²In the case of above-mentioned general formula (2), preferably Y¹¹For be 1~20 by carbon atom number alkyl, carbon atom number For 6~10 aryl, carbon atom number be 7~12 aryl alkyl or carbon atom number be 1~10 containing trivalent derived from heterocyclic group Group, particularly be 1~8 by carbon atom number alkyl, carbon atom number be 6~9 aryl or carbon atom number be 1~6 to contain The group of trivalent derived from heterocyclic group,

It is preferred that Z¹、Z²And Z³With Z¹And Z²Equally,

In X²In the case of above-mentioned general formula (3), Y¹²It is preferred that with as preferred Y¹¹The group pair being enumerated above out The group for 4 valences answered,

It is preferred that Z¹~Z⁴With Z¹And Z²Equally,

In X²In the case of above-mentioned general formula (4), Y¹³It is preferred that with as preferred Y¹¹The group pair being enumerated above out The group for 5 valences answered,

It is preferred that Z¹~Z⁵With Z¹And Z²Equally,

In X²In the case of above-mentioned general formula (5), Y¹⁴It is preferred that with as preferred Y¹¹The group pair being enumerated above out The group for 6 valences answered,

It is preferred that Z¹~Z⁶With Z¹And Z²Equally.

As the preferred compound in the compound represented by above-mentioned logical formula (I), following [changing 14]~[changes can be enumerated 15] compound shown in, but the present invention is not restricted to these compounds.

[changing 15]

[changing 16]

The manufacturing method of compound with the substituent group represented by above-mentioned logical formula (I) is not particularly limited, such as can be with Make special by Japanese Unexamined Patent Application 57-111375, Japanese Unexamined Patent Publication 3-173843, Japanese Unexamined Patent Publication 6-128195, Japan Open flat No. 7-206771, Japanese Unexamined Patent Publication 7-252191, Japanese Unexamined Patent Application Publication 2004-501128 each bulletin described in method and The phenol system compound of manufacture and halogenated allyl compound etc., which are reacted, to be obtained.

Compound with the substituent group represented by above-mentioned logical formula (I) is in the photosensitive composite of the present invention, Ke Yizuo It is used for latency additive.

Above-mentioned so-called latency additive is in room temperature or 150 DEG C or less, such as 150 DEG C of prebake processes below To be nonactive, protected by heating at 100~250 DEG C or being heated at 80~200 DEG C in the presence of acid/base catalyst Base is detached from, to become active additive.

In the photosensitive composite of the present invention, as latency additive with taking represented by above-mentioned logical formula (I) The content of the compound of Dai Ji preferably 0.001~20 mass % in the solid constituent of the composition of the present invention, more preferably 0.005~5 mass %.

The photosensitive composite of the present invention is the composition that property changes by light irradiates, relative to chemical reaction Become have positive-workingresist in soluble composition, becomes have negative resist in insoluble composition relative to chemical reaction. The photosensitive composite of the present invention is in addition to anti-as latency comprising the compound with the substituent group represented by above-mentioned logical formula (I) Also include that polymerizable compound with ethylenic bond unsaturated bond and optical free radical with acid value polymerize initiation other than oxidant Agent is as essential component.

As the polymerizable compound with ethylenic bond unsaturated bond with acid value, (methyl) propylene can be enumerated Acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, carbic acid, crotonic acid, iso-crotonic acid, vinyl Acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, mono succinate [2- (methyl) acryloyl-oxyethyl] ester, adjacent benzene Diformate mono [2- (methyl) acryloyl-oxyethyl] ester, ω-carboxy-polycaprolactone list (methyl) acrylate etc. are in two ends List (methyl) acrylate of polymer with carboxyl and hydroxyl, (methyl) Hydroxyethyl Acrylate malate, (first Base) hydroxypropyl acrylate malate, bicyclopentadiene malate or the (first with 1 carboxyl and 2 or more Base) acryloyl group the unsaturated polyacid such as multifunctional (methyl) acrylate；Phenol type and/or cresols type epoxy novolac tree Fat, with biphenyl backbone, the novolac epoxy resin of naphthalene skeleton, bisphenol-A phenolic type ring oxygen compound, dicyclopentadiene phenolic type ring The novolak type epoxy compounds such as oxygen compound, the polyphenyl methylmethane type ring oxygen resin with multi-functional epoxy's base make unsaturation one First acid acts on resin obtained from the epoxy groups of epoxy resin such as the epoxide represented by the following general formula (III), makes not Resin, pentaerythrite three obtained from saturation monoacid acts on the epoxy group of epoxy resin and then multi-anhydride is made to have an effect The polyfunctional acrylic ester and succinic anhydride of the hydroxyls such as acrylate, Dipentaerythritol Pentaacrylate, phthalic anhydride, The reaction product of the dibasic acid anhydrides such as tetrabydrophthalic anhydride is the polyfunctional acrylic ester etc. with acid value.

[changing 17]

(in formula, X⁴¹It indicates Direct Bonding, the alkylidene that also carbon atom number with substituent group is 1~4 sometimes, go back sometimes Carbon atom number with substituent group is 3~20 alicyclic type hydrocarbon ,-O- ,-S- ,-SO₂,-SS- ,-SO- ,-CO- ,-OCO- or Substituent group represented by above-mentioned (1-1)~(1-3),

R⁴¹、R⁴²、R⁴³And R⁴⁴Separately indicate that hydrogen atom, also the carbon atom number with substituent group is 1~5 sometimes Alkyl, the alkoxy that also carbon atom number with substituent group is 1~8 sometimes, sometimes also the carbon atom number with substituent group be 2~ 5 alkenyl or halogen atom,

The integer that m is 0~10.)

These polymerizable compounds with ethylenic bond unsaturated bond with acid value can be used alone or by two kinds with On be used in mixed way, furthermore, it is possible to be applied in combination with the polymerizable compound with ethylenic bond unsaturated bond without acid value. In the case of being use mixing two or more, their copolymerization in advance can also be used as copolymer.

In the photosensitive composite of the present invention, the polymerizable compound with ethylenic bond unsaturated bond with acid value Content is preferably 20~80 mass %, further preferably 30 in solid constituent in the solid constituent of the composition of the present invention ~70 mass %.

As the above-mentioned polymerizable compound with ethylenic bond unsaturated bond without acid value, such as (first can be enumerated Base) 2-Hydroxy ethyl acrylate, (methyl) 2-hydroxypropyl acrylate, (methyl) glycidyl acrylate, following chemical combination Object No.A1~No.A4, (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) third Olefin(e) acid-the tert-butyl ester, (methyl) cyclohexyl acrylate, (methyl) n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) third The different nonyl ester of olefin(e) acid, (methyl) stearyl acrylate, (methyl) lauryl acrylate, (methyl) methoxyethyl acrylate, (first Base) acrylate methyl esters, (methyl) acrylate, (methyl) acrylic-amino propyl ester, (first Base) acrylate propyl ester, (methyl) ethoxyethyl acrylate, poly- (ethyoxyl) ethyl ester of (methyl) acrylic acid, (first Base) acrylate, butoxy ethoxy ethyl ester, (methyl) ethylhexyl acrylate, (methyl) phenoxyethyl acrylate, (methyl) Acrylic acid tetrahydrofuran ester, (methyl) vinyl acrylate, (methyl) allyl acrylate, (methyl) benzyl acrylate, second Glycol two (methyl) acrylate, diethylene glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, poly- second two Alcohol two (methyl) acrylate, propylene glycol two (methyl) acrylate, 1,4- butanediols two (methyl) acrylate, 1,6- oneself two Alcohol two (methyl) acrylate, trimethylolethane trimethacrylate (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, dipentaerythritol six (methyl) acrylate, pentaerythrite four (methyl) acrylic acid Ester, pentaerythrite three (methyl) acrylate, tristane dihydroxymethyl two (methyl) acrylate, three [(methyl) acryloyls Base ethyl] the unsaturated monoacid such as isocyanuric acid ester, polyester (methyl) acrylate oligomer and polyalcohol or polyphenol ester； The metal salt of the unsaturation polyacid such as (methyl) zinc acrylate resin, (methyl) Magnesium Acrylate Prepared；Maleic anhydride, itaconic anhydride, citraconic acid Acid anhydride, methyl tetrahydrophthalic anhydride, tetrabydrophthalic anhydride, trialkyl tetrabydrophthalic anhydride, 5- (2,5- dioxos Tetrahydrofuran base) -3- methyl -3- cyclohexene -1,2- dicarboxylic anhydrides, trialkyl tetrabydrophthalic anhydride-maleic anhydride addition The acid anhydrides of the unsaturation polyacid such as object, dodecenylsuccinic anhydride, methyl norbornene dioic anhydride；(methyl) acrylamide, Asia Methyl is double-(methyl) acrylamide, diethylenetriamines three (methyl) acrylamide, bis- (methyl) acrylamides of xyxylene, The amide of the unsaturation monoacid such as α-chloroacrylamide, N-2- hydroxyethyls (methyl) acrylamide and polyamines；Methacrylaldehyde etc. is no Saturated aldehyde；The unsaturated nitriles such as (methyl) acrylonitrile, α-chloro-acrylonitrile, vinylidene cyanide, allyl cyanide；Styrene, 4- methyl Styrene, 4- ethyl styrenes, 4- methoxy styrenes, 4-Vinyl phenol, 4- chlorostyrenes, divinylbenzene, vinyl Toluene, vinyl benzoic acid, vinylphenol, vinyl sulfonic acid, 4- vinylbenzenesulfonic acids, vinyl benzyl methyl ether, vinyl The unsaturation aromatic compound such as benzyl glycidyl ether；The beta-unsaturated ketones such as methyl vinyl ketone；Vinyl amine, allyl amine, The unsaturated amine compounds such as n-vinyl pyrrolidone, vinylpiperidine；Methoxy ethylene, vinyl ethyl ether, n-butyl vinyl The vinyl ethers such as base ether, isobutyl vinyl ether, allyl glycidyl ether；Maleimide, N-phenylmaleimide, N- The unsaturated acyls imines such as N-cyclohexylmaleimide；The indenes such as indenes, 1- methyl indenes；1,3- butadiene, isoprene, neoprene two The aliphatic conjugated dienes class such as alkene；Polystyrene, poly- (methyl) methyl acrylate, poly- (methyl) n-butyl acrylate, poly- silica Alkane etc. has the macromonomer class of single (methyl) acryloyl group in the end of polymer molecular chain；(methyl) acrylonitrile, ethylene, Other vinyl compounds such as propylene, butylene, vinyl chloride, vinyl acetate and polymethyl methacrylate macromonomer gather The macromonomers such as styrene macromer class, the monomethacrylates of tricyclodecane skeleton, N-phenylmaleimide, The copolymer of methacryloxymethyl -3- Ethyloxetanes etc. and (methyl) acrylic acid and make they and Showa electrician (methyl) third obtained from isocyanate compound reaction with unsaturated bond as (strain) society karenz MOI, AOI Copolymer or vinyl chloride, vinylidene chloride, divinyl succinate ester, diallyl phthalate, the tricresyl phosphate allyl of olefin(e) acid Ester, triallyl isocyanurate, vinyl sulfide, vinyl imidazole, Yi Xi oxazolins, vinyl carbazole, vinyl pyrrole Alkanone, vinylpyridine, the vinyl monomer of hydroxyl and polyisocyanate compounds vinyl carbamate compound, The vinyl monomer of hydroxyl and the vinyloxirane of polyepoxides, pentaerythritol triacrylate, two seasons penta Polyfunctional acrylic ester and first phenylene diisocyanate, hexamethylene diisocyanate of the hydroxyls such as five acrylate of tetrol etc. The reaction product etc. of polyfunctional isocyanate.

[changing 18]

Compound N o.A1

[changing 19]

Compound N o.A2

[changing 20]

Compound N o.A3

[changing 21]

Compound N oA4

The developability that the photosensitive composite of the present invention is improved to adjust acid value, can be with the above-mentioned tool with acid value There is the polymerizable compound of ethylenic bond unsaturated bond to further use simple function or multi-functional epoxy compound together.It is above-mentioned to have The acid value of the preferred solid constituent of polymerizable compound with ethylenic bond unsaturated bond of acid value is the model of 5~120mgKOH/g It encloses, the usage amount of simple function or multi-functional epoxy compound preferably select in the way of meeting above-mentioned acid value.

As above-mentioned monofunctional epoxy compound, can enumerate glycidyl methacrylate, methyl glycidyl ether, Ethyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl Ether, tertiary butyl glycidyl ether, amyl glycidol ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl Ether, nonyl glycidol ether, decyl glycidyl ether, undecyl glycidol ether, lauryl diglycidyl ether, tridecane Base glycidol ether, myristyl glycidol ether, pentadecyl glycidol ether, cetyl glycidyl ether, 2- ethyls Hexyl glycidyl ether, allyl glycidyl ether, propargyl glycidol ether, to methoxy ethyl glycidol ether, phenyl Glycidol ether, to methoxyl group glycidol ether, p-butylphenol glycidol ether, cresylglycidylether, 2- methacresols Glycidol ether, 4- nonyl phenyl glycidyls glycerin ether, benzyl glycidyl ether, to cumyl phenyl glycidol ether, trityl Glycidol ether, methacrylic acid 2,3- glycidyl ester, epoxidised soybean oil, epoxidized linseed oil, butyric acid glycidol Ester, vinyl cyclohexane list oxide, 1,2- epoxy group -4- vinyl cyclohexanes, styrene oxide, pinene oxide, oxidation first Base styrene, cyclohexene oxide, propylene oxide etc..

As above-mentioned multi-functional epoxy compound, if due to using selected from by biphenol type epoxy compound and glycidol ether One or more of the group that class is constituted, then can obtain characteristic further good photosensitive composite, it is advantageous to.As this Biphenol type epoxy compound other than it can use the epoxide represented by above-mentioned logical formula (III), such as can also make With biphenol type epoxies compounds such as A Hydrogenated Bisphenol A type ring oxygen compounds.As the glycidol ethers, ethylene glycol two can be enumerated Glycidol ether, propylene glycol diglycidylether, 1,4- butanediol diglycidyl ethers, 1,6 hexanediol diglycidylether, 1,8- octanes Hexanediol diglycidyl ether, 1,10- decanediols diglycidyl ether, 2,2- dimethyl -1,3- propylene glycol two contract Water glycerin ether, diethylene glycol diglycidyl glycerin ether, Triethylene Glycol Diglycidyl Ether, tetraethylene glycol diglycidyl ether, six second Hexanediol diglycidyl ether, 1,4 cyclohexane dimethanol diglycidyl ether, 1,1,1- tri- (glycidyl oxy methyl) third Alkane, 1,1,1- tri- (glycidyl oxy methyl) ethane, 1,1,1- tri- (glycidyl oxy methyl) methane, 1,1,1,1- Four (glycidyl oxy methyl) methane.

Further, it is also possible to use phenol novolak type epoxide, biphenyl novolak type epoxy compound, cresol novolac type ring The novolak type epoxy compounds such as oxygen compound, bisphenol-A phenolic type ring oxygen compound, dicyclopentadiene phenolic type ring oxygen compound； 3,4- epoxy group -6- methylcyclohexylmethyl -3,4- epoxy group -6- methylcyclohexanecarboxylic acids ester, 3,4- expoxycyclohexyl first The cycloaliphatic epoxies such as base -3,4- epoxycyclohexane carboxylates, 1- epoxy group ethyl -3,4- epoxy-cyclohexanes；It is adjacent The glycidols such as phthalic acid 2-glycidyl ester, tetrahydrophthalic acid 2-glycidyl ester, dimer acid glycidyl ester Esters；Four glycidyl group diaminodiphenyl-methane, triglycidyl group para-aminophenol, N, N- diglycidylanilines Equal glycidols amine；The heterocycles such as 1,3- diglycidyl -5,5- dimethyl hydantoins, triglycidyl isocyanurate Formula epoxide；The dioxide compounds such as dicyclopentadiene；Naphthalene type ring oxygen compound, triphenyl methane type ring Oxygen compound, dicyclopentadiene type epoxy compound etc..

As long as above-mentioned optical free radical polymerization initiator can cause the chemical combination of free radical polymerization by receiving light irradiation Object can exemplify such as acetophenone based compound, benzil based compound, benzophenone based compound, thioxanthones system It closes ketone based compound, the oxime compounds such as object etc. and is used as preferred compound.

As acetophenone based compound, such as diethoxy acetophenone, 2- hydroxy-2-methyl -1- phenyl third can be enumerated Alkane -1- ketone, 4 '-isopropyl -2- hydroxy-2-methyls propiophenones, 2- hydroxymethyl -2- methyl phenyl ketones, dimethoxy -1 2,2-, 2- diphenylethane -1- ketone, to dimethylamino benzoylformaldoxime, to tertiary butyl dichloroacetophenone, to tertiary butyl trichloroacetophenone, right Azido benzylidene acetophenone, 1- hydroxycyclohexylphenylketones, 2- methyl-1s-[4- (methyl mercapto) phenyl] -2- morpholinoes third Ketone -1,2- benzyl -2- dimethylaminos -1- (4- morphlinophenyls)-butanone -1, benzoin, benzoin methylether, benzoin second Ether, benzoin iso-propylether, benzoin-n-butyl ether, benzoin isobutyl ether, 1- [4- (2- hydroxyl-oxethyls)-phenyl] -2- hydroxyls - 2- methyl-1s-propane -1- ketone etc..

As benzil based compound, benzil, anisil etc. can be enumerated.

As benzophenone based compound, such as benzophenone, o-benzoyl yl benzoic acid methyl esters, meter Xi Le can be enumerated Ketone, 4,4 '-bis- diethylamino benzophenone, 4,4 '-dichloro benzophenones, 4- benzoyls -4 '-dimethyl diphenyl sulfide Deng.

As thioxanthones based compound, thioxanthones, 2- methyl thioxanthones, 2- ethyls thioxanthones, 2- diuril tons can be enumerated Ketone, 2-isopropylthioxanthone, 2,4- diethyl thioxanthones etc..

As the compound represented by oxime compound, especially the following general formula (IV) or (V) from sensitivity and heat resistance Aspect is set out preferably.

[changing 22]

(in formula, R⁵¹And R⁵²Separately indicate that hydrogen atom, cyano, also the carbon atom number with substituent group is 1 sometimes ~20 alkyl, the aryl that also carbon atom number with substituent group is 6~30 sometimes, the sometimes also carbon atom number with substituent group For 7~30 aryl alkyl or sometimes also with substituent group carbon atom number be 2~20 contain heterocyclic group,

R⁵³And R⁵⁴Separately indicate halogen atom, nitro, cyano, hydroxyl, carboxyl, R⁵⁵、OR⁵⁶、SR⁵⁷、NR⁵⁸R⁵⁹、 COR⁶⁰、SOR⁶¹、SO₂R⁶²Or CONR⁶³R⁶⁴, R⁵³And R⁵⁴Sometimes it also bonds together and forms ring,

R⁵⁵、R⁵⁶、R⁵⁷、R⁵⁸、R⁵⁹、R⁶⁰、R⁶¹、R⁶²、R⁶³And R⁶⁴Separately indicate that also the carbon with substituent group is former sometimes Alkyl that subnumber is 1~20, the aryl that also carbon atom number with substituent group is 6~30 sometimes, sometimes also with substituent group Aryl alkyl that carbon atom number is 7~30 or also the carbon atom number with substituent group is 2~20 to contain heterocyclic group sometimes,

X³Indicate oxygen atom, sulphur atom, selenium atom, CR⁷⁵R⁷⁶、CO、NR⁷⁷Or PR⁷⁸,

X⁴Indicate singly-bound or CO,

R⁷⁵~R⁷⁸Indicate aryl that alkyl, carbon atom number that carbon atom number is 1~20 are 6~30 or carbon atom number be 7~ 30 aryl alkyl, methylene in the alkyl or aryl alkyl sometimes also by halogen atom, nitro, cyano, hydroxyl, carboxyl or Replace containing heterocyclic group, also replaced sometimes by-O-,

R⁵³And R⁵⁴Sometimes ring separately also is formed with together with any one adjacent phenyl ring,

A indicates 0~4 integer,

B indicates 0~5 integer.)

[changing 23]

(in formula, R¹⁰¹And R¹⁰²Separately indicate R¹¹¹、OR¹¹¹、COR¹¹¹、SR¹¹¹、CONR¹¹²R¹¹³Or CN,

R¹¹¹、R¹¹²And R¹¹³Separately indicate alkyl, carbon atom number that hydrogen atom, carbon atom number are 1~20 be 6~ Aryl alkyl or carbon atom number that 30 aryl, carbon atom number are 7~30 is 2~20 to contain heterocyclic group,

R¹¹¹、R¹¹²And R¹¹³The hydrogen atom of represented group is sometimes also further by R¹²¹、OR¹²¹、COR¹²¹、SR¹²¹、 NR¹²²R¹²³、CONR¹²²R¹²³、-NR¹²²-OR¹²³、-NCOR¹²²-OCOR¹²³、NR¹²²COR¹²¹、OCOR¹²¹、COOR¹²¹、SCOR¹²¹、 OCSR¹²¹、COSR¹²¹、CSOR¹²¹, hydroxyl, nitro, CN or halogen atom substitution,

R¹²¹、R¹²²And R¹²³Separately indicate alkyl, carbon atom number that hydrogen atom, carbon atom number are 1~20 be 6~ Aryl alkyl or carbon atom number that 30 aryl, carbon atom number are 7~30 is 2~20 to contain heterocyclic group,

R¹²¹、R¹²²And R¹²³The hydrogen atom of represented group sometimes also further by hydroxyl, nitro, CN, halogen atom, Hydroxyl or carboxyl substitution,

R¹¹¹、R¹¹²、R¹¹³、R¹²¹、R¹²²And R¹²³The alkylene moiety of represented group sometimes also by-O- ,-S- ,- COO-、-OCO-、-NR¹²⁴-、-NR¹²⁴COO-、-OCONR¹²⁴,-SCO- ,-COS- ,-OCS- or-CSO- it is non-conterminous in oxygen atom Under conditions of substituted 11~5 time,

R¹²⁴Indicate the aryl that alkyl, carbon atom number that hydrogen atom, carbon atom number are 1~20 are 6~30, carbon atom number 7 ~30 aryl alkyl or carbon atom number be 2~20 contain heterocyclic group,

R¹¹¹、R¹¹²、R¹¹³、R¹²¹、R¹²²、R¹²³And R¹²⁴The moieties of represented group also have branched side chains sometimes, Sometimes also it is cyclic alkyl,

R¹⁰³Indicate the aryl that alkyl, carbon atom number that hydrogen atom, carbon atom number are 1~20 are 6~30, carbon atom number 7 ~30 aryl alkyl or carbon atom number is 2~20 containing heterocyclic group, R¹⁰³The moieties of represented group also have sometimes There are branched side chains, is also sometimes cyclic alkyl, in addition, R¹⁰³With R¹⁰⁷、R¹⁰³With R¹⁰⁸、R¹⁰⁴With R¹⁰⁵、R¹⁰⁵With R¹⁰⁶And R¹⁰⁶With R¹⁰⁷Sometimes ring is also formed together respectively,

R¹⁰³The hydrogen atom of represented group is sometimes also further by R¹²¹、OR¹²¹、COR¹²¹、SR¹²¹、NR¹²²R¹²³、 CONR¹²²R¹²³、-NR¹²²-OR¹²³、-NCOR¹²²-OCOR¹²³、NR¹²²COR¹²¹、OCOR¹²¹、COOR¹²¹、SCOR¹²¹、OCSR¹²¹、 COSR¹²¹、CSOR¹²¹, hydroxyl, nitro, CN, halogen atom or COOR¹²¹Substitution,

R¹⁰⁴、R¹⁰⁵、R¹⁰⁶And R¹⁰⁷Separately indicate R¹¹¹、OR¹¹¹、SR¹¹¹、COR¹¹⁴、CONR¹⁵¹R¹¹⁶、 NR¹¹²COR¹¹¹、OCOR¹¹¹、COOR¹¹⁴、SCOR¹¹¹、OCSR¹¹¹、COSR¹¹⁴、CSOR¹¹¹, hydroxyl, CN or halogen atom, R¹⁰⁴With R¹⁰⁵、R¹⁰⁵With R¹⁰⁶And R¹⁰⁶With R¹⁰⁷Sometimes ring is also formed together respectively,

R¹¹⁴、R¹¹⁵And R¹¹⁶Indicate the alkyl that hydrogen atom or carbon atom number are 1~20,

R¹⁰⁸Indicate R¹¹¹、OR¹¹¹、SR¹¹¹、COR¹¹¹、CONR¹¹²R¹¹³、NR¹¹²COR¹¹¹、OCOR¹¹¹、COOR¹¹¹、SCOR¹¹¹、 OCSR¹¹¹、COSR¹¹¹、CSOR¹¹¹, hydroxyl, CN or halogen atom,

W indicates 0 or 1.)

As other optical free radical polymerization initiators, can enumerate 2,4,6-trimethylbenzoyldiphenylphosphine oxide, Bis- (cyclopentadienyl groups)-bis- [bis- fluoro- 3- of 2,6- (pyrroles -1- bases)] titaniums etc..

As expected these optical free radical polymerization initiators performance can coordinate a kind or two or more and use.

In the solid constituent of photosensitive composite of the content of above such optical free radical polymerization initiator in the present invention For 0.1~30 mass %, particularly preferably 0.5~10 mass %.If the content of above-mentioned optical free radical polymerization initiator is less than 0.1 Quality % then becomes inadequate sometimes with the solidification of exposure, if more than 30 mass %, is then analysed in photosensitive composite sometimes Go out initiator.

The photosensitive composite of the present invention further can also be added colorant and coloring photosensitive combination is made.It is somebody's turn to do The solidfied material of color photosensitive composite can be used as colour filter suitable for using.

In the coloring photosensitive combination of the present invention, the additive amount of colorant is in coloring photosensitive combination of the invention Solid constituent in preferably 0.01~50 mass %, more preferably 0.1~30 mass %.If the content of above-mentioned colorant is less than 0.01 mass %, then cannot get desired coloration sometimes, if more than 50 mass %, then sometimes in coloring photosensitive combination Colorant is precipitated.

As above-mentioned colorant, dyestuff or pigment can be enumerated.

As dyestuff, as long as at 380~1200nm there is the compound absorbed to be not particularly limited, can enumerate Such as azo-compound, anthraquinone compounds, indigoid compound, triaryl methane compounds, xanthene compound, alizarin chemical combination Object, acridine compounds, stilbene compounds, thiazolium compounds, naphthol compound, quinoline compound, nitro compound, Yin rattle away amine compounds Object, oxazine compounds, phthalocyanine compound, cyanine compound, diimmonium salt compound, cyano vinyl based compound, dicyano In distyryl compound, rhodamine compound, compound, polyenoid naphthalene lactim compound, coumarin compound, side are sour Salt compound, crocic acid compound, spiropyran compounds, Luo oxazine compounds, merocyanine compound, oxonol compound, Compound of styryl, rhodanine compound, oxazole ketone compound, phthalimide compound, is scolded at pyrylium compound Quinoline compound, naphthoquinone compound, azepine anthraquinone compound, porphyrin compound, aza porphyrin compound, methylene azole compounds, Quinacridone compound, diketopyrrolo-pyrrole compound, indigo compound, acridine compounds, azines, azomethine Close object, aniline compound, quinacridone compound, quinophthalone compound, quinone-imine compound, iridium complex compound, europium network Dyestuffs such as chelate compound etc., they can also be used in mixed way a variety of.

As pigment, inorganic pigment or organic pigment can be used, such as nitroso compound, nitro compound can be used Object, azo-compound, diazonium compound, xanthene compound, quinoline compound, anthraquinone compounds, coumarin compound, phthalocyanine Close object, isoindolinone compounds, isoindoline compounds, quinacridone compound, anthanthrone compound, purple cyclic ketones chemical combination Object, compound, diketopyrrolo-pyrrole compound, thioindigo compound, dioxazine compounds, triphenylmethane compounds, quinoline Phthalein ketone compound, naphthalene tetracarboxylic acid；The metal complex compounds of azo dyes, cyanine dye；Mordant pigment；Pass through oven process, slot The carbon blacks such as carbon black or acetylene black, Ketjen black or lampblack obtained from method, pyrolysis method；Above-mentioned carbon black is adjusted with epoxy resin, Above-mentioned carbon black is carried out decentralized processing with resin in a solvent in advance and has adsorbed 20~200mg/g by substance obtained from coating Resin obtained from substance, above-mentioned carbon black is carried out to substance, average grain diameter 8nm obtained from the processing of acid or basic surface Above and DBP oil absorptions are 90ml/100g substances below, by CO, CO in the volatile ingredient at 950 DEG C₂The total oxygen calculated Measure the surface area 100m relative to carbon black²For the substance of 9mg or more；Graphite, Graphon, activated carbon, carbon fiber, carbon nanometer Pipe, screw carbon fibre (Carbon microcoil), carbon nanohorn, carbon aerogels, fullerene；Nigrosine, pigment black 7, titanium It is black；Hydrophobic resin, chrome oxide green, milori blue, cobalt green, cobalt ultramarine, manganese systems, ferrocyanide, phosphate ultramarine, Prussia The sharp Dean pigment of indigo plant, ultramarine, cerulean blue, dimension, emerald green, lead sulfate, chrome yellow, zinc yellow, iron oxide red (red iron oxide (III)), inorganic pigments or the organic pigment such as cadmium red, synthesis iron oxide black, umber.These pigment can be used alone or will be a variety of mixed It closes and uses.

As above-mentioned inorganic pigment or organic pigment, commercially available pigment can also be used, can enumerate such as paratonere 1, 2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、 169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、 227、228、240、254；Pigment orange 13,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,65, 71；Pigment yellow 1,3,12,13,14,16,17,20,24,55,60,73,81,83,86,93,95,97,98,100,109,110, 113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、 168、175、180、185；Pigment Green 7,10,36；Pigment blue 15,15：1、15：2、15：3、15：4、15：5、15：6、22、24、 56、60、61、62、64；Pigment violet 1,19,23,27,29,30,32,37,40,50 etc..

In the photosensitive composite and coloring photosensitive combination of the present invention, solvent can be further added.As this Solvent can usually enumerate and can dissolve or disperse the solvent of above-mentioned each ingredient, such as methyl ethyl ketone, methyl amyl as needed The ketones such as ketone, diethyl ketone, acetone, methyl isopropyl Ketone, methyl iso-butyl ketone (MIBK), cyclohexanone, 2-HEPTANONE；Ether, dioxanes, tetrahydrochysene The ether series solvents such as furans, 1,2- dimethoxy-ethanes, 1,2- diethoxyethane, dimethyl ether；Methyl acetate, acetic acid Ethyl ester, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, 2,2,4- The ester series solvents such as trimethyl -1,3- pentanediol mono isobutyrates (Texanol)；Glycol monoethyl ether, ethylene glycol monoethyl ether etc. are molten Fine agent series solvent；The alcohol series solvents such as methanol, ethyl alcohol, isopropanol or normal propyl alcohol, isobutanol or n-butanol, amylalcohol, diacetone alcohol；Second Glycol monomethylether acetate, ethylene glycol monoethylether acetate, propylene glycol -1- monomethyl ether -2- acetic acid esters (PGMEA), dipropylene glycol Methyl ether acetate, acetic acid 3- methoxybutyls, ethoxyethyl propionate, 1- tert-butoxy -2- propyl alcohol, acetic acid 3- methoxyl group fourths The ether-ethers series solvent such as ester, adnoral acetate；The BTX series solvents such as benzene,toluene,xylene；Hexane, heptane, octane, hexamethylene etc. Aliphatic hydrocarbon series solvent；The terpenic series hydrocarbon ils such as turpentine oil, D- limonenes, firpene；Mineral spirits, Swasol#310 (COSMO MATSUYAMA OIL CO., LTD.), the alkanes hydrocarbon system solvent such as SOLVESSO#100 (Exon Chemical Co., Ltd.)；Four The halogenated aliphatics hydrocarbon system solvents such as chlorination carbon, chloroform, trichloro ethylene, dichloromethane, 1,2- dichloroethanes；The halogenated aromatics such as chlorobenzene Race's hydrocarbon system solvent；Carbitol series solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), water etc., these solvents can use a kind or as two kinds Above mixed solvent uses.In them, ketone, ether-ether series solvent etc. are especially propylene glycol -1- monomethyl ether -2- acetic acid esters, ring Hexanone etc. since the compatibility of resist and optical free radical polymerization initiator in photosensitive composite is good, it is advantageous to. In the case of using solvent, from the viewpoints such as processing, preferably photosensitive composite or coloring photosensitive combination of the invention Solid constituent with reach 25~35 mass % amount use.

In the photosensitive composite and coloring photosensitive combination of the present invention, it can further contain inorganic compound.Make For the inorganic compound, can enumerate for example nickel oxide, iron oxide, yttrium oxide, titanium oxide, zinc oxide, magnesia, calcium oxide, The metal oxides such as potassium oxide, silica, aluminium oxide；Layered clay mineral, milori blue, calcium carbonate, magnesium carbonate, cobalt system, Manganese systems, glass powder, mica, talcum, kaolin, ferrocyanide, various metal sulfates, sulfide, selenides, silicic acid Aluminium, calcium silicates, aluminium hydroxide, platinum, gold, silver, copper etc..

In the photosensitive composite and coloring photosensitive combination of the present invention, colorants and/or the nothings such as pigment are being used In the case of machine compound, dispersant can be added.As the dispersant, as long as can be by colorant, inorganic compound point Scattered, stabilized substance is then not particularly limited, and can use commercially available dispersant, the BYK of such as BYK-Chemie corporations Series etc., suitable for using comprising with basic functionality polyester, polyethers, the macromolecule dispersing agent of polyurethane, with nitrogen-atoms As basic functionality and with nitrogen-atoms the substance that functional group is amine and/or its quaternary salt, amine value are 1~100mgKOH/g.

In addition, in the photosensitive composite and coloring photosensitive combination of the present invention, can be added to fennel as needed The thermal polymerization inhibitors such as ether, quinhydrones, pyrocatechol, tert-butyl catechol, phenthazine；Plasticizer；Adhesion promoters；Filler； Antifoaming agent；Levelling agent；Surface conditioner；The antioxygens such as phenolic antioxidant, phosphite ester system antioxidant, thioether antioxidant Agent；Ultra-violet absorber；Dispersing aid；It is aggregated preventing agent；Catalyst；Effect accelerating agent；Crosslinking agent；Thickener etc. is usual Additive.

In addition, by being used together other with the above-mentioned polymerizable compound with ethylenic bond unsaturated bond with acid value Organic polymer, additionally it is possible to improve the characteristic of the photosensitive composite of the present invention and the solidfied material of coloring photosensitive combination.Make For above-mentioned organic polymer, such as polystyrene, polymethyl methacrylate, methyl methacrylate-acrylic acid can be enumerated Methacrylate copolymers, poly- (methyl) acrylic acid, styrene-(methyl) acrylic copolymer, (methyl) acrylic acid-methacrylic acid first Ester copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl base co-polymer, Corvic, ABS resin, nylon 6, nylon 66, nylon 12, carbamate resins, makrolon polyvinyl butyral, cellulose esters, polyacrylamide, saturated polyester, Phenolic resin, phenoxy resin, polyamide-imide resin, polyamic acid resin, epoxy resin etc., in them, preferred polyphenyl Ethylene, (methyl) acryl acid-methyl methacrylate copolymer, epoxy resin.

In the photosensitive composite and coloring photosensitive combination of the present invention, can further and with chain-transferring agent, increasing it feel Agent, surfactant, silane coupling agent, melamine compound etc..

As above-mentioned chain-transferring agent, sensitizer, the compound of sulfur atom-containing is generally used.Such as sulfydryl second can be enumerated Acid, thiomalic acid, thiosalicylic acid, 2 mercaptopropionic acid, 3- mercaptopropionic acids, 3- mercaptobutyric acids, N- (2- mercapto radical propionyl groups) are sweet Propylhomoserin, 2- mercaptonicotinic acids, 3- [N- (2- mercaptoethyls) carbamoyl] propionic acid, 3- [N- (2- mercaptoethyls) amino] propionic acid, N- (3- mercapto radical propionyl groups) alanine, mistabrom, 3- thiohydracrylic acids, 4- sulfydryl fourths sulfonic acid, dodecyl (4- first sulphur Base) phenylate, 2 mercapto ethanol, 3- sulfydryl -1,2- propylene glycol, 1- sulfydryl -2- propyl alcohol, 3- sulfydryl -2- butanol, mercapto-phenol, 2- Mercaptoethylmaine, 2- mercaptoimidazoles, 2-mercaptobenzimidazole, 2- sulfydryl -3- pyridols, 2-mercaptobenzothiazole, thioacetic acid, three The sulfhydryl compounds such as hydroxymethyl-propane three (3-thiopropionate), pentaerythrite four (3-thiopropionate), by the sulfydryl chemical combination The iodine such as di-sulphide compounds, iodoacetic acid, iodopropionic acid, ethylene iodohydrin, 2- iodine ethanesulfonic acid, 3- iodine propane sulfonic acid obtained from object oxidation Substituted alkyl compound, trimethylolpropane tris (3- mercaptoisobutanoics acid esters), butanediol bis- (3- mercaptoisobutanoics acid esters), oneself two sulphur The double thiopropionates of alcohol, two mercaptan of the last of the ten Heavenly stems, 1,4- dimethyl sulfydryls benzene, butanediol, the double mercaptoacetates of butanediol, the double mercaptos of ethylene glycol Yl acetate, trimethylolpropane tris mercaptoacetate, butanediol double thiopropionate, trimethylolpropane tris propane thioic acids Ester, trimethylolpropane tris mercaptoacetate, pentaerythrite tetrathio propionic ester, four mercaptoacetate of pentaerythrite, trihydroxy The aliphatic such as three thiopropionate of ethyl, following compound N o.C1, tri-thiol propionic acid three (2- hydroxyethyls) isocyanuric acid ester are more Functional thiols's compound, Showa electrician society karenz MT BD1, PE1, NR1 etc..

[changing 24]

Compound N o.C1

As above-mentioned surfactant, the fluorine surface-actives such as perfluoralkyl phosphate, perfluoroalkyl carboxylate can be used The anionic surfactants such as agent, higher aliphatic acid-alkali salt, alkylsulfonate, alkyl sulfate, higher amines halate, quaternary ammonium The cationic systems such as salt surfactant, polyethylene glycol alkyl ether, cithrol, sorbitan fatty acid ester, fat The surfactants such as nonionic surfactants, amphoteric surfactant, the silicone based surfactants such as fat acid monoglyceride, They can also be applied in combination.

As above-mentioned silane coupling agent, such as SHIN-ETSU HANTOTAI's chemistry society silane coupling agent can be used, wherein suitable for using The silane coupling agent with isocyanate group, methylacryloyl, epoxy group such as KBE-9007, KBM-502, KBE-403.

As above-mentioned melamine compound, (poly-) melamine methylol, (poly-) methylol glycoluril, (poly-) can be enumerated Active methylol (CH in the nitrogen compounds such as methylolbenzoguanamine, (poly-) methylolurea₂OH yls) all or part of (extremely It is 2 few) compound obtained from alkyl etherified.Here, as constitute alkyl ether alkyl, can enumerate methyl, ethyl or Butyl, it is sometimes mutually the same, it is sometimes also different.In addition, do not self condensed sometimes in an intramolecular by alkyl etherified methylol, Sometimes also in two intermolecular condensations, as a result, forming oligomer ingredient.Specifically, hexamethoxy methyl trimerization can be used Cyanamide, six butoxymethyl melamines, tetramethoxymethylglycoluril, four butoxymethyl glycolurils etc..In them, preferably pregnancy Oxygroup methyl melamine, six butoxymethyl melamines etc. are through alkyl etherified melamine.

The photosensitive composite and coloring photosensitive combination of the present invention can pass through spin coater, roll coater, bar coater, mould Painting machine, curtain coater, various printings, means well known to impregnating are applied to soda-lime glass, quartz glass, semiconductor substrate, gold In the support substrates such as category, paper, plastics.In addition it is also possible to after being implemented on for the time being in the support substrates such as film, it is transferred to other branch support groups On body, being applied to method, there is no limit.

The active light used when in addition, curing as the photosensitive composite and coloring photosensitive combination for making the present invention Light source can use the light source for sending out the light that wavelength is 300~450nm, ultra high pressure mercury, mercury vapour arc, carbon can be used for example Arc, xenon arc etc..

In turn, by using laser, straight from the digital information without the use of mask just by computer etc. in exposure light source Raising of the direct picture of laser to form image due to can not only seek productivity is connect, clarity or positional precision can be also sought Deng raising, so being useful, as the laser, suitable for using the light of the wavelength of 340~430nm, it is possible to use argon ion Laser, He-Ne laser, YAG laser and semiconductor laser etc. can send out the laser of the light from visible infrared region Device.Using these lasers, the sensitizing coloring matter absorbed from the visible infrared region can be added.

The photosensitive composite and coloring photosensitive combination of the present invention can also be via using two kinds of photosensitive composites Or coloring photosensitive combination and it is divided into and carries out patterned double patterning technique twice and patterned.

The photosensitive composite or the cured method of coloring photosensitive combination for making the present invention include following process：By upper State that spin coater, roll coater, bar coater, die coating machine, curtain coater, various printings, means are coated on sodium glass well known to impregnating The process for forming film in the support substrates such as glass, quartz glass, semiconductor substrate, metal, paper, plastics；And the film is exposed The above-mentioned active light of light and make its cured process.

The photosensitive composite and coloring photosensitive combination (or its solidfied material) of the present invention can be used for photo-curable painting Bonding agents, tellite or the colour television set such as material or varnish, Photocurable adhesive agent, PC monitors, mobile information are whole The colour filter of colour filter, ccd image sensor in the liquid crystal display panel of the colored display such as end, digital camera, light spacer, Black columnar interval device, the electrode material of plasma display panel, touch panel, touch sensor, powdery paints, printing Ink, galley, dental composition, light appearance resin, gel paint, the photoresist of electronic engineering, plating are against corrosion Both agent, etching resist, liquid and desciccator diaphragm, solder resist, the colour filters for manufacturing various display purposes or Plasma display panel, electrical luminous display unit and be used to form in the manufacturing process of LCD structure resist, use In enclosed electrical and the composition of electronic unit, solder resist, magnetic recording material, milli machine component, waveguide, optical switch, plating Cover with mask, etching mask, color test system, glass fiber cable coatings, silk-screen printing stencilling, for passing through cubic light Carve and manufacture the material of three-dimension object, holographic recording material, image recording material, fine electronic circuit, decoloring material, Decoloring material, the printed wiring board-use of decoloring material for image recording material, the image recording material using microcapsules Photo anti-corrosion agent material, the photo anti-corrosion agent material of UV and visible laser through image system, printed circuit board are gradually It is each that dielectric layer in stacking forms the middle photo anti-corrosion agent material used, 3D installations photo anti-corrosion agent material or protective film etc. Kind purposes, is not particularly limited its purposes.

The photosensitive composite of the present invention can be used by making its solidification as transparent configuration body.As transparent configuration Body can enumerate the pillars for being for example referred to as light spacer (PS), column spacer (CS)；The fine figure of (nanometer) stamp Case；It is used in the electronic equipment manufacturings such as the printing of the manufacture of large board etc. or color filter for liquid crystal display or alignment films Inkjet receiver layer etc..The transparent configuration body of the present invention is suitable for display equipment.

The present invention photosensitive composite can be used for transparent conductive film, reflectance coating, polarizing film, protective film etc., by Desired each layer is coated on transparent substrate successively, via the active light of mask irradiation with defined pattern form, will be exposed Envelope afterwards is developed by developer solution, and the envelope after development is heated, can be as the Sparent laminate of stacking It uses.As Sparent laminate, it can enumerate and for example be alternately laminated with over the transparent substrate by the compound of indium oxide and cerium oxide The laminated body etc. for the transparent thin film layer and metal film layer that oxide is formed.It can respectively be used containing tool in above-mentioned each layer Of the invention photosensitive composite of the compound as latency additive for having the substituent group represented by logical formula (I), can also The photosensitive composite is used in any layer.In addition, in turn, which is suitable for display device.

The present invention coloring photosensitive combination be to be used to form the pixel of colour filter, especially as It is useful to form the photosensitive composite of the display equipment colour filters of device used for image display such as liquid crystal display panel.

Above-mentioned display equipment preferably forms the coloring photosensitive combination of the present invention with colour filter by (1) on substrate The process of film, (2) irradiate the process of active light via the mask with defined pattern form to the film, (3) will expose Process that envelope afterwards is developed by developer solution, (4) form the process that the envelope after development heats.This Outside, coloring photosensitive combination of the invention is also useful as the coloring photosensitive combination of the ink-jet mode of nonvisualization process 's.

As aforementioned mask, more gray scale masks such as half-tone mask or gray-tone mask can also be used.

Then, the new compound of the present invention is illustrated.The new compound of the present invention is with appointing in following structures One indicates.

[changing 25]

[changing 26]

[changing 27]

The manufacturing method of the new compound of the present invention is not particularly limited, and can make for example through Japanese Unexamined Patent Application 57- No. 111375, Japanese Unexamined Patent Publication 3-173843, Japanese Unexamined Patent Publication 6-128195, Japanese Unexamined Patent Publication 7-206771, Japan Unexamined Patent 7-252191, Japanese Unexamined Patent Application Publication 2004-501128 each bulletin described in method and the phenol system compound that manufactures It reacts and obtains with halogenated allyl compound etc..

The new compound of the present invention can be used for latency antioxidant, latency ultra-violet absorber, dissolving adjustment Agent etc..

Embodiment

The present invention is illustrated in more details hereinafter, enumerating embodiment etc., but the present invention is not limited to these realities Apply example etc..

The synthesis of [embodiment 1-1] compound N o.1

Following compound Ns o.1 ' 1 equivalent of oxybenzene compound dimethylacetamide solution 3 times of theoretical yield (amount) Middle addition potassium carbonate (being 2 equivalents relative to 1 phenylol), is stirred at room temperature 30 minutes.It is (opposite that allylbromide is added In 1 phenylol be 1.5 equivalents), stirred 5 hours at 60 DEG C.Ethyl acetate is added and is carried out after being washed with 1% hydrochloric acid solution After drying organic layer with anhydrous sodium sulfate, solvent is distilled off for water-oil separating, carries out partial crystallization.Obtained solid is set to exist At 60 DEG C be dried under reduced pressure within 3 hours, obtains object.Pass through¹H-NMR, IR confirm that obtained solid is object.It will knot Fruit is shown in [table 1]~[table 2].

The synthesis of [embodiment 1-2~1-6] compound N o.2~6

Oxybenzene compound in addition in embodiment 1-1, o.2 using following compound Ns '~6 ' replaces following compounds Other than the oxybenzene compound of No.1 ', operated in the same manner as embodiment 1-1, synthesize as object compound N o.2~6.It is logical It crosses¹H-NMR, IR confirm that obtained solid is object.It shows the result in [table 1]~[table 2].

[changing 28]

[changing 29]

Table 1

¹H-NMR (solvents：CDCl₃)

Table 2

[embodiment 2-1~2-2 and comparative example 2-1~2-3] photosensitive composite No.1~No.2 and compare photonasty group Close the preparation of object No.1~No.3

By SPC-1000 (Showa electrician society system, the PGMEA solution that solid constituent is 29%) 50.0g, ARONIX M-450 (East Asia synthesizes society's system) 11.6g, NCI-930 (ADEKA societies system) 0.3g, PGMEA 34.7g, FZ2122 (Dow Corning Toray Co., Ltd.s system, the PGMEA solution that solid constituent is 1%) compound 0.81g mixing that 2.9g and [table 3] are recorded, it stirs It mixes to insoluble matter and disappears, obtain photosensitive composite No.1~No.2 and compare photosensitive composite No.1~No.3.

Table 3

	Additive
		Embodiment 2-1	Compound N is o.1
Embodiment 2-2	Compound N is o.2
		Comparative example 1-1	Compare compound N o.1
Comparative example 1-2	Compare compound N o.2
		Comparative example 1-3	Nothing

[changing 30]

Compound N is o.2

[changing 31]

Compare compound N o.1

[changing 32]

Compare compound N o.2

[evaluation example 1-1 and comparative evaluation example 1-1] exhaust evaluation

Measure respectively the compound N of 5mg o.1, compound N o.2 and compare compound N o.2, pass through thermal mass and measure dress It sets after from room temperature to 230 DEG C (20 DEG C/min.), measures weight reduction rates at the time of being maintained at 230 DEG C 30 minutes. It is evaluated as photosensitive composite No.1~No.2 and the exhaust for comparing photosensitive composite No.2.Weight reduces smaller, expression Exhaust is fewer.It shows the result in [table 4].

Table 4

	Compound	Photosensitive composite	Weight reduction rates
				Evaluate example 1-1	Compound N is o.1	Photosensitive composite No.1	0.1%
Evaluate example 1-2	Compound N is o.2	Photosensitive composite No.2	0.1%
				Comparative evaluation example 1-1	Compare compound N o.2	Compare photosensitive composite No.2	36%

Show that the exhaust of the compound of the present invention is few by the above results, the sense of the present invention containing the compound of the present invention The exhaust of photosensitiveness composition tails off.

[evaluation example 2-1 and comparative evaluation example 2-1~2-2] solvent resistance evaluation

The comparison sense that will be obtained in the photosensitive composite No.1 obtained in above-described embodiment 2-1 and comparative example 2-1 and 2-3 Photosensitiveness composition No.1 and No.3 carry out application with the condition of 410rpm × 7 second on the glass substrate respectively, make it by hot plate Dry (90 DEG C × 90 seconds).(40mJ/cm is exposed with ultrahigh pressure mercury lamp to obtained film²).By the film after exposure It is burnt into 230 DEG C × 30 minutes conditions.After the film thickness for measuring obtained film, at room temperature in PGMEA, hexamethylene It is impregnated 30 minutes in ketone, N-Methyl pyrrolidone, N- ethyl pyrrolidones, measures the film thickness after dipping.The front and back film thickness of dipping Than (film thickness before the dipping of film thickness after dipping × 100/) closer to 100%, then it is higher to be evaluated as solvent resistance.

Table 5

Shown compared with the solidfied material of the comparison photosensitive composite No.3 without containing antioxidant by [table 5], containing with The solvent resistance of the solidfied material of the comparison photosensitive composite No.1 of past phenolic antioxidant declines, but has used the application's The case where compound is maintained as the photosensitive composite No.1 of latency additive with without containing antioxidant is identical resistance to molten Agent.

As can be known from the above results, used the compound of the present invention as the photosensitive composite of latency additive Exhaust is few, the excellent solvent resistance of solidfied material.

Industrial availability

In accordance with the invention it is possible to provide used at normal temperatures for it is nonactive and as defined in be heated to temperature by lived Change show the compound of the function as antioxidant or ultra-violet absorber, exhaust less and the solvent resistant of solidfied material The high photosensitive composite of property.

Claims

1. a kind of photosensitive composite contains the compound with the substituent group represented by the following general formula (I),

In formula, R¹And R²Separately indicate hydrogen atom, halogen atom, cyano, hydroxyl, nitro, carboxyl, sometimes also have take Alkyl that the carbon atom number of Dai Ji is 1~40, also has the aryl that also carbon atom number with substituent group is 6~20 sometimes sometimes Aryl alkyl that the carbon atom number of substituted base is 7~20, also the carbon atom number with substituent group is 2~20 to contain heterocycle sometimes Group or trialkylsilkl,

R¹And R²Methylene in represented alkyl or aryl alkyl will be also selected from sometimes-O- ,-S- ,-CO- ,-O-CO- ,- CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、- NR '-,-S-S- or-SO₂In group combined under the conditions of oxygen atom is non-conterminous obtained from group replace, R ' indicate hydrogen The alkyl that atom or carbon atom number are 1~8,

J indicates 1~3 number,

* refer in the parts * and adjacent group bonding.

2. photosensitive composite according to claim 1, wherein the above-mentioned change with the substituent group represented by logical formula (I) Conjunction object is the compound represented by the following general formula (I-A),

In formula, n indicates 1~10 integer,

X¹Indicate the combination base of n valences,

R¹、R²And j is identical as above-mentioned logical formula (I).

3. a kind of solidfied material is the solidfied material of photosensitive composite as claimed in claim 1 or 2.

4. a kind of display equipment, is to have using the solidfied material described in claim 3 at least part and formed saturating Equipment is shown made of bright laminated body or transparent configuration body.

5. a kind of coloring photosensitive combination is to make further to contain in photosensitive composite as claimed in claim 1 or 2 to have Coloring photosensitive combination made of toner.

6. a kind of solidfied material is the solidfied material of the coloring photosensitive combination described in claim 5.

7. a kind of colour filter is the colour filter formed using the solidfied material described in claim 6.

8. a kind of method is the colored photosensitive made described in photosensitive composite as claimed in claim 1 or 2 or claim 5 The property cured method of composition comprising following process：By photosensitive composite as claimed in claim 1 or 2 or claim 5 The coloring photosensitive combination is coated in support substrate and the process that forms film；And active light is exposed to the film And make its cured process.

9. a kind of new compound is indicated with any one of following structures (A) to (O),