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    • 4. 发明授权
    • Trifunctional photoinitiators
    • 三功能光引发剂
    • US07462650B2
    • 2008-12-09
    • US10552952
    • 2004-05-04
    • Reinhard H. SommerladeRinaldo HüslerStephan IlgAndré FuchsSouâd BoulmaâzJean-Luc Birbaum
    • Reinhard H. SommerladeRinaldo HüslerStephan IlgAndré FuchsSouâd BoulmaâzJean-Luc Birbaum
    • C08F2/46C07C49/00
    • G03F7/0295B33Y70/00C07C45/46C07C45/63C07C45/64C07C45/71C07C49/784C07C49/813C07C49/83C07C49/84C07C225/22C07C271/20C07C2601/14C08F2/50G03F7/029G03F7/031
    • The Invention relates to novel ketones of formulae (I) and (II) wherein R1, R2, R3 and R4 are, for example, C1-C8alkyl, R5 is, for example, hydrogen, A is CI, Br, -0-R7, —NR8R9 or —S—R16, A′ is —O—, —NH— or —NR8—, X and Y are each independently of the other —O—R10 or —N(R11)(R12), n is an integer from 1 to 10, R6 is, for example, an n-valent radical of linear or branched C2-C20alkyl the carbon chain of which may be interrupted by cyclohexanediyl, phenylene, —CH(OH)—, —C(C2H5)(CH2—CH2—OH)—, —C(CH3)(CH2—CH2—OH)—, —C(CH2—CH2—OH)2—, —N(CH3)—, —N(C2H5)—, —N(CH2—CH2—OH)—, —CO—O—, —O—CO—, —P(CH2—CH2—OH)—, —P(O)(CH2—CH2—OH)—, -0-P(O—CH2—CH2—OH)—O—, -0-P(O)(0-CH2—CH2—OH)—O—, —O-cyclohexanediyl-C(CH3)2-Cyclohexanediyl-O—, —O-phenylene-C(CH3)2-phenylene-O—, —O-phenylene-CH2-phenylene-O—, —Si(CH3)2—, -0-Si(CH3)2—O—, —O—Si(CH3)(0-CH3)—O—, —Si(CH3)(R17)—O—Si(CH3)(R18)—, 5-(2-hydroxyethyl)-[1,3,5]triazinane-2,4,6-trione-1,3-diyl and/or by from one to nine oxygen atoms.
    • 本发明涉及式(I)和(II)的新型酮,其中R 1,R 2,R 3和R 4是例如C 1 -C 8烷基,R 5是例如氢,A是Cl,Br,-O-R 7 ,-NR 8 R 9或-S-R 16,A'为-O-,-NH-或-NR 8 - ,X和Y各自独立地为O-R 10或-N(R 11)(R 12),n为 R 1为例如直链或支链C 2 -C 20烷基的n价基团,其碳链可以被环己二基,亚苯基,-CH(OH) - , - C(C 2 H 5)( CH 2 -CH 2 -OH) - , - C(CH 3)(CH 2 -CH 2 -OH) - , - C(CH 2 -CH 2 OH)2 - , - N(CH 3) - , - N(C 2 H 5) (CH2-CH2-OH) - , - CO-O - , - O-CO-,-P(CH2-CH2-OH) - ,-P(O)(CH2-CH2-OH) (O-CH 2 -CH 2 -OH)-O-,-O-P(O)(O-CH 2 -CH 2 -OH)-O-,-O-环己二基-C(CH 3)2 - 环己烷二基-O-, - O-亚苯基-C(CH 3)2 - 亚苯基-O - , - 亚苯基-CH 2 - 亚苯基-O-,-Si(CH 3)2 - , - O-Si(CH 3)2 -O-,-O- Si(CH 3)(O-CH 3)-O-,-Si(CH 3)(R 17)-O-Si(CH 3)(R 18) - ,5-(2-羟乙基) - [1,3,5] 2,4,6-三酮-1,3-二基和/或1-9个氧原子。
    • 5. 发明授权
    • O-acyloxime photoinitiators
    • O-酰基肟光引发剂
    • US06596445B1
    • 2003-07-22
    • US09338152
    • 1999-06-23
    • Akira MatsumotoHidetaka OkaMasaki OhwaHisatoshi KuraJean-Luc BirbaumKurt Dietliker
    • Akira MatsumotoHidetaka OkaMasaki OhwaHisatoshi KuraJean-Luc BirbaumKurt Dietliker
    • C07C25164
    • C07C251/66B33Y70/00C07C251/68C07C323/47C07D295/135C07D335/18C08F2/50G03F7/0007G03F7/002G03F7/0045G03F7/031G03F7/0388
    • Oximeester compounds of the formulae I, II, III and IV wherein R1 is phenyl, C1-C20alkyl or C2-C20alkyl optionally interrupted by —O—, C2-C20alkanoyl or benzoyl, or R1 is C2-C12alkoxycarbonyl or phenoxycarbonyl; R1′ is C2-C12alkoxycarbonyl, or R1′ is phenoxycarbonyl, or R1′ is —CONR10R11 or CN; R2 is C2-C12alkanoyl, C4-C6alkenoyl, benzoyl, C2-C6alkoxycarbonyl or phenoxycarbonyl; R3, R4, R5, R6 and R7 are hydrogen, halogen, C1-C12alkyl, cyclopentyl, cyclohexyl, phenyl, benzyl, benzoyl, C2-C12alkanoyl, C2-C12alkoxycarbonyl, phenoxycarbonyl or a group OR8, SR9, SOR9, SO2R9 or NR10R11; R4′, R5′ and R6′ are hydrogen, halogen, C1-C12alkyl, cyclopentyl, cyclohexyl, phenyl, benzyl, benzoyl, C2-C12-alkanoyl, C2-C12alkoxycarbonyl, phenoxycarbonyl, or are a group OR8, SR9, SOR9, SO2R9, NR10R11; provided that at least one of R3, R4, R5, R6, R7, R′4, R′5 and R′6 is OR8, SR9 or NR10R11; R8, R9, R10 and R11 are for example hydrogen, C1-C12alkyl, phenyl; are suitable as initiators for the photopolymerization of radically polymerizable compounds.
    • 式I,II,III和IV其中R 1的肟酯化合物是苯基,任选被-O - ,C 2 -C 20烷酰基或苯甲酰基中断的C 1 -C 20烷基或C 2 -C 20烷基,或者R 1是C 2 -C 12烷氧基羰基或苯氧基羰基; R1'是C2-C12烷氧基羰基,或R1'是苯氧基羰基,或R1'是-CONR10R11或CN; R2是C2-C12烷酰基,C4-C6链烯酰基,苯甲酰基,C2-C6烷氧基羰基或苯氧基羰基; R3,R4,R5,R6和R7是氢,卤素,C1-C12烷基,环戊基,环己基,苯基,苄基,苯甲酰基,C2-C12烷酰基,C2-C12烷氧基羰基,苯氧基羰基或OR8,SR9,SOR9,SO2R9或NR10R11; R4',R5'和R6'为氢,卤素,C1-C12烷基,环戊基,环己基,苯基,苄基,苯甲酰基,C2-C12-烷酰基,C2-C12烷氧基羰基,苯氧基羰基,或为OR8,SR9,SOR9,SO2R9 ,NR10R11; 条件是R3,R4,R5,R6,R7,R'4,R'5和R'6中的至少一个是OR8,SR9或NR10R
    • 6. 发明授权
    • Oxime derivatives and the use thereof as latent acids
    • 肟衍生物及其作为潜伏酸的用途
    • US06512020B1
    • 2003-01-28
    • US09820115
    • 2001-03-28
    • Toshikage AsakuraHitoshi YamatoMasaki OhwaJean-Luc BirbaumKurt DietlikerJunichi Tanabe
    • Toshikage AsakuraHitoshi YamatoMasaki OhwaJean-Luc BirbaumKurt DietlikerJunichi Tanabe
    • C08J328
    • G03F7/0045B33Y70/00C07C251/62C07C309/00C07C309/65C07C317/32C07C323/47C07C381/00C07C2602/42C07D319/18C07D333/22
    • Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g. C2-C6haloalkanoyl, or halobenzoyl, R′3 is for example phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, wherein these radicals are unsubstituted or substituted, X is halogen; are especially suitable as photosensitive acid-donors in chemically amplified resist formulations.
    • 式I,II和III的化合物,其中R1是例如氢,C1-C12烷基,C3-C30环烷基,C2-C12链烯基,C4-C8环烯基,苯基,未取代或取代的萘基,蒽基或菲基,未取代或取代的, 未取代或取代的杂芳基; 其中除氢之外的所有基团R1可以另外被具有在酸作用下切割的-O-C键或-O-Si键的基团取代; R'1是例如亚苯基,亚萘基,亚二苯基或氧联二苯基,其中这些基团是未取代的或被取代的; R2是卤素或C1-C10卤代烷基; R3是例如C1-C18烷基磺酰基,苯基磺酰基,萘基磺酰基,蒽磺酰基或菲基磺酰基,其中基团是未取代的或被取代的,或者R3是例如。 C 2 -C 6卤代烷酰基或卤代苯甲酰基,R'3是例如亚苯基二磺酰基,萘基二磺酰基,二苯基二磺酰基或氧基二苯基二磺酰基,其中这些基团是未取代的或被取代的,X是卤素; 在化学放大抗蚀剂配方中特别适合用作光敏酸供体。
    • 8. 发明授权
    • Sulphonium salt initiators
    • 锍盐引发剂
    • US07901867B2
    • 2011-03-08
    • US11922444
    • 2006-06-21
    • Jean-Pierre WolfAttila LatikaJean-Luc BirbaumStephan IlgPascal Hayoz
    • Jean-Pierre WolfAttila LatikaJean-Luc BirbaumStephan IlgPascal Hayoz
    • G03F7/004G03F7/30C07C381/12
    • C07D209/88B33Y70/00C07C309/06C07C381/12G03F7/0045G03F7/038Y10S430/122
    • Compounds of the formula (I), (II), (III), (IV) and wherein, R is hydrogen, C1-C20alkyl; C2-C20alkyl interrupted by one or more O; is -L-X—R2 or -L-R2; R1 has for example one of the meanings as given for R; R2 is a monovalent sensitizer or photoinitiator moiety; Ar1 and Ar2 for example independently of one another are phenyl substituted by C1-C20alkyl, halogen or OR3; or are unsubstituted naphthyl, anthryl, phenanthryl or biphenylyl; or are naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OH or OR3; or are —Ar4-A-Ar3; Ar3 is unsubstituted phenyl naphthyl, anthryl, phenanthryl or biphenylyl; or is phenyl, naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OR3 or benzoyl; Ar4 is phenylene, naphthylene, anthrylene or phenanthrylene; A is a direct bond, S, O or C1-C20alkylene; X is CO, C(O)O, OC(O), O, S or NR3; L is C1-C20alkylene or C2-C20alkylene interrupted by one or more O; R3 is C1-C20alkyl or C1-C20hydroxyalkyl; and Y is an anion, are suitable as photolatent acid generators.
    • 式(I),(II),(III),(IV)的化合物,其中R是氢,C 1 -C 20烷基; 被一个或多个O中断的C 2 -C 20烷基; 是-L-X-R2或-L-R2; R1具有例如R给出的含义之一; R2是单价敏化剂或光引发剂部分; Ar 1和Ar 2例如彼此独立地是被C 1 -C 20烷基,卤素或OR 3取代的苯基; 或未取代的萘基,蒽基,菲基或联苯基; 或被C 1 -C 20烷基,OH或OR 3取代的萘基,蒽基,菲基或联苯基; 或为-Ar4-A-Ar3; Ar 3是未取代的苯基萘基,蒽基,菲基或联苯基; 或由C 1 -C 20烷基,OR 3或苯甲酰基取代的苯基,萘基,蒽基,菲基或联苯基; Ar4是亚苯基,亚萘基,亚蒽基或菲基; A是直接键合,S,O或C1-C20亚烷基; X是CO,C(O)O,OC(O),O,S或NR 3; L是被一个或多个O中断的C 1 -C 20亚烷基或C 2 -C 20亚烷基; R3是C1-C20烷基或C1-C20羟烷基; 并且Y是阴离子,适合作为光潜酸产生剂。
    • 9. 发明授权
    • Oxime derivatives and the use thereof as latent acids
    • 肟衍生物及其作为潜伏酸的用途
    • US06261738B1
    • 2001-07-17
    • US09533952
    • 2000-03-23
    • Toshikage AsakuraHitoshi YamatoMasaki OhwaJean-Luc BirbaumKurt DietlikerJunichi Tanabe
    • Toshikage AsakuraHitoshi YamatoMasaki OhwaJean-Luc BirbaumKurt DietlikerJunichi Tanabe
    • G03G7004
    • G03F7/039C07C251/62C07C309/00C07C309/65C07C317/32C07C323/47C07C381/00C07C2602/42C07D319/18C07D333/22G03F7/0045Y10S430/12
    • Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g. C2-C6haloalkanoyl, or halobenzoyl, R′3 is for example phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, wherein these radicals are unsubstituted or substituted, X is halogen; are especially suitable as phototsensitive acid-donors in chemically amplified resist formulations.
    • 式I,II和III的化合物,其中R1是例如氢,C1-C12烷基,C3-C30环烷基,C2-C12链烯基,C4-C8环烯基,苯基,未取代或取代的萘基,蒽基或菲基,未取代或取代的, 未取代或取代的杂芳基; 其中除氢之外的所有基团R1可以另外被具有在酸作用下切割的-O-C键或-O-Si键的基团取代; R'1是例如亚苯基,亚萘基,亚二苯基或氧联二苯基,其中这些基团是未取代的或被取代的; R2是卤素或C1-C10卤代烷基; R3是例如C1-C18烷基磺酰基,苯基磺酰基,萘基磺酰基,蒽磺酰基或菲基磺酰基,其中基团是未取代的或被取代的,或者R3是例如。 C 2 -C 6卤代烷酰基或卤代苯甲酰基,R'3是例如亚苯基二磺酰基,萘基二磺酰基,二苯基二磺酰基或氧基二苯基二磺酰基,其中这些基团是未取代的或被取代的,X是卤素; 在化学放大抗蚀剂配方中特别适合作为光敏酸供体。
    • 10. 发明申请
    • Sulphonium Salt Initiators
    • 锍盐引发剂
    • US20090208872A1
    • 2009-08-20
    • US11922444
    • 2006-06-21
    • Jean-Pierre WolfAttila LatikaJean-Luc BirbaumStephan IlgPascal Hayoz
    • Jean-Pierre WolfAttila LatikaJean-Luc BirbaumStephan IlgPascal Hayoz
    • G03F7/20G03F7/004C07D209/88C07C321/30
    • C07D209/88B33Y70/00C07C309/06C07C381/12G03F7/0045G03F7/038Y10S430/122
    • Compounds of the formula (I), (II), (III), (IV) and wherein, R is hydrogen, C1-C20alkyl; C2-C20alkyl interrupted by one or more O; is -L-X—R2 or -L-R2; R1 has for example one of the meanings as given for R; R2 is a monovalent sensitizer or photoinitiator moiety; Ar1 and Ar2 for example independently of one another are phenyl substituted by C1-C20alkyl, halogen or OR3; or are unsubstituted naphthyl, anthryl, phenanthryl or biphenylyl; or are naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OH or OR3; or are —Ar4-A-Ar3; Ar3 is unsubstituted phenyl naphthyl, anthryl, phenanthryl or biphenylyl; or is phenyl, naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OR3 or benzoyl; Ar4 is phenylene, naphthylene, anthrylene or phenanthrylene; A is a direct bond, S, O or C1-C20alkylene; X is CO, C(O)O, OC(O), O, S or NR3; L is C1-C20alkylene or C2-C20alkylene interrupted by one or more O; R3 is C1-C20alkyl or C1-C20hydroxyalkyl; and Y is an anion, are suitable as photolatent acid generators.
    • 式(I),(II),(III),(IV)的化合物,其中R是氢,C 1 -C 20烷基; 被一个或多个O中断的C 2 -C 20烷基; 是-L-X-R2或-L-R2; R1具有例如R给出的含义之一; R2是单价敏化剂或光引发剂部分; Ar 1和Ar 2例如彼此独立地是被C 1 -C 20烷基,卤素或OR 3取代的苯基; 或未取代的萘基,蒽基,菲基或联苯基; 或被C 1 -C 20烷基,OH或OR 3取代的萘基,蒽基,菲基或联苯基; 或为-Ar4-A-Ar3; Ar 3是未取代的苯基萘基,蒽基,菲基或联苯基; 或由C 1 -C 20烷基,OR 3或苯甲酰基取代的苯基,萘基,蒽基,菲基或联苯基; Ar4是亚苯基,亚萘基,亚蒽基或菲基; A是直接键合,S,O或C1-C20亚烷基; X是CO,C(O)O,OC(O),O,S或NR 3; L是被一个或多个O中断的C1-C20亚烷基或C2-C20亚烷基; R3是C1-C20烷基或C1-C20羟烷基; 并且Y是阴离子,适合作为光潜酸产生剂。