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    • 1. 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
    • Photopolymerizable thermosetting resin compositions
    • 光聚合性热固性树脂组合物
    • US06485885B1
    • 2002-11-26
    • US09720441
    • 2000-12-22
    • Hidetaka OkaMasaki OhwaAkira MatsumotoHisatoshi Kura
    • Hidetaka OkaMasaki OhwaAkira MatsumotoHisatoshi Kura
    • G03F7004
    • G03F7/031G03F7/038
    • Compositions comprising (A) an oligomer or polymer containing at least one carboxylic acid group in the molecule; (B) at least one compound of formulas (I, II, III, IV, V or VI), wherein R1 inter alia is phenyl or alkyl; R2 is for example C2-C12alkonoyl which is unsubstituted or substituted or is benzoyl; R3, R4, R5, R6 and R7 independently of one another are for instance hydrogen, C1-C12alkyl, cyclohexyl or phenyl which is unsubstituted or substituted, or are benzyl, benzoyl, C2-C12alkanoyl or phenoxycarbonyl; R8 is for example hydrogen or C1-C12alkyl or a group (B); M is for example C1-C12alkylene, cyclohexylene or phenylene; M1 inter alia is a direct bond or C1-C12alkylenoxy; and Ar is a 5- or 6-membered aromatic heterocyclic ring; (C) a photopolymerizable reactive or unreactive diluent; and (D) as a thermosetting component an epoxy compound containing at least two epoxy groups in one molecule; are highly suitable as resists which are alkaline developable.
    • 包含(A)在分子中含有至少一个羧酸基团的低聚物或聚合物的组合物; (B)至少一种式(I,II,III,IV,V或VI)化合物,其中R 1特别是苯基或烷基; R2是例如未取代或取代的C 2 -C 12烷氧基或苯甲酰基; R 3,R 4,R 5,R 6和R 7彼此独立地是例如氢,C 1 -C 12烷基,环己基或未取代或取代的苯基,或者是苄基,苯甲酰基,C 2 -C 12烷酰基或苯氧基羰基; R8是例如氢或C1-C12烷基或基团(B); M为例如C 1 -C 12亚烷基,亚环己基或亚苯基; M1特别是直接键或C1-C12亚烷基氧基; 且Ar为5-或6-元芳族杂环; (C)可光聚合反应性或非活性稀释剂; 和(D)作为热固性组分在一个分子中含有至少两个环氧基团的环氧化合物; 非常适合作为碱性显影的抗蚀剂。
    • 7. 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
    • 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。
    • 9. 发明授权
    • Oxime derivatives and the use thereof as photoinitiators
    • 肟衍生物及其作为光引发剂的用途
    • US06806024B1
    • 2004-10-19
    • US09914433
    • 2001-08-27
    • Hisatoshi KuraHitoshi YamatoMasaki OhwaKurt Dietliker
    • Hisatoshi KuraHitoshi YamatoMasaki OhwaKurt Dietliker
    • G03F7004
    • G03F7/031B33Y70/00C07C309/66C07C309/73C07C323/57C07C381/00C07D307/66C07D333/36C07D339/08C07F9/097C07F9/655345C08F2/50Y10S430/12Y10S430/123
    • Radically photopolymerizable compositions comprising (a) at least one ethylenically unsaturated photopolymerizable compound; (b) as photoinitiator, at least one compound of formulae (I, II, III, IV, V and/or VI), wherein m is 0 or 1; n is 0, 1, 2 or 3; x is 1 or 2; R1 is inter alia phenyl, naphthyl, anthracyl or phenanthryl, a heteroaryl radical, C2-C12alkenyl, C4-C8cycloalkenyl, or C6-C12bicycloalkenyl; R′1 is inter alia C2-C12alkylene, or phenylene; R2 has one of the meanings of R1 or inter alia is phenyl; y is 1 or 2; R3 if x is 1 inter alia is C1-C18alkylsulfonyl, or phenyl-C1-C3alkylsulfonyl, R3 if x is 2, is for example C2-C12alkylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, or C1-C8alkyl; R6, R7, R8 inter alia are hydrogen, R26Y—, or phenyl; R9 inter alia is C5-C8cycloalkyl, or phenyl; A is for example —S—, —O—, or —NR10—; Q is C1-C8-alkylene optionally interrupted by —O—; X is —O— or —NR9—; R10 inter alia is hydrogen, or phenyl; and (c) at least one coinitiator; are especially suitable for the preparation of color filter systems.
    • 自由基光聚合组合物,其包含(a)至少一种烯属不饱和光聚合化合物; (b)作为光引发剂,至少一种式(I,II,III,IV,V和/或VI)的化合物,其中m为0或1; n为0,1,2或3; x为1或2; R 1特别是苯基,萘基,蒽基或菲基,杂芳基,C 2 -C 12烯基,C 4 -C 8环烯基或C 6 -C 12双环烯基; R'1特别是C 2 -C 12亚烷基或亚苯基; R2具有R 1的含义之一,尤其是苯基; y为1或2; 如果x是1,则R3如果是C 1 -C 18烷基磺酰基,或苯基-C 1 -C 3烷基磺酰基,如果x是2,则R 3是例如C 2 -C 12亚烷基二磺酰基; R4和R5尤其是氢,卤素或C1-C8烷基; R6,R7,R8特别是氢,R26Y-或苯基; R9尤其是C5-C8环烷基或苯基; A是例如-S-,-O-或-NR 10 - ; Q是任选被-O-间隔的C1-C8-亚烷基; X是-O-或-NR 9 - ; R 10尤其是氢或苯基; 和(c)至少一种共引发剂; 特别适用于制备滤色器系统。
    • 10. 发明授权
    • Photosensitive resin composition
    • 感光树脂组合物
    • US07829257B2
    • 2010-11-09
    • US09734635
    • 2000-12-12
    • Hidetaka OkaKazuhiko KunimotoHisatoshi KuraMasaki OhwaJunichi Tanabe
    • Hidetaka OkaKazuhiko KunimotoHisatoshi KuraMasaki OhwaJunichi Tanabe
    • G03C1/00
    • C08F2/50G03F7/031
    • Photosensitive compositions comprising (A) an alkali soluble compound; (B) at least one compound, of formula I or II wherein R1 inter alia is C4-C9cycloalkanoyl, C3-C12alkenoyl, or benzoyl which is unsubstituted or substituted; Ar1 is either C6-C20aryl or C6-C20aryloyl each of which is unsubstituted or substituted; x is 2 or 3; M1 when x is 2, inter alia is a group phenylene or naphthylene, each of which optionally is substituted i.a. by OR3, SR4 or NR5R6; or M1, when x is 3, is a trivalent group, optionally substituted; R3 is for example hydrogen or C1-C12alkyl; C2-C6alkyl which is for example substituted by —OH, —SH, —CN, C3-C6alkenoxy, or —OCH2CH2CN; R4 is for example hydrogen, C1-C12alkyl, C3-C12alkenyl, cyclohexyl, or phenyl which is unsubstituted or substituted; R5 and R6 independently of each other inter alia are hydrogen, C1-C12alkyl, C2-C4hydroxyalkyl, C2-C10alkoxyalkyl, C3-C5alkenyl, C3-C8cycloalkyl, phenyl-C1-C3alkyl, C1-C4alkanoyl, C3-C6alkenoyl, benzoyl or phenyl which is unsubstituted or substituted; and (C) a photopolymerizable compound; exhibit an unexpectedly good performance, in particular in photoresist technology.
    • 光敏组合物,其包含(A)碱溶性化合物; (B)至少一种式I或II的化合物,其中R 1特别是C 4 -C 9环烷酰基,C 3 -C 12烯酰基或未取代或取代的苯甲酰基; Ar 1是C 6 -C 20芳基或C 6 -C 20芳酰基,其各自为未取代或取代的; x为2或3; M1当x为2时,特别是亚苯基或亚萘基,其各自任选被取代。 由OR3,SR4或NR5R6; 或M1,当x为3时,为任选取代的三价基团; R3是例如氢或C1-C12烷基; 例如被-OH,-SH,-CN,C 3 -C 6烯氧基或-OCH 2 CH 2 CN取代的C 2 -C 6烷基; R4是例如氢,C1-C12烷基,C3-C12链烯基,环己基或未取代或取代的苯基; R 5和R 6彼此独立地尤其是氢,C 1 -C 12烷基,C 2 -C 4羟烷基,C 2 -C 10烷氧基烷基,C 3 -C 5烯基,C 3 -C 8环烷基,苯基-C 1 -C 3烷基,C 1 -C 4烷酰基,C 3 -C 6烯酰基,苯甲酰基或苯基 未取代或取代; 和(C)可光聚合化合物; 表现出意想不到的良好性能,特别是在光刻胶技术中。