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    • 1. 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。
    • 3. 发明授权
    • Unsaturated oxime derivatives and the use thereof as latent acids
    • 不饱和肟衍生物及其作为潜伏酸的用途
    • US06703182B1
    • 2004-03-09
    • US09763016
    • 2001-02-15
    • Jean-Luc BirbaumToshikage AsakuraHitoshi Yamato
    • Jean-Luc BirbaumToshikage AsakuraHitoshi Yamato
    • G03C1492
    • C09D11/38B33Y70/00C07C309/66C07C309/73C07C381/00C09D11/03C09D11/101G03F7/0045Y10S430/12Y10S430/122
    • Compounds of formulae I, II or III wherein m is zero or 1; n is 1, 2 or 3; R1 inter alia is unsubstituted or substituted phenyl, or naphthyl, anthracyl, phenanthryl, a heteroaryl radical, or C2-C12alkenyl; R′1 inter alia is vinylene, phenylene, naphthylene, diphenylene or oxydiphenylene; R2 inter alia is CN, C1-C4haloalkyl, C2-C6alkoxycarbonyl, phenoxycarbonyl, or benzoyl; R3 inter alia is C1-C18alkylsulfonyl, phenyl-C1-C3alkylsulfonyl, camphorylsulfonyl, or phenylsulfonyl; R′3 inter alia is C2-C12alkylenedisulfonyl, phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, C1-C8alkyl, C1-C6alkoxy, C1-C4haloalkyl, CN, NO2, C2-C6alkanoyl, benzoyl, phenyl, —S-phenyl, OR6, SR9, NR7R8, C2-C6alkoxycarbonyl or phenoxycarbonyl; R6 inter alia is hydrogen, phenyl or C1-C12alkyl; R7 and R8 inter alia are hydrogen or C1-C12alkyl; R9 inter alia is C1-C12 alkyl; R10, R11 and R12 inter alia are C1-C6alkyl or phenyl; upon irradiation react as acid generating compounds and thus are suitable in photoresist applications.
    • 其中m为式I,II或III的化合物为0或1; n为1,2或3; R 1特别是未取代或取代的苯基,或萘基,蒽基,菲基,杂芳基或C 2 -C 12烯基; 尤其是亚乙烯基,亚苯基,亚萘基,二亚苯基或氧联二苯基; R2特别是CN,C 1 -C 4卤代烷基,C 2 -C 6烷氧基羰基,苯氧基羰基或苯甲酰基; R3特别是C 1 -C 18烷基磺酰基,苯基-C 1 -C 3烷基磺酰基,樟脑磺酰基或苯基磺酰基; R'3特别是C 2 -C 12亚烷基二磺酰基,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; R4和R5特别是氢,卤素,C1-C8烷基,C1-C6烷氧基,C1-C4卤代烷基,CN,NO2,C2-C6烷酰基,苯甲酰基,苯基,-S-苯基,OR6,SR9,NR7R8,C2-C6烷氧基羰基或苯氧基羰基 ; R6尤其是氢,苯基或C 1 -C 12烷基; R 7和R 8尤其是氢或C 1 -C 12烷基; R9尤其是C1-C12烷基; R 10,R 11和R 12特别是C 1 -C 6烷基或苯基; 在照射时作为产生酸的化合物反应,因此适用于光刻胶应用。
    • 5. 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。
    • 6. 发明授权
    • Iodonium salts as latent acid donors
    • 碘盐作为潜酸供体
    • US06306555B1
    • 2001-10-23
    • US09740205
    • 2000-12-18
    • Reinhard SchulzJean-Luc BirbaumJean-Pierre WolfStephan IlgHitoshi YamatoToshikage Asakura
    • Reinhard SchulzJean-Luc BirbaumJean-Pierre WolfStephan IlgHitoshi YamatoToshikage Asakura
    • G03F7004
    • G03F7/0382B33Y70/00C07C17/00C07C25/18C07C2601/14C08G59/68C08G65/105G03F7/0045G03F7/038G03F7/0392Y10S430/115
    • Radiation-sensitive compositions comprising (a1) a cationically or acid-catalytically polymerisable or crosslinkable compound or (a2) a compound that increases its solubility in a developer under the action of acid; and (b) at least one diaryliodonium salt of formula I X is branched C3-C20alkyl or C3-C8cycloalkyl; X1 is hydrogen, linear C1-C20alkyl, branched C3-C20alkyl or C3-C8cycloalkyl; with the proviso that the sum of the carbon atoms in X and X1 is at least 4; Y is linear C1-C10alkyl, branched C3-C10alkyl or C3-C8cycloalkyl; A− is a non-nucleophilic anion, selected from the group (BF4)−, (SbF6)−, (PF6)−, (B(C6F5))4−, C1-C20alkylsulfonate, C2-C20haloalkylsulfonate, unsubstituted C6-C10arylsulfonate, camphorsulfonate, and C6-C10arylsulfonate substituted by halogen, NO2, C1-C12alkyl, C1-C12halo-alkyl, C1-C12alkoxy or by COOR1; and R1 is C1-C20alkyl, phenyl, benzyl; or phenyl mono- or poly-substituted by C1-C12alkyl, C1-C12alkoxy or by halogen; with the proviso that the two phenyl rings on the iodine atom are not identically substituted.
    • 辐射敏感性组合物,其包含(a1)阳离子或酸可催化聚合或交联的化合物或(a2)在酸的作用下增加其在显影剂中的溶解度的化合物; 和(b)式IX的至少一种二芳基碘鎓盐是支链C 3 -C 20烷基或C 3 -C 8环烷基; X 1是氢,直链C 1 -C 20烷基,支链C 3 -C 20烷基或C 3 -C 8环烷基; 条件是X和X 1中的碳原子总数至少为4; Y为直链C 1 -C 10烷基,支链C 3 -C 10烷基或C 3 -C 8环烷基; A-为非亲核阴离子,选自(BF 4 ) - ,(SbF 6) - ,(PF 6) - ,(B(C 6 F 5))4-,C 1 -C 20烷基磺酸酯,C 2 -C 20卤代烷基磺酸酯,未取代的C 6 -C 10芳基磺酸酯,樟脑磺酸酯和C 6 -C 10芳基磺酸酯,被卤素, ,C 1 -C 12卤代烷基,C 1 -C 12烷氧基或COOR 1; 并且R 1是C 1 -C 20烷基,苯基,苄基; 或被C 1 -C 12烷基,C 1 -C 12烷氧基或卤素单取代或多取代的苯基;条件是碘原子上的两个苯环不同等取代。
    • 8. 发明申请
    • SULFONIUM DERIVATIVES AND THE USE THEROF AS LATENT ACIDS
    • 磺胺衍生物及其作为酸性物质的用途
    • US20110171569A1
    • 2011-07-14
    • US12996795
    • 2009-06-02
    • Yuichi NishimaeToshikage AsakuraHitoshi Yamato
    • Yuichi NishimaeToshikage AsakuraHitoshi Yamato
    • G03F7/004C07D335/08C07D339/08C07D413/02C07D285/16C07D327/08C08F228/06G03F7/20G03F1/00
    • C07D339/08C07D327/08
    • Compounds of the formula (I), wherein R1, R2 and R3 for example are hydrogen, halogen, CN, C1-C18alkyl, C1-C10 haloalkyl, (CO)R8, (CO)OR4, or (CO)NR5R6; Y is O, S or CO; D2, D3 and D4 for example are a direct bond, O, S, NR7, CO, O(CO), (CO)O, S(CO), (CO)S, NR7(CO), (CO)NR7, SO, SO2, or OSO2, C1-C18alkylene, C3-C30cycloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, Ar1; Ar1, Ar2 and Ar3 are for example phenylene, R4, R5, R6, R7 and R8 are for example hydrogen, C3-C30-cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1C3-alkyl; X− is Formulae (IA), (IB) or (IC); R10 is for example C1-C18alkyl, C1-C10haloalkyl, camphoryl, phenyl-C1-C3alkyl, C3-C30cycloalkyl; and R11, R12, R13, R14 and R15 are for example C1-C10haloalkyl; are useful as polymerizable photolatent acids.
    • 式(I)化合物,其中R1,R2和R3例如是氢,卤素,CN,C1-C18烷基,C1-C10卤代烷基,(CO)R8,(CO)OR4或(CO)NR5R6; Y为O,S或CO; D2,D3和D4例如是直接键合,O,S,NR7,CO,O(CO),(CO)O,S(CO),(CO)S,NR7(CO) SO,SO 2或OSO 2,C 1 -C 18亚烷基,C 3 -C 30亚环烷基,C 2 -C 12亚烯基,C 4 -C 30环亚烯基,Ar 1; Ar 1,Ar 2和Ar 3是例如亚苯基,R 4,R 5,R 6,R 7和R 8是例如氢,C 3 -C 30 - 环烷基,C 1 -C 18烷基,C 1 -C 10卤代烷基,C 2 -C 12烯基,C 4 -C 30环烯基,苯基-C 1 -C 3 - 烷基; X-是式(IA),(IB)或(IC); R 10例如为C 1 -C 18烷基,C 1 -C 10卤代烷基,樟脑基,苯基-C 1 -C 3烷基,C 3 -C 30环烷基; R 11,R 12,R 13,R 14和R 15例如为C 1 -C 10卤代烷基; 可用作可聚合的光潜酸。