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    • 4. 发明授权
    • Oxime derivatives and use thereof as latent acids
    • 肟衍生物及其用作潜伏酸
    • US07687220B2
    • 2010-03-30
    • US11632687
    • 2005-07-11
    • Hitoshi YamatoToshikage AsakuraTobias Hintermann
    • Hitoshi YamatoToshikage AsakuraTobias Hintermann
    • G03F7/028C07C259/08
    • C07C309/67B33Y70/00C07C309/65C07C309/73C07C309/74C07C309/75C07C381/00C07C2603/18C07C2603/20C07C2603/66C07D209/86C07F9/097G03F7/0007G03F7/0045G03F7/0382G03F7/0392Y10S430/12
    • The invention pertain to novel photoacid generator compounds of the formula I, II or III wherein R1 is for example C1-C18alkylsulfonyl or phenylsulfonyl, phenyl-C1-C3alkylsulfonyl, , naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, all optionally substituted, or R1 is a group X1, X2 and X3 independently of each other are O or S; R′1, is e.g. phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, all optionally substituted; R2 is halogen or C1-C10haloalkyl; X is halogen; Ar1 is for example biphenylyl or fluorenyl, or is substituted naphthyl; Ar′1 is heteroarylene, optionally substituted; R8, R9, R10 and R11 for example are C1-C6alkyl which is unsubstituted or substituted by halogen; or R8, R9 and R10 are phenyl which is unsubstituted or substituted by C1-C4alkyl or halogen; or R10 and R11 together are 1,2-phenylene or C2-C6alkylene which is unsubstituted or substituted by C1-C4alkyl or halogen.
    • 本发明涉及式I,II或III的新型光致酸产生剂化合物,其中R 1为例如C 1 -C 18烷基磺酰基或苯基磺酰基,苯基-C 1 -C 3烷基磺酰基,萘基磺酰基,蒽磺酰基或菲基磺酰基,均为任选取代的,或者R 1为基团X 1 ,X2和X3彼此独立地为O或S; R'1,例如 亚苯基二磺酰基,亚苯基二磺酰基,二苯基二磺酰基或氧基二苯基二磺酰基,全部任选被取代; R2是卤素或C1-C10卤代烷基; X是卤素; Ar1为例如联苯基或芴基,或为取代的萘基; Ar'1是杂亚芳基,任选取代; R8,R9,R10和R11例如是未被取代或被卤素取代的C1-C6烷基; 或R 8,R 9和R 10为未被取代或被C 1 -C 4烷基或卤素取代的苯基; 或R 10和R 11一起是1,2-亚苯基或未被取代或被C 1 -C 4烷基或卤素取代的C 2 -C 6亚烷基。
    • 7. 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。
    • 10. 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。