Unsaturated oxime derivatives and the use thereof as latent acids
    1.
    发明授权
    Unsaturated oxime derivatives and the use thereof as latent acids 有权
    不饱和肟衍生物及其作为潜伏酸的用途

    公开(公告)号:US06703182B1

    公开(公告)日:2004-03-09

    申请号:US09763016

    申请日:2001-02-15

    IPC分类号: G03C1492

    摘要: 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.

    摘要翻译: 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。

    Photoinitiators having chain transfer groups polymerized to obtain macrophotoinitiators useful to give block copolymers
    2.
    发明授权
    Photoinitiators having chain transfer groups polymerized to obtain macrophotoinitiators useful to give block copolymers 失效
    具有链转移基团的光引发剂被聚合以获得可用于产生嵌段共聚物的大分子引发剂

    公开(公告)号:US06458864B1

    公开(公告)日:2002-10-01

    申请号:US09701457

    申请日:2000-11-27

    IPC分类号: C08F250

    摘要: Compounds with chain transfer groups of the formula I, II, III and IV wherein a is 1 or 2; Ar and Ar1 inter alia are phenyl; Ar2 inter alia is phenylene, these groups being unsubstituted or substituted; X is a direct bond, —O—, —S— or —N(R6)—; Y inter alia is hydrogen or C1-C12alkyl; M1 is —NR3R4 or —OH, or M1 is Ar when R1 and R2 are alkoxy, or aryloxy; R1 and R2 independently of one another e.g. are C1-C8alkyl; R3 and R4 for example are C1-C12alkyl, or together are C3-C7alkylene; R5 inter alia is C1-C6alkylene or a direct bond; R6 is for example hydrogen; and Z is a divalent radical, provided that at least one of the radicals Ar, Ar1, Ar2, R1, R2, R3, R4, R5 or Y is substituted by SH groups; are suitable for the thermal preparation of macrophotoinitiators which are polymerized photochemically to give block-copolymers.

    摘要翻译: 具有式I,II,III和IV的链转移基团的化合物是1或2; Ar和Ar1特别是苯基; Ar2特别是亚苯基,这些基团是未取代的或取代的; X是直接键,-O - , - S-或-N(R6) - ; Y尤其是氢或C 1 -C 12烷基; 当R1和R2为烷氧基时,M1为-NR3R4或-OH,或M1为Ar,或为芳氧基; R1和R2彼此独立地例如。 是C 1 -C 8烷基; R 3和R 4例如是C 1 -C 12烷基,或一起是C 3 -C 7亚烷基; R5尤其是C1-C6亚烷基或直接键; R6是例如氢; 并且Z是二价基团,条件是基团Ar,Ar 1,Ar 2,R 1,R 2,R 3,R 4,R 5或Y中的至少一个被SH基取代;适用于光化学聚合的高分子引发剂的热制备 得到嵌段共聚物。

    Oxime sulfonates and the use thereof as latent sulfonic acids
    3.
    发明授权
    Oxime sulfonates and the use thereof as latent sulfonic acids 失效
    肟磺酸盐及其作为潜在磺酸的用途

    公开(公告)号:US6004724A

    公开(公告)日:1999-12-21

    申请号:US104676

    申请日:1998-06-25

    摘要: New oximsulfonate compounds of the formulae I or II, ##STR1## wherein m is 0 or 1; x is 1 or 2; R.sub.1 is, for example phenyl, which is unsubstituted or substituted or R.sub.1 is a heteroaryl radical that is unsubstituted or substituted, or, if m is 0, R.sub.1 additionally is C.sub.2 -C.sub.6 alkoxycarbonyl, phenoxycarbonyl or CN; R'.sub.1 is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.2 has for example one of the meanings of R.sub.1 ; n is 1 or 2; R.sub.3 is for example C.sub.1 -C.sub.18 alkyl, R'.sub.3 when x is 1, has one of the meanings given for R.sub.3, or R'.sub.3 in the formula IV and when x is 2 in the formula 1, is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.4 and R.sub.5 are independently of each other for example hydrogen, halogen, C.sub.1 -C.sub.6 alkyl; R.sub.6 is for example hydrogen, phenyl; R.sub.7 and R.sub.8 are independently of each other for example hydrogen or C.sub.1 -C.sub.12 -alkyl; R.sub.9 is for example C.sub.1 -C.sub.12 alkyl; A is S, O, NR.sub.6, or a group of formula A1, A2, A3 or A4 ##STR2## R.sub.10 and R.sub.11 independently of each other have one of the meanings given for R.sub.4 ; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of one another are for example hydrogen, C.sub.1 -C.sub.4 alkyl; Z is CR.sub.11 or N; Z.sub.1 is --CH.sub.2 --, S, O or NR.sub.6, are useful as latent sulfonic acids, especially in photoresist applications.

    摘要翻译: 式I或II的新的磺酸磺酸酯化合物,其中m为0或1; x为1或2; R1是例如未取代或取代的苯基,或R1是未取代或取代的杂芳基,或者如果m是0,则R1另外是C 2 -C 6烷氧基羰基,苯氧基羰基或CN; R'1例如为C 2 -C 12亚烷基,亚苯基; R2具有例如R1的含义之一; n为1或2; R3为例如C1-C18烷基,当x为1时为R'3,具有R3给出的含义之一,或式Ⅳ中的R'3,当式Ⅺ中x为2时,为例如C 2 -C 12亚烷基, 亚苯基; R4和R5彼此独立,例如氢,卤素,C1-C6烷基; R6是例如氢,苯基; R 7和R 8彼此独立地为氢或C 1 -C 12 - 烷基; R 9为例如C 1 -C 12烷基; A是S,O,NR6或式A1,A2,A3或A4的基团,R10和R11彼此独立地具有对R4给出的含义之一; R 12,R 13,R 14和R 15彼此独立地是例如氢,C 1 -C 4烷基; Z为CR11或N; Z1是-CH2-,S,O或NR6,可用作潜在的磺酸,特别是在光刻胶应用中。

    Latent acids and their use
    4.
    发明申请
    Latent acids and their use 有权
    潜在酸及其用途

    公开(公告)号:US20110217654A1

    公开(公告)日:2011-09-08

    申请号:US13028323

    申请日:2011-02-16

    摘要: The invention pertains to a compound generating an acid of the formula I or II, for instance corresponding sulfonium and iodonium salts, as well as corresponding sulfonyloximes wherein X is CH2 or CO; Y is O, NR4, S, O(CO), O(CO)O, O(CO)NR4, OSO2, O(CS), or O(CS)NR4; R1 is for example C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, interrupted C2-C18alkyl, interrupted C3-C30cycloalkyl, interrupted C3-C30cycloalkyl-C1-C18alkyl, interrupted C4-C30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or heteroaryl, all unsubstituted or are substituted; or R1 is NR12R13; R2 and R3 are for example C3-C30cycloalkylene, C3-C30cycloalkyl-C1-C18alkylene, C1-C18alkylene, C1-C10haloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or heteroarylene; all unsubstituted or substituted; R4 is for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl; R12 and R13 are for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, Ar, (CO)R15, (CO)OR15 or SO2R15; and Ar is phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl or heteroaryl, all unsubstituted or substituted.

    摘要翻译: 本发明涉及产生式I或II的酸的化合物,例如相应的锍盐和碘鎓盐,以及其中X是CH 2或CO的相应的磺酰肟; Y是O,NR4,S,O(CO),O(CO)O,O(CO)NR4,OSO2,O(CS)或O(CS)NR4; R 1是例如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,C 3 -C 30环烷基,C 3 -C 30环烷基-C 1 -C 18烷基,间断的C 2 -C 18烷基,间断的C 3 -C 30环烷基, 间断的C 3 -C 30环烷基-C 1 -C 18烷基,间断的C 4 -C 30环烯基,苯基,萘基,蒽基,菲基,联苯基,芴基或杂芳基,全部未取代或被取代; 或R1是NR12R13; R2和R3是例如C 3 -C 30亚环烷基,C 3 -C 30环烷基-C 1 -C 18亚烷基,C 1 -C 18亚烷基,C 1 -C 10卤代亚烷基,C 2 -C 12亚烯基,C 4 -C 30亚环烯基,亚苯基,亚萘基,亚蒽基,亚菲基,亚联苯基或亚杂芳基。 全部未取代或取代; R4是例如C 3 -C 30环烷基,C 3 -C 30环烷基-C 1 -C 18烷基,C 1 -C 18烷基,C 1 -C 10卤代烷基,C 2 -C 12链烯基,C 4 -C 30环烯基,苯基-C 1 -C 3烷基; R 12和R 13例如为C 3 -C 30环烷基,C 3 -C 30环烷基-C 1 -C 18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,Ar,(CO)R 15 CO)OR15或SO2R15; 并且Ar是苯基,联苯基,芴基,萘基,蒽基,菲基或杂芳基,全部是未取代或取代的。

    Oxime derivatives and use thereof as latent acids
    5.
    发明授权
    Oxime derivatives and use thereof as latent acids 有权
    肟衍生物及其用作潜伏酸

    公开(公告)号:US07687220B2

    公开(公告)日:2010-03-30

    申请号:US11632687

    申请日:2005-07-11

    IPC分类号: G03F7/028 C07C259/08

    摘要: 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.

    摘要翻译: 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。

    Sulfonate derivatives and the use thereof as latent acids

    公开(公告)号:US20080286693A1

    公开(公告)日:2008-11-20

    申请号:US11999116

    申请日:2007-12-04

    IPC分类号: G03F7/20

    摘要: Chemically amplified photoresist compositions comprising,(a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and (b) a compound of the formula Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, Vb or VIa wherein n is 1 or 2; m is 0 or 1; X0 is —[CH2]h—X or —CH═CH2; h is 2, 3, 4, 5 or 6; R1, when n is 1, is for example optionally substituted phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl; R1, when n is 2, is for example optionally substituted phenylene or naphthylene; R2 for example has one of the meanings of R1; X is for example —OR20, —NR21R22, —SR23; X′ is —X1-A3-X-; X1 and X2 are for example —O—, —S— or a direct bond; A3 is e.g. phenylene; R3 has for example one of the meanings given for R1; R4 has for example one of the meaning given for R2; R5 and R6 e.g. are hydrogen; G i.a. is —S— or —O—; R7 when n is 1, e.g. is phenyl, optionally substituted, when n is 2, is for example phenylene; R8 and R9 e.g. are C1-C18alkyl; R10 has one of the meanings given for R7; R11 i.a. is C1-C18alkyl; R12, R13, R14, R15 R16, R17 and R18 for example are hydrogen or C1-C18alkyl; R20, R21, R22 and R23 i.a. are phenyl or C1-C18alkyl; give high resolution with good resist profile.

    Halogenated oxime derivatives and the use thereof
    7.
    发明授权
    Halogenated oxime derivatives and the use thereof 有权
    卤代肟衍生物及其用途

    公开(公告)号:US07399577B2

    公开(公告)日:2008-07-15

    申请号:US10543429

    申请日:2004-02-09

    摘要: Compounds of the formula (I) or (II) wherein R1 is C1-C10haloalkylsulfonyl, halobenzenesulfonyl, C2- C10haloalkanoyl, halobenzoyl; R2 is halogen or C1-C10 haloalkyl; Arl is phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl, all of which are optionally substituted; Ar′1 is for example phenylene, naphthylene, diphonylene, heteroarylene, oxydiphenylene, phenyleneD-D1-D-phenylene or —Ar′1-A1—Y1-A1—Ar′1—; wherein these radicals optionally are substituted; Ae′, is phenylene, naphthylene, anthracylene, phenanthrylene, or heteroarylene, all optionally substituted; A, is for example a direct bond, —0—, —S—, or —NR6—; Y, inter alia is C1-C18alkylene; X is halogen; D is for example —0—, —S— or —NR6—; D, inter alia is C1-C18alkylene; are particularly suitable as photolatent acids in ArF resist technology.

    摘要翻译: 式(I)或(II)的化合物,其中R 1是C 1 -C 10卤代烷基磺酰基,卤代苯磺酰基,C 2 卤代烷酰基,卤代苯甲酰基, R 2是卤素或C 1 -C 10卤代烷基; Ar1是苯基,联苯基,芴基,萘基,蒽基,菲基或杂芳基,它们都是任选被取代的; Ar'1是例如亚苯基,亚萘基,二亚苯基,亚杂芳基,氧联二苯基,亚苯基D-D 1-D-亚苯基或-Ar' -A 1 -Y 1-A 1 -Ar'1 - ; - - - - 其中这些基团任选被取代; Ae'是亚苯基,亚萘基,亚蒽基,亚菲基或亚杂芳基,全部任意取代; A是例如直接键,-O - , - S-或-NR 6 - 。 Y尤其是C 1 -C 18亚烷基; X是卤素; D是例如-O - , - S-或-NR 6 - 。 D,尤其是C 1 -C 18亚烷基; 在ArF抗蚀剂技术中特​​别适合作为光潜酸。

    Sulfonate derivatives and the use thereof as latent acids

    公开(公告)号:US07326511B2

    公开(公告)日:2008-02-05

    申请号:US10495710

    申请日:2003-01-28

    IPC分类号: G03F7/00 G03F7/004

    摘要: Chemically amplified photoresist compositions comprising, (a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and (b) a compound of the formula (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (Iva), (Ivb), (Va), (Vb) or (VIa), wherein n is 1 or 2; m is 0 or 1; X0 is —[CH2]h—X or —CH═CH2; h is 2, 3, 4, 5 or 6; R1 when n is 1, is for example optionally substituted phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl; R1, when n is 2, is for example optionally substituted phenylene or naphthylene; R2 for example has one of the meanings of R1; X is for example —OR20, —NR21R22, —SR23; X′ is -X1-A3-X2-; X1 and X2 are for example —O—, —S— or a direct bond; A3 is e.g. phenylene; R3 has for example one of the meanings given for R1; R4 has for example one of the meaning given for R2; R5 and R6 e.g. are hydrogen; G i.a. is —S— or —O—; R7 when n is 1, e.g. is phenyl, optionally substituted, when n is 2, is for example phenylene; R8 and R9 e.g. are C1-C18alkyl; R10 has one of the meanings given for R7; R11 i.a. is C1-C18alkyl; R12, R13, R14, R15 R16, R17 and R18 for example are hydrogen or C1-C18alkyl; R20, R21, R22 and R23 i.a are phenyl or C1-C18alkyl; give high resolution with good resist profile

    Halogenated oxime derivatives and the use thereof as latent acids
    9.
    发明申请
    Halogenated oxime derivatives and the use thereof as latent acids 有权
    卤化肟衍生物及其作为潜伏酸的用途

    公开(公告)号:US20060246377A1

    公开(公告)日:2006-11-02

    申请号:US10543429

    申请日:2004-02-09

    摘要: Compounds of the formula (I) or (II) wherein R1 is C1-C10haloalkylsulfonyl, halobenzenesulfonyl, C2-C10haloalkanoyl, halobenzoyl; R2 is halogen or C1-C10 haloalkyl; Ar1 is phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl, all of which are optionally substituted; Ar′1 is for example phenylene, naphthylene, diphonylene, heteroarylene, oxydiphenylene, phenyleneD-D1-D-phenylene or —Ar′1-A1-Y1-A1-Ar′1—; wherein these radicals optionally are substituted; Ae′, is phenylene, naphthylene, anthracylene, phenanthrylene, or heteroarylene, all optionally substituted; A, is for exampfe a direct bond, -0-, —S—, or —NR6—; Y, inter alia is C1-C18alkylene; X is halogen; D is for example -0-, —S— or —NR6—; D, inter alia is C1-C18alkylene; are particularly suitable as photolatent acids in ArF resist technology.

    摘要翻译: 式(I)或(II)的化合物,其中R 1是C 1 -C 10卤代烷基磺酰基,卤代苯磺酰基,C 2 卤代烷酰基,卤代苯甲酰基, R 2是卤素或C 1 -C 10卤代烷基; Ar1是苯基,联苯基,芴基,萘基,蒽基,菲基或杂芳基,它们都是任选被取代的; Ar'1是例如亚苯基,亚萘基,二亚苯基,亚杂芳基,氧联二苯基,亚苯基D-D 1-D-亚苯基或-Ar' -A 1 -Y 1-A 1 -Ar'1 - ; - - - - 其中这些基团任选被取代; Ae'是亚苯基,亚萘基,亚蒽基,亚菲基或亚杂芳基,全部任意取代; A,是直接键合的,-O - , - S-或-NR 6 - 。 Y尤其是C 1 -C 18亚烷基; X是卤素; D是例如-O - , - S-或-NR 6 - 。 D,尤其是C 1 -C 18亚烷基; 在ArF抗蚀剂技术中特​​别适合作为光潜酸。