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公开(公告)号:US20080004464A1
公开(公告)日:2008-01-03
申请号:US11667780
申请日:2005-11-14
申请人: Peter Murer , Jean-Pierre Wolf , Stephan Burkhardt , Hansjorg Grutzmacher , Daniel Stein , Kurt Dietliker
发明人: Peter Murer , Jean-Pierre Wolf , Stephan Burkhardt , Hansjorg Grutzmacher , Daniel Stein , Kurt Dietliker
CPC分类号: G03F7/029 , C07F9/5036 , C07F9/5337 , C07F9/5537 , C07F9/65515 , C07F9/6552
摘要: The invention relates to a process for the preparation of (bis)acylphosphanes of formula I, wherein n and m are each independently of the other 1 or 2; R1 if n=1, is e.g. unsubstituted or substituted C1-C18alkyl or C2-C18alkenyl, or phenyl, R1 if n=2, is e.g. a divalent radical of the monovalent radical defined above; R2 is e.g. C1-C18alkyl, C3-C12cycloalkyl, C2-C18alkenyl, mesityl, phenyl, naphthyl; R3 is one of the radicals defined under R1; the process comprises the steps a) contacting e.g. elemental phosphorous [P]∞, P(Hal)3 with a reducing metal optionally in the presence of a catalyst or an activator in a solvent to obtain metal phosphides Me3P or Me′3P2, wherein Me is an alkali metal and Me′ is an earth alkali metal or to obtain metal polyphosphides b) optionally adding a proton source, optionally in the presence of a catalyst or an activator to obtain metal dihydrogen phosphides MePH2; c) subsequent acylation reaction with m acid halides of formula III or m carboxylic acid esters of formula IV or, in case that in formula I m=1, with one carboxylic ester of formula IV followed by one acid halide of formula III or vice versa, wherein R is the residue of an alcohol and R2 is as defined above; d) alkylation reaction subsequent reaction with an electrophilic agent R1Hal or other electrophilic agents to obtain the compounds of formula I. An oxidation step may follow to obtain mono- and bisacylphosphane oxides or mono- and bisacylphosphane sulfides, which are used as photoinitiators.
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公开(公告)号:US20050153244A1
公开(公告)日:2005-07-14
申请号:US10495710
申请日:2003-01-28
IPC分类号: C07C301/00 , C07C309/67 , C07C309/68 , C07C317/04 , C07C317/14 , C07C323/66 , C07C381/00 , C07D209/48 , C07D209/76 , C07D291/00 , C07D333/36 , G02B5/20 , G03F7/00 , G03F7/004 , G03F7/038 , G03F7/039 , G03F7/075 , H01L21/027 , G03C5/00
CPC分类号: G03F7/0037 , B33Y70/00 , C07C323/66 , C07C381/00 , G03F7/001 , G03F7/0045 , G03F7/038 , G03F7/0382 , G03F7/0392 , G03F7/0397 , G03F7/0758 , Y10S430/114
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.
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公开(公告)号:US07687657B2
公开(公告)日:2010-03-30
申请号:US11667780
申请日:2005-11-14
申请人: Peter Murer , Jean-Pierre Wolf , Stephan Burkhardt , Hansjörg Grützmacher , Daniel Stein , Kurt Dietliker
发明人: Peter Murer , Jean-Pierre Wolf , Stephan Burkhardt , Hansjörg Grützmacher , Daniel Stein , Kurt Dietliker
CPC分类号: G03F7/029 , C07F9/5036 , C07F9/5337 , C07F9/5537 , C07F9/65515 , C07F9/6552
摘要: The invention relates to a process for the preparation of (bis)acylphosphanes of formula I, wherein n and m are each independently of the other 1 or 2; R1 if n=1, is e.g. unsubstituted or substituted C1-C18alkyl or C2-C18alkenyl, or phenyl, R1 if n=2, is e.g. a divalent radical of the monovalent radical defined above; R2 is e.g. C1-C18alkyl, C3-C12cycloalkyl, C2-C18alkenyl, mesityl, phenyl, naphthyl; R3 is one of the radicals defined under R1; the process comprises the steps a) contacting e.g. elemental phosphorous [P]∞, P(Hal)3 with a reducing metal optionally in the presence of a catalyst or an activator in a solvent to obtain metal phosphides Me3P or Me′3P2, wherein Me is an alkali metal and Me′ is an earth alkali metal or to obtain metal polyphosphides b) optionally adding a proton source, optionally in the presence of a catalyst or an activator to obtain metal dihydrogen phosphides MePH2; c) subsequent acylation reaction with m acid halides of formula III or m carboxylic acid esters of formula IV or, in case that in formula I m=1, with one carboxylic ester of formula IV followed by one acid halide of formula III or vice versa, wherein R is the residue of an alcohol and R2 is as defined above; d) alkylation reaction subsequent reaction with an electrophilic agent R1Hal or other electrophilic agents to obtain the compounds of formula I. An oxidation step may follow to obtain mono- and bisacylphosphane oxides or mono- and bisacylphosphane sulfides, which are used as photoinitiators.
摘要翻译: 本发明涉及制备式(I)的(双)酰基磷烷的方法,其中n和m各自独立地为1或2; 如果n = 1,则为R1。 未取代或取代的C1-C18烷基或C2-C18链烯基,或苯基,如果n = 2,则为R1。 上述定义的一价基团的二价基团; R2是例如 C 1 -C 18烷基,C 3 -C 12环烷基,C 2 -C 18烯基,三甲苯基,苯基,萘基; R3是R1下定义的基团之一; 该方法包括以下步骤:a) 元素磷[P]∞,P(Hal)3与还原金属,任选在催化剂或活化剂存在下在溶剂中,得到金属磷化物Me3P或Me'3P2,其中Me为碱金属,Me'为 碱土金属或获得金属多磷酸盐b)任选地在催化剂或活化剂存在下加入质子源以获得金属二磷化磷MePH2; c)随后与式III的酰基卤或式IV的羧酸酯的酰化反应,或在式I中m = 1的情况下,与一种式IV的羧酸酯接触,然后加入式III的酰卤,反之亦然 其中R是醇的残基,R 2如上所定义; d)烷基化反应随后与亲电子试剂R1Hal或其他亲电子试剂反应以获得式I化合物。随后可以进行氧化步骤以获得用作光引发剂的单酰基和双酰基膦烷氧化物或单酰基和双酰基磷烷硫化物。
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公开(公告)号:US07439401B2
公开(公告)日:2008-10-21
申请号:US10564711
申请日:2004-07-09
申请人: Reinhard H. Sommerlade , Souâd Boulmaâz , Jean-Pierre Wolf , Jens Geier , Hansjörg Grützmacher , Markus Scherer , Hartmut Schönberg , Daniel Stein , Peter Murer , Stephan Burkhardt
发明人: Reinhard H. Sommerlade , Souâd Boulmaâz , Jean-Pierre Wolf , Jens Geier , Hansjörg Grützmacher , Markus Scherer , Hartmut Schönberg , Daniel Stein , Peter Murer , Stephan Burkhardt
IPC分类号: C07F9/02
CPC分类号: C07F9/5036 , C07F9/5337
摘要: The present invention relates to a new, selective process for the preparation of mono- and bisacylphosphanes of formula (I) n and m are each independently of the other 1 or 2; R1, if n=1, is e.g. phenyl R1, if n=2, is e.g. C1-C18alkylene or phenylene; R2 is e. g. C1-C18alkyl, phenyl or substituted phenyl; R3 is e. g. C1-C18alkyl, by (1) reacting a phosphorous halide of formula IIa or a phosphorous halide oxide of formula (IIb) or a phosphorous halide sulfide of formula (IIc) with an alkali metal in a solvent in the presence of a proton source; (2) subsequent reaction with m acid halides of formula (III) An oxidation step may follow to obtain mono- and bisacylphosphane oxides or mono- and bisacylphosphane sulfides.
摘要翻译: 本发明涉及制备式(I)的单 - 和双酰基磷烷的新的选择性方法,n和m各自独立地为1或2; 如果n = 1,则为R 1。 苯基R 1,如果n = 2,则为例如。 C 1 -C 18亚烷基或亚苯基; R 2是e。 G。 C 1 -C 18烷基,苯基或取代的苯基; R 3是e。 G。 通过(1)使式IIa的卤化磷或式(IIb)的卤化磷氧化物或式(IIb)的卤化磷化物或式(IIb) IIc)与碱金属在溶剂中在质子源存在下反应; (2)随后与式(III)的酰卤反应可以进行氧化步骤以获得单酰基和双酰基氧化膦或单酰基和双酰基磷烷硫化物。
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公开(公告)号:US20100104979A1
公开(公告)日:2010-04-29
申请号:US12593025
申请日:2008-03-25
申请人: Kurt Dietliker , Peter Murer , Rinaldo Hüsler , Tunja Jung
发明人: Kurt Dietliker , Peter Murer , Rinaldo Hüsler , Tunja Jung
IPC分类号: G03F7/20 , C07C59/76 , C07D307/00 , C07D305/12 , C07F7/08 , C07D265/30 , C07C69/95 , C07D211/06 , C07C233/00 , G03F7/004 , C08F2/46
CPC分类号: C07D211/32 , C07C49/83 , C07C49/835 , C07C49/84 , C07C62/38 , C07C69/757 , C07C219/12 , C07C235/82 , C07C2601/14 , C07D295/185 , C07D305/12 , C07F7/0836 , C07F7/0838 , C07F7/1804 , G03F7/004 , G03F7/38 , G03F7/40
摘要: Compounds of the Formula (I) wherein x is an integer from 1-4; p is an integer from 1-3; q is an integer from 0-3; Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more Cl, CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or more OR6, COOR or halogen; R1 if x is 1, is ORS, O—X+, NR8R9, C1-C20alkyl optionally substituted by one or more COOR10, or is C2-C20alkyl interrupted by one ore more O, or is C2-C5alkenyl or phenyl-C1-C4alkyl; R1 if x is 2, is for example C1-C20alkylene; R1 if x is 3, is for example a tri-valent radical; R1if x is 4, is for example a tetravalent radical; R2and R3are hydrogen or C1-C8alkyl, or R2and R3 together are O, C1-C3alkylene or CH═CH; R4 is C1-C4alkyl; R5, R6, R7, R8, R9 and R10 are for example hydrogen or C1-C4alkyl; and X is a x-valent cationic counter ion; are in particular suitable as photoinitiators for the curing with UV-A light (320-450 nm).
摘要翻译: 式(I)的化合物,其中x是1-4的整数; p是1-3的整数; q是0-3的整数; Ar是苯基,萘基,蒽基或菲基,其各自任选被一个或多个被一个或多个OR 6,COOR或卤素取代的C 1,CN,OR 5,C 3 -C 5链烯基或C 1 -C 6烷基取代; R 1如果x是1,是ORS,O-X +,NR 8 R 9,任选被一个或多个COOR 10取代的C 1 -C 20烷基,或是被一个或多个O取代的C 2 -C 20烷基,或者是C 2 -C 5烯基或苯基-C 1 -C 4烷基; R1如果x为2,例如为C 1 -C 20亚烷基; 如果x是3,则R1是例如三价基; R1if x为4,例如为四价基团; R 2和R 3为氢或C 1 -C 8烷基,或R 2和R 3一起为O,C 1 -C 3亚烷基或CH = CH; R4是C1-C4烷基; R5,R6,R7,R8,R9和R10是例如氢或C1-C4烷基; X为x-阳离子抗衡离子; 特别适用于用UV-A光(320-450nm)固化的光引发剂。
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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
CPC分类号: G03F7/0037 , B33Y70/00 , C07C323/66 , C07C381/00 , G03F7/001 , G03F7/0045 , G03F7/038 , G03F7/0382 , G03F7/0392 , G03F7/0397 , G03F7/0758 , Y10S430/114
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.
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公开(公告)号:US07399577B2
公开(公告)日:2008-07-15
申请号:US10543429
申请日:2004-02-09
IPC分类号: G03C5/00 , C07C255/50 , C07C251/32
CPC分类号: C07C251/48 , B33Y70/00 , C07C381/00 , C07C2603/18 , C07C2603/20 , C07C2603/40 , C07D209/86 , C07D307/91 , C07D333/76 , G03F7/0007 , G03F7/0045 , G03F7/0046 , G03F7/0382 , G03F7/0392
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。
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公开(公告)号:US07326511B2
公开(公告)日:2008-02-05
申请号:US10495710
申请日:2003-01-28
CPC分类号: G03F7/0037 , B33Y70/00 , C07C323/66 , C07C381/00 , G03F7/001 , G03F7/0045 , G03F7/038 , G03F7/0382 , G03F7/0392 , G03F7/0397 , G03F7/0758 , Y10S430/114
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
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39.
公开(公告)号:US20060246377A1
公开(公告)日:2006-11-02
申请号:US10543429
申请日:2004-02-09
IPC分类号: G03C5/00 , C07C255/50 , C07C251/32
CPC分类号: C07C251/48 , B33Y70/00 , C07C381/00 , C07C2603/18 , C07C2603/20 , C07C2603/40 , C07D209/86 , C07D307/91 , C07D333/76 , G03F7/0007 , G03F7/0045 , G03F7/0046 , G03F7/0382 , G03F7/0392
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。
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公开(公告)号:US07026094B2
公开(公告)日:2006-04-11
申请号:US10478963
申请日:2002-05-23
申请人: Akira Matsumoto , Hitoshi Yamato , Toshikage Asakura , Masaki Ohwa , Peter Murer
发明人: Akira Matsumoto , Hitoshi Yamato , Toshikage Asakura , Masaki Ohwa , Peter Murer
CPC分类号: G03F7/0045 , B33Y70/00 , C07C309/00 , C07D333/36 , G03F7/0007 , G03F7/001 , G03F7/0382 , G03F7/0392 , Y10S430/114 , Y10S430/117 , Y10S430/12 , Y10S430/122
摘要: New oxime sulfonate compounds of the formula (I) and (II), wherein R1 is C1-C12alkyl, C1C4haloalkyl, hydrogon, OR9, NR10R11, SR12 or is phenyl which is unsubstituted or substituted by OH, C1-C18alkyl, halogen and/or C1-C12alkoxy; R2, R3, R4 and R5 are for example hydrogen or C1-C12alkyl; R6 is for example is C1-C18alkylsulfonyl, phenyl-C1-C3alkylsulfonyl or phenylsulfonyl; R′6 is for example phenylenedisulfonyl or diphenylenedisulfonyl; R7, R8 and R9 for example are hydrogen or C1-C6alkyl; R10 and R11, are for example hydrogen or C1-C18alkyl; R12 is for example hydrogen, phenyl or C1-C18alkyl; A is S, O, NR13, or a group of formula A1, A2 or A3, R21 and R22 independently of one other have one of the meanings given for R7; R23, R24, R25 and R26 independently of one another are for example hydrogen, C1-C4alkyl, halogen or phenyl; Z is CR22 or N; and Z1 is CR22 or N; and Z1 is CR22 or N; and Z1 is CH2, S, O or NR13 are particularly suitable as photo-latent acids in resist applications.
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