Oxime derivatives and the use thereof as latent acids

Details Oxime derivatives and the use thereof as latent acids Oxime derivatives and the use thereof as latent acids

2001-04-24

2002-11-26

Berman, Susan W. (Department: 1711)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S281100, C430S913000, C430S916000, C430S919000, C522S026000, C522S033000, C522S039000, C522S053000, C522S063000, C522S126000, C548S112000, C548S413000, C548S558000, C548S565000, C549S006000, C549S029000, C549S061000, C549S068000, C549S474000, C549S479000, C549S480000, C558S405000, C558S408000, C564S253000, C564S254000, C564S265000

Reexamination Certificate

active

06485886

ABSTRACT:

The invention relates to new oxime derivatives, photopolymerisable compositions comprising said compounds and to the use of the compounds as latent acids, which can be activated by irradiation with light.
In U.S. Pat. No. 4,540,598 surface-coating compositions based on photosensitive oxime sulfonates and customary acid-curable resins are disclosed. In EP 571330 the use of &agr;-(4-toluene-sulfon-yloxyimino)-4-methoxybenzyl cyanide and &agr;-(4-toluene-sulfonyloxyimino)-3-thienylmethyl cyanide as latent acid donors in positive and negative photoresists for wavelengths of 340-390 nm, especially those in the radiation region of the mercury i line (365 nm) is described. In GB 2306958 the use of oxime-sulfonates as latent acid donors in positive and negative photoresists for wavelengths between 180 and 600 nm, especially those in the radiation region beyond 390 nm is reported. In U.S. Pat. No. 5,714,625 non-aromatic &agr;-(alkylsulfonyloxyimino)-1-cyclo-hexenylacetonitriles and &agr;-(alkylsulfonyloxyimino)-1-cyclopentenylacetonitriles are disclosed. The preparation of several quinone oxime compounds is described by Ralph B. Davies et al. in J. Chem. Eng. Data 8, 580 (1963).
In the art, a need still exists, especially for reactive non-ionic latent acid donors that are thermally and chemically stable and that, after being activated by light, can be used as catalysts for a variety of acid-catalysed reactions, such as polycondensation reactions, acid-catalysed depolymerisation reactions, acid-catalysed electrophilic substitution reactions or the acid-catalysed removal of protecting groups. There is also a need for compounds that when irradiated with light are converted into acids and are capable of acting as solubility inhibitors in resist formulations. Furthermore there is a need for photolatent acids which can be bleached upon irradiation.
Surprisingly, it has now been found that specific oxime derivatives are especially suitable as catalysts for such reactions. The optical absorption spectra of the specific compounds of the invention are particularly tunable over a wide range of the electromagnetic spectrum. Furthermore they can be bleached upon irradiation.
Accordingly, the present invention pertains to compounds of the formula I and II
wherein
m is 0 or 1;
R
1
is phenyl which is unsubstituted or substituted by one or more of the radicals C
1
-C
12
alkyl, C
1
-C
4
haloalkyl, halogen, phenyl, OR
6
, NR
7
R
8
, SR
9
and/or —S-phenyl, optionally the substituents OR
6
, SR
9
or NR
7
R
8
form 5- or 6-membered rings, via the radicals R
6
, R
7
, R
8
and/or R
9
, with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring,
or R
1
is naphthyl, anthracyl or phenanthryl, the radicals naphthyl, anthracyl and phenanthryl being unsubstituted or substituted by C
1
-C
6
alkyl, phenyl, OR
6
, NR
7
R
8
, SR
9
and/or —S-phenyl, optionally the substituents OR
6
, SR
9
or NR
7
R
8
form 5- or 6-membered rings, via the radicals R
6
, R
7
, R
8
and/or R
9
with further substituents on the naphthyl, anthracyl or phenanthryl ring or with one of the carbon atoms of the naphthyl, anthracyl or phenanthryl ring,
or R
1
is a heteroaryl radical which is unsubstituted or substituted by C
1
-C
6
alkyl, phenyl, OR
6
, NR
7
R
8
, SR
9
and/or —S-phenyl, optionally the substituents OR
6
, SR
9
or NR
7
R
8
form 5- or 6-membered rings, via the radicals R
6
, R
7
, R
8
and/or R
9
with further substituents on the heteroaryl ring or with one of the carbon atoms of the heteroaryl ring,
or, if m is 0, R
1
additionally is C
2
-C
6
alkoxycarbonyl, phenoxycarbonyl, CN, hydrogen or C
1
-C
12
alkyl;
R′
1
is C
2
-C
12
alkylene, phenylene, naphthylene,
 diphenylene or oxydiphenylene, these radicals being unsubstituted or substituted by C
1
-C
12
alkyl;
R
2
is CN;
n is 1 or 2;
R
3
is C
2
-C
6
haloalkanoyl, halobenzoyl, or a group
 Y
1
, Y
2
and Y
3
are independently of each other O or S;
R
4
and R
5
are independently of each other hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
1
-C
4
haloalkyl, CN, NO
2
, C
2
-C
6
alkanoyl, benzoyl, phenyl, —S-phenyl, OR
6
, SR
9
, NR
7
R
8
, C
2
-C
6
-alkoxycarbonyl, phenoxycarbonyl, S(O)
n
C
1
-C
6
alkyl, S(O)
n
C
6
-C
12
aryl, C
1
-C
12
alkyl-substituted S(O)
n
C
6
-C
12
aryl, SO
2
O—C
1
-C
6
alkyl, SO
2
O—C
6
-C
10
aryl or NHCONH
2
, or R
4
and R
5
together are —C(R
12
)═C(R
13
)—C(R
14
)═C(R
15
)—;
R
6
is hydrogen, phenyl; C
1
-C
12
alkyl which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
-alkanoyl; or R
6
is C
2
-C
12
alkyl interrupted by —O—, optionally substituted by phenyl, OH, C
1
-C
12
-alkoxy, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
alkanoyl; R
7
and R
8
are independently of each other hydrogen; C
1
-C
12
alkyl which is unsubstituted or substituted by OH, C
1
-C
4
alkoxy, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or C
1
-C
6
alkanoyl; or R
7
and R
8
are C
2
-C
12
alkyl interrupted by —O—, optionally substituted by OH, C
1
-C
4
alkoxy, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or C
1
-C
6
alkanoyl; or R
7
and R
8
are phenyl, C
2
-C
6
alkanoyl, benzoyl, C
1
-C
6
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, or R
7
and R
8
, together with the nitrogen atom to which they are bound, form a 5-, 6- or 7-membered ring which optionally is interrupted by —O— or by —NR
7a
—;
R
7a
is hydrogen, phenyl; C
1
-C
12
alkyl which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
-alkanoyl; or R
7a
is C
2
-C
12
alkyl interrupted by —O—, optionally substituted by phenyl, OH, C
1
-C
12
alkoxy, C
1
-C
12
alkylsulfonyl, phenylsultonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
-alkanoyl: or R
7a
is phenyl, C
2
-C
6
alkanoyl, benzoyl, C
1
-C
6
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
R
9
is C
1
-C
12
alkyl which is unsubstituted or substituted by OH and/or C
1
-C
4
alkoxy; or C
2
-C
12
-alkyl interrupted by —O—, soptionally substituted by OH and/or C
1
-C
4
alkoxy;
A is S, O, NR
7a
, or a group of formula A1, A2, A3 or A4
R
10
and R
11
independently of each other have one of the meanings given for R
4
, or R
10
and
R
11
together are —CO—NR
7a
CO—, or R
10
and R
11
together are —C(R
12
)═C(R
13
)—C(R
14
)═C(R
15
)—;
R
12
, R
13
, R
14
and R
15
independently of one another are hydrogen, C
1
-C
4
alkyl, halogen, phenyl, OR
6
, SR
9
, NR
7
R
8
, —S-phenyl, C
2
-C
6
alkoxycarbonyl, phenoxycarbonyl, CN, NO
2
, C
1
-C
4
haloalkyl, S(O)
n
C
1
-C
6
alkyl, S(O)
n
C
6
-C
12
aryl, C
1
-C
12
alkyl-substituted S(O)
n
C
6
-C
12
aryl, SO
2
O—C
1
-C
6
alkyl, SO
2
O—C
6
-C
10
aryl or NHCONH
2
;
R
16
and R
17
independently of each other are C
1
-C
6
alkyl which is unsubstituted or substituted by halogen; or are phenyl which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen; R
18
and R
19
independently of each other have one of the meanings of R
16
, or R
18
and R
19
, or together are 1,2-phenylene or C
2
-C
6
alkylene which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen;
R
20
, R
21
and R
22
independently of each other are C
1
-C
6
alkyl which is unsubstituted or substituted by halogen; or are phenyl which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen; or R
21
and R
22
together are 2,2′-biphenylene or C
2
-C
6
alkylene which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen;
Z is CR
11
or N; and
Z
1
is —CH
2
—, S, O or NR
7a
.
C
1
-C
12
alkyl is linear or branched and is, for example, C
1
-C
8
—, C
1
-C
6
— or C
1
-C
4
alkyl. Examples are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl, octyl, nonyl, d

Affiliated with

Also associated with

Rating

Oxime derivatives and the use thereof as latent acids does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oxime derivatives and the use thereof as latent acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oxime derivatives and the use thereof as latent acids will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2956817