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

2000-03-23

2001-07-17

Ashton, Rosemary E. (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S325000, C430S326000, C430S919000

Reexamination Certificate

active

06261738

ABSTRACT:

The invention relates to new oxime derivatives, chemically amplified photoresist compositions comprising said compounds and to the use of the compounds as latent acids, which can be activated by irradiation with actinic electromagnetic radiation and electron beams.
In U.S. Pat. No. 4,540,598 surface-coating compositions comprising photosensitive oxime sulfonate compounds, e.g. 4-chloro-&agr;-trifluoroacetophenonoxime benzenesulfonate and customary acid-curable resins are disclosed. In U.S. Pat. No. 4,736,055 2,2,2-trifluoro-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate) is described as a component for the preparation of polymers which can be used as resins in positive photoresists. In U.S. Pat. No. 5,627,011 and U.S. Pat. No. 5,759,740 the use of &agr;-(4-toluene-sulfonyloxyimino)-4-methoxybenzyl cyanide and &agr;-(4-toluene-sulfonyloxyimino)-3-thienylmethyl cyanide as latent acid catalysts in chemically amplified 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-cyclohexenylacetonitriles and &agr;-(alkylsulfonyloxyimino)-1-cyclopentenylacetonitriles are disclosed. In EP 241423 oxime sulfonate compounds are employed in about 25% concentration as photolatent acid generators in non-chemically amplified positive resists. In Chemical Abstracts No. 97:144503, 78:97752, Synthesis (1995), 553, some fluoroketoxime sulfonate compounds are described as experimental products for synthetic studies.
In the art exists a need for reactive non-ionic latent acid donors that are thermally and chemically stable and that, after being activated by light, UV-radiation, X-ray irradiation or electron beams 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. A particular need exists for latent acid catalysts with high stability and good solubility in the field of chemically amplified photoresists.
Surprisingly, it has now been found that specific oxime derivatives, as described below, are especially suitable as catalysts for the aforementioned acid catalyzed reactions. The optical absorption spectra of the specific compounds of the invention are tunable over a wide range of the electromagnetic spectrum and particularly suitable for applications in the deep UV range. Furthermore, chemically amplified photoresist compositions comprising oxime derivatives of the present invention are thermally stable, even at high bake temperatures during processing and provide high photospeed.
The invention accordingly relates to a chemically amplified photoresist composition 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) as photosensitive acid donor, at least one compound of the formula I, II or III
wherein
R
1
is hydrogen, unsubstituted C
1
-C
12
alkyl; C
1
-C
12
alkyl which is substituted by C
3
-C
30
cycloalkyl; or R
1
is C
3
-C
30
cycloalkyl, C
1
-C
8
haloalkyl, C
2
-C
12
alkenyl, C
4
-C
8
cycloalkenyl, C
6
-C
12
bicycloalkenyl, camphoryl;
phenyl, which is unsubstituted or substituted by one or more of the radicals C
1
-C
12
alkyl, C
1
-C
4
haloalkyl, phenyl-C
1
-C
3
-alkyl, halogen, phenyl, OR
4
, NR
5
R
6
, SR
7
, SOR
7
, and/or SO
2
R
7
, optionally the substituents OR
4
, SR
7
and NR
5
R
6
form 5- or 6-membered rings, via the radicals R
4
, R
5
, R
6
and/or R
7
, 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, wherein the radicals naphthyl, anthracyl and phenanthryl are unsubstituted or substituted by C
1
-C
6
alkyl, phenyl, OR
4
, NR
5
R
6
, SR
7
, SOR
7
, and/or SO
2
R
7
, optionally the substituents OR
4
, SR
7
and NR
5
R
6
form 5- or 6-membered rings, via the radicals R
4
, R
5
, R
6
and /or R
7
with further substituents on the naphthyl, anthracyl or phenanthryl ring or with one of the carbon atoms of the naphthyl, anthracyl or phenanthryl ring; ps or R
1
is a heteroaryl radical which is unsubstituted or substituted by C
1
-C
6
alkyl, phenyl, OR
4
, NR
5
R
6
, SR
7
, SOR
7
, and/or SO
2
R
7
, optionally the substituents OR
4
, SR
7
and NR
5
R
6
form 5- or 6-membered rings, via the radicals R
4
, R
5
, R
6
and/or R
7
with further substituents on the heteroaryl ring or with one of the carbon atoms of the heteroaryl ring;
wherein all radicals R
1
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 phenylene, naphthylene,
diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted by C
1
-C
12
alkyl; or R′
1
is C
1
-C
12
-alkylene or
A is —O—, —S—, —NR
4
—, —O(CO)—, —S(CO)—, —NR
4
(CO)—, —SO—, —SO
2
—, or —OSO
2
—;
A, is C
1
-C
12
alkylene or C
2
-C
12
alkylene, which is interrupted by one or more —O—;
R
2
is halogen or C
1
-C
10
haloalkyl;
R
3
is C
1
-C
18
alkylsulfonyl, C
1
-C
10
haloalkylsulfonyl, camphorylsulfonyl, phenyl-C
1
-C
3
alkyl-sulfonyl, C
3
-C
12
cycloalkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups cycloalkyl, phenyl, naphthyl, anthracyl and phenanthryl of the radicals C
3
-C
12
cycloalkylsulfonyl, phenyl-C
1
-C
3
alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl and phenanthrylsulfonyl are unsubstituted or substituted by one or more halogen, C
1
-C
4
haloalkyl, CN, NO
2
, C
1
-C
16
alkyl, phenyl, C
1
-C
4
alkylthio, OR
4
, COOR
7
, C
1-C
4
alkyl-(OC)O—, R
7
OSO
2
— and/or —NR
5
R
6
;
or R
3
is C
2
-C
6
haloalkanoyl, halobenzoyl, or a group
Y
1
, Y
2
and Y
3
independently of each other are O or S;
R′
3
is phenylenedisulfonyl, naphthylenedisulfonyl,
di-phenylenedisulfonyl, or oxydiphenylenedisulfonyl, wherein these radicals are unsubstituted or substituted by C
1-C
12
alkyl; or R′
3
is C
2
-C
12
alkylenedisulfonyl;
X is halogen;
R
4
is hydrogen, phenyl,
C
1
-C
18
alkyl which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
2
-C
12
alkoxy-carbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR
5
R
6
, C
1-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
alkanoyl;
or R
4
is C
2
-C
18
alkyl which is interrupted by one or more —O—, and which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
2
-C
12
alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR
5
R
6
, C
1-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C
2
-C
6
alkanoyl;
or R
4
is C
2
-C
18
alkanoyl which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
2
-C
12
alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR
5
R
6
, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C
2
-C
6
alkanoyl;
or R
4
is C
1
-C
18
alkylsulfonyl which is unsubstituted or substituted by phenyl, OH, C
1
-C
12
alkoxy, C
2
-C
12
alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR
5
R
6
, C
1-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)-sulfonyl, and/or by C
2
-C
6
alkanoyl;
or R
4
is phenylsulfonyl, or (4-methylphenyl)sulfonyl;
R
5
and R
6
independently of each other are hydrogen or C
1
-C
18
alkyl which is unsubstituted or substituted by OH, C
1
-C
4
alkoxy, C
2
-C
12
alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, phenylamino, phenylaminocarbonyl, C
1
-C
12
alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or C
1
-C
6
alkanoyl;
or R
5
and R
6
are C
2
-C
18
alkyl which is

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-2502234