Nitrogen-containing organic compound, resist composition and patterning process
A resist composition comprising as a quencher a nitrogen-containing organic compound bearing a nitrogen-containing heterocycle and having a molecular weight of at least 380 exhibits a high resolution and satisfactory mask coverage dependence and is useful in microfabrication using electron beam or deep-UV.
1. A nitrogen-containing organic compound bearing a nitrogen-containing heterocycle and a steroid structure, represented by one of the general formulae (2′) to (10′):
wherein R 4 is each independently hydrogen, a straight, branched or cyclic C 1 -C 10 alkyl group, C 6 -C 15 aryl group or C 7 -C 15 aralkyl group, R 5 is hydrogen or methyl, R 6′ is an alkyl group of 21 to 49 carbon atoms having a steroid structure which may contain a hydroxyl, carbonyl, ester, ether, cyano or acetal group, R 7 is a single bond, methylene group, oxygen atom or sulfur atom, R 8 is a straight or branched C 1 -C 9 alkylene group, and R 9′ is an alkyl group of 22 to 50 carbon atoms having a steroid structure which may contain a hydroxyl, carbonyl, ester, ether or cyano group.
2. A resist composition comprising as a quencher at least one nitrogen-containing organic compound bearing a nitrogen-containing heterocycle and having a molecular weight of at least 380, represented by the general formula (1):
wherein R 1 is a straight, branched or cyclic divalent substituent group of 2 to 20 carbon atoms to form a nitrogen-containing heteroaliphatic or heteroaromatic ring with the nitrogen atom to which it is attached at both ends, which group may contain an oxygen, nitrogen, sulfur or halogen atom, R 2 is a straight or branched alkylene group of 2 to 10 carbon atoms which may contain a carbonyl group, and R 3 is —CO—R 6 , —CH 2 —OR 6 , R 9 , —CO—R 6′ , —CH 2 —OR 6′ or R 9′ wherein R 6 is selected from the group consisting of the following formulae:
and R 6′ ,
R 9 is selected from the group consisting of the following formulae:
and R 9′ ,
R 6′ is selected from the group consisting of the following formulae:
and R 9′ is selected from the group consisting of the following formulae:
3. The resist composition of claim 2 , comprising as a quencher at least one of nitrogen-containing organic compounds bearing a nitrogen-containing heterocycle and having a molecular weight of at least 430, represented by the general formulae (2) to (10):
wherein R 4 is each independently hydrogen, a straight, branched or cyclic C 1 -C 10 alkyl group, C 6 -C 15 aryl group or C 7 -C 15 aralkyl group, R 5 is hydrogen or methyl, R 7 is a single bond, methylene group, oxygen atom or sulfur atom, R 8 is a straight or branched C 1 -C 9 alkylene group, R 9 is an alkyl group of 22 to 50 carbon atoms which may contain a hydroxyl, carbonyl, ester, ether or cyano group, and R 6 is selected from the group consisting of the following formulae:
and R 6′ ,
R 9 is selected from the group consisting of the following formulae:
and R 9′ ,
R 6′ is selected from the group consisting of the following formulae:
and R 9′ is selected from the group consisting of the following formulae:
4. The resist composition of claim 2 , comprising as a quencher at least one of nitrogen-containing organic compounds bearing a nitrogen-containing heterocycle and a steroid structure and having a molecular weight of at least 430, represented by the general formulae (2′) to (10′):
wherein R 4 is each independently hydrogen, a straight, branched or cyclic C 1 -C 10 alkyl group, C 6 -C 15 aryl group or C 7 -C 15 aralkyl group, R 5 is hydrogen or methyl, R 7 is a single bond, methylene group, oxygen atom or sulfur atom, R 8 is a straight or branched C 1 -C 9 alkylene group, R 9′ is an alkyl group of 22 to 50 carbon atoms having a steroid structure which may contain a hydroxyl, carbonyl, ester, ether or cyano group, and R 6′ is selected from the group consisting of the following formulae:
and R 9′ is selected from the group consisting of the following formulae:
5. The resist composition of claim 3 , wherein the nitrogen-containing organic compound having any one of formulae (2) to (10) is one having the formula selected from the group consisting of the following formulae A-9 to A-62:
6. The resist composition of claim 4 , wherein the nitrogen-containing organic compound having any one of formulae (2′) to (10′) is one having the formula selected from the group consisting of the following formulae A-63 to A-76:
7. A nitrogen-containing organic compound bearing a nitrogen-containing heterocycle, represented by one of the general formulae (2) to (10):
wherein R 4 is each independently hydrogen, a straight, branched or cyclic C 1 -C 10 alkyl group, C 6 -C 15 aryl group or C 7 -C 15 aralkyl group, R 5 is hydrogen or methyl, R 7 is a single bond, methylene group, oxygen atom or sulfur atom, R 8 is a straight or branched C 1 -C 9 alkylene group, R 9 is an alkyl group of 22 to 50 carbon atoms which may contain a hydroxyl, carbonyl, ester, ether or cyano group, and R 6 is selected from the group consisting of the following formulae:
and R 6′ ,
R 9 is selected from the group consisting of the following formulae:
and R 9′ ,
R 6′ is selected from the group consisting of the following formulae:
and R 9′ is selected from the group consisting of the following formulae:
8. A nitrogen-containing organic compound bearing a nitrogen-containing heterocycle and a steroid structure, represented by one of the general formulae (2′) to (10′):
wherein R 4 is each independently hydrogen, a straight, branched or cyclic C 1 -C 10 alkyl group, C 6 -C 15 aryl group or C 7 -C 15 aralkyl group, R 5 is hydrogen or methyl, R 7 is a single bond, methylene group, oxygen atom or sulfur atom, R 8 is a straight or branched C 1 -C 9 alkylene group, R 9′ is an alkyl group of 22 to 50 carbon atoms having a steroid structure which may contain a hydroxyl, carbonyl, ester, ether or cyano group, and R 6′ is selected from the group consisting of the following formulae:
and R 9′ is selected from the group consisting of the following formulae:
9. The nitrogen-containing organic compound of claim 7 which is one having the formula selected from the group consisting of the following formulae A-9 to A-62:
10. The nitrogen-containing organic compound of claim 8 , which is one having the formula selected from the group consisting of the following formulae A-63 to A-76: