IP Library Granted Patent US 9,766,541
Granted Patent B2
US 9,766,541 · App. 15/186,044 · Granted Sep 19, 2017

Positive-type resist composition, method for forming resist pattern, photo-reactive quencher, and polymeric compound

Inventors: Hiroto Yamazaki (Kawasaki, JP); Yoshitaka Komuro (Kawasaki, JP); Masatoshi Arai (Kawasaki, JP); Daisuke Kawana (Kawasaki, JP); Kenta Suzuki (Kawasaki, JP); Tatsuya Fujii (Kawasaki, JP)
Assignee: TOKYO OHKA KOGYO CO., LTD.
G03F7/0045C07C65/10C07C309/06C07C309/12C07C309/19C07C381/12C08F216/10G03F7/004G03F7/0046G03F7/038G03F7/039G03F7/0397G03F7/2059G03F7/322H01L21/0274C07C2602/42C07C2603/74
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Quick Facts
Patent No.
US 9,766,541
App. No.
15/186,044
Granted
Sep 19, 2017
Kind
B2
Abstract

A positive-type resist composition which generates an acid upon exposure and whose solubility in an alkali developing solution increases under the action of an acid, the composition including a base material component whose solubility in an alkali developing solution increases under the action of an acid; and a compound represented by the following general formula (m0): Z 01 to Z 04 each independently represent a substituent having electron withdrawing properties, Rb 21 and Rb 22 each independently represent an alkyl group, an alicyclic hydrocarbon group which may have a substituent, or a hydroxyl group, Rb 1 represents an aryl group which may have a substituent, an alkyl group, or an alkenyl group, n1 and n2 represent an integer of 0 to 3, and X0 − represents an organic anion.

Claims (82)

1. A positive-type resist composition which generates an acid upon exposure and whose solubility in an alkali developing solution increases under the action of an acid, the composition comprising

a base material component (A) whose solubility in an alkali developing solution increases under the action of an acid; and

a compound (m) represented by the following general formula (m0):

wherein Z 01 to Z 04 each independently represents a substituent having electron withdrawing properties,

Rb 21 and Rb 22 each independently represents an alkyl group, an alicyclic hydrocarbon group which may have a substituent, or a hydroxyl group, with the proviso that the substituent which Rb 21 and Rb 22 may have does not include a substituent having electron withdrawing properties,

Rb 1 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent,

n1 and n2 each independently represents an integer of 0 to 3, and

X0 − represents an organic anion.

2. The positive-type resist composition according to claim 1 , comprising:

a base material component (A) whose solubility in an alkali developing solution increases under the action of an acid;

an acid generator component (B1) which generates an acid upon exposure and includes the compound (m) represented by general formula (m0); and

a photo-reactive quencher (D1).

3. The positive-type resist composition according to claim 1 , comprising:

a base material component (A) whose solubility in an alkali developing solution increases under the action of an acid;

an acid generator component (B2) which generates an acid upon exposure; and

a photo-reactive quencher (D2) which includes the compound (m) represented by general formula (m0).

4. The positive-type resist composition according to claim 1 ,

wherein X0 − in general formula (m0) represents an organic anion represented by any one of the following general formulae (d1-an-1) to (d1-an-3):

wherein Rd 1 to Rd 4 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that two or more fluorine atoms are not bonded to a carbon atom adjacent to the S atom in Rd 2 of formula (d1-an-2), and Yd 1 is a single bond or a divalent linking group.

5. The positive-type resist composition according to claim 2 , wherein X0 − in general formula (m0) represents an organic anion represented by any one of the following general formulae (d1-an-1) to (d1-an-3):

wherein Rd 1 to Rd 4 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that two or more fluorine atoms are not bonded to a carbon atom adjacent to the S atom in Rd 2 of formula (d1-an-2), and Yd 1 is a single bond or a divalent linking group.

6. The positive-type resist composition according to claim 3 , wherein X0 − in general formula (m0) represents an organic anion represented by any one of the following general formulae (d1-an-1) to (d1-an-3):

wherein Rd 1 to Rd 4 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that two or more fluorine atoms are not bonded to a carbon atom adjacent to the S atom in Rd 2 of formula (d1-an-2), and Yd 1 is a single bond or a divalent linking group.

7. The positive-type resist composition according to claim 1 , wherein the base material component (A) includes a resin component (A1) which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

8. The positive-type resist composition according to claim 2 , wherein the base material component (A) includes a resin component (A1) which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

9. The positive-type resist composition according to claim 3 , wherein the base material component (A) includes a resin component (A1) which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

10. The positive-type resist composition according to claim 4 , wherein the base material component (A) includes a resin component (A1) which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

11. The positive-type resist composition according to claim 5 , wherein the base material component (A) includes a resin component (A1)which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

12. The positive-type resist composition according to claim 6 , wherein the base material component (A) includes a resin component (A1) which has a structural unit (a9) represented by general formula (a9-1) or a structural unit (a10) including an aromatic hydrocarbon group having a hydroxy group:

wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 represents a single bond or a divalent linking group, R 91 represents a hydrocarbon group which may have a substituent, and Ya 92 represents a divalent linking group.

13. A positive-type resist composition which generates an acid upon exposure and whose solubility in an alkali developing solution increases under the action of an acid, the composition comprising a base material component (A) whose solubility in an alkali developing solution increases under the action of an acid and which includes a resin component (A2) including a polymeric compound having a structural unit (a6) derived from a compound represented by the following general formula (a6-1):

wherein Z 01 to Z 04 each independently represents a substituent having electron withdrawing properties,

Rb 21 and Rb 22 each independently represents an alkyl group, an alicyclic hydrocarbon group which may have a substituent, or a hydroxyl group, with the proviso that the substituent which Rb 21 and Rb 22 may have does not have a substituent having electron withdrawing properties,

Rb 1 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent,

n1 and n2 each independently represents an integer of 0 to 3, and

X11-1 − represents an organic anion represented by any one of general formulae (a6-1-1) to (a6-1-3), and, in general formulae (a6-1-1) to (a6-1-3),

Rb 201 represents a chain-like alkenyl group which may have a substituent,

Rb 204 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent,

Rb 205 represents a chain-like alkenyl group which may have a substituent

Rb 206 to Rb 208 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that at least one of Rb 206 to Rb 208 represents a chain-like alkenyl group which may have a substituent,

Rb 102 represents a fluorine atom or a fluorinated alkyl group having 1 to 5 carbon atoms,

Yb 101 represents a single bond, or a divalent linking group including an oxygen atom,

Vb 101 to Vb 103 each independently represents a single bond, an alkylene group, a fluorinated alkylene group, an arylene group, or a fluorinated arylene group,

Lb 101 and Lb 102 each independently represents a single bond or an oxygen atom,

Lb 103 to Lb 105 each independently represents a single bond, —CO—, or —SO 2 —, and

n 101 is 0 or 1.

14. A method for forming a resist pattern, comprising:

forming a resist film using the positive-type resist composition according to any one of claims 1 to 13 on a support;

exposing the resist film; and

developing the exposed resist film to form a resist pattern.

15. A photo-reactive quencher comprising

a compound (md) represented by the following general formula (m0-d):

Z 01 to Z 04 each independently represents a substituent having electron withdrawing properties,

Rb 21 and Rb 22 each independently represents an alkyl group, an alicyclic hydrocarbon group which may have a substituent, or a hydroxyl group, with the proviso that the substituent which Rb 21 and Rb 22 may have does not include a substituent having electron withdrawing properties,

Rb 1 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent,

n1 and n2 each independently represents an integer of 0 to 3, and

X0 − represents an organic anion represented by any one of general formulae (d1-an-1) to (d1-an-3),

in general formulae (d1-an-1) to (d1-an-3),

Rd 1 to Rd 4 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that two or more fluorine atoms are not bonded to a carbon atom adjacent to the S atom in Rd 2 of formula (d1-an-2), and

Yd 1 represents a single bond or a divalent linking group.

16. A polymeric compound comprising a structural unit derived from a compound represented by the following general formula (a6-1):

wherein Z 01 to Z 04 each independently represents a substituent having electron withdrawing properties,

Rb 21 and Rb 22 each independently represent an alkyl group, an alicyclic hydrocarbon group which may have a substituent, or a hydroxyl group, with the proviso that the substituent which Rb 21 and Rb 22 may have does not include a substituent having electron withdrawing properties,

Rb 1 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent,

n1 and n2 each independently represents an integer of 0 to 3, and

X11-1 − represents an organic anion represented by any one of general formulae (a6-1-1) to (a6-1-3),

in general formulae (a6-1-1) to (a6-1-3),

Rb 201 represents a chain-like alkenyl group which may have a substituent,

Rb 204 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent,

Rb 205 represents a chain-like alkenyl group which may have a substituent,

Rb 206 to Rb 208 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, with the proviso that at least one of Rb 206 to Rb 208 represents a chain-like alkenyl group which may have a substituent,

Rb 102 represents a fluorine atom, or a fluorinated alkyl group having 1 to 5 carbon atoms,

Yb 101 represents a single bond, or a divalent linking group including an oxygen atom,

Vb 101 to Vb 103 each independently represents a single bond, an alkylene group, a fluorinated alkylene group, an arylene group, or a fluorinated arylene group,

Lb 101 and Lb 102 each independently represents a single bond or an oxygen atom,

Lb 103 to Lb 105 each independently represents a single bond, —CO—, or —SO 2 —, and

n 101 is 0 or 1.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 8, 2016
From: YAMAZAKI, HIROTO; KOMURO, YOSHITAKA; ARAI, MASATOSHI; KAWANA, DAISUKE; SUZUKI, KENTA; FUJII, TASUYA
To: TOKYO OHKA KOGYO CO., LTD.
Reel/Frame 039109/0282 →
Priority Claims (1)
JP 2015-129169 · Jun 26, 2015 · national
Continuity (1)
Related Publication 20160376233A1 · Dec 29, 2016