IP Library › Granted Patent US 9,541,831
Granted Patent B2
US 9,541,831 · App. 14/638,471 · Granted Jan 10, 2017

Positive resist composition and method of pattern formation with the same

Inventors: Hiromi Kanda (Shizuoka, JP); Shinichi Kanna (Shizuoka, JP); Haruki Inabe (Shizuoka, JP)
Assignee: FUJIFILM Corporation
G03F7/039G03F7/0046G03F7/0392G03F7/0397G03F7/2041G03F7/30G03F7/0045
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Quick Facts
Patent No.
US 9,541,831
App. No.
14/638,471
Granted
Jan 10, 2017
Kind
B2
Abstract

A positive resist composition comprising: (A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid; (B) a compound which generates an acid upon irradiation with actinic rays or a radiation; (C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z); and (F) a solvent, and a method of pattern formation with the composition: (x) an alkali-soluble group; (y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and (z) a group which decomposes by an action of an acid.

Claims (79)

1. A positive resist composition comprising:

(A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid;

(B) a compound which generates an acid upon irradiation with actinic rays or a radiation;

(C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z):

(x) an alkali-soluble group;

(y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and

(z) a group which decomposes by an action of an acid, and

(F) a solvent,

wherein the fluorine-containing compound (C) has an alcoholic hydroxyl group, and an alcohol moiety for the alcoholic hydroxyl group is a fluorinated alcohol,

the fluorine-containing compound (C) is an alkali-soluble compound containing an alkyl group having a fluorine atom and 1 to 4 carbon atoms, a cycloalkyl group having a fluorine atom or an aryl group having a fluorine atom,

the fluorine-containing compound (C) has a molecular weight of from 1,000 to 100,000,

the amount of the fluorine-containing compound (C) is from 0.1 to 10% by mass with respect to the total solid components in the positive resist composition, and

the total solids concentration in the positive resist composition is from 1.0 to 6.0% by mass.

2. The positive resist composition according to claim 1 ,

wherein the fluorine-containing compound (C) has a structure represented by formula (F3):

wherein R 62 and R 63 each independently represents a fluoroalkyl group, provided that R 62 and R 63 may be bonded to each other to form a ring; and

R 64 represents a hydrogen atom, a fluorine atom or an alkyl group.

3. The positive resist composition according to claim 1 ,

wherein the fluorine-containing compound (C) further comprises a group (y) which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution, wherein the group (y) has a lactone structure.

4. The positive resist composition according to claim 1 ,

wherein the amount of the fluorine-containing compound (C) is from 0.1 to 5% by mass.

5. The positive resist composition according to claim 1 , which provides a film with which water has a receding contact angle of 70° or larger.

6. The positive resist composition according to claim 1 ,

wherein the resin (A) contains a repeating unit having a polycyclic hydrocarbon group substituted by a hydroxyl group or a cyano group.

7. The positive resist composition according to claim 1 ,

wherein the resin (A) has no fluorine atom.

8. The positive resist composition according to claim 1 ,

wherein the compound (B) which generates an acid upon irradiation with actinic rays or a radiation is a compound which generates an acid having a fluoroalkyl chain or a benzenesulfonic acid having a fluorine atom upon irradiation with actinic rays.

9. The positive resist composition according to claim 1 ,

wherein the compound (B) which generates an acid upon irradiation with actinic rays or a radiation is a triphenylsulfonium salt compound having an alkyl or cycloalkyl residue which has not been substituted by fluorine in a cation part.

10. The positive resist composition according to claim 1 ,

wherein the solvent (F) is a mixed solvent comprising two or more solvents including propylene glycol monomethyl ether acetate.

11. The positive resist composition according to claim 1 , further comprising at least one of a fluorochemical surfactant and a silicone surfactant.

12. A resist film comprising a positive resist composition including:

(A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid;

(B) a compound which generates an acid upon irradiation with actinic rays or a radiation; and

(C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z):

(x) an alkali-soluble group;

(y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and

(z) a group which decomposes by an action of an acid,

wherein the fluorine-containing compound (C) has an alcoholic hydroxyl group, and an alcohol moiety for the alcoholic hydroxyl group is a fluorinated alcohol,

the fluorine-containing compound (C) is an alkali-soluble compound containing an alkyl group having a fluorine atom and 1 to 4 carbon atoms, a cycloalkyl group having a fluorine atom or an aryl group having a fluorine atom,

the fluorine-containing compound (C) has a molecular weight of from 1,000 to 100,000,

the amount of the fluorine-containing compound (C) is from 0.1 to 10% by mass with respect to the total solid components in the positive resist composition, and

the total solids concentration in the positive resist composition is from 1.0 to 6.0% by mass.

13. A pattern forming method, comprising:

exposing the resist film according to claim 12 ; and

developing the exposed resist film.

14. The pattern forming method according to claim 13 ,

wherein the exposing is an immersion exposure.

15. A method for filtrating a positive resist composition, comprising:

filtrating the composition using a filter,

wherein the positive resist composition contains:

(A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid;

(B) a compound which generates an acid upon irradiation with actinic rays or a radiation;

(C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z):

(x) an alkali-soluble group;

(y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and

(z) a group which decomposes by an action of an acid, and

(F) a solvent,

wherein the fluorine-containing compound (C) has an alcoholic hydroxyl group, and an alcohol moiety for the alcoholic hydroxyl group is a fluorinated alcohol,

the fluorine-containing compound (C) is an alkali-soluble compound containing an alkyl group having a fluorine atom and 1 to 4 carbon atoms, a cycloalkyl group having a fluorine atom or an aryl group having a fluorine atom,

the fluorine-containing compound (C) has a molecular weight of from 1,000 to 100,000,

the amount of the fluorine-containing compound (C) is from 0.1 to 10% by mass with respect to the total solid components in the positive resist composition, and

the total solids concentration in the positive resist composition is from 1.0 to 6.0% by mass.

16. A method for preparing a resist composition comprising the method for filtrating a composition according to claim 15 .

17. A positive resist composition comprising:

(A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid;

(B) a compound which generates an acid upon irradiation with actinic rays or a radiation;

(C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z):

(x) an alkali-soluble group;

(y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and

(z) a group which decomposes by an action of an acid, and

(F) a solvent,

wherein the fluorine-containing compound (C) has a structure represented by formula (F3):

wherein R 62 and R 63 each independently represents a fluoroalkyl group, provided that R 62 and R 63 may be bonded to each other to form a ring; and R 64 represents a hydrogen atom, a fluorine atom or an alkyl group,

the fluorine-containing compound (C) has a molecular weight of from 1,000 to 100,000,

the amount of the fluorine-containing compound (C) is from 0.1 to 10% by mass with respect to the total solid components in the positive resist composition, and

the total solids concentration in the positive resist composition is from 1.0 to 6.0% by mass.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2015
From: KOBAYASHI, HIROMI; KANNA, SHINICHI; INABE, HARUKI
To: FUJIFILM CORPORATION
Reel/Frame 035874/0070 →
Priority Claims (5)
JP 2005-215412 · Jul 26, 2005 · national
JP 2005-356714 · Dec 9, 2005 · national
JP 2006-7762 · Jan 16, 2006 · national
JP 2006-107727 · Apr 10, 2006 · national
JP 2006-198897 · Jul 21, 2006 · national
Continuity (3)
Continuation 13345978 · Jan 9, 2012
Continuation 11492123 · Jul 25, 2006
Related Publication 20150185609A1 · Jul 2, 2015