Resist material, resist composition and method for forming resist pattern

Patent metadata

Field	Value
Publication number	US-10437148-B2
Application number	US-201515309780-A
Country	US
Kind code	B2
Filing date	May 8, 2015
Priority date	May 8, 2014
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

wherein each R0 is independently a monovalent group having an oxygen atom, a monovalent group having a sulfur atom, a monovalent group having a nitrogen atom, a hydrocarbon group, or a halogen atom; and each p is independently an integer of 0 to 4.

First claim

The invention claimed is:

1. A resist material comprising a compound represented by the following formula (3):

wherein each R is independently a hydrogen atom or an acid dissociation reactive group, wherein at least one of R is an acid dissociation reactive group; and each n is independently an integer of 0 to 4, wherein at least one of n is an integer of 1 to 4, wherein the acid dissociation reactive group is a group selected from the group consisting of the following:

wherein R 5 is a hydrogen atom, or a linear or branched alkyl group haying 1 to 4 carbon atoms; R 6 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, a heterocyclic group, a halogen atom, or a carboxyl group; n 1 is an integer of 0 to 4; n 2 is an integer of 1 to 5; and n 0 is an integer of 0 to 4.

2. A resist composition comprising:
a resin obtained through a reaction of at least a compound represented by the following formula (1) with a compound having crosslinking reactivity:

wherein each R 0 is independently a monovalent group having an oxygen atom, a monovalent group having a sulfur atom, a monovalent group having a nitrogen atom, a hydrocarbon group, or a halogen atom; and each p is independently an integer of 0 to 4; and
at least one of an acid generating agent and an acid crosslinking agent.

3. The resist composition according to claim 2 , wherein the compound having crosslinking reactivity is an aldehyde, a ketone, a carboxylic acid, a carboxylic acid halide, a halogen-containing compound, an amino compound, an imino compound, an isocyanate, or an unsaturated hydrocarbon group-containing compound.

4. The resist composition according to claim 2 , wherein the resin is at least one kind selected from the group consisting of a novolac-based resin, an aralkyl-based resin, a hydroxystyrene-based resin, a (meth)acrylic acid-based resin, and a copolymer thereof.

5. The resist composition according to claim 2 , wherein the resin has at least one structure selected from the group consisting of structures represented by the following formulas (4-1) to (4-16):

wherein R 0 and p are as defined in the formula (1).

6. A resist composition comprising:
a resist material including a compound represented by the following formula (3)

wherein each R is independently a hydrogen atom or an acid dissociation reactive group, wherein at least one of R is an acid dissociation reactive group; and each n is independently an integer of 0 to 4, wherein at least one of n is an integer of 1 to 4, wherein the acid dissociation reactive group is a group selected from the group consisting of the following:

wherein R 5 is a hydrogen atom, or a linear or branched alkyl group having 1 to 4 carbon atoms; R 6 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, a heterocyclic group, a halogen atom, or a carboxyl group; n 1 is an integer of 0 to 4; n 2 is an integer of 1 to 5; and n 0 is an integer of 0 to 4;
a solvent; and
an acid generating agent.

7. A resist composition comprising:
a resist material including a compound represented by the following formula (3)

wherein each R is independently a hydrogen atom or an acid dissociation reactive group, wherein at least one of R is an acid dissociation reactive group; and each n is independently an integer of 0 to 4, wherein at least one of n is an integer of 1 to 4, wherein the acid dissociation reactive group is a group selected from the group consisting of the following:

wherein R 5 is a hydrogen atom, or a linear or branched alkyl group having 1 to 4 carbon atoms; R 6 is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a cyano group, a nitro group, a heterocyclic group, a halogen atom, or a carboxyl group; n 1 is an integer of 0 to 4; n 2 is an integer of 1 to 5; and n 0 is an integer of 0 to 4;
a solvent; and
an acid crosslinking agent.

8. A method for forming a resist pattern, comprising the steps of:
coating a substrate with the resist composition according to claim 6 , thereby forming a resist film;
exposing the resist film; and
developing the exposed resist film.

9. A method for forming a resist composition comprising the steps of:
obtaining a resist material comprising a compound represented by the following formula (1)

wherein each R 0 is independently a monovalent group having an oxygen atom, a monovalent group having a sulfur atom, a monovalent group having a nitrogen atom, a hydrocarbon group, or a halogen atom; and each p is independently an integer of 0 to 4; and
forming the resist composition from the resist material and at least one of an acid generating agent and an acid crosslinking agent;
wherein at least one p is an integer of 1 to 4.

10. The method of claim 9 , wherein at least one of R 0 is the monovalent group having the oxygen atom.

11. The method of claim 9 , wherein the compound represented by the formula (1) is a compound represented by the following formula (2):

wherein each m is independently an integer of 0 to 4, wherein at least one of m is an integer of 1 to 4.

12. The method of claim 11 , wherein the compound represented by the formula (2) is at least one kind selected from a compound group represented by the following formulas (2-1) to (2-6):

13. The method of claim 9 , wherein the compound represented by the formula (1) is a compound represented by the following formula (3):

wherein each R is independently a hydrogen atom or an acid dissociation reactive group, wherein at least one of R is an acid dissociation reactive group; and each n is independently an integer of 0 to 4, wherein at least one of n is an integer of 1 to 4.

14. The method of claim 13 , wherein the compound represented by the formula (3) is at least one kind selected from a compound group rep

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Toida Takumi
• Sato Takashi
• Echigo Masatoshi

Classifications

• H10P76/00

  Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography · CPC title

• C08G8/14

  with halogenated phenols · CPC title

• C08G8/24

  with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20 · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C08G8/18

  with phenols substituted by carboxylic or sulfonic acid groups · CPC title