Compound, resin, resist composition or radiation-sensitive composition, resist pattern formation method, method for producing amorphous film, underlayer film forming material for lithography, composition for underlayer film formation for lithography, method for forming circuit pattern, and purification method

Patent metadata

Field	Value
Publication number	US-11243467-B2
Application number	US-201615759076-A
Country	US
Kind code	B2
Filing date	Sep 8, 2016
Priority date	Sep 10, 2015
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

The present invention employs a compound represented by the following formula (1) and/or a resin comprising the compound as a constituent:wherein R1 is a 2n-valent group of 1 to 60 carbon atoms or a single bond; R2 to R5 are each independently a linear, branched, or cyclic alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a halogen atom, a thiol group, a hydroxy group, or a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group, provided that at least one selected from R2 to R5 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group; m2 and m3 are each independently an integer of 0 to 8; m4 and m5 are each independently an integer of 0 to 9, provided that m2, m3, m4, and m5 are not 0 at the same time; n is an integer of 1 to 4; and p2 to p5 are each independently an integer of 0 to 2.

First claim

The invention claimed is:

1. A compound represented by the following formula (1):

wherein R 2 to R 5 are each independently a linear, branched, or cyclic alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a halogen atom, a thiol group, a hydroxy group, or a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group, provided that at least one selected from R 2 to R 5 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group; m 2 and m 3 are each independently an integer of 0 to 8; m 4 and m 5 are each independently an integer of 0 to 9, provided that m 2 , m 3 , m 4 , and m 5 are not 0 at the same time; n is an integer of 1 to 4; p 2 to p 5 are each independently an integer of 0 to 2; when is 1, R 1 includes at least one selected from the group consisting of a heterocyclic group or an aromatic group of 6 to 30 carbon atoms; and when n is 2, 3, or 4, R 1 is a 2n-valent group of 1 to 60 carbon atoms or a single bond.

2. The compound according to claim 1 , wherein at least one selected from the group consisting of R 4 and R 5 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group.

3. The compound according to claim 1 , wherein at least one selected from the group consisting of R 2 and R 3 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group.

4. A compound represented by the following formula (1):

wherein R 1 is a 2n-valent group of 1 to 60 carbon atoms or a single bond; R 2 to R 5 are each independently a linear, branched, or cyclic alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a halogen atom, a thiol group, a hydroxy group, or a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group, provided that at least one selected from R 2 to R 5 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group; m 2 and m 3 are each independently an integer of 0 to 8; m 4 and m 5 are each independently an integer of 0 to 9, provided that m 2 , m 3 , m 4 , and m 5 are not 0 at the same time; n is an integer of 1 to 4; and p 2 to p 5 are each independently an integer of 0 to 2, wherein at least one selected from the group consisting of R 1 to R 5 is a group containing an iodine atom.

5. The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1a):

wherein R 1 to R 5 and n are as defined in the description of the formula (1), provided that at least one selected from the group consisting of R 2 to R 5 is a group in which a hydrogen atom of a hydroxy group is replaced with an acid dissociation group; m 2′ and m 3′ are each independently an integer of 0 to 4; and m 4′ and m 5′ are each independently an integer of 0 to 5, provided that m 2′ , m 3′ , m 4′ , and m 5′ are not 0 at the same time.

6. A compound represented by the following formula (1b):

wherein R 1 is a 2n-valent group of 1 to 60 carbon atoms or a single bond; R 6 and R 7 are each independently a linear, branched, or cyclic alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a halogen atom, or a thiol group; each R 8 is independently a hydrogen atom or an acid dissociation group, provided that at least one R 8 is an acid dissociation group; and m 6 and m 7 are each independently an integer of 0 to 7.

7. The compound according to claim 6 , wherein the compound represented by the formula (1b) is a compound represented by the following formula (1c):

wherein R 8 is as defined in the description of the formula (1b); and each R 9 is independently a hydrogen atom, a cyano group, a nitro group, a heterocyclic group, a halogen atom, a linear aliphatic hydrocarbon group of 1 to 20 carbon atoms, a branched aliphatic hydrocarbon group of 3 to 20 carbon atoms, a cyclic aliphatic hydrocarbon group of 3 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a thiol group, or a hydroxy group, provided that at least one R 8 is an acid dissociation group.

8. The compound according to claim 7 , wherein the compound represented by the formula (1c) is a compound represented by the following formula (1d):

wherein R 8 is as defined in the description of the formula (1b); each R 10 is independently a cyano group, a nitro group, a heterocyclic group, a halogen atom, a linear aliphatic hydrocarbon group of 1 to 20 carbon atoms, a branched aliphatic hydrocarbon group of 3 to 20 carbon atoms, a cyclic aliphatic hydrocarbon group of 3 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an alkoxy group of 1 to 30 carbon atoms, a thiol group, or a hydroxy group; and m 9 is an integer of 0 to 4, provided that at least one R 8 is an acid dissociation group.

9. A resist composition comprising the compound according to claim 1 and an acid generating agent.

10. The resist composition according to claim 9 , further comprising a solvent.

11. The resist composition according to claim 10 , further comprising an acid diffusion controlling agent.

12. A purification method comprising the steps of:
obtaining a solution (S) by dissolving the compound according to claim 1 in a solvent; and
extracting impurities in the compound and/or the resin by bringing the obtained solution (S) into contact with an acidic aqueous solution (a first extraction step), wherein
the solvent used in the step of obtaining the solution (S) comprises a solvent that does not inadvertently mix with water.

13. The purification method according to claim 12 , wherein
the acidic aqueous solution is an aqueous mineral acid solution or an aqueous organic acid solution;
the aqueous mineral acid solution is one or more aqueous mineral acid solutions selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid; and
the aqueous organic acid solution is one or more aqueous organic acid solutions selected from the group consisting of acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, tartaric acid, citric acid, methanesulfonic acid, phenolsulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Toida Takumi
• Shimizu Youko
• Makinoshima Takashi
• Sato Takashi
• Echigo Masatoshi

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• C08G8/28

  Chemically modified polycondensates · 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

• C08G8/14 Primary

  with halogenated phenols · CPC title

• G03F7/0226 Primary

  characterised by the non-macromolecular additives · CPC title