Resist composition, method for forming resist pattern, and polyphenol compound used therein

Patent metadata

Field	Value
Publication number	US-11480877-B2
Application number	US-201615560458-A
Country	US
Kind code	B2
Filing date	Mar 2, 2016
Priority date	Mar 31, 2015
Publication date	Oct 25, 2022
Grant date	Oct 25, 2022

Abstract

The present invention is a compound represented by the following general formula (1).

First claim

The invention claimed is:

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

wherein each X is independently an oxygen atom, or a sulfur atom; R 1 is a 2n-valent group of 1 to 30 carbon atoms; R 2 and R 3 are each independently a halogen atom, 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 thiol group, or a hydroxy group; each m is independently an integer of 0 to 7, provided that at least one m is an integer of 1 to 7; each p is 1; and n is an integer of 1 to 4; provided that R 1 is a group comprising an iodine atom, and at least one R 2 and/or at least one R 3 is one or more selected from a hydroxy group and a thiol group.

2. The compound according to claim 1 , wherein X is an oxygen atom in the above general formula (1).

3. The compound according to claim 1 , wherein at least one R 2 is a hydroxy group, and at least one R 3 is a hydroxy group, in the above general formula (1).

4. The compound according to claim 1 , wherein one R 2 is a hydroxy group, and one R 3 is a hydroxy group, in the above general formula (1).

5. The compound according to claim 1 wherein p is 1, and n is 1, in the above general formula (1).

6. The compound according to claim 1 , wherein the compound represented by the above general formula (1) is a xanthene compound represented by the following general formula (2):

wherein R 5 is a halogen atom, 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, and an alkoxy group of 1 to 30 carbon atoms, provided that R 5 is a monovalent group comprising an iodine atom.

7. The compound according to claim 1 , wherein the compound represented by the above general formula (1) is a xanthene compound represented by the following general formula (3):

wherein each R 6 is independently a halogen atom, 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 thiol group, or a hydroxy group, and k is an integer of 1 to 5, provided that at least one R 6 is a monovalent group comprising an iodine atom.

8. The compound according to claim 1 , wherein the compound represented by the above general formula (1) is a xanthene compound represented by the following formula (3-1):

9. A resin obtained by reacting the compound according to claim 1 with a crosslinking compound.

10. The resin according to claim 9 , wherein the crosslinking compound 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.

11. A resin having a structure represented by the following general formula (Z):

wherein each X is independently an oxygen atom, or a sulfur atom; R 1 is a 2n-valent group of 1 to 30 carbon atoms; R 2 and R 3 are each independently a halogen atom, 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 thiol group, or a hydroxy group; each Y is independently a single bond or a linear or branched alkylene group of 1 to 20 carbon atoms; each m 2 is independently an integer of 0 to 6, provided that at least one m 2 is an integer of 1 to 6; each p is 1; and n is an integer of 1 to 4; provided that R 1 is a group comprising an iodine atom, and at least one R 2 and/or at least one R 3 is one or more selected from a hydroxy group and a thiol group.

12. A resist composition comprising the compound according to claim 1 , and further comprising a solvent, an acid generating agent, and an acid crosslinking agent.

13. A method for forming a resist pattern, comprising the steps of coating a substrate with the resist composition according to claim 12 , thereby forming a resist film; exposing the formed resist film; and developing the exposed resist film.

14. A method for producing the compound according to claim 1 , comprising the step of reacting a compound represented by the following general formula (4) with an aldehyde of 1 to 19 carbon atoms in the presence of an acid catalyst, wherein the aldehyde comprises an iodine atom:

wherein each R 7 is independently a halogen atom or an alkyl group of 1 to 4 carbon atoms, and q is an integer of 0 to 5.

15. A method for producing the xanthene compound according to claim 6 , comprising the step of reacting a compound represented by the following general formula (5) with an aldehyde of 1 to 19 carbon atoms in the presence of an acid catalyst, wherein the aldehyde comprises an iodine atom:

16. A purification method comprising the steps of:
obtaining a solution (A) by dissolving the compound according to claim 1 or the resin according to claim 9 in a solvent; and
extracting impurities in the compound or the resin by bringing the obtained solution (A) into contact with an acidic aqueous solution (a first extraction step), wherein
the solvent used in the step of obtaining the solution (A) comprises an organic solvent that does not inadvertently mix with water.

17. The purification method according to claim 16 , 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.

18. The purification method according to claim 16 , wherein the organic solvent that does not inadvertently mix with water is one or more organic solvents selected from the group consisting of toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, and ethyl acetate.

19. The purification method according to claim 16 , comprising the step of extracting impurities in the compound or the resin by further bringing a solution phase comprising the compound or the resin into contact with water after the first extraction step (a second extraction step).

20. A resist composition comprising a resin formed using the compound of claim 1 , and further comprising a solvent, an acid genera

Assignees

• Mitsubishi Gas Chemical Co

Inventors

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

Classifications

• C07C39/17

  containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol} · CPC title

• C07C39/42

  containing six-membered aromatic rings and other rings · 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

• C07D311/96

  spiro-condensed with carbocyclic rings or ring systems · CPC title

• G03F7/327

  Non-aqueous alkaline compositions, e.g. anhydrous quaternary ammonium salts · CPC title