Polymer, monomer, resist composition, and patterning process

Patent metadata

Field	Value
Publication number	US-9790166-B2
Application number	US-201615156411-A
Country	US
Kind code	B2
Filing date	May 17, 2016
Priority date	May 19, 2015
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

A pattern forming process is provided comprising the steps of applying a resist composition comprising a polymer comprising recurring units having formula (1a) and/or (1b), an acid generator and a solvent onto a substrate, baking to form a resist film, exposing the resist film to high-energy radiation, baking, and developing in an alkaline developer to form a negative tone pattern.

First claim

The invention claimed is:

1. A polymer comprising recurring units having the formula (1a) and/or (1b) and recurring units having the formula (1c):

wherein R 1 is hydrogen or methyl, R 2 and R 3 are each independently a straight, branched or cyclic C 1 -C 6 monovalent hydrocarbon group, R 2 and R 3 may bond together to form an alicyclic group with the carbon atom to which they are attached, X a and X b are each independently a single bond, methylene or ethylidene, Z a is a branched or cyclic C 1 -C 9 divalent aliphatic hydrocarbon group, Z b is an atomic group necessary to form a C 3 -C 10 alicyclic group with the carbon atoms to which it is attached, with the proviso that the total number of carbon atoms in each formula is such as to meet 6≦X a +Z a +R 2 +R 3 ≦12 when Z a is acyclic, or 5≦X a +Z a +R 2 +R 3 ≦12 when Z a is cyclic, and 5≦X b +Z b +R 2 ≦12,
R 4 and R 5 are each independently a straight, branched or cyclic C 1 -C 10 monovalent hydrocarbon group, R 4 and R 5 may bond together to form an alicyclic group with the carbon atom to which they are attached, X 1 is a straight, branched or cyclic C 1 -C 20 divalent hydrocarbon group in which any constituent —CH 2 — moiety may be replaced by —O— or —C(═O)—, Z 1 is a straight, branched or cyclic C 1 -C 20 tri- to pentavalent aliphatic hydrocarbon group in which any constituent —CH 2 — moiety may be replaced by —O— or —C(═O)—, k 1 is 0 or 1, and k 2 is an integer of 2 to 4.

2. The polymer of claim 1 wherein the straight, branched or cyclic C 1 -C 20 tri- to pentavalent aliphatic hydrocarbon group represented by Z 1 is selected from the group consisting of the following formulae:

3. A polymer comprising recurring units having the formula (1a) and/or (1b) and recurring units of at least one type selected from the formulae (A), (B) and (D):

wherein R 1 is hydrogen or methyl, R 2 and R 3 are each independently a straight, branched or cyclic C 1 -C 6 monovalent hydrocarbon group, R 2 and R 3 may bond together to form an alicyclic group with the carbon atom to which they are attached, X a and X b are each independently a single bond, methylene or ethylidene, Z a is a branched or cyclic C 1 -C 9 divalent aliphatic hydrocarbon group, Z b is an atomic group necessary to form a C 3 -C 10 alicyclic group with the carbon atoms to which it is attached, with the proviso that the total number of carbon atoms in each formula is such as to meet 6≦X a +Z a +R 2 +R 3 ≦12 when Z a is acyclic, or 5≦X a +Z a +R 2 +R 3 ≦12 when Z a is cyclic, and 5≦X b +Z b +R 2 ≦12,
wherein the C 3 -C 10 alicyclic group is selected from the group consisting of the following formulae:

wherein the broken line denotes a valence bond,

wherein R 1 is hydrogen or methyl, Z A is a C 1 -C 20 fluoroalcohol-containing group, Z B is a C 1 -C 20 phenolic hydroxyl-containing group, Z D is a group containing a lactone structure, sultone structure, carbonate structure, acid anhydride structure, alkoxycarbonyl moiety, sulfonamide moiety or carbamoyl moiety, X 2 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, naphthylene, —O—R 01 —, or —C(═O)—Z 2 —R 01 —, Z 2 is oxygen or NH, R 01 is a straight, branched or cyclic C 1 -C 6 alkylene, straight, branched or cyclic C 2 -C 6 alkenylene, phenylene or naphthylene group, which may contain a carbonyl, ester, ether or hydroxyl moiety,
wherein the recurring unit of formula (B) is selected from the group consisting of the following formulae:

4. The polymer of claim 3 , further comprising recurring units having the formula (1c):

wherein R 1 is hydrogen or methyl, R 4 and R 5 are each independently a straight, branched or cyclic C 1 -C 10 monovalent hydrocarbon group, R 4 and R 5 may bond together to form an alicyclic group with the carbon atom to which they are attached, X 1 is a straight, branched or cyclic C 1 -C 20 divalent hydrocarbon group in which any constituent —CH 2 — moiety may be replaced by —O— or —C(═O)—, Z 1 is a straight, branched or cyclic C 1 -C 20 tri- to pentavalent aliphatic hydrocarbon group in which any constituent —CH 2 — moiety may be replaced by —O— or —C(═O)—, k 1 is 0 or 1, and k 2 is an integer of 2 to 4.

5. The polymer of claim 3 , further comprising recurring units of at least one type selected from the formulae (f1) to (f3):

wherein R 11 is independently hydrogen or methyl, R 12 is a single bond, phenylene, —O—R 21 —, or —C(═O)—Z 22 —R 21 —, Z 22 is oxygen or NH, R 21 is a straight, branched or cyclic C 1 -C 6 alkylene, straight, branched or cyclic C 2 -C 6 alkenylene or phenylene group, which may contain a carbonyl (—CO—), ester (—COO—), ether (—O—) or hydroxyl moiety, L is a single bond or —Z 33 —C(═O)—O—, Z 33 is a straight, branched or cyclic C 1 -C 20 divalent hydrocarbon group which may be substituted with a heteroatom, Z 11 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—R 22 —, or —C(═O)—Z 44 —R 22 —, Z 44 is oxygen or NH, R 22 is a straight, branched or cyclic C 1 -C 6 alkylene, straight, branched or cyclic C 2 -C 6 alkenylene or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl moiety, R 13 to R 20 are each independently a straight, branched or cyclic C 1 -C 20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, and M − is a non-nucleophilic counter ion.

6. A resist composition comprising a base resin comprising the polymer of claim 5 , and an organic solvent.

7. A resist composition comprising a base resin comprising the polymer of claim 3 , an acid generator, and an organic solvent.

8. The polymer of claim 3 wherein X a is a single bond, and Z a is a branched or cyclic C 1 -C 9 divalent aliphatic hydrocarbon group.

9. The polymer of claim 3 wherein the branched or cyclic C 1 -C 9 divalent aliphatic hydrocarbon group represented by Z a is selected from the group consisting of the following formulae:

Assignees

• Shinetsu Chemical Co

Inventors

• Sagehashi Masayoshi
• Hasegawa Koji
• Fukushima Masahiro
• Hatakeyama Jun
• Katayama Kazuhiro

Classifications

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F224/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F218/00; cyclic anhydrides of unsaturated acids C08F220/00, C08F222/00) · CPC title

• G03F7/0382 Primary

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• C08F216/10

  Carbocyclic compounds · CPC title

• C07C2601/14

  The ring being saturated · CPC title