Iodine-containing polymers for chemically amplified resist compositions

Patent metadata

Field	Value
Publication number	US-10901316-B2
Application number	US-201916681142-A
Country	US
Kind code	B2
Filing date	Nov 12, 2019
Priority date	Jun 15, 2017
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

A monomer having formula (I):

wherein in formula (I), groups and variables are the same as described in the specification.

First claim

The invention claimed is:

1. A monomer having formula (I):

wherein in formula (I):
W is —(C═O)O—, —O(C═O)—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, —SO—,
R a is H, F, —CN, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
L is a linking group selected from an unsubstituted or substituted C 1-20 alkylene group, an unsubstituted or substituted C 3-20 cycloalkylene group, an unsubstituted or substituted C 6-20 arylene group, and an unsubstituted or substituted C 7-20 aralkylene group;

represents a monocyclic or polycyclic unsubstituted or substituted C 6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C 3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
“I” represents iodine;
X is selected from —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, an unsubstituted or substituted C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group,
wherein at least one X comprises —C(CF 3 ) 2 OH;
m is an integer of 1 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring; and
n is an integer of 1 or greater.

2. The monomer of claim 1 , wherein
L is an unsubstituted C 1-20 alkylene group or a C 1-20 alkylene group substituted with —F, a hydroxyl group, or a C 1-10 alkyl group; and
n is 1, 2, or 3.

3. A copolymer comprising a polymerized product of an acid-deprotectable monomer and a monomer having formula (I):

wherein in formula (I):
W is —(C═O)O—or —O(C═O)—,
R a is H, F, —CN, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
L is a linking group selected from an unsubstituted or substituted C 1-20 alkylene group, an unsubstituted or substituted C 3-20 cycloalkylene group, an unsubstituted or substituted C 6-20 arylene group, and an unsubstituted or substituted C 7-20 aralkylene group;

represents a monocyclic or polycyclic unsubstituted or substituted C 6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C 3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
“I” represents iodine;
X is selected from —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, an unsubstituted or substituted C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 3-30 heterocycloalkyl group, an unsubstituted or substituted C 4-30 cycloalkenyl group, an unsubstituted or substituted C 4-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 4-30 heteroaryl group, an unsubstituted or substituted C 4-30 heteroaryloxy group, an unsubstituted or substituted C 4-30 heteroarylthio group, or an unsubstituted or substituted C 5-30 heteroarylalkyl group,
wherein X optionally comprises an ester group or —C(CF 3 ) 2 OH;
m is an integer of 0 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring; and
n is an integer of 1 or greater.

4. The copolymer of claim 3 , further comprising a polymerized product of a base-soluble monomer, a lactone-containing monomer, a photoacid generator, or a combination thereof.

5. The copolymer of claim 4 , wherein the acid-deprotectable monomer is represented by formula (II), the base-soluble monomer is represented by formula (III), the lactone-containing monomer is represented by formula (IV), and the photoacid generator is represented by formula (V):

wherein each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
each R b is independently H, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 3-20 cycloalkyl group, an unsubstituted or substituted C 6-20 aryl group, or an unsubstituted or substituted C 7-20 aralkyl group, and each R b is separate or at least one R b is bonded to an adjacent R b to form a cyclic structure;
Q 1 is an ester-containing or non-ester containing group selected from an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 3-20 cycloalkyl group, an unsubstituted or substituted C 6-20 aryl group, and an unsubstituted or substituted C 7-20 aralkyl group;
W is a base-reactive group comprising at least one selected from —C(═O)—OH; —C(CF 3 ) 2 OH; —NH—SO 2 —Y 1 where Y 1 is F or a C 1-4 perfluoroalkyl group; an aromatic —OH; and an adduct of any of the foregoing with a vinyl ether;
a is an integer of 1 to 3;
L is a monocyclic, polycyclic, or fused polycyclic C 4-20 lactone-containing group;
Q 2 is a single bond or an ester-containing or non-ester containing, fluorinated or non-fluorinated group selected from a C 1-20 alkylene group, a C 3-20 cycloalkylene group, a C 6-20 arylene group, and a C 7-20 aralkylene group;
A is an ester-containing or non ester-containing, fluorinated or non-fluorinated group selected from a C 1-20 alkylene group, a C 3-20 cycloalkylene group, a C 6-20 arylene group, and a C 7-20 aralkylene group;
Z is an anionic moiety comprising sulfonate, an anion of a sulfonamide, or an anion of a sulfonimide; and
G + has formula (VI):

wherein
X is S or I,
each R C is unsubstituted or substituted, halogenated or non-halogenated and is independently a C 1-30 alkyl group; a polycyclic or monocyclic C 3-30 cycloalkyl group; a polycyclic or monocyclic C 4

Assignees

• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Thackeray James W
• Cameron James F

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08F220/283

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title

• G03F7/0045 Primary

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

• G03F7/2002

  with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image · CPC title