Iodine-containing polymers for chemically amplified resist compositions

Patent metadata

Field	Value
Publication number	US-2018362752-A1
Application number	US-201715623892-A
Country	US
Kind code	A1
Filing date	Jun 15, 2017
Priority date	Jun 15, 2017
Publication date	Dec 20, 2018
Grant date	—

Abstract

A monomer having formula (I):

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

First claim

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 4-20 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 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.

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; X is a hydroxyl group; and n is 1, 2, or 3.

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

wherein
each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl; and
each R b is independently 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.

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 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;
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

Assignees

• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Thackeray James W
• Cameron James F

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0392

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

• C08L27/10 Primary

  containing bromine or iodine atoms · CPC title