IP Library Granted Patent US 8,476,401
Granted Patent B2
US 8,476,401 · App. 11/574,860 · Granted Jul 2, 2013

Resist polymer, process for production thereof, resist composition, and process for production of substrated with patterns thereon

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Quick Facts
Patent No.
US 8,476,401
App. No.
11/574,860
Granted
Jul 2, 2013
Kind
B2
Abstract

A resist polymer (Y′), which is used as a resist resin in DUV excimer laser lithography, electron beam lithography, and the like, contains a polymer (Y) comprising: a constituent unit (A) having a lactone skeleton; a constituent unit (B) having an acid-eliminable group; a constituent unit (C) having a hydrophilic group; and a constituent unit (E) having a structure represented by the following formula (1), wherein a content of the constituent unit (E) is 0.3 mol % or more based on the total number of the constituent units of the resist polymer (Y′): in the formula (1), L is a divalent linear, branched, or cyclic C 1-20 hydrocarbon group which may have a substituent and/or a heteroatom; R 11 is a g-valent linear, branched, or cyclic C 1-20 hydrocarbon group which may have a substituent and/or a heteroatom; and g represents an integer of 1 to 24.

Claims (37)

1. A resist polymer (Y′) comprising a polymer (Y) comprising:

a constituent unit (A) having a lactone skeleton;

a constituent unit (B) having an acid-eliminable group;

a constituent unit (C) having a hydrophilic group; and

a constituent unit (E) having a structure represented by formula (1),

wherein

a content of the constituent unit (E) is 0.3 mol % or more based on the total number of the constituent units of the resist polymer (Y′):

where

L is a divalent linear, branched, or cyclic C 1-20 hydrocarbon group which may have a substituent, a heteroatom, or a combination thereof;

g is 3 to 24

R 11 is a g-valent linear, branched, or cyclic C 1-12 hydrocarbon group, optionally having a substituent, a heteroatom, or a combination thereof,

wherein

the constituent unit (A) is selected from the group consisting of formulae (4-2), (4-3), (4-4), and (10-1)

wherein,

in the formula (4-2), R 42 represents a hydrogen atom or a methyl group; R 201 and R 202 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; A 1 and A 2 independently represents a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or A 1 and A 2 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain [—(CH 2 ) k — (wherein k represents an integer of 1 to 6)]; X 6 represents a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, a C 1-6 acyl group, a C 1-6 alkoxy group, a carboxy group esterified with C 1-6 alcohol, a cyano group, or an amino group; the linear or branched C 1-6 alkyl group may have, as a substituent, at least one group selected from a group consisting of a hydroxy group, a carboxy group, a C 1-6 acyl group, a carboxy group esterified with C 1-6 alcohol, a cyano group, and an amino group; n6 represents an integer of 0 to 4; and X 6 may have a plurality of different groups if n6 is 2 or more;

in the formula (4-3), R 43 represents a hydrogen atom or a methyl group; R 203 and R 204 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; A 3 and A 4 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or A 3 and A 4 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain, [—(CH 2 ) 1 — (wherein 1 represents an integer of 1 to 6)], X 7 represents a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, a C 1-6 acyl group, a C 1-6 alkoxy group, a carboxy group esterified with C 1-6 alcohol, a cyano group, or an amino group; the linear or branched C 1-6 alkyl group may have, as a substituent, at least one group selected from a group consisting of a hydroxy group, a carboxy group, a C 1-6 acyl group, a carboxy group esterified with C 1-6 alcohol, a cyano group, and an amino group; n7 represents an integer of 0 to 4; and X 7 may have a plurality of different groups if n7 is 2 or m

in the formula (4-4), R 91 , R 92 , R 93 , and R 94 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or R 91 and R 92 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain [—(CH 2 ) t — (wherein t represents an integer of 1 to 6)]; and m1 represents 1 or 2; and

in the formula (10-1), R represents a hydrogen atom or a methyl group.

2. A resist polymer (Y′) comprising a polymer (Y) comprising:

a constituent unit (A) having a lactone skeleton;

a constituent unit (B) having an acid-eliminable group;

a constituent unit (C) having a hydrophilic group; and

a constituent unit (E) having a structure represented by formula (1),

wherein

the polymer (Y) comprises (meth)acrylic monomers;

a content of the constituent unit (A) is 30 mol % or more based on the total number of constituent units of the resist polymer (Y′); and

a content of the constituent unit (E) is 0.3 mol % or more based on the total number of the constituent units of the resist polymer (Y′):

where

L is a divalent linear, branched, or cyclic C 1-20 hydrocarbon group which may have a substituent, a heteroatom, or a combination thereof;

g is 3 to 24

R 11 is a g-valent linear, branched, or cyclic C 1-12 hydrocarbon group, optionally having a substituent, a heteroatom, or a combination thereof, wherein

the constituent unit (A) is selected from the group consisting of formulae (4-2), (4-3), (4-4), and (10-1)

wherein,

in the formula (4-2), R 42 represents a hydrogen atom or a methyl group; R 201 and R 202 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; A 1 and A 2 independently represents a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or A 1 and A 2 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain [—(CH 2 ) k — (wherein k represents an integer of 1 to 6)]; X 6 represents a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, a C 1-6 acyl group, a C 1-6 alkoxy group, a carboxy group esterified with C 1-6 alcohol, a cyano group, or an amino group; the linear or branched C 1-6 alkyl group may have, as a substituent, at least one group selected from a group consisting of a hydroxy group, a carboxy group, a C 1-6 acyl group, a carboxy group esterified with C 1-6 alcohol, a cyano group, and an amino group; n6 represents an integer of 0 to 4; and X 6 may have a plurality of different groups if n6 is 2 or more;

in the formula (4-3), R 43 represents a hydrogen atom or a methyl group; R 203 and R 204 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; A 3 and A 4 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or A 3 and A 4 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain, [—(CH 2 ) 1 — (wherein 1 represents an integer of 1 to 6)], X 7 represents a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, a C 1-6 acyl group, a C 1-6 alkoxy group, a carboxy group esterified with C 1-6 alcohol, a cyano group, or an amino group; the linear or branched C 1-6 alkyl group may have, as a substituent, at least one group selected from a group consisting of a hydroxy group, a carboxy group, a C 1-6 acyl group, a carboxy group esterified with C 1-6 alcohol, a cyano group, and an amino group; n7 represents an integer of 0 to 4; and X 7 may have a plurality of different groups if n7 is 2 or m

in the formula (4-4), R 91 , R 92 , R 93 , and R 94 independently represent a hydrogen atom, a linear or branched C 1-6 alkyl group, a hydroxy group, a carboxy group, or a carboxy group esterified with C 1-6 alcohol; or R 91 and R 92 together represent —O—, —S—, —NH—, or a C 1-6 methylene chain [—(CH 2 ) t — (wherein t represents an integer of 1 to 6)]; and m1 represents 1 or 2; and

in the formula (10-1), R represents a hydrogen atom or a methyl group.

Assignments (2)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2013
From: MOMOSE, HIKARU; UEDA, AKIFUMI
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 030482/0766 →