IP Library Granted Patent US 7,125,640
Granted Patent B2
US 7,125,640 · App. 10/356,775 · Granted Oct 24, 2006

Resist for photolithography having reactive groups for subsequent modification of the resist structures

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Quick Facts
Patent No.
US 7,125,640
App. No.
10/356,775
Granted
Oct 24, 2006
Kind
B2
Abstract

A photoresist contains a polymer that has no silicon-containing groups. Consequently, no expulsion of silicon-containing compounds in gaseous form occurs on exposure to short-wave radiation. The polymer is obtained by terpolymerization of a first comonomer having a group cleavable under acid catalysis, a second comonomer having an anchor group, and a monounsaturated hydrocarbon, in which individual carbon atoms of the carbon skeleton may also be replaced by oxygen, as a third comonomer. The polymer has a low glass transition temperature, and the photoresist therefore has a good layer quality on film formation and good structurability.

Claims (42)

1. A chemically amplified photoresist, comprising:

a film-forming polymer obtained by copolymerizing:

a first comonomer having a group cleavable under acid catalysis, said group being selected from the group consisting of a monocyclic alkyl group, a straight-chain alkyl group, and a branched alkyl group,

a second comonomer having an anchor group for binding amplification agents, and

a third comonomer having a non-vinylic carbon-carbon double bond capable of free radical polymerization and formed by a moiety selected from the group consisting of a straight-chain alkene and a branched alkene, said alkene of said third comonomer of said film-forming polymer having a carbon atom replaced by an oxygen atom;

a photo acid generator; and

a solvent.

2. A chemically amplified photoresist, comprising:

a film-forming polymer obtained by copolymerizing:

a first comonomer having a group cleavable under acid catalysis, said group being selected from the group consisting of a monocyclic alkyl group, a straight-chain alkyl group, and a branched alkyl group,

a second comonomer having an anchor group for binding amplification agents, and

a third comonomer having a non-vinylic carbon-carbon double bond capable of free radical polymerization and formed by a moiety selected from the group consisting of a straight-chain alkene and a branched alkene, said third comonomer being selected from the group consisting of a straight-chain hydrocarbon and a branched hydrocarbon, said straight-chain hydrocarbon and said branched hydrocarbon each including a respective non-terminal polymerizable carbon-carbon double bond;

a photo acid generator; and

a solvent.

3. A chemically amplified photoresist, comprising:

a film-forming polymer obtained by copolymerizing;

a first comonomer having a group cleavable under acid catalysis, said group being selected from the group consisting of a monocyclic alkyl group, a straight-chain alkyl group, and a branched alkyl group,

a second comonomer having an anchor group for binding amplification agents, and

a third comonomer having a non-vinylic carbon-carbon double bond capable of free radical polymerization and formed by a moiety selected from the group consisting of a straight-chain alkene and a branched alkene, said third comonomer being an ether with an oxygen forming an ether bond and having a monounsaturated alkenyl radical bonded to said oxygen of said ether bond, and a substituent further bonded to said oxygen of said ether bond and selected from the group consisting of a straight-chain alkyl radical, branched alkyl radical, and alkoxyalkylene radical;

a photo acid generator; and

a solvent.

4. The chemically amplified photoresist according to claim 3 , wherein said monounsaturated alkenyl radical is an allyl radical.

5. The chemically amplified photoresist according to claim 3 , wherein:

said ether has a structure of CH 2 ═CR 1 —R 2 —O—R 3 ;

R 1 is a substituent selected from the group consisting of a hydrogen atom, a methyl group, and a cyano group;

R 2 is a substituent selected from the group consisting of a single bond, a divalent linear alkylene group having from one to ten carbon atoms, and a divalent branched alkylene group having from one to ten carbon atoms, R 2 not being said single bond when R 1 is said hydrogen atom; and

R 3 is a monovalent alkyl group having from one to ten carbon atoms.

6. A chemically amplified photoresist, comprising:

a film-forming polymer obtained by copolymerizing:

a first comonomer having a group cleavable under acid catalysis, said group being selected from the group consisting of a monocyclic alkyl group, a straight-chain alkyl group, and a branched alkyl group,

a second comonomer having an anchor group for binding amplification agents, said anchor group of said second comonomer being a carboxylic anhydride group that is nucleophilically attackable, and

a third comonomer having a non-vinylic carbon-carbon double bond capable of free radical polymerization and formed by a moiety selected from the group consisting of a straight-chain alkene and a branched alkene;

a photo acid generator; and

a solvent.

7. The chemically amplified photoresist according to claim 6 , wherein said carboxylic anhydride group of said second comonomer is selected from the group consisting of a maleic anhydride, an itaconic anhydride, a cyclohexenedicarboxylic anhydride, a norbornenedicarboxylic anhydride, and a methacrylic anhydride.

8. A chemically amplified photoresist, comprising:

a film-forming polymer obtained by copolymerizing:

a first comonomer having a group cleavable under acid catalysis, said group being selected from the group consisting of a monocyclic alkyl group, a straight-chain alkyl group, and a branched alkyl group,

a second comonomer having an anchor group for binding amplification agents, and

a third comonomer having a nonvinylic carbon-carbon double bond capable of free radical polymerization and formed by a moiety selected from the group consisting of a straight-chain alkene and a branched alkene; said third comonomer being an ether with an oxygen forming an ether bond and having a monounsaturated alkenyl radical bonded to said oxygen of said ether bond, and a substituent further bonded to said oxygen of said ether bond and selected from the group consisting of a straight-chain alkyl radical and a branched alkyl radical; said ether having a structure of CH 2 ═CR 1 —R 2 —O—R 3 ; R 1 being a substituent selected from the group consisting of a hydrogen atom, a methyl group, and a cyano group; R 2 being a substituent selected from the group consisting of a single bond, a divalent linear alkylene group having from one to ten carbon atoms, and a divalent branched alkylene group having from one to ten carbon atoms, R 2 not being said single bond when R 1 is said hydrogen atom; and R 3 being a monovalent alkyl group having from one to ten carbon atoms;

a photo acid generator; and

a solvent.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2015
From: INFINEON TECHNOLOGIES AG
To: POLARIS INNOVATIONS LIMITED
Reel/Frame 036818/0583 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2015
From: QIMONDA AG
To: INFINEON TECHNOLOGIES AG
Reel/Frame 035623/0001 →