# US 11,299,572 B2 · Block copolymer

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- Number: US 11,299,572 B2
- Document ID: US11299572B2
- Status: Granted
- Kind: B2
- Application number: 16/463,616
- Filed: 2017-11-29
- Published: 2020-04-30
- Granted: 2022-04-12
- Earliest claimed: 2016-11-30
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Je Gwon Lee; No Jin Park; Jung Keun Kim; Eun Young Choi; Se Jin Ku; Mi Sook Lee; Hyung Ju Ryu; Sung Soo Yoon
- Web page: https://patentgrep.com/patent/US11299572B2

## CPC

- C08F 230/085: {the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes}
- C08F 220/301: {and one oxygen in the alcohol moiety}
- C08F 293/005: {using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent}
- C08J 5/18: Manufacture of films or sheets
- C09D 153/00: Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- G03F 1/00: Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- H10P 50/28: of insulating materials
- H10P 76/00: Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
- C08F 212/20: {Fluorine}
- C08F 230/08: containing silicon
- C08F 2438/03: Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

The present application can provide a block copolymer and a use thereof. The block copolymer of the present application can have excellent self-assembly properties or phase separation characteristics and excellent etching selectivity, and various other functions as required can be freely imparted thereto.

## Claims

### Claim 1

A block copolymer comprising a polymer segment A having a unit represented by Formula 1 below and a polymer segment B different from the polymer segment A:
wherein, R is hydrogen or an alkyl group having 1 to 4 carbon atoms, X is an oxygen atom, —C(═O)—X1— or —X1—C(═O)—, where X1 is an oxygen atom or —SiH2—, and Y is a monovalent substituent comprising an aromatic ring structure to which a linear hydrocarbon chain having 8 or more chain-forming atoms is linked, where a carbon atom of the linear hydrocarbon chain is optionally replaced with oxygen, nitrogen or sulfur, and the linear hydrocarbon chain is substituted with a hydrocarbon functional group containing one or more silicon atoms or iron atoms.

### Claim 2 (depends on 1)

The block copolymer according to claim 1, wherein X is an oxygen atom, —C(═O)—O— or —O—C(═O)—.

### Claim 3 (depends on 1)

The block copolymer according to claim 1, wherein X is —C(═O)—O—.

### Claim 4 (depends on 1)

The block copolymer according to claim 1, wherein the linear hydrocarbon chain comprises 8 to 20 chain-forming atoms.

### Claim 5 (depends on 1)

The block copolymer according to claim 1, wherein the chain-forming atom is carbon, oxygen, nitrogen or sulfur.

### Claim 6 (depends on 1)

The block copolymer according to claim 1, wherein the chain-forming atom is carbon or oxygen.

### Claim 7 (depends on 1)

The block copolymer according to claim 1, wherein Y is represented by Formula 2 below:
—P-Q-Z [Formula 2]
wherein, P is an arylene group, Q is a single bond, an oxygen atom or —NR3—, where R3 is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or an aryl group, and Z is the linear hydrocarbon chain having 8 or more chain-forming atoms and substituted with a hydrocarbon functional group comprising one or more silicon atoms or iron atoms.

### Claim 8 (depends on 1)

The block copolymer according to claim 1, wherein the hydrocarbon functional group is a functional group represented by Formula 4 below or a silsesquioxanyl group:
wherein, each of R is independently a hydrogen atom or an alkyl group, L is a single bond or an oxygen atom, and n is a number in a range of 0 to 10.

### Claim 9 (depends on 1)

The block copolymer according to claim 1, wherein the polymer segment B comprises a unit of Formula 5 below
wherein, B is a monovalent substituent having an aromatic structure containing one or more halogen atoms.

### Claim 10 (depends on 1)

The block copolymer according to claim 1, wherein the polymer segment B comprises a unit of Formula 6 below:
wherein, X2 is a single bond, an oxygen atom, a sulfur atom, —S(═O)2—, an alkylene group, an alkenylene group, an alkynylene group, —C(═O)—X1— or —X1—C(═O)—, where X1 is a single bond, an oxygen atom, a sulfur atom, —S(═O)2—, an alkylene group, an alkenylene group or an alkynylene group, and W is an aryl group containing at least one halogen atom.

### Claim 11 (depends on 1)

The block copolymer according to claim 1, wherein the polymer segment B comprises a unit of Formula 7 below:
wherein, X2 is a single bond, an oxygen atom, a sulfur atom, —S(═O)2—, an alkylene group, an alkenylene group, an alkynylene group, —C(═O)—X1— or —X1—C(═O)—, where X1 is a single bond, an oxygen atom, a sulfur atom, —S(═O)2—, an alkylene group, an alkenylene group or an alkynylene group, and R1 to R5 are each independently hydrogen, an alkyl group, a haloalkyl group or a halogen atom, where the number of halogen atoms contained in R1 to R5 is 1 or more.

### Claim 12 (depends on 1)

A polymer film comprising the block copolymer of claim 1, wherein the block copolymer is self-assembled.

### Claim 13 (depends on 1)

A method for forming a polymer film, which comprises forming on a substrate a polymer film comprising the block copolymer of claim 1, wherein the block copolymer is self-assembled.

### Claim 14 (depends on 1)

A patterning method comprising a process of selectively removing, from a laminate having a substrate, and a polymer film formed on the substrate and comprising the block copolymer of claim 1, any one of the polymer segments in the block copolymer, wherein the block copolymer is self-assembled.

### Claim 15 (depends on 1)

The block copolymer according to claim 1, wherein the linear hydrocarbon chain is directly connected to the ring structure or is connected via a linker.

### Claim 16 (depends on 15)

The block copolymer according to claim 15, wherein the linker is an oxygen atom, a sulfur atom, —NR1—, —S(═O)2—, a carbonyl group, an alkylene group, an alkenylene group, an alkynylene group, —C(═O)—X1— or —X1—C(═O)—, where R1 is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or an aryl group and X1 is a single bond, an oxygen atom, a sulfur atom, —NR2—, —S(═O)2—, an alkylene group, an alkenylene group or an alkynylene group, and where R2 is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or an aryl group.

### Claim 17 (depends on 1)

The block copolymer according to claim 1, wherein the hydrocarbon functional group is a trialkylsiloxy group, a butyldimethylsilane group, a trimethylsilane group, a dimethylsilylmethyltrimethylsilane group, a trimethylsilyltrisilane group or a silsesquioxanyl group.

### Claim 18 (depends on 1)

The block copolymer according to claim 1, wherein the polymer segment A is present in a range of 10 mol % to 90 mol %.