# US 11,079,678 B2 · Photopolymer composition

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- Number: US 11,079,678 B2
- Document ID: US11079678B2
- Status: Granted
- Kind: B2
- Application number: 16/343,153
- Filed: 2018-09-11
- Published: 2019-10-17
- Granted: 2021-08-03
- Earliest claimed: 2017-09-27
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Seok Hoon Jang; Heon Kim; Yongjoon Heo; Se Hyun Kwon; Yeong Rae Chang
- Web page: https://patentgrep.com/patent/US11079678B2

## CPC

- G03F 7/0758: {with silicon- containing groups in the side chains}
- C08F 2/50: with sensitising agents
- C08K 5/541: containing oxygen
- C08L 33/06: of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L 43/04: Homopolymers or copolymers of monomers containing silicon
- G03F 7/001: {Phase modulating patterns, e.g. refractive index patterns}
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/033: the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
- G03H 1/02: Details {of features involved during the holographic process; Replication of holograms without interference recording}
- G03H 2001/0216: {Optical components (G03H2001/0224, G03H1/0256 take precedence; corresponding details, see subgroups of G03H2223/00)}
- G03H 2001/0264: {Organic recording material}
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G03H: HOLOGRAPHIC PROCESSES OR APPARATUS (holograms, e.g. point holograms, used as ordinary optical elements G02B5/32; producing stereoscopic or other three-dimensional effects G02B30/00; diffraction-grating systems G02B27/44; systems using moiré fringes G02B27/60; optical logic elements G02F3/00; stereo-photography G03B35/00; photosensitive materials or processes for photographic purposes G03C; {stereo-photographic or similar processes G03C9/00}; apparatus for processing exposed photographic materials G03D; analogue computers performing mathematical operations with the aid of optical elements G06E3/00; authentication by radiation, of concealed information carried by holograms or diffraction gratings G06K19/16; holographic storage G11B7/0065, G11C13/04; {stereoscopic or other three dimensional effects in television systems H04N13/00})

## Abstract

A photopolymer composition comprising a polymer matrix or a precursor thereof including a reaction product between (i) a (meth)acrylate-based (co)polymer in which a silane-based functional group is located in a branched chain and an equivalent weight of the silane-based functional group is 300 g/eq to 2000 g/eq, and (ii) a linear silane crosslinking agent; a photoreactive monomer; and a photoinitiator, a hologram recording medium using the same, an optical element using the hologram recording medium, and a holographic recording method. The photopolymer composition can more easily provide a photopolymer layer having improved durability against temperature and humidity while having a large refractive index modulation value.

## Claims

### Claim 1

A photopolymer composition comprising:
a polymer matrix or a precursor thereof including a reaction product between (i) a (meth)acrylate-based (co)polymer in which a silane-based functional group is located in a branched chain and an equivalent weight of the silane-based functional group is 300 g/eq to 2000 g/eq, and (ii) a linear silane crosslinking agent;
a photoreactive monomer; and
a photoinitiator;
wherein the linear silane crosslinking agent includes a linear polyether main chain having a weight average molecular weight of 100 g/mol to 2000 g/mol and a silane-based functional group bonded to a terminal or branched chain of the linear polyether main chain.

### Claim 2 (depends on 1)

The photopolymer composition of claim 1, wherein the linear silane crosslinking agent is contained in an amount of 10 parts by weight to 90 parts by weight, based on 100 parts by weight of the (meth)acrylate-based (co)copolymer.

### Claim 3 (depends on 1)

The photopolymer composition of claim 1, wherein a modulus (storage modulus) of the reaction product is 0.01 MPa to 5 MPa as measured at a frequency of 1 Hz at room temperature using DHR equipment (TA Instruments).

### Claim 4 (depends on 1)

The photopolymer composition of claim 1, wherein the silane-based functional group and the linear polyether main chain are bonded via a urethane bond.

### Claim 5 (depends on 1)

The photopolymer composition of claim 1, wherein an equivalent weight of the silane-based functional group contained in the linear silane crosslinking agent is 200 g/eq to 1000 g/eq.

### Claim 6 (depends on 1)

The photopolymer composition of claim 1, wherein a ratio between the equivalent weight of the silane-based functional group located in the branched chain of the (meth)acrylate-based (co)polymer and the equivalent weight of the silane-based functional groups contained in the linear silane crosslinking agent is from 22:1 to 0.5:1.

### Claim 7 (depends on 1)

The photopolymer composition of claim 1, wherein the photoreactive monomer comprises a polyfunctional (meth)acrylate monomer or a monofunctional (meth)acrylate monomer.

### Claim 8 (depends on 1)

The photopolymer composition of claim 1, wherein the photoreactive monomer has a refractive index of 1.5 or more.

### Claim 9 (depends on 1)

The photopolymer composition of claim 1, wherein the photopolymer composition comprises: 20% to 80% by weight of the polymer matrix or a precursor thereof; 10% to 70% by weight of the photoreactive monomer; and 0.1% to 15% by weight of the photoinitiator based on the total weight of the photopolymer composition.

### Claim 10 (depends on 1)

The photopolymer composition of claim 1, wherein the photopolymer composition further comprises a fluorine-based compound.

### Claim 11 (depends on 10)

The photopolymer composition of claim 10, wherein the fluorine-based compound includes at least two difluoromethylene groups, and at least one functional group selected from the group of an ether group, an ester group, and an amide group.

### Claim 12 (depends on 10)

The photopolymer composition of claim 10, wherein the fluorine-based compound has a refractive index of less than 1.45.

### Claim 13 (depends on 10)

The photopolymer composition of claim 10, wherein the fluorine-based compound is contained in an amount of 30 parts by weight to 150 parts by weight, based on 100 parts by weight of the photoreactive monomer.

### Claim 14 (depends on 1)

The photopolymer composition of claim 1, wherein the polymer matrix has a refractive index of 1.46 to 1.53.

### Claim 15 (depends on 1)

The photopolymer composition of claim 1, wherein the photopolymer composition further comprises a photosensitizing dye, or other additives.

### Claim 16 (depends on 1)

A hologram recording medium produced by curing the photopolymer composition of claim 1.

### Claim 17 (depends on 16)

An optical element comprising the hologram recording medium of claim 16.

### Claim 18 (depends on 1)

A holographic recording method comprising selectively polymerizing photoreactive monomers contained in the photopolymer composition of claim 1 by a coherent laser.