Photopolymer composition

Patent metadata

Field	Value
Publication number	US-11435664-B2
Application number	US-201916968084-A
Country	US
Kind code	B2
Filing date	Dec 13, 2019
Priority date	Dec 14, 2018
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

Provided is a photopolymer composition for hologram recording comprising:
a polymer matrix or a precursor thereof; a dye including a compound of the following Chemical Formula 1; a photoreactive monomer; and a photoinitiator,

First claim

The invention claimed is:

1. A photopolymer composition for hologram recording comprising:
a polymer matrix or a precursor thereof;
a dye including a compound of the following Chemical Formula 1;
a photoreactive monomer; and
a photoinitiator,

wherein in Chemical Formula 1:
X is oxygen or sulfur; and
R 2 and R 3 are each independently an alkoxy group having 1 to 5 carbon atoms; and R 1 and R 4 are each independently selected from the group consisting of: an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen; a cycloalkyl group having 4 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing one or more of oxygen, sulfur or nitrogen; and an aromatic hydrocarbon group having 6 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing one or more of oxygen, sulfur or nitrogen; or
R 2 and R 3 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a halogen; and one of R 1 and R 4 is an amine group and the other is selected from the group consisting of: an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen; a cycloalkyl group having 4 to 20 carbon atoms; and an aromatic hydrocarbon group having 6 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen.

2. The photopolymer composition according to claim 1 , wherein the polymer matrix or a precursor thereof includes:
1) a reaction product between a compound containing one or more isocyanate groups and a polyol; or
2) a polymer matrix including a silane crosslinking agent and a (meth)acrylate-based (co)polymer in which a silane-based functional group is located in a branched chain.

3. The photopolymer composition according to claim 2 , wherein the silane crosslinking agent includes:
a linear polyether main chain having a weight average molecular weight of 100 to 2000; and
a silane-based functional group bonded at a terminal end or a branched chain of the main chain.

4. The photopolymer composition according to claim 2 , wherein:
the (meth)acrylate-based (co)polymer includes a (meth)acrylate repeating unit and a (meth)acrylate repeating unit in which a silane-based functional group is located in the branched chain; and
the (meth)acrylate-based (co)polymer has a weight average molecular weight of 100,000 to 1,000,000.

5. The photopolymer composition according to claim 1 ,
wherein the photoreactive monomer includes a polyfunctional (meth)acrylate monomer or a monofunctional (meth)acrylate monomer.

6. The photopolymer composition according to claim 1 , comprising:
1% to 80% by weight of the polymer matrix or a precursor thereof;
1% to 80% by weight of the photoreactive monomer;
0.0001% to 10% by weight of the dye; and
0.1% to 20% by weight of the photoinitiator.

7. The photopolymer composition according to claim 1 , wherein the photopolymer composition further comprises at least one additive selected from the group consisting of a catalyst, a phosphate-based compound, and a low refractive index fluorine-based compound.

8. The photopolymer composition according to claim 7 , wherein the low refractive index fluorine-based compound includes at least two difluoromethylene groups and at least one functional group selected from the group consisting of an ether group, an ester group and an amide group.

9. A hologram recording medium, comprising the photopolymer composition of claim 1 .

10. An optical element comprising:
a recorded holographic media of the hologram recording medium of claim 9 ,
wherein the recorded holographic media includes a holographic pattern corresponding to the optical element.

11. A holographic recording method comprising selectively polymerizing photoreactive monomers contained in the photopolymer composition of claim 1 by interference of two interference lights.

12. A hologram recording medium, comprising:
a polymer matrix or a precursor thereof;
a dye including a compound of the following Chemical Formula 1; and
a photoreactive monomer,
wherein the hologram recording medium has a refractive index modulation value (n) of 0.023 or more in a thickness range of 5 μm to 30 μm:

wherein in Chemical Formula 1:
X is oxygen or sulfur; and
R 2 and R 3 are each independently an alkoxy group having 1 to 5 carbon atoms; and R 1 and R 4 are each independently selected from the group consisting of: an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen; a cycloalkyl group having 4 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing one or more of oxygen, sulfur or nitrogen; and an aromatic hydrocarbon group having 6 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing one or more of oxygen, sulfur or nitrogen; or

R 2 and R 3 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or a halogen; and one of R 1 and R 4 is an amine group and the other is selected from the group consisting of: an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen; a cycloalkyl group having 4 to 20 carbon atoms; and an aromatic hydrocarbon group having 6 to 20 carbon atoms substituted with an alicyclic or aromatic heterocycle having 4 to 20 carbon atoms containing at least one of oxygen, sulfur or nitrogen.

13. The hologram recording medium according to claim 12 , wherein the coating layer further includes a low refractive index fluorine-based compound comprising at least two difluoromethylene groups and at least one functional group selected from the group consisting of an ether group, an ester group and an amide group.

14. An optical element comprising:
a recorded holographic media of the hologram recording medium of claim 12 ,
wherein the recorded holographic media includes a holographic pattern corresponding to the optical element.

Assignees

• Lg Chemical Ltd
• Korea Advanced Inst Sci & Tech

Inventors

• Kim Heon
• Kim Yoosik
• Kharbash Raisa
• Kwon Se Hyun
• Chang Yeongrae
• Jang Seokhoon

Classifications

• G03F7/031

  Organic compounds not covered by group G03F7/029 · CPC title

• G03F7/70408

  Interferometric lithography; Holographic lithography; Self-imaging lithography, e.g. utilizing the Talbot effect · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• G03F7/033

  the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers · CPC title

• G03F7/0758

  with silicon- containing groups in the side chains · CPC title