Electro-optic polymer

Patent metadata

Field	Value
Publication number	US-11236188-B2
Application number	US-201716314086-A
Country	US
Kind code	B2
Filing date	Jun 28, 2017
Priority date	Jun 29, 2016
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

An object of the present invention is to provide a novel electro-optic polymer. Another object of the present invention is to provide a novel electro-optic polymer with a low alicyclic methacrylate monomer content. The polymer according to the present invention is a polymer comprising (a) a base polymer having a reactive group (A), (b) an electro-optic molecule having a plurality of reactive groups (B), and a bond (C) formed by reaction of the reactive group (A) with the plurality of reactive groups (B), the bond (C) being at least one type of bond selected from the group consisting of a (thio)ester bond, a (thio)urethane bond, a (thio)urea bond and a (thio)amide bond.

First claim

The invention claimed is:

1. A polymer comprising (a) a base polymer having a reactive group (A), (b) an electro-optic molecule having a plurality of reactive groups (B), and a bond (C) formed by reaction of the reactive group (A) with the plurality of reactive groups (B), wherein the bond (C) is at least one type of bond selected from the group consisting of a (thio)ester bond, a (thio)urethane bond, a (thio)urea bond and a (thio)amide bond,
wherein the (a) base polymer is a methacrylate-based base polymer,
wherein the (b) electro-optic molecule comprises a compound represented by the following formula (1):

wherein:
R D 1a , R D 2a and R D 3a independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a silyloxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, —R 1 —OH (wherein R 1 is a hydrocarbon group), —OR 2 —OH (wherein R 2 is a hydrocarbon group), —OC(═O)R 3 (wherein R 3 is a hydrocarbon group), an amino group, —R 4 —NH 2 (wherein R 4 is a hydrocarbon group), a thiol group, —R 5 —SH (wherein R 5 is a hydrocarbon group), —NCO or —R 6 —NCO (wherein R 6 is a hydrocarbon group);
R D 4a and R D 5a independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an acyloxyalkyl group, a silyloxyalkyl group, —R 1 —OH (wherein R 1 is a hydrocarbon group), —R 4 —NH 2 (wherein R 4 is a hydrocarbon group), an aryl group, —R 5 —SH (wherein R 5 is a hydrocarbon group) or —R 6 —NCO (wherein R 6 is a hydrocarbon group);
X represents a linking group; and
R A 1a and R A 2a independently represent a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a haloalkyl group, an aryl group, a hydroxy group, —R 1 —OH (wherein R 1 is a hydrocarbon group), —OR 2 —OH (wherein R 2 is a hydrocarbon group), an amino group, —R 4 —NH 2 (wherein R 4 is a hydrocarbon group), a thiol group, —R 5 —SH (wherein R 5 is a hydrocarbon group), —NCO or —R 6 —NCO (wherein R 6 is a hydrocarbon group),
with the proviso that the compound has two or more reactive groups (B) selected from the group consisting of hydroxy, —R 1 —OH, —OR 2 —OH, amino, —R 4 —NH 2 , thiol, —R 5 —SH, —NCO and —R 6 —NCO contained in the formula (1), and
wherein the polymer satisfies any one of the following (I) and (II):
(I) R D 1a is the reactive group (B) and at least one of R D 4a , R D 5a , R A 1a and R A 2a is the reactive group (B); and
(II) R D 4a and R D 5a are the reactive groups (B).

2. The polymer according to claim 1 , wherein the reactive group (A) or the reactive groups (B) are at least one type of group selected from the group consisting of an iso(thio)cyanato group, a hydroxy group, a thiol group, an amino group, a carboxyl group and an acid anhydride group.

3. The polymer according to claim 1 , wherein the reactive group (A) or the reactive groups (B) comprise an iso(thio)cyanato group.

4. The polymer according to claim 1 , wherein the (a) base polymer is a methacrylate-based base polymer having an iso(thio)cyanato group.

5. The polymer according to claim 4 , wherein the methacrylate-based base polymer comprises a structural unit derived from (a1) an iso(thio)cyanato group-containing (meth)acrylate.

6. The polymer according to claim 4 , wherein the methacrylate-based base polymer comprises a structural unit derived from (a2) an iso(thio)cyanato group-free methacrylate containing an alicyclic methacrylate.

7. The polymer according to claim 5 , wherein the methacrylate-based base polymer further comprises a structural unit derived from (a2) an iso(thio)cyanato group-free methacrylate containing an alicyclic methacrylate.

8. The polymer according to claim 7 , wherein the methacrylate-based base polymer comprises the structural unit derived from (a2) an iso(thio)cyanato group-free methacrylate and the structural unit derived from (a1) an iso(thio)cyanato group-containing (meth)acrylate at a molar ratio of 0.1:1 to 19:1.

9. The polymer according to claim 7 , wherein the methacrylate-based base polymer comprises a structural unit derived from an alicyclic methacrylate and the structural unit derived from (a1) an iso(thio)cyanato group-containing (meth)acrylate at a molar ratio of 0.01:1 to 19:1.

10. The polymer according to claim 8 , wherein the methacrylate-based base polymer comprises a structural unit derived from an alicyclic methacrylate and the structural unit derived from (a1) an iso(thio)cyanato group-containing (meth)acrylate at a molar ratio of 0.01:1 to 19:1.

11. The polymer according to claim 1 , wherein the (b) electro-optic molecule is a compound having a structure represented by D (a donor structure)-B (a bridge structure)-A (an acceptor structure).

12. The polymer according to claim 1 , wherein the reactive group (A) is an iso(thio)cyanato group, and the reactive groups (B) are at least one type of group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group and an acid anhydride group.

13. The polymer according to claim 1 , which satisfies any one of the following (A) and (B):
(A) R D 1a is a hydroxyalkoxy group, and at least one of R D 4a , R D 5a , R A 1a and R A 2a is a hydroxyalkyl group, a hydroxyaryl group or a hydroxyaralkyl group; and
(B) R D 4a and R D 5a are each a hydroxyalkyl group, a hydroxyaryl group or a hydroxyaralkyl group.

14. The polymer according to claim 1 , wherein the (a) base polymer and the (b) electro-optic molecule are contained at a weight ratio of 30:70 to 90:10.

15. An optical element comprising the polymer according to claim 1 .

Assignees

• Nat Inst Inf & Comm Tech

Inventors

• Otomo Akira
• Aoki Isao
• Yamada Toshiki

Classifications

• G02F1/061

  based on electro-optical organic material (G02F1/07, {G02F1/13} take precedence) · CPC title

• C08F20/10

  Esters · CPC title

• C08F220/36 Primary

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08F265/04 Primary

  on to polymers of esters · CPC title

• G02F1/3617

  having the non-linear optical group in a side chain · CPC title