Copolymer having adjustable glass transition temperature and having usefulness as organic electro-optic polymer, and organic electro-optic element using the same

Patent metadata

Field	Value
Publication number	US-10253124-B2
Application number	US-201515126080-A
Country	US
Kind code	B2
Filing date	Mar 17, 2015
Priority date	Mar 18, 2014
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

Abstract

An object of the present invention is to provide an organic EO polymer having a desired Tg. The present invention provides a copolymer comprising (i) a cycloalkane methacrylate and 2-isocyanatoethyl methacrylate as monomers at an adjusted blending ratio and (ii) an electro-optic molecule (EO molecule) bound to the copolymer, thereby exhibiting a desired glass transition temperature (Tg).

First claim

The invention claimed is:

1. A copolymer comprising:
(i) a cycloalkyl methacrylate having a fused ring and a 2-isocyanatoethyl methacrylate as monomers,
wherein the cycloalkyl methacrylate having a fused ring is at least one selected from the group consisting of dicyclopentanyl methacrylate, adamantyl methacrylate, and isobornyl methacrylate,
wherein a molar ratio of the cycloalkyl methacrylate to the 2-isocyanatoethyl methacrylate is 1.87:1 to 6:1, with the proviso that when the monomers are octahydro 1H-4,7-methano indenyl methacrylate (DCPMA) and 2-isocyanatoethyl methacrylate, a molar ratio of the DCPMA to the 2-isocyanatoethyl methacrylate of 3:2 is excluded; and
(ii) an electro-optic molecule (EO molecule) bound to the copolymer, wherein the EO molecule is a component having second order nonlinear optical properties, and wherein an amount of the EO molecule relative to a total amount of the copolymer with the EO molecule is 10 to 50% by weight,
wherein a glass transition temperature (Tg) of the copolymer is 120° C. to 230° C.

2. The copolymer according to claim 1 , wherein the cycloalkyl methacrylate has a bridged fused ring.

3. An organic electro-optic element comprising the copolymer according to claim 1 .

4. An organic electro-optic element comprising the copolymer according to claim 2 .

5. The organic electro-optic element according to claim 3 , which is an optical modulator or an optical switch.

6. The organic electro-optic element according to claim 4 , which is an optical modulator or an optical switch.

7. A method for producing a copolymer having a glass transition temperature (Tg) of 120° C. to 230° C., the method comprising:
(i) preparing a copolymer comprising a cycloalkyl methacrylate having a fused ring and a 2-isocyanatoethyl methacrylate as monomers,
wherein the cycloalkyl methacrylate having a fused ring is at least one selected from the group consisting of dicyclopentanyl methacrylate, adamantyl methacrylate, and isobornyl methacrylate, and
wherein a molar ratio of the cycloalkyl methacrylate to the 2-isocyanatoethyl methacrylate is 1.87:1 to 6:1, with the proviso that when the monomers are octahydro 1H-4,7-methano indenyl methacrylate (DCPMA) and 2-isocyanatoethyl methacrylate, a molar ratio of the DCPMA to the 2-isocyanatoethyl methacrylate of 3:2 is excluded; and
(ii) binding an electro-optic molecule (EO molecule) to the copolymer, wherein the EO molecule is a component having second order nonlinear optical properties, and wherein an amount of the EO molecule relative to a total amount of the copolymer with the EO molecule is 10 to 50% by weight.

Assignees

• Nat Inst Inf & Comm Tech

Inventors

• Otomo Akira
• Aoki Isao
• Yamada Toshiki
• Miki Hideki

Classifications

• C08G18/288

  Compounds containing at least one heteroatom other than oxygen or nitrogen · CPC title

• C08G18/728

  Polymerisation products of compounds having carbon-to-carbon unsaturated bonds and having isocyanate or isothiocyanate groups or groups forming isocyanate or isothiocyanate groups · CPC title

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G18/2815

  Monohydroxy compounds · CPC title

• G02F1/3617

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