Chromophores for photochromic compositions useful for three dimensional display applications

Patent metadata

Field	Value
Publication number	US-10752780-B2
Application number	US-201816004152-A
Country	US
Kind code	B2
Filing date	Jun 8, 2018
Priority date	Apr 23, 2014
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

Described herein are novel azo-benzene type chromophores. The chromophores are useful in photochromic compositions comprising a polymer matrix and a chromophore, wherein the chromophore is a novel azo-benzene type structure. The photochromic composition is photoresponsive upon irradiation by at least one wavelength of laser light across the visible light spectrum. Photochromic devices which comprise the novel azo-benzene type chromophore compound show significantly higher photoinduced birefringence, higher diffraction efficiency, and brighter images than devices that comprise well known azo-benzene chromophores. The photochromic composition may include a liquid crystal.

First claim

What is claimed is:

1. A chromophore represented by for Lila (Ill):

wherein Pen is

wherein;
A 1 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted heteroalkyl, or optionally substituted carbonyl;
X 1 is CR 1 or N, X 2 is CR 2 or N, X 3 is CR 3 or N, X 4 is CR 4 or N;
R 1 -R 4 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted heteroalkyl, optionally substituted amido, optionally substituted alkoxy, optionally substituted carbonyl, and optionally substituted carboxy, optionally substituted aryloxy, optionally substituted acyloxy, optionally substituted ketone, optionally substituted ester, optionally substituted ether, —F, —ON, —CF 3 , —NO 2 , or —Br;
R 5 is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted heteroalkyl, optionally substituted carbonyl, optionally substituted ketone, —F, —ON, —CF 3 , —NO 2 , or —Br,
wherein Z is N or O.

2. The chromophore of claim 1 , wherein R 1 -R 4 are independently hydrogen or alkyl.

3. The chromophore of claim 1 , wherein at least one of X 1 -X 3 is N.

4. The chromophore of claim 1 , wherein the chromophore is A or B or C:

5. The chromophore of claim 1 , wherein A 1 is —H 2 C—CH 2 —CH 2 —CH 2 —CH 2 —CH 3 , —CH 2 —CH 2 —CH 2 —CH 3 ,

6. A photochromic composition comprising an optically transparent polymer matrix and the chromophore of claim 1 .

7. The photochromic composition of claim 6 , wherein the composition is configured to be photoresponsive upon irradiation by first laser having a first wavelength in the visible light spectrum, and wherein the first laser is selected from the group consisting of a blue laser, a green laser, and a red laser.

8. The photochromic composition of claim 6 , wherein two or more chromophores are mixed within the composition.

9. The photochromic composition of claim 6 , wherein the chromophore is present in the composition in an amount in the range of about 0.01 wt % to about 30 wt %.

10. The photochromic composition of claim 6 , wherein the chromophore is present in the composition in an amount in the range of about 1 wt % to about 15 wt %.

11. The photochromic composition of claim 6 , wherein the polymer matrix comprises a repeating unit that includes a moiety represented by the following formula (IV):

wherein Rb 1 , and Rb 2 are independently hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkenyl, or C 6 -C 10 aryl.

12. The photochromic composition of claim 6 , wherein the polymer matrix is formed from polyethylene terephthalate, polyacrylate, polymethacrylate, polyvinyl carbazole, polymethyl methacrylate, polyvinyl butyral, ethylene vinyl acetate, ethylene tetrafluoroethylene, polyimide, amorphous polycarbonate, polystyrene, siloxane sol-gel, polyurethane, or any combination thereof.

13. The photochromic composition of claim 6 , wherein the chromophore may be doped into the polymer matrix such that the polymer and the chromophore are not chemically bonded.

14. The photochromic composition of claim 6 , wherein one or more of the chromophore compounds is covalently bonded to the polymer matrix.

15. The photochromic composition of claim 6 , wherein the composition is configured to be photoresponsive upon irradiation by a first laser having a first wavelength in the visible light spectrum and a second laser having a second wavelength in the visible light spectrum, wherein the first wavelength is different from the second wavelength and wherein the first and second lasers are selected from the group consisting of a blue laser, a green laser, and a red laser.

16. The photochromic composition of claim 15 , wherein the composition is photoresponsive upon irradiation with a third laser having a third wavelength in the visible light spectrum, such that the third laser has a wavelength that is different from that of the first laser and the second laser, wherein the third laser is selected from the group consisting of a blue laser, a green laser, and a red laser.

17. The photochromic composition of claim 16 , wherein the blue laser has a wavelength of about 488 nm or about 457 nm, the green laser has a wavelength of about 532 nm, and the red laser has a wavelength of about 633 nm.

18. An optical device that comprises the photochromic composition according to claim 6 .

Assignees

• Nitto Denko Corp

Inventors

• Gu Tao
• Rachwal Bogumila
• Siddiqui Ozair
• Rachwal Stanislaw
• Kitahara Isamu
• Simavoryan Sergey
• Wang Peng
• Yamamoto Michiharu

Classifications

• C09K19/601 Primary

  Azoic · CPC title

• C08L33/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09B62/0086

  with coupling component containing a reactive methylene group · CPC title

• C09B29/0011

  from diazotized anilines directly substituted by a heterocyclic ring (not condensed) · CPC title

• C09B29/0807

  characterised by the amino group · CPC title