Stilbazolium derivative and nonlinear optical material using the same

Patent metadata

Field	Value
Publication number	US-9487484-B2
Application number	US-201514748050-A
Country	US
Kind code	B2
Filing date	Jun 23, 2015
Priority date	Jun 24, 2014
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

Provided is a stilbazolium derivative represented by the general formula (I):

wherein R 1 , R 2 , R 3 , and R 4 independently represent hydrogen, halogen, alkyl, hydroxyl, carboxyl, or amino; R 5 represents hydrogen or alkyl; X represents oxygen or NR 6 (R 6 is hydrogen or alkyl); and Y − represents an anion. In the general formula (I), some or all of hydrogens maybe deuterium.

First claim

What is claimed is:

1. A stilbazolium derivative of formula (I):

wherein R 1 , R 2 , R 3 , and R 4 independently represent hydrogen, halogen, unsubstituted or substituted alkyl, hydroxyl, carboxyl, or amino;
R 5 represents hydrogen or unsubstituted or substituted alkyl;
X represents oxygen or NR 6 (R 6 is hydrogen or unsubstituted or substituted alkyl);
Y − represents an anion selected from the group consisting of sulfonic acid anions, carboxylic acid anions, hydrogen sulfate ions, nitrate ions, tetrafluoroborate ions, perchlorate ions, perbromate ions, and periodate ions; and
in the general formula (I), some or all of hydrogens maybe deuterium wherein said substituted alkyl has a substituent selected from the group consisting of halogen, hydroxyl, ether, carboxyl, nitro, amino, and sulfone.

2. The stilbazolium derivative according to claim 1 , wherein R 1 and R 2 independently represent hydrogen or unsubstituted or substituted alkyl, R 3 and R 4 represent hydrogen, and R 5 represents methyl.

3. The stilbazolium derivative according to claim 1 , wherein Y − is a sulfonic acid anion.

4. The stilbazolium derivative according to claim 2 , wherein Y − is a sulfonic acid anion.

5. A stilbazolium derivative of formula (III):

6. A nonlinear optical material comprising the stilbazolium derivative according to claim 1 .

7. A nonlinear optical material comprising the stilbazolium derivative according to claim 2 .

8. A nonlinear optical material comprising the stilbazolium derivative according to claim 5 .

9. A light source device comprising the nonlinear optical material according to claim 6 as a light wavelength conversion element.

10. A light source device comprising the nonlinear optical material according to claim 7 as a light wavelength conversion element.

11. A light source device comprising the nonlinear optical material according to claim 8 as a light wavelength conversion element.

12. A terahertz generation device comprising the nonlinear optical material according to claim 6 .

13. A terahertz generation device comprising the nonlinear optical material according to claim 7 .

14. A terahertz generation device comprising the nonlinear optical material according to claim 8 .

15. A stilbazolium derivative of formula (I):

wherein R 1 , R 2 , R 3 , and R 4 independently represent hydrogen, halogen, unsubstituted or substituted alkyl, hydroxyl, carboxyl, or amino;
R 5 represents hydrogen or unsubstituted or substituted alkyl;
X represents oxygen or NR 6 (R 6 is hydrogen or unsubstituted alkyl);
Y − represents an anion; and
in the general formula (I), some or all of hydrogens maybe deuterium, wherein said substituted alkyl has a substituent selected from the group consisting of halogen, hydroxyl, ether, carboxyl, ester, nitro, amino, and sulfone, and

wherein R 1 and R 2 are alkyl when X is oxygen.

16. The stilbazolium derivative according to claim 15 , wherein Y − is a sulfonic acid anion.

17. The stilbazolium derivative according to claim 15 , wherein R 1 and R 2 independently represent hydrogen or unsubstituted or substituted alkyl, R 3 and R 4 represent hydrogen, R 5 represents methyl.

18. A nonlinear optical material comprising the stilbazolium derivative according to claim 15 .

19. A light source device comprising the nonlinear optical material according to claim 15 as a light wavelength conversion element.

20. A terahertz generation device comprising the nonlinear optical material according to claim 15 .

Assignees

• Arkray Inc
• Nat Univ Corp Yamagata Univ

Inventors

• Aoki Kazuyoshi
• Okada Shuji

Classifications

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• G02F1/3551

  Crystals · CPC title

• G02F2203/13

  involving THZ radiation · CPC title

• G02F1/13

  based on liquid crystals, e.g. single liquid crystal display cells · CPC title

• G02F1/37

  for second-harmonic generation {(G02F1/3532 takes precedence)} · CPC title