Nonlinear Optical Chromophores Having a Diamondoid Group Attached Thereto, Methods of Preparing the Same, and Uses Thereof

Patent metadata

Field	Value
Publication number	US-2025155775-A1
Application number	US-202519020836-A
Country	US
Kind code	A1
Filing date	Jan 14, 2025
Priority date	Jun 25, 2020
Publication date	May 15, 2025
Grant date	—

Abstract

Nonlinear optical chromophores having one or more diamondoid groups covalently attached to the chromophore, methods of making nonlinear optical chromophores, their use in thin films and electro-optical devices containing such nonlinear optical chromophores and thin films comprising the same.

First claim

What is claimed is:

1 . An electro-optic device comprising one or more electro-optical film, wherein the one or more electro-optical film each comprising a nonlinear optical chromophore dispersed and poled within a host polymer matrix, wherein the nonlinear optical chromophore of the general formula (I):
D-Π-A   (I)

wherein D represents an organic electron-donating group; A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and Π represents a Π-bridge between the organic electron-accepting group and the organic electron-donating group; wherein the Π-bridge has the following formula (Π d ):

wherein each Y independently represents sulfur or oxygen linked alkyl or aryl group;
wherein each a and b independently represents an integer of 0 to 3; and z represents an integer of 1 to 3;
the nonlinear optical chromophore comprising a diamondoid covalently bound to the organic electron-donating group.

2 .- 7 . (canceled)

8 . The electro-optic device according to claim 1 , wherein the organic electron-accepting group has the general formula (I a ):

wherein R 2 and R 3 each independently represents a moiety selected from the group consisting of H, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH 2 ) n —O—(CH 2 ) n where n is 1-10.

9 . The electro-optic device according to claim 1 , wherein the diamondoid is an adamantyl group.

10 . The electro-optic device according to claim 1 , wherein Y represents a phenylsulfanyl group.

11 . An electro-optic device comprising one or more electro-optical film, wherein the one or more electro-optical film each comprising a nonlinear optical chromophore dispersed and poled within a host polymer matrix, wherein the nonlinear optical chromophore of the general formula (I):
D-Π-A   (I)

wherein D represents an organic electron-donating group; A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and Π represents a Π-bridge between the organic electron-accepting group and the organic electron-donating group; wherein the Π-bridge between the organic electron-accepting group and the organic electron-donating group has the following formula (Π d ):

wherein each Y independently represents a sulfur linked aryl group of the following formula (Π 1 ):

wherein each a and b independently represents an integer of 0 to 3; and z represents an integer of 1 to 3;
the nonlinear optical chromophore comprising one or more diamondoids, wherein each of the one or more diamondoids is covalently bound to one of the organic electron-accepting group, or the organic electron-donating group.

12 . An electro-optic device comprising one or more electro-optical film, wherein the one or more electro-optical film each comprising a nonlinear optical chromophore dispersed and poled within a host polymer matrix, wherein the nonlinear optical chromophore of the general formula (I):
D-Π-A   (I)

wherein D represents an organic electron-donating group; A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and Π represents a Π-bridge between the organic electron-accepting group and the organic electron-donating group; wherein the Π-bridge between the organic electron-accepting group and the organic electron-donating group has the following formula (Π d ):

wherein each Y independently represents a sulfur linked aryl group of the following formula (Π 2 ):

wherein each a and b independently represents an integer of 0 to 3; and z represents an integer of 1 to 3;
the nonlinear optical chromophore comprising one or more diamondoids, wherein each of the one or more diamondoids is covalently bound to one of the organic electron-accepting group, or the organic electron-donating group.

Assignees

• Lightwave Logic Inc

Inventors

• Pecinovsky Cory
• Johnson Barry
• Ramann Ginelle

Classifications

• G02F1/3612

  Heterocycles having N as heteroatom · CPC title

• G02F1/0018

  Electro-optical materials · CPC title

• C07D487/00

  Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 · CPC title

• C09B23/086

  more than five >CH- groups · CPC title

• C09B23/0075

  the polymethine chain being part of an heterocyclic ring · CPC title