Nonlinear optical chromophores having a diamondoid group attached thereto, methods of preparing the same, and uses thereof

Patent metadata

Field	Value
Publication number	US-12228840-B2
Application number	US-202318378217-A
Country	US
Kind code	B2
Filing date	Oct 10, 2023
Priority date	Jun 25, 2020
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

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-optical film 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°):

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.

2. An electro-optical film 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°):

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.

3. An electro-optical film 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 Y represents a phenylsulfanyl; 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.

4. The electro-optical film according to claim 3 , 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.

5. The electro-optical film according to claim 3 , wherein the diamondoid is an adamantyl 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