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Title:
NONLINEAR OPTICAL CHROMOPHORES HAVING TETRAHYDROCARBAZOLE DONOR GROUPS, LYOTROPIC COMPOSITIONS CONTAINING THE SAME, AND METHODS OF POLING SUCH COMPOSITIONS
Document Type and Number:
WIPO Patent Application WO/2023/107680
Kind Code:
A4
Abstract:
Nonlinear optical chromophore compositions which display lyotropic nematic liquid crystal phases in polar organic solvents and provide a mechanical anisotropic effect allowing for the formation of a non-centrosymmetric chromophore-polymer matrix without the application of an electric field.

Inventors:
PECINOVSKY CORY (US)
JOHNSON BARRY (US)
RAMANN GINELLE A (US)
Application Number:
PCT/US2022/052367
Publication Date:
August 10, 2023
Filing Date:
December 09, 2022
Export Citation:
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Assignee:
LIGHTWAVE LOGIC INC (US)
International Classes:
G02F1/361
Attorney, Agent or Firm:
BONELLA, Michael J. (US)
Download PDF:
Claims:
AMENDED CLAIMS received by the International Bureau on 20 June 023 (20.06.2023)

1. A lyotropic composition comprising the nonlinear optical chromophore of the general formula (I):

D-77-A 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 77 represents a 77-bridge between A and D; wherein the electron -donating group D comprises a tetrahydrocarbazole moiety bound to the 77-bridge at a carbon atom in the tetrahydro six-membered carbon ring of the tetrahydrocarbazole moiety, and wherein the hydrogen bound to the nitrogen of the five-membered ring of the carbazole moiety is replaced with a substituent R.

2. The nonlinear optical chromophore according to claim 1, wherein the tetrahydrocarbazole moiety is represented by the general formula (II): wherein R represents a moiety other than hydrogen.

3. The nonlinear optical chromophore according to claim 2, wherein R represents a moiety comprising an aromatic ring.

4. The nonlinear optical chromophore according to claim 3, wherein R represents a moiety comprising an aromatic ring bearing a triarylsubstituted silyl substituent.

1

AMENDED SHEET (ARTICLE 19)

5. The nonlinear optical chromophore according to claim 4, wherein R represents a moiety of the general formula (III)

6. The nonlinear optical chromophore according to claim 1, wherein A represents an electron-accepting group of the general formula (Ia): wherein R2 and R3 each independently represents a moiety selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted

C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH2)n-O-(CH2)n where n is 1-10.

7. The nonlinear optical chromophore according to claim 1, having the general formula (IV)

2

AMENDED SHEET (ARTICLE 19)

wherein R represents a substituent other than hydrogen; wherein R2 and R3 each independently represents a moiety selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkyl-aryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH2)n-0- (CH2)n where n is 1-10; wherein each Y independently represents: a hydrogen, a halogen, an alkyl group, aryl group, sulfur or oxygen linked alkyl or aryl group, or a branched or unbranched, optionally heteroatom -containing C1-C4 substituent; wherein each a and b independently represents an integer of 0 to 3; z represents an integer of 1 to 3; and wherein each arc A independently represents a substituted or unsubstituted C2-C4 alkyl group, which together with the carbon bearing the Y substituent and its two adjacent carbon atoms forms a cyclic group.

8. The lyotropic composition of claim 1, further comprising one or more aprotic, polar solvents.

9. The lyotropic composition according to claim 8, wherein the one or more aprotic, polar solvents comprise propylene carbonate.

10. A thin fdm prepared from the composition according to claim

8.

AMENDED SHEET (ARTICLE 19)

11. The thin fdm of claim 10, wherein the fdm is prepared by removal of the one or more solvents from the composition while the nonlinear optical chromophore is in a highly ordered and densely packed state.

12. An electro-optic device comprising the thin fdm according to claim 11.

4

AMENDED SHEET (ARTICLE 19)