US4348298A
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Nematic liquid crystal mixtures
Assignee: Werk fuer Fernsehelektronik im VEB Kombinat Mikroelektronik VEB
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Filing: 1980-03-31
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Granted: 1982-09-07
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Expires: 2000-03-31
Abstract
Abstract A nematic liquid crystal mixture for modulation of the transmitted or incident light and for rendition of colored numerals, symbols and images in electro-optical devices, the said mixture comprising (a) a nematic liquid crystal adapted for reorientation in an electrical field due to its dielectric anisotropy and (b) a dichroic dyestuff adapted for simultaneous orientation changes together with the said nematic liquid crystal between a light absorption and a light transmission position based on the guest-host effect, the said dyestuff being an s-tetrazine derivative having an elongate molecular structure and having the formula ##STR1## wherein X is ##STR2## R 1 and Y is R 2 -- or ##STR3## R 1 being H--, F--, Cl--, Br--, J--, O 2 N--, NC--, HO--, H 2 N--, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1" --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC--, C n H 2n+1 CO-- or C n H 2n+1 OCOO--, and R 2 being H--, F--, Cl--, Br--, J--, O 2 N--, NC--, HO--, H 2 N--, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1 --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC--, C n H 2n+1 CO-- or C n H 2n+1 OCOO--, and R 3 being H--, F--, Cl--, Br--, J--, CH 3 -- or CF 3 --, and R 4 being H--, F--, Cl--, Br--, J--, CH 3 --, or CF 3 --, n is a positive integer.
Inventors
- 👤 Horst Zaschke
- 👤 Rudolf Wolff
- 👤 Gerhard Pelzl
- 👤 Dietrich Demus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:17
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/52; C09K19/60
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
272 words
A nematic liquid crystal composition for modulation of transmitted or incident light, and for rendition of numerals, symbols, and images in color in electro-optical devices, comprising (A) a nematic liquid crystal adapted for reorientation in an electric field due to its dielectric anisotropy, and (B) a dichroic dyestuff adapted for simultaneous orientation with said nematic liquid crystal (A) between a light absorption and a light transmission position based on the guest-host effect, said dichroic dyestuff (B) an s-tetrazine derivative with rod-like molecular structure of the formula ##STR7## wherein X is ##STR8## Y is R 2 -- or ##STR9## R 1 is H--, F--, Cl--, Br--, I--, O 2 N--, NC--, HO--, H 2 N, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1 --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC--, C n H 2n+1 CO-- or C n H 2n+1 OCOO--, R 2 is H--, F--, Cl--, Br--, I--, O 2 N--, NC--, HO--, H 2 N--, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1 --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC-- C n H 2n+1 CO-- or C n H 2n+1 OCOO--, R 3 is H--, F--, Cl--, Br--, I--, CH 3 -- or CF 3 --, and R 4 is H--, F--, Cl--, Br--, I--, CH 3 --, or CF 3 --, n is a positive integer.
Claim 2
Dependent Claim
272 words
A nematic liquid crystal composition for modulation of transmitted or incident light, and for rendition of numerals, symbols, and images in color in electro-optical devices, comprising (A) a nematic liquid crystal adapted for reorientation in an electric field due to its dielectric anisotropy, and (B) a dichroic dyestuff adapted for simultaneous orientation with said nematic liquid crystal (A) between a light absorption and a light transmission position based on the guest-host effect, said dichroic dyestuff (B) an s-tetrazine derivative with rod-like molecular structure of the formula ##STR7## wherein X is ##STR8## Y is R 2 -- or ##STR9## R 1 is H--, F--, Cl--, Br--, I--, O 2 N--, NC--, HO--, H 2 N, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1 --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC--, C n H 2n+1 CO-- or C n H 2n+1 OCOO--, R 2 is H--, F--, Cl--, Br--, I--, O 2 N--, NC--, HO--, H 2 N--, C n H 2n+1 NH--, C n H 2n+1 (CH 3 )N--, C n H 2n+1 --, C n H 2n+1 O--, C n H 2n+1 S--, C n H 2n+1 COS--, C n H 2n+1 COO--, C n H 2n+1 OOC-- C n H 2n+1 CO-- or C n H 2n+1 OCOO--, R 3 is H--, F--, Cl--, Br--, I--, CH 3 -- or CF 3 --, and R 4 is H--, F--, Cl--, Br--, I--, CH 3 --, or CF 3 --, n is a positive integer.
Claim 3
Dependent Claim
31 words
The composition of claim 1 wherein said dyestuff (B) is selected from the group consisting of 3-n-alkyl-6-(4-chlorophenyl)-s-tetrazine, 3-hydroxy-6-(4-alkoxyphenyl)-s-tetrazine, 3-phenyl-6-ethoxy-s-tetrazine, 3-phenyl-6-methyl-s-tetrazine, 3-methyl-6-(4-chlorophenyl)-s-tetrazine, 3-(3-methylphenyl)-s-tetrazine, 3-(2-naphthyl)-s-tetrazine, 3,6-bis(4-n-alkylphenyl)-s-tetrazine, 3-(4-n-alkoxyphenyl)-6-alkyl-s-tetrazine, 3-(4-cyano phenyl)-6-n-alkyl-s-tetrazine, 3-(4-n-alkylphenyl)-6-(4-n-alkoxyphenyl)-s-tetrazine, and mixtures thereof.
Claim 4
Dependent Claim
28 words
The composition of claim 2 wherein said dyestuff (B) not in the form of a liquid crystal is present in an amount from 0.5 to 5% by weight.
Claim 5
Dependent Claim
28 words
The composition of claim 2 wherein said dyestuff (B) in the form of a liquid crystal is present in an amount of from 5 to 90% by weight.
Claim 6
Dependent Claim
40 words
The composition of claim 2 wherein said nematic liquid crystal (A) is selected from the group consisting of 5-n-hexyl-2-(4-n-hexoxyphenyl)-pyrimidine, 5-n-hexyl-2-(4-n-nonylphenyl)pyrimidine, 4-n-propylcyclohexanecarboxylic acid 4-cyanophenylester, 4-n-butyl-cyclohexane carboxylic acid 4-cyanophenylester, 4-n-pentylcyclohexanecarboxylic acid 4-cyanophenylester, 4-n-alkylbenzylidene-4'-cyano anilines, 4-n-alkyloxybenzylidene-4'-cyano anilines, 4-cyanophenyl-4'-alkylbenzoates, 4-alkyl-4'-cyanobiphenyls, 4-alkyl-4'-cyclohexylcyclohexanes, and mixtures thereof.
Claim 7
Dependent Claim
10 words
The composition of claim 5 comprising an additional dyestuff (C).
Claim 8
Dependent Claim
30 words
The composition of claim 6 wherein said additional dyestuff (C) is selected from the group consisting of Indophenol blue, Sudanblack B, Isolar Green M, N,N'-dimethylindigo, 4-nitrobenzylidene phenylhydrazine, and mixtures thereof.
Claim 9
Dependent Claim
59 words
The composition of claim 5 wherein (A) said nematic liquid crystal comprises a mixture of 5-n-hexyl-2-(4-n-hexoxyphenyl) pyrimidine and 5-n-hexyl-2-(4-n-nonylphenyl) pyrimidine, in the nematic liquid crystal phase between 4° and 60° C. and exhibiting positive dielectric anistropy, and (B) said dyestuff is 3-(4-methylphenyl)-s-tetrazine, said composition in the nematic liquid crystal phase between 3° and 58° C., assuming a red coloration.
Claim 10
Dependent Claim
39 words
The composition of claim 5 wherein (A) said nematic liquid crystal comprises a mixture of 4-n-propyl-cyclohexane carboxylic acid (4-cyano phenylester), 4-n-butyl-cyclohexanecarboxylic acid (4-cyanophenylester) and 4-n-pentyl-cyclohexanecarboxylic acid (4-cyano phenylester), and (B) said dyestuff is 3-(4-n-pentoxyphenyl)-6-n-pentyl-s-tetrazine, said composition exhibiting red coloration.
Claim 11
Dependent Claim
19 words
The composition of claim 7 wherein (B) said dyestuff is 3-(4-n-pentoxyphenyl)-6-n-pentyl-s-tetrazine, and (C) said additional dyestuff is Indophenol blue.
References Cited (Backward Citations)
US3166399A
Cited
US3703329A
Cited
DE2257588A1
Cited
JPS494532A
Cited
US3960750A
Cited
DD105701A1
Cited
SU498300A1
Cited
US4145114A
Cited
US4137193A
Cited
DD132591A1
Cited
DE2846409A1
Cited
DE2841245A1
Cited
DE2841246A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-06 | 1986-03-08 | 1986-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-06 | 1990-03-08 | 1990-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-06 | 1994-03-08 | 1994-09-07 | $7700.00 | Window Closed / Lapsed |