CA1040653A - Liquid crystal display device - Google Patents
Liquid crystal display deviceInfo
- Publication number
- CA1040653A CA1040653A CA183,464A CA183464A CA1040653A CA 1040653 A CA1040653 A CA 1040653A CA 183464 A CA183464 A CA 183464A CA 1040653 A CA1040653 A CA 1040653A
- Authority
- CA
- Canada
- Prior art keywords
- liquid crystal
- compound
- display device
- crystal display
- nematic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
An electro-optical liquid crystal display device for modulating light beam from a light source uses a novel liquid crystal which exhibits a nematic structure at a room temperature and which has a wide temperature range within which a nematic property thereof is maintained, i.e. 4-normal-butylbenziridene-4'-cyanoaniline
An electro-optical liquid crystal display device for modulating light beam from a light source uses a novel liquid crystal which exhibits a nematic structure at a room temperature and which has a wide temperature range within which a nematic property thereof is maintained, i.e. 4-normal-butylbenziridene-4'-cyanoaniline
Description
104~it The present invention relates to a liquid crystal display device, and more particularly to an electro-optical liquid crystal display device for modulating light beam from a light source by making use of a thin layer of a composition in the form of a nematic liquid crystal having a constant mole-cular orientation.
The present invention thus provides a liquid crystal to be used in an electro-optical liquid crystal display device, which liquid crystal comprises a novel liquid crystal of nematic structure at a room temperature.
The present invention will be more fully understood from the following detailed description of the present invention when taken in conjunction with the accompanying drawings, in which:
Figs. la and lb show a typical liquid crystal display device structure in which Fig. la is an elevational view thereof and Fig. lb is a section taken along the line lb-lb in Fig. la.
Referring to Figs. la and lb, there is shown a typical structure of a liquid crystal display device which comprises a first light transmitting substrate 1 with a first light trans-mitting and electrically conductive films 4, 4', 4" coated on asurface of the first substrate, and a second substrate 2 with a second light transmitting and electrically conductive film 5 coatea on a surface of the second substrate, the space between the first and second substrates 1 and 2 being filled with nematic liquid crystal substance 6 to complete an optical cell, and incident light to the cell being controlable by an electric field or a magnetic field.
The surfaces of the first and second substrates 1 and
The present invention thus provides a liquid crystal to be used in an electro-optical liquid crystal display device, which liquid crystal comprises a novel liquid crystal of nematic structure at a room temperature.
The present invention will be more fully understood from the following detailed description of the present invention when taken in conjunction with the accompanying drawings, in which:
Figs. la and lb show a typical liquid crystal display device structure in which Fig. la is an elevational view thereof and Fig. lb is a section taken along the line lb-lb in Fig. la.
Referring to Figs. la and lb, there is shown a typical structure of a liquid crystal display device which comprises a first light transmitting substrate 1 with a first light trans-mitting and electrically conductive films 4, 4', 4" coated on asurface of the first substrate, and a second substrate 2 with a second light transmitting and electrically conductive film 5 coatea on a surface of the second substrate, the space between the first and second substrates 1 and 2 being filled with nematic liquid crystal substance 6 to complete an optical cell, and incident light to the cell being controlable by an electric field or a magnetic field.
The surfaces of the first and second substrates 1 and
2 and the first and second coating films 4, 4 , 4" and 6 may be treated in such a manner that the liquid crystal molecules at the interfaces are oriented in a preferential direction while main-taining their longitudinal axis in parallel with the first and -1- ~
the second substrates 1 and 2 and the first and second coating films 4, 4', 4" and 6. Polarizers, not shown, may also be positioned on both sides of the electro optical liquid crystal display device, the direction of polarization being selected in parallel with or transverse to each other.
In an optical cell of such a construction, it has been well known in the art that the liquid crystal substance operates to modulate light from a light source under the control of a magnetic field or an electric field.
Many applications of the chemical compounds having a liquid crystal property have also been known. The optical devices disclosed in the prior art technologies, have made the use of compositions having a nematic liquid crystal property which may be applicable to the electro-optical liquid crystal display devices operable at a temperature normally encountered in a residential construction, i.e. in the neighborhood of 25C. The provision of such compositions is highly desirable because it can completely eliminate the need for maintaining the electro-optical liquid crystal display device at a constant temperature.
According to the present invention it has been found that a novel compound 4-normal-butylbenziridene-4'-cyanoaniline having the following formula CH3(CH2)3 ~ CH = N ~ CN (Compound A) which has a crystal-mesomorphic transition temperature of 28.5C
and a mesomorphic-isotropic liquid transition temperature of 51.8C in the form of a liquid crystal exhibits a nematic stru~
cture at room temperature and is useful in a liquid crystal displaying device.
In accordance with the present invention therefore there is provided a liquid crystal display device including a li~uid crystal exhibiting a nematic structure at room temperature consisting o~
~04065~
CH3(CH2)3 ~ CH = N ~ CN.
It has been also found that a mixed liquid crystal having a wide mesomorphic range could be easily produced by adding the compound A to another compound as listed below.
CH3CH2 ~CH = N ~ CN (Compound 1) CH3O ~ CH = N ~ CN (Compound 2) CH3CH2 O ~ CH N ~ CN (Compound 3) CH3(CH2)2 ~ C~ = N ~ CN (Compound 4) 10CH3(CH2)3 O ~ CH = N ~ CN (Compound 5) ; CH3(CH2)4 O ~ CH = N ~ CN (Compound 6) CH3(CH2)5 O~CH = N ~ CN (Compound 7) CH3(CH2)6 O ~ CH = N ~ CN (Compound 8) CH3CH2 C O ~ CH = N ~ CN (Compound 9) (CH2)2 C O ~ CH = N ~ CN (Compound 10) CH3(cH2)4 C O ~ CH = N ~ CN (Compound 11) 20CH3(CH2)6 3 O ~ CH = N ~ CN (Compound 12) CH3 ~ CH = N ~ (CH2)2CH3 (Compound 13) CH3(CH2)3 O ~ CH = N ~ (CH2)3CH3 (Com~ound 14) CH3 O ~ CH N ~ (CH2) 6CH3 (Compound 15) CH (CH2)2 O ~ CH = N ~ (CH2)~CH3 (Compound 16) The mixed liquid crystals having the nematic property are particularly applicabla to the liquid crystal used in the electro-optical liquid crystal display device which utilizes 3Qthe polarization. ~
In preparing the Compound A, 0.10 mole of paranormal- - -butylbenzoaldehyde, CH3 (CH2)3 ~ CHO and p.l0 mole of para-
the second substrates 1 and 2 and the first and second coating films 4, 4', 4" and 6. Polarizers, not shown, may also be positioned on both sides of the electro optical liquid crystal display device, the direction of polarization being selected in parallel with or transverse to each other.
In an optical cell of such a construction, it has been well known in the art that the liquid crystal substance operates to modulate light from a light source under the control of a magnetic field or an electric field.
Many applications of the chemical compounds having a liquid crystal property have also been known. The optical devices disclosed in the prior art technologies, have made the use of compositions having a nematic liquid crystal property which may be applicable to the electro-optical liquid crystal display devices operable at a temperature normally encountered in a residential construction, i.e. in the neighborhood of 25C. The provision of such compositions is highly desirable because it can completely eliminate the need for maintaining the electro-optical liquid crystal display device at a constant temperature.
According to the present invention it has been found that a novel compound 4-normal-butylbenziridene-4'-cyanoaniline having the following formula CH3(CH2)3 ~ CH = N ~ CN (Compound A) which has a crystal-mesomorphic transition temperature of 28.5C
and a mesomorphic-isotropic liquid transition temperature of 51.8C in the form of a liquid crystal exhibits a nematic stru~
cture at room temperature and is useful in a liquid crystal displaying device.
In accordance with the present invention therefore there is provided a liquid crystal display device including a li~uid crystal exhibiting a nematic structure at room temperature consisting o~
~04065~
CH3(CH2)3 ~ CH = N ~ CN.
It has been also found that a mixed liquid crystal having a wide mesomorphic range could be easily produced by adding the compound A to another compound as listed below.
CH3CH2 ~CH = N ~ CN (Compound 1) CH3O ~ CH = N ~ CN (Compound 2) CH3CH2 O ~ CH N ~ CN (Compound 3) CH3(CH2)2 ~ C~ = N ~ CN (Compound 4) 10CH3(CH2)3 O ~ CH = N ~ CN (Compound 5) ; CH3(CH2)4 O ~ CH = N ~ CN (Compound 6) CH3(CH2)5 O~CH = N ~ CN (Compound 7) CH3(CH2)6 O ~ CH = N ~ CN (Compound 8) CH3CH2 C O ~ CH = N ~ CN (Compound 9) (CH2)2 C O ~ CH = N ~ CN (Compound 10) CH3(cH2)4 C O ~ CH = N ~ CN (Compound 11) 20CH3(CH2)6 3 O ~ CH = N ~ CN (Compound 12) CH3 ~ CH = N ~ (CH2)2CH3 (Compound 13) CH3(CH2)3 O ~ CH = N ~ (CH2)3CH3 (Com~ound 14) CH3 O ~ CH N ~ (CH2) 6CH3 (Compound 15) CH (CH2)2 O ~ CH = N ~ (CH2)~CH3 (Compound 16) The mixed liquid crystals having the nematic property are particularly applicabla to the liquid crystal used in the electro-optical liquid crystal display device which utilizes 3Qthe polarization. ~
In preparing the Compound A, 0.10 mole of paranormal- - -butylbenzoaldehyde, CH3 (CH2)3 ~ CHO and p.l0 mole of para-
3 -.
.
cyanoaniline, CN ~ NH2 were refluxed in a solvent of 500 ml of benzene for foux hours in a 1000 ml round bottom flask provided with a reflux condenser including a calcium chloride drying tube.
A Dean-Stark trap is used to collect the water which is azeo-tropically removed. After refluxing, the solvent is removed by evaporation under reduced pressure in a rotary evaporator.
The residue is collected and recrystallized from isopropyl alcohol.
The recrystallization process is repeated until a constant melting point is reached. Compounds 1 through 16 are also prepared and purified in the same manner.
A small number of compounds having a nematic crystal property exist which are in the form of simple substance and exhibit liquid crystal state at a room temperature. The temperature range within which the nematic property is substained is relatively narrow for those compounds. Thus, it has been investigated heretofore to use the mixed liquid crystal consisting of more than one compound in order to make it possible for the mixture to exhibit a liquid crystal state at or below a room temperature and to provide a wider temperature range within which the nematic property is sustained. Several examples thereof are given in the following Table 1.
.
~ ~,,', .
1040t;S3 ~ ~ ~ ~ ;3 ~Q ~ ~ ~ : ' W
O O ~ ~ O ~ ~3 o ~ ~
~ ~ O
~3 ~ ~3 ~ ~3 (~ ,.
Z ~: ~ ~ ~ ~ ~ Z ~ ~ X' ~ ~ 11 ~ ~ , ~ ~ ~
O OQ Z Z O ~ ~ ~ ~ ~) ) 1--~ -~ ~ ~ ~Q ~ .
r~ o z Q ~ Q Q Q 10 ~_ Q ~ ~_ m m m o 11 ~ ~ ~ ~ In x m ~Q r~ ~ ll 1I mQ ~
~ ~ Qm ~ m ~ ~ IJ
~ ~ o o ~
o ~m m ~
~ ~ ~ ~o p~
. ~1 I- :
~QC ~
1- ~ I- ~D
~( ~ O O O O
~a ~ ~ ~ ~ ~ ~ ~ ~:
~ ~ ~ ~ ~ ~ ~ ~ eq ~ . ~:
~D ~ ~ .~ :.
(D tD ~D ~ I'~ IJ- 1'- 1'-IJ- I'- ~''- ~ Oq (Jq t1CI oCI ~ Oq aq oq vq 5 ~ ~ ~5 ~ ~ ~
t ~ ~ ~ .--- .
., ~ ~ ' ~ :'~ ~
IV l I_ I~ ~ ~ ' -1- ~C) I~ P~
~-O 1- ~ ~ (D I'~
Q ~0 Q Q ~0~
~t ~`
.
,~ ~ :
r~
' ' ~ .' . ' ' ~' ' .
', ' .
104~653 ~C
o (~)o ~o ~:; @i ~Q O O
(~ Q ~ ::~
:~ Q=O ~ ~ ~C- :
Z Z 11 ~ ~ ~ ~ ~ ~ Q~
O Q O ~) ~ ~-Z Z O=Q [~ ~, ~ Q=o~ ~
~ . ~ :.
I æ ~ ~;3 ~ O
X . ~ ,'~ ' :~
o~ o o ~ o o I ~ ~
~, _ . . _ _ ~Q ~ H
a ~) ~ l F O ~ -:-~0 ~0 o ID I'~ ~
_ 6 .j , , .
' ' . ... ~ . .
.: , .
~os~ ~ .
The present invention provides mixed liquid crystals having wider temperature range for nematic maintainence and exhibiting a nematic phase at room temperature obtained by mix-ing the novel Compound A having the nematic property with another compound of benziridene-4'-cyanoaniline in a suitable proportion.
The examples of the mixture are given in Table 2 below.
Table 2 _ _ _ _ _ _ Composition of Proportion in Temperature range mixed liquid for nematic property crystal % by weight sustenance _ _ _ -- :
Compound A 75 Below OC-37.3C
Compound 1 25 _ :
Compound A 75 Below OC-56.0C
Compound 2 25 ~ ~
_. : .
Compound A 75 23.0 -67.2C
Compound 3 25 Compound A 80 25.0 - 48.9C ~
Compound 4 20 _ -Compound A 50 13.2 - 75.8C
Compound 6 50 ~. .., . - . .
Compound A 50 14.0 - 79.0C
Compound 7 50 Compound A 67 Below 0C-54.0C
Compound 8 33 _ .
. .
L;~, ~ 7 ~ .. . . . . .. , . . - : .
104~6S3 Composition of Proportion in temperature range mixed liquid for nematic property crystal % by weight sustenance Compound A 83 : 11.0-40.6C
CCompound 9 17 Compound A 75 25.0 - 42.2C
Compound 10 25 Compound A 50 6.0 - 66.2C
Compound 11 50 : Compound A 50 : 15.0 - 75.6C
Compound 12 50 Compound A 33.3 Compound 7 33.3 Below -25C-80.6C
Compound 12 33.3 Compound A 33.3 Compound 5 33.3 Below -25C-83.3C
Compound 6 33.3 Compound A 50 ` Compound 5 25 Below -25C-76.1C
Compound 12 25 Compound A 33.3 Compound 5 33.3 18.0 - 86.6C
Compound 7 33.3 .. , ~
~ - 8 - :
.
, . . .
1~41~)653 Composition of Proportion in temperature range mixed liquid for nematic property crystal % by weight sustenance Compound ~ 33.3 Compound 13 33.3 1~.0 - 57.2C
Compound 1~ 33.3 ;
Compound A 33.3 Compol~nd 15 33.3 20.0 - 59.3C
Compound 16 33.3 1 Following organic substances may be further added to the Compound A in the form of single sub-stance or the mixture of the Compound A with the Compounds 1 - 16.
5 (1) Pigmentary additive for presenting a poly-chromatic property~ such as methy] Red or indophenol blue.
(2) Additive for improving durability~ such as hydroquinone or 2~ 4~ 6-tri-tertiary-butylphenol.
! These organic substances may be mixed as required. As described hereinabove, the liquid crystal display device according to the present invention uses a novel liquid crystal having a broad temperature ~: 15 range for nematic property sustenance and exhibiting the nematic property at a room temperature, as a liquid crystal used for the electro-optical liquid crystal display device for modulating light beam from a light source. Accordingly~ the device of the present inven-_ g _ , .. . . . . .. . . . .
. : : . .. . . .: . . .
' '' ~ .. . '. " .. .... ' :' ' , . . .
1~4~653 1 tion also provides the same advantages and is valuable in industrial applications.
; . ,~
i ~ :
~ .
: ~ " ' . ' - -- 1.0 -,~
.
cyanoaniline, CN ~ NH2 were refluxed in a solvent of 500 ml of benzene for foux hours in a 1000 ml round bottom flask provided with a reflux condenser including a calcium chloride drying tube.
A Dean-Stark trap is used to collect the water which is azeo-tropically removed. After refluxing, the solvent is removed by evaporation under reduced pressure in a rotary evaporator.
The residue is collected and recrystallized from isopropyl alcohol.
The recrystallization process is repeated until a constant melting point is reached. Compounds 1 through 16 are also prepared and purified in the same manner.
A small number of compounds having a nematic crystal property exist which are in the form of simple substance and exhibit liquid crystal state at a room temperature. The temperature range within which the nematic property is substained is relatively narrow for those compounds. Thus, it has been investigated heretofore to use the mixed liquid crystal consisting of more than one compound in order to make it possible for the mixture to exhibit a liquid crystal state at or below a room temperature and to provide a wider temperature range within which the nematic property is sustained. Several examples thereof are given in the following Table 1.
.
~ ~,,', .
1040t;S3 ~ ~ ~ ~ ;3 ~Q ~ ~ ~ : ' W
O O ~ ~ O ~ ~3 o ~ ~
~ ~ O
~3 ~ ~3 ~ ~3 (~ ,.
Z ~: ~ ~ ~ ~ ~ Z ~ ~ X' ~ ~ 11 ~ ~ , ~ ~ ~
O OQ Z Z O ~ ~ ~ ~ ~) ) 1--~ -~ ~ ~ ~Q ~ .
r~ o z Q ~ Q Q Q 10 ~_ Q ~ ~_ m m m o 11 ~ ~ ~ ~ In x m ~Q r~ ~ ll 1I mQ ~
~ ~ Qm ~ m ~ ~ IJ
~ ~ o o ~
o ~m m ~
~ ~ ~ ~o p~
. ~1 I- :
~QC ~
1- ~ I- ~D
~( ~ O O O O
~a ~ ~ ~ ~ ~ ~ ~ ~:
~ ~ ~ ~ ~ ~ ~ ~ eq ~ . ~:
~D ~ ~ .~ :.
(D tD ~D ~ I'~ IJ- 1'- 1'-IJ- I'- ~''- ~ Oq (Jq t1CI oCI ~ Oq aq oq vq 5 ~ ~ ~5 ~ ~ ~
t ~ ~ ~ .--- .
., ~ ~ ' ~ :'~ ~
IV l I_ I~ ~ ~ ' -1- ~C) I~ P~
~-O 1- ~ ~ (D I'~
Q ~0 Q Q ~0~
~t ~`
.
,~ ~ :
r~
' ' ~ .' . ' ' ~' ' .
', ' .
104~653 ~C
o (~)o ~o ~:; @i ~Q O O
(~ Q ~ ::~
:~ Q=O ~ ~ ~C- :
Z Z 11 ~ ~ ~ ~ ~ ~ Q~
O Q O ~) ~ ~-Z Z O=Q [~ ~, ~ Q=o~ ~
~ . ~ :.
I æ ~ ~;3 ~ O
X . ~ ,'~ ' :~
o~ o o ~ o o I ~ ~
~, _ . . _ _ ~Q ~ H
a ~) ~ l F O ~ -:-~0 ~0 o ID I'~ ~
_ 6 .j , , .
' ' . ... ~ . .
.: , .
~os~ ~ .
The present invention provides mixed liquid crystals having wider temperature range for nematic maintainence and exhibiting a nematic phase at room temperature obtained by mix-ing the novel Compound A having the nematic property with another compound of benziridene-4'-cyanoaniline in a suitable proportion.
The examples of the mixture are given in Table 2 below.
Table 2 _ _ _ _ _ _ Composition of Proportion in Temperature range mixed liquid for nematic property crystal % by weight sustenance _ _ _ -- :
Compound A 75 Below OC-37.3C
Compound 1 25 _ :
Compound A 75 Below OC-56.0C
Compound 2 25 ~ ~
_. : .
Compound A 75 23.0 -67.2C
Compound 3 25 Compound A 80 25.0 - 48.9C ~
Compound 4 20 _ -Compound A 50 13.2 - 75.8C
Compound 6 50 ~. .., . - . .
Compound A 50 14.0 - 79.0C
Compound 7 50 Compound A 67 Below 0C-54.0C
Compound 8 33 _ .
. .
L;~, ~ 7 ~ .. . . . . .. , . . - : .
104~6S3 Composition of Proportion in temperature range mixed liquid for nematic property crystal % by weight sustenance Compound A 83 : 11.0-40.6C
CCompound 9 17 Compound A 75 25.0 - 42.2C
Compound 10 25 Compound A 50 6.0 - 66.2C
Compound 11 50 : Compound A 50 : 15.0 - 75.6C
Compound 12 50 Compound A 33.3 Compound 7 33.3 Below -25C-80.6C
Compound 12 33.3 Compound A 33.3 Compound 5 33.3 Below -25C-83.3C
Compound 6 33.3 Compound A 50 ` Compound 5 25 Below -25C-76.1C
Compound 12 25 Compound A 33.3 Compound 5 33.3 18.0 - 86.6C
Compound 7 33.3 .. , ~
~ - 8 - :
.
, . . .
1~41~)653 Composition of Proportion in temperature range mixed liquid for nematic property crystal % by weight sustenance Compound ~ 33.3 Compound 13 33.3 1~.0 - 57.2C
Compound 1~ 33.3 ;
Compound A 33.3 Compol~nd 15 33.3 20.0 - 59.3C
Compound 16 33.3 1 Following organic substances may be further added to the Compound A in the form of single sub-stance or the mixture of the Compound A with the Compounds 1 - 16.
5 (1) Pigmentary additive for presenting a poly-chromatic property~ such as methy] Red or indophenol blue.
(2) Additive for improving durability~ such as hydroquinone or 2~ 4~ 6-tri-tertiary-butylphenol.
! These organic substances may be mixed as required. As described hereinabove, the liquid crystal display device according to the present invention uses a novel liquid crystal having a broad temperature ~: 15 range for nematic property sustenance and exhibiting the nematic property at a room temperature, as a liquid crystal used for the electro-optical liquid crystal display device for modulating light beam from a light source. Accordingly~ the device of the present inven-_ g _ , .. . . . . .. . . . .
. : : . .. . . .: . . .
' '' ~ .. . '. " .. .... ' :' ' , . . .
1~4~653 1 tion also provides the same advantages and is valuable in industrial applications.
; . ,~
i ~ :
~ .
: ~ " ' . ' - -- 1.0 -,~
Claims (4)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A liquid crystal display device including a liquid crystal exhibiting a nematic structure at room temperature con-sisting of .
2. A liquid crystal display device including a liquid crystal exhibiting a nematic structure at room temperature con-sisting of and an organic substance selected from methyl red, indophenol blue, hydroquinone and 2,4,6-tri-tertiary butyl phenol.
3. A liquid crystal display device including a liquid crystal exhibiting a nematic structure at room temperature con-sisting of , an organic substance selected from methyl red, indophenol blue, hydroquinone and 2,4,6-tri-tertiary butyl phenol, and at least one substance selected from the group consisting of , , , , , , , , , , , , , , , and .
4. A compound of the formula given in claim 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10428272A JPS4962390A (en) | 1972-10-17 | 1972-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040653A true CA1040653A (en) | 1978-10-17 |
Family
ID=14376557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA183,464A Expired CA1040653A (en) | 1972-10-17 | 1973-10-16 | Liquid crystal display device |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4962390A (en) |
| CA (1) | CA1040653A (en) |
| DE (1) | DE2351684A1 (en) |
| FR (1) | FR2202731B1 (en) |
| GB (1) | GB1437809A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4058477A (en) * | 1972-02-23 | 1977-11-15 | Hoffmann-La Roche Inc. | Liquid crystal Schiffs bases |
| US4043634A (en) * | 1974-07-25 | 1977-08-23 | Dai Nippon Toryo Co., Ltd. | Liquid crystal electro optical element |
| JPS5117189A (en) * | 1974-08-02 | 1976-02-10 | Dainippon Printing Co Ltd | NEMACHITSU KUEKISHOSOSEIBUTSU |
| FR2294223A1 (en) * | 1974-12-13 | 1976-07-09 | Dainippon Toryo Kk | Electro-optical liquid crystal element - contg p-N-alkyl-benzylidine-p'-cyano-aniline, alkyl-cyanobenzene, alkyl-benzylidene-alkoxy-aniline and or alkoxy benzylidene-alkyl-aniline |
| JPS5235183A (en) * | 1975-09-12 | 1977-03-17 | Hitachi Ltd | Liquid crystal composition for electoric field effect type display |
| DE2557267A1 (en) * | 1975-12-19 | 1977-06-30 | Bbc Brown Boveri & Cie | LIQUID CRYSTAL SUBSTANCE |
| US4147656A (en) * | 1976-06-28 | 1979-04-03 | Itek Corporation | Mixtures of nematic liquid crystal materials |
| CH626914A5 (en) * | 1977-03-08 | 1981-12-15 | Bbc Brown Boveri & Cie | |
| JPS63205319A (en) * | 1987-02-20 | 1988-08-24 | Hitachi Ltd | Schiff bond-containing compound, its polymer and production thereof |
| WO2023180662A1 (en) | 2022-03-25 | 2023-09-28 | Psa Automobiles Sa | Autonomous transport device with platform and on-board lifting system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795775A (en) * | 1972-02-23 | 1973-08-22 | Hoffmann La Roche | LIQUID CRYSTALLINE SCHIFF BASES |
-
1972
- 1972-10-17 JP JP10428272A patent/JPS4962390A/ja active Pending
-
1973
- 1973-10-15 GB GB4853773A patent/GB1437809A/en not_active Expired
- 1973-10-15 DE DE19732351684 patent/DE2351684A1/en active Pending
- 1973-10-16 FR FR7336854A patent/FR2202731B1/fr not_active Expired
- 1973-10-16 CA CA183,464A patent/CA1040653A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2202731A1 (en) | 1974-05-10 |
| FR2202731B1 (en) | 1977-05-27 |
| GB1437809A (en) | 1976-06-03 |
| JPS4962390A (en) | 1974-06-17 |
| DE2351684A1 (en) | 1974-04-18 |
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