CA1049249A - Nematic liquid crystal compositions - Google Patents
Nematic liquid crystal compositionsInfo
- Publication number
- CA1049249A CA1049249A CA227,212A CA227212A CA1049249A CA 1049249 A CA1049249 A CA 1049249A CA 227212 A CA227212 A CA 227212A CA 1049249 A CA1049249 A CA 1049249A
- Authority
- CA
- Canada
- Prior art keywords
- liquid crystal
- cyanophenyl
- nematic liquid
- component
- weight
- 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
- 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
- C09K19/20—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 oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—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 oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
Abstract
Nematic Liquid Crystal Compositions Abstract of the Disclosure Nematic liquid crystal compositions having positive dielectric anisotropy are obtained by mixing at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by the formula, wherein R2 is n-alkyl group of 3 to 8 carbon atoms with at least one of p-cyanophenyl-p'-n-alkylbenzoates represented by the formula, wherein R1 is n-alkyl group of 4 to 8 carbon atoms.
Said compositions exhibit nematic liquid crystal phase over a broad temperature range and therefore, are useful for the torsion effect-type display device.
Said compositions exhibit nematic liquid crystal phase over a broad temperature range and therefore, are useful for the torsion effect-type display device.
Description
Backgroud of the Invention:
This invention relates to a new nematic liquid crystal composition having positive dielectric anisotropy.
Nematic liquid crystal compounds or nematic liquid crystal compositions (hereinafter referred to as N-liquid crystal materials) are used for electro-optical display devices, utilizing the phenomenon that they are optically ch~nged if an electric field is applied thereto. ~lectro-optical display devices with use of the N-liquid crystal ~aterial may be divided ~nto two groups according to dielectric anisotropy of the N-liquid crystal material used.
1049;~9 Ono group comprises de~ices $n which there i~ employed a dyn~mic ~cattering mode (DSM), i.e. an optical scattering phenomenon caused by collision of an ion with a domain J when an electric field i8 applied to a N-liquid crystal S material having larger dielectric constant in a direction psrpendicular to longitudinal axes of the molecules than dielectric constant in the longitudinal direction, i.e.
nematic liquid crystal material having negative dielectric ~nisotropy (hereinafter referred to as Nn-liquid crystal material). Another group comprises devices in which there i~ employed an electric field effect mode (FEM), i.e. a change in lean or torsion of N-liquid crystal molecules caused by applying an electric field to an N-liquid crystal ~aterial having larger dielectric constant in a longitudinal direction of the molecules than that in a direction perpendicular to longitudinal axe~ of the molecules, i.e.
nematic liquid crystal material having positive dielectric ani~otropy ~hereinafter referred to as Np-liquid crystal material). Many of the latter FEM-type devices are so-called ~torsion effect-type display devices~ (hereinafter referred to as TN-type display device) wherein a change in torsion of the molecules (one of the electric field effect modes) is utilized. The Np-liquid crystal composition of this invention is utilized for the TN-type display device.
As one of well-known Np-liquid crystal compounds, there are p-cyanophenyl-p'-n-alkylbenzoates having Formula I, ~ C-O-- ~ C~N
wherein Rl is n-alkyl of 4 to 8 carbons atoms, which is disclosed in United States Patent 4,058,478.
The compounds of Formula I are limited in a temperature range exhibiting nematic liquid crystal phase ~hereinafter referred to as "mesomorphic range") as set forth in Table I, but Np-liquid crystal compositions having a broad mesomorphic range can be obtained by mixing two or more of these compounds.
With reference to a Np-liquid crystal composition consisting of a mixture of two p-cyanophenyl-p'-n-alkylben~oates, its phase diagram is shown in Fig. 1 and Fig. 2 Table 1 Np-liquid crystal compounds ¦ Mesomorphic ranges i CH3 (CH ) - ~ -C-O- ~ -C_N m.p. 67C
This invention relates to a new nematic liquid crystal composition having positive dielectric anisotropy.
Nematic liquid crystal compounds or nematic liquid crystal compositions (hereinafter referred to as N-liquid crystal materials) are used for electro-optical display devices, utilizing the phenomenon that they are optically ch~nged if an electric field is applied thereto. ~lectro-optical display devices with use of the N-liquid crystal ~aterial may be divided ~nto two groups according to dielectric anisotropy of the N-liquid crystal material used.
1049;~9 Ono group comprises de~ices $n which there i~ employed a dyn~mic ~cattering mode (DSM), i.e. an optical scattering phenomenon caused by collision of an ion with a domain J when an electric field i8 applied to a N-liquid crystal S material having larger dielectric constant in a direction psrpendicular to longitudinal axes of the molecules than dielectric constant in the longitudinal direction, i.e.
nematic liquid crystal material having negative dielectric ~nisotropy (hereinafter referred to as Nn-liquid crystal material). Another group comprises devices in which there i~ employed an electric field effect mode (FEM), i.e. a change in lean or torsion of N-liquid crystal molecules caused by applying an electric field to an N-liquid crystal ~aterial having larger dielectric constant in a longitudinal direction of the molecules than that in a direction perpendicular to longitudinal axe~ of the molecules, i.e.
nematic liquid crystal material having positive dielectric ani~otropy ~hereinafter referred to as Np-liquid crystal material). Many of the latter FEM-type devices are so-called ~torsion effect-type display devices~ (hereinafter referred to as TN-type display device) wherein a change in torsion of the molecules (one of the electric field effect modes) is utilized. The Np-liquid crystal composition of this invention is utilized for the TN-type display device.
As one of well-known Np-liquid crystal compounds, there are p-cyanophenyl-p'-n-alkylbenzoates having Formula I, ~ C-O-- ~ C~N
wherein Rl is n-alkyl of 4 to 8 carbons atoms, which is disclosed in United States Patent 4,058,478.
The compounds of Formula I are limited in a temperature range exhibiting nematic liquid crystal phase ~hereinafter referred to as "mesomorphic range") as set forth in Table I, but Np-liquid crystal compositions having a broad mesomorphic range can be obtained by mixing two or more of these compounds.
With reference to a Np-liquid crystal composition consisting of a mixture of two p-cyanophenyl-p'-n-alkylben~oates, its phase diagram is shown in Fig. 1 and Fig. 2 Table 1 Np-liquid crystal compounds ¦ Mesomorphic ranges i CH3 (CH ) - ~ -C-O- ~ -C_N m.p. 67C
2 3 11 4~ . 5 C ~monotropic CH3 (C~2)4 ~ -C-O- ~ -C=-N m.p. 60.5C
Il ~ 56.5C~ monotropic , CH3 (CH2)5 ~ -C-O- ~ -C-N 45~ 48C
CH3-(CH2)6- ~ -C-O- ~ -C=N 44 ~ 56.5C
CH3 (CH2)7 ~ -b-- ~ -C_N 46.5~ 53.5C
`~ .
A ~lxtuse of three p-cyanoph~nyl-p'-n-~lkylbenzoates ha~ ln general a mesomorphic ran~Q broad~r than that of ~lxture of t~o p-cyanophenyl-p'-n-alkylben20ates. A~ong them, partlcularly a ~l~ture ln equal parts by we~ght of p-cyanopheny~-p'-n-butylbanzoate~ p-cyanophenyl-p'-n-he~ylbenzoa~e a~d p-cyanophe~yl-p'-n-octylbenzoate has re~arkdbly broad me~omorph$c range, i.e. 7 to 47.5-C.
T~e compounds o~ the Formula ~ and mixtures thereof ar~ a Np-l~qu$d cry~tal material wlth good chemical ~tablll~y, ~t are limlted ln a ~e~omorph~c range, particu-larly in a low temper~ture ~one a~ compared ~th other ~p-llquld cry~tal matsrlal~, for example p-alkylbenzylidene-p'-cyanoanilin~ of the formula, N-C- ~ -N-C~
~hereln ~ i8 ethyl, n-propyl, n-butyl, n-pentyl, i-hexyl, n-hexyl, n-beptyl and n-octyl, and ~ixture~ thereof.
For thls reason, the Np-liquid crystal materials of Fo~mula I
are prevented from the w e ~n the TN type display devlce.
Su~mary of the Invention An ob~ect of th~ ~nvention 18 to provide u~eful Np-llqula cry~tal compositions for the TN type display device, ~hlch exhibit nematic liquid crystal phase over a broad ~ temperature rango.
The foregoing can be attalned by mixing ~A) at least one of p-cyanophenYI-p~-n-alkylbenzoates of tho Formula I
with (B) at least one of p-n-alkylphenyl-p'-cyanobenzoate represented by For~ula II, UL--C- ~ -C--- ~ R2 II
iO49Z49 wherein R2 is n-alkyl of 3 to 8 carbon atoms to form Np-liquid crystal compositions, an amount of said component B
being within the range of not more than abaut 30% by weight based on the total amount of the composition.
Brief Description of Drawings Fig. 1 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-butylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Fig. 2 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Detailed Description of the Invention In accordance with this invention, by mixing at least one of the compounds of the Formula I and at least one of the compounds of the Formula II in amounts as defined above, there are provided Np-liquid crystal compositions which have a broad mesomorphic range, particularly broadened in, a low temperature zone as compared with that of the Np-liquid crystal material of the Formula I.
The compounds of the Formula II themselves are a Np-liquid crystal material and are characteristic of monotropy except p-n-octylphenyl-p'-cyanobenzoate.
Mesomorphic ranges of these compounds are given in Table 2.
io4sz4s Table 2 - _ Np-liquid crystal compounds Mesomorphic ranges N--C ~ -~-0- ~ -(CH2)2.CH3 68C ~monotropic .. .
N--C- ~ -l_0_ ~ _(CH2)3.CH3 m.p.75C
0 59 C~ monotropic N-C- ~ -C-O- ~ -(CH2)4.CH3 73C~-monotropic . _ N--C- ~ -C-O- ~ -(CH2)5.CH3 m.p.73C
70 C ~ monotropic . ~ - - _ N--C- ~ -C-O- ~ -(CH2)6.CH3 m p 78C
--- ------N-C- ~ -C-O- ~ -(CH2)7.CH3 66 ~71C
!
The p-n-alkylphenyl-p'-cyanobenzoates of the Formula II may, for example, be prepared by mixing p-cyanobenzoyl chloride and p-n-alkylphenol in equal molar amounts, heating the mixture in anhydrous pyridine and benzene while stirring, and after extraction with ether, washing the reaction product with dilute hydrochloric acid, aqueous - 1049'~49 .
! solution of sodium hydroxide and then water.
The above reaction may be illustrated as follows:
N-C ~ COCb + ~ ~ ~2 ~~~~ N--C ~ C-0 ~ ~
me 6tarting p-n-alkylphenol ~ay be obtained by preparing - the diazonium salt from p-n-alkylaniline and then hydro-lyzing same. p-n-Alkylphenyl-p'-cyanobenzoate~ obtained thus are purified by repeating recrystallization from ethanol. These compounds are chemically stable and exhibit good miscibility with p-cyanophenyl-p'-n- `~
alkylbenzoates.
In the Np-l quid crystal composition of this invention, p-n-alkylphenyl-p'-cyanobenzoate~ (component B) should be in an amount of not more than about 30% by weight based on th~ total a~ount of the compo~ition. When the amount is re than about 30% by weight, the resulting composition becomes narrower in the mesomorphic range than p-cyanophenyl-p'-n-alkylbanzoates (component A) alone and therefore, the ob~ect of this invention can not be attaine~.
Particularly, when the amount of the component B is within the range of about 10 to 25% by weight, compositions having broader mesomorphic range can be obtained.
In accordance with particularly, preferred embodiments of thi~ invention, there are provided Np-liquid crystal compositions having remarkably broad mesomorphic r~nge, ~hich consist of a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate as the component A and p-n-butylphenyl-p'-cyanobenzoate, p-n-hexylphenyl-p'-cyanobenzoate or p-n-octylphenyl-p'-cyanobenzoate as the component B in the amount as defined above.
The Np-liquid crystal cornpositions of this invention are chemically stable and have the mesomorphic range broader particularly, in a low temperature zone than that of p-cyanophenyl-p'-n-alkylbenzoates of the component A, and therefore, are useful for the TN-type display device.
This invention will be illustrated by the following non-limitative examples.
p-n-Alkylphenyl-p'-cyanobenzoates (component B) used in the examples were prepared in accordance with the process as described herein~efore.
Example 1 A Np-liquid crystal composition having a mesomorphic range of 34 to 49.0C was obtained by mixing 80% by weight of p-cyanophenyl-p'-n-hexylbenzoate (mesomorphic range :
48C) and 20% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, Np-liquid crystal compositions were obtained by mixing the components A and B as set forth in Table 3.
Mesomorphic ranges of these compositions are also in Table 3.
. ~ ~ ~
1049'~49 .C t~ o ~ o o ~ o o o In u~ o u~
~ .
~ . o~ 1 o~
t ~ ~ ~ ~ u~ u~
~ t~ ¢ ~ ~ ~ ~ ~
~: ~ ~ ~ ~ ~ ~ ~ ~r ~ ~ ~ ~
~ o o o o o o U~ o U~ o ~ o P N N t~l N N N _I ~I N
J~ . - .. .. .. .. .. .. ..
o o o o o o u~ o u~ o In o ~ ~ ~ co eo ~ ~ ~
. ~ ._ 2 ~: Q ~ ~ ~ ~
~ ~ ~ r~
~ - ~ - ~ - -'3 U ~ 5~ ~ ~ ~ U
: ~ u=ou=ocl~=o u=ou=o~=o ~l-~ l ~ ~ ~ ~ o~
,u,l ~b ,u" ~ ~ ~' ~ .
& -
Il ~ 56.5C~ monotropic , CH3 (CH2)5 ~ -C-O- ~ -C-N 45~ 48C
CH3-(CH2)6- ~ -C-O- ~ -C=N 44 ~ 56.5C
CH3 (CH2)7 ~ -b-- ~ -C_N 46.5~ 53.5C
`~ .
A ~lxtuse of three p-cyanoph~nyl-p'-n-~lkylbenzoates ha~ ln general a mesomorphic ran~Q broad~r than that of ~lxture of t~o p-cyanophenyl-p'-n-alkylben20ates. A~ong them, partlcularly a ~l~ture ln equal parts by we~ght of p-cyanopheny~-p'-n-butylbanzoate~ p-cyanophenyl-p'-n-he~ylbenzoa~e a~d p-cyanophe~yl-p'-n-octylbenzoate has re~arkdbly broad me~omorph$c range, i.e. 7 to 47.5-C.
T~e compounds o~ the Formula ~ and mixtures thereof ar~ a Np-l~qu$d cry~tal material wlth good chemical ~tablll~y, ~t are limlted ln a ~e~omorph~c range, particu-larly in a low temper~ture ~one a~ compared ~th other ~p-llquld cry~tal matsrlal~, for example p-alkylbenzylidene-p'-cyanoanilin~ of the formula, N-C- ~ -N-C~
~hereln ~ i8 ethyl, n-propyl, n-butyl, n-pentyl, i-hexyl, n-hexyl, n-beptyl and n-octyl, and ~ixture~ thereof.
For thls reason, the Np-liquid crystal materials of Fo~mula I
are prevented from the w e ~n the TN type display devlce.
Su~mary of the Invention An ob~ect of th~ ~nvention 18 to provide u~eful Np-llqula cry~tal compositions for the TN type display device, ~hlch exhibit nematic liquid crystal phase over a broad ~ temperature rango.
The foregoing can be attalned by mixing ~A) at least one of p-cyanophenYI-p~-n-alkylbenzoates of tho Formula I
with (B) at least one of p-n-alkylphenyl-p'-cyanobenzoate represented by For~ula II, UL--C- ~ -C--- ~ R2 II
iO49Z49 wherein R2 is n-alkyl of 3 to 8 carbon atoms to form Np-liquid crystal compositions, an amount of said component B
being within the range of not more than abaut 30% by weight based on the total amount of the composition.
Brief Description of Drawings Fig. 1 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-butylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Fig. 2 represents a phase diagram of a Np-liquid crystal composition consisting of p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate.
Detailed Description of the Invention In accordance with this invention, by mixing at least one of the compounds of the Formula I and at least one of the compounds of the Formula II in amounts as defined above, there are provided Np-liquid crystal compositions which have a broad mesomorphic range, particularly broadened in, a low temperature zone as compared with that of the Np-liquid crystal material of the Formula I.
The compounds of the Formula II themselves are a Np-liquid crystal material and are characteristic of monotropy except p-n-octylphenyl-p'-cyanobenzoate.
Mesomorphic ranges of these compounds are given in Table 2.
io4sz4s Table 2 - _ Np-liquid crystal compounds Mesomorphic ranges N--C ~ -~-0- ~ -(CH2)2.CH3 68C ~monotropic .. .
N--C- ~ -l_0_ ~ _(CH2)3.CH3 m.p.75C
0 59 C~ monotropic N-C- ~ -C-O- ~ -(CH2)4.CH3 73C~-monotropic . _ N--C- ~ -C-O- ~ -(CH2)5.CH3 m.p.73C
70 C ~ monotropic . ~ - - _ N--C- ~ -C-O- ~ -(CH2)6.CH3 m p 78C
--- ------N-C- ~ -C-O- ~ -(CH2)7.CH3 66 ~71C
!
The p-n-alkylphenyl-p'-cyanobenzoates of the Formula II may, for example, be prepared by mixing p-cyanobenzoyl chloride and p-n-alkylphenol in equal molar amounts, heating the mixture in anhydrous pyridine and benzene while stirring, and after extraction with ether, washing the reaction product with dilute hydrochloric acid, aqueous - 1049'~49 .
! solution of sodium hydroxide and then water.
The above reaction may be illustrated as follows:
N-C ~ COCb + ~ ~ ~2 ~~~~ N--C ~ C-0 ~ ~
me 6tarting p-n-alkylphenol ~ay be obtained by preparing - the diazonium salt from p-n-alkylaniline and then hydro-lyzing same. p-n-Alkylphenyl-p'-cyanobenzoate~ obtained thus are purified by repeating recrystallization from ethanol. These compounds are chemically stable and exhibit good miscibility with p-cyanophenyl-p'-n- `~
alkylbenzoates.
In the Np-l quid crystal composition of this invention, p-n-alkylphenyl-p'-cyanobenzoate~ (component B) should be in an amount of not more than about 30% by weight based on th~ total a~ount of the compo~ition. When the amount is re than about 30% by weight, the resulting composition becomes narrower in the mesomorphic range than p-cyanophenyl-p'-n-alkylbanzoates (component A) alone and therefore, the ob~ect of this invention can not be attaine~.
Particularly, when the amount of the component B is within the range of about 10 to 25% by weight, compositions having broader mesomorphic range can be obtained.
In accordance with particularly, preferred embodiments of thi~ invention, there are provided Np-liquid crystal compositions having remarkably broad mesomorphic r~nge, ~hich consist of a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate as the component A and p-n-butylphenyl-p'-cyanobenzoate, p-n-hexylphenyl-p'-cyanobenzoate or p-n-octylphenyl-p'-cyanobenzoate as the component B in the amount as defined above.
The Np-liquid crystal cornpositions of this invention are chemically stable and have the mesomorphic range broader particularly, in a low temperature zone than that of p-cyanophenyl-p'-n-alkylbenzoates of the component A, and therefore, are useful for the TN-type display device.
This invention will be illustrated by the following non-limitative examples.
p-n-Alkylphenyl-p'-cyanobenzoates (component B) used in the examples were prepared in accordance with the process as described herein~efore.
Example 1 A Np-liquid crystal composition having a mesomorphic range of 34 to 49.0C was obtained by mixing 80% by weight of p-cyanophenyl-p'-n-hexylbenzoate (mesomorphic range :
48C) and 20% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, Np-liquid crystal compositions were obtained by mixing the components A and B as set forth in Table 3.
Mesomorphic ranges of these compositions are also in Table 3.
. ~ ~ ~
1049'~49 .C t~ o ~ o o ~ o o o In u~ o u~
~ .
~ . o~ 1 o~
t ~ ~ ~ ~ u~ u~
~ t~ ¢ ~ ~ ~ ~ ~
~: ~ ~ ~ ~ ~ ~ ~ ~r ~ ~ ~ ~
~ o o o o o o U~ o U~ o ~ o P N N t~l N N N _I ~I N
J~ . - .. .. .. .. .. .. ..
o o o o o o u~ o u~ o In o ~ ~ ~ co eo ~ ~ ~
. ~ ._ 2 ~: Q ~ ~ ~ ~
~ ~ ~ r~
~ - ~ - ~ - -'3 U ~ 5~ ~ ~ ~ U
: ~ u=ou=ocl~=o u=ou=o~=o ~l-~ l ~ ~ ~ ~ o~
,u,l ~b ,u" ~ ~ ~' ~ .
& -
3 ~ ~
~ . ~ ~ ~
1'~ ~u I ~,, I uou 1 1~ ~ N ~
~o49A~49 Example 2 A Np-liquid crystal composition having a me~omorphic, r~nge of 24 to 51C was obtained by mixing 1 part by weight I of p-cyanophenyl-p'-n-hexylbenzoatc and 2 parts by weight of p-cyanophenyl-p'-n-octylbenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Next, by mixing 80~ by weight of said composition and 20~ by welght of p-n-propylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a me~omorphic range of 14 to 54C was obtained.
S~milarly, Np-liquid crystal compositions were obtainea by mixing the components A and B as set forth in Table 4.
Mesomorphic ranges of these compositions are also given in Table 4.
:
..
-~049Z49 ' i ~ D .
O O O O O O O ' .. .. .. .. .. ..
o o ~ o o o ~ , ~o ' , : ~ ~
~q~ s~o ~=o o=o~ =o ~ o 1~ 1~ u ~u .~' . ~
a ~ ~,. '.
, Ii~ ~
~ "
~ a~ ~
1049Z~9 C)C~
,c ~4 ^
~ U~ ~ ~ ~ ~ ~ (D n O ~ u~ Lr) Lr~ Lr) o ~ ~ ~ ~
~ ~ ~ ~ ~ ~ ~ U~ ~
~:
o o o o o o o O N N N N N N N
+J rl .. .. .. .. .. .. ..
bO ~
rJ ~ O O O O O O O
a) co o~ o~) co oo co o~
~., N ~ ~ ~) ~ C,) C.) N ~) ' ,4 ~ ,~ ~ ~
O N N N N N N N
X ~ X ~ ~ X
~ C~
C) ~ l l l l l l l ~ O O O O O O O
a) l l l m ~ c~-o c~=o ~=o c~----o c~=o c~=o c =o ~ l l l r~ ~o~ ~ ~ ~ ~
~ 1 E~ C~ C~
O
C_) ~ Z Z Z Z Z Z Z
--1-- _ N
. ~ 4 _ O
N
Il) N
E-' ~4 . . N
.Y ~1 .. Il ~Z~ ~Z~ Z Z
_ ~) C,) ~1 l l ~ ~ ~ ~ [~
~4 O O
~ ~)=O C)=O O O
¢~H~ ~ 0~ ~ 0 ~0 ) ~ ~D
F. V~ N N ~. ~ ~
a) o ~C ~ (r~ N N N
1:: h C ) c~ N X :I~ N
O ~ ~ (~
~+~ . . _~
~ X
0-~
C~ ~ C~ ~ ~
Example 3 lO 49 2 4g A Np-liquid crystal composition having a mesomorphic range of 7 to 47.5C was obtained by mixing p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heatlng at about 100C and stirring (hereinafter referred to as Composition I). Next, by mixing 80% by weight of Composition I and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a mesomorphic range of -3 to 49.5C was obtained.
Also, a Np-liquid crystal composition having a meso-morphic range of 20 to 51.5C was obtained by mixing p-cyano-phenyl-p'-n-hexylbenzoate, p-cyanophenyl-p'-n-heptylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heating at about 100C and stirring (hereinafter referred to as Composition II). Then, by mixing 80% by weight of Composition II and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same manner as the above, a Np-liquid crystal composition having a meso-morphic range of 15 to 55.0C was obtained.
Table 5 shows mesomorphic ranges of Np-liquid crystal compositions obtained by mixing Compositions I or II
(component A) with one of p-n-alkylphenyl-p'-cyanobenzoates (component B).
Table 5 Component A ~
Mixtures of Component B Weight Mesomorphic p-cyanophenyl-p'-n-alkylbenzoates p-n-alkylphenyl-p'-cyanobenzoates Ratio Ranges, C
95 : 5 S~ ~7.5 90 : 10 3~-49.0 N--C ~ -C-O- ~ -(CH2)5.CH3 85 : lS 0~'~9.0 80 : 20 _3 ~ 49.5 75 : 25 -1~ S0.0 70 : 30 8~ 52.0 Composition I
_ _ _ (7- 47.5C NSC- ~ -ICI-O_ ~ -(CH2)2 3 80 : 20 2~ 51.5 N--C- ~ -ICl-O- ~ -(CH2)3.C 3 80 : 20 -1 49.5 N-C- ~ ~-ICi-n~ H2)6 3 80 : 20 2~ 52.0 7~C- $ -C-O- ~ -(C~2)7.Cl3 ~0 : 20~ 51.5 N=C- Q -C-0- ~ -(CH )5.CH 80 : 20 lS~ SS.0 Composition II 0 2 3 (20~ 51.5C) N-C- ~ -ICl-O- ~ -(CH2)6 3 80 : 20 lS~ 56.0 , N-C- ~ -Cl-0- ~ -(CH2 7 3 ao 20 _ ~_ .
_. .. ..
`
~049Z49 Example 4 A Np-liquid crystal composition having a mesomorphic range of 10 to 53C was obtained by mixing 80% by weight of the Composition II of Example 3, 10% by weight of p-n-propylphenyl-p'-cyanobenzoate and 10% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, nP-liquid crystal compositions were obtained by mixing the Composition II (component A) and two p-n-alkylphenyl-p'-cyanobenzoa-tes (component B) as set forth in Table 6. Mesomorphic ranges of these compositions are also set forth in Table 6.
~ O ~
~ ~ U~
~ a) ~ ? ~ ~
O bO o ~ o ~: ~ ~ ~ ~
o o o o Y o ~ C~
~ 4 .. .. .. ..
.~ ~ o o o o ~~ CO OD 0~ OD
3 (o ~_ N C~l C~l [~
~)=O C~=O C~--O
C~=O
Z; ~IZI 11 .ZI
1~ ~ (~ (~
O ~ ~ ;~
N C ) ~ ) . (o O c~ U') ~1 ,40 ~ ~ l (D ~ ~
~ -~, ~
~ o o ol ol m ~ c~=o c~=o ~o ~o ~_ Z' ~ U~
~ o U N H
¢ ~,q ~ ~) ~H ~ O O
~ O ~ +'' ~i ~ ;1~ U~
C~ ~ ~ C~ ~
~ . ~ ~ ~
1'~ ~u I ~,, I uou 1 1~ ~ N ~
~o49A~49 Example 2 A Np-liquid crystal composition having a me~omorphic, r~nge of 24 to 51C was obtained by mixing 1 part by weight I of p-cyanophenyl-p'-n-hexylbenzoatc and 2 parts by weight of p-cyanophenyl-p'-n-octylbenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Next, by mixing 80~ by weight of said composition and 20~ by welght of p-n-propylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a me~omorphic range of 14 to 54C was obtained.
S~milarly, Np-liquid crystal compositions were obtainea by mixing the components A and B as set forth in Table 4.
Mesomorphic ranges of these compositions are also given in Table 4.
:
..
-~049Z49 ' i ~ D .
O O O O O O O ' .. .. .. .. .. ..
o o ~ o o o ~ , ~o ' , : ~ ~
~q~ s~o ~=o o=o~ =o ~ o 1~ 1~ u ~u .~' . ~
a ~ ~,. '.
, Ii~ ~
~ "
~ a~ ~
1049Z~9 C)C~
,c ~4 ^
~ U~ ~ ~ ~ ~ ~ (D n O ~ u~ Lr) Lr~ Lr) o ~ ~ ~ ~
~ ~ ~ ~ ~ ~ ~ U~ ~
~:
o o o o o o o O N N N N N N N
+J rl .. .. .. .. .. .. ..
bO ~
rJ ~ O O O O O O O
a) co o~ o~) co oo co o~
~., N ~ ~ ~) ~ C,) C.) N ~) ' ,4 ~ ,~ ~ ~
O N N N N N N N
X ~ X ~ ~ X
~ C~
C) ~ l l l l l l l ~ O O O O O O O
a) l l l m ~ c~-o c~=o ~=o c~----o c~=o c~=o c =o ~ l l l r~ ~o~ ~ ~ ~ ~
~ 1 E~ C~ C~
O
C_) ~ Z Z Z Z Z Z Z
--1-- _ N
. ~ 4 _ O
N
Il) N
E-' ~4 . . N
.Y ~1 .. Il ~Z~ ~Z~ Z Z
_ ~) C,) ~1 l l ~ ~ ~ ~ [~
~4 O O
~ ~)=O C)=O O O
¢~H~ ~ 0~ ~ 0 ~0 ) ~ ~D
F. V~ N N ~. ~ ~
a) o ~C ~ (r~ N N N
1:: h C ) c~ N X :I~ N
O ~ ~ (~
~+~ . . _~
~ X
0-~
C~ ~ C~ ~ ~
Example 3 lO 49 2 4g A Np-liquid crystal composition having a mesomorphic range of 7 to 47.5C was obtained by mixing p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heatlng at about 100C and stirring (hereinafter referred to as Composition I). Next, by mixing 80% by weight of Composition I and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same way as the above, a Np-liquid crystal composition having a mesomorphic range of -3 to 49.5C was obtained.
Also, a Np-liquid crystal composition having a meso-morphic range of 20 to 51.5C was obtained by mixing p-cyano-phenyl-p'-n-hexylbenzoate, p-cyanophenyl-p'-n-heptylbenzoate and p-cyanophenyl-p'-n-octylbenzoate in equal parts by weight in a nitrogen atmosphere while heating at about 100C and stirring (hereinafter referred to as Composition II). Then, by mixing 80% by weight of Composition II and 20% by weight of p-n-hexylphenyl-p'-cyanobenzoate in the same manner as the above, a Np-liquid crystal composition having a meso-morphic range of 15 to 55.0C was obtained.
Table 5 shows mesomorphic ranges of Np-liquid crystal compositions obtained by mixing Compositions I or II
(component A) with one of p-n-alkylphenyl-p'-cyanobenzoates (component B).
Table 5 Component A ~
Mixtures of Component B Weight Mesomorphic p-cyanophenyl-p'-n-alkylbenzoates p-n-alkylphenyl-p'-cyanobenzoates Ratio Ranges, C
95 : 5 S~ ~7.5 90 : 10 3~-49.0 N--C ~ -C-O- ~ -(CH2)5.CH3 85 : lS 0~'~9.0 80 : 20 _3 ~ 49.5 75 : 25 -1~ S0.0 70 : 30 8~ 52.0 Composition I
_ _ _ (7- 47.5C NSC- ~ -ICI-O_ ~ -(CH2)2 3 80 : 20 2~ 51.5 N--C- ~ -ICl-O- ~ -(CH2)3.C 3 80 : 20 -1 49.5 N-C- ~ ~-ICi-n~ H2)6 3 80 : 20 2~ 52.0 7~C- $ -C-O- ~ -(C~2)7.Cl3 ~0 : 20~ 51.5 N=C- Q -C-0- ~ -(CH )5.CH 80 : 20 lS~ SS.0 Composition II 0 2 3 (20~ 51.5C) N-C- ~ -ICl-O- ~ -(CH2)6 3 80 : 20 lS~ 56.0 , N-C- ~ -Cl-0- ~ -(CH2 7 3 ao 20 _ ~_ .
_. .. ..
`
~049Z49 Example 4 A Np-liquid crystal composition having a mesomorphic range of 10 to 53C was obtained by mixing 80% by weight of the Composition II of Example 3, 10% by weight of p-n-propylphenyl-p'-cyanobenzoate and 10% by weight of p-n-butylphenyl-p'-cyanobenzoate in a nitrogen atmosphere while heating at about 100C and stirring.
Similarly, nP-liquid crystal compositions were obtained by mixing the Composition II (component A) and two p-n-alkylphenyl-p'-cyanobenzoa-tes (component B) as set forth in Table 6. Mesomorphic ranges of these compositions are also set forth in Table 6.
~ O ~
~ ~ U~
~ a) ~ ? ~ ~
O bO o ~ o ~: ~ ~ ~ ~
o o o o Y o ~ C~
~ 4 .. .. .. ..
.~ ~ o o o o ~~ CO OD 0~ OD
3 (o ~_ N C~l C~l [~
~)=O C~=O C~--O
C~=O
Z; ~IZI 11 .ZI
1~ ~ (~ (~
O ~ ~ ;~
N C ) ~ ) . (o O c~ U') ~1 ,40 ~ ~ l (D ~ ~
~ -~, ~
~ o o ol ol m ~ c~=o c~=o ~o ~o ~_ Z' ~ U~
~ o U N H
¢ ~,q ~ ~) ~H ~ O O
~ O ~ +'' ~i ~ ;1~ U~
C~ ~ ~ C~ ~
Claims (5)
1. Nematic liquid crystal compositions consisting essentially of (A) at least one of p-cyanophenyl-p'-n-alkylbenzoates represented by Formula I, I
wherein R1 is n-alkyl group of 4 to 8 carbon atoms and (B) at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by Formula II
II
wherein R2 is n-alkyl group of 3 to 8 carbon atoms, an amount of said component B being within the range of not more than about 30% by weight based on the total amount of the composition.
wherein R1 is n-alkyl group of 4 to 8 carbon atoms and (B) at least one of p-n-alkylphenyl-p'-cyanobenzoates represented by Formula II
II
wherein R2 is n-alkyl group of 3 to 8 carbon atoms, an amount of said component B being within the range of not more than about 30% by weight based on the total amount of the composition.
2. Nematic liquid crystal compositions of claim 1 wherein said amount of component B is within the range of about 10% to 25% by weight.
3. Nematic liquid crystal compositions of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-butylphenyl-p'-cyanobenzoate.
4. Nematic liquid crystal composition of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-hexylphenyl-p'-cyanobenzoate.
5. Nematic liquid crystal composition of claim 2 wherein said component A is a mixture in equal parts by weight of p-cyanophenyl-p'-n-butylbenzoate, p-cyanophenyl-p'-n-hexylbenzoate and p-cyanophenyl-p'-n-octylbenzoate and said component B is p-n-octylphenyl-p'-cyanobenzoate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50000665A JPS5177591A (en) | 1974-12-28 | 1974-12-28 | Nemachitsukuekishososeibutsu |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1049249A true CA1049249A (en) | 1979-02-27 |
Family
ID=11480018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA227,212A Expired CA1049249A (en) | 1974-12-28 | 1975-05-16 | Nematic liquid crystal compositions |
Country Status (8)
Country | Link |
---|---|
US (1) | US4014811A (en) |
JP (1) | JPS5177591A (en) |
AT (1) | AT346400B (en) |
CA (1) | CA1049249A (en) |
CH (1) | CH603782A5 (en) |
FR (1) | FR2296000A1 (en) |
GB (1) | GB1486055A (en) |
NL (1) | NL7506198A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4253740A (en) * | 1977-09-12 | 1981-03-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials and devices containing them |
US4427569A (en) | 1980-12-18 | 1984-01-24 | Hughes Aircraft Company | Short length ester liquid crystal mixtures and process for making same |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2024269A1 (en) * | 1970-05-19 | 1971-12-02 | Merck Patent Gmbh | Nematic mixtures - of low melting point, used in electronics |
US3923857A (en) * | 1972-02-23 | 1975-12-02 | Hoffmann La Roche | Liquid crystal esters |
BE795776A (en) * | 1972-02-23 | 1973-08-22 | Hoffmann La Roche | LIQUID CRYSTALLINE ESTERS |
JPS5229716B2 (en) * | 1972-06-07 | 1977-08-03 | ||
JPS562114B2 (en) * | 1972-07-13 | 1981-01-17 | ||
JPS5549100B2 (en) * | 1972-08-03 | 1980-12-10 | ||
GB1450713A (en) * | 1972-12-06 | 1976-09-29 | Suwa Seikosha Kk | Nematic liquid crystal material |
JPS4978683A (en) * | 1972-12-06 | 1974-07-29 | ||
US3891307A (en) * | 1973-03-20 | 1975-06-24 | Matsushita Electric Ind Co Ltd | Phase control of the voltages applied to opposite electrodes for a cholesteric to nematic phase transition display |
CH577178A5 (en) * | 1973-04-04 | 1976-06-30 | Hoffmann La Roche | |
US3975286A (en) * | 1974-09-03 | 1976-08-17 | Beckman Instruments, Inc. | Low voltage actuated field effect liquid crystals compositions and method of synthesis |
-
1974
- 1974-12-28 JP JP50000665A patent/JPS5177591A/en active Pending
-
1975
- 1975-05-16 CA CA227,212A patent/CA1049249A/en not_active Expired
- 1975-05-27 NL NL7506198A patent/NL7506198A/en not_active Application Discontinuation
- 1975-05-29 GB GB23497/75A patent/GB1486055A/en not_active Expired
- 1975-06-02 FR FR7517094A patent/FR2296000A1/en active Granted
- 1975-06-04 CH CH719675A patent/CH603782A5/xx not_active IP Right Cessation
- 1975-06-06 US US05/584,662 patent/US4014811A/en not_active Expired - Lifetime
- 1975-12-17 AT AT957475A patent/AT346400B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ATA957475A (en) | 1978-03-15 |
JPS5177591A (en) | 1976-07-05 |
FR2296000B1 (en) | 1977-12-02 |
GB1486055A (en) | 1977-09-14 |
CH603782A5 (en) | 1978-08-31 |
US4014811A (en) | 1977-03-29 |
FR2296000A1 (en) | 1976-07-23 |
DE2524004A1 (en) | 1976-07-08 |
NL7506198A (en) | 1976-06-30 |
AT346400B (en) | 1978-11-10 |
DE2524004B2 (en) | 1977-06-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4592858A (en) | Smectic liquid crystal compound and liquid crystal compositions | |
US4431853A (en) | Dicyclohexylethane derivatives | |
US4754051A (en) | Optically active tolan derivative | |
EP0044646B1 (en) | 4-(trans-4'-alkylcyclohexyl)benzoic acid 4"'-cyano-4"-biphenylyl esters and liquid crystal compositions containing them | |
US3981817A (en) | Mixtures of liquid crystals | |
CA1049249A (en) | Nematic liquid crystal compositions | |
JPS62209190A (en) | Liquid crystal composition | |
EP0171794B1 (en) | Alcohol derivatives and liquid crystal composition containing them | |
EP0056519B1 (en) | Short length ester liquid crystal mixtures | |
US4058475A (en) | Liquid crystal compositions containing cyanocinnamic acid esters | |
KR19990086177A (en) | Nematic liquid crystal composition and liquid crystal display device using the same | |
JP2782075B2 (en) | Optically active compound and liquid crystal composition containing the compound | |
US5069814A (en) | Benzoic acid derivative having a large positive dielectric anisotropy value | |
KR100544105B1 (en) | Nematic liquid crystal composition and liquid crystal display device using the same | |
EP0350510A1 (en) | Ferroelectric liquid crystal composition | |
JPS59141540A (en) | Tricyclic carboxylic acid ester derivative | |
JPS58126839A (en) | 4-(trans-4'-alkylcyclohexyl)benzoic acid 2,4-di-halogenophenyl ester | |
US4203862A (en) | Liquid crystal composition | |
JPH04124183A (en) | Optically active pantolactone derivative | |
JPS588054A (en) | Trans-4-(4'-substituted phenyl)-cyclohexanecarboxylic acid 4'''-cyanobiphenyl ester | |
JPS6136251A (en) | Ester derivative of 3-halogeno-4-cyanophenol | |
JPH05140042A (en) | Unsaturated esters | |
JPS61229870A (en) | Heterocyclic compound | |
JPH04103555A (en) | Cyclobutane derivative | |
JPH0142261B2 (en) |