CN101747905A - Liquid crystal compound and liquid crystal composition comprising same - Google Patents
Liquid crystal compound and liquid crystal composition comprising same Download PDFInfo
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- CN101747905A CN101747905A CN200810188104A CN200810188104A CN101747905A CN 101747905 A CN101747905 A CN 101747905A CN 200810188104 A CN200810188104 A CN 200810188104A CN 200810188104 A CN200810188104 A CN 200810188104A CN 101747905 A CN101747905 A CN 101747905A
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Abstract
The invention provides a liquid crystal compound, which has the following chemical formulas (I): wherein Y1, Y2 and Y3 are independently hydrogen, halogen, cyano or thiocyano; and R is C1 to C12 alkyl or C1 to C12 alkoxyl. The invention also provides a liquid crystal compound comprising same.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd, particularly relevant for a kind of piperazidine base (piperazinyl, liquid crystalline cpd piperazine) of containing.
Background technology
Liquid crystal has dielectric and optics anisotropy, possess good molecular orientation and flow characteristics simultaneously, when being subjected to external stimuluss such as light, heat, electric field or magnetic field, the orientation of molecule is easy to change, cause the correlated change of liquid crystal material light and shade or show other special electric optical effect, if make indicating meter, will have light weight, carry easily, the little advantage such as do not take up space of volume, and energy expenditure is lower.Therefore, in recent years, liquid crystal material becomes display media indispensable in various portable electronics and the information products, the indicating meter that not only is widely used in Die elektrische Zeituhr, counter and fascia, more be used in for example twisted nematic (TN, twisted nematic) and the display material of the ultrathin liquid-crystal display of super-twist nematic (STN, super twisted nematic).Other has all shown the general and importance of liquid crystal material on using as mobile computer, projector light gate assembly or duplicating machine storage element etc.
On chemical property, the ideal liquid crystal material should possess broad nematic liquid crystal phase scope, low melting point, low Heat of fusion, materialization stability and colourless.And on physical property, the ideal liquid crystal material then should possess high dielectric anisotropy (dielectric anisotropy, Δ ε) and high birefringence rate (birefringence, Δ n).
Summary of the invention
The object of the present invention is to provide the liquid crystalline cpd of a kind of high dielectric anisotropy, high birefringence rate and colourless, high photo and thermal stability and highly compatible.
One embodiment of the invention provide a kind of liquid crystalline cpd, have following chemical formula (I):
Wherein
Y1, Y2 and Y3 are hydrogen, halogen, cyano group or thiocyano independently; And R is C1～12 alkyl or C1～12 alkoxyl groups.
One embodiment of the invention provide a kind of liquid-crystal composition, comprising: one first liquid crystalline cpd has above-mentioned chemical formula (I); And one second liquid crystalline cpd, have following chemical formula (Z1)～(Z9):
R wherein
1Be C1～9 alkyl, B is halogen or cyano group, R
2, R
3With R
4Be C1～10 alkyl independently, wherein a methylene radical (methylene) is replaced by Sauerstoffatom or vinyl, and at least one hydrogen atom is replaced by fluorine atom, R
5With R
8Be C1～10 alkyl independently, wherein a methylene radical is replaced by Sauerstoffatom, R
6, R
7With R
9Be C1～10 alkyl independently, A1, A2, A3 and A5 are anti-form-1 independently, and the 4-cyclohexyl (trans-1,4-cyclohexylene) or 1, the 4-phenylene (1,4-phenylene), A4 is 1, the 4-phenylene, and wherein at least one hydrogen atom is replaced Z by fluorine atom
1Be ethylidene (ethylene) or ethynyl, m and n are 0～2, X
3Be hydrogen or fluorine, wherein the part by weight of this first liquid crystalline cpd and this second liquid crystalline cpd was between 0.5: 99.5～35: 65, and preferably, the part by weight of this first liquid crystalline cpd and this second liquid crystalline cpd was between 5: 95～10: 90.
The present invention utilizes the modification to the liquid crystal molecule chemical structure, to improve its chemical property and physics photoelectric characteristic, in order to being applied to various LCD assemblies.Liquid crystalline cpd of the present invention is characterised in that and imports a piperazinyl (piperazine) in its molecular structure, produces resonance so that electron pair to be provided, and increases dipole moment (dipolemoment), and by the polar functional base (Y in the structure
1, Y
2And Y
3) produce and draw electronic effect, and raising dielectric anisotropy (Δ ε), on the other hand, because the conjugated structure that increases on the molecule main shaft can improve the liquid crystal molecule degree of birefringence, therefore the present invention imports for example conjugated structure of phenyl ring and three key on the molecule main shaft of liquid crystalline cpd, to improve its degree of birefringence (Δ n).In addition, the terminal polar functional base of liquid crystalline cpd of the present invention (Y
1, Y
2And Y
3) be colourless halogen, cyano group or thiocyano, make unlikely interferoscope effect when importing these functional groups.When in addition the big dipole moment of the present invention, low viscous high dielectric anisotropic liquid crystal compound are applied to the dispensing liquid crystal of for example twisted nematic (TN), cholesteric (ChLC) or polyphosphazene polymer mould assembly (PDLC), also can reduce driving voltage.In sum, liquid crystalline cpd of the present invention also has the advantage of colourless, high photo and thermal stability and highly compatible except that can reaching high dielectric anisotropy and high birefringence rate.
For above-mentioned purpose of the present invention, feature and advantage can be become apparent, a preferred embodiment cited below particularly is described in detail below:
Embodiment
One embodiment of the invention provide a kind of liquid crystalline cpd, have following chemical formula (I):
In the chemical formula (I), Y1, Y2 and Y3 can be hydrogen, halogen, cyano group or thiocyano independently.R can be C1～12 alkyl, C1～12 alkoxyl groups or C3～6 alkyl.
It should be noted that above-mentioned liquid crystalline cpd is colourless.
Below enumerate the particular instance of liquid crystalline cpd of the present invention:
The dielectric anisotropy of liquid crystalline cpd of the present invention (Δ ε) is between 18～35, degree of birefringence (Δ n) is between 0.25～0.40, and it can be widely used in reflective cholesteric type liquid-crystal display, polymer dispersion type liquid crystal indicating meter, TN, STN, TFT or IPS liquid-crystal display.
The present invention utilizes the modification to the liquid crystal molecule chemical structure, to improve its chemical property and physics photoelectric characteristic, in order to being applied to various LCD assemblies.Liquid crystalline cpd of the present invention is characterised in that and imports a piperazinyl in its molecular structure, produces resonance so that electron pair to be provided, and increases dipole moment, and by the polar functional base (Y in the structure
1, Y
2And Y
3) produce and draw electronic effect, and raising dielectric anisotropy (Δ ε), on the other hand, because the conjugated structure that increases on the molecule main shaft can improve the liquid crystal molecule degree of birefringence, therefore the present invention imports for example conjugated structure of phenyl ring and three key on the molecule main shaft of liquid crystalline cpd, to improve its degree of birefringence (Δ n).In addition, the terminal polar functional base of liquid crystalline cpd of the present invention (Y
1, Y
2And Y
3) be colourless halogen, cyano group or thiocyano, make unlikely interferoscope effect when importing these functional groups.When in addition the big dipole moment of the present invention, low viscous high dielectric anisotropic liquid crystal compound are applied to the dispensing liquid crystal of for example twisted nematic (TN), cholesteric (ChLC) or polyphosphazene polymer mould assembly (PDLC), also can reduce driving voltage.In sum, liquid crystalline cpd of the present invention also has the advantage of colourless, high photo and thermal stability and highly compatible except that can reaching high dielectric anisotropy and high birefringence rate.
One embodiment of the invention provide a kind of liquid-crystal composition, comprise one first liquid crystalline cpd, have above-mentioned chemical formula (I), and one second liquid crystalline cpd, have following chemical formula (Z1)～(Z9):
In the chemical formula (Z1)～(Z9), R
1Can be C1～9 alkyl.B can be halogen or cyano group.R
2, R
3With R
4Can be C1～10 alkyl independently, wherein a methylene radical can be Sauerstoffatom or vinyl replaces, and at least one hydrogen atom can be fluorine atom and replaces.R
5With R
8Can be C1～10 alkyl independently, wherein a methylene radical can be Sauerstoffatom and replaces.R
6, R
7With R
9Can be C1～10 alkyl independently.A1, A2, A3 and A5 can be anti-form-1 independently, 4-cyclohexyl or 1,4-phenylene.A4 can be 1, the 4-phenylene, and wherein at least one hydrogen atom can be fluorine atom and replaces.Z
1Can be ethylidene or ethynyl.M and n can be 0～2.X
3Can be hydrogen or fluorine.
The part by weight of above-mentioned first liquid crystalline cpd and second liquid crystalline cpd was between 0.5: 99.5～35: 65, and preferably, the part by weight of this first liquid crystalline cpd and this second liquid crystalline cpd was between 5: 95～10: 90.
[embodiment 1] Formula I-1 synthetic and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
Synthesis step:
(1) at first, under nitrogen environment, the compd A of 1 gram (6.2mmol), the bromination pentane of 0.9 gram (6mmol) and the salt of wormwood of 1.38 grams (10mmol) are placed reaction flask, and add 20 milliliters DMSO (dimethyl sulfoxide), be heated to 100～110 ℃, refluxed 16 hours.After cooling, repeatedly remove fully to DMSO with saturated aqueous common salt and ethyl acetate extraction.Treat with after dried over mgso and concentrated the draining, with the column chromatography purification crude product, to obtain weak yellow liquid product M1, productive rate 90%.
(2) at first, under nitrogen environment, the compound M1 of 1 gram (4.2mmol) and the n-bromo-succinimide (NBS) of 1.38 grams (10mmol) are placed reaction flask, and add 10 milliliters methylene dichloride, reaction is 16 hours under room temperature.Afterwards, repeatedly with saturated aqueous common salt and ethyl acetate extraction.Treat with after dried over mgso and concentrated the draining, with the column chromatography purification crude product, to obtain weak yellow liquid product M2, productive rate 90%.
(3) at first, under nitrogen environment, the 1 ethynyl trimethyl silane (ethynyltrimethylsilane) that restrains (10.2mmol) is placed reaction flask, and add 10 milliliters THF, be cooled to-78 ℃ with Dewar basin, liquid nitrogen and acetone.Afterwards, the n-BuLi that adds 12 milliliters reacted 20 minutes.Then, the zinc chloride that 2.4 grams (18.3mmol) is dissolved in THF adds in the reaction flask, in keeping under the low-temperature condition sustained reaction 20 minutes.After waiting to get back to 0 ℃, four (triphenylphosphines) of the compound M2 of 2.1 grams (10.2mmol) and 0.3 gram (0.3mmol) are closed palladium (Tetrakis (triphenylphosphine) palladium) be dissolved in respectively in the THF adding reaction flask, in 60 ℃ of back flow reaction 12 hours.With NH
4The Cl stopped reaction.Afterwards, repeatedly with saturated aqueous common salt and ethyl acetate extraction.Treat with after dried over mgso and concentrated the draining, with the column chromatography purification crude product, to obtain faint yellow solid product M3, productive rate 70%.
(4) at first, under nitrogen environment, the 1 compound M3 that restrains (3mmol) is placed reaction flask, and add 10 milliliters the ethanol/methylene (volume ratio is 1/1) and the salt of wormwood of 0.4 gram (4.5mmol), reaction is 12 hours under room temperature.Afterwards, add 20 milliliters dichloromethane extraction repeatedly.Treat with after dried over mgso and concentrated the draining, with the column chromatography purification crude product, to obtain faint yellow solid product M4, productive rate 75%.
(5) at first, under nitrogen environment, the 1 compound M4 that restrains (3.9mmol) is placed reaction flask, and add 5 milliliters THF, be cooled to-78 ℃ with Dewar basin, liquid nitrogen and acetone.Afterwards, the n-BuLi that adds 1.7 milliliters reacted 20 minutes.Then, the zinc chloride that 0.9 gram (7mmol) is dissolved in THF adds in the reaction flask, in keeping under the low-temperature condition sustained reaction 20 minutes.After waiting to get back to 0 ℃, four (triphenylphosphines) of the 4-bromo-2-fluorobenzene first cyanogen (4-bromo-2-fluorobenzonitrile) of 0.8 gram (3.9mmol) and 0.2 gram (0.2mmol) are closed palladium be dissolved in THF respectively and add in the reaction flask, in 60 ℃ of back flow reaction 12 hours.With NH
4The Cl stopped reaction.Afterwards, repeatedly with saturated aqueous common salt and ethyl acetate extraction.Treat with after dried over mgso and concentrated the draining, with the column chromatography purification crude product, to obtain white solid product I-1, productive rate 65%.The dielectric anisotropy of Compound I-1 (Δ ε) is 31.8, and degree of birefringence (Δ n) is 0.3763.
The preparation method of The compounds of this invention I-2 and I-3 and Compound I-1 is similar, and only slightly different in the reactant of step (5), those of ordinary skills all can be according to embodiment 1 smooth synthetic compound I-2 and I-3.The dielectric anisotropy of Compound I-2 (Δ ε) is 26.9, and degree of birefringence (Δ n) is 0.3206.The dielectric anisotropy of Compound I-3 (Δ ε) is 18.8, and degree of birefringence (Δ n) is 0.2685.Table 1 is that The compounds of this invention I-1～I-3 and known class are like the comparison of its dielectric anisotropy of structure liquid crystal molecule (Δ ε) with degree of birefringence (Δ n).
Table 1
Table 1 can be found out, because the relative position of the more known liquid crystal molecule of Compound I of the present invention-1～I-3 in structure imported one more and had the piperazine group that unshared electron pair can produce resonance effect, increased integrally-built dipole moment, therefore Compound I-1～I-3 obviously has higher dielectric anisotropy (Δ ε), in addition, because the present invention imports one three keys in addition in structure, increased the conjugated structure on the molecule main shaft relatively, so, make the degree of birefringence (Δ n) of Compound I-1～I-3 also apparently higher than known liquid crystal molecule.
[embodiment 2] liquid-crystal compositions of the present invention (1) preparation and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
Compound I-1 and the liquid crystal compound of numbering YY066-042 are made a liquid-crystal composition with 5: 95 mixed of weight ratio.
The YY066-042 liquid crystal compound comprises 8% 5HBBCN, 24.1% 5HBCN, 7.7% 5HBCOOBFCN, 13.5% 5HBF, 7% 2HCOOBFCN, 6.5% 3HHCOOBF, 3.5% 5HHCOOBF, 1.7% 2BBCN, 4.9% 3HCOOBBCN, 15.4% 5BCOOBFCN and 7.7% 3HBCOOBFCN, its dielectric anisotropy (Δ ε) is 17.3, degree of birefringence (Δ n) is 0.1355, and the assembly driving voltage is 1.043V.In the liquid crystal compound of above-mentioned numbering YY066-042, each constituent is all with different code names combination expressions, and the pairing chemical formula of each code name is as follows: code name 2 is C
2H
5-, code name 3 is C
3H
7-, code name 5 is C
5H
11-, code name H is
Code name B is
Code name CN is-CN that code name COO is-COO-that code name F is-F.
After adding Compound I-1, the dielectric anisotropy of this liquid-crystal composition (Δ ε) rises to 18.1, and degree of birefringence (Δ n) rises to 0.1475, and the assembly driving voltage drops to 1.023V.
[embodiment 3] liquid-crystal compositions of the present invention (2) preparation and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
Compound I-2 and the liquid crystal compound of numbering DH0381-110 are made a liquid-crystal composition with 5: 95 mixed of weight ratio.
The DH0381-110 liquid crystal compound comprises 10.3% 5HBBCN, 7.2% 3HBO2,12.6% 2BBCN, 31.9% 5BBCN, 10% 3HEBBCN, 21.8% 7BBCN and 6.2% 5BEBBCN, its dielectric anisotropy (Δ ε) is 13.49, degree of birefringence (Δ n) is 0.0987, and the assembly driving voltage is 1.862.In the liquid crystal compound of above-mentioned numbering DH0381-110, each constituent is all with different code names combination expressions, and the pairing chemical formula of each code name is as follows: code name 2 is C
2H
5-, code name 3 is C
3H
7-, code name 5 is C
5H
11-, code name 7 is C
7H
15-, code name H is
Code name B is
Code name CN is-CN that code name F is-F that code name O is-O-that code name E is-COO-.
After adding Compound I-2, the dielectric anisotropy of this liquid-crystal composition (Δ ε) rises to 14.27, and degree of birefringence (Δ n) rises to 0.1112, and the assembly driving voltage drops to 1.434V.
[embodiment 4] liquid-crystal compositions of the present invention (3) preparation and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
Compound I-3 and the liquid crystal compound of numbering LOT3 are made a liquid-crystal composition with 10: 90 mixed of weight ratio.The LOT3 liquid crystal compound comprises 2.5% 5HBF, 2.5% 6HBF, 2.5% 7HBF, 9.6% 3HHB (F) F, 2.5% 3HBEB (FF) F, 2% 4HBEB (FF) F, 6.2% 3HHEB (FF) F, 4.9% 3HHB (FF) F, 9.6% 3HBB (FF) F, 9.7% 5HBB (FF) F, 5.2% 4HHB (FF) F, 4.5% 5HHB (FF) F, 9.9% 3HHV, 4.7% 3HBB (F) F, 9.8% 3HH2B (F) F, 9.1% 1BHHV and 4.8% 2BB (F) B3, its dielectric anisotropy (Δ ε) is 7.38, degree of birefringence (Δ n) is 0.0987, and the assembly driving voltage is 1.862.In the liquid crystal compound of above-mentioned numbering LOT3, each constituent is all with different code names combination expressions, and the pairing chemical formula of each code name is as follows: code name 1 is CH
3-, code name 3 is C
3H
7-, code name 4 is C
4H
9-, code name 5 is C
5H
11-, code name 6 is C
6H
13-, code name 7 is C
7H
15-, code name H is
Code name B is
B (F) is
B (FF) is
Code name F is-F that code name E is-COO-that code name V is CH
2=CH-.
After adding Compound I-3, the dielectric anisotropy of this liquid-crystal composition (Δ ε) rises to 8.545, and degree of birefringence (Δ n) rises to 0.1158, and the assembly driving voltage drops to 1.802V.
Claims (13)
1. liquid crystalline cpd has following chemical formula (I):
Wherein
Y1, Y2 and Y3 are hydrogen, halogen, cyano group or thiocyano independently; And
R is C1～12 alkyl or C1～12 alkoxyl groups.
2. liquid crystalline cpd according to claim 1, wherein R is C3～6 alkyl.
3. liquid crystalline cpd according to claim 1, wherein Y1 is that fluorine, Y2 are that cyano group, Y3 are fluorine.
4. liquid crystalline cpd according to claim 3, wherein R is C3～6 alkyl.
5. liquid crystalline cpd according to claim 1, wherein Y1 is that hydrogen, Y2 are that cyano group, Y3 are fluorine.
6. liquid crystalline cpd according to claim 5, wherein R is C3～6 alkyl.
7. liquid crystalline cpd according to claim 1, wherein Y1 is that hydrogen, Y2 are that cyano group, Y3 are hydrogen.
8. liquid crystalline cpd according to claim 7, wherein R is C3～6 alkyl.
9. liquid crystalline cpd according to claim 1, wherein Y1 is that fluorine, Y2 are that fluorine, Y3 are fluorine.
10. liquid crystalline cpd according to claim 9, wherein R is C3～6 alkyl.
11. liquid crystalline cpd according to claim 1, wherein said liquid crystalline cpd are colourless.
12. a liquid-crystal composition comprises:
One first liquid crystalline cpd has chemical formula as claimed in claim 1 (I); And
One second liquid crystalline cpd has following chemical formula (Z1)～(Z9):
R wherein
1Be C1～9 alkyl, B is halogen or cyano group, R
2, R
3With R
4Be C1～10 alkyl independently, wherein a methylene radical is replaced by Sauerstoffatom or vinyl, and at least one hydrogen atom is replaced by fluorine atom, R
5With R
8Be C1～10 alkyl independently, wherein a methylene radical is replaced by Sauerstoffatom, R
6, R
7With R
9Be C1～10 alkyl independently, A1, A2, A3 and A5 are anti-form-1 independently, 4-cyclohexyl or 1, and 4-phenylene, A4 are 1, the 4-phenylene, wherein at least one hydrogen atom is replaced Z by fluorine atom
1Be ethylidene or ethynyl, m and n are 0～2, X
3Be hydrogen or fluorine, the part by weight of wherein said first liquid crystalline cpd and described second liquid crystalline cpd was between 0.5: 99.5～35: 65.
13. liquid-crystal composition according to claim 12, the part by weight of wherein said first liquid crystalline cpd and described second liquid crystalline cpd was between 5: 95～10: 90.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106967443A (en) * | 2017-04-28 | 2017-07-21 | 烟台德润液晶材料有限公司 | The preparation method of alkyl cyclohexyl biphenyl nitrile liquid-crystal compounds |
| CN111944539A (en) * | 2020-07-31 | 2020-11-17 | 西安瑞联新材料股份有限公司 | Fluropiperazine-based benzoxazole liquid crystal compound and preparation method thereof |
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| DE4234627A1 (en) * | 1992-10-14 | 1994-04-21 | Merck Patent Gmbh | New 3-fluorophenyl-piperidine and -piperazine and precursor cpds. - used in liq. crystal medium, esp. for electro-optical display |
| US5314640A (en) * | 1989-11-29 | 1994-05-24 | Seiko Epson Corporation | Tolan derivatives, liquid crystal compositions including same, liquid crystal display devices including the compositions and method of preparation |
| US5356557A (en) * | 1991-03-13 | 1994-10-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Electrooptical system |
| JP2000336365A (en) * | 1999-06-01 | 2000-12-05 | Dainippon Ink & Chem Inc | Liquid crystal composition and liquid crystal display device |
| US20080135803A1 (en) * | 2006-12-06 | 2008-06-12 | Industrial Technology Research Institute Daily Polymer Corporation | High dielectric anisotropy liquid crystal compound and composition containing the same |
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2008
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| JPS57206673A (en) * | 1981-06-10 | 1982-12-18 | Matsushita Electric Ind Co Ltd | Piperazine phenyl ester derivative and liquid crystal composition |
| US5314640A (en) * | 1989-11-29 | 1994-05-24 | Seiko Epson Corporation | Tolan derivatives, liquid crystal compositions including same, liquid crystal display devices including the compositions and method of preparation |
| US5356557A (en) * | 1991-03-13 | 1994-10-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Electrooptical system |
| DE4234627A1 (en) * | 1992-10-14 | 1994-04-21 | Merck Patent Gmbh | New 3-fluorophenyl-piperidine and -piperazine and precursor cpds. - used in liq. crystal medium, esp. for electro-optical display |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106967443A (en) * | 2017-04-28 | 2017-07-21 | 烟台德润液晶材料有限公司 | The preparation method of alkyl cyclohexyl biphenyl nitrile liquid-crystal compounds |
| CN111944539A (en) * | 2020-07-31 | 2020-11-17 | 西安瑞联新材料股份有限公司 | Fluropiperazine-based benzoxazole liquid crystal compound and preparation method thereof |
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