CN101747905B - 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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- CN101747905B CN101747905B CN200810188104.4A CN200810188104A CN101747905B CN 101747905 B CN101747905 B CN 101747905B CN 200810188104 A CN200810188104 A CN 200810188104A CN 101747905 B CN101747905 B CN 101747905B
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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 subject to the external stimuluss such as light, heat, electric field or magnetic field, the orientation of molecule is easy to change, cause the change of liquid crystal material comparison of light and shade or show other special electric optical effect, if make indicating meter, will have quality gently, easily carry, 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 information products, not only the indicating meter that 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 super-twist nematic (STN, super twisted nematic) Ultrathin LCD.Other has all shown the general and importance of liquid crystal material in application as mobile computer, projector light gate assembly or duplicating machine storage element etc.
In chemical property, desirable liquid crystal material should possess broad Nematic liquid crystalline phase scope, low melting point, low Heat of fusion, materialization stability and colourless.And in physical property, desirable liquid crystal material 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 group.
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, there is following chemical formula (Z1)～(Z9):
R wherein
1for 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, 4-cyclohexyl (trans-1,4-cyclohexylene) or 1,4-phenylene (Isosorbide-5-Nitrae-phenylene), A4 is 1,4-phenylene, wherein at least one hydrogen atom is replaced by fluorine atom, Z
1for ethylidene (ethylene) or ethynyl, m and n are 0～2, X
3for 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 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 in its molecular structure and imports a piperazinyl (piperazine), to provide electron pair to produce resonance, increases dipole moment (dipolemoment), and by the polar functional base (Y in 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 increasing on molecule main shaft can improve 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 liquid crystalline cpd end polar functional base (Y of the present invention,
1, Y
2and Y
3) be colourless halogen, cyano group or thiocyano, unlikely interferoscope effect while making to import these functional groups.When the another large 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, except reaching high dielectric anisotropy and high birefringence rate, also has advantages of colourless, high photo and thermal stability and highly compatible.
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 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 group 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 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 in its molecular structure and imports a piperazinyl, to provide electron pair to produce resonance, increases dipole moment, and by the polar functional base (Y in 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 increasing on molecule main shaft can improve 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 liquid crystalline cpd end polar functional base (Y of the present invention,
1, Y
2and Y
3) be colourless halogen, cyano group or thiocyano, unlikely interferoscope effect while making to import these functional groups.When the another large 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, except reaching high dielectric anisotropy and high birefringence rate, also has advantages of colourless, high photo and thermal stability and highly compatible.
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 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 Isosorbide-5-Nitrae-phenylene.A4 can be Isosorbide-5-Nitrae-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 the first liquid crystalline cpd and the 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.
Synthesize and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n) [embodiment 1] Formula I-1
Synthesis step:
(1) first, under nitrogen environment, the salt of wormwood of the bromination pentane of the compd A of 1 gram (6.2mmol), 0.9 gram (6mmol) and 1.38 grams (10mmol) is placed in to reaction flask, and add the DMSO (dimethyl sulfoxide) of 20 milliliters, be heated to 100～110 ℃, reflux 16 hours.After cooling, with the extraction of saturated aqueous common salt and ethyl acetate, repeatedly remove completely to DMSO.After with dried over mgso concentrated draining, with column chromatography purification crude product, to obtain weak yellow liquid product M1, productive rate 90%.
(2) first, under nitrogen environment, the n-bromo-succinimide (NBS) of the compound M1 of 1 gram (4.2mmol) and 1.38 grams (10mmol) is placed in to reaction flask, and adds the methylene dichloride of 10 milliliters, under room temperature, react 16 hours.Afterwards, with saturated aqueous common salt and ethyl acetate, extract repeatedly.After with dried over mgso concentrated draining, with column chromatography purification crude product, to obtain weak yellow liquid product M2, productive rate 90%.
(3) first, under nitrogen environment, the ethynyl trimethyl silane (ethynyltrimethylsilane) of 1 gram (10.2mmol) is placed in to reaction flask, and adds the THF of 10 milliliters, with Dewar basin, liquid nitrogen and acetone, be cooled to-78 ℃.Afterwards, add the n-BuLi of 12 milliliters to react 20 minutes.Then, the zinc chloride that 2.4 grams (18.3mmol) are dissolved in to THF adds in reaction flask, in maintaining under low-temperature condition sustained reaction 20 minutes.After getting back to 0 ℃, four (triphenylphosphines) of the compound M2 of 2.1 grams (10.2mmol) and 0.3 gram (0.3mmol) are closed to palladium (Tetrakis (triphenylphosphine) palladium) and be dissolved in respectively THF and add in reaction flask, in 60 ℃ of back flow reaction 12 hours.With NH
4cl stopped reaction.Afterwards, with saturated aqueous common salt and ethyl acetate, extract repeatedly.After with dried over mgso concentrated draining, with column chromatography purification crude product, to obtain faint yellow solid product M3, productive rate 70%.
(4) first, under nitrogen environment, the compound M3 of 1 gram (3mmol) is placed in to reaction flask, and adds the ethanol/methylene (volume ratio is 1/1) of 10 milliliters and the salt of wormwood of 0.4 gram (4.5mmol), under room temperature, react 12 hours.Afterwards, add 20 milliliters dichloromethane extraction repeatedly.After with dried over mgso concentrated draining, with column chromatography purification crude product, to obtain faint yellow solid product M4, productive rate 75%.
(5) first, under nitrogen environment, the compound M4 of 1 gram (3.9mmol) is placed in to reaction flask, and adds the THF of 5 milliliters, with Dewar basin, liquid nitrogen and acetone, be cooled to-78 ℃.Afterwards, add the n-BuLi of 1.7 milliliters to react 20 minutes.Then, the zinc chloride that 0.9 gram (7mmol) is dissolved in to THF adds in reaction flask, in maintaining under low-temperature condition sustained reaction 20 minutes.After getting back to 0 ℃, four (triphenylphosphines) of the bromo-2-fluorobenzene of the 4-of 0.8 gram (3.9mmol) first cyanogen (4-bromo-2-fluorobenzonitrile) and 0.2 gram (0.2mmol) are closed to palladium and be dissolved in respectively THF and add in reaction flask, in 60 ℃ of back flow reaction 12 hours.With NH
4cl stopped reaction.Afterwards, with saturated aqueous common salt and ethyl acetate, extract repeatedly.After with dried over mgso concentrated draining, with 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.
Preparation method and Compound I-1 of the compounds of this invention I-2 and I-3 are similar, and only slightly different in the reactant of step (5), those of ordinary skills all can be according to the smooth synthetic compound I-2 of embodiment 1 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 the compounds of this invention I-1～I-3 and known class comparison with degree of birefringence (Δ n) like its dielectric anisotropy of structure liquid crystal molecule (Δ ε).
Table 1
Table 1 can be found out, because having imported one more, the relative position of the more known liquid crystal molecule of Compound I-1～I-3 of the present invention in structure there is 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, due to the present invention's another one three keys that import in structure, relatively increased the conjugated structure on molecule main shaft, 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)
By Compound I-1 with numbering YY066-042 liquid crystal compound with weight ratio ratio mixing manufacture one liquid-crystal composition of 5: 95.
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 Component driver 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 corresponding 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 Component driver voltage drop is 1.023V.
[embodiment 3] liquid-crystal compositions of the present invention (2) preparation and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
By Compound I-2 with numbering DH0381-110 liquid crystal compound with weight ratio ratio mixing manufacture one liquid-crystal composition of 5: 95.
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 Component driver 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 corresponding 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 Component driver voltage drop is 1.434V.
[embodiment 4] liquid-crystal compositions of the present invention (3) preparation and dielectric anisotropy (Δ ε) and degree of birefringence (Δ n)
By Compound I-3 with numbering LOT3 liquid crystal compound with weight ratio ratio mixing manufacture one liquid-crystal composition of 10: 90.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, Component driver 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 corresponding 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 Component driver voltage drop is 1.802V.
Claims (5)
1. a liquid crystalline cpd, has following chemical formula (I):
Wherein
Y
1for fluorine, Y
2for cyano group, Y
3for fluorine; Or
Y
1for hydrogen, Y
2for cyano group, Y
3for fluorine; Or
Y
1for hydrogen, Y
2for cyano group, Y
3for hydrogen; Or
Y
1for fluorine, Y
2for fluorine, Y
3for fluorine; And
R is C1～12 alkyl or C1～12 alkoxyl group.
2. liquid crystalline cpd according to claim 1, wherein R is C3～6 alkyl.
3. liquid crystalline cpd according to claim 1, wherein said liquid crystalline cpd is colourless.
4.. a liquid-crystal composition, comprising:
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)～(Z5):
R wherein
1for C1～9 alkyl, B is halogen or cyano group,
The part by weight of wherein said the first liquid crystalline cpd and described the second liquid crystalline cpd is between 0.5:99.5～35:65.
5. liquid-crystal composition according to claim 4, the part by weight of wherein said the first liquid crystalline cpd and described the second liquid crystalline cpd is between 5:95～10:90.
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| 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 |
| CN111944539B (en) * | 2020-07-31 | 2021-12-07 | 西安瑞联新材料股份有限公司 | Fluropiperazine-based benzoxazole liquid crystal compound and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57206673A (en) * | 1981-06-10 | 1982-12-18 | Matsushita Electric Ind Co Ltd | Piperazine phenyl ester derivative and liquid crystal composition |
| US7622056B2 (en) * | 2006-12-06 | 2009-11-24 | Industrial Technology Research Institute | High dielectric anisotropy liquid crystal compound and composition containing the same |
-
2008
- 2008-12-12 CN CN200810188104.4A patent/CN101747905B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2000336365A (en) * | 1999-06-01 | 2000-12-05 | Dainippon Ink & Chem Inc | Liquid crystal composition and liquid crystal display device |
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