CN102994100B - Liquid crystal composition and liquid crystal display device containing liquid crystal composition - Google Patents
Liquid crystal composition and liquid crystal display device containing liquid crystal composition Download PDFInfo
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- CN102994100B CN102994100B CN201210383024.0A CN201210383024A CN102994100B CN 102994100 B CN102994100 B CN 102994100B CN 201210383024 A CN201210383024 A CN 201210383024A CN 102994100 B CN102994100 B CN 102994100B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 123
- 239000000203 mixture Substances 0.000 title claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 12
- 230000004044 response Effects 0.000 abstract description 12
- 238000012360 testing method Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BAWRBXGQZOIZMJ-UHFFFAOYSA-M [Cl-].FC(F)=C(F)[Zn+] Chemical compound [Cl-].FC(F)=C(F)[Zn+] BAWRBXGQZOIZMJ-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 0 *C(C1)CC(C=C2)=C1C[C@@]2C(F)=C(c1ccc(*)cc1)F Chemical compound *C(C1)CC(C=C2)=C1C[C@@]2C(F)=C(c1ccc(*)cc1)F 0.000 description 2
- YEJCHVFCLNKZPU-UHFFFAOYSA-N CC1COC(C)CC1 Chemical compound CC1COC(C)CC1 YEJCHVFCLNKZPU-UHFFFAOYSA-N 0.000 description 2
- LPTXCFDZFRYMLY-UHFFFAOYSA-N Cc1cnc(C)c(F)c1 Chemical compound Cc1cnc(C)c(F)c1 LPTXCFDZFRYMLY-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N Cc1cnc(C)cc1 Chemical compound Cc1cnc(C)cc1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004537 pulping Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 1
- GGAUOFGZWZKYSP-UHFFFAOYSA-N CC(C)(CC=C1C)C=C1F Chemical compound CC(C)(CC=C1C)C=C1F GGAUOFGZWZKYSP-UHFFFAOYSA-N 0.000 description 1
- LDCFEAFMWBVWHO-UHFFFAOYSA-N CC1(CC2)CCC2(C)CC1 Chemical compound CC1(CC2)CCC2(C)CC1 LDCFEAFMWBVWHO-UHFFFAOYSA-N 0.000 description 1
- CROKKJCBPVRHHF-UHFFFAOYSA-N CC1CC(F)=C(C)CC1 Chemical compound CC1CC(F)=C(C)CC1 CROKKJCBPVRHHF-UHFFFAOYSA-N 0.000 description 1
- KMGDYKOGDOVDCW-UHFFFAOYSA-N CC1CC=C(C)CC1 Chemical compound CC1CC=C(C)CC1 KMGDYKOGDOVDCW-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- NRYJYCZRGKAYMG-UHFFFAOYSA-N CC1OCC(C)=CC1 Chemical compound CC1OCC(C)=CC1 NRYJYCZRGKAYMG-UHFFFAOYSA-N 0.000 description 1
- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 1
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- SPIOKNPWOZFWDI-UHFFFAOYSA-N fluorobenzene;lithium Chemical compound [Li].FC1=CC=CC=C1 SPIOKNPWOZFWDI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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- Liquid Crystal Substances (AREA)
Abstract
The invention provides a liquid crystal composition and application thereof. The liquid crystal composition comprises the following components in percentage by weight: 1 to 35 percent of a compound with the general formula (I), 1 to 50 percent of a compound with the general formula (II), 30 to 75 percent of a compound with the general formula (III), and 0 to 30 percent of a compound with the general formula (IV). The liquid crystal composition can be used in a liquid crystal element, and has the performances of high response speed and excellent power-saving property and properly high optical anisotropy.
Description
Technical Field
The present invention relates to a liquid crystal composition, and more particularly, to a liquid crystal composition having a fast response speed, excellent power saving performance, and a suitably high optical anisotropy, and an application thereof.
Background
Liquid crystal display devices are classified into types such as PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), and the like, according to a display mode of a liquid crystal. The driving method of the element is classified into a PM (passive matrix) type and an AM (active matrix) type. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into a TFT (thin film transistor), an MIM (metal insulator metal), and the like. The types of TFTs are amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to a manufacturing process. Liquid crystal display elements are classified into a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both light sources of natural light and backlight, depending on the type of light source.
The most common of these effects are the TN effect, the STN effect and the SBE (super twisted birefringence) effect. In both these and similar electro-optical effects, liquid crystal media of positive dielectric anisotropy are used. In addition to the mentioned electro-optical effects using liquid-crystalline media of positive dielectric anisotropy, there are also other electro-optical effects which make use of liquid-crystalline media of negative dielectric anisotropy, such as the ECB (electrically controlled birefringence) effect and its sub-form DAP (phase alignment deformation) effect, the VAN effect and the CSH (color super homeotropic) effect.
Liquid crystal materials must have good chemical and thermal stability, appropriate optical anisotropy, a broad nematic phase range, and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid crystal material should have a low viscosity and produce a low threshold voltage and a high contrast within the liquid crystal cell. Since liquid crystal materials are usually used as mixtures of a plurality of components, it is particularly important that these components are miscible with one another. However, since the optimization of the performance parameters of the hybrid liquid crystal material is contradictory, restrictive and influenced, it is difficult to obtain a wide nematic phase range, appropriate refractive index anisotropy and dielectric anisotropy, and low-temperature storage stability. In liquid crystal compositions as described in EP0667555, EP0673986, DE19528106, DE19528107, WO962851, significant disadvantages are a longer response time, a lower resistivity and an excessively high operating voltage. In addition, poor low-temperature storage stability is also a defect of many existing liquid crystal materials.
Therefore, in the field of liquid crystal materials, there is a need for novel liquid crystal compositions having improved properties. In particular, for many types of applications, the liquid crystal composition must have suitably high optical anisotropy, excellent power saving performance, and a fast response speed.
Disclosure of Invention
The object of the present invention is to provide a liquid crystal composition having a fast response speed, excellent power saving performance and suitably high optical anisotropy by an optimized combination and preferred formulation of various liquid crystal compositions which may show none or at least to a significantly lesser extent the disadvantages of the prior art materials.
To accomplish the above object, the present invention provides a liquid crystal composition comprising four compounds corresponding to the following structural formulae i, ii, iii, iv, wherein:
(1) 1-35% of the total weight of the liquid crystal composition of a compound of formula (I)
(2) 1-50% of a compound of formula (II) based on the total weight of the liquid crystal composition
(3) 30-75% of a compound of formula (III) based on the total weight of the liquid crystal composition
And
(4) 0-30% of a compound of formula (IV) based on the total weight of the liquid crystal composition
Wherein,
R1and R2May be the same or different and is independently selected from the group consisting of H, halogen, a halogenated or non-halogenated alkyl or alkoxy group having 1 to 7 carbon atoms, a halogenated or non-halogenated alkanyl or alkoxyalkenyl group having 2 to 7 carbon atoms, wherein, in said R, R is1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
R3、R4and R5Selected from the group consisting of H, halogen, halogenated or non-halogenated alkyl or alkoxy groups having 1 to 10 carbon atoms and halogenated or non-halogenated alkanyl or alkoxyalkenyl groups having 2 to 10 carbon atoms, wherein, in said R3One or more-CH of2The-groups may each independently be substituted with-CH = CH-, -O-, -CH = CF-, -CF = CH-),-CF = CF-, -CO-O-or-O-CO-substitution with the proviso that oxygen atoms are not directly attached to each other;
R6and R7May be the same or different and are each independently selected from the group consisting of H, halogen, a halogenated or non-halogenated alkyl or alkoxy group having 1 to 10 carbon atoms and a halogenated or non-halogenated alkenyl group having 2 to 10 carbon atoms, wherein, in said R5And R6One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
Z1、Z2、Z3、Z4、Z5、Z6、Z7can be the same or different and are respectively and independently selected from single bond, -O-, -COO-, -OCO-, -C2H4-、-CH2O-、-CH2CH2-、-CH=CH-、-CF=CF-、-CF2O-or-C ≡ C-;
Y1and Y2Can be the same or different and are respectively and independently selected from H, CH3Or F;
L1、L2、L3、L4、L5、L6may be the same or different and are each independently selected from H or F;
can be the same or different and are each independently selected from
May be the same or different, are divided intoAre each independently selected fromWherein saidOne or two non-adjacent-CH2-may be substituted by O;
m and n are the same or different and each independently represent 0, 1 or 2, and 0. ltoreq. m + n. ltoreq.3;
a. b are identical or different and each independently of the other represents 0, 1 or 2 and 0. ltoreq. a + b. ltoreq.3;
c. d, e and f are identical or different and each independently of the other represent 0, 1 or 2 and 1. ltoreq. c + d + e + f. ltoreq.5;
q represents 0 or 1.
In an embodiment of the invention, the compound of formula (i) is selected from one or more compounds of the group consisting of:
and
wherein,
R1independently selected from the group consisting of fluorinated or non-fluorinated alkyl or alkoxy groups having 1 to 5 carbon atoms and fluorinated or non-fluorinated alkanyl or alkoxyalkenyl groups having 2 to 5 carbon atoms;
R2independently of each otherSelected from H, F, fluorinated or non-fluorinated alkyl or alkoxy having 1-8 carbon atoms and fluorinated or non-fluorinated alkanyl or alkoxyalkenyl having 2-8 carbon atoms, wherein, in said R1、R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
In an embodiment of the invention, the compound of formula (ii) is selected from one or more compounds of the group consisting of:
and
wherein,
R3selected from the group consisting of fluorinated or non-fluorinated alkyl or alkoxy groups having 1 to 8 carbon atoms and fluoro-substituted or non-fluoro-substituted alkanyl or alkoxyalkenyl groups having 2 to 8 carbon atoms.
In an embodiment of the invention, the compound of formula (iii) is selected from one or more compounds of the group consisting of:
and
wherein,
R4selected from the group consisting of a fluorinated or non-fluorinated alkyl or alkoxy group having 2 to 8 carbon atoms and a fluorinated or non-fluorinated alkanyl or alkoxyalkenyl group having 2 to 5 carbon atoms, wherein, in said R4One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
R5selected from the group consisting of H, F and a fluorinated or non-fluorinated alkyl or alkoxy group having 1 to 8 carbon atoms and a fluorinated or non-fluorinated alkanyl or alkoxyalkenyl group having 2 to 5 carbon atoms, wherein, in said R5One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
In an embodiment of the present invention, the compound of the general formula (iv) is one or more compounds selected from the group consisting of:
and
wherein,
R6independently selected from the group consisting of fluorinated or non-fluorinated alkyl or alkoxy groups having 1 to 8 carbon atoms and fluorinated or non-fluorinated alkanyl or alkoxyalkenyl groups having 2 to 8 carbon atoms;
R7independently selected from H, -CH2F、-CH2CH2F、-CH2CH2CH2F、-CH2CH2CH2CH2F、-OCH2F、-CH2OCH2F、-CH2CH2OCH2F and-CH = CF2。
In an embodiment of the invention, it is preferred that the compound of formula (i) comprises from 5% to 30% by weight of the total composition; the compound of the general formula (II) accounts for 10 to 45 percent of the total weight of the composition; the compound of the general formula (III) accounts for 40 to 70 percent of the total weight of the composition; the compound of the general formula (IV) accounts for 5 to 25 percent of the total weight of the composition.
Another aspect of the invention provides the use of a liquid crystal composition in the manufacture of an electro-optical device.
In another aspect of the invention, an electro-optical liquid crystal display is provided, comprising the liquid crystal composition of the invention.
The liquid crystal medium comprising the liquid crystal composition is determined by performing a combination experiment on the compounds and comparing with a control, and has the advantages of high response speed, excellent electricity-saving performance and appropriately high optical anisotropy.
As described above, the liquid crystal composition of the present invention is used for a liquid crystal cell, and has a good image display effect and no smear. The voltage has small change along with the temperature, the response is fast at low temperature, and the power saving performance is excellent.
In the present invention, unless otherwise specified, the proportions are weight ratios, all temperatures are in degrees centigrade, and the thickness of the box selected for the response time data test is 7 μm.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
The liquid crystal displays used in the following embodiments are all TN-TFT liquid crystal display devices, have a cell thickness d =7 μm, and are composed of a polarizer (polarizer), an electrode substrate, and the like. The display device is in a normally white mode, i.e. when no voltage difference is applied between the row and column electrodes, a viewer perceives a pixel color that is white. The upper and lower polarizer axes on the substrate are at a 90 degree angle to each other. The space between the two substrates is filled with an optical liquid crystal material.
For convenience of expression, in the following examples, the group structures of the liquid crystal compounds are represented by the codes listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Take the following structure as an example:
the structure is represented by the code in table 1: it can be denoted as 3PTG1 (2F) OP3 as well:
it can be expressed as nCPTPOm, where n in the code represents the number of C atoms of the left alkyl group, e.g., n is "3", i.e., the alkyl group is-C3H7(ii) a C in the code represents cyclohexane; o in the code represents an oxygen atom; p in the code represents phenylene; m in the code represents a C atom of a right alkyl groupNumber, e.g. m is "1", i.e. indicates that the alkyl group at the right end is-CH3。
The shorthand codes of the test items in the embodiments are respectively expressed as:
cp (. degree. C.) clearing Point (. degree. C., nematic-isotropic phase transition temperature)
γ1Torsional viscosity (mPas at 20 ℃ C.)
Δ n optical anisotropy (589 nm, 20 ℃ C.)
Delta dielectric anisotropy (1 KHz, 25 ℃ C.)
Vth: threshold voltage (1 KHZ, 25 ℃, TN 90)
The components used in the examples below, except for the compound of the formula (I), can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Preparation of Compounds of the general formula (I)
1) Reacting a compound of formula 1 in tetrahydrofuran as a solvent at room temperature
(general formula 1)
With a compound of formula 2
(formula 2)
Reacting for 16 hours in the presence of a catalyst of tetrakis (triphenylphosphine) palladium under the protection of nitrogen to obtain a compound of a general formula 3
(general formula 3);
2) in tetrahydrofuran solvent, under the protection of nitrogen, and at the temperature of minus 100 ℃ to minus 50 ℃, the compound of the general formula 4
(general formula 4)
Reaction with nBuLi to give the lithium reagent of the formula 5,
(general formula 5)
And then reacting the lithium reagent with the compound shown in the general formula 3 to obtain the compound shown in the general formula (I).
R in the above general formula (general formula 1, general formula 3, general formula 4 and general formula 5)1、R2And R in the general formula (I)1、R2In a range of (A) is uniform, R1、R2Each independently represents H, halogen, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 7 carbon atoms or a halogenated or unsubstituted alkanyl or alkoxyalkenyl group having 2 to 7 carbon atoms, wherein in the R1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other; are the same or different and are each independently selected from the group consisting of A group of (a); z1、Z2、Z3And Z4Identical or different, each independently of the others, selected from the group consisting of-CO-O-, -O-CO-, -CF2O-、-OCF2-、-CH2O-、-OCH2-、-CH2CH2-、-(CH2)4-、-C2F4-、-CH2CF2-, -CF = CF-, -CH = CH-and a single bond; m, n, p and t are identical or different and each independently of the other represents 0, 1 or 2, and m + n + p + t.ltoreq.3.
Preparation example
The specific process steps for synthesizing the prepared compound I-8-2 are as follows:
1) synthesis of Lithium Diisopropylamide (LDA)
Adding 115ml of diisopropylamine and 100ml of Tetrahydrofuran (THF) into a 1000ml three-neck flask, under the protection of nitrogen, dropwise adding 320ml of n-butyllithium (n-BuLi, 2.4 mol/L) at the temperature of 0 to-20 ℃, and stirring for 1 hour at the temperature of 0 to-20 ℃ after dropwise adding to obtain the LDA.
2) Synthesis of trifluorovinyl Zinc chloride
Adding 53g of anhydrous zinc chloride and 100ml of THF into a 1000ml three-neck flask, reducing the temperature to-70 ℃ under the protection of nitrogen, introducing 54g of 1,1,1, 2-tetrafluoroethane gas, introducing a needle tube at the temperature of-50 ℃ to-70 ℃ under the liquid level, slowly injecting LDA, and stirring for 2 hours after the addition is finished to obtain the trifluorovinyl zinc chloride.
3) Synthesis of Compounds of formula 6
(formula 6)
(formula 7)
The compound of formula 7 (45 g, available from the company) and tetrakis (triphenylphosphine) palladium (2 g) were added to the reaction solution of trifluorovinyl zinc chloride prepared above, and reacted at room temperature overnight under nitrogen.
Quenching the reaction with dilute hydrochloric acid ice water solution, extracting with ethyl acetate, combining organic layers, washing with saturated salt water, drying with anhydrous sodium sulfate, spin-drying the solvent, and purifying the residue by distillation under reduced pressure to obtain 22.3g of light green transparent liquid which is the compound of formula 6.
4) Synthesis of Compounds of formula 11
(formula 11)
Adding 2.9g of 3, 5-difluorobromobenzene and 50ml of tetrahydrofuran into a 100ml three-neck flask, cooling to-78 ℃ under the protection of nitrogen, slowly dropwise adding 7.5ml of 2.4mol/L n-butyllithium, and reacting for 2 hours at the temperature controlled below-70 ℃ to obtain the m-fluorobenzene lithium reagent.
The obtained compound of formula 6 (14 g) was dissolved in 20ml of tetrahydrofuran, the temperature was controlled to-70 ℃ or lower, and this was dropped into the above-obtained m-fluorobenzenelithium reagent to react overnight at room temperature.
After the reaction is completed, the reaction is quenched by dilute ice hydrochloric acid water, extracted by ethyl acetate, washed by water, dried by anhydrous sodium sulfate, and subjected to spin-drying of a solvent, and column chromatography by taking petroleum ether as an eluent to obtain 3.4g of light yellow liquid. Column chromatography on silica gel using petroleum ether as eluent gave 1.1g of the compound of formula 11. MS: m/z: 334.13.
5) Synthesis of Compound of formula 12
(formula 12)
Adding a magnetic stirrer, 1.1g of the compound of formula 11, 20ml of THF and nitrogen protection into a 100ml three-neck flask, cooling to-80 ℃, slowly dropwise adding 1.2ml of n-BuLi to ensure that the reaction color begins to change from red to dark green and finally to blue, stirring and reacting for 2 hours at the temperature of-80 ℃, dropwise adding CF2Br2(2g) The color of the reaction solution is changed into yellow, and the reaction is stirred for 1 hour at the temperature of minus 80 ℃.
Quenching with 20ml ice water, adjusting pH to about 6 with hydrochloric acid, extracting with ethyl acetate, combining organic layers, washing the organic layer with water, washing with saturated saline solution, drying, spin-drying solvent, performing column chromatography, and pulping with ethanol to obtain 1g white solid which is the compound of formula 12, wherein the yield is 62.5%. MS: m/z: 462.04.
6) Synthesis of Compound I-8-2
A100 ml single-neck flask was charged with 1g of the compound of formula 12, 0.35g of 3,4, 5-trifluorophenol, 0.6g of potassium carbonate, 0.03g of potassium iodide (KI) and 30ml of N, N-Dimethylformamide (DMF), stirred, purged with nitrogen and reacted at 80 ℃ for 3 hours.
Pouring the reaction solution into water, extracting with ethyl acetate, combining organic layers, washing the organic layers with water, drying, and spin-drying the solvent under reduced pressure. And performing column chromatography with silica gel using petroleum ether as eluent. Pulping with ethanol gave 0.5g of (I-8-2) as a white solid in 43.5% yield. MS: m/z: 530.2.
Liquid Crystal Properties of Compound I-8-2:
Δn:0.176 Δ:16.2 Cp:73.8℃
liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Tables 2 and 4 show the components and ratios of the liquid crystal composition of the comparative example and the results of the performance test conducted by filling the liquid crystal composition between two substrates of a liquid crystal display, so as to compare the performance with the liquid crystal composition of the present invention.
Comparative example 1
The liquid crystal compositions of the comparative examples were prepared according to the compounds and weight percentages listed in table 2, and were filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 2 liquid crystal composition formulations and their test properties
Example 1
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 3, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
As can be seen from comparison between example 1 and comparative example 1, the composition provided by the present invention has suitably high optical anisotropy, suitably high dielectric anisotropy, and relatively low threshold voltage, so that the liquid crystal device has excellent power saving performance, and relatively low viscosity, and thus can achieve a fast response speed, and thus is suitable for use in a notebook computer device.
Comparative example 2
The liquid crystal compositions of the comparative examples were prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 5, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
It can be seen from comparing example 2 with comparative example 2 that the composition provided by the present invention has very low viscosity, thereby enabling to achieve fast response speed, low threshold voltage, while having suitably high optical anisotropy, high dielectric anisotropy. Therefore, the method is suitable for the notebook computer equipment.
Example 3
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 6, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
The composition is characterized by favorable optical anisotropy, high dielectric anisotropy, low rotational viscosity, high clearing point, fast response speed and excellent power saving performance.
Example 4
The liquid crystal composition of the present invention is prepared according to the compounds and weight percentages listed in table 7, and is filled between two substrates of a liquid crystal display for performance test, and the test data is shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
The compositions are characterized by favorable optical anisotropy, very high dielectric anisotropy, low rotational viscosity, very high clearing point and fast response speed.
Claims (4)
1. A liquid crystal composition consisting of:
(1) 10-15% by weight of the total liquid crystal composition of one or more compounds selected from the group consisting of:
and
(2) 12-24.5% by weight of the total liquid crystal composition of one or more compounds selected from the group consisting of:
and
(3) 45-75% by weight of the total liquid crystal composition of one or more compounds selected from the group consisting of:
and
and
(4) 0-14% by weight of the total liquid crystal composition of one or more compounds selected from the group consisting of:
and
wherein R is1Selected from fluorine having 1 to 5 carbon atomsSubstituted or non-fluorinated alkyl or alkoxy;
R2selected from the group consisting of H, F, fluorinated or non-fluorinated alkyl or alkoxy groups having 1-8 carbon atoms;
R3selected from the group consisting of fluorinated or non-fluorinated alkyl or alkoxy groups having 1 to 8 carbon atoms;
R4selected from the group consisting of fluorinated or non-fluorinated alkyl or alkoxy groups having 2 to 8 carbon atoms;
R5selected from the group consisting of H, F and a fluorinated or non-fluorinated alkyl or alkoxy group having 1 to 8 carbon atoms and a fluorinated or non-fluorinated alkanyl or alkoxyalkenyl group having 2 to 5 carbon atoms;
R6independently selected from fluorinated or non-fluorinated alkyl or alkoxy groups having 1 to 8 carbon atoms.
2. The liquid crystal composition of claim 1, wherein the liquid crystal composition comprises:
compound III-2-1 in an amount of 12% by weight based on the total weight of the liquid crystal composition
Compound III-8-1 in an amount of 2% by weight based on the total weight of the liquid crystal composition
Compound III-7-1 accounting for 2 percent of the total weight of the liquid crystal composition
Compound III-2 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound II-1 accounting for 5 percent of the total weight of the liquid crystal composition
Compound II-1-2 accounting for 10 percent of the total weight of the liquid crystal composition
Compound III-4-1 accounting for 7 percent of the total weight of the liquid crystal composition
Compound III-5-1 in an amount of 10% by weight based on the total weight of the liquid crystal composition
Compound III-9-1 accounting for 38 percent of the total weight of the liquid crystal composition
And
compound I-8-2 accounting for 10 percent of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
compound III-2-1 in an amount of 10% by weight based on the total weight of the liquid crystal composition
Compound II-1 accounting for 8 percent of the total weight of the liquid crystal composition
Compound II-1-2 accounting for 8 percent of the total weight of the liquid crystal composition
Compound II-3-1 accounting for 4 percent of the total weight of the liquid crystal composition
Compound II-3-2 accounting for 6 percent of the total weight of the liquid crystal composition
Compound III-9-1 accounting for 35 percent of the total weight of the liquid crystal composition
A compound IV-11-1 accounting for 6 percent of the total weight of the liquid crystal composition
A compound IV-6-1 accounting for 5 percent of the total weight of the liquid crystal composition
A compound IV-6-2 accounting for 3 percent of the total weight of the liquid crystal composition
3 percent of compound I-8-2 in the total weight of the liquid crystal composition
Compound I-8-1 accounting for 4 percent of the total weight of the liquid crystal composition
Compound I-1 accounting for 4 percent of the total weight of the liquid crystal composition
And
compound I-1-2 accounting for 4 percent of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
3.5 percent of compound II-4-1 based on the total weight of the liquid crystal composition
Compound II-4-2 accounting for 7 percent of the total weight of the liquid crystal composition
Compound II-5-1 accounting for 3 percent of the total weight of the liquid crystal composition
Compound II-5-2 accounting for 11 percent of the total weight of the liquid crystal composition
13% of compound III-10-1 by weight of the total liquid crystal composition
Compound III-9-2 in an amount of 16% by weight based on the total weight of the liquid crystal composition
Compound III-1 in an amount of 2.5% by weight based on the total weight of the liquid crystal composition
Compound III-1-2 in an amount of 4% by weight based on the total weight of the liquid crystal composition
Compound III-1-3 in an amount of 6% by weight based on the total weight of the liquid crystal composition
Compound III-1-4 in an amount of 6% by weight based on the total weight of the liquid crystal composition
Compound III-1-5 in 6 wt% of the total liquid crystal composition
Compound III-6-1 accounting for 8 percent of the total weight of the liquid crystal composition
7 percent of compound I-8-2 in the total weight of the liquid crystal composition
And
7 percent of compound I-8-1 based on the total weight of the liquid crystal composition
3. Use of a liquid crystal composition according to any of claims 1-2 in the manufacture of an electro-optical device.
4. An electro-optical liquid crystal display comprising a liquid crystal composition according to any one of claims 1 to 2.
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| CN103409146B (en) * | 2013-04-01 | 2015-10-28 | 石家庄诚志永华显示材料有限公司 | For the liquid-crystal composition of driven with active matrix liquid-crystal display |
| TWI518174B (en) * | 2013-05-13 | 2016-01-21 | 達興材料股份有限公司 | Liquid crystal medium and liquid crystal display apparatus |
| CN105038813B (en) * | 2015-07-13 | 2017-09-29 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal composition |
| CN107779201B (en) * | 2016-08-29 | 2021-03-05 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display element |
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