CN103773389B - Containing the liquid-crystal composition of pyranylation compound - Google Patents
Containing the liquid-crystal composition of pyranylation compound Download PDFInfo
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- CN103773389B CN103773389B CN201410029975.7A CN201410029975A CN103773389B CN 103773389 B CN103773389 B CN 103773389B CN 201410029975 A CN201410029975 A CN 201410029975A CN 103773389 B CN103773389 B CN 103773389B
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- 0 *C(CC1)CC*1C1C*C(*)CC1 Chemical compound *C(CC1)CC*1C1C*C(*)CC1 0.000 description 8
- MYCJQLJISDOEHP-UHFFFAOYSA-N C[IH]c1cc(O)cc(N)c1O Chemical compound C[IH]c1cc(O)cc(N)c1O MYCJQLJISDOEHP-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to a kind of liquid-crystal composition containing pyranylation compound, comprise the compound shown in one or more general formula Is, the compound shown in one or more general formula Is I, the compound shown in one or more general formula III, the compound shown in one or more general formula Is V, the compound shown in one or more general formulas V; Liquid-crystal composition excellent performance provided by the invention, has the features such as the optical anisotropy that rotary viscosity is low, the time of response is fast, nematic phase range is wide, suitable, is applicable in active matrix electrooptic element and liquid-crystal display, can be used for manufacturing TFT-LCD.In each general formula, each parameter has the implication provided in specification sheets,
Description
Technical field
The present invention relates to a kind of liquid-crystal composition containing pyranyl liquid crystalline cpd, especially a kind of liquid-crystal composition applied in Active Matrix Display, especially TN, STN, IPS and VA indicating meter.
Background technology
The liquid-crystal display of liquid-crystal composition is used to be widely used in the indicating meters such as instrument, computer, TV.For technical field of liquid crystal display, although market is very huge in recent years, technology is also ripe gradually.Liquid crystal display device is divided into following modes according to display mode: twisted nematic (TN) pattern, super-twist nematic (STN) pattern, plane modes (IPS), vertical orientation (VA) pattern, Thin Film Transistor-LCD (TFT-LCD) has become the Developing mainstream of flat pannel display.The TFT-LCD of high-quality requires high-contrast, high definition, high-speed response, high brightness and wide viewing angle.In addition, low power consumption is also required.No matter which kind of display format all need liquid-crystal composition the to have optical anisotropy Δ n that chemistry and physical properties are stablized, rotary viscosity is low, suitable, suitable dielectric anisotropy Δ ε, with the characteristic such as the intermiscibility of other liquid crystalline cpds is good.
But also use in a liquid crystal display separately without any single liquid crystal monomer so far, and just need not can meet performance requriements with other compound combination.If two or more liquid crystal monomer is mixed, just can change the various types of properties of liquid crystal continuously, general commodity liquid-crystal composition is also all mixed by various of monomer liquid crystal substantially.
Liquid crystal molecule introduces sub-the methoxyl group (-CF of a difluoro
2o-) after, its nematic temperature range can be made to expand significantly, and rotary viscosity γ 1 also decreases, and the dielectric anisotropy Δ ε of liquid crystal molecule is increased to some extent.Merck KGaA and Japanese Chisso Corporation have disclosed the liquid crystalline cpd (CN1717468A, CN101143808A, CN101157862A etc.) with the sub-methoxyl group (-CF2O-) of difluoro that some have different substituents.After liquid crystal molecule introduces an amylene oxide ring, due to the introducing of Sauerstoffatom on ring, add the moment of dipole of molecule, all can play the effect enlarging markedly dielectric anisotropic to positivity, negative liquid crystal, and there is very excellent intermiscibility and low rotary viscosity.In addition, the effect increasing nematic phase warm area can also be played.Merck KGaA company has disclosed the liquid crystalline cpd (CN1806028A, CN101506189A etc.) with amylene oxide ring that some have different substituents.
Summary of the invention
The technical issues that need to address of the present invention are to provide a kind of positive dielectric liquid crystal composite, especially a kind of liquid-crystal composition containing pyranylation compound, make to have the features such as the optical anisotropy that rotary viscosity is low, the time of response is fast, nematic phase range is wide, suitable, be applicable in active matrix electrooptic element and liquid-crystal display, can be used for manufacturing TFT-LCD.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
Containing the liquid-crystal composition of pyranylation compound, comprise the component A be made up of the compound shown in one or more general formula Is, the component B be made up of the compound shown in one or more general formula Is I, the component C be made up of the compound shown in one or more general formula III, the component D be made up of the compound shown in one or more general formula Is V, the component E that is made up of the compound shown in one or more general formulas V;
Wherein,
R
11, R
12be respectively 1. following ~ 4. described group wherein any one,
①：H、Cl、F、CN、OCN、OCF
3、CF
3、CHF
2、CH
2F、OCHF
2、SCN、NCS、SF
5，
2.: C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15straight alkenyloxy,
3.: the one or more-CH in group 2.
2-substituted rear and that Sauerstoffatom is directly not connected group by-CH=CH-,-C ≡ C-,-COO-,-OOC-, sub-cyclobutyl, cyclopentylidene ,-O-or-S-,
4.: the group after any H of group 2. or is 3. replaced by F, Cl;
Ring A
11for
in one;
Ring A
12, ring A
13, ring A
14be respectively singly-bound,
in one;
Z
11, Z
12, Z
13be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-(CH
2)
3-,-(CH
2)
4-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-,-CF
2cH
2-,-CH
2cF
2-,-C
2f
4-, one in-CF=CF-;
A, b, c, d are respectively 0,1,2,3, and a+b+c+d≤5;
R
21, R
22, R
31, R
32, R
41, R
42, R
51, R
52be respectively F, Cl, CN, C
1~ C
7straight chained alkyl, C
1~ C
7unbranched alkoxy, C
2~ C
7straight-chain alkenyl, C
1~ C
5straight chain fluoroalkyl;
Ring A
21, ring A
22, ring A
31, ring A
41, ring A
42, ring A
51, ring A
52, ring A
53be respectively singly-bound,
in one;
Z
51be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-in one;
L
21, L
22, L
41be respectively the one in H, F, Cl, CN;
E, f, g, h, i, j are respectively 0,1,2.
Further improvement of the present invention is:
R
11for H, C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15one in straight alkenyloxy,
R
12for H, Cl, F, CN, OCN, OCF
3, CF
3, CHF
2, CH
2f, OCHF
2, SCN, NCS, SF
5, C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15one in straight alkenyloxy,
Z
11, Z
12, Z
13be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-(CH
2)
3-,-(CH
2)
4-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-in one.
Further improvement of the present invention is: in liquid-crystal composition, component A accounts for the weight percentage of liquid-crystal composition is 1% ~ 40%, the weight percentage that B component accounts for liquid-crystal composition is 1% ~ 60%, the weight percentage that component C accounts for liquid-crystal composition is 10% ~ 70%, the weight percentage that component D accounts for liquid-crystal composition is 1% ~ 30%, the weight percentage that component E accounts for liquid-crystal composition is 1% ~ 50%, said components A, B component, component C, component D, component E weight percentage be 100%.
Further improvement of the present invention is: in liquid-crystal composition, component A accounts for the weight percentage of liquid-crystal composition is 8% ~ 19%, the weight percentage that B component accounts for liquid-crystal composition is 5% ~ 40%, the weight percentage that component C accounts for liquid-crystal composition is 33% ~ 49%, the weight percentage that component D accounts for liquid-crystal composition is 3% ~ 10%, the component E weight percentage accounting for liquid-crystal composition is 5% ~ 30.5%.
Owing to have employed technique scheme, the technical progress acquired by the present invention is:
The compound of general formula I representative of the present invention, there is the necessary general physical properties of liquid crystal monomer compound, to light, thermally-stabilised, nematic phase range is wider, good with other Compound Phase dissolubilities, especially this compounds has higher optical anisotropy Δ n, larger dielectric anisotropy (Δ ε > 0) and low rotary viscosity γ
1characteristic, effectively can reduce the threshold voltage of mixed liquid crystal, accelerate the time of response simultaneously, improve the low temperature intersolubility of mixed liquid crystal.
The Nematic phase liquid crystal composition excellent performance obtained by the present invention, has low-down overall response time, has lower voltage, high resistivity and voltage retention.By the adjustment to each component concentration, Nematic phase liquid crystal composition of the present invention can have different threshold voltages and birefringent characteristic, can make each individual system that client is usually used, uses under being convenient to thick at different liquid crystal cell in different driving voltage.And liquid-crystal composition still can show high resistivity after high temperature, this liquid-crystal composition shows the excellent high temperature with excellence and UV stable performance.Meanwhile, in embodiment, liquid-crystal composition also shows low viscosity, fast-response time, suitable optical anisotropy and suitable dielectric anisotropy, therefore can have the Electro-Optical Display of active array addressing.
What the present invention relates to is the application of a class pyranyl difluoro methylene oxo bridge ether type monomer in liquid-crystal composition, this type of pyranyl difluoro methylene ether compound is novel compounds, application in liquid-crystal composition still belongs to the first time, and therefore similar liquid-crystal composition has no any report.The liquid crystal material using this kind of pyranyl difluoro methylene oxygen ether class monomer to develop excellent performance has initiative meaning, and the liquid-crystal composition developed has the performance of very outstanding excellence.Great concerning being worth high-end TFT indicating meter liquid crystal material.
Liquid-crystal composition of the present invention; may be used for Active Matrix Display; preferably by the matrix addressing of thin film transistor (TFT); be specially adapted to the active matrix TN-TFT manufacturing response fast; IPS-TFT or FFS liquid crystal display device and liquid-crystal display, also belong to protection scope of the present invention.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated:
The concrete meaning of the symbol in embodiment and test condition as follows:
Cp: clearing point, unit DEG C;
Δ n: optical anisotropy, Δ n=no-ne, wherein, no is the specific refractory power of ordinary light, and ne is the specific refractory power of extraordinary ray, and test condition is, 589nm, 25 ± 0.5 DEG C;
Δ ε: dielectric anisotropy, Δ ε=ε
//-ε
⊥, wherein, ε
//for being parallel to the specific inductivity of molecular axis, ε
⊥for the specific inductivity perpendicular to molecular axis, test condition is 25 ± 0.5 DEG C; 1KHz; HP4284A; 5.2 the left-handed box of micron TN;
γ
1: rotary viscosity, unit mPas, test condition is 25 ± 0.5 DEG C.
Containing the liquid-crystal composition of pyranylation compound, comprise the component A be made up of the compound shown in one or more general formula Is, the component B be made up of the compound shown in one or more general formula Is I, the component C be made up of the compound shown in one or more general formula III, the component D be made up of the compound shown in one or more general formula Is V, the component E that is made up of the compound shown in one or more general formulas V;
Wherein,
R
11, R
12be respectively 1. following ~ 4. described group wherein any one,
①：H、Cl、F、CN、OCN、OCF
3、CF
3、CHF
2、CH
2F、OCHF
2、SCN、NCS、SF
5，
2.: C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15straight alkenyloxy,
3.: the one or more-CH2-in group are 2. substituted rear and that Sauerstoffatom is directly not connected group by-CH=CH-,-C ≡ C-,-COO-,-OOC-, sub-cyclobutyl, cyclopentylidene ,-O-or-S-,
4.: the group after any H of group 2. or is 3. replaced by F, Cl;
Ring A
11for
in one;
Ring A
12, ring A
13, ring A
14be respectively singly-bound,
in one;
Z
11, Z
12, Z
13be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-(CH
2)
3-,-(CH
2)
4-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-,-CF
2cH
2-,-CH
2cF
2-,-C
2f
4-, one in-CF=CF-;
A, b, c, d are respectively 0,1,2,3, and a+b+c+d≤5;
R
21, R
22, R
31, R
32, R
41, R
42, R
51, R
52be respectively F, Cl, CN, C
1~ C
7straight chained alkyl, C
1~ C
7unbranched alkoxy, C
2~ C
7straight-chain alkenyl, C
1~ C
5straight chain fluoroalkyl;
Ring A
21, ring A
22, ring A
31, ring A
41, ring A
42, ring A
51, ring A
52, ring A
53be respectively singly-bound,
in one;
Z
51be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-in one;
L
21, L
22, L
41be respectively the one in H, F, Cl, CN;
E, f, g, h, i, j are respectively 0,1,2.
Preferably,
R
11for H, C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15one in straight alkenyloxy,
R
12for H, Cl, F, CN, OCN, OCF
3, CF
3, CHF
2, CH
2f, OCHF
2, SCN, NCS, SF
5, C
1~ C
15straight chained alkyl, C
1~ C
15unbranched alkoxy, C
2~ C
15straight-chain alkenyl, C
2~ C
15one in straight alkenyloxy,
Z
11, Z
12, Z
13be respectively singly-bound ,-CH
2-,-CH
2-CH
2-,-(CH
2)
3-,-(CH
2)
4-,-CH=CH-,-C ≡ C-,-COO-,-OOC-,-CF
2o-,-OCH
2-,-CH
2o-,-OCF
2-in one.
Of the present invention containing in the liquid-crystal composition of pyranylation compound, in liquid-crystal composition, component A accounts for the weight percentage of liquid-crystal composition is 1% ~ 40%, is preferably 8% ~ 19%; The weight percentage that B component accounts for liquid-crystal composition is 1% ~ 60%, is preferably 5% ~ 40%; The weight percentage that component C accounts for liquid-crystal composition is 10% ~ 70%, is preferably 33% ~ 49%; The weight percentage that component D accounts for liquid-crystal composition is 1% ~ 30%, is preferably 3% ~ 10%; The weight percentage that component E accounts for liquid-crystal composition is 1% ~ 50%, is preferably 5% ~ 30.5%; The weight percentage of said components A, B component, component C, component D, component E is 100%.
Compound shown in liquid-crystal composition formula of I containing pyranylation compound of the present invention can one or more preferably in compound shown in following formula I-1 ~ formula I-4, compound shown in general formula I I can one or more preferably in compound shown in following formula II-1 ~ formula II-10, compound shown in general formula III can one or more preferably in compound shown in following formula III-1 ~ formula III-4, compound shown in general formula I V can one or more preferably in compound shown in following formula IV-1 ~ formula IV-4, shown in general formula V, compound is specially one or more in compound shown in following formula V-1 ~ formula V-12,
Wherein,
Ring A
11for
in one,
R
11for H or C
1~ C
10straight chained alkyl in one,
R
12for F, Cl, OCF
3, CF
3, one in CN, NCS,
(F) be H or F.
Compound shown in liquid-crystal composition formula of I containing pyranylation compound of the present invention can one or more further preferably in compound shown in following formula I-1-1 ~ formula I-4-6,
Wherein,
R
11for H, CH
3, C
2h
5, C
3h
7, n-C
4h
9, n-C
5h
11, n-C
6h
13in one.
The each composition adopted in following embodiment 1 ~ 5, all can be synthesized by known method, or be obtained by commercial sources.These synthetic technologys are conventional, and each liquid crystalline cpd obtained meets electrical type compound standard after tested.
The weight percentage of each liquid-crystal composition specified according to following examples 1 ~ 5, prepares liquid-crystal composition.The preparation of described liquid-crystal composition carries out according to the ordinary method of this area, and as taked heating, ultrasonic wave, ratio mixing is obtained according to the rules for the modes such as suspension.
Embodiment 1
Liquid-crystal composition of the present invention is mixed with by following listed each compound and weight percentage,
Be filled in by above-mentioned liquid-crystal composition between liquid-crystal display two substrates and carry out performance test, test result is, Cp:87 DEG C; Δ n:0.105; Δ ε: 7.2; γ
1: 65mPas;
This liquid-crystal composition has higher clearing point, moderate optical anisotropy, suitably high dielectric anisotropy, very low rotation viscosity, is therefore applicable to very much the TN-TFT of response fast, IPS-TFT indicating meter.
Embodiment 2
Liquid-crystal composition of the present invention is mixed with by following listed each compound and weight percentage,
Be filled in by above-mentioned liquid-crystal composition between liquid-crystal display two substrates and carry out performance test, test result is, Cp:94 DEG C; Δ n:0.125; Δ ε: 7.8; γ
1: 65mPas;
This liquid-crystal composition has higher clearing point, slightly high optical anisotropy, suitably high dielectric anisotropy, very low rotation viscosity, is therefore applicable to very much the TN-TFT indicating meter of response fast.
Embodiment 3
Liquid-crystal composition of the present invention is mixed with by following listed each compound and weight percentage,
Be filled in by above-mentioned liquid-crystal composition between liquid-crystal display two substrates and carry out performance test, test result is, Cp:87 DEG C; Δ n:0.105; Δ ε: 7.2; γ
1: 65mPas;
This liquid-crystal composition has higher clearing point, moderate optical anisotropy, suitably high dielectric anisotropy, very low rotation viscosity, is therefore applicable to very much the IPS-TFT indicating meter of response fast.
Embodiment 4
Liquid-crystal composition of the present invention is mixed with by following listed each compound and weight percentage,
Be filled in by above-mentioned liquid-crystal composition between liquid-crystal display two substrates and carry out performance test, test result is, Cp:87 DEG C; Δ n:0.112; Δ ε: 7.7; γ
1: 65mPas;
This liquid-crystal composition has higher clearing point, higher optical anisotropy, suitably high dielectric anisotropy, very low rotation viscosity, is therefore applicable to very much the IPS-TFT indicating meter of response fast.
Embodiment 5
Liquid-crystal composition of the present invention is mixed with by following listed each compound and weight percentage,
Be filled in by above-mentioned liquid-crystal composition between liquid-crystal display two substrates and carry out performance test, test result is, Cp:87 DEG C; Δ n:0.110; Δ ε: 6.9; γ
1: 63mPas;
This liquid-crystal composition has higher clearing point, moderate optical anisotropy, suitably high dielectric anisotropy, very low rotation viscosity, is therefore applicable to very much the TN-TFT indicating meter of response fast.
Above 5 embodiments, all have good low-temperature stability, low rotary viscosity, maintain the fast time of response at low-temperature region.Can widen TN-TFT, the use temperature of IPS-TFT or FFS-TFT liquid crystal mode, and have time of response and wider angular field of view faster, be highly suitable for TN-TFT, IPS-TFT and FFS-TFT shows.
Liquid-crystal composition provided by the present invention is by using the difluoro methylene ether compound containing pyranyl, have and reduce threshold voltage and the effect of time of response, therefore the present invention develop liquid-crystal composition be desirable liquid crystal material for the preparation of the TFT LCD responded fast.
Although the present invention only lists particular compound and the proportioning consumption (weight percentage) thereof of above-mentioned 5 embodiments, and carried out performance test, but liquid-crystal composition of the present invention can on the basis of above-described embodiment, utilize the liquid crystalline cpd representated by general formula I involved in the present invention, II, III, IV and general formula I, the preferred liquid crystalline cpd of II, III, IV expands further and revise, by suitably adjusting its proportioning consumption, all object of the present invention can be reached.
Claims (3)
1., containing the liquid-crystal composition of pyranylation compound, it is characterized in that:
Comprise the component A be made up of compound shown in one or more formula I-1 ~ formula I-4, the component B be made up of the compound shown in one or more general formula II-1 ~ general formulas II-10, the component C be made up of the compound shown in one or more general formula III-1 ~ general formula III-4, the component D be made up of the compound shown in one or more general formulae IV-1 ~ general formulae IV-3, the component E that is made up of the compound shown in one or more general formula V-1 ~ general formulas V-12; In liquid-crystal composition, component A accounts for the weight percentage of liquid-crystal composition is 1% ~ 40%, the weight percentage that B component accounts for liquid-crystal composition is 1% ~ 60%, the weight percentage that component C accounts for liquid-crystal composition is 10% ~ 70%, the weight percentage that component D accounts for liquid-crystal composition is 1% ~ 30%, the weight percentage that component E accounts for liquid-crystal composition is 1% ~ 50%, said components A, B component, component C, component D, component E weight percentage be 100%;
Wherein:
R
11for H, C
1~ C
10one in straight chained alkyl;
R
12for Cl, F, CN, OCF
3, CF
3, one in NCS;
Ring A
11for
in one;
R
21, R
22, R
31, R
32, R
41, R
42, R
51, R
52be respectively F, Cl, CN, C
1~ C
7straight chained alkyl, C
1~ C
7unbranched alkoxy, C
2~ C
7straight-chain alkenyl, C
1~ C
5straight chain fluoroalkyl;
(F) be H or F.
2. the liquid-crystal composition containing pyranylation compound according to claim 1, is characterized in that:
Compound shown in described formula I is specially one or more in compound shown in following formula I-1-1 ~ formula I-4-6,
Wherein,
R
11for H, CH
3, C
2h
5, C
3h
7, n-C
4h
9, n-C
5h
11, n-C
6h
13in one.
3. the liquid-crystal composition containing pyranylation compound according to claim 1, it is characterized in that: in liquid-crystal composition, component A accounts for the weight percentage of liquid-crystal composition is 8% ~ 19%, the weight percentage that B component accounts for liquid-crystal composition is 5% ~ 40%, the weight percentage that component C accounts for liquid-crystal composition is 33% ~ 49%, the weight percentage that component D accounts for liquid-crystal composition is 3% ~ 10%, the component E weight percentage accounting for liquid-crystal composition is 5% ~ 30.5%.
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| CN1806028A (en) * | 2003-05-27 | 2006-07-19 | 默克专利股份有限公司 | Liquid-crystalline compounds having a tetrahydropyran ring |
| CN100999668A (en) * | 2006-01-13 | 2007-07-18 | 默克专利股份有限公司 | Liquid crystal medium |
| CN101332669A (en) * | 2007-06-28 | 2008-12-31 | 西德尔合作公司 | Object transfer device with a transfer arm having a substantially vertically mobile gripping head |
| CN102199139A (en) * | 2010-03-23 | 2011-09-28 | 默克专利股份有限公司 | Liquid crystalline compounds and liquid crystalline media |
| CN103305229A (en) * | 2013-06-06 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition capable of rapidly responding to cyclo-butylbenzene difluoromethoxy |
| CN103555345A (en) * | 2013-08-30 | 2014-02-05 | 石家庄诚志永华显示材料有限公司 | Preparation and application of novel liquid crystal compound |
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