CN106010579B - A kind of liquid-crystal composition - Google Patents
A kind of liquid-crystal composition Download PDFInfo
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- CN106010579B CN106010579B CN201610347190.3A CN201610347190A CN106010579B CN 106010579 B CN106010579 B CN 106010579B CN 201610347190 A CN201610347190 A CN 201610347190A CN 106010579 B CN106010579 B CN 106010579B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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Abstract
The present invention provides a kind of liquid-crystal composition, the liquid-crystal composition contains compound shown in compound shown in one or more formulas I, compound and one or more formulas III shown in one or more formulas II
Description
Technical field
The invention belongs to field of liquid crystal display, and in particular to a kind of liquid-crystal composition and the liquid crystal comprising the liquid-crystal composition
Display element.
Background technique
The optical property of liquid crystal can be changed by the voltage of application, therefore this substance is mainly used as in display equipment
Dielectric.In technical field of liquid crystal display, the electrooptics equipment known to technical staff based on liquid crystal is with each
Based on kind effect.The mode of such equipment mainly includes dynamic scattering mode, DAP (deformation of aligned arrangement phase) mode,
Guest/holotype, the TN mode with twisted-nematic structure, STN (super twisted nematic) mode, SBE (super birefringence effect) mode,
OMI (optical mode interference) mode and OCB (optical compensation curved) mode.
In the system of tft active matrix, mainly there are TN (Twisted Nematic, twisted-nematic structure) mode, IPS
(In-Plane Switching, plane conversion)/FFS (Fringe Field Switching, fringe field switching technique) mode
With the main display pattern such as VA (VerticalAlignment, vertically oriented) mode.
For thin-film transistor technologies (TFT-LCD) application field, develop by the accumulation of decades, technology also gradually at
It is ripe, but requirement of the people to display technology is also in the continuous improvement, in order to further seek for the superiority of image quality, it is desirable to liquid crystal
Display, which can be realized, more rapidly to be responded, and bright-colored, colour gamut is wider；In terms of energy conservation, driving voltage is reduced to reduce power consumption
Etc..The liquid crystal material photoelectron material one of important as liquid crystal display plays the performance for improving liquid crystal display
Important role.
Liquid crystal display is during carrying out Dynamically Announce, such as liquid crystal display or LCD TV, in order to guarantee upper one
The picture that width is shown no longer is shown in next width, causes occur ghost or trailing phenomenon during screen switching, it is desirable to
Liquid crystal display has cracking response speed, and then requires the rotary viscosity of liquid crystal material lower.In addition, in order to reduce equipment
Energy consumption, it is desirable to which the driving voltage of liquid crystal is as low as possible, so the dielectric anisotropy △ ε for improving liquid crystal has weight to mixed liquid crystal
Want meaning.
Liquid crystal material must have good chemical and thermal stability and the good stability to electric field and electromagnetic radiation.This
Outside, liquid crystal material should have low viscosity and generate short addressing time, low threshold voltage and the high contrast in screen.Liquid
Crystalline substance generally as the mixture of several components come using, it is important that these components are easy miscible each other.Other performance, it is such as conductive
Property, dielectric anisotropy and optical anisotropy, it is necessary to meet the various requirement for depending on this type and application field.For example,
The material of mode with twisted nematic structure should have positive dielectric anisotropy and low electric conductivity.
Quaterphenyl class formation (CN200710180192.9) has improvement liquid crystal after UV irradiation for liquid-crystal composition
VHR effect, to improve display effect, however since dissolubility is not good enough, additive amount is limited, limits its effect.
Liquid crystal material will not only have the above feature, while liquid crystal material should have wide nematic temperature range, come
Meet liquid crystal display panel and is widely applied field, such as normal temperature type display device, high temperature modification display device, low form display device.
Monomeric liquid crystal material performance it is superior, directly determine the superior performance of mixed liquid crystal material, therefore develop a comprehensive performance
Superior monomeric liquid crystal material is a very important thing.
Summary of the invention
In order to solve the above-mentioned technical problems, the present invention provides one kind include quaterphenyl structure liquid-crystal composition and comprising
The liquid crystal display element or liquid crystal display of the liquid-crystal composition, the liquid-crystal composition have lower viscosity, may be implemented fast
Speed response, while there is moderate dielectric anisotropy Δ ε, moderate optical anisotropy Δ n, the high stabilization to light and heat
Property.Liquid crystal display element or liquid crystal display comprising the liquid-crystal composition have wider nematic temperature range, suitable
Birefringence anisotropy, very high resistivity, better anti-ultraviolet property, high charge retention rate and low-steam pressure,
The performances such as better low temperature intersolubility.
A kind of liquid-crystal composition is specifically disclosed by invention, the liquid-crystal composition contains one or more I shownization of formula
Close compound shown in compound shown in object, one or more formulas II and one or more formulas III
Wherein, Y1To Y13Each independently represent H or F；
X indicates that the fluoro-alkyl that the alkyl that F, Cl, carbon atom number are 1-6, carbon atom number are 1-6, carbon atom number are 2-6's
The fluoro alkene that the fluoroalkyl or carbon atom number that fluoroolefin that alkene, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in oxygroup；
R1Indicate the alkene that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in base；
R2Indicate H or carbon atom number for the alkyl of 1-3；
R3Indicate the alkene that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in base, any methylene can be replaced by cyclopenta, cyclopropyl；
N indicates 1 or 0；
It indicates
Compound shown in one or more formulas II is preferably one of compound shown in formula II 1 to formula II 8 or more
Kind:
Compound shown in one or more formulas III is preferably one of compound shown in formula III 1 to formula III 12 or more
Kind:
Wherein, R3Indicate the fluoro-alkyl that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6, carbon atom number 2-6
Alkene, carbon atom number be 2-6 fluoroolefin, carbon atom number be 1-6 fluoroalkyl or carbon atom number be 2-6 fluoro
Any group in alkenyloxy group, any methylene can be replaced by cyclopenta, cyclopropyl.
Compound shown in a kind of excessively a variety of formulas I is preferably one of compound shown in formula I 1 to formula I 12 or a variety of:
Compound shown in formula I has better dissolubility, bigger add may be implemented relative to end chain-like alkyl compound
Dosage, to realize the effect of better stabilizing liquid crystal parameter.
The liquid-crystal composition provided by inventing can also include compound shown in one or more formulas IV；
Wherein, R4Indicate the fluoro-alkyl that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6, carbon atom number 2-6
Alkene, carbon atom number be 2-6 fluoroolefin, carbon atom number be 1-6 fluoroalkyl or carbon atom number be 2-6 fluoro
Any group in alkenyloxy group；
R5Indicate the alkene that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that F, carbon atom number are 1-6 are 1-6 are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in base；
It indicates And/orIt is one or more；
P indicates 1,2 or 3；
(F) H or F is each independently represented.
Compound shown in one or more formulas IV is any one or more in the compound of following structural formula:
Wherein, R4It is former to each independently represent fluoro-alkyl, carbon that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6
The fluoroalkyl or carbon atom number that fluoroolefin that alkene that subnumber is 2-6, carbon atom number are 2-6, carbon atom number are 1-6 be
Any group in the fluoro alkenyloxy group of 2-6；
R5Each independently represent F, the fluoro-alkyl that the alkyl that carbon atom number is 1-6, carbon atom number are 1-6, carbon atom
The fluoroalkyl or carbon atom number that fluoroolefin that alkene that number is 2-6, carbon atom number are 2-6, carbon atom number are 1-6 are 2-
Any group in 6 fluoro alkenyloxy group.
In the liquid-crystal composition, the gross mass percent concentration of compound shown in one or more formulas I is preferably
The gross mass percent concentration of 1-15%, compound shown in one or more formulas II are preferably 30-60%, it is described a kind of or
The gross mass percent concentration of compound shown in a variety of formulas III is preferably 5-40%, compound shown in one or more formulas IV
Gross mass percent concentration be preferably 0-30%.
Compound shown in the Formulas I that aforementioned present invention provides is preparing liquid crystal compound, liquid crystal display device material or electric light
Learn application and the liquid crystal compound comprising compound described in Formulas I, liquid crystal display device material or the electric light in display device material
Display device material is learned, protection scope of the present invention is also belonged to.
Specific embodiment
The present invention is further elaborated combined with specific embodiments below, but the present invention is not limited to following embodiments.Institute
State method is conventional method unless otherwise instructed.The raw material can be gotten from open business unless otherwise instructed.
Percentage in this specification is mass percent, and temperature is degree Celsius (DEG C), the specific meaning of other symbols and
Test condition is as follows:
Cp indicates clearing point (DEG C), the test of DSC sizing technique；
S-N indicates the crystalline state of liquid crystal to nematic fusing point (DEG C)；
Δ n indicates that optical anisotropy, no are the refractive index of ordinary light, and ne is the refractive index of extraordinary ray, test condition
It is 25 ± 2 DEG C, 589nm, Abbe refractometer test；
Δ ε indicates dielectric anisotropy, Δ ε=ε ∥-ε ⊥, wherein ε ∥ is the dielectric constant for being parallel to molecular axis, ε ⊥
For the dielectric constant perpendicular to molecular axis, test condition is 25 ± 0.5 DEG C, and 20 microns of parallel boxes, INSTEC:ALCT-IR1 is surveyed
Examination；
The present patent application embodiment liquid crystal monomer structure indicates with code, liquid crystal ring structure, end group, linking group code
Representation method see the table below (one), table (two)
Table (one): the correspondence code of ring structure
Table (two): the corresponding code of end group and the link group
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 1, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 1:
Embodiment 1 and 1 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.4%, 99.1%.
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 2, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 2:
Embodiment 2 and 2 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.5%, 99.3%.
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 3, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 3:
Embodiment 3 and 3 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.8%, 99.7%.
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 4, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 4:
Embodiment 4 and 4 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.9%, 99.8%.
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 5, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 5:
Embodiment 5 and 5 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.8%, 99.7%.
Listed each compound and weight percent are configured to liquid-crystal composition of the invention in embodiment 6, according to the form below,
It is filled between liquid crystal display two substrates and is tested for the property, test data is as shown in the table:
Comparative example 6:
Embodiment 6 and 6 liquid-crystal composition of comparative example are irradiated by UV0.5J, and VHR data are respectively as follows: 99.8%, 99.7%.
As can be seen from the above embodiments: liquid-crystal compounds disclosed by the invention not only has biggish dielectric anisotropy, biggish
Refractive anisotrop, higher clearing point, it is often more important that there is preferable low temperature intersolubility, preferably to the steady of ultraviolet light
It is qualitative.Suitable for the TN-TFT of different box thickness, IPS, FFS liquid crystal display.
Claims (8)
1. a kind of liquid-crystal composition, which is characterized in that the liquid-crystal composition contains compound, one shown in one or more formulas I
Compound shown in compound shown in kind or a variety of formulas II and one or more formulas III
Wherein, Y1、Y3To Y13Each independently represent H or F；
Y2Indicate F；
X indicates the alkene that the fluoro-alkyl that the alkyl that F, Cl, carbon atom number are 1-6, carbon atom number are 1-6, carbon atom number are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in base；
R1Indicate that alkene, carbon that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6 are former
In the fluoro alkenyloxy group that the fluoroalkyl or carbon atom number that fluoroolefin that subnumber is 2-6, carbon atom number are 1-6 are 2-6
Any group；
R2Indicate H or carbon atom number for the alkyl of 1-3；
R3Indicate that alkene, carbon that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6 are former
Appoint in the fluoro alkenyloxy group that the fluoroalkyl or carbon atom number that fluoroolefin that subnumber is 2-6, carbon atom number are 1-6 are 2-6
One methylene is replaced by cyclopenta is formed by group；
N indicates 1 or 0；
It indicates
2. liquid-crystal composition according to claim 1, which is characterized in that compound shown in one or more formulas II is formula II
1 to one of compound shown in formula II 8 or a variety of:
3. liquid-crystal composition according to claim 1, which is characterized in that compound shown in one or more formulas III is formula III
1 to one of compound shown in formula III 12 or a variety of:
Wherein, R3Indicate the alkene that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any methylene is replaced by cyclopenta in base is formed by group.
4. liquid-crystal composition according to claim 1, which is characterized in that compound shown in one or more Formulas I is
One of compound as shown below is a variety of:
5. liquid-crystal composition according to claim 1, which is characterized in that the liquid-crystal composition also includes one or more
Compound shown in formula IV；
Wherein, R4Indicate the alkene that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6 are 2-6
The fluoro alkene oxygen that the fluoroalkyl or carbon atom number that fluoroolefin that hydrocarbon, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
Any group in base；
R5Indicate the alkene, carbon that fluoro-alkyl, carbon atom number that alkyl, carbon atom number that F, carbon atom number are 1-6 are 1-6 are 2-6
In the fluoro alkenyloxy group that the fluoroalkyl or carbon atom number that fluoroolefin that atomicity is 2-6, carbon atom number are 1-6 are 2-6
Any group；
It indicates And/orIt is one or more；
P indicates 1,2 or 3；
(F) H or F is each independently represented.
6. liquid-crystal composition according to claim 5, which is characterized in that compound shown in one or more formulas IV is
Any one or more in the compound of following structural formula:
Wherein, R4Each independently represent the fluoro-alkyl, carbon atom number that alkyl, carbon atom number that carbon atom number is 1-6 are 1-6
For the alkene of 2-6, carbon atom number be 2-6 fluoroolefin, carbon atom number be 1-6 fluoroalkyl or carbon atom number be 2-6
Fluoro alkenyloxy group in any group；
R5Each independently represent F, the fluoro-alkyl that the alkyl that carbon atom number is 1-6, carbon atom number are 1-6, carbon atom number 2-
The fluorine that the fluoroalkyl or carbon atom number that fluoroolefin that 6 alkene, carbon atom number are 2-6, carbon atom number are 1-6 are 2-6
For any group in alkenyloxy group.
7. liquid-crystal composition according to claim 5 or 6, it is characterised in that in the liquid-crystal composition, it is described a kind of or
The gross mass percent concentration of compound shown in a variety of formulas I be 1-15%, compound shown in one or more formulas II it is total
Mass percent concentration is 30-60%, and the gross mass percent concentration of compound shown in one or more formulas III is 5-
40%, the gross mass percent concentration of compound shown in one or more formulas IV is 0-30%.
8. liquid crystal display device or electro-optical display part comprising liquid-crystal composition described in claim 1-7.
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| JPH03115241A (en) * | 1989-05-13 | 1991-05-16 | Hoechst Ag | Cyclopropyl alkyl or alkenyl compound, method of their preparation and their use in liquid crystal mixture |
| DE4327748A1 (en) * | 1993-08-18 | 1995-02-23 | Merck Patent Gmbh | Cyclopropyl and cyclobutyl derivatives |
| CN104593008A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
| CN104593013A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Novel liquid crystal medium |
| CN104650923A (en) * | 2015-02-15 | 2015-05-27 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
| CN104650925A (en) * | 2015-02-15 | 2015-05-27 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium |
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2016
- 2016-05-23 CN CN201610347190.3A patent/CN106010579B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03115241A (en) * | 1989-05-13 | 1991-05-16 | Hoechst Ag | Cyclopropyl alkyl or alkenyl compound, method of their preparation and their use in liquid crystal mixture |
| DE4327748A1 (en) * | 1993-08-18 | 1995-02-23 | Merck Patent Gmbh | Cyclopropyl and cyclobutyl derivatives |
| CN104593008A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
| CN104593013A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Novel liquid crystal medium |
| CN104650923A (en) * | 2015-02-15 | 2015-05-27 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and application thereof |
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