CN105647542A - Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof - Google Patents
Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof Download PDFInfo
- Publication number
- CN105647542A CN105647542A CN201610069111.7A CN201610069111A CN105647542A CN 105647542 A CN105647542 A CN 105647542A CN 201610069111 A CN201610069111 A CN 201610069111A CN 105647542 A CN105647542 A CN 105647542A
- Authority
- CN
- China
- Prior art keywords
- another
- liquid crystalline
- independently
- crystalline cpd
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- 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
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to a liquid crystal compound containing a 1,5-indan structure shown in a general formula I and further relates to a preparation method of the compound and a composition containing the liquid crystal compound. The liquid crystal compound and the composition containing the liquid crystal compound have larger polarity, low viscosity and high response speed, have a positive significance on rapid response of a display device and can be applied to liquid crystal displays adopting TN, TFT, IPS, FFS and ADS-TFT modes.
Description
Technical field
The present invention relates to liquid crystal material field, specifically disclose a kind of contain 1,5 indane compounds liquid-crystal composition and its application in liquid crystal indicator.
Background technology
Liquid crystal material is at a certain temperature, not only has the mobility of liquid but also possess the mixture of the organic bar-shaped micromolecular compound of every opposite sex of crystal. liquid crystal display device be the every opposite sex of the optics utilizing liquid crystal material itself to have and the every opposite sex of dielectric to carry out work, be widely used at present. the characteristic utilizing liquid crystal material different and mode of operation, can be different operating mode by device layout, mainly contain following several: dynamic scattering (dynamicscattering, DS) type, electric field controls double refraction (electricallycontrolledbirefringence, ECB) type, twisted-nematic (twistednematic, TN) type, ferroelectric (ferroelectricliquidcrystal, FLC) type, guest-master (guest-host, GH) type, phase transformation (phasechange, PC) type, vertical orientation (verticalalignmentVA) type etc.
Current liquid-crystal display on the market mainly belongs to the Thin Film Transistor-LCD (ThinFilmTransistor-LquidCrystalDisplay of active matrix type, i.e. TFT-LCD), TFT-LCD has resolving power height, visual angle width, contrast gradient advantages of higher, and its energy consumption is low, volume is little, is therefore widely used.
But, still there is liquid crystal material and still there is response not soon in current TFT-LCD, voltage is low not, and the problem that electric charge maintenance rate is lower. Therefore, how researching and developing and a kind of possess good chemistry and thermostability, good electric field and the stability of electromagnetic radiation, the every opposite sex of suitable optics, the faster liquid crystal material of response speed and lower threshold voltage need most at present.
Summary of the invention
It is an object of the invention to provide a kind of liquid crystalline cpd containing 1,5 indane structural. Described liquid crystalline cpd can solve liquid crystalline cpd, has bigger dielectric anisotropy, faster time of response, rotary viscosity low.
Specifically, the liquid crystalline cpd containing 1,5-indane structural provided by the invention has structure shown in general formula I:
In described general formula I, R1Represent alkyl or the alkoxyl group with 1��15 C atom, or there is the alkene base of 2��15 C atoms; Described R1In one or more CH2Group can independently of one another by H ,-C �� C-,-C=C-,-CF2O-,-O-,-CO-O-or-O-CO-replace; Described R1In one or more H atom can be optionally substituted by halogen independently of one another;
R2Represent-H ,-F ,-Cl ,-CN ,-NCS ,-CF3��-OCF3��-OCF2Cl or there is alkyl or the alkoxyl group of 1��15 carbon atom; One or more H atom in described alkyl or alkoxyl group can be optionally substituted by halogen independently of one another;
A1��A2��A3Independent separately representative 1,4-cyclohexylidene, 1,4-phenylidene or 1,4-phenylene; 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another; 1��4 H atom in described 1,4-cyclohexylidene or 1,4-phenylidene can be replaced by fluorine atoms independently of one another, and any 1��2 CH not being connected each other2-group can be replaced by Sauerstoffatom independently of one another;
Z1��Z2��Z3Independent separately representative singly-bound ,-CH2CH2-��-(CH2)4-,-C=C-,-C �� C-,-C2F4-��-CH2CHF-��-CF2CH2-,-CF=CF-,-CH2O-��-OCH2-��-OCF2-��-CF2O-,-CO-O-or-O-CO-;
The representative 0,1,2,3 or 4 that m, n, o are independent separately, and m+n��4.
In compound of the present invention, work as R1In one or more CH2Group is by H ,-C �� C-,-C=C-,-CF2When O-,-O-,-CO-O-or-O-CO-replace, any two O atom are not directly connected each other.
In compound of the present invention, when m is greater than 1, represents and have many groups of-A1-Z1-structural unit, wherein, each A1The concrete group represented can be the same or different, and each Z1The concrete group represented can be the same or different. With managing ground, when n is greater than 1, each A2The concrete group represented can be the same or different, and each Z2The concrete group represented can be the same or different; When o is greater than 1, each A3The concrete group represented can be the same or different.
The preferred described Z of the present invention3Representative-CF2O-, the restriction of other group is identical with general formula I with replacement mode; Described liquid crystalline cpd has structure shown in general formula I-A:
The present invention further preferred described liquid crystalline cpd there is structure shown in general formula I-B:
In described general formula I-B, R1Represent the alkyl with 1��7 C atom, or there is the alkene base of 2��15 C atoms; Described R1In one or more CH2Group can independently of one another by H ,-C �� C-,-C=C-,-CF2O-,-O-,-CO-O-,-O-CO-replace; Described R1In one or more H atom can be optionally substituted by halogen independently of one another;
R2Represent-H ,-F ,-Cl ,-CN ,-NCS ,-CF3��-OCF3��-OCF2Cl or there is alkyl or the alkoxyl group of 1��15 carbon atom; One or more H atom in described alkyl or alkoxyl group can be optionally substituted by halogen independently of one another;
A2��A3Independent separately representative 1,4-cyclohexylidene, 1,4-phenylidene or 1,4-phenylene; 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another; 1��4 hydrogen atom in described 1,4-cyclohexylidene or 1,4-phenylidene can be replaced by fluorine atoms independently of one another, and any 1��2 CH not being connected each other2-group can be replaced by Sauerstoffatom independently of one another;
Z2Represent singly-bound ,-CH2CH2-��-(CH2)4-,-C=C-,-C �� C-,-C2F4-��-CH2CHF-��-CF2CH2-,-CF=CF-,-CH2O-��-OCH2-��-OCF2-��-CF2O-,-CO-O-or-O-CO-;
The representative 1 or 2 that n, o are independent separately, and n+o��3.
As a preferred embodiment of the present invention, in described general formula I-B: Z2Represent singly-bound, n=1, o=1; A2��A3All representing 1,4-phenylene, 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another.
Further preferably, described liquid crystalline cpd has structure shown in I-1��I-5:
In described general formula I-1��I-5, R1Represent-H or there is the alkyl of 1��7 carbon atom; R2Represent-H, F, Cl ,-CN, CF3��OCF3Or there is alkyl or the alkoxyl group of 1��7 carbonatoms, the one or more-CH in described alkyl or alkoxyl group2Can be replaced by-CH=CH-independently of one another.
As a preferred embodiment of the present invention, in described general formula I-B: Z2Represent singly-bound, n=2, o=1; A2��A3All representing 1,4-phenylene, 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another.
Further preferably, described liquid crystalline cpd has structure shown in I-6��I-17:
In described general formula I-6��I-17, R1Represent-H or there is the alkyl of 1��7 carbon atom; R2Represent-H, F, Cl ,-CN, CF3��OCF3Or there is alkyl or the alkoxyl group of 1��7 carbonatoms, the one or more-CH in described alkyl or alkoxyl group2Can be replaced by-CH=CH-independently of one another.
The present invention provides the preparation method of described liquid crystalline cpd simultaneously. Described general formula I, I-A are or/and in I-B, work as Z2Represent singly-bound, Z3Representative-CF2O-, m=0, n=1, o=1 and A2��A3When all representing 1,4-phenylene, or when described compound is compound shown in I-1��I-5, its synthetic route is as follows, and wherein (F) represents H or F:
Concrete steps are: taking compound 1, compound 2-1, salt of wormwood, TABA as raw material, and taking Pd (O) as catalyzer, heating reflux reaction in the mixed solvent of THF, toluene and distilled water composition, separation, purifying, to obtain final product.
Described general formula I, I-A are or/and in I-B, work as Z2Represent singly-bound, Z3Representative-CF2O-, m=0, n=2, o=1 and A2��A3When all representing 1,4-phenylene, or when described compound is compound shown in I-6��I-17, its synthetic route is as follows, and wherein (F) represents H or F:
Concrete steps are: taking compound 1, compound 2-1, salt of wormwood, TABA as raw material, and taking Pd (O) as catalyzer, heating reflux reaction in the mixed solvent of THF, toluene and distilled water composition, separation, purifying, to obtain final product.
The present invention goes back the composition of providing package containing described liquid crystalline cpd. Specifically, described liquid-crystal composition comprises one or more liquid crystalline cpds of the present invention; It is 1��40% that described liquid crystalline cpd accounts for the mass percent of described composition, it is preferable to 1��35%, it is more preferable to be 1��30%. Other compositions in described liquid-crystal composition, the technician of this area can determine according to expertise and device parameter requirements.
The application of the composition that the present invention protects described liquid crystalline cpd further and comprises described liquid crystalline cpd in the liquid-crystal display of TN, TFT, IPS, FFS, ADS-TFT pattern. Liquid crystalline cpd provided by the invention and the composition containing described liquid crystalline cpd have bigger polarity, and viscosity is low, fast response time, and the quick response for display device has positive effect.
Accompanying drawing explanation
Fig. 1 is the mass spectrum of embodiment 1 gained compound.
Fig. 2 is the mass spectrum of embodiment 2 gained compound.
Embodiment
Following examples are for illustration of the present invention, but are not used for limiting the scope of the invention.
In the present invention, the abbreviation of each performance test parameter is as follows:
�� n is optical anisotropy (589nm, 20 DEG C); Vth is threshold voltage, and light transmission rate is voltage when 10% (V); Tni is the clearing point (DEG C) of liquid-crystal composition; �� �� is dielectric anisotropy (1KHz, 25 DEG C); �� 1 is volume viscosity (mpa.s25 DEG C).
Embodiment 1
Present embodiments provide the synthetic method of a kind of liquid crystalline cpd, described by represented by reaction flow process below:
The synthetic route preparing general formula 1-1-1-5 compound is as follows:
Concrete processing step is as follows:
The synthesis of a-1:
In 10L there-necked flask, add aluminum chloride, methylene dichloride successively, open and stir, make system temperature be down to 10 DEG C and start to drip the chlorpromazine chloride that adds three. Drip finish stir 30min, start drip add chlorobenzene, drip finish be warming up to 25 DEG C reaction 4h, sampling detection without raw material; Under whipped state, reaction solution is poured in the mixed system of the concentrated hydrochloric acid prepared in advance and ice, water, leave standstill 30min, separate organic phase, aqueous phase dichloromethane extraction twice; Merging organic phase and be washed to neutrality, concentrated organic phase, obtains compound a-1;
The synthesis of a-2:
Adding the vitriol oil in 10L there-necked flask, open and stir and heating, start when system temperature rises to 105 DEG C to add a-1 in batches, react 3h after having fed in raw material, sampling detection is without raw material; Slowly being poured into by reaction solution in the frozen water mixing solutions prepared in advance, stir 30min and filter, filter cake water wash is evacuated to go out without water droplet to neutrality. Gained solid is put into baking oven 65 DEG C of normal pressures and is dried to constant weight (about needing 6h), obtains a-2.
The synthesis of a-3:
600mlTHF, 219g magnesium bits, 0.01g iodine is added successively in 10L there-necked flask, open and stir and heating, drip after 65 DEG C of backflows and add 10g initiation reaction, ethanol and liquid nitrogen cooling to 35 DEG C is used after initiation, start to drip the mixing solutions adding remaining initiator and THF, drip to finish and start to drip the mixing solutions adding 380ga-2 and 1THF, after having fed in raw material, react 2h; Reaction solution is slowly poured in the mixing solutions of 3000ml concentrated hydrochloric acid and 6kg ice, 3L water, add 3000ml toluene after stirring 30min and stir 15min, leave standstill 15min separatory, toluene merges organic phase washed with water after extracting and is washed to neutrality, leaving standstill 30min separatory, gained organic phase a-3 is for the next step.
The synthesis of a-4:
Adding a-3 organic phase, 62.7gPTSA successively in 10L there-necked flask, open and stir and heating, start clock reaction when system temperature rises to 110 DEG C, reaction 2h sampling detection is without raw material. Carry out aftertreatment, reaction solution is cooled to 25 DEG C and is washed to neutrality with water, leave standstill 30min separatory, organic addition 100g anhydrous magnesium sulfate drying, filter, filter cake 200ml toluene drip washing, merge organic phase, concentrate to obtain dark oil thing 400g; Use molecular distillation device removal tar to steam pale yellowish oil product 224.3g and it is a-4;
The synthesis of a-5:
To magnetic agitation is housed, the 2L there-necked flask of the straight type air extraction connector of glass section door adds 224.3ga-4,11.2gPd/C successively, 673ml toluene, 50ml ethanol, vacuumize displacement hydrogen three times, open and stir (oil bath temperature 20 DEG C) normal pressure timing hydrogenation reaction, sample detection reaction after reaction 7h complete; By reacting liquid filtering, filter cake 50ml toluene drip washing, merges organic phase, concentrates and distillate to without solvent, give light yellow oil 219g; Dissolve with 657ml normal heptane, cross silicagel column except tar, it may also be useful to 100ml normal heptane drip washing pillar, merge the concentrated give light yellow oil 214g of organic phase, be a-5;
The synthesis of a-6:
2.47gMg powder, 40mlTHF, 0.01g iodine is added successively in 250ml there-necked flask, open stirring, heating, when system temperature adds 1ml initiation reaction after rising to 64 DEG C of backflows, drip the mixing solutions adding 10ga-5 and 20mlTHF, finish and 20ml toluene is added system, when temperature rises to 74 DEG C of clock reactions, after reaction 10h, detection is without raw material; Gained compound is a-6;
The synthesis of a-7:
13.5ga-6 is added successively in 250ml there-necked flask, 15mlTHF (1g:1.1ml), open stirring, add liquid nitrogen cooling, start when system temperature is down to-60 DEG C to drip and add Grignard reagent,-60 DEG C of insulations 1h, about 4h rise to 0 DEG C of stopped reaction (herein without the need to detection) when temperature after dropwising; Drip in acid reaction liquid under whipped state and add 10ml hcl acidifying, being stirred in system magnesium powder has reacted PH=1, separatory uses toluene extracting twice, merge organic phase and it is washed to neutrality, organic addition 5g anhydrous magnesium sulfate drying, filters, filter cake 20ml toluene drip washing, merge organic phase, concentrate and distillate to without solvent, obtain brown oil 14.3g and be a-7;
The synthesis of a-9:
Add 40ml toluene, 15mlTHF, 5ml distilled water, 14.3ga-7,11.37ga-8,11.2g salt of wormwood, 3.0gTBAB, 0.2gPd (0) successively under stirring in 250ml there-necked flask, open and detect without raw material after reacting 4h after being heated to 80 DEG C; When system temperature be down to less than 20 DEG C in reaction solution drip add 10ml hcl acidifying, PH=3, separatory acid aqueous phase uses 50ml toluene extracting twice, merge organic phase and it is washed to neutral standing 30min separatory, organic phase 5g anhydrous magnesium sulfate drying, filters, filter cake 20ml toluene drip washing, merging organic phase concentrates and distillates to without solvent, obtains brown oil 15.4g; Use molecular distillation device to steam front-end volatiles residue and do not steam substrate 12g. Crossing post except tar, with the new normal heptane room-temperature dissolution of 240ml, dress silicagel column, with the new normal heptane drip washing of 50ml, with ethanol and normal heptane heat of solution recrystallization, filters to obtain filter cake 6.1g (weight in wet base), and it is compound a-9 that drying obtains white solid.
Can synthesize according to above method and obtain compoundIts mass spectrum is as shown in Figure 1.
Embodiment 2
The synthetic route preparing general formula 1-6-1-17 compound is as follows:
Corresponding concrete steps are with embodiment 1.
Can synthesize according to above method and obtain compoundIts mass spectrum is as shown in Figure 2.
Embodiment 3
Present embodiments providing a kind of liquid-crystal composition, its composition is as shown in table 1.
Table 1: liquid-crystal composition forms
Embodiment 4
Present embodiments providing a kind of liquid-crystal composition, its composition is as shown in table 2.
Table 2: liquid-crystal composition forms
Embodiment 5
Present embodiments providing a kind of liquid-crystal composition, its composition is as shown in table 3.
Table 3: liquid-crystal composition forms
Embodiment 6
Present embodiments providing a kind of liquid-crystal composition, its composition is as shown in table 4.
Table 4: liquid-crystal composition forms
Embodiment 7
Present embodiments providing a kind of liquid-crystal composition, its composition is as shown in table 5.
Table 5: liquid-crystal composition forms
Comparative example 1
The composition of liquid-crystal composition is as shown in table 6.
Table 6: liquid-crystal composition forms
Comparative example 2
The composition of liquid-crystal composition is as shown in table 7.
Table 7: liquid-crystal composition forms
Being detected by the liquid crystal combination physical performance that above each embodiment and comparative example provide, detected result is as shown in table 8.
Table 8: liquid crystal combination physical performance
Tni | ��n | ���� | Vth | ��1 | |
Embodiment 3 | 82.5 | 0.1025 | 4.98 | 2.32 | 60.5 |
Embodiment 4 | 80.7 | 0.1044 | 5.12 | 2.20 | 58 |
Embodiment 5 | 84.5 | 0.1030 | 5.24 | 2.10 | 54 |
Embodiment 6 | 82.3 | 0.1067 | 5.06 | 2.28 | 53.5 |
Embodiment 7 | 81.7 | 0.1058 | 4.98 | 2.30 | 56.4 |
Comparative example 1 | 82.3 | 0.1074 | 4.2 | 2.96 | 67.8 |
Comparative example 2 | 83.6 | 0.995 | 3.75 | 3.24 | 72 |
By above result it will be seen that compared with comparative example 1,2, the liquid-crystal composition that various embodiments of the present invention provide has the every opposite sex of applicable dielectric, property and degree of birefringence, and lower threshold voltage, faster response speed, and good low temperature storage stability. Being applied in liquid-crystal display by above-mentioned liquid-crystal composition, especially in the indicating meter of TFT-LCD pattern, the optics of its excellence and electric property can obviously improve its display effect.
Although, above with general explanation, embodiment and test, the present invention is described in detail, but on basis of the present invention, it is possible to it being made some modifications or improvements, this will be apparent to those skilled in the art. Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (9)
1. one kind contains the liquid crystalline cpd of 1,5-indane structural, it is characterised in that, described liquid crystalline cpd has structure shown in general formula I:
In described general formula I, R1Represent alkyl or the alkoxyl group with 1��15 C atom, or there is the alkene base of 2��15 C atoms; Described R1In one or more CH2Group can independently of one another by H ,-C �� C-,-C=C-,-CF2O-,-O-,-CO-O-or-O-CO-replace; Described R1In one or more H atom can be optionally substituted by halogen independently of one another;
R2Represent-H ,-F ,-Cl ,-CN ,-NCS ,-CF3��-OCF3��-OCF2Cl or there is alkyl or the alkoxyl group of 1��15 carbon atom; One or more H atom in described alkyl or alkoxyl group can be optionally substituted by halogen independently of one another;
A1��A2��A3Independent separately representative 1,4-cyclohexylidene, 1,4-phenylidene or 1,4-phenylene; 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another; 1��4 H atom in described 1,4-cyclohexylidene or 1,4-phenylidene can be replaced by fluorine atoms independently of one another, and any 1��2 CH not being connected each other2-group can be replaced by Sauerstoffatom independently of one another;
Z1��Z2��Z3Independent separately representative singly-bound ,-CH2CH2-��-(CH2)4-,-C=C-,-C �� C-,-C2F4-��-CH2CHF-��-CF2CH2-,-CF=CF-,-CH2O-��-OCH2-��-OCF2-��-CF2O-,-CO-O-or-O-CO-;
The representative 0,1,2,3 or 4 that m, n, o are independent separately, and m+n��4.
2. liquid crystalline cpd according to claim 1, it is characterised in that, Z3Representative-CF2O-, described liquid crystalline cpd has structure shown in general formula I-A:
3. liquid crystalline cpd according to claim 2, it is characterised in that, Z3Representative-CF2O-, m=0, described liquid crystalline cpd has structure shown in general formula I-B:
In described general formula I-B, R1Represent the alkyl with 1��7 C atom, or there is the alkene base of 2��15 C atoms; Described R1In one or more CH2Group can independently of one another by H ,-C �� C-,-C=C-,-CF2O-,-O-,-CO-O-,-O-CO-replace; Described R1In one or more H atom can be optionally substituted by halogen independently of one another;
R2Represent-H ,-F ,-Cl ,-CN ,-NCS ,-CF3��-OCF3��-OCF2Cl or there is alkyl or the alkoxyl group of 1��15 carbon atom; One or more H atom in described alkyl or alkoxyl group can be optionally substituted by halogen independently of one another;
A2��A3Independent separately representative 1,4-cyclohexylidene, 1,4-phenylidene or 1,4-phenylene; 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another; 1��4 hydrogen atom in described 1,4-cyclohexylidene or 1,4-phenylidene can be replaced by fluorine atoms independently of one another, and any 1��2 CH not being connected each other2-group can be replaced by Sauerstoffatom independently of one another;
Z2Represent singly-bound ,-CH2CH2-��-(CH2)4-,-C=C-,-C �� C-,-C2F4-��-CH2CHF-��-CF2CH2-,-CF=CF-,-CH2O-��-OCH2-��-OCF2-��-CF2O-,-CO-O-or-O-CO-;
The representative 1 or 2 that n, o are independent separately, and n+o��3.
4. liquid crystalline cpd according to claim 3, it is characterised in that, in described general formula I-B: Z2Represent singly-bound, n=1, o=1; A2��A3All representing 1,4-phenylene, 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another;
Preferably, described liquid crystalline cpd has structure shown in I-1��I-5:
In described general formula I-1��I-5, R1Represent-H or there is the alkyl of 1��7 carbon atom; R2Represent-H, F, Cl ,-CN, CF3��OCF3Or there is alkyl or the alkoxyl group of 1��7 carbonatoms, the one or more-CH in described alkyl or alkoxyl group2Can be replaced by-CH=CH-independently of one another.
5. liquid crystalline cpd according to claim 3, it is characterised in that, in described general formula I-B: Z2Represent singly-bound, n=2, o=1; A2��A3All representing 1,4-phenylene, 1��4 hydrogen atom in described 1,4-phenylene can be replaced by fluorine atoms independently of one another;
Preferably, described liquid crystalline cpd has structure shown in I-6��I-17:
In described general formula I-6��I-17, R1Represent-H or there is the alkyl of 1��7 carbon atom; R2Represent-H, F, Cl ,-CN, CF3��OCF3Or there is alkyl or the alkoxyl group of 1��7 carbonatoms, the one or more-CH in described alkyl or alkoxyl group2Can be replaced by-CH=CH-independently of one another.
6. the preparation method of liquid crystalline cpd described in claim 3��5 any one, it is characterised in that, in described general formula I-B, n=1 or 2, o=1, Z2Represent singly-bound, A2��A3All represent 1,4-phenylene;
The synthetic route of described compound is as follows:
In described general formula b, Y represents:
Wherein, (F) represents H or F; In compound c, Y is corresponding with compound b with the group that (F) represents;
The concrete steps of described compou nd synthesis are: taking compound a, compound b, salt of wormwood, TABA as raw material, and taking Pd (O) as catalyzer, heating reflux reaction in the mixed solvent of THF, toluene and distilled water composition, separation, purifying, to obtain final product.
7. a liquid-crystal composition, it is characterised in that, comprise liquid crystalline cpd described in Claims 1 to 5 any one.
8. liquid-crystal composition according to claim 7, it is characterised in that, it is 1��40% that described liquid crystalline cpd accounts for the mass percent of described composition, it is preferable to 1��35%, it is more preferable to be 1��30%.
9. application in TN, TFT, IPS, FFS, ADS-TFT mode LCD of liquid crystalline cpd described in Claims 1 to 5 any one or liquid-crystal composition described in claim 7 or 8.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610069111.7A CN105647542A (en) | 2016-02-01 | 2016-02-01 | Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610069111.7A CN105647542A (en) | 2016-02-01 | 2016-02-01 | Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105647542A true CN105647542A (en) | 2016-06-08 |
Family
ID=56488956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610069111.7A Pending CN105647542A (en) | 2016-02-01 | 2016-02-01 | Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105647542A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111154498A (en) * | 2020-01-19 | 2020-05-15 | 西安瑞联新材料股份有限公司 | Preparation method of liquid crystal compound containing 1, 5-indan and difluoromethoxy bridge |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0647695A1 (en) * | 1993-09-29 | 1995-04-12 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device and liquid crystal apparatus using same |
CN102477305A (en) * | 2010-11-25 | 2012-05-30 | 达兴材料股份有限公司 | Liquid crystal compound and liquid crystal mixture |
CN102634346A (en) * | 2012-03-21 | 2012-08-15 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and application thereof as well as liquid crystal display comprising liquid crystal composition |
CN102757794A (en) * | 2012-07-13 | 2012-10-31 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and display device thereof |
CN102795974A (en) * | 2012-07-31 | 2012-11-28 | 江苏和成显示科技股份有限公司 | Liquid crystal medium and liquid crystal composition |
CN102899054A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with improved liquid crystal low-temperature smectic phase |
CN102911673A (en) * | 2012-10-13 | 2013-02-06 | 江苏和成显示科技股份有限公司 | Liquid crystal composite and electro-optical display device comprising same |
CN103087724A (en) * | 2013-01-08 | 2013-05-08 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device comprising same |
CN103131426A (en) * | 2011-11-25 | 2013-06-05 | 达兴材料股份有限公司 | Liquid crystal compound and liquid crystal medium |
KR20160006844A (en) * | 2014-07-09 | 2016-01-20 | 주식회사 동진쎄미켐 | Noble Liquid crystal compound comprising Indane derivatives and Liquid crystal Composition using the same |
-
2016
- 2016-02-01 CN CN201610069111.7A patent/CN105647542A/en active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0647695A1 (en) * | 1993-09-29 | 1995-04-12 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device and liquid crystal apparatus using same |
CN102477305A (en) * | 2010-11-25 | 2012-05-30 | 达兴材料股份有限公司 | Liquid crystal compound and liquid crystal mixture |
CN103131426A (en) * | 2011-11-25 | 2013-06-05 | 达兴材料股份有限公司 | Liquid crystal compound and liquid crystal medium |
CN102634346A (en) * | 2012-03-21 | 2012-08-15 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and application thereof as well as liquid crystal display comprising liquid crystal composition |
CN102757794A (en) * | 2012-07-13 | 2012-10-31 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and display device thereof |
CN102795974A (en) * | 2012-07-31 | 2012-11-28 | 江苏和成显示科技股份有限公司 | Liquid crystal medium and liquid crystal composition |
CN102899054A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with improved liquid crystal low-temperature smectic phase |
CN102911673A (en) * | 2012-10-13 | 2013-02-06 | 江苏和成显示科技股份有限公司 | Liquid crystal composite and electro-optical display device comprising same |
CN103087724A (en) * | 2013-01-08 | 2013-05-08 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device comprising same |
KR20160006844A (en) * | 2014-07-09 | 2016-01-20 | 주식회사 동진쎄미켐 | Noble Liquid crystal compound comprising Indane derivatives and Liquid crystal Composition using the same |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111154498A (en) * | 2020-01-19 | 2020-05-15 | 西安瑞联新材料股份有限公司 | Preparation method of liquid crystal compound containing 1, 5-indan and difluoromethoxy bridge |
CN111154498B (en) * | 2020-01-19 | 2021-10-22 | 西安瑞联新材料股份有限公司 | Preparation method of liquid crystal compound containing 1, 5-indan and difluoromethoxy bridge |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102964226B (en) | Liquid crystal compound containing cyclobutyl and difluoromethylenedioxy connecting radical as well as preparation method and application thereof | |
CN102924243B (en) | Liquid crystal compound containing cyclopentyl and difluorometheneoxy linking group, preparation method and applications thereof | |
CN103254903B (en) | Liquid crystalline cpd containing difluoro methylene key bridge and preparation method thereof and composition | |
CN103602337B (en) | Cyclohexane derivatives, preparation method thereof and applications thereof | |
CN103467253B (en) | Cycloheptane derivative and preparation method thereof and application | |
CN103204832A (en) | Compound containing tetrahydrofuran, preparation method and application | |
CN105294526A (en) | High-birefringence liquid crystal compound, preparing method and composition of high-birefringence liquid crystal compound | |
CN103058886B (en) | Poly-fluorine poly-cyanogen liquid crystal compound as well as preparation method and application thereof | |
CN103772335B (en) | A kind of liquid crystalline cpd and liquid-crystal composition thereof containing five fluorine propylene and pyranoid ring | |
CN104496742A (en) | Liquid crystal compound, liquid crystal composition and application of liquid crystal compound and liquid crystal composition | |
CN106278812A (en) | A kind of liquid-crystal compounds with negative dielectric anisotropic and combinations thereof thing and its application | |
CN105131971A (en) | Liquid crystal compound with 2-fluorophenyl group and difluoro methyleneoxy group and preparing method and application thereof | |
CN105130767A (en) | Liquid crystal compound containing methylbenzene and difluoro methyleneoxy linking group and preparing method and application thereof | |
CN102408896B (en) | Liquid crystal compound and liquid crystal mixture | |
CN106336350A (en) | Fluorine-containing dinaphthylacetylene liquid crystal compound, preparation method and application thereof | |
CN102675040B (en) | Poly-fluorinated quaterphenyl liquid crystal compound and preparation method and application thereof | |
CN104593000A (en) | Liquid crystal compound and liquid crystal display element comprising compound | |
CN105647542A (en) | Liquid crystal compound containing 1,5-indan structure and preparation method and application thereof | |
CN103242855B (en) | Liquid crystal compound containing cyclobutyl and difluorometheneoxy | |
CN103242854B (en) | Fluorine-containing liquid crystal compound | |
CN103534335B (en) | Liquid crystal compound | |
CN102675041B (en) | Method for preparing trifluoromethyl-benzene-containing liquid crystals | |
CN103087037B (en) | Liquid crystalline cpd containing the sub-methoxyl group linking group of DOX and difluoro and preparation method thereof and application | |
CN103788039B (en) | Liquid-crystal compounds containing oxinane difluoromethylenedioconnecting linking group and preparation method and application | |
CN103880810A (en) | Oxepane derivative |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160608 |
|
RJ01 | Rejection of invention patent application after publication |