CN101973878B - Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof - Google Patents

Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof Download PDF

Info

Publication number
CN101973878B
CN101973878B CN 201010293278 CN201010293278A CN101973878B CN 101973878 B CN101973878 B CN 101973878B CN 201010293278 CN201010293278 CN 201010293278 CN 201010293278 A CN201010293278 A CN 201010293278A CN 101973878 B CN101973878 B CN 101973878B
Authority
CN
China
Prior art keywords
formula
liquid crystal
compound
reaction
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.)
Active
Application number
CN 201010293278
Other languages
Chinese (zh)
Other versions
CN101973878A (en
Inventor
梁晓
唐洪
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shenzhen Dalton Electronic Materials Co ltd
Original Assignee
Tsinghua University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tsinghua University filed Critical Tsinghua University
Priority to CN 201010293278 priority Critical patent/CN101973878B/en
Publication of CN101973878A publication Critical patent/CN101973878A/en
Application granted granted Critical
Publication of CN101973878B publication Critical patent/CN101973878B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a liquid crystal compound containing dicyclohexyl as well as a preparation method and application thereof. The structural general formula of the liquid crystal compound is shown in the formula I, wherein n is an integer from 1 to 5, and m is an integer from 2 to 6; and -(CH2)m- and -CnH2n+1 are linear chain alkyl groups. The dicyclohexane macromolecular liquid crystal compound intermediate provided by the invention comprises a dicyclohexyl rigid frame and double-bond groups which can be polymerized to form a flexible polymer repeating unit. The frame does not comprise a pi-electron system of benzene rings, the charge density distribution is reduced, the polarization is weakened, and cyclohexane rings are mutually stacked in a staggered mode to form compact packing, thus the clearing point of the liquid crystal phase can be improved. Compared with the aromatic ring liquid crystal with the similar structure, the liquid crystal of the invention has lower viscosity, better stability and hardly andy ultraviolet absorption. The liquid crystal compound of the invention is a good liquid crystal function material and can be used for many fields of building materials, anti-counterfeiting materials, optical communication materials, new optical materials and the like. Formula I is shown in the specification.

Description

A kind of liquid crystalline cpd that contains dicyclohexyl and preparation method thereof and application
Technical field
The present invention relates to a kind of liquid crystalline cpd that contains dicyclohexyl and preparation method thereof and application.
Background technology
1888, Austrian scientist F.Reinitzer synthesized a kind of special organic compound cholesteryl benzoate, when its solid crystals is heated to 145 ℃, just is melt into liquid, and is only muddy, and is transparent during all pure materials fusings.If when continuing to be heated to 175 ℃, as if it is again fusing, becomes as clear as crystal liquid.This clarified liq cools off a little, and muddiness is appeared again again existing.Roentgen Lehmann is defined as the crystalline state fluid with it after this material is furtherd investigate, and crystal (Fliessende kristalle), namely said liquid crystal today (liquid crystal) flow.Development through decades, especially nearly two during the last ten years, the liquid crystal theory is constantly perfect, and the liquid crystal science has also obtained many important development, and research field spreads all over the every subjects such as liquid crystal optics, molecular physics, Liquid Crystal, liquid crystal molecule spectrum, Liquid Crystalline Biomacromolecules.
High molecule liquid crystal is to have a base polymer that is similar to the low molecular weight liquid crystal ordered structure, and they present the distinctive flowability of liquid crystal and anisotropy in molten state or solution.Find in to the molten research process that causes the type Liquid Crystalline Polymeric Materials, some high molecule liquid crystal demonstrates the function of biological tissue in specific solvent, and this is for synthesized membrane and make it to have biological activity possibility is provided; In the research process to the thermotropic Liquid Crystalline Polymeric Materials, find, because the existence of liquid crystal phase in the polymkeric substance, the various synthon that can obtain superstrength, ultra high modulus, thermostability are high and mechanical property is good, this has caused the huge interest of people to macromolecular compound liquid crystal state structure more.Along with to the deepening continuously of such investigation of materials, the matrix material that is obtained by the liquid crystal state polymkeric substance has been widely used in a plurality of fields such as aerospace material, material of construction, anti-fake material, optical communication material and novel optical material.
Liquid Crystalline Polymeric Materials is divided into compound three classes of main chain polymer, side chain polymer and main chain side chain usually according to its structure.The constructional feature of main chain polymer liquid crystal is that polymer repeat unit is the rigid backbone with mesomorphic phase structure, as shown in Figure 1; The constructional feature of side chain high molecule liquid crystal is that the repeating unit of polymkeric substance is flexible, has the rigid backbone of mesomorphic phase structure on the side chain of molecule, as shown in Figure 2; The constructional feature of main chain side chain composite polymer liquid crystal is all to have the rigid backbone with mesomorphic phase structure on the side chain of polymer repeat unit and polymer molecule, as shown in Figure 3.
In the application process of liquid crystal, in order to satisfy all-environment requirement, various Secretaries have been proposed liquid crystal material.Early stage high molecule liquid crystal has in the rigid backbone of mesomorphic phase structure and usually all contains benzene ring structure, contains a large conjugated system in the benzene ring structure, and UV-light is had stronger absorption, has therefore affected the stability of material; Along with going deep into of research, cyclohexane ring is more and more introduced in the rigid backbone, and behind the phenyl ring that replaces with cyclohexane ring in the liquid crystal, the π-electron system reduces or disappears, charge density distribution reduces, polarization weakens, and cyclohexane ring is interlaced stacks, and forms tightly packed, cause the liquid crystal clearing point to increase, the aromatic ring class mesomorphic phase specific viscosity of such liquid crystal and structural similitude is lower, and does not almost have uv-absorbing, and stability is better.
Summary of the invention
The purpose of this invention is to provide a kind of liquid crystalline cpd that contains dicyclohexyl and preparation method thereof.
Liquid crystalline cpd provided by the present invention, its general structure are suc as formula the compound shown in (I):
Figure BSA00000285329500021
(formula I)
Among the formula I, n is the integer of 1-5, and m is the integer of 2-6;-(CH 2) m-and-C nH 2n+1Be straight chained alkyl.
The preparation method of formula I compound provided by the present invention comprises the steps:
1) in inert atmosphere, alkyl dicyclohexyl shown in formula II alcohol and the chloro alkyl alcohol shown in the formula III or bromo alkyl alcohol are reacted under the condition that sodium hydride (NaH) exists, obtain the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane;
2) in inert atmosphere, the acrylate chloride shown in the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane and the formula V is reacted, obtain the compound shown in the formula I;
Figure BSA00000285329500022
(formula II) (formula III)
Figure BSA00000285329500023
(formula IV) (formula V)
In the described structural formula, n is the integer of 1-5, and m is the integer of 2-6;-(CH 2) m-and-C nH 2n+1Be straight chained alkyl.
Aforesaid method step 1) reaction described in is carried out in organic solvent, and described organic solvent specifically can be tetrahydrofuran (THF), ether or dioxane.
Step 1) in the described reaction, the alkyl dicyclohexyl alcohol shown in the formula II can be (1-2) with the mol ratio of chloro alkyl alcohol shown in the formula III or bromo alkyl alcohol: (1-2), such as 1: 1,1: 1.5,1: 2,1.5: 1 or 2: 1; The temperature of reaction of described reaction is 50-60 ℃, and the reaction times is 1-24 hour.
The method also can be included in step 2) front to step 1) the formula IV compound that obtains carries out the step of purifying, method is as follows: step 1) described in after reaction finishes, in the reaction solution that contains formula IV compound, add entry, the separated and collected organic solvent layer, washing, dried over sodium sulfate is steamed except described organic solvent, the solid that obtains sherwood oil recrystallization namely obtains the formula IV compound behind the purifying.
Aforesaid method step 2) reaction described in is also carried out in organic solvent, and described organic solvent is benzene or toluene.
Step 2) in the described reaction, the mol ratio of the acrylate chloride shown in the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane and the formula V can be 1: (1-2), such as 1: 1,1: 1.5,1: 2; The temperature of reaction of described reaction is 60-90 ℃, and the reaction times is 3-10 hour.
Method of the present invention also can comprise the step of formula I compound being carried out purifying, method is as follows: step 2) described in after reaction finishes, in the reaction solution that contains formula I compound, add entry, the separated and collected organic solvent layer, washing, dried over sodium sulfate is steamed except described organic solvent, the solid that obtains sherwood oil recrystallization namely obtains the formula I compound behind the purifying.
Inert atmosphere is nitrogen atmosphere described in the inventive method.
Another object of the present invention provides the purposes of compound shown in the formula (I).
The purposes of compound shown in the formula provided by the present invention (I) is that this compound is as the application of liquid crystal material.
In addition, can also formula (I) compound be monomer (or performed polymer) preparation high molecule liquid crystal compound.
Dicyclic hexane high molecule liquid crystal compound intermediate provided by the invention, have the two key groups and the dicyclohexyl rigid backbone that can polymerization form the flexible polymer repeating unit, this skeleton is without the π-electron system of phenyl ring, charge density distribution reduces, polarization weakens, and cyclohexane ring is interlaced to be stacked, form tightly packed, can improve the clearing point of mesomorphic phase, the aromatic ring class mesomorphic phase specific viscosity of such liquid crystal and structural similitude is lower, and does not almost have uv-absorbing, and stability is better, be a kind of good liquid crystal functional materials, can be used for material of construction, anti-fake material, a plurality of fields such as optical communication material and novel optical material.
Description of drawings
Fig. 1 is the structure iron of main chain polymer liquid crystal.
Fig. 2 is the structure iron of side chain high molecule liquid crystal.
Fig. 3 is the structure iron of main chain side chain composite polymer liquid crystal.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Experimental technique among the following embodiment if no special instructions, is ordinary method.Used test materials if no special instructions, is and purchases available from conventional reagent shop.
The preparation of embodiment 1,2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate (m=2 among the formula I, the compound of n=1)
1) preparation of 4-hydroxyl-oxyethyl group-4 '-methyl-bis cyclohexane
In the 250ML there-necked flask; under the nitrogen protection; 2.4 gram (0.1mol) sodium hydrides are dissolved in the 100ml tetrahydrofuran (THF) (THF); again methyl bicycle hexyl alcohol 19.6 grams (0.1mol) are added in the reaction flask, stirred 0.5 hour, drip 12.1 gram (0.15mol) 2-chloro-ethanol; dropwise and stirred 1 hour; refluxed 6 hours at 60 ℃, after the cooling, add 50ml water; isolate the THF layer; washing THF layer, dried over sodium sulfate steams THF; the solid that obtains 50ml sherwood oil recrystallization; obtain white solid 14.9 grams, be 4-hydroxyl-oxyethyl group-4 '-methyl-bis cyclohexane, yield 62%.
2) preparation of 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate
In the 250ML there-necked flask; under the nitrogen protection; adding above-mentioned 24 gram (0.1mol) 4-hydroxyl-oxyethyl group-4 '-methyl-bis cyclohexanes adds in the reaction flask and 100ml benzene; stirred 0.5 hour; drip 9.05 gram (0.1mol) acrylate chlorides, dropwise, refluxed 4 hours at 80 ℃; after the cooling; add 50ml water, isolate the benzene layer, washing; dried over sodium sulfate; steam benzene, the solid that obtains obtains white solid 26.5 grams with 100ml sherwood oil recrystallization; be 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate, yield 90%.
This product structure appraising datum is as follows:
IR:3090,3025,2975,2960,2920,2860,,1730,1635,1470,,1300,1150,990,910,725;
MS:294(M+),240,223,196,179,165
HNMR:0.96(3H),1.27~1.70(19H),2.79(1H),3.65(2H),4.27(2H),5.80(1H),6.05(1H),6.43(1H)
By the said determination result as can be known, this compound structure is correct.
The DSC data are as follows:
DSC:T C-N(fusing point) 41 ℃
Viscosity: 23mm 2S
Measure dielectric anisotropy (Δ ε) and the specific refractory power anisotropy (Δ n) of 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate liquid crystalline cpd.
Take TEB110 (being purchased from Shijiazhuang Yongshenghuaqing Liquid Crystal Co., Ltd) as the parent mixed liquid crystal, 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate liquid crystalline cpd is pressed 5% (w/w, mass ratio) is dissolved among the TEB 110, under the condition of 20 ℃ and 1KHz, test the ε of 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate liquid crystalline cpd with capacitance method || and ε ⊥, and calculate the Δ ε of this liquid crystal compound, thereby calculate the ε of pure 2-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate liquid crystalline cpd || and ε ⊥, and calculate the Δ ε of this liquid crystalline cpd, test result is listed in the table 1.
Utilize Abbe refractometer, measure ne and the no of above-mentioned liquid crystal compound, and calculate the Δ ε of this liquid crystal compound.Thereby calculate ne and the no of this pure liquid crystalline cpd, and calculate the Δ n of this liquid crystalline cpd, test result is listed in the table 1.
Wherein, the method for calculation of Δ ε and Δ n are as follows:
The parameter ε of parent liquid crystal TEB110 (B) || (B), ε ⊥ (B) and Δ ε (B) see Table 1, liquid crystalline cpd (A) is dissolved among the parent liquid crystal TEB110 by 5% (W/W), under the condition of 20 ℃ and 1KHz, test the ε of this liquid crystal compound with capacitance method || and ε ⊥, and calculate the Δ ε of this liquid crystal compound, Δ ε=ε ||-ε ⊥.
According to the additivity of liquid crystalline cpd dielectric anisotropy, calculate ε || (A), ε ⊥ (A), Δ ε (A)
ε||=ε||(A)×5%+ε||(B)×95% ε||(A)=[ε||-ε||(B)×95%]/5%
ε⊥=ε⊥(A)×5%+ε⊥(B)×95% ε⊥(A)=[ε⊥×5%+ε⊥(B)×95%]/5%
Δε(A)=ε||(A)-ε⊥(A)
The parameter ne (B) of parent liquid crystal TEB110 (B), no (B) and Δ n (B) see Table 1, liquid crystalline cpd (A) is dissolved among the parent liquid crystal TEB110 by 5% (W/W), utilize Abbe refractometer to measure ne, the no of liquid crystal compound, and calculate the Δ n of this liquid crystal compound, Δ n=ne-no.
According to the anisotropic additivity of liquid crystalline cpd specific refractory power, calculate ne (A), no (A) and Δ n (A)
ne=ne(A)×5%+ne(B)×95% ne(A)=[ne-ne(B)×95%]/5%
no=no(A)×5%+no(B)×95% no(A)=[no×5%+no(B)×95%]/5%
Δn(A)=ne(A)-no(A)
The measurement result of table 12-((4 '-methyl-dicyclohexyl)-4-oxygen base) ethyl-acrylate liquid crystalline cpd
ne no Δn ε|| ε⊥ Δε
TEB110(B) 1.640 1.503 0.137 14.6 6.0 8.6
Mixture 1.635 1.502 0.132 14.11 5.86 8.25
A 1.541 1.499 0.042 4.76 3.18 1.58
The preparation of embodiment 2,3-((4 '-methyl-dicyclohexyl)-4-oxygen base) propyl group-acrylate (m=3 among the formula I, the compound of n=1)
1) preparation of 4-hydroxyl-propoxy--4 '-methyl-bis cyclohexane
In the 250ML there-necked flask; under the nitrogen protection; 2.4 gram (0.1mol) sodium hydrides are dissolved in the 100ml ether; again methyl bicycle hexyl alcohol 19.6 grams (0.1mol) are added in the reaction flask, stirred 0.5 hour, drip 25 gram (0.2mol) 3-bromo-propyl alcohol; dropwise and stirred 1 hour; refluxed 6 hours at 55 ℃, after the cooling, add 50ml water; isolate the THF layer; washing, dried over sodium sulfate steams THF; the solid that obtains 50ml sherwood oil recrystallization; obtain 19.2 gram white solids, be 4-hydroxyl-propoxy--4 '-methyl-bis cyclohexane, yield 75%.
2) preparation of 3-((4 '-methyl-dicyclohexyl)-4-oxygen base) propyl group-acrylate
In the 250ML there-necked flask; under the nitrogen protection; add above-mentioned 25.6 gram (0.1mol) 4-hydroxyl-propoxy--4 '-methyl-bis cyclohexane and 100ml toluene; stirred 1 hour; drip 13.58 gram (0.15mol) acrylate chlorides, dropwise and stirred 5 hours, refluxed 4 hours at 90 ℃; after the cooling; add 100ml water, isolate toluene layer, washing; dried over sodium sulfate; steam toluene, the solid that obtains obtains white solid 29.3 grams with 100lL sherwood oil recrystallization; be 3-((4 '-methyl-dicyclohexyl)-4-oxygen base) propyl group-acrylate, yield 95%.
This product structure appraising datum is as follows:
IR:3090,3020,2980,2960,2920,2860,,1735,1635,1470,,1300,1150,990,900
MS:308(M+),255,237,196,179,165;
HNMR:0.97(3H),1.27~1.70(19H),1.86(2H),2.79(1H),3.37(2H),4.20(2H),5.80(1H),6.05(1H),6.43(1H)
By the said determination result as can be known, this compound structure is correct.
The DSC data are as follows:
DSC:T C-N(fusing point) 46 ℃
Viscosity: 25mm 2S
Adopt Δ n and the Δ ε of method mensuration 3-((4 '-methyl-the dicyclohexyl)-4-oxygen base) propyl group-acrylate liquid crystalline cpd identical with embodiment 1.Data are as follows: Δ n:0.038, Δ ε: 1.39.

Claims (10)

1. general structure is suc as formula the compound shown in (I):
Figure FSB00001026512500011
(formula I)
Wherein, n is the integer of 1-5, and m is the integer of 2-6;-(CH 2) m-and-C nH 2n+1Be straight chained alkyl.
2. compound according to claim 1, it is characterized in that: the compound shown in the described formula (I) is following 1) or 2) in compound:
1) m=2 in the formula (I), the compound of n=1;
2) m=3 in the formula (I), the compound of n=1.
3. prepare the method for the described compound of claim 1, comprise the steps:
1) in inert atmosphere, the alcohol of the alkyl dicyclohexyl shown in the formula II and the chloro alkyl alcohol shown in the formula III or bromo alkyl alcohol are reacted under the condition that sodium hydride exists, obtain the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane;
2) in inert atmosphere, the acrylate chloride shown in the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane and the formula V is reacted, obtain the compound shown in the formula I;
Figure FSB00001026512500012
(formula II) (formula III)
(formula IV) (formula V)
Among described formula II, formula III and the formula IV, n is the integer of 1-5, and m is the integer of 2-6;-(CH 2) m-and-C nH 2n+1Be straight chained alkyl.
4. method according to claim 3 is characterized in that: step 1) in the described reaction, the alkyl dicyclohexyl alcohol shown in the formula II is (1-2) with the mol ratio of chloro alkyl alcohol shown in the formula III or bromo alkyl alcohol: (1-2); The temperature of reaction of described reaction is 50-60 ℃, and the reaction times is 1-24 hour;
Step 1) reaction described in is carried out in organic solvent, and described organic solvent is tetrahydrofuran (THF), ether or dioxane; Described inert atmosphere is nitrogen atmosphere.
5. method according to claim 4, it is characterized in that: described method also is included in step 2) front to step 1) the formula IV compound that obtains carries out the step of purifying, method is as follows: step 1) described in after reaction finishes, in the reaction solution that contains formula IV compound, add entry, separated and collected organic solvent layer, washing, dried over sodium sulfate, steam except described organic solvent, the solid that obtains sherwood oil recrystallization namely obtains the formula IV compound behind the purifying.
6. each described method is characterized in that: step 2 according to claim 3-5) in the described reaction, the mol ratio of the acrylate chloride shown in the 4-hydroxyl-alkoxyl group-4 ' shown in the formula IV-alkyl-bis cyclohexane and the formula V is 1:(1-2); The temperature of reaction of described reaction is 60-90 ℃, and the reaction times is 3-10 hour.
7. method according to claim 6 is characterized in that: step 2) described reaction carries out in organic solvent, and described organic solvent is benzene or toluene; Described inert atmosphere is nitrogen atmosphere.
8. method according to claim 7, it is characterized in that: described method also comprises step 2) the formula I compound that obtains carries out the step of purifying, method is as follows: step 2) described in after reaction finishes, in the reaction solution that contains formula I compound, add entry, separated and collected organic solvent layer, washing, dried over sodium sulfate, steam except described organic solvent, the solid that obtains sherwood oil recrystallization namely obtains the formula I compound behind the purifying.
9. claim 1 or 2 described compounds are as the application of liquid crystal material.
10. claim 1 or the 2 described compounds application in preparation high molecule liquid crystal compound.
CN 201010293278 2010-09-27 2010-09-27 Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof Active CN101973878B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201010293278 CN101973878B (en) 2010-09-27 2010-09-27 Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201010293278 CN101973878B (en) 2010-09-27 2010-09-27 Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN101973878A CN101973878A (en) 2011-02-16
CN101973878B true CN101973878B (en) 2013-04-10

Family

ID=43573796

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201010293278 Active CN101973878B (en) 2010-09-27 2010-09-27 Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN101973878B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8372307B2 (en) * 2006-11-24 2013-02-12 Merck Patent Gmbh Cyclohexylene reactive mesogens and their applications

Also Published As

Publication number Publication date
CN101973878A (en) 2011-02-16

Similar Documents

Publication Publication Date Title
Lee et al. The effect of mesogenic length on the curing behavior and properties of liquid crystalline epoxy resins
KR20020070304A (en) Polymerizable liquid crystalline dioxetanes, their preparation and use
CN112143508B (en) Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and liquid crystal display device
JP2004002373A (en) Maleimide derivative and its polymer
CN106699710A (en) Laterally tetrafluoro-substituted dibenzoheterocyclic compound and preparation method thereof
Percec et al. Design of side chain and main chain liquid crystalline polymers containing supramolecular quasi-rigid-rodlike mesogens obtained from collapsed main chain macrocyclics
JP2008201682A (en) Compound having dendron and mesogen, liquid crystal composition and photo-element
TW201412951A (en) Liquid crystal compound having (difluoro) ethylene glycol-based structure and liquid crystal composition
CN101880219B (en) Liquid crystal compound and preparation method thereof
CN112480048B (en) Compound, liquid crystal medium, liquid crystal display element and liquid crystal display
CN101973878B (en) Liquid crystal compound containing dicyclohexyl as well as preparation method and application thereof
Lee et al. Synthesis and curing of liquid crystalline epoxy resin based on naphthalene mesogen
Gayathri et al. Self-assembly of azobenzene based side-chain liquid crystalline polymer and n-alkyloxybenzoic acids
TW201602316A (en) Liquid crystal compound and liquid crystal composition containing the same
Zhang et al. Design, synthesis, and characterisation of symmetrical bent-core liquid crystalline dimers with diacetylene spacer
M. Salleh et al. Effect of the lateral substituent on the mesomorphic behavior of side-chain liquid-crystalline polymers containing a Schiff base ester
Yang et al. Self-organization of cholesterol-side-chain liquid crystalline polymers by tailoring the main chain structure and flexible spacer length
JP4452826B2 (en) Process for producing chiral polymer and chiral polymer obtained thereby
Boopathi et al. Click reaction assisted synthesis of heterocyclic liquid crystals and its characterization
Ku et al. Correlation of self-assembly and thermal conducting properties of PEG-backbone polyether with a room temperature mesophase
CN110938439B (en) High-polarity large-optical birefringence liquid crystal composition
CN114231294A (en) Negative liquid crystal composition and application thereof
Goto et al. Synthesis and properties of mono-substituted liquid crystalline polyacetylene derivatives—doping, magnetic orientation, and photo-isomerization
CN114929839A (en) Liquid crystal composition, liquid crystal display element and compound
Balamurugan et al. Synthesis and characterization of symmetrical banana shaped liquid crystalline polyethers

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
ASS Succession or assignment of patent right

Owner name: SHENZHEN DALTON ELECTRONIC MATERIAL CO., LTD.

Free format text: FORMER OWNER: TSINGHUA UNIVERSITY

Effective date: 20131031

C41 Transfer of patent application or patent right or utility model
COR Change of bibliographic data

Free format text: CORRECT: ADDRESS; FROM: 100084 HAIDIAN, BEIJING TO: 518125 SHENZHEN, GUANGDONG PROVINCE

TR01 Transfer of patent right

Effective date of registration: 20131031

Address after: 518125 Guangdong city of Shenzhen Province Hong Baote Jia Tian Cun manhole Street Industrial Park

Patentee after: SHENZHEN DALTON ELECTRONIC MATERIAL Co.,Ltd.

Address before: 100084 Tsinghua Yuan, Beijing, Haidian District, Tsinghua University, 1

Patentee before: Tsinghua University

DD01 Delivery of document by public notice

Addressee: SHENZHEN DALTON ELECTRONIC MATERIAL Co.,Ltd.

Document name: Notification to Pay the Fees

PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: A liquid crystal compound containing dicyclohexyl and its preparation method and Application

Effective date of registration: 20211117

Granted publication date: 20130410

Pledgee: Shenzhen hi tech investment small loan Co.,Ltd.

Pledgor: SHENZHEN DALTON ELECTRONIC MATERIAL Co.,Ltd.

Registration number: Y2021980012687

PE01 Entry into force of the registration of the contract for pledge of patent right
CP03 Change of name, title or address

Address after: Building B3, 4C, No. 2533, Fenghuang Community Sightseeing Road, Fenghuang Street, Guangming District, Shenzhen City, Guangdong Province, 518109

Patentee after: Shenzhen Dalton Electronic Materials Co.,Ltd.

Address before: 518125 Jiabao Special Industrial Park, Hongtian Village, Shajing Street, Shenzhen City, Guangdong Province

Patentee before: SHENZHEN DALTON ELECTRONIC MATERIAL Co.,Ltd.

CP03 Change of name, title or address