CN101323596B - 2-site ethynyl contained pyrimidine ring liquid crystal compounds and method for preparing the same - Google Patents
2-site ethynyl contained pyrimidine ring liquid crystal compounds and method for preparing the same Download PDFInfo
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Abstract
The invention discloses a 2-site pyrimidine ring liquid crystal compound containing acetenyl and a preparation method thereof, belonging to the field of chemical industry. The general formula of the chemical structure of the new pyrimidine ring liquid crystal compound of the invention is that: the structure of the compound comprises pyrimidine ring and phenylethynyl; the compound has relatively large optical anisotropy, relatively low viscosity and relatively wide nematic phase temperature range. If a liquid crystal compound or a compound is added with the liquid crystal compound of the invention, a liquid crystal compound with good capacities can be obtained and the response speed and the low temperature compatibility of a nematic phase liquid crystal composition for display can be greatly improved. The 2-site pyrimidine ring liquid crystal compound containing acetenyl can be used in RSM, PDLC and optical communication etc. having higher requirements on liquid crystal displays of large delta-n liquid crystal materials.
Description
Technical field
The present invention relates to a kind of new pyrimidine lopps liquid crystalline cpd, be meant that more specifically a kind of 2 contain pyrimidine lopps liquid crystalline cpd of ethynyl and preparation method thereof.
Background technology
At present; Liquid crystal material has obtained using widely in field of information display; Based on the liquid crystal device of twisted-nematic principle, become our the indispensable part of living with product forms such as mobile phone, computer, TVs like: display devices such as TN-LCD, STN-LCD, TFT-LCD.But, being accompanied by the enhancing of people's energy-conserving and environment-protective consciousness, PDLC shows that (PDLC) obtained favor again! Light scattering mode (RSM), optical communication etc. also have requirements at the higher level to the liquid crystal material with big optical anisotropy (Δ n); Simultaneously; PDLC also will consider the problem that mixed liquid crystal material and various polymerization objects system mate each other with liquid crystal material, equally also requires the Δ n of liquid crystal material bigger.
Liquid crystal material is one of main raw that constitutes by liquid-crystal display (LCD), and, being accompanied by the difference of display format, required liquid crystal material is also different.Therefore, the liquid crystal material of demonstration usefulness also is accompanied by the development of liquid-crystal display and grows in strength, and a large amount of liquid crystalline cpds occurred.Develop into cyclohexyl (couplet) benzene class, diphenyl acetylene class, ethyl bridged bond class, end alkene class and fluorine-containing aromatic ring class liquid crystalline cpd from azo, azoxy, benzal, biphenyl nitrile, ester class, oxygen heterocyclic ring class, pyrimidine lopps liquid crystalline cpd; Its molecular structure is more and more unique; Performance characteristics is more and more outstanding, is constantly satisfying display devices such as TN-LCD, STN-LCD, TFT-LCD, PDLC to performance demands.
People usually need mix the liquid crystalline cpd that uses about 20 kinds of different performances in order to satisfy the needed individual features of various liquid crystal display devices, use with form of mixtures, therefore, need liquid crystalline cpd to have good mutual solubility, particularly at low temperatures.But along with the increase of the Δ n of liquid crystalline cpd, the intermiscibility of itself and other liquid crystal material will variation, is difficult to more especially at low temperatures mix.In order to change these deficiencies, increase the molecule width through in the liquid crystalline cpd structure, introducing fluorine atom, can reduce fusing point, increase intermiscibility, improve low-temperature performance.
People introduce the conjugation group usually, increase conjugate length in order to obtain having the liquid crystalline cpd of big Δ n.The liquid crystalline cpd that has synthesized some big Δ n in the prior art, for example hexanaphthene diphenyl acetylene derivatire and fluorine substituted diphenyl acetylene end isothiocyano analog derivative.Comprise more following compounds in the liquid crystalline cpd that foreign patent US5437815, EP1054001 and US2005067605 mention, the fundamental property of these compounds be listed in chemical formula below:
Optical anisotropy Δ n is the important parameter of liquid crystal material, in liquid-crystal display, needs careful adjustment.Though the liquid crystal material of some big Δ n receives publicity in recent years, the liquid crystal material of some big Δ n is synthesized out in succession,, its performance not too adapts to the needs of market development, and the user of liquid crystal material is still not too satisfied!
Summary of the invention
The technical issues that need to address of the present invention provide a kind of 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl, and this compound has bigger optical anisotropy, bigger electricity anisotropy and the nematic temperature range of broad.
Another object of the present invention provides a kind of 2 preparing methods that contain the pyrimidine lopps liquid crystalline cpd of ethynyl.
A further object of the present invention provides a kind of 2 liquid-crystal compsns that contain the pyrimidine lopps liquid crystalline cpd of ethynyl that contain.
For solving the problems of the technologies described above, the technical scheme that the present invention taked is:
A kind of 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl, this compound has the structure shown in the general formula (I):
Wherein: R is C
1～C
10Alkyl, C
1～C
10Alkoxyl group, C
2～C
10Thiazolinyl, at least one Wasserstoffatoms are by the substituted C of fluorine atom
1～C
10Alkyl, at least one Wasserstoffatoms are by the substituted C of fluorine atom
1～C
10Alkoxyl group, at least one Wasserstoffatoms are by the substituted C of fluorine atom
2～C
10Thiazolinyl wherein a kind of;
X
1, X
2Be respectively H or F or Cl atom;
N is 0 or 1;
Y is-CN ,-OCF
3,-OCF
2H ,-F ,-CL, C
1～C
10Alkyl, C
1～C
10Alkoxyl group.
A kind of 2 pyrimidine lopps liquid crystalline cpd institute preferred structures that contain ethynyl of the present invention are following various listed compound, but are not limited to following compound:
Compound of the present invention further is optimized for: above-mentioned R is preferably C
1～C
10Straight chained alkyl, C
1～C
10Straight chain alkoxyl group, C
2～C
10Straight-chain alkenyl, at least one Wasserstoffatoms are by the substituted C of fluorine atom
1～C
10Straight chained alkyl, at least one Wasserstoffatoms are by the substituted C of fluorine atom
1～C
10Straight chain alkoxyl group, at least one Wasserstoffatoms are by the substituted C of fluorine atom
2～C
10Straight-chain alkenyl.
The further preferred version of above-mentioned R is: C
1～C
7Straight chained alkyl, C
1～C
5Straight chain alkoxyl group, C
2～C
5Straight-chain alkenyl.Most preferred scheme is-CH
3,-C
2H
5, n-C
3H
7, n-C
4H
9Or n-C
5H
11
The present invention and above-listed X described in various
1, X
2Further preferred version be: X
1, X
2Be fluorine atom (F).
The present invention and above-listed Y described in various are preferably :-CN ,-OCF
3,-OCF
2H ,-F ,-CL, C
1～C
6Alkyl, C
1～C
5Alkoxyl group.
The further preferred version of above-mentioned Y is :-OCF
3,-OCF
2H ,-F, C
1～C
6Alkyl, C
1～C
5Alkoxyl group.
The most preferred scheme of Y is :-OCF
3,-OCF
2H ,-F, C
1～C
5Alkyl, C
1～C
2Alkoxyl group.
2 above-mentioned a kind of preparing methods that contain the pyrimidine lopps liquid crystalline cpd of ethynyl, its synthetic route is represented as follows with reaction formula:
R in the above-mentioned reaction formula is consistent with the substituent scope of R in the above-mentioned general formula (I), X
1, X
2Be respectively H or F or Cl, it is preferably F.Y is :-CN ,-OCF
3,-OCF
2H ,-F ,-CL, C
1～C
10Alkyl, C
1～C
10Alkoxyl group.
The preparing method's of the compound of the described general formula of above-mentioned reaction formula (I) step is following with character express:
Step 1, α-R substituted cyclohexyl (A formula) obtain 2-hydroxyl-5-R substituted cyclohexyl pyrimidine (B formula) with urea cyclization under the acid catalysis effect in the solution of organic solvent.Perhaps
Phenyl-β-ethoxy-c olefine aldehydr (A formula) obtains phenyl pyrimidine (B formula) with urea cyclization under the acid catalysis effect in the solution of organic solvent.
The compound of step 2, step 1 gained (B formula) reacts under the organic amine katalysis with POCl3, obtains 2-chloro-5-R substituted cyclohexyl or phenyl pyrimidine (C formula);
The compound of step 3, step 2 gained (C formula) is dissolved in the solution of organic solvent, under the Pd catalyzer, with the substitutedphenylethynyl reaction, carries out organic solvent extraction, carries out column chromatography again and purifies, and obtains 2 pyrimidine lopps liquid crystalline cpds (I formula) that contain ethynyl.
Acid described in the above-mentioned steps 1 is acetic acid, formic acid, sulfuric acid, hydrogenchloride, its preferred hydrogenchloride.
Organic solvent described in the step 1 is methyl alcohol, ethanol, Virahol, its particular methanol.
Organic amine described in the above-mentioned steps 2 is triethylamine, trolamine, N, accelerine, Diisopropylamine, its preferred triethylamine.
Pd catalyzer described in the above-mentioned steps 3 is Pd (PPh
3)
4, PdPPh
3Cl
2, its preferred Pd (PPh
3)
4
The used organic solvent of extraction described in the step 3 is methylene dichloride, chloroform, MTBE, tetrachloroethane, its preferred methylene dichloride.
Used organic solvent was sherwood oil, heptane, hexane, methylene dichloride, toluene, ETHYLE ACETATE when column chromatography was purified in the step 3, its preferred sherwood oil.
2 pyrimidine lopps liquid crystalline cpds that contain ethynyl can mix the composition liquid-crystal compsn with other liquid crystalline cpd, thereby realize the 3rd goal of the invention of the present invention.In the liquid-crystal compsn of the present invention, comprise 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl of 1～12wt% (weight percentage), all the other components are known other liquid crystalline cpds of prior art.
In the above-mentioned liquid-crystal compsn, the preferred weight percentage composition of compound of the present invention is 2～8wt%, most preferably is 3～7wt%.
The known liquid crystalline cpd of prior art described in the above-mentioned liquid-crystal compsn, the compound shown in preferably following (II)-(X), but be not limited in them:
Owing to adopted technique scheme, the technical progress that the present invention obtained is:
Liquid crystalline cpd provided by the invention---general formula (I) is compared with other liquid crystalline cpds of prior art; Have very big optical anisotropy (Δ n), bigger electricity anisotropy (Δ ε) and the nematic temperature range of broad; Have good compatibility at low temperatures, their chemical property all is stable; Raw material in general formula (I) the preparation process is easy to get, and synthetic route is simple, does not need too complicated Special Equipment, is fit to large-scale industrial production, is beneficial to as showing with liquid crystal material to use, and can be used for improving the response speed and the driving voltage of liquid-crystal compsn.
In existing known other liquid crystalline cpd or in the compsn, add liquid crystalline cpd of the present invention, can obtain a kind of liquid-crystal compsn, can improve the response speed and the low temperature compatibility that show with nematic phase liquid crystal composition greatly with superperformance.Can be used for light scattering mode (RSM), PDLC, optical communication etc. has the liquid-crystal display of requirements at the higher level to the liquid crystal material of big Δ n.
Preferred through test of many times, the performance of pyrimidine lopps liquid crystalline cpd that several kinds 2 of finally confirming of the present invention are contained ethynyl is more stable, and quality is more reliable.
Embodiment
Below in conjunction with specific embodiment the present invention is done further explanation.
Embodiment 1
The described liquid crystalline cpd of present embodiment is 2-(4`-amylbenzene acetylene)-5-propyl group pyrimidine, its chemical formula (I-1) as follows:
Its preparation method is:
The preparation of step 1,2-hydroxyl-5-propyl group pyrimidine:
In reaction flask, add 64g (0.45mol) α-propyl group-β-ethoxy-c olefine aldehydr, 20g urea and 200ml methyl alcohol, 10～20 ℃ of controlled temperature feed 0.2 mole HCL gas; After reacting 5～6 hours, reheat back flow reaction 4 hours is lowered the temperature then, is reduced pressure; And the removal organic solvent, obtain the oily solid, carry out recrystallization with 3 times of ethanol; Filter then, filter cake just can get albescent 2-hydroxyl-5-propyl group pyrimidine crystal 3 3.1g with the cold alcohol flushing of 20ml; The gas chromatographic purity of this product >=99.5%, yield are 75%.
The preparation of step 2,2-chloro-5-propyl group pyrimidine:
In reaction flask, add 44.6g (0.32mol) 2-hydroxyl-5-propyl group pyrimidine, be cooled to-5 ℃, beginning slowly drips the 200ml POCl3, in the dropping process temperature control at-5～0 ℃, about 2 hours of dropping time; And then under-5～5 ℃, drip triethylamine 50ml, under this temperature, kept 2 hours again after finishing.Progressively be warmed up to reflux temperature then, back flow reaction 4 hours.
Then, distillation POCl3 under normal pressure is after POCl3 is distilled approximately above 1/2, till all distillating with water-bath underpressure distillation to POCl3 again.Reduce to room temperature, the article in the reaction flask are carefully poured in the frozen water of 200g and made its hydrolysis.Add sodium-chlor and make solution saturated, use dichloromethane extraction solution, methylene dichloride 300ml is used in coextration 3 times at every turn, then extraction liquid is merged, and is neutralized to alkalescence with 5% sodium hydrogencarbonate, and washing adds anhydrous magnesium sulfate drying to neutral again.Filter out siccative, decompression steams solvent, and (110 ℃/3mmHg), can get 2-chloro-5-propyl group pyrimidine 39.1g, the gas chromatographic purity of product >=99%, productive rate: 78% of 2-chloro-5-propyl group pyrimidines are collected in decompression.
The preparation of step 3,2-(4`-amylbenzene acetylene)-5-propyl group pyrimidine:
In reaction flask, add 2-chloro-5-propyl group pyrimidine 32.9g (0.21mol), 4-amylbenzene acetylene 34.4g (0.2mol), 0.5g cuprous iodide, 0.3g Pd (PPh
3)
4, 100ml triethylamine and 100ml toluene, under nitrogen protection, reflux, reacted 10 hours.Reduce to room temperature, filter, with 50ml dichloromethane rinse insolubles, totally 2 times; Merging filtrate adds 500ml water, mixes separatory; Obtain the aqueous solution and organic phase, water layer is used the 100ml dichloromethane extraction once again, merges with organic phase then; Hydrochloric acid with 5% is neutralized to acidity, and water is washed till neutrality again, adds anhydrous magnesium sulfate drying.Cross and filter to remove siccative; Solvent is removed in decompression, and excess carries out that column chromatography is purified, decolouring after with the 300ml petroleum ether dissolution, decompression removal solvent; Use twice of 2 times of sherwood oils and 1 times of ethyl alcohol recrystallization again; Can get white 2-(4`-amylbenzene acetylene)-5-propyl group pyrimidine crystal 3 1.2g, the product gas chromatographic purity: 99.8%, productive rate: 76%.
The compound of gained is through experiment discovery, liquid crystalline cpd phase-state change: C61.7 ℃, N74.3 ℃ of I.(C representes the fusing point of liquid crystalline cpd; N representes clearing point temperature, and mesomorphic phase is promptly arranged; Temperature when I representes equal one.Down together)
Embodiment 2
The described liquid crystalline cpd of present embodiment is 2-(4`-anisole acetylene)-5-propyl group pyrimidine, its chemical formula (formula I-2) as follows:
Its preparation process is identical with embodiment 1, and difference is: in step 3, the used raw material of present embodiment is a 4-anisole acetylene, rather than 4-amylbenzene acetylene.
The performance test result who prepares compound (I-2) is following:
Liquid crystalline cpd phase-state change: C75.3 ℃ N81.3 ℃ I.
Embodiment 3
The described liquid crystalline cpd of present embodiment is 2-(2 '-fluoro-4`-amylbenzene acetylene)-5-propyl group pyrimidine, its chemical formula (formula I-3) as follows:
Its preparation process is with embodiment 1, and difference is to change the raw material 4-amylbenzene acetylene in the step 3 of embodiment 1 into 2-fluoro-4-amylbenzene acetylene, prepares title product (I-3).
Learn that through experiment the phase-state change of this liquid crystalline cpd is: C52.5 ℃ of N67.5 ℃ of I.
Embodiment 4
The described liquid crystalline cpd of present embodiment is 2-(3 '-fluoro-4`-amylbenzene acetylene)-5-amyl group pyrimidine, its chemical formula (formula I-4) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-amyl group-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene changes 3-fluoro-4-amylbenzene acetylene in the step 3, prepares title product (I-4).
Learn that through experiment the phase-state change of this liquid crystalline cpd is: C69.3 ℃ of N73.8 ℃ of I.
Embodiment 5
The described liquid crystalline cpd of present embodiment is 2-(2 ', 3 '-two fluoro-4`-amylbenzene acetylene)-5-propyl group pyrimidine, its chemical formula (formula I-5) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: with the raw material 4-amylbenzene acetylene in the step 3 of embodiment 1 change 2 into, 3-two fluoro-4-amylbenzene acetylene, prepare title product (I-5).
Learn that through experiment the phase-state change of this liquid crystalline cpd is: C48.5 ℃ of N54.3 ℃ of I.
Embodiment 6
The described liquid crystalline cpd of present embodiment is 2-(2 '-fluoro-4`-amylbenzene acetylene)-5-(the trans propyl group cyclohexyl of 4-) pyrimidine, its chemical formula (formula I-6) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(the trans propyl group cyclohexyl of 4-)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2-fluoro-4-amylbenzene acetylene into, can prepare the title product (I-6) of present embodiment.Learn that through experiment the phase-state change of this liquid crystalline cpd is: C84.6 ℃ of N206.8 ℃ of I.
Embodiment 7
The described liquid crystalline cpd of present embodiment is 2-(2 ', 3 '-two fluoro-4`-amylbenzene acetylene)-5-(the trans propyl group cyclohexyl of 4-) pyrimidine, its chemical formula (formula I-7) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(the trans propyl group cyclohexyl of 4-)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2 into, 3-two fluoro-4-amylbenzene acetylene, can prepare title product (I-7).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C71.6 ℃ of N187.3 ℃ of I.
Embodiment 8
The described liquid crystalline cpd of present embodiment is 2-(2 ', 3 ', 4 '-trifluoro-benzene acetylene)-5-(the trans propyl group cyclohexyl of 4-) pyrimidine, its chemical formula (formula I-8) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(the trans propyl group cyclohexyl of 4-)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2,3 into, 4-trifluoro-benzene acetylene, can prepare title product (I-8).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C87.5 ℃ of N175.1 ℃ of I.
Embodiment 9
The described liquid crystalline cpd of present embodiment is 2-(2 ', 3 '-two fluoro-4 '-trifluoromethoxy phenylacetylene)-5-(the trans propyl group cyclohexyl of 4-) pyrimidine, its chemical formula (formula I-9) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(the trans propyl group cyclohexyl of 4-)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2 into, 3-two fluoro-4-trifluoromethoxy phenylacetylenes, prepares title product (I-9).
Learn that through experiment the phase-state change of this liquid crystalline cpd is: C104.6 ℃ of N211.5 ℃ of I.
Embodiment 10
The described liquid crystalline cpd of present embodiment is 2-(2 ', 3 '-two fluoro-4 '-trifluoromethoxy phenylacetylene)-5-(4-propylbenzene) pyrimidine, its chemical formula (formula I-10) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(4-propylbenzene)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2 into, 3-two fluoro-4-trifluoromethoxy phenylacetylenes, can prepare the described liquid crystalline cpd of present embodiment (I-10).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C143.2 ℃, S156.3 ℃, N221.1 ℃ I.
Embodiment 11
The described liquid crystalline cpd of present embodiment is 2-(4`-amylbenzene acetylene)-5-(2 ', 3 '-two fluoro) normal-butyl pyrimidine, its chemical formula (formula I-11) as follows:
Its preparation process is with embodiment 1; Be with the difference of embodiment 1: change the raw material α-amyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-(2 '; 3 '-difluoro replaces) normal-butyl-β-ethoxy-c olefine aldehydr, can prepare title product (I-11).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C42.3 ℃ of N51.2 ℃ of I.
Experimental example 12
The described liquid crystalline cpd 2-of present embodiment (4`-amylbenzene acetylene)-5-positive propoxy pyrimidine, its chemical formula (formula I-12) be as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-propyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-positive propoxy-β-ethoxy-c olefine aldehydr, can prepare title product (I-12).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C57.2.4 ℃ N46.7 ℃ I (monotropic).
Embodiment 13
The described liquid crystalline cpd of present embodiment is the positive propenyl of 5-(1)-2-(2 ', 3 ', 5 '-three fluoro-4`-isothiocyano base phenylacetylenes) pyrimidine, its chemical formula (formula I-13) as follows:
Its preparation process is with embodiment 1, is with the difference of embodiment 1: change the raw material α-amyl group in the step 1 of embodiment 1-β-ethoxy-c olefine aldehydr into α-propenyl (1)-β-ethoxy-c olefine aldehydr; Raw material 4-amylbenzene acetylene in the step 3 changes 2-fluoro-4-amylbenzene acetylene into, can prepare title product (I-13).Learn that through experiment the phase-state change of this liquid crystalline cpd is: C39.7 ℃ of N61.3 ℃ of I.
The liquid crystal property parameter of the liquid crystalline cpd of the embodiment of the invention 1～13 is following:
Can find out from the liquid crystal property parameter of above compound; Compound of the present invention has possessed the necessary characteristic as liquid crystal material; Has bigger optical anisotropy; Awide temperature range is arranged, and it is as showing the response speed and the driving voltage that can improve liquid-crystal compsn with liquid crystal material, and can be used for light scattering mode (RSM), PDLC, optical communication etc. has liquid-crystal displays such as requirements at the higher level to the liquid crystal material of big Δ n.
Embodiment 14:
The liquid-crystal compsn that contains the general formula I liquid crystalline cpd comprises following composition:
Wherein, " % " expression " mass percent ", the characteristic of measuring in the present embodiment is as follows:
Phase inversion temperature TNI is: 85.4 ℃; 25 ℃ of specific refractory power anisotropy Δ n:0.215 that measure down; 20 ℃ of body viscosities il of measuring down are: 29.0mPas; When constituting the TN-LCD of the thick 6 μ m of box, at 25 ℃ of threshold voltage vt h that measure down be: 2.63V.
Embodiment 15
The liquid-crystal compsn that contains the general formula I liquid crystalline cpd comprises following composition:
The characteristic of measuring in the present embodiment is: TNI:89.1 ℃; Δ n:0.2 05; η: 31.0mPas.
Claims (4)
1. one kind 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl is characterized in that: the structural formula of this compound is following a kind of
Wherein: R is C
3～C
7Straight chained alkyl, C
1～C
5Straight chain alkoxyl group, C
2～C
5Straight-chain alkenyl;
Y is-CN ,-OCF
3,-OCF
2H ,-F ,-CL, C
1～C
10Alkyl, C
1～C
4Alkoxyl group.
2. a kind of 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl according to claim 1 is characterized in that described R is-CH
3,-C
2H
5, n-C
3H
7, n-C
4H
9Or n-C
5H
11
3. according to claim 1 or 2 described a kind of 2 preparing methods that contain the pyrimidine lopps liquid crystalline cpd of ethynyl, it is characterized in that comprising the steps:
Step 1, α-R substituted cyclohexyl or phenyl-β-ethoxy-c olefine aldehydr and urea cyclization under acid catalysis obtain 2-hydroxyl-5-R substituted cyclohexyl or phenyl pyrimidine;
The compound of step 2, above-mentioned gained and POCl3 react under organic amine catalysis and obtain 2-chloro-5-R substituted cyclohexyl or phenyl pyrimidine;
Step 3, above-claimed cpd can obtain 2 pyrimidine lopps liquid crystalline cpds that contain ethynyl with the substitutedphenylethynyl reaction under the Pd catalyzer.
4. according to claim 1 or 2 described a kind of 2 liquid-crystal compsns that contain the pyrimidine lopps liquid crystalline cpd of ethynyl; It is characterized in that: comprise in the liquid-crystal compsn 1～12wt% the described compound of claim 1 wherein one or several, also comprise wherein several kinds of following compounds in addition in the liquid-crystal compsn
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| CN101544892B (en) * | 2009-05-07 | 2012-10-03 | 石家庄诚志永华显示材料有限公司 | Method for synthesizing diaryl acetylene monomer liquid crystal |
| JP5234227B2 (en) | 2011-04-06 | 2013-07-10 | Ｄｉｃ株式会社 | Nematic liquid crystal composition and liquid crystal display device using the same |
| WO2013047359A1 (en) | 2011-09-27 | 2013-04-04 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display element using same |
| CN111234844B (en) * | 2016-11-22 | 2023-03-14 | Dic株式会社 | Liquid crystal composition and liquid crystal display element |
| CN110938439B (en) * | 2019-11-14 | 2021-03-19 | 清华大学 | High-polarity large-optical birefringence liquid crystal composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996030344A2 (en) * | 1995-03-28 | 1996-10-03 | The Secretary Of State For Defence | Pyrimidine compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996030344A2 (en) * | 1995-03-28 | 1996-10-03 | The Secretary Of State For Defence | Pyrimidine compounds |
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| CN101323596A (en) | 2008-12-17 |
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