JPS5838221A - 4-(trans-4"-(trans-4"-alkylcyclohexyl)-cyclohexyl) biphenyl - Google Patents

Abstract

NEW MATERIAL:The compound of formulaI(R is H or 1-10C alkyl). USE:A liquid crystal compound having small positive dielectric anisotropy, broad liquid crystal temperature range, especially high clear point of liquid crystal (N-I point or Sm-I point) and low viscosity. It is stable to heat, air, moisture, light, etc. PROCESS:The compound of formulaIis prepared by (1) reacting the compound of formula II with metallic Mg to obtain the compound of formula III, (2) reacting the compound with the compound of formula IV, (3) dehydrating the resultant compound of formula V to the compound of formula VI using KHSO4 as the catalyst, (4) reducing the product in ethanol solvent under normal pressure at 30 deg.C using Raney-Ni catalyst, and (5) recrystallizing the resultant mixture of the trans-and cis-isomers with ethanol.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to highly stable and low activity fi-like materials that exhibit a liquid crystalline phase over a wide range of temperatures.

The liquid crystal Takako has 1 quality of liquid crystal and 11 optical sides! And Masuden^, I gave 8M L to my sister, but due to the demonstration, TNji (twisted nematic layer), DamC1m
There are various types of liquid crystal materials, such as catalytic scattering, guest/host, and DAP jl, and the properties of the liquid crystal materials suitable for each type of use are different. However, all liquid crystal substances contain water! 2 qi, heat,
It is common that the system must be stable to light, etc.
In addition, the liquid crystal phase should be exhibited at a wide temperature range centered around room temperature, and the optimum dielectric polarity (6g>1) should be determined depending on the type of the disclosed device.
However, currently, there is no material that satisfies this condition in single-metal metal products, and liquid crystal compositions such as liquid crystal metal products and non-liquid crystal compounds are used for convenience. Ami at present.

Recently, the temperature has ranged from particularly low (-2 olclijll) to high temperature (6
The surface water height that operates over 0'-90C) has been increased to 441m, so it is a wide Kame 1LII.
The liquid crystal display is highly praised for its excellent operating characteristics.

An object of the present invention is to provide a novel liquid crystal compound useful as a parabolic component of a ζζ crystal a composition and suitable for improving high temperature properties t' to 41.

That is, the present invention is represented by -R formula % formula % (1) (in the above formula, R represents a water volume or an alkyl group having 1 to 10 carbon atoms), and 44-[) lance-4'-() Lance-4-
Furkylcyclohexyl)cyclohexyl]biphenyl.

The compound of the present invention exhibits a small positive anisotropy value, has a wide range of crystal clearness, and has a typical liquid crystal clearing point (N-1 point, or 8-1 point). It is a compound with low viscosity, and is stable at 41K, making it extremely useful for creating liquid crystal compositions that operate with wide tortuosity from low to high temperatures. It is a m'a compound.

Next, the method for producing the compound of the present invention will be shown. First, 4-10
% biphenyl and metallic magnesium are reacted to form 4-biphenylmagnesic conjugates, which are then converted into 4-(trans-4'-1-biphenyl chloride) schif-nannones (corresponding cy/lohequinanones). 4-[
: 1'-Human-oxygen-4'-()nssu/-yyl-cyclohexy)schiff-he-cyclosyl]biphenyl 0 Then, this was subjected to severe dehydration to am hydrogen power of 99^t-1!1. 4-(4'-()nnsu l-a J&14Fk
hexen-11-yl] biphenyl. This is then reduced to 4-[4
``-() Lance-4-arcyl is obtained as hexyl)cyclohexy-)biphenyl, which is a mixture of trans and cis forms, so it is recrystallized with an engineered substance to obtain the desired 4- [trans-4'-()trans-4-γrukih
Cyclohexy 2) Cyclohexysil] Bifueni body is obtained.

The above is expressed by a chemical formula.Hereinafter, the manufacturing method and usage examples of the compound of the present invention will be explained in detail using examples.

Example 1 (4= [) Lance-4"-(Trans-l
Production of mp-form magnesium 569 (0,148 mol) 3 4-bromobiphenyl 545? (C
I1m obtained by dissolving L1487k) in tetrahydro727
30sgt-% value in bulk airflow''c & reaction torque v30~3
Keep it at 5℃, and add it dropwise without stirring.It will react and magnesilla will come out evenly in 5 hours.
Generates magnesium hydroxide. 4-(tons = 4'-7' Robilsik deception hexyl) cyclohex I? - / 2422 (α118 mol) of t-Tetrahydrofuran to make 50- t Reaction temperature of 5 to
Lower the temperature as quickly as possible while maintaining the temperature at 10℃.

After dropping, the temperature was raised to 55C and stirred for 50 minutes, then sN
Salt @1 [10mt', ill, t! . After extracting the IN reaction 11tt and 11P+ three times with 10 mouths of toluene, the combined tomatoene layer was washed with water until the washing solution became neutral to 1, and then the toluene was transferred under reduced pressure. The remaining chains are 4-[
1-human-oxy-4'-()ns-4-propylcyclohexy-&)cyclohexyl]biphenyl, and a lot of potassium hydrogen sulfate was added to it in a nitrogen stream to 161:
Dehydrate for 2 hours. After cooling, 500 ml of toluene is added, the am hydrogen potassium is separated from the P, and the toluene layer is washed with water until the washing liquid becomes neutral. Next, toluene was distilled off under reduced pressure, and the remaining oil was recrystallized with ethanol to obtain 4.
-(4''-()lance-4#-propylcyclohexyl) 9 Chlohexen-1'-yl]biphenyl.
Catalytic reduction of Ia was carried out with 2 t of ethanol and 300 mg of water at a bulk pressure of 51%'j 5 o t: to absorb 410 of hydrogen. The contact part of FJII is then recrystallized. Since the obtained product is a compound of cis and trans forms, MA is repeated again with ethanol to isolate the trans form.

This is 4-[trans-4'-()rance-4-10
Birucyclohexy A) cyclohexy-)---biphenyl. Jin's #i crystal - Smektek (C-8
m) Relative 912℃ smectic-nematic (lEr1-
N) Point 2145c Nematic - Clear (N-1) Point 26 parts 7°C Yield 2. ．． It was 6f @ thing 5116. It was confirmed by NMR spectrum elemental analysis that this product was the target product.

Examples 2 and 3 Using the same al as the method shown in Example 1, compounds of formula (I) in which R is H and those in which R is C, H, or 2 were produced. Those 0@
The amount, yield and physical properties are shown in Table 1 together with the results of Example 10.

Real m Confucian 4 ([N11) Trans-4-G Fight Building- (4'-Cyanofe x, &
) Cyclo to Nakanan 28-trans-4-pliers x -(4'-cyanofe&k)
Schiff-yellow hekinane 45-trans-4-heguchimi-(4'-cyanopheniA) cyclohekinan 29-1 to 4Mi product parabolic temperature range is -S to 52℃,
-Electrical anisotropy value Δ# is +1 (L5, threshold voltage is 1.5
FV, saturation voltage is 2-12V.

This food is 90gKyi! A liquid crystal display with 10 parts of 4-(trans-4'-()lance-C-bench body cyclostomy hexyl) cyclo^xyl bi7 engineering JL) equipped with 11115! Chick turtle IR, II cabinet is -5~71 tK
There was a lot of gourd, ΔC was 100% a1 threshold voltage was t60v% 60% pressure was increased to uOV, but the viscous J [was 2SQ) was not different.

that's all

Claims (2)

[Claims] (1) 4-[trans-4'-()trans-l-
Alkylcyclohexyl) cyclohexyl] piphenyl. (2) General formula (4-[trans-4'-(trans-4#) is represented by hydrogen or alkyl having 1 to 1 carbon atoms.
-Ah Kih Cyclohexy) Cyclohex S/Jh] Bifue K (also contains one type of sew is considered to be tatami mold)