Liquid Crystals

ISSN: 0267-8292 (Print) 1366-5855 (Online) Journal homepage: http://www.tandfonline.com/loi/tlct20

Synthesis and mesomorphic properties of

four-ring fluorinated liquid crystals with
trifluoromethyl group

Jianxun Wen, Ruiwen Tian & Xiuwen Dai

To cite this article: Jianxun Wen, Ruiwen Tian & Xiuwen Dai (2017): Synthesis and mesomorphic
properties of four-ring fluorinated liquid crystals with trifluoromethyl group, Liquid Crystals, DOI:
10.1080/02678292.2017.1285058

To link to this article: http://dx.doi.org/10.1080/02678292.2017.1285058

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LIQUID CRYSTALS, 2017
http://dx.doi.org/10.1080/02678292.2017.1285058

ARTICLE

Synthesis and mesomorphic properties of four-ring fluorinated liquid crystals

with trifluoromethyl group
Jianxun Wen, Ruiwen Tian and Xiuwen Dai
Fujian Yongjing Technology Co., Ltd., Shaowu, Fujian, China

ABSTRACT ARTICLE HISTORY

The discovery of nematic phase in 3-fluoro-4-trifluoromethyl-4ʹ-(4ʹ-alkyl [trans, trans-1,1ʹ-bicyclohexyl]- Received 29 October 2016
4-yl) 1,1ʹ-biphenyls (n = 2, 3, 4, 5) is an accidental affair. A convenient method was used for the synthesis Accepted 17 January 2017
of these target compounds. After the preparation of the intermediate with trifluomethyl group, the KEYWORDS
target compounds were synthesised by Suzuki cross-coupling reaction. Then, these phase transition Fluorinated liquid crystal;
temperatures were measured by polarising textural observation, which confirmed the existence of clearing point; nematic
single nematic phase. These temperatures were also measured by differential scanning calorimetry, phase; fluorophilic;
which showed that the clearing point of compound (n = 3) is 267℃. The possible mechanism of trifluoromethyl
occurrence of unique nematic phase was discussed on the basis of the principles of fluorine chemistry.

Introduction However, the molecular structure and the shape are

very important factors to design the material perfor-
Liquid crystal display (LCD) devices are widely used
mance, which is optimised by organic synthesis [6,7].
for watches, desktop calculators and several kinds of
In simple twisted nematic LCD, there are severe limita-
measuring apparatus panels for automobiles and tele-
tions as the molecules cannot respond fast enough to
visions. They are now pervading our daily lives [1,2].
such addressing, and hence contrast suffers greatly. A
The LCD industry is growing into a large-scale industry.
further development in the mid-1980s was super-
For a thin-film transistor (TFT)-LCD to be commercially
twisted nematic displays (STN), which inherently pro-
viable in the TV market and to expand its market share,
vide a steeper electro-optic characteristics. Hence, STN
visibility of moving pictures, high brightness and high-
enables the addressing of larger numbers of rows and
speed response are very important factors. Currently, the
columns, but the same limitations remain, and the
mainstream of LCD is a TFT-LCD, which belongs to the
inherent generation of interference colour is a further
active matrix category. Typical examples are in-plane
disadvantage. Solving the above problems came with
switching (IPS) mode [3], optically compensated bend
the development of active matrix (AM) addressing of
(OCB) mode [4] and vertical alignment (VA) mode [5].
the twisted nematic device through the use of TFTs.

CONTACT Jianxun Wen wen_jianxun@126.com Fujian Yongjing Technology Co., Ltd., Shaowu, Fujian, China
© 2017 Informa UK Limited, trading as Taylor & Francis Group
2 J. WEN ET AL.

Introduction of fluoro-substituent into molecular struc- CnH2n+1 O a

CnH2n+1
OH
b

ture is very interesting [8]. Many fluorinated liquid crystals A

exhibit single nematic phase and have high voltage holding c
CnH2n+1 CnH2n+1
cis,trans
ratio, large dielectric anisotropy, low birefringence, low B C
viscosity and very good chemical and thermal stability. d e
CnH2n+1 CnH2n+1 I
The fluorosubstituent in organic compounds is considered
D E
to be so interesting because of the combination of polar
and steric effects, and the great strength of the C–F bond, CF3 CF3
F
F F
which confers stability on fluorine-substituted com- f
+ E
g
Cn H2n+1 CF3
pounds. Before the late 1980s, many new synthetic techni- B
Br
HO OH
ques were developed in the research field of fluorinated F G
pharmaceuticals and a lot of synthetic methods obtained
were used to study the commercial applications of the Reagents and conditions (a) PhBr, Mg, THF, 15 ; (b)

fluorinated liquid crystals. The facts show that in the CH3-C6H4-SO3H-H2O,toluene, rt.; (c) Pd/C, toluene, H2, (d) DME,

fluorinated liquid crystals, some fluorosubstituent, includ- t-C4H9OK, room temperature. (e) I2, HIO4, CH3COOH, ClCH2CH2Cl, rt.
ing terminal groups (e.g. CF3, OCF3, OCHF2), have been (f) i-PrMgCl, THF, isopropyl borate . (g) Pd (PPh3) 4, K2CO3 ,C2H5OH.
so successfully and usefully incorporated into liquid crystal
molecules because of the combination of small size and Scheme 1. Synthetic line. Cis and trans express the configura-
tions, respectively. The final reaction is Suzuki cross coupling.
high polarity, and because the high strength of the C–F
bond confers excellent stability. It is unfortunate that the
fluorinated liquid crystal molecules with terminal group
CF3 cannot exhibit good simple useful nematic phase to Results of phase transition and discussion
application in TFT-LCD. The CF3-substituented liquid
The following compounds were abbreviated as Gn
crystals have many advantages, for example, the high
compound (n = 2, 3, 4, 5), respectively.
polarity and low viscosity [9], strong lipophilicity [10],
F
UV resistance [11].
To obtain a kind of new useful liquid crystals for H2n+1Cn CF3
application in TFT LCD, the four ring molecules with
trifluoromethyl substituent were designed and synthe-
n=2,3,4,5
sised. A kind of excellent simple nematic liquid crystal
with very high clearing points was obtained. In this
article, we wish to report the results of the synthesis
and discuss the possible formation mechanism of sin- Observation on textures of G compounds
gle nematic phase on the basis of the principle of
A little powder (G3) was used as sample, the phase
fluorine chemistry [12].
transition and textures of the target compound were
measured by optical microscopy using a polarising
optical microscope equipped with a hot stage. Phase
Synthesis identification was made by comparing the observed
texture. Temperature of observation was 200°C.
The target compounds were a kind of trifluomethyl
The threaded texture (see Figure 1) shows a typical
substituted four ring molecules. The general structure
texture of nematic phase [13].
of the molecules was shown as
The differential scanning calorimetry (DSC).
F
G2 was an example, Figure 2 is the DSC for G2.
CnH2n+1 CF3 The plot of relation between the number of terminal
carbon atoms and transition temperatures were made
n=2,3,4,5
using Table 1.
All compounds Gn exhibit single nematic texture.
They have a broad nematic temperature range of more
The compounds were synthesised according to the than 100°C. The clearing points are very high. It is 267°
following scheme (see Scheme 1): C for G3 compound.
 LIQUID CRYSTALS 3

Table 1. Transition temperatures of compounds Gn.

Compound n Transition temperature (T [°C])
G2 2 Cr 156.73°C N 242.60°C I 241.78°C N 153.70°C Cr
G3 3 Cr 162.21°C N 267.33°C I 266.61°C N 159.45°C Cr
G4 4 Cr 151.54°C N 260.47°C I 259.47°C N 149.02°C Cr
G5 5 Cr 145.95°C N 259.77°C I 258.34°C N 143.11°C Cr
Cr: crystal; N: nematic phase; I: isotropic.

In 1995, the following compound (3,4,5-trifluoro-bicyclo-

hexyl biphenyl) abbreviated to compound F3 was reported
by Demus [16].

Figure 1. (Colour online) The threaded texture of nematic

liquid crystal compound G3. Temperature 200°C,
magnification × 200.

Discussion
The effect of liquid crystal core (bicyclohexyl For the thermal liquid crystal, the so-called meso-
phenyl) on mesomorphic properties morphic property has not a strict definition, and it
only suggests the upper temperature of liquid crystal
In 1985, the following compound abbreviated to com- state in some case. In this case, so-called high meso-
pound F1 was reported by Goto et al. [14]. morphic property shows that the clearing point is
high [17].
The references showed that the clearing points of
compounds F1, F2 and F3 are higher to more than
250°C. This fact illustrates the significant effect of
liquid crystal cores on mesomorphic behaviour. The
comparison between F1 and F2 suggests that the
In 1988, the following compound (3,4-difluoro-bicyclo- increase of polarity is beneficial to the increase of
hexyl biphenyl) abbreviated to compound F2 was mesomorphic behaviour. For the case of F3, meso-
reported by Tanaka et al. [15]. morphic property decreases with the increase of
polarity which was caused by decreasing length to-
breadth ratio. The fact can explain the reason of high
clearing point for G3. The combination of strong
polarity and large length to-breath ratio is beneficial
to the increase of clearing point (see Figure 3).

Figure 2. (Colour online) DSC of compound G2.

4 J. WEN ET AL.

SmB in many fluorinated chain derivatives lies in the

interaction near the chains and a phase separation
occurs, which strongly affects the thermal stability
and layer structure in liquid crystals. Secondly,
because of the mutual interaction between the neigh-
bourhoods of trifluoromethyl partner in the terminal
trifluoromethyl derivatives, the formation of the
molecular layer structures is easy, which is beneficial
to the occurrence of smectic phases. Smart suggested
that there are so-called fluorophilic effects near the
neighbourhood of perfluoroalkyl molecular chains.
The fluorophobic effect between perfluoroalkyl and
hydrocarbon chains exists simultaneously. Because of
the fluorophilic effect, the perfluoroalkyl chains have
a strong tendency to assemble together and forms
Figure 3. (Colour online) The relation between the number partially bilayer with layer structure as a result redu-
of carbon atoms and phase transition temperature of com- cing intermolecular interactions.
pounds Gn.
According to the generalised Van der Waals theory
of nematics, the nematic–isotropic transition (N–I) is
The appearance of single nematic phase for Gn due to the combination of the dispersion force and the
compounds anisotropic excluded volume.
Now we discuss the state change of liquid crystals. In Because of monofluorosubstitution in the next
general, terminal group CF3 causes the appearance of position of trifluoromethyl group in benzene, the
smectic A (SmA) and smectic B (SmB). As to the mutual attraction of terminal groups was reduced.
simultaneous appearance of single N phase and high According to the theory of liquid crystals, the types
clearing point, the relation between the kind of term- of liquid crystals depend on the competition in the
inal fluoro-substituent and state change of liquid intermolecular attraction. If the lateral mutual
crystal has been investigated carefully [18]. The attraction is stronger than the mutual attraction of
interesting results appeared for the following com- terminal groups, the smectic type appears, but in
pounds: the opposite situation nematic-type appears. For
this reason, the phenomenon is easy to understand.

Experimental
Mass spectra were recorded on a G2577A spectro-
A: Z=CF3, C 118 SmA 155 N 174 I
meter. 1H NMR spectra with TMS as internal stan-
B: Z=OCF3 C145 SmA 145 N 204 I
C: Z=OCF2H C 93.5 N 202 I
dard were recorded on a Bruker 400 (400 MHz)
spectrometer. Phase transitions were studied by
thermal polarising optical microscopy (XPV-203E)
Because of the introduction of terminal CF3 group, and a differential scanning calorimeter (Dimand
the strong smectic SmA appears for compounds A and DSC). For the microscopic observation, XPH-300
B. As to difluoromethoxy OCF2H, smectic SmA cannot hot stage was used.
appear. That suggests that in the case, the appearance
of SmA is related to terminal groups only [19,20].
Synthesis of [1’-hydroxy-4’-(trans-4’’-n-butyl
The effect of CF3 group on the change of liquid
cyclohexyl) cyclohexyl]benzene synthesis of 3-
crystal phase is a noticeable in the fluorine chemistry
fluoro-4- trifluoromethyl phenylboronic acid
of liquid crystals. In 2000, Takenaka et al. reported a
(compound A)
detailed review on the fluorine chemistry of liquid
crystals [21]. In this review, the conclusion concern- F
ing the effect of perfluoroalkyl and trifluoromethyl
group on the change of liquid crystal type has been C4 H9 CF3
drawn. The reason of the liable formation of SmA and
 LIQUID CRYSTALS 5

4-Bromo-2-fluoro-trifluoromethylbenzene (6.0 g, pressure. The reaction temperature was maintained

0.099 mol) and anhydrous 10 mL THF were added at 40°C overnight till the reaction was completed.
in 250 mL three-neck flask and 30 mL of a solution of The catalyst was removed by suction filtration and
bromine (14.85 g, 0.094 mol) dissolved in THF was toluene was evaporated (rotary evaporator) affording
slowly added dropwise with stirring while passing cis–trans mixture product about 17.7 g (97%).
nitrogen gas through the flask and maintaining the
reaction temperature at 30–35°C. As a result of the
Synthesis of 4-butyl{(trans, trans-1,1’-bicyclohexyl)-
reaction, the magnesium dissolved in 3 h to form a
4-yl}benzene (D)
uniform brown solution containing phenyl magne-
sium bromide. To 50 mL of a solution of 4-(trans-4ʹ- In 250 mL three-necked flask, the compounds C (cis, trans
butylcyclohexyl) cyclohexanone (20.6 g, 4.085 mol) in forms, 17.67 g) dissolved in 120 mL of DMF and potas-
THF in 250 mL three-neck flask, prepared Grignard sium tertiary butoxide and reflexed under nitrogen gas for
reagent was dropwise added in 40 min while the 5 h. After the transformation of the cis configuration form
reaction temperature was maintained at 5–10°C. into trans form revealed by GC track, the reaction mixture
After the dropping, the mixture was heated up to was cooled to room temperature, and 150 mL water was
35°C and then stirred for 3 h followed by addition added followed to extract by 150 mL toluene twice which
of 20 mL of 10% hydrochloric acid. The reaction was washed by 10% hydrochloric acid solution, saturated
mixture was then transferred to a separating funnel NaHCO3 solution and water and dried (anhydrous mag-
and subjected to extraction with 20 mL hexane, fol- nesium sulphate). The toluene is removed by distillation at
lowed washing the combined organic layers with reduced4 pressure affording solid residue which was
20 mL of saturated solution of NaHCO3, solution of recrystallised from ethanol twice. White solid product
NaCl and water and dried (anhydrous MgSO4). was obtained about 16.7 g (94%).
Removal of the hexane (rotary evaporation) leaves a
residue affording about 26 g solid product Compound C：K tOC4H9 = 1:0.8–1.2 (mol/mol).
(yield 97.1%).
Synthesis of 4-butyl {(trans, trans-1,1’-
Synthesis of [4’-(trans-4’’-n-butylcyclohexyl) bicyclohexyl)-4-yl} iodobenzene
cyclohexen-1’-yl] benzene (compound B) A 100 mL three -necked flask with a condenser is
charged with a mixture of the compound D (5 g,
C4H9 16.8 mol), iodine (3.05 g, 12 mmol), HIO4–2H2O
(3.3 g, 14.5 mmol), acetic acid 8 and 10 mL 1,2-
dichloroethan refluxed with oil bath for 5 h with
In a 250 mL three-necked flask with a Dean-Stark trap stirring. If the reaction was completed, the mixture
and a stirring bar, the compound A (24.5 g, 0.078 mL) and was cooled to room temperature, and 10% solution
p-toluene sulfonic acid–H2O (1.6 g) and 80 mL of toluene of NaHSO3 was added with stirring to remove iodine
were placed. The reaction mixture was reflexed and the residue extracted by toluene. The toluene extract
distillate condensed, which dripped into the trap, where- obtained was washed by salt liquor twice, dried
upon it separated into layers followed to remove the (anhydrous magnesium sulphate) and then the sol-
condensed water from the trap. The combined organic vent was removed by reduced pressure distillation to
phase was washed with saturated NaHCO3 and salting obtain solid residue, which may be recrystallised
liquor and water. The toluene solution was evaporated from mixture solution ethanol:ethyl acetate (10:1) to
(rotary evaporator), affording the solid residue of com- give 5 g (70%).
pound B followed by the recrystallisation from petroleum
to obtained 18 g solid product (yield 78%).
Synthesis of 3-fluoro-4-trifluorophenyl boronic
acid (F)
Synthesis of cis, trans forms mixture 4-bulyl[(cis,
4-Bromo-2-flouro-trifluoromethyl benzene (6.0 g,
trans 1,1’-bicyclohexyl)-4-yl] benzene (compound C)
0.025 mol) dissolved in 10 mL anhydrous THF was
In the high pressure hydrogenation apparatus with placed in a three-neck flask followed to cooling to
mechanical stir, compound B (18 g, 0.061 mol) dis- −20°C. 35 mL i-PrMgCl/THF (0.029 mol) was added
solved in 150 mL of toluene and a Pd/C for catalyst dropwise by dropping funnel for 10 min under nitro-
was placed followed to fill with hydrogen to a desired gen and then temperature was maintained for 2 h.
6 J. WEN ET AL.

Isopropyl borate (5.3 g, 0.028 mol) was added dropwise 4H), 1.17–1.26 (m, 5H), 1.42–1.51 (m, 2H), 1.74–1.96
for 5 min followed to maintain temperature for 2 h. (m, 8H), 2.47–2.55 (m, 1H), 7.32 (d, J = 8.0 Hz, 2H),
After hydrochloric acid (3.65 g, 30%) was added, the 7.42 (q, J = 8.0 Hz, 2H), 7.51 (d, J = 8.4 Hz, 2H), 7.63
reaction was continued for 1 h at −10°C and then the (t, J = 7.8 Hz, 1H); IR (KBr, νmax, cm−1): 3422, 2921,
temperature returned to the room temperature sponta- 2850, 1912, 1626, 1583, 1496, 1432, 1403, 1324, 1252,
neously. THF was removed (rotary evaporator), the 1199, 1131, 1059, 1027, 986, 897, 820, 711, 551.
residue was extracted with ethyl acetate/water, the
organic layer was separated, and aqueous layer was 3-Fluoro-4-trifluoromethyl-4’-[trans, trans-4’’-n-
extracted with ethyl acetate twice. The combined propyl{1,1’-bicyclohexyl}-4-yl]1,1’-biphenyl
organic layer was dried (sodium sulphate), the ethyl (G3) MS (m/z, %): 446 (M+, 100.00), 446 (100.00); 1H
acetate was removed (rotary evaporator), and the resi- NMR (400 MHz, CDCl3): δ 0.86–0.90 (m, 5H), 0.96–
due was recrystallised from n-hexane. The weight of 1.09 (m, 3H), 1.14–1.33 (m, 8H), 1.42–1.51 (m, 2H),
product thus obtained is product is 3.1 g (60%). 1.74–1.96 (m, 8H), 2.47–2.55 (m, 1H), 7.32 (d, J = 8.4
Melting point：248.1–252.8°C; Hz, 2H), 7.42 (q, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz,
MS (m/z, %): 208.0 (M+, 94.32), 144.0 (100.00); 2H), 7.64 (t, J = 8.0 Hz, 1H) IR (KBr, νmax, cm−1): 3446,
1
H NMR (400 MHz, DMSO-D): δ 7.74–7.78 (m, 3H), 2922, 2849, 1913, 1626, 1583, 1496, 1434, 1403, 1324,
8.56 (s, 2H); 1252, 1199, 1131, 1059, 1026, 978, 898, 820, 711, 552.
IR (KBr, νmax, cm−1): 3390, 3316, 1630, 1574, 1515,
1415, 1319, 1138, 1043, 904, 841, 812, 684, 608. 3-Fluoro-4-trifluoromethyl-4’-[trans, trans-4’’-n-
pentyl{1,1’–bicyclohexyl}-4-yl]1,1’–biphenyl
(G5) MS (m/z, %): 474 (M+, 100.00), 474 (100.00). 1H
Suzuki cross-coupling reaction
NMR (400 MHz, CDCl3): δ 0.87–0.90 (m, 5H), 0.96–1.09
In 100 mL three-necked flask, 4-butyl-{(trans, trans-1,1ʹ- (m, 3H), 1.15–1.33 (m, 12H), 1.42–1.51 (m, 2H), 1.74–
bicyclohexyl)-4-yl} iodobenzene (0.57, 1.36 mmol),3- 1.96 (m, 8H), 2.47–2.55 (m, 1H), 7.32 (d, J = 8.4 Hz, 2H),
fluoro,4-trifluoromethyl boric acid (0.3 g, 1.44 mmol), 7.42 (q, J = 8.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.63 (t,
potassium carbonate (0.2 g, 1.45 mmol), Pd(PPh3)4 J = 7.8 Hz, 1H) IR (KBr, νmax, cm−1): 3423, 2921, 2849,
(0.45 g, 0.0375 mmol) was added with stirring by a mag- 1912, 1626, 1584, 1496, 1435, 1403, 1324, 1253, 1199,
netic bar and the temperature maintained at 70°C for 4 h. 1134, 1059, 1027, 979, 898, 820, 712, 55.
The reaction was completed which was filtered by suction
filter to remove potassium carbonate and catalyst. After
the filtrate was extracted by methyl–tertiary butyl ether Conclusion
and water, then the combined organic layer was washed (1) This article reported that trifluoromethyl substi-
five times, dried (magnesium sulphate). The solvent is tuted bicyclohexyl biphenyl is a new type of single
removed (rotary evaporator), and the residue was purified nematic liquid crystals which have very good meso-
by column chromatography on silica gel using petroleum morphic properties, for example of compound G3,
ether as eluent to give white solid 0.5 g. The white solid was exhibits a very high clearing point of 267°C.
recrystallised from ethanol–ethyl acetate (40:1) and 0.34 g (2) In general, in compounds with terminal CF3,
of product was obtained (yield 62%). there exists a strong fluorophilic effect for attrac-
MS (m/z, %): 460.3 (M+, 100.00), 460.3 (100.00); tive force [22], which assembles many molecules
1
H NMR (400 MHz, CDCl3): δ 0.87–0.91 (m, 5H), of liquid crystals to be arranged in layer structure
0.96–1.09 (m, 3H), 1.17–1.29 (m, 10H), 1.42–1.51 (m, of smectic phase. It is suggested that if in the
2H), 1.74–1.96 (m, 8H), 2.47–2.55 (m, 1H), 7.32 (d, neighbourhood of CF3 group, the lateral mono-
J = 8.4 Hz, 2H), 7.42 (dd, J = 8.0 Hz, J = 14.8 Hz, 2H), fluorine on three-position substitution has a con-
7.51 (d, J = 8.0 Hz, 2H), 7.64 (t, J = 7.8 Hz, 1H). siderable effect on the mesomorphic behaviour of
Result of phase transition using DSC the liquid crystals. It was due to the lateral F
Cr 151.5 °C N 260.5°CI 259.5°C N 149.0°C Cr. substituent boarding intermolecular distance
and reducing the intermolecular attraction.
Synthesis for other Gncompounds
3-Fluoro-4-trifluoromethyl-4’-[trans, trans-4’’-n- ethyl
{1,1’-bicyclohexyl}-4-yl]1,1’-biphenyl (G2) Acknowledgement
MS (m/z, %): 432 (M+, 100.00), 432 (100.00); 1H NMR The authors are very grateful to engineer Jixiang Li for his
(400 MHz, CDCl3): δ 0.86–0.89 (m, 5H), 0.96–1.12 (m, help in measurement.
 LIQUID CRYSTALS 7

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