CN1127465C - Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof - Google Patents
Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof Download PDFInfo
- Publication number
- CN1127465C CN1127465C CN 00125736 CN00125736A CN1127465C CN 1127465 C CN1127465 C CN 1127465C CN 00125736 CN00125736 CN 00125736 CN 00125736 A CN00125736 A CN 00125736A CN 1127465 C CN1127465 C CN 1127465C
- Authority
- CN
- China
- Prior art keywords
- compound
- diphenyl
- bis
- fluoric
- ppm
- 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.)
- Expired - Fee Related
Links
Abstract
The present invention relates to a dual-diphenylacetylene compound containing fluorine, which has the molecular formula as the right upper figure, wherein R or R'=C<1 to 12> alkyl radicals; n=0 to 4; A or B is the right lower figure. The present invention is prepared by a Heck reaction or a condensation reaction. The compound has the characteristics of wide liquid crystal phase transition temperature, low viscosity, high birefringence rate, anisotropy, high cleaning point, etc., and furthermore, the compound is new liquid crystal material.
Description
The present invention relates to a kind of fluorine-containing two two benzene-like compounds.This compound bilateral all connects the compound of alkoxyl group.This compound can make respectively by Heck reaction or condensation reaction, is a kind of novel liquid crystal material.
Liquid crystal material needs low melting point, high clearing point, and the mesomorphic phase wide ranges, high birefringence rate, viscosity is low, and is fat-soluble good.Tachibana, Tamon have reported a kind of bis (diphenyl) acetylene nematic phase type liquid crystalline cpd (Jpn.Kokai Tokkyo Koho JP 10130188 A2 19 May 1998), and its principal character is that an end is an alkyl, and the other end is the alkoxyl group side chain.People such as C.S.Hsu reported the bis (diphenyl) acetylene liquid crystalline cpd that utilizes Heck reaction to synthesize to contain the alkyl side chain (Liquid Crystals, 2000, Vol.27, No.2 283-287) is characterized in that two ends are alkyl chain, side direction is the short carbon chain alkyl.We introduce fluorine atom on the basis of two acetylene bond characteristics and tetrafluoro phenyl ring feature primitive has reduced fusing point, have increased nematic temperature range.Because the increasingly extensive application of liquid crystal material, people still expect constantly to explore the liquid crystal material of excellent property.
The purpose of this invention is to provide a kind of new fluoric bis(diphenyl)acetylene compound.Bilateral at compound connects alkoxyl group respectively.
Another object of the present invention provides the method for preparing above-claimed cpd.
Purpose of the present invention also provides above-claimed cpd to be used for the purposes of liquid crystal material.
Fluoric bis(diphenyl)acetylene compound of the present invention has following molecular formula:
R or R '=C wherein
1-12Alkyl, n=0-4, A or
As following compound:
The fluoric bis(diphenyl)acetylene compound of invention can be made respectively by Heck reaction or condensation reaction, further describes as follows:
The fluorine-containing (diphenyl) acetylene compounds that contains bis-alkoxy of the present invention, can by molecular formula be RO-B-C ≡ CH the palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds and molecular formula be I or
Iodide or bromide make through Heck reaction, and reaction formula is: RO-B-C ≡ CH+I or
Wherein R, R, n and A and B are all ditto described.
Specifically, above-mentioned palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds, halogenide is at palladium compound, CuX and amine organic solvent exist down, in room temperature to reflux temperature, reaction 0.5-100h, the above-claimed cpd mol ratio is followed successively by 1: 1-10: 0.01-0.2: 0.02-0.40: 0-100.Described palladium compound is two (trihydrocarbyl phosphine) dihalide palladium, two (trihydrocarbyl phosphine) palladium, and two (trihydrocarbyl phosphine) Palladous nitrate, described amine organic solvent is to have C
1-12The tertiary amine of alkyl, secondary amine, primary amine, pyridine, bipyridine etc.The having of amine organic solvent helps the carrying out that react, and the mol ratio of above-mentioned halogenide and amine organic solvent is recommended as 1: 1-10, recommend to use triethylamine.
Fluoric bis(diphenyl)acetylene compound of the present invention is simple synthetic method not only, and is a kind of good STN and TFT liquid crystal display material.Have low melting point, high clearing point, the mesomorphic phase wide ranges, the chemical stability height, the degree of birefringence height, characteristics such as response speed is fast are suitable for suitability for industrialized production and application.
The present invention will be helped to understand by following embodiment, but content of the present invention can not be limited.
Embodiment 1
Preparation: will
Or I200mg,
100-200mg, two (triphenylphosphine) Palladous chlorides or palladium 5-15mg, CuI10-20mg, triethylamine or Di-Octyl amine 5-20ml stir 10-24h in room temperature to 70oC, high pressure liquid chromatography or fluorine spectrum track to reaction and finish, filter, add organic solvent extraction, the organic phase dried over sodium sulfate, boil off solvent, column chromatography for separation.The result is as shown in the table:
Compound 1:
1HNMR (CDCl
3/ TMS) δ
H7.53-6.87 (m, 10H), 3.98 (t, 4H, J=5.3Hz), 1.98-0.87 (m, 16H) ppm.
19FNMR (CDCl
3/ TFA) δ F 30.6 (m, 2F) ppm. MS (m/z, %): 472 (M
+, 15.55), 109 (100.0). ultimate analysis: theoretical (%) C78.79 H6.40 F8.04. actual measurement (%) C78.85H6.50F7.63. compound 2:
1HNMR (CDCl
3/ TMS) δ
H7.57-6.33 (m, 10H), 3.98 (t, 4H, J=5.7Hz), 2.02-0.73 (m, 18H) ppm.
19FNMR δ
F30.7 (m, 2F) ppm.MS (m/z, %): 486 (M
+, 100.0). ultimate analysis: theoretical (%) C78.99 H6.63 F7.81. actual measurement (%) C79.15 H6.74 F7.54 compound 3:
1HNMR (CDCl
3/ TMS) δ
H7.47-6.84 (m, 10H), 4.00 (t, 4H, J=5.9Hz), 2.00-0.85 (m, 22H) ppm.
19FNMR (CDCl
3/ TFA) δ
F31.0 (m, 2F) ppm.MS (m/z, %): 514 (M
+, 100.0). ultimate analysis: theoretical (%) C79.35 H7.05 F7.38. actual measurement (%) C79.53 H7.21 F7.16. compound 4:
1HNMR (CDCl
3/ TMS) δ
H7.57-6.80 (m, 10H), 3.99 (t, 4H, J=5.9Hz), 1.99-0.85 (m, 24H) ppm.
19FNMR (CDCl
3/ TFA) δ
F31.0 (m, 2F) ppm.MS (m/z, %): 528 (M
+, 100.0). ultimate analysis: theoretical (%) C79.52 H7.24 F7.19. actual measurement (%) C79.60 H7.22 F7.18. compound 5:
1HNMR (CDCl
3/ TMS) δ
H7.50-6.80 (m, 10H), 4.01 (t, 4H, J=5.9Hz), 2.02-0.65 (m, 32H) ppm.
19FNMR (CDCl
3/ TFA) δ
F30.8 (m, 2F) ppm.MS (m/z, %): 584 (M
+, 100.0). ultimate analysis: theoretical (%) C 80.10 H7.93F6.50. actual measurement (%) C79.97 H7.89 F6.59
Sequence number | R | Productive rate % |
1 2 3 4 5 | C4H9 C5H11 C7H15 C8H17 C12H25 | 70 67 71 69 63 |
Embodiment 2
Preparation will
Or I 200mg,
100-200mg, two (triphenylphosphine) Palladous chloride 5-15mg, CuI 10-20mg adds triethylamine or pyridine 10mL, stirs 10-24h in room temperature to 70oC, and product concentrates through column chromatography for separation.The result is as follows:
Compound 6
1HNMR (CDCl
3/ TMS) δ
H7.42-6.80 (m, 6H), 4.34 (s, 3H), 4.00 (t, 2H, J=5.5Hz), 2.01-0.75 (m, 9H) ppm.
19FNMR (CDCl
3/ TFA) δ
F29.6 (m, 2F), 60.0 (m, 2F), 79.9 (m, 2F) ppm.MS (m/z, %): 502 (M
+, 56.78), 418 (100.0). ultimate analysis: theoretical (%) C66.93 H4.01 F22.69. actual measurement (%) C66.85 H4.15 F22.60. compound 7
1HNMR (CDCl
3/ TMS) δ
H7.52-6.85 (m, 6H), 4.31 (t, 2H, J=5.8Hz), 4.00 (t, 2H, J=5.5Hz), 2.01-0.75 (m, 16H) ppm.
19FNMR (CDCl
3/ TFA) δ
F29.8 (m, 2F), 59.7 (m, 2F), 79.7 (m, 2F) ppm.MS (m/z, %): 544 (M
+, 56.77), 418 (100.0). ultimate analysis: theoretical (%) C68.38 H4.81 F20.93. actual measurement (%) C68.53 H4.72 F20.72. compound 8
1HNMR (CDCl
3/ TMS) δ
H7.56-6.90 (m, 6H), 4.34 (t, 2H, J=5.8Hz), 4.03 (t, 2H, J=5.7Hz), 2.03-0.80 (m, 18H) ppm.
19FNMR (CDCl
3/ TFA) δ
F29.7 (m, 2F), 60.2 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 558 (M
+, 56.77), 418 (100.0). ultimate analysis: theoretical (%) C68.81 H5.05. actual measurement (%) C68.63 H5.15. compound 9
1HNMR (CDCl
3/ TMS) δ
H7.50-6.83 (m, 6H), 4.27 (t, 2H, J=5.9Hz), 3.98 (t, 2H, J=5.4Hz), 1.92-0.72 (m, 20H) ppm.
19FNMR (CDCl
3/ TFA) δ
F29.5 (m, 2F), 60.0 (m, 2F), 79.9 (m, 2F) ppm.MS (m/z, %): 572 (M
+, 56.13), 418 (100.0). ultimate analysis: theoretical (%) C69.22 H5.28 F19.91. actual measurement (%) C68.99 H5.25 F20.40. compound 10
1HNMR (CDCl
3/ TMS) δ
H7.54-6.87 (m, 6H), 4.30 (t, 2H, J=5.6Hz), 3.99 (t, 2H, J=5.4Hz), 1.97-0.75 (m, 22H) ppm.
19FNMR (CDCl
3/ TFA) δ
F29.8 (m, 2F), 59.9 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 586 (M
+, 73.48), 418 (100.0). ultimate analysis: theoretical (%) C69.62 H5.50 F19.43. actual measurement (%) C69.74 H5.42 F19.61. compound 11
1HNMR (CDCl
3/ TMS) δ
H7.53-6.86 (m, 6H), 4.30 (t, 2H, J=5.4Hz), 4.00 (t, 2H, J=5.8Hz), 1.94-0.77 (m, 24H) ppm.
19FNMR (CDCl
3/ TFA) δ
F30.0 (m, 2F), 60.3 (m, 2F), 80.4 (m, 2F) ppm.MS (m/z, %): 600 (M
+, 67.68), 418 (100.0). ultimate analysis: theoretical (%) C69.99 H5.71 F18.98. actual measurement (%) C70.11 H5.79 F19.25.
Sequence number | R | Productive rate % |
6 7 8 9 10 11 | CH 3 C 4H 9 C 5H 11 C 6H 13 C 7H 15 C 8H 17 | 76 72 70 80 68 73 |
Embodiment 3
Preparation: adopt
Or I and
Be raw material, operation is with embodiment 1, and the result is as follows:
Compound 12
1HNMR (CDCl
3/ TMS) δ
H7.55-6.85 (m, 8H), 4.30 (t, 2H, J=5.3Hz), 4.00 (t, 2H, J=5.8Hz), 2.57-0.80 (m, 16H) ppm.
19FNMR (CDCl
3/ TFA) δ
F60.9 (m, 2F), 80.4 (m, 2F) ppm.MS (m/z, %): 508 (M
+, 89.67), 382 (100.0). ultimate analysis: theoretical (%) C73.23 H5.51 F14.96. actual measurement (%) C73.44 H5.57 F14.87. compound 13
1HNMR (CDCl
3/ TMS) δ
H7.48-6.76 (m, 8H), 4.25 (t, 2H, J=5.2Hz), 3.96 (t, 2H, J=5.9Hz), 2.03-0.73 (m, 18H) ppm.
19FNMR (CDCl
3/ TFA) δ
F60.2 (m, 2F), 80.0 (m, 2F) ppm.MS (m/z, %): 522 (M
+, 100.0). ultimate analysis: theoretical (%) C73.56 H5.75 F14.56. actual measurement (%) C73.65 H5.88 F14.61. compound 14
1HNMR (CDCl
3/ TMS) δ
H7.55-6.80 (m, 8H), 4.23 (t, 2H, J=5.4Hz), 3.93 (t, 2H, J=5.9Hz), 1.95-0.70 (m, 20H) ppm.
19FNMR (CDCl
3/ TFA) δ
F60.4 (m, 2F), 80.3 (m, 2F) ppm.MS (m/z, %): 536 (M
+, 82.59) and 382 (100.0). ultimate analysis: theoretical (%) C73.87 H6.01 F14.16. actual measurement (%) C73.60 H6.04 F14.27. compound 15
1HNMR (CDCl
3/ TMS) δ
H7.57-6.95 (m, 8H), 4.30 (t, 2H, J=5.3Hz), 4.00 (t, 2H, J=5.7Hz), 2.01-0.75 (m, 22H) ppm.
19FNMR (CDCl
3/ TFA) δ
F60.8 (m, 2F), 80.6 (m, 2F) ppm.MS (m/z, %): 550 (M
+, 13.21) and 57 (100.0). ultimate analysis: theoretical (%) C74.16 H6.22 F13.80 actual measurement (%) C74.25 H6.27 F14.14. compound 16
1HNMR (CDCl
3/ TMS) δ
H7.55-6.85 (m, 8H), 4.28 (t, 2H, J=5.3Hz), 3.98 (t, 2H, J=5.8Hz), 1.97-0.60 (m, 24H) ppm.
19FNMR (CDCl
3/ TFA) δ
F60.8 (m, 2F), 80.5 (m, 2F) ppm.MS (m/z, %): 564 (M
+, 100.0). ultimate analysis: theoretical (%) C74.45 H6.43 F13.46 actual measurement (%) C74.69 H6.13 F13.48.
Sequence number | R | Productive rate % |
12 13 14 15 16 | C 4H 9 C 5H 11 C 6H 13 C 7H 15 C 8H 17 | 63 68 59 58 64 |
Embodiment 4
Preparation: adopt
With
Be raw material, operation is with embodiment 2, and its result is as follows:
Compound 17
1HNMR (CDCl
3/ TMS) δ
H7.47-6.78 (m, 6H), 4.20 (t, 2H, J=5.2Hz), 3.95 (t, 2H, J=5.9Hz), 2.05-0.73 (m, 18H) ppm.
19FNMR (CDCl
3/ TFA) δ
F56.0 (m, 1F), 60.6 (m, 2F), 80.6 (m, 2F), 81.5 (1F, m) ppm..MS (m/z, %): 558 (M
+). ultimate analysis: theoretical (%) C68.81 H5.05 F20.41. actual measurement (%) C68.70 H5.25 F20.11. compound 18
1HNMR (CDCl
3/ TMS) δ
H7.49-6.80 (m, 6H), 4.28 (t, 2H, J=5.4Hz), 3.99 (t, 2H, J=5.9Hz), 1.98-0.60 (m, 24H) ppm.
19FNMR (CDCl
3/ TFA) δ
F55.7 (m, 1F), 60.9 (m, 2F), 80.4 (m, 2F), 81.8 (1F, m) ppm..MS (m/z, %): 600 (M
+). ultimate analysis: theoretical (%) C69.99 H5.71 F18.98. actual measurement (%) C70.11 H5.57 F18.77. compound 19
1HNMR (CDCl
3/ TMS) δ
H7.55-6.82 (m, 6H), 4.28 (t, 2H, J=5.3Hz), 4.07 (t, 2H, J=5.7Hz), 1.98-0.65 (m, 30H) ppm.
19FNMR (CDCl
3/ TFA) δ
F55.9 (m, 1F), 61.0 (m, 2F), 80.1 (m, 2F), 81.7 (1F, m) ppm..MS (m/z, %): 624 (M
+). ultimate analysis: theoretical (%) C71.01 H6.27 F17.74 actual measurement (%) C71.12 H6.08 F17.90. compound 20
1HNMR (CDCl
3/ TMS) δ
H7.52-6.75 (m, 6H), 4.27 (t, 2H, J=5.3Hz), 3.99 (t, 2H, J=5.8Hz), 2.05-0.56 (m, 34H) ppm.
19FNMR (CDCl
3/ TFA) δ
F55.8 (m, 1F), 60.8 (m, 2F), 80.5 (m, 2F), 81.6 (1F, m) ppm.MS (m/z, %): 670 (M
+). ultimate analysis: theoretical (%) C71.62 H6.61 F16.99 actual measurement (%) C71.80 H6.33 F16.80.
Sequence number | R | Productive rate % |
17 18 19 20 | C 3H 7 C 6H 13 C 9H 19 C 11H 23 | 55 57 49 50 |
Embodiment 5
Preparation: adopt
Be raw material, operation is with embodiment 2.Obtain compound 21 with 68% productive rate.Compound 21:
1HNMR (CDCl
3/ TMS) δ
H7.74-6.80 (m, 10H), 4.21 (t, 2H, J=5.4Hz), 3.94 (t, 2H, J=5.9Hz), 1.98-0.60 (m, 18H) ppm.
19FNMR (CDCl
3/ TFA) δ
F55.8 (m, 1F), 81.7 (1F, m) ppm..MS (m/z, %): 486 (M
+). ultimate analysis: theoretical (%) C78.99 H6.63 F7.81. actual measurement (%) C78.91 H6.44 F7.98.
Embodiment 6
Preparation: adopt
Or I and
Be raw material.Operation makes through the Heck reaction with embodiment 1.Compound 22:
1HNMR (CDCl
3/ TMS) δ
H7.52-6.75 (m, 7H), 4.24 (t, 2H, J=5.3Hz), 3.89 (t, 2H, J=5.8Hz), 2.05-0.56 (m, 30H) ppm.
19FNMR (CDCl
3/ TFA) δ
F55.9 (m, 1F), 60.6 (m, 2F), 80.6 (m, 2F) ppm.MS (m/z, %): 643 (M
+). ultimate analysis: theoretical (%) C70.90 H6.42 F17.71 actual measurement (%) C70.78 H6.33 F17.90.
Embodiment 7
Preparation: adopt
Or Br and
Be raw material.Operation makes through the Heck reaction with embodiment 1.Compound 23
1HNMR (CDCl
3/ TMS) δ
H7.23 (m, 2H), 3.89 (s, 6H) ppm.
19F NMR (CDCl
3/ TFA) δ
F29.7 (m, 2F), 59.8 (m, 4F), 80.1 (m, 4F) ppm.MS (m/z, %): 518 (M
+). ultimate analysis: theoretical (%) C55.62 H1.56 F36.65 actual measurement (%) C55.74 H1.33 F36.50.
Embodiment 8
With orthogonal polarizing microscope the part of compounds of embodiment 1 to 7 is carried out phase research, the phase transition property that in heating and cooling process, occurs.During their transformation behavior was listed in the table below, wherein Cr represented crystal, and N represents nematic phase, and I represents anisotropic liquid, and Recr represents crystallization.The mesomorphic phase scope of this compounds is very wide as can be seen from the table.
The compound sequence number | Phase transition property |
1 2 3 4 7 8 9 10 11 | Cr 115.0 N 214.3 I 212.6 N 110.1 Recr Cr 103.9 N 203.1 I 201.5 N 93.0 Recr Cr 97.8 N 195.4 I 194.1 N 89.4 Recr Cr 94.5 N 191.5 I 190.1 N 82.2 Recr Cr 109.4 N 201.1 I 199.6 N 102.7 Recr Cr 102.5 N 191.8 I 190.5 N 95.4 Recr Cr 101.1 N 186.7 I 185.4 N 95.6 Recr Cr 99.3 N 179.5 I 178.5 N 93.0 Recr Cr 101.8 N 176.1 I 174.4 N 94.8 Recr |
12 13 14 15 16 | Cr 82.5 N 211.0 I 209.8 N 74.4 Recr Cr 70.2 N 196.8 I 194.6 N 53.9 Recr Cr 70.8 N 196.4 I 195.0 N 62.1 Recr Cr 91.1 N 188.7 I 187.5 N 66.9 Recr Cr 101.4 N 184.5 I 183.4 N 87.0 Recr |
Claims (7)
2. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 1, it is characterized in that with by molecular formula be RO-B-C ≡ CH the palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds and molecular formula be I or
Iodide or bromide, at palladium compound, CuX and amine organic solvent exist down, make through the HecK reaction, wherein R, R ', n and A and B are according to claim 1.
3. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2, it is characterized in that described palkoxy benzene acetylene compound or to alkoxyl group perfluor phenylacetylene compounds, iodide or bromide are at palladium compound, CuX and amine organic solvent exist down, in room temperature to reflux temperature, reaction 0.5-100h, described compound mol ratio is followed successively by 1: 1-10: 0.01-0.2: 0.02-0.40: 0-100.
4. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described palladium compound is two (trihydrocarbyl phosphine) dihalide palladium, two (trihydrocarbyl phosphine) palladium, two (trihydrocarbyl phosphine) Palladous nitrate.
5. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described amine organic solvent is to have C
1-12The tertiary amine of alkyl, secondary amine, primary amine, pyridine, bipyridine,
6. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that the mol ratio of described halogenide and amine organic solvent is 1: 1-10.
7. the method for the preparation of fluoric bis(diphenyl)acetylene compound as claimed in claim 2 is characterized in that described amine organic solvent is a triethylamine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00125736 CN1127465C (en) | 2000-10-20 | 2000-10-20 | Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00125736 CN1127465C (en) | 2000-10-20 | 2000-10-20 | Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1293180A CN1293180A (en) | 2001-05-02 |
CN1127465C true CN1127465C (en) | 2003-11-12 |
Family
ID=4591520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 00125736 Expired - Fee Related CN1127465C (en) | 2000-10-20 | 2000-10-20 | Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1127465C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3974093B2 (en) * | 2003-08-21 | 2007-09-12 | シャープ株式会社 | Display device |
US8420235B2 (en) * | 2009-06-04 | 2013-04-16 | Nitto Denko Corporation | Emissive diaryl acetylenes |
DE102011112950A1 (en) * | 2010-10-13 | 2012-04-19 | Merck Patent Gmbh | Compounds for a liquid-crystalline medium and their use for high-frequency components |
CN102603568A (en) * | 2011-11-28 | 2012-07-25 | 北京科技大学 | Fluorine-containing bis-diphenylacetylene liquid crystal compound and preparation method thereof |
CN104531165B (en) * | 2014-12-12 | 2016-10-05 | 西安彩晶光电科技股份有限公司 | Two fluoro-[(4-alkoxyl-2,3,5,6-tetrafluoro phenyl) ethyl)-side fluorophenyl-side fluoro-4-4-trifluoromethylphenopendant] methane and preparation and application thereof |
-
2000
- 2000-10-20 CN CN 00125736 patent/CN1127465C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN1293180A (en) | 2001-05-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6797544B2 (en) | Fluorinated dibenzofuran and dibenzothiophene derivatives | |
JP2873096B2 (en) | Liquid crystal composition and liquid crystal display device | |
JP4876420B2 (en) | Difluorobenzene derivative | |
JP6493678B2 (en) | Liquid crystalline compound, liquid crystal composition and liquid crystal display device | |
WO1998013324A1 (en) | Fluoroalkylated liquid-crystal compounds, liquid-crystal compositions, and liquid-crystal display elements | |
JP3273441B2 (en) | Liquid crystal composition and liquid crystal display device | |
CN1127465C (en) | Fluoric bis(diphenyl)acetylene compounds and preparing process and usage thereof | |
US6180027B1 (en) | Bisalkenyl derivatives, liquid crystalline compounds and liquid crystal compositions | |
JP2003286217A (en) | Liquid crystalline compound having naphthalene ring, liquid crystal composition and liquid crystal display element | |
CN100509724C (en) | Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, preparation method and use thereof | |
KR19990045693A (en) | Nematic liquid crystal composition containing fluorine-substituted 4-alkenylbenzoic acid and its derivatives and benzoic acid cyanophenyl ester derivatives and liquid crystal display using the same | |
JPH0867641A (en) | Diene compound and liquid crystal medium | |
TW457290B (en) | Liquid crystalline compound having a piperidine ring, liquid crystal composition and liquid display element | |
CN102557896B (en) | (Poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and preparation method and application thereof | |
EP0581272B1 (en) | Tolane derivatives, liquid crystal compositions containing the derivatives and liquid crystal display device using the compositions | |
WO1998035924A1 (en) | Liquid-crystalline compounds having bicyclo[1.1.1]pentane structure, liquid-crystal composition, and liquid-crystal display element | |
TW445291B (en) | Ester compounds, liquid crystal compositions and liquid crystal display devices | |
JP2011074010A (en) | Difluorobenzene derivative, and liquid crystal composition comprising the same | |
JP3783247B2 (en) | 1,2-dicyclohexylpropane derivative | |
CN112457865A (en) | Liquid crystal compound and composition and application thereof | |
JP4385202B2 (en) | Phenyldecahydronaphthalene derivative | |
JP4973911B2 (en) | Chroman derivative and liquid crystal composition containing the compound | |
JP3899530B2 (en) | Liquid crystal compound and liquid crystal composition | |
JP5011623B2 (en) | Novel liquid crystalline compound having 1,2-propanediyl group as linking group and liquid crystal composition containing the same | |
EP0982387A1 (en) | Liquid crystal compound having negative dielectric anisotropy, liquid crystal composition containing said liquid crystal compound and liquid crystal display device using said composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |