CN109575937A - A kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds and preparation method thereof - Google Patents
A kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of truxene ketone-benzophenanthrene discotic mesogenic organic semiconducting materials and preparation method thereof; the method is that single bromine benzophenanthrene and potassium carbonate are added to N; in N '-dimethyl formamide; under inert gas protection; trihydroxy truxene compound is added; it is heated to 80 DEG C to be stirred to react 36 ~ 48 hours, then removes gas shield, then reaction system is open in air and continues heating reaction 24 ~ 36 hours；After fully reacting, reaction solution is cooled to room temperature, is poured into ice water, that is, have red solid precipitation, suction filtration obtains crude product, is dried in vacuo, and then uses column chromatography purifying, and methylene chloride makees eluant, eluent, last mixed organic solvents recrystallization, and vacuum drying obtains.Synthetic method of the present invention is easy to operate, and reaction condition is mild, and yield is moderate, and a step, which has connected to be etherified building polymer and aoxidize, obtains the reaction of truxene ketone, successfully synthesizes p-n junction disc liquid-crystal compounds.A kind of high efficiency preparation method is provided for more complex truxene ketone derivatives.
Description
Technical field
The invention belongs to organic photoelectric functional material technical field, in particular to a kind of truxene ketone-benzophenanthrene plate-like liquid
The molecular structure of brilliant organic semiconducting materials and preparation method thereof, such material is as follows:
Background technique
As the newcomer in organic semiconducting materials, it has self assembly order, can review one's lessons by oneself discotic mesogenic semiconductor
Its multiple fault of construction, there is the unique performances such as higher anisotropy charge mobility.Discotic mesogenic semiconductor is imitated in organic field
The application and development in the fields such as transistor, organic solar batteries is answered, the attention of researcher is just being increasingly subject to.Discotic liquid crystal polymer
Determination molecular weight with such as unimolecule compound, and it is different from unimolecule, easily there is the film forming characteristics and glass of similar high polymer
Glass state structure.Benzophenanthrene, truxene and truxene ketone are typical plate-like mesomorphic units, and the benzophenanthrene of electron rich, truxene are spread out
Biology is frequently as p-type organic lcd semiconductor material, and the truxene ketone derivatives of opposite electron-deficient are frequently as n-type semiconductor material
Material.(just own sulfenyl) the benzophenanthrene disc liquid-crystal compounds TP of 2,3,6,7,10,11- six (SC6H13)6Can accumulate to be formed it is spiral helicine
Hexagonal columnar phase, flight time measuring technology test its hole mobility in liquid crystal state and are up to 0.1 cm2·V-1·s-1。
3,8,13- tri- (n-octyloxy) truxene disc liquid-crystal compounds TR (OC8H17)3Hexagonal columnar phase with high-sequential,
Hole migration rate in liquid crystal state can also reach 7.5 × 10-2 cm2·V-1·s-1, the carrier close to unformed silicon moves
Move rate level.Peking University Pei Jian etc. once synthesizes C3Symmetrically contain the truxene and single point of truxene ketone plate-like of three ether chains
Sub- liquid-crystal compounds, there are apparent electron donor and acceptor interactions for the two compound, can form one-dimensional hybrid structure,
It is p-n junction modulation material [Wang, the J. Y. for potentially preparing photoelectric device; Yan, J.; Li, Z. D.; Han, J.
M.; Ma Y. G.; Bian, J.; Pei. J. Chem. Eur. J., 2008, 14, 7760-7764.].Electron rich is rigid
Property core be connected with electron-deficient rigid nuclear by flexible chain the D-A type polymer formed, since it had not only contained electron donor, but also containing power supply
Daughter, therefore existing electron propagation ducts have hole migrating channels again in a molecule, have in organic electro-optic device latent
Application value.D-A type discotic liquid crystal polymer is rarely reported.
The preparation of truxene ketone derivatives is to eliminate the hydrogen bromide trimerization cyclization side of synthesis at high temperature by bromo indone earliest
Method directly synthesizes tribromo truxene ketone, yield only 20%[Christoph, L.; Gilbert, N.; Elmar S.; Klaus,
M.; Christoph, B. Chem. Eur. J., 1998, 4, 2129-2135.].Truxene ketone derivatives are mainly logical
Corresponding truxene derivative oxidation preparation is crossed, truxene derivative is especially unstable in the solution, is easy by the oxygen in air
It is gradually oxidized to spit alkene former times ketone derivatives.Pei Jian etc. once made alkali in potassium carbonate by 3,8,13- trihydroxy truxenes and bromoalkane, N,
N '-dimethyl formamide is made under solvent condition, is heated to that etherificate and oxidation one step tandem reaction preparation occur at 100 DEG C in air
3,8,13- tri- (positive hexyloxy) truxene ketone, but yield only reaches 36%；In addition they also attempt using two-step reaction process,
First trihydroxy truxene and bromoalkane make alkali in potassium carbonate, under the conditions of ethanol as solvent, are heated to that ether occurs at 100 DEG C in air
Change reaction and generate 3,8,13- tri- (positive hexyloxy) truxenes, yield 51%, then make alkali in tetramethylammonium hydroxide, tetrahydrofuran is made
Under solvent condition, reflux generation oxidation reaction obtains 3,8,13- tri- (positive hexyloxy) truxene ketone [Wang, J. in oxygen atmosphere
Y.; Yan, J.; Ding, L.; Ma, Y. G.; Pei, J. Adv. Funct. Mater., 2009, 19, 1746–
1752.].To sum up, the synthetic method of existing preparation synthesis truxene ketone derivatives is inefficient, spits former times especially for more complex
The synthesis of ketenes derivative needs to further investigate.
Summary of the invention
An object of the present invention is to provide a kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds.
Another goal of the invention of the invention is to provide a kind of preparation method of more complex truxene ketone derivatives, i.e., a kind of
Truxene ketone-benzophenanthrene discotic liquid crystal polymer preparation method.
One kind truxene ketone-benzophenanthrene disc liquid-crystal compounds provided by the invention, which is characterized in that the compound tool
There is the structure of the following general formula (I), wherein R is straight chained alkyl-C m H2m+1, mIndicate carbon atom number be 4 ~ 8 integer, as normal-butyl,
N-pentyl, n-hexyl, n-heptyl, n-octyl,nIndicate the methylene number of flexible connection chain:
Logical formula (I)
In order to achieve the above objectives, the present invention devises following reaction process:
According to above-mentioned reaction process, the present invention provides the preparation side of truxene ketone-benzophenanthrene disc liquid-crystal compounds a kind of in this way
Method, the processing step and condition of this method are as follows:
Compound list bromine benzophenanthrene and potassium carbonate are added to N, in N '-dimethyl formamide, stirred at room temperature, simultaneously to single bromobenzene
Phenanthrene is completely dissolved；Then under inert gas protection, trihydroxy truxene compound is added, be heated to 80 DEG C be stirred to react 36 ~
48 hours, gas shield is removed later, then reaction system is open in air and is continued heating reflux reaction 24 ~ 36 hours；
After fully reacting, reaction solution is cooled to room temperature, is poured into ice water, that is, have red solid precipitation, suction filtration obtains crude product, and vacuum is dry
It is dry, purifying is then used column chromatography, methylene chloride makees eluant, eluent, last mixed organic solvents recrystallization, and vacuum drying obtains
Product.
The molar ratio of trihydroxy truxene in the method, single bromine benzophenanthrene and potassium carbonate be 1: 3 ~ 4: 6 ~
10。
The organic solvent of recrystallization is the mixed solvent of ethyl acetate and ethyl alcohol volume ratio 1: 5 in the method.
In the method shown in the structure such as general formula (II) of single bromine benzophenanthrene:
General formula (II)
Trihydroxy truxene structure is shown below in the method:
。
Compared with prior art, the present invention having the advantage that
1, a kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds provided by the invention are a kind of D-A type polymer, room temperature plate-like
Liquid crystal.Its chemical and thermal stability is preferable, has wide mesomorphic phase temperature range, the hexagonal columnar liquid crystal of high-sequential is presented
Phase can be used as the p-n junction modulation material for potentially preparing photoelectric device.
2, the preparation method of a kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds provided by the invention, the synthetic method
Easy to operate, reaction condition is mild, and yield is moderate, and a step has connected to be etherified building polymer and aoxidize and obtained spitting the anti-of alkene former times ketone
It answers.A kind of high efficiency preparation method is provided for more complex truxene ketone derivatives.
Detailed description of the invention
Fig. 1 is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-n- TP) thermogravimetric analysis (TGA) curve graph.
Fig. 2-a is that truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) differential scanning calorimetry (DSC) is surveyed
The thermal analysis curve figure of examination;Fig. 2-b is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) differential scanning amount
The thermal analysis curve figure of thermal method (DSC) test;Fig. 2-c is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP)
Differential scanning calorimetry (DSC) test thermal analysis curve figure.
Fig. 3-a is Polarized Texture when truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) are cooled to 168 DEG C
Figure；Fig. 3-b is Polarized Texture figure when truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) are cooled to 158 DEG C；
Fig. 3-c is Polarized Texture figure when truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP) are cooled to 147 DEG C.
Fig. 4 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) nuclear magnetic resonance spectroscopy (1HNMR) figure.
Fig. 5 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) carbon-13 nmr spectra (13CNMR) figure.
Fig. 6 is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) high resolution mass spectrum (HRMS) figure.
Fig. 7 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) nuclear magnetic resonance spectroscopy (1HNMR) figure.
Fig. 8 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) carbon-13 nmr spectra (13CNMR) figure.
Fig. 9 is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) high resolution mass spectrum (HRMS) figure.
Figure 10 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP) nuclear magnetic resonance spectroscopy (1HNMR)
Figure.
Figure 11 be truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP) carbon-13 nmr spectra (13CNMR)
Figure.
Figure 12 is truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP) high resolution mass spectrum (HRMS) figure.
Specific embodiment
Embodiment is given below so that the present invention to be specifically described, it is necessary to which indicated herein is that following embodiment is only used
In invention is further explained, it should not be understood as limiting the scope of the invention, the people that is skilled in technique of this field
Member still belongs to protection model of the invention according to some nonessential modifications and adaptations that the content of aforementioned present invention makes the present invention
It encloses.
It is worth noting that initial reactant list bromine benzophenanthrene used in following embodiment is bibliography Yu, W.-
H.; Chen, C.; Hu, P.; Wang, B. Q.; Redshaw, C.; Zhao, K.-Q. RSC. Adv., 2013,
3,14099-14105. disclosed method preparation；Trihydroxy truxene is bibliography (1) Ni, H.-L.; Monobe, H.;
Hu, P.; Wang, B.-Q.; Shimizu, Y.; Zhao, K.-Q. Liq. Cryst., 2013, 40, 411-420.
Disclosed synthetic method preparation.
Embodiment 1
The synthesis of truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP)
By single bromine benzophenanthrene TP (OC6H13)5(OCH2)6Br (102 mg, 0.112 mmol), and potassium carbonate (80 mg, 0.58
Mmol), 15 mL N, N '-dimethyl formamide are added in 25 mL round-bottomed flasks, stir at room temperature, complete to single bromine benzophenanthrene
Fully dissolved under inert gas shielding, is added trihydroxy truxene compound (30 mg, 0.035 mmol), 80 DEG C of heating stirring,
It reacts and removes protection after 36 h, reaction system is open in air that the reaction was continued for 24 hours.TLC contact plate tracks to fully reacting, will
Reaction solution is cooled to room temperature, pours into ice water, that is, has red solid precipitation, and suction filtration obtains crude product, is dried in vacuo, and then uses column layer
Analysis isolates and purifies, and methylene chloride makees eluant, eluent, and the mixed solvent recrystallization of ethyl acetate and ethyl alcohol volume ratio 1: 5 obtains red
71 mg of color solid, yield 61%.
Infrared FT-IR:(KBr) νmax 2928, 2857, 1694, 1617, 1576, 1514, 1467, 1262,
1169, 1040, 861 cm-1;Nucleus magnetic hydrogen spectrum1H NMR (400 MHz, CDCl3) δ 8.76 (s, 3H, ArH),
7.75-7.69 (m, 18H, ArH), 7.18 (s, 3H, ArH), 4.29-4.26 (t, J = 6.4 Hz, 6H, 3×
OCH2), 4.23-4.10 (m, 42H, 14×OCH2), 2.01-1.85 (m, 48H, 16×CH2), 1.71-0.92
(m, 144H, 48×CH2), 0.94-0.90 (t, J = 8.0 Hz ,45H, 15×CH3), 0.87-0.83 (t, J =
8.0, 9H, 3×CH3);Nuclear-magnetism carbon spectrum13C NMR (100 MHz, CDCl3) δ 191.15, 154.22, 151.17,
148.76, 136.66, 130.07, 123.45, 111.62, 107.18, 106.87, 106.45, 69.63, 69.42,
69.17, 68.96, 68.71, 31.94, 31.73, 29.70, 29.63, 29.53, 29.48, 29.43, 29.41,
29.20, 29.07, 26.22, 25.89, 25.86, 25.84, 25.51, 25.39, 22.71, 22.68, 14.14,
14.08;High resolution mass spectrum HRMS (MALDI) m/z:[M]+ Calcd for C219H318O273382.3578; Found
3382.3517。
Embodiment 2
The synthesis of truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP)
By single bromine benzophenanthrene TP (OC6H13)5(OCH2)8Br (131 mg, 0.14 mmol), and potassium carbonate (96.6 mg, 0.70
Mmol), 15 mL N, N '-dimethyl formamide are added in 25 mL round-bottomed flasks, stir at room temperature, complete to single bromine benzophenanthrene
Fully dissolved under inert gas shielding, is added trihydroxy truxene compound (30 mg, 0.035 mmol), 80 DEG C of heating stirring,
It reacts and removes protection after 40 h, reaction system is open in air that the reaction was continued 36h.TLC contact plate tracks to fully reacting, will
Reaction solution is cooled to room temperature, pours into ice water, that is, has red solid precipitation, and suction filtration obtains crude product, is dried in vacuo, and then uses column layer
Analysis isolates and purifies, and methylene chloride makees eluant, eluent, and the mixed solvent recrystallization of ethyl acetate and ethyl alcohol volume ratio 1: 5 obtains red
99.7 mg of color solid, yield 61%.
Infrared FT-IR:(KBr) νmax2926, 2855, 1695, 1617, 1575, 1515, 1466, 1261,
1171, 1040, 834 cm-1;Nucleus magnetic hydrogen spectrum1H NMR (400 MHz, CDCl3) δ 8.76 (s, 3H, ArH),
7.77-7.76 (d, J = 4.0 Hz, 6H, ArH), 7.21 (s, 3H, ArH), 4.35-4.32 (t, J = 6.0
Hz, 6H, 3×OCH2), 4.25-4.15 (m, 42H, 14×OCH2), 2.03-1.934 (m, 48H, 16×CH2),
1.66-1.33 (m, 156H, 52×CH2), 0.99-0.96 (t, J = 6.0 Hz, 45H, 15×CH3 ), 0.93-
0.89 (t, J = 8.0, 9H, 3×CH3);Nuclear-magnetism carbon spectrum13C NMR (100 MHz, CDCl3) δ 191.19,
154.30, 151.12, 148.79, 145.08, 136.68, 129.97, 127.61, 123.45, 111.68,
106.98, 106.31, 69.48, 69.13, 69.03, 31.94, 31.72, 29.70, 29.64, 29.56,
29.44, 29.42, 29.28, 29.20, 29.17, 28.85, 26.21, 26.05, 25.87, 25.71, 22.72,
22.68, 14.14, 14.08;High resolution mass spectrum HRMS (MALDI) m/z:[M]+ Calcd for
C225H330O273466.4517; Found 3466.4481。
Embodiment 3
The synthesis of truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP)
By single bromine benzophenanthrene TP (OC6H13)5(OCH2)10Br (118 mg, 0.123 mmol), and potassium carbonate (87 mg, 0.63
Mmol), 15 mL N, N '-dimethyl formamide are added in 25 mL round-bottomed flasks, stir at room temperature, complete to single bromine benzophenanthrene
Fully dissolved under inert gas shielding, is added trihydroxy truxene compound (30 mg, 0.035 mmol), 80 DEG C of heating stirring,
It reacts and removes protection after 48 h, reaction system is open in air that the reaction was continued 32h.TLC contact plate tracks to fully reacting, will
Reaction solution is cooled to room temperature, pours into ice water, that is, has red solid precipitation, and suction filtration obtains crude product, is dried in vacuo, and then uses column layer
Analysis isolates and purifies, and methylene chloride makees eluant, eluent, and the mixed solvent recrystallization of ethyl acetate and ethyl alcohol volume ratio 1: 5 obtains red
97.6 mg of color solid, yield 59%.
Infrared FT-IR:(KBr) νmax2927, 2855, 1693, 1617, 1577, 1515, 1467, 1261,
1169, 1043, 831 cm1;Nucleus magnetic hydrogen spectrum1H NMR (400 MHz, CDCl3) δ 8.76 (s, 3H, ArH),
7.74-7.73 (m, 6H, ArH), 7.21 (s, 3H, ArH), 4.30-4.27 (t, J = 6.0 Hz, 6H, 3×
OCH2), 4.21-4.07 (m, 42H, 14×OCH2), 1.96-1.91 (m, 48H, 16×CH2), 1.58-1.27
(m, 168H, 56×CH2), 0.95-0.91 (t, J = 8.0 Hz ,45H, 15×CH3 ), 0.88-0.85 ( t, J
= 6.0, 9H, 3×CH3);Nuclear-magnetism carbon spectrum13C NMR (100 MHz, CDCl3) δ 191.16, 154.21, 151.15,
148.77, 145.12, 136.59, 129.96, 127.62, 123.45, 111.58, 106.91, 106.16,
69.47, 69.06, 69.00, 31.98, 31.74, 29.75, 29.69, 29.62, 29.53, 29.49, 29.46,
29.43, 29.33, 29.23, 29.03, 26.26, 26.21, 25.88, 22.75, 22.71, 14.184, 14.12;
High resolution mass spectrum HRMS (MALDI) m/z:[M+H]+ Calcd for C231H342O273550.5456; Found m/z
3550.5433。
This kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds (TRO-n-TP) thermal stability with higher, heat are lost
Temperature when weighing 5% is 370 DEG C, and columnar phase liquid crystal texture is presented, and is the room temperature disk with wider mesomorphic phase temperature range
Shape liquid-crystal compounds is suitable as the liquid crystal material of organic electro-optic device.
After the obtained truxene ketone of embodiment 1-benzophenanthrene disc liquid-crystal compounds (TRO-6-TP) thermal annealing, the
Isotropic liquid is changed by columnar liquid crystalline phase when secondary temperature elevation is to 174 DEG C, by isotropic liquid when being cooled to 163 DEG C
Body is changed into columnar liquid crystalline phase.
After the obtained truxene ketone of embodiment 2-benzophenanthrene disc liquid-crystal compounds (TRO-8-TP) thermal annealing, the
Isotropic liquid is changed by columnar liquid crystalline phase when secondary temperature elevation is to 155 DEG C, by isotropic liquid when being cooled to 151 DEG C
Body is changed into columnar liquid crystalline phase.
After the obtained truxene ketone of embodiment 3-benzophenanthrene disc liquid-crystal compounds (TRO-10-TP) thermal annealing,
Isotropic liquid is changed by columnar liquid crystalline phase when being warming up to 174 DEG C for the second time, by isotropic when being cooled to 171 DEG C
Liquid is changed into columnar liquid crystalline phase.
Claims (7)
1. a kind of truxene ketone-benzophenanthrene disc liquid-crystal compounds, which is characterized in that the compound has the following general formula (I)
Structure, wherein R is straight chained alkyl-C m H2m+1, mIndicate that carbon atom number is 4 ~ 8 integer,nIndicate the methylene of flexible connection chain
Radix mesh is 6 ~ 10 integer,
Logical formula (I).
2. truxene ketone-benzophenanthrene disc liquid-crystal compounds according to claim 1, it is characterised in that: the straight chain alkane
Base includes normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl.
3. general formula described in claim 1 is truxene ketone-benzophenanthrene disc liquid-crystal compounds preparation method of (I), feature
It is: the method comprises the following steps:
Compound list bromine benzophenanthrene and potassium carbonate are added to N, in N '-dimethyl formamide, stirred at room temperature, simultaneously to single bromobenzene
Phenanthrene is completely dissolved；Then under inert gas protection, trihydroxy truxene compound is added, be heated to 80 DEG C be stirred to react 36 ~
48 hours, gas shield is removed later, then reaction system is open in air and is continued heating reflux reaction 24 ~ 36 hours；
After fully reacting, reaction solution is cooled to room temperature, is poured into ice water, that is, have red solid precipitation, suction filtration obtains crude product, and vacuum is dry
It is dry, purifying is then used column chromatography, methylene chloride makees eluant, eluent, last mixed organic solvents recrystallization, and vacuum drying obtains
Product.
4. the preparation method of truxene ketone-benzophenanthrene disc liquid-crystal compounds according to claim 3, it is characterised in that:
The molar ratio of the trihydroxy truxene, single bromine benzophenanthrene and potassium carbonate is 1: 3 ~ 4: 6 ~ 10.
5. the preparation method of truxene ketone-benzophenanthrene disc liquid-crystal compounds according to claim 3, it is characterised in that:
The organic solvent of the recrystallization is the mixed solvent of ethyl acetate and ethyl alcohol volume ratio 1: 5.
6. the preparation method of truxene ketone-benzophenanthrene disc liquid-crystal compounds according to claim 3, it is characterised in that:
Shown in the structure such as general formula (II) of the list bromine benzophenanthrene:
General formula (II).
7. the preparation method of truxene ketone-benzophenanthrene disc liquid-crystal compounds according to claim 3, it is characterised in that:
The trihydroxy truxene structure is shown below:
。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5635105A (en) * | 1994-05-13 | 1997-06-03 | Fuji Photo Film Co., Ltd. | Liquid crystal display and optical compensatory sheet and process for preparation of the same |
| CN101787288A (en) * | 2010-02-03 | 2010-07-28 | 四川师范大学 | Benzophenanthrene discotic liquid crystal polymer and preparation method thereof |
| WO2012114745A1 (en) * | 2011-02-23 | 2012-08-30 | 保土谷化学工業株式会社 | Compound containing substituted triphenyle ring structure, and organic electroluminescent element |
| CN102701921A (en) * | 2012-06-14 | 2012-10-03 | 四川师范大学 | Method for synthesizing disklike liquid crystal intermediate 2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylene and linear alkyl benzene |
| CN103403613A (en) * | 2012-02-01 | 2013-11-20 | Dic株式会社 | Liquid crystal display device |
-
2018
- 2018-12-01 CN CN201811460523.9A patent/CN109575937A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5635105A (en) * | 1994-05-13 | 1997-06-03 | Fuji Photo Film Co., Ltd. | Liquid crystal display and optical compensatory sheet and process for preparation of the same |
| CN101787288A (en) * | 2010-02-03 | 2010-07-28 | 四川师范大学 | Benzophenanthrene discotic liquid crystal polymer and preparation method thereof |
| WO2012114745A1 (en) * | 2011-02-23 | 2012-08-30 | 保土谷化学工業株式会社 | Compound containing substituted triphenyle ring structure, and organic electroluminescent element |
| CN103403613A (en) * | 2012-02-01 | 2013-11-20 | Dic株式会社 | Liquid crystal display device |
| CN102701921A (en) * | 2012-06-14 | 2012-10-03 | 四川师范大学 | Method for synthesizing disklike liquid crystal intermediate 2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylene and linear alkyl benzene |
Non-Patent Citations (4)
| Title |
|---|
| KE SHI，等: "pi-conjugated aromatics based on truxene：synthesis，self-assembly，and applications", 《THE CHEMICAL RECORD》 * |
| WEN ZHANG，等: "Star-shaped oligomers with truxenone centre and triphenylene branches mesomorphism, optical and electronic properties", 《LIQUID CRYSTALS》 * |
| 余文浩，等: "氢键稳定的苯并菲盘装液晶的合成及介晶性", 《化学学报》 * |
| 胡平，等: "吐昔烯酮-苯并菲盘状液晶齐聚物的合成及介晶性", 《中国化学会学术年会》 * |
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