CN102249866B - Liquid crystal composition and negative liquid crystal compound with novel structure - Google Patents
Liquid crystal composition and negative liquid crystal compound with novel structure Download PDFInfo
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- CN102249866B CN102249866B CN201110126922.3A CN201110126922A CN102249866B CN 102249866 B CN102249866 B CN 102249866B CN 201110126922 A CN201110126922 A CN 201110126922A CN 102249866 B CN102249866 B CN 102249866B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000000178 monomer Substances 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 3
- 238000002844 melting Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- JLZVIWSFUPLSOR-UHFFFAOYSA-N 2,3-difluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1F JLZVIWSFUPLSOR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a negative liquid crystal monomer of a compound with a general formula I. The negative liquid crystal monomer has an extremely low melting point, a high clear point and low negative dielectric anisotropy. The invention also provides one or more liquid crystal mixtures of negative liquid crystal monomers and an electro-optic display element containing a liquid crystal composition.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd and liquid-crystal composition, relate in particular to a kind of liquid crystalline cpd and liquid crystal compound with lower fusing point, higher clearing point, fabulous low temperature mutual solubility.
Background technology
Liquid crystal material is a kind of mesomorphic phase material between solid phase and liquid phase, and its phase can roughly be divided into nematic phase, smectic phase and cholesteric phase.In display element, nematic being most widely used.(Δ n) and the characteristic of dielectric anisotropy (Δ ε) because of its intrinsic optical anisotropy for liquid crystalline cpd, be widely used at present the making of the device liquid crystal display device such as robot calculator, meter device, instrument panel for motor vehicle, electronic memo, mobile telephone, computer, televisor, its range of application is also in expansion year by year.Classify by liquid-crystal display mode, liquid crystal compound can be divided into the types such as dynamic scattering mode (DS type), guest-host type (GH type), twisted nematic (TN type), super-twist nematic (STN type), film transistor type (TFT type) and strong dielectricity (FLC).
Adopt thin film transistor (TFT) display format of liquid crystal molecule (VA) arranged vertically to have advantages of that wide visual angle, fast response time, contrast gradient are larger, in large scale liquid crystal TV, be used widely in recent years.Traditional distortion-nematic-mode (TN) uses dielectric anisotropy for (Δ ε=ε just
//-ε
⊥, Δ ε > 0) liquid crystal material, in molecular long axis direction, there is polar group, make long axis direction specific inductivity (ε
//) be greater than perpendicular electric constant (ε
⊥); And VA pattern requires the liquid crystal material adopting to have negative dielectric anisotropic (Δ ε < 0).Object of the present invention is exactly will provide to be applicable to the liquid crystal material that VA pattern requires.
Summary of the invention
One aspect of the present invention is to provide the compound of general formula I,
Wherein:
A
1, A
2and A
3represent independently of one another the Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or the Isosorbide-5-Nitrae-Ya cyclic group dialkylene that do not replace or replaced by one to four F atom, and one of them or two CH
2group also can be independently of one another by heteroatoms-O-or-S-with heteroatoms each other not directly connected mode replace; Isosorbide-5-Nitrae-phenylene, can be replaced by one or two fluorine or chlorine atom and one of them or two CH
2group can be replaced by N;
R
1and R
2represent independently of one another not replace or by least mono-substituted alkyl with 1 to 12 carbon atom of halogen and wherein one or more non-conterminous CH
2group also can be separately independently of each other by-O-,-S-or-CO-replaces; In every kind of situation, adjacent CH
2group also can by-CH=CH-,-CF=CF-,-COO-,-C ≡ C-or 1,2-cyclopropylidene replace, or three adjacent CH
2group can be replaced by the sub-cyclobutyl of 1,3-, and wherein, the sub-cyclobutyl of 1,2-cyclopropylidene and 1,3-also can be replaced by two F atoms independently of one another;
B
1, B
2and B
3represent independently of one another singly-bound ,-CH
2cH
2-,-CH
2o-,-OCH
2-,-CH
2cF
2-,-CF
2cH
2-,-CH
2cHF-,-CHFCH
2-,-CF
2o-,-COO-,-OOC-,-CH=CH-,-CF=CF-or-C ≡ C-;
Q
1and Q
2expression-O-CF independently of one another
2-or-CF
2-O-;
L, m, x and y represent 0 or 1 separately independently of each other, and when m=0, l+x+y≤2; When m=1, l+x+y >=0.
In preferred embodiments, described Q
1be-CF
2o-, described Q
2be-OCF
2-; Or, described Q
1be-OCF
2-, described Q
2be-CF
2o-.
In preferred embodiments, described R
1and R
2represent to have independently of one another the unsubstituted straight chained alkyl of 1-5 carbon atom.
Preferably, the compound of general formula I is selected from the compound to formula I19 as shown in the formula I1:
Preferably, R
1and R
2represent independently of one another the unsubstituted straight chained alkyl that contains 1 to 5 carbon atom.
Particularly preferred compound is I1, I2, I3, I4, I5, I6 and I12, especially I1, I2, I5 and I6.
Thus, the invention provides a kind of negative liquid crystal monomer, this liquid crystal monomer has utmost point low melting point, higher clearing point, low negative dielectric anisotropic.
Another aspect of the present invention is the liquid crystal compound that contains one or several above-mentioned negative liquid crystal monomers, and the electrooptical display cells that comprises described liquid-crystal composition.
The compound of structural formula I has wide range of application.Depend on substituent selection, these compounds can be used as the base mateiral of main composition liquid crystal media; But, also likely add the compound of general formula I in the liquid crystal base mateiral being selected from other types compound, so that for example improve dielectric optical anisotropy of this type, optimize its threshold voltage.
Brief description of the drawings
Fig. 1 is the mass spectrum of the compound of formula I1.
Embodiment
Following embodiment is intended to explain the present invention, but does not limit in any form the present invention.All per-cent represents weight percent.Following temperature is centigradetemperature.H represents hour, and min represents minute, and Mp represents fusing point, and Cp represents clearing point, V
threpresent threshold voltage, Δ n represents specific refractory power, and ε ⊥ represents specific inductivity, and Visc represents kinetic viscosity.
Embodiment 1
synthesis path 1
According to synthesis path 1 (with reference to Angew.Chem.Int.Ed.2001,40, NO.8,1480-1484), in toluene and (90-120) in mixed solvent that sherwood oil volume ratio is 1: 1 by 1 of the trifluoromethayl sulfonic acid of 1.3 times of molar weights and 1.3 times of molar weights, 3-dimercaptopropane joins commercially available obtaining in propyl group hexahydrobenzoic acid, 95 ± 5 DEG C of reacting by heating.After 6h, under nitrogen protection, make system temperature be down to 20 DEG C, 80 DEG C of water-bath temperature controls, toluene distillation and sherwood oil under vacuum-0.8MPa, until product while becoming thick liquid or solid, stops distillation, logical nitrogen is to normal pressure.In reaction vessel, add ether not have product 0.5cm to be as the criterion again.More than again product being proceeded to the following 8h of preservation in cyrogenic equipment temperature control-20 DEG C.Suction strainer after freezing end, obtains white or faint yellow solid powder, i.e. intermediate product a1.
Under nitrogen, in-85 DEG C, by 2 of 1.3 times of molar weights, 3-difluorophenol mixes with the triethylamine of 1.3 times of molar weights, is added drop-wise to the CH of intermediate product a1
2cl
2in solution, after reaction 1.5h, at-80 DEG C, successively the bromine of compound triethylamine of 5 times of molar weights trihydrofluoride and 5 times of molar weights is added drop-wise in reaction system, after reaction 1h, reaction solution is poured in mixture of ice and water, with 20% aqueous sodium hydroxide solution adjust pH to 5-8, dichloromethane extraction water, combined dichloromethane layer, be washed to neutrality, again with extremely clarification of anhydrous sodium sulfate drying, concentrate to obtain weak yellow liquid (hereinafter to be referred as conventional processing), column chromatography purification (60-100 order silica gel, eluent is sherwood oil), concentrate except after desolventizing and obtain intermediate a2.
Under nitrogen, in THF, must n-Butyl Lithium intermediate a2 be carried out to lithiumation by the commercially available of 1.1 times of molar weights with-78 DEG C, after reaction 2h, at-75 DEG C, boric acid three isobutyl esters are joined in this organometallic compound, after reaction 1h, be naturally warming up to-30 DEG C, use dilute hydrochloric acid acidifying, water layer is extracted with ethyl acetate, merge oil phase after washing to neutral, then use anhydrous sodium sulfate drying, after concentrated doing, process to obtain intermediate a3 with sherwood oil.
In the mixed solvent that is 3: 2: 1 in methylene dichloride, dioxane and deionized water volume ratio by 30%H
2o
2join in intermediate a3, in 38-40 DEG C of reaction 8-12 hour, obtain intermediate a4 through conventional processing.Taking intermediate a1 and a4 as main raw material, adopt the synthetic method of intermediate a2 to make final product I1.Mp＝60.35-62.55℃，Cp＝155.74-157.58℃。
The mass spectrum of product I1 as shown in Figure 1.
Embodiment 2
synthesis path 2
According to method described in embodiment 1, finally make product I5 taking commercially available propyl group dicyclohexyl formic acid and valeric acid as initial feed through several synthesis steps, concrete implementation step is explained as composite diagram 2.
Embodiment 3
synthesis path 3
According to synthesis path 3, under nitrogen, at-78 DEG C, the n-Butyl Lithium of 1.1 times of molar weights is joined to commercially available obtaining in 1,2-Difluorobenzene and react 2h, then pass into excessive CO in the organometallics forming
2until reaction system is no longer because passing into CO
2and heat up, stop passing into CO
2.Reaction solution is regulated to pH value 1-2 with 10% aqueous hydrochloric acid, and water is with after toluene extraction, and oil phase anhydrous sodium sulfate drying, concentrates to obtain faint yellow solid, obtains straight product 2,3-difluoro-benzoic acid, i.e. intermediate b1 through sherwood oil recrystallization.Utilize method described in embodiment 1,2,3-difluoro-benzoic acid can make intermediate b2 by two-step reaction.Adopt the synthetic method of intermediate b1 intermediate b2 can be prepared into intermediate b3.And b3 intermediate can be prepared into intermediate b4 by method described in embodiment 1.Taking intermediate b4 and 4-propylphenol as main raw material, adopt method sintetics I5 described in embodiment 1.
Embodiment 4
synthesis path 4
According to method described in embodiment 1, finally make product I6 taking commercially available propylbenzoic acid and propyl group dicyclohexyl formic acid as initial feed through several synthesis steps, concrete implementation step is explained as synthesis path 4.
Embodiment 5-7
Same synthetic by conventionally known method:
Embodiment 8
Preparation has the liquid-crystal composition of composition shown in table 1:
Table 1
Wherein, clearing point is to use melting point apparatus to test; Threshold voltage is to use liquid crystal device parametric synthesis tester LCT-5016C to test; Specific refractory power and specific refractory power anisotropy use Abbe refractometer under sodium lamp (589nm) light source, 20 DEG C test; Measurement box is TN90 type, the thick 7 μ m of box; Kinetic viscosity Visc uses cone-and-plate viscometer to test;
According to above method, record parameters as follows:
Δ n=0.1223 (probe temperature is 20 DEG C);
ε⊥＝10.13；
Cp＝119.2℃；
Vth=2.8v (probe temperature is 20 DEG C);
η=57.8 (probe temperature is 20 DEG C).
Claims (4)
1. the compound of formula I 1,
Wherein:
R
1and R
2independently of one another represent do not replace or by least mono-substituted alkyl with 1 to 12 carbon atom of halogen.
2. compound according to claim 1, is characterized in that, described R
1and R
2represent to have independently of one another the unsubstituted straight chained alkyl of 1-5 carbon atom.
3. a liquid-crystal composition, is characterized in that, described liquid-crystal composition comprises at least one compound as described in one of claim 1 to 2.
4. an electrooptical display cells, is characterized in that, described electrooptical display cells comprises liquid-crystal composition as claimed in claim 3.
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| TW201414817A (en) * | 2012-10-15 | 2014-04-16 | Daxin Materials Corp | Negative dielectric anisotropy liquid crystal compound and liquid crystal composition containing the same |
| CN103254907B (en) * | 2013-04-23 | 2016-01-20 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal composition |
| CN104531166B (en) * | 2014-12-12 | 2016-09-07 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds containing cyclopropyl and liquid crystal compound |
| CN106675576B (en) * | 2015-11-06 | 2018-09-04 | 江苏和成显示科技有限公司 | A kind of dielectric negative liquid crystal compound and the preparation method and application thereof |
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Address after: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Applicant after: Jiangsu Hecheng Display Technology Co.,Ltd. Address before: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Applicant before: Jiangsu Hecheng Chemical Materials Co., Ltd. Address after: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Applicant after: Jiangsu Hecheng Display Technology Co.,Ltd. Address before: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Applicant before: Jiangsu Hecheng Chemical Materials Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: HECHENG CHEMICAL MATERIAL CO., LTD., JIANGSU TO: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD. |
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Address after: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Patentee after: Jiangsu He Cheng Display Technology Co., Ltd. Address before: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. Address after: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Patentee after: Jiangsu He Cheng Display Technology Co., Ltd. Address before: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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Effective date of registration: 20200430 Address after: No. 9, camphor Road, economic development zone, Daguan District, Anqing, Anhui Patentee after: ANQING FEIKAI NEW MATERIAL Co.,Ltd. Address before: 212212 east side of Yangzhong, Jiangsu, Yangtze River Bridge Patentee before: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. |