CN106635052A - 具有负介电各向异性的液晶化合物及其应用 - Google Patents
具有负介电各向异性的液晶化合物及其应用 Download PDFInfo
- Publication number
- CN106635052A CN106635052A CN201510712026.3A CN201510712026A CN106635052A CN 106635052 A CN106635052 A CN 106635052A CN 201510712026 A CN201510712026 A CN 201510712026A CN 106635052 A CN106635052 A CN 106635052A
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- China
- Prior art keywords
- liquid crystal
- compound
- dielectric anisotropy
- negative dielectric
- crystal composition
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 1
- VTNFFMYGXVMSND-UHFFFAOYSA-N CC(CC1)COC1c(c(C)cc(C1=CCC(C)C(F)=C1F)c1F)c1F Chemical compound CC(CC1)COC1c(c(C)cc(C1=CCC(C)C(F)=C1F)c1F)c1F VTNFFMYGXVMSND-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 I-A-9 Chemical class 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
- 230000004075 alteration Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510712026.3A CN106635052A (zh) | 2015-10-28 | 2015-10-28 | 具有负介电各向异性的液晶化合物及其应用 |
| TW105133550A TWI608085B (zh) | 2015-10-28 | 2016-10-18 | Liquid-crystalline compound with negative dielectric anisotropy and its application |
| PCT/CN2016/103328 WO2017071575A1 (fr) | 2015-10-28 | 2016-10-26 | Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510712026.3A CN106635052A (zh) | 2015-10-28 | 2015-10-28 | 具有负介电各向异性的液晶化合物及其应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106635052A true CN106635052A (zh) | 2017-05-10 |
Family
ID=58629875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510712026.3A Pending CN106635052A (zh) | 2015-10-28 | 2015-10-28 | 具有负介电各向异性的液晶化合物及其应用 |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN106635052A (fr) |
| TW (1) | TWI608085B (fr) |
| WO (1) | WO2017071575A1 (fr) |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3839213A1 (de) * | 1988-11-19 | 1990-05-23 | Merck Patent Gmbh | Bis-(difluorphenylen)-derivate |
| EP0969071A1 (fr) * | 1998-06-02 | 2000-01-05 | Chisso Corporation | Composé alcényle à valeur delta epsilon négative, composition liquide cristalline et dispositif d'affichage à cristaux liquides |
| US6217953B1 (en) * | 1998-06-30 | 2001-04-17 | Merck Patent Gmbh | Liquid-crystalline medium |
| US6558758B1 (en) * | 1999-10-13 | 2003-05-06 | Chisso Corporation | Liquid crystal composition and liquid crystal display element |
| CN101519594A (zh) * | 2009-04-01 | 2009-09-02 | 晶宝液晶有限公司 | 液晶混合物和含所述液晶混合物的液晶显示器件 |
| WO2010095506A1 (fr) * | 2009-02-19 | 2010-08-26 | チッソ株式会社 | Composé cristallin liquide tétracyclique ayant du tétrahydropyrane et du 2,2',3,3'-tétrafluorobiphényle, composition cristalline liquide, et élément d'écran à cristaux liquides |
| CN103666485A (zh) * | 2013-12-04 | 2014-03-26 | 石家庄诚志永华显示材料有限公司 | 一种负介电各向异性液晶组合物 |
| WO2015079797A1 (fr) * | 2013-11-29 | 2015-06-04 | Jnc株式会社 | Composition à cristaux liquides et élément d'affichage à cristaux liquides |
| CN106278812A (zh) * | 2015-06-24 | 2017-01-04 | 江苏和成显示科技股份有限公司 | 一种具有负介电各向异性的液晶化合物及其组合物和其应用 |
| CN106324883A (zh) * | 2015-07-03 | 2017-01-11 | 北京大学 | 紫外光-加热分步聚合制备胆甾相液晶功能薄膜的方法 |
| CN106336875A (zh) * | 2015-07-07 | 2017-01-18 | 北京大学 | 一种反式聚合物分散液晶薄膜的制备方法 |
| CN106338854A (zh) * | 2015-07-07 | 2017-01-18 | 北京大学 | 加热-紫外光分步聚合制备胆甾相液晶功能薄膜的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104871336B (zh) * | 2012-12-18 | 2017-08-08 | 默克专利有限公司 | 具有稠合环系的发光体 |
-
2015
- 2015-10-28 CN CN201510712026.3A patent/CN106635052A/zh active Pending
-
2016
- 2016-10-18 TW TW105133550A patent/TWI608085B/zh active
- 2016-10-26 WO PCT/CN2016/103328 patent/WO2017071575A1/fr active Application Filing
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3839213A1 (de) * | 1988-11-19 | 1990-05-23 | Merck Patent Gmbh | Bis-(difluorphenylen)-derivate |
| EP0969071A1 (fr) * | 1998-06-02 | 2000-01-05 | Chisso Corporation | Composé alcényle à valeur delta epsilon négative, composition liquide cristalline et dispositif d'affichage à cristaux liquides |
| US6217953B1 (en) * | 1998-06-30 | 2001-04-17 | Merck Patent Gmbh | Liquid-crystalline medium |
| US6558758B1 (en) * | 1999-10-13 | 2003-05-06 | Chisso Corporation | Liquid crystal composition and liquid crystal display element |
| WO2010095506A1 (fr) * | 2009-02-19 | 2010-08-26 | チッソ株式会社 | Composé cristallin liquide tétracyclique ayant du tétrahydropyrane et du 2,2',3,3'-tétrafluorobiphényle, composition cristalline liquide, et élément d'écran à cristaux liquides |
| CN101519594A (zh) * | 2009-04-01 | 2009-09-02 | 晶宝液晶有限公司 | 液晶混合物和含所述液晶混合物的液晶显示器件 |
| WO2015079797A1 (fr) * | 2013-11-29 | 2015-06-04 | Jnc株式会社 | Composition à cristaux liquides et élément d'affichage à cristaux liquides |
| CN103666485A (zh) * | 2013-12-04 | 2014-03-26 | 石家庄诚志永华显示材料有限公司 | 一种负介电各向异性液晶组合物 |
| CN106278812A (zh) * | 2015-06-24 | 2017-01-04 | 江苏和成显示科技股份有限公司 | 一种具有负介电各向异性的液晶化合物及其组合物和其应用 |
| CN106324883A (zh) * | 2015-07-03 | 2017-01-11 | 北京大学 | 紫外光-加热分步聚合制备胆甾相液晶功能薄膜的方法 |
| CN106336875A (zh) * | 2015-07-07 | 2017-01-18 | 北京大学 | 一种反式聚合物分散液晶薄膜的制备方法 |
| CN106338854A (zh) * | 2015-07-07 | 2017-01-18 | 北京大学 | 加热-紫外光分步聚合制备胆甾相液晶功能薄膜的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI608085B (zh) | 2017-12-11 |
| WO2017071575A1 (fr) | 2017-05-04 |
| TW201716553A (zh) | 2017-05-16 |
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| PB01 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant after: Jiangsu He Cheng Display Technology Co., Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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| CB02 | Change of applicant information | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170510 |
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| RJ01 | Rejection of invention patent application after publication |