TWI605869B - 利用離子液體的有機材料提煉方法及提煉裝置 - Google Patents
利用離子液體的有機材料提煉方法及提煉裝置 Download PDFInfo
- Publication number
- TWI605869B TWI605869B TW104104901A TW104104901A TWI605869B TW I605869 B TWI605869 B TW I605869B TW 104104901 A TW104104901 A TW 104104901A TW 104104901 A TW104104901 A TW 104104901A TW I605869 B TWI605869 B TW I605869B
- Authority
- TW
- Taiwan
- Prior art keywords
- organic material
- ionic liquid
- sublimation
- casing
- refining
- Prior art date
Links
- 239000011368 organic material Substances 0.000 title claims description 343
- 239000002608 ionic liquid Substances 0.000 title claims description 291
- 238000007670 refining Methods 0.000 title claims description 167
- 238000000034 method Methods 0.000 title claims description 96
- 238000000859 sublimation Methods 0.000 claims description 204
- 230000008022 sublimation Effects 0.000 claims description 204
- 230000007246 mechanism Effects 0.000 claims description 141
- 238000003860 storage Methods 0.000 claims description 60
- 238000011084 recovery Methods 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 42
- 238000001953 recrystallisation Methods 0.000 claims description 42
- 239000012535 impurity Substances 0.000 claims description 36
- 238000004064 recycling Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 18
- 238000004891 communication Methods 0.000 claims description 13
- 230000003134 recirculating effect Effects 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 description 115
- 239000000463 material Substances 0.000 description 54
- 230000008569 process Effects 0.000 description 40
- 238000010438 heat treatment Methods 0.000 description 32
- 239000002994 raw material Substances 0.000 description 28
- 239000000126 substance Substances 0.000 description 22
- 239000012159 carrier gas Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 238000010586 diagram Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 9
- 238000002061 vacuum sublimation Methods 0.000 description 9
- 230000008859 change Effects 0.000 description 8
- 230000002093 peripheral effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000011162 core material Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000992 sputter etching Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- FIMQDWPAUNOAIR-UHFFFAOYSA-N N-benzyl-N-[4-[4-[benzyl(naphthalen-1-yl)amino]phenyl]phenyl]naphthalen-1-amine Chemical compound C1(=CC=CC2=CC=CC=C12)N(C1=CC=C(C=C1)C1=CC=C(N(CC2=CC=CC=C2)C2=CC=CC3=CC=CC=C23)C=C1)CC1=CC=CC=C1 FIMQDWPAUNOAIR-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003146 anticoagulant agent Chemical class 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D7/00—Sublimation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/311—Purifying organic semiconductor materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D2009/0086—Processes or apparatus therefor
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Crystallography & Structural Chemistry (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Electroluminescent Light Sources (AREA)
- Gas Separation By Absorption (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20140017506 | 2014-02-14 | ||
| KR20140017496 | 2014-02-14 | ||
| KR20140021550 | 2014-02-24 | ||
| KR20140021551 | 2014-02-24 | ||
| KR20140031872 | 2014-03-18 | ||
| KR20140057339 | 2014-05-13 | ||
| KR1020150012661A KR101547096B1 (ko) | 2015-01-27 | 2015-01-27 | 이온성 액체를 이용한 유기소재 정제방법 및 정제장치 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201538223A TW201538223A (zh) | 2015-10-16 |
| TWI605869B true TWI605869B (zh) | 2017-11-21 |
Family
ID=53800362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104104901A TWI605869B (zh) | 2014-02-14 | 2015-02-13 | 利用離子液體的有機材料提煉方法及提煉裝置 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10069070B2 (https=) |
| JP (1) | JP6470298B2 (https=) |
| CN (1) | CN106030847B (https=) |
| TW (1) | TWI605869B (https=) |
| WO (1) | WO2015122686A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6517518B2 (ja) * | 2015-01-26 | 2019-05-22 | 国立大学法人東北大学 | 有機化合物析出方法及びその装置 |
| KR102482452B1 (ko) * | 2017-09-28 | 2022-12-29 | 삼성디스플레이 주식회사 | 유기 재료 정제 조성물 및 이를 이용한 유기 재료 정제 방법 |
| JP6851603B2 (ja) * | 2018-03-19 | 2021-03-31 | 国立大学法人東北大学 | 有機化合物析出方法 |
| CN108786326A (zh) * | 2018-07-02 | 2018-11-13 | 黑龙江兰德超声科技股份有限公司 | 工业废气处理用陶瓷过滤管装置 |
| CN113995547A (zh) * | 2021-11-04 | 2022-02-01 | 上海理工大学 | 一种新型双重均匀径向夹持的人工肛门括约肌装置 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63116702A (ja) * | 1986-11-05 | 1988-05-21 | Hitachi Ltd | 昇華物の回収方法及び装置 |
| JP4866527B2 (ja) * | 2000-03-23 | 2012-02-01 | 新日鐵化学株式会社 | 昇華精製方法 |
| JP2004018468A (ja) | 2002-06-18 | 2004-01-22 | Mitsubishi Materials Corp | ルテニウム化合物及びその製造方法並びに該化合物により得られたルテニウム含有薄膜 |
| KR100509149B1 (ko) * | 2003-06-04 | 2005-08-18 | 윈텍 코포레이숀 | 승화를 통한 정제방법 |
| JP2006075740A (ja) * | 2004-09-10 | 2006-03-23 | Mitsubishi Materials Corp | イオン性液体の精製方法 |
| US7563308B2 (en) * | 2004-09-23 | 2009-07-21 | Air Products And Chemicals, Inc. | Ionic liquid based mixtures for gas storage and delivery |
| KR101536378B1 (ko) * | 2011-04-26 | 2015-07-13 | 주식회사 엘지화학 | 정제 장치 |
| JP2013116879A (ja) | 2011-10-31 | 2013-06-13 | Idemitsu Kosan Co Ltd | 有機材料の精製装置及び有機材料の精製方法 |
| JP6006516B2 (ja) * | 2012-03-30 | 2016-10-12 | 出光興産株式会社 | 有機材料の精製装置 |
| CN202951451U (zh) * | 2012-12-12 | 2013-05-29 | 辽宁大学 | 一种离子液体提纯装置 |
| CN104884146A (zh) * | 2012-12-18 | 2015-09-02 | 韩国生产技术研究院 | 利用离子液体的有机材料提纯方法及提纯装置 |
-
2015
- 2015-02-11 WO PCT/KR2015/001378 patent/WO2015122686A1/ko not_active Ceased
- 2015-02-11 CN CN201580008439.1A patent/CN106030847B/zh not_active Expired - Fee Related
- 2015-02-11 JP JP2016552324A patent/JP6470298B2/ja not_active Expired - Fee Related
- 2015-02-11 US US15/118,288 patent/US10069070B2/en active Active
- 2015-02-13 TW TW104104901A patent/TWI605869B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017510436A (ja) | 2017-04-13 |
| CN106030847B (zh) | 2018-12-11 |
| US10069070B2 (en) | 2018-09-04 |
| US20160372673A1 (en) | 2016-12-22 |
| CN106030847A (zh) | 2016-10-12 |
| TW201538223A (zh) | 2015-10-16 |
| WO2015122686A1 (ko) | 2015-08-20 |
| JP6470298B2 (ja) | 2019-02-13 |
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