JP5662461B2 - 重水素化芳香族化合物を調製する方法 - Google Patents
重水素化芳香族化合物を調製する方法 Download PDFInfo
- Publication number
- JP5662461B2 JP5662461B2 JP2012535184A JP2012535184A JP5662461B2 JP 5662461 B2 JP5662461 B2 JP 5662461B2 JP 2012535184 A JP2012535184 A JP 2012535184A JP 2012535184 A JP2012535184 A JP 2012535184A JP 5662461 B2 JP5662461 B2 JP 5662461B2
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- Prior art keywords
- acid
- deuterated
- deuterium
- aromatic
- liquid composition
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- 150000001491 aromatic compounds Chemical class 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000011903 deuterated solvents Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004431 deuterium atom Chemical group 0.000 claims description 13
- -1 aromatic hydrogen Chemical class 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 5
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 claims description 3
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
- 239000003341 Bronsted base Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25484309P | 2009-10-26 | 2009-10-26 | |
| US61/254,843 | 2009-10-26 | ||
| PCT/US2009/068924 WO2011053334A1 (fr) | 2009-10-26 | 2009-12-21 | Procédé pour la préparation de composés aromatiques deutérés |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013508360A JP2013508360A (ja) | 2013-03-07 |
| JP5662461B2 true JP5662461B2 (ja) | 2015-01-28 |
Family
ID=43922420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012535184A Active JP5662461B2 (ja) | 2009-10-26 | 2009-12-21 | 重水素化芳香族化合物を調製する方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2493835A4 (fr) |
| JP (1) | JP5662461B2 (fr) |
| KR (1) | KR101538534B1 (fr) |
| CN (1) | CN102574753B (fr) |
| TW (1) | TW201114735A (fr) |
| WO (1) | WO2011053334A1 (fr) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| EP2414481A4 (fr) | 2009-04-03 | 2013-02-20 | Du Pont | Matériaux électroactifs |
| CN102510889B (zh) | 2009-09-29 | 2015-11-25 | E.I.内穆尔杜邦公司 | 用于发光应用的氘代化合物 |
| TW201114771A (en) | 2009-10-29 | 2011-05-01 | Du Pont | Deuterated compounds for electronic applications |
| US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
| TW201229204A (en) | 2010-12-17 | 2012-07-16 | Du Pont | Anthracene derivative compounds for electronic applications |
| US20130248843A1 (en) | 2010-12-17 | 2013-09-26 | E I Du Pont De Nemours And Company | Anthracene derivative compounds for electronic applications |
| JP2014507401A (ja) | 2010-12-20 | 2014-03-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電子技術応用のためのトリアジン誘導体 |
| EP2655547A1 (fr) | 2010-12-20 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Compositions pour des applications électroniques |
| WO2012087961A2 (fr) | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Compositions électroactives pour applications électroniques |
| EP2655339A1 (fr) | 2010-12-21 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Dispositif électronique comprenant un composé pyrimidine |
| KR102154797B1 (ko) | 2013-02-25 | 2020-09-10 | 주식회사 엘지화학 | 다이아자크리센 유도체를 포함하는 전자 소자 |
| CN105981192B (zh) | 2013-12-13 | 2018-10-16 | E.I.内穆尔杜邦公司 | 形成电活性层的体系 |
| CN104198631B (zh) * | 2014-08-11 | 2017-01-18 | 贾明宏 | 一种提高蛋白质在氘代试剂中氢氘原子交换效率的方法 |
| US9944846B2 (en) | 2014-08-28 | 2018-04-17 | E I Du Pont De Nemours And Company | Compositions for electronic applications |
| CN107074763B (zh) | 2014-10-20 | 2021-01-05 | 株式会社Lg化学 | 蓝色发光化合物 |
| US10804473B2 (en) | 2015-05-21 | 2020-10-13 | Lg Chem, Ltd. | Electron transport materials for electronic applications |
| US11114621B2 (en) | 2016-07-20 | 2021-09-07 | Lg Chem, Ltd. | Electroactive materials |
| KR102627027B1 (ko) * | 2019-11-29 | 2024-01-18 | 주식회사 엘지화학 | 중수소화 안트라센계 화합물의 제조 방법 및 이로부터 제조된 중수소화 안트라센계 화합물을 포함하는 유기 발광 소자 |
| KR102594845B1 (ko) * | 2019-12-23 | 2023-10-27 | 주식회사 엘지화학 | 방향족 화합물의 제조방법 |
| KR20210126822A (ko) * | 2020-04-10 | 2021-10-21 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| US20230165139A1 (en) * | 2020-04-10 | 2023-05-25 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element using same, and electronic device thereof |
| KR20210128205A (ko) * | 2020-04-16 | 2021-10-26 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| CN113555519A (zh) | 2020-04-24 | 2021-10-26 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光装置 |
| KR102657636B1 (ko) | 2020-06-09 | 2024-04-15 | 주식회사 엘지화학 | 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자 |
| CN113896734A (zh) | 2020-07-06 | 2022-01-07 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物、多种主体材料和包含其的有机电致发光装置 |
| KR102657637B1 (ko) | 2020-07-08 | 2024-04-15 | 주식회사 엘지화학 | 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자 |
| KR20220065950A (ko) | 2020-11-13 | 2022-05-23 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20220065451A (ko) | 2020-11-13 | 2022-05-20 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20220065453A (ko) | 2020-11-13 | 2022-05-20 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20220065449A (ko) | 2020-11-13 | 2022-05-20 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR102629146B1 (ko) | 2021-01-08 | 2024-01-24 | 주식회사 엘지화학 | 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자 |
| KR102630972B1 (ko) | 2021-01-08 | 2024-01-29 | 주식회사 엘지화학 | 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자 |
| DE102022112831A1 (de) * | 2021-05-26 | 2022-12-01 | Rohm And Haas Electronic Materials Korea Ltd. | Verfahren zur herstellung von deuterierten organischen verbindungen |
| CN117480168A (zh) | 2021-07-07 | 2024-01-30 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
| KR20230018162A (ko) | 2021-07-29 | 2023-02-07 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20230018160A (ko) | 2021-07-29 | 2023-02-07 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20230018159A (ko) | 2021-07-29 | 2023-02-07 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20230107466A (ko) | 2022-01-07 | 2023-07-17 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| CN116888114A (zh) | 2022-01-07 | 2023-10-13 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
| WO2023132489A1 (fr) | 2022-01-07 | 2023-07-13 | 주식회사 엘지화학 | Composé et dispositif électroluminescent organique le comprenant |
| US20230255102A1 (en) | 2022-01-20 | 2023-08-10 | Rohm And Haas Electronic Materials Korea Ltd. | Plurality of host materials and organic electroluminescent device comprising the same |
| EP4231804A3 (fr) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Matériaux et dispositifs électroluminescents organiques |
| KR20240003039A (ko) | 2022-06-29 | 2024-01-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20240003040A (ko) | 2022-06-29 | 2024-01-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20240002594A (ko) | 2022-06-29 | 2024-01-05 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2024133048A1 (fr) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Procédé de préparation de composés aromatiques deutérés |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3389705A (en) * | 1966-04-29 | 1968-06-25 | Levavi David | Cigarette smoke filter device |
| US3989705A (en) * | 1974-04-01 | 1976-11-02 | Canadian Patents And Development Limited | Processes for the deuteration and/or tritiation of organic substrates by hydrogen substitution |
| JPS6153228A (ja) * | 1984-08-22 | 1986-03-17 | Nippon Sheet Glass Co Ltd | 芳香族化合物に高選択的に水素同位体を導入する方法 |
| JPH0653693B2 (ja) * | 1986-07-24 | 1994-07-20 | ユニチカ株式会社 | 重水素化フエノ−ル類の製造方法 |
| JPH06228014A (ja) * | 1993-01-28 | 1994-08-16 | Tosoh Corp | 重水素化芳香族化合物の製造法 |
| JP2789084B2 (ja) * | 1995-11-24 | 1998-08-20 | 勝 中原 | 重水素化化合物の製造方法 |
| JP2004010550A (ja) * | 2002-06-07 | 2004-01-15 | Japan Science & Technology Corp | 重水素化芳香族化合物の製造方法 |
| TW200404054A (en) * | 2002-07-26 | 2004-03-16 | Wako Pure Chem Ind Ltd | Method for deuteration of aromatic ring |
| TW200413273A (en) * | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| TW200413274A (en) * | 2002-12-27 | 2004-08-01 | Wako Pure Chem Ind Ltd | Deuteration or tritiation method |
| JP4839839B2 (ja) * | 2004-01-23 | 2011-12-21 | 和光純薬工業株式会社 | 混合触媒を用いた重水素化方法 |
| JP5464395B2 (ja) * | 2008-02-01 | 2014-04-09 | 大陽日酸株式会社 | 重水素化された芳香環又は複素環を有する化合物の製造方法 |
| TW201114771A (en) * | 2009-10-29 | 2011-05-01 | Du Pont | Deuterated compounds for electronic applications |
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| CN102574753B (zh) | 2015-07-08 |
| EP2493835A4 (fr) | 2015-07-15 |
| JP2013508360A (ja) | 2013-03-07 |
| WO2011053334A1 (fr) | 2011-05-05 |
| TW201114735A (en) | 2011-05-01 |
| EP2493835A1 (fr) | 2012-09-05 |
| KR20120101029A (ko) | 2012-09-12 |
| KR101538534B1 (ko) | 2015-07-21 |
| CN102574753A (zh) | 2012-07-11 |
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