TW201249960A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDF

Info

Publication number: TW201249960A
Authority: TW; Taiwan
Prior art keywords: group; substituted; compound; unsubstituted; aryl
Prior art date: 2011-04-12

Application number

TW101112951A

Other languages

English (en)

Chinese (zh)

Inventor

Hee-Choon Ahn

Seok-Keun Yoon

Hee-Sook Kim

Soo-Jin Yang

Kyung-Joo Lee

Nam-Kyun Kim

Young-Jun Cho

Hyuck-Joo Kwon

Bong-Ok Kim

Original Assignee

Rohm & Haas Elect Mat

Priority date (The priority date 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 date listed.)

2011-04-12

Filing date

2012-04-12

Publication date

2012-12-16

2012-04-12 Application filed by Rohm & Haas Elect Mat filed Critical Rohm & Haas Elect Mat

2012-12-16 Publication of TW201249960A publication Critical patent/TW201249960A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 157
239000012776 electronic material Substances 0.000 title description 5
125000003118 aryl group Chemical group 0.000 claims description 52
-1 extension Chemical group 0.000 claims description 29
230000005684 electric field Effects 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 18
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 9
125000002950 monocyclic group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
229910052796 boron Inorganic materials 0.000 claims description 7
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
229910052698 phosphorus Inorganic materials 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 5
239000007789 gas Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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125000001624 naphthyl group Chemical group 0.000 claims description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
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PGBVLOMZZHYJFP-UHFFFAOYSA-N 3-methyldithietane Chemical group CC1CSS1 PGBVLOMZZHYJFP-UHFFFAOYSA-N 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
150000001336 alkenes Chemical class 0.000 claims 1
150000004982 aromatic amines Chemical class 0.000 claims 1
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
210000000416 exudates and transudate Anatomy 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000005717 substituted cycloalkylene group Chemical group 0.000 claims 1
125000006836 terphenylene group Chemical group 0.000 claims 1
230000008901 benefit Effects 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
239000011541 reaction mixture Substances 0.000 description 76
238000002360 preparation method Methods 0.000 description 53
239000000203 mixture Substances 0.000 description 52
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000010410 layer Substances 0.000 description 37
239000012044 organic layer Substances 0.000 description 36
239000000463 material Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
235000019439 ethyl acetate Nutrition 0.000 description 32
239000007787 solid Substances 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000012153 distilled water Substances 0.000 description 10
239000002019 doping agent Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000008213 purified water Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000005259 measurement Methods 0.000 description 6
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
229910052805 deuterium Inorganic materials 0.000 description 5
230000005484 gravity Effects 0.000 description 5
238000000227 grinding Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
238000001665 trituration Methods 0.000 description 5
PSRYSSKJJRCOJV-UHFFFAOYSA-N 4H-1,3,2,4-benzodioxadiazine Chemical compound N1ONOC2=CC=CC=C12 PSRYSSKJJRCOJV-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
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 4
238000000926 separation method Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000758 substrate Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
238000007740 vapor deposition Methods 0.000 description 4
TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
238000005401 electroluminescence Methods 0.000 description 3
239000000499 gel Substances 0.000 description 3
230000005525 hole transport Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229910001507 metal halide Inorganic materials 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
229910044991 metal oxide Inorganic materials 0.000 description 3
150000004706 metal oxides Chemical class 0.000 description 3
125000003367 polycyclic group Chemical group 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
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239000007983 Tris buffer Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
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238000004299 exfoliation Methods 0.000 description 2
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239000005457 ice water Substances 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
229910052761 rare earth metal Inorganic materials 0.000 description 2
150000002910 rare earth metals Chemical class 0.000 description 2
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229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000002344 surface layer Substances 0.000 description 2
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
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JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
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UJASZVHDIGKVOK-UHFFFAOYSA-N 8-hydroxy-1h-quinoline-2-thione Chemical compound C1=CC(=S)NC2=C1C=CC=C2O UJASZVHDIGKVOK-UHFFFAOYSA-N 0.000 description 1
VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
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229910052684 Cerium Inorganic materials 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
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KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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230000000737 periodic effect Effects 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
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230000000171 quenching effect Effects 0.000 description 1
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150000003254 radicals Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
238000010025 steaming Methods 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
235000019529 tetraterpenoid Nutrition 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
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150000003648 triterpenes Chemical class 0.000 description 1
238000004506 ultrasonic cleaning Methods 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000002061 vacuum sublimation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

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TW101112951A 2011-04-12 2012-04-12 Novel compounds for organic electronic material and organic electroluminescent device using the same TW201249960A (en)

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2011
- 2011-04-12 KR KR1020110033910A patent/KR20120116269A/ko not_active Application Discontinuation
2012
- 2012-04-12 CN CN201280028741.XA patent/CN103619833A/zh active Pending
- 2012-04-12 TW TW101112951A patent/TW201249960A/zh unknown
- 2012-04-12 EP EP12771699.1A patent/EP2697216A4/de not_active Withdrawn
- 2012-04-12 JP JP2014505079A patent/JP2014513083A/ja active Pending
- 2012-04-12 WO PCT/KR2012/002762 patent/WO2012141499A1/en active Application Filing

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JP2014513083A (ja)	2014-05-29
CN103619833A (zh)	2014-03-05
EP2697216A4 (de)	2014-10-15
WO2012141499A1 (en)	2012-10-18
EP2697216A1 (de)	2014-02-19
KR20120116269A (ko)	2012-10-22

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TW201249960A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

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