CN112714766B - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDFInfo
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- CN112714766B CN112714766B CN201980060088.7A CN201980060088A CN112714766B CN 112714766 B CN112714766 B CN 112714766B CN 201980060088 A CN201980060088 A CN 201980060088A CN 112714766 B CN112714766 B CN 112714766B
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 88
- 239000000463 material Substances 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 claims 1
- -1 2-methylbut-2-enyl Chemical group 0.000 description 165
- 239000010410 layer Substances 0.000 description 63
- 125000003118 aryl group Chemical group 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 29
- 125000005104 aryl silyl group Chemical group 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000001769 aryl amino group Chemical group 0.000 description 19
- 150000002431 hydrogen Chemical class 0.000 description 16
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- AYJJTPLDSZAGGA-UHFFFAOYSA-N 2-ethyl-7-methyl-5-(4-methylphenyl)-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine Chemical compound C1N(CC)CCC2C1C1=CC=C(C)C=C1C2C1=CC=C(C)C=C1 AYJJTPLDSZAGGA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- 238000007341 Heck reaction Methods 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum 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
- 238000002360 preparation method Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- 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 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YAVCXSHORWKJQQ-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YAVCXSHORWKJQQ-UHFFFAOYSA-N 0.000 description 1
- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 11h-indeno[1,2-h]quinoline Chemical group C1=CC=NC2=C3CC4=CC=CC=C4C3=CC=C21 ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XDNADZYPWVQFRI-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinoline Chemical compound C1=CC=NC2=C3C4=CC=CC=C4OC3=CC=C21 XDNADZYPWVQFRI-UHFFFAOYSA-N 0.000 description 1
- CWDFYKZZCSEOPO-UHFFFAOYSA-N [1]benzothiolo[2,3-h]quinoline Chemical compound C1=CC=NC2=C3C4=CC=CC=C4SC3=CC=C21 CWDFYKZZCSEOPO-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005870 benzindolyl group Chemical group 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
- 150000004950 naphthalene Chemical class 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- Chemical & Material Sciences (AREA)
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- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device including the same. By including the organic electroluminescent compounds having good thermal stability of the present disclosure, an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or longer lifetime characteristics than conventional organic electroluminescent devices can be provided.
Description
Technical Field
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device including the same.
Background
An Electroluminescent (EL) device is a self-luminous device, which has advantages in that it provides a wider viewing angle, a larger contrast ratio, and a faster response time. The organic electroluminescent device was first developed by the company Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light emitting layer [ appl. Phys. Lett. [ applied physics rapid paper ]51,913,1987].
An organic electroluminescent device (OLED) converts electrical energy into light by applying electric power to an organic light emitting material, and generally has a structure including an anode, a cathode, and an organic layer between the two electrodes. The organic layer of the OLED may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like, if necessary. The materials used in the organic layer may be classified into a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (containing a host material and a dopant material), an electron buffering material, a hole blocking material, an electron transporting material, an electron injecting material, and the like according to their functions. In the OLED, holes from an anode and electrons from a cathode are injected into a light emitting layer by applying a voltage, and excitons having high energy are generated by recombination of the holes and electrons. The organic light emitting compound moves to an excited state by energy and emits light by the energy when the organic light emitting compound returns from the excited state to a ground state.
The most important factor determining the luminous efficiency in an OLED is the luminescent material. The luminescent material is required to have the following characteristics: high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed light emitting material layer. The luminescent materials are classified into blue, green and red luminescent materials according to luminescent colors, and further include yellow or orange luminescent materials. Further, in terms of function, the light emitting material is divided into a host material and a dopant material. Preferably, as a solid solvent and energy emitter, the host material should have a high purity and a suitable molecular weight for deposition under vacuum. In addition, the host material is required to have a high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability, long life and formability of amorphous thin films.
Recently, an urgent task is to develop an OLED having high efficiency and long life. In particular, in view of EL characteristics required for medium-and large-sized OLED panels, development of highly excellent light emitting materials superior to conventional materials is eagerly demanded.
Meanwhile, U.S. patent No. 6,706,423 (published as 16/3/2004) discloses a compound containing indole as a light-emitting material, but development is still required to improve the performance of an OLED.
Disclosure of Invention
Technical problem
An object of the present disclosure is to provide an organic electroluminescent compound having good thermal stability and being effective for producing an organic electroluminescent device having low driving voltage, high luminous efficiency and/or long life characteristics.
Solution to the problem
Compounds with low glass transition temperatures (Tg) may reduce charge mobility in the thin film and deteriorate the performance of the OLED device. As a result of intensive studies, the present inventors developed a novel organic electroluminescent compound having a planar main core, which can help pi-pi stacking in a vacuum deposition layer to cause rapid charge mobility, and which can provide excellent morphological stability despite its low molecular weight, having a high Tg. Specifically, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1:
wherein the method comprises the steps of
A 1 To A 11 Each independently represents N or CR 1 ；
X 1 Representation N, NR 3 Or CR (CR) 4 ，X 2 Represents N or C; provided that X 1 And X 2 At least one of which contains N;
R 1 、R 3 、R 4 、Ar 1 and Ar is a group 2 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or two or more adjacent R' s 1 May be connected to each other to form one or more rings; wherein if there are multiple R' s 1 Each R 1 May be the same or different; and is also provided with
L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group.
The beneficial effects of the invention are that
The organic electroluminescent compounds according to the present disclosure have good thermal stability, and additionally or alternatively, an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long life characteristics may be provided.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure in any way.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
In this context, the term "(C1-C30) (alkylene) alkyl" means a straight or branched chain alkylene group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. The term "(C2-C30) alkenyl" means a straight or branched alkenyl group having 2 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. The term "(C2-C30) alkynyl" means a straight or branched alkynyl group having 2 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl group may include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methylpent-2-ynyl group and the like. The term "(C3-C30) (alkylene) cycloalkyl" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably from 3 to 20, and more preferably from 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "(3-to 7-membered) heterocycloalkyl" means cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, si and P, and preferably consisting of O,S and N. The above heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiopan), tetrahydropyran and the like. The term "(C6-C30) (arylene) refers to a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18. The aryl groups described above may be partially saturated and may contain spiro structures. The aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl (tetracenyl), perylenyl,A group, a naphto-naphthyl group, a fluoranthenyl group, a spirobifluorenyl group, and the like. More specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthraceyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthaceneyl, pyrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-tetraphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl, o-isopropylphenyl, m-isopropylphenyl p-isopropylphenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl p-isopropylphenyl group, p-tert-butylphenyl group, p- (2-phenylpropyl) phenyl group 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl.
The term "(3-to 30-membered) (arylene) heteroaryl" means an aryl group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si, and P. The heteroaryl group may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be heteroaryl formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may comprise a helical structure. The heteroaryl group may include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazayl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like; and fused ring type heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and the like. More specifically, the process is carried out, the heteroaryl group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2, 3-triazin-4-yl, 1,2, 4-triazin-3-yl, 1,3, 5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 3-phenanthridinyl, 2-thienyl, 3-thienyl, 2-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, silicon-germanium fluorenyl, silicon-3-germanium fluorenyl, silicon-germanium-silicon-3-germanium-fluorine-base, and the like. "halogen" includes F, cl, br, and I.
In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2. Meta-position means that two substituents are at positions 1 and 3 and is referred to as meta-position, for example, when two substituents in the benzene derivative occupy positions 1 and 3. Para represents two substituents at positions 1 and 4, and is referred to as para, for example, when two substituents in the benzene derivative occupy positions 1 and 4.
In this context, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., substituent). In the present disclosure, the substituents of the substituted (C1-C30) (alkylene), substituted (C6-C30) (arylene), substituted (3-to 30-membered) (arylene), substituted (C3-C30) (arylene) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl, substituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono-or di- (C1-C30) alkylamino, substituted mono-or di- (C6-C30) arylamino, and substituted (C1-C30) alkyl (C6-C30) arylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl, unsubstituted or substituted by one or more (C6-C30) aryl groups; (C6-C30) aryl unsubstituted or substituted by one or more (3-to 30-membered) heteroaryl groups; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino groups unsubstituted or substituted by one or more (C1-C30) alkyl groups; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: (C1-C20) alkyl; (C6-C25) aryl and (3-to 25-membered) heteroaryl. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: (C1-C10) alkyl, (C6-C18) aryl, and (5-to 20-membered) heteroaryl. For example, each substituent independently may be at least one selected from the group consisting of: methyl, phenyl, naphthyl, biphenyl, and dibenzofuranyl.
In the formulas of the present disclosure, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted monocyclic or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof; and preferably, a substituted or unsubstituted mono-or polycyclic (3 to 26 membered) alicyclic or aromatic ring, or a combination thereof. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S.
In this context, the heteroaryl (ene) and heterocycloalkyl (heterocycle) may each independently contain at least one heteroatom selected from B, N, O, S, si and P. Furthermore, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.
In formula 1, A 1 To A 11 Each independently represents N or CR 1 . According to one embodiment of the present disclosure, A 1 To A 11 Each independently represents CR 1 。
R 1 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or two or more adjacentR 1 May be connected to each other to form one or more rings. If there are a plurality of R 1 Each R 1 May be the same or different. According to one embodiment of the present disclosure, R 1 Each independently represents hydrogen, deuterium, unsubstituted (C1-C20) alkyl, unsubstituted (C6-C25) aryl, or unsubstituted (5-to 25-membered) heteroaryl; or two or more adjacent R' s 1 May be connected to each other to form one or more rings. According to another embodiment of the disclosure, R 1 Each independently represents hydrogen, or two or more adjacent R 1 May be connected to each other to form one or more rings. The ring may be a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof; and preferably an unsubstituted mono-or polycyclic (5-to 25-membered) alicyclic or aromatic ring, or a combination thereof. Furthermore, the ring may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. For example, the ring may be a benzene ring, a pyridine ring, a benzofuran ring, a benzothiophene ring, or the like.
In formula 1, X 1 Representation N, NR 3 Or CR (CR) 4 And X is 2 Represents N or C; provided that X 1 And X 2 At least one of which contains N. Specifically, when X 2 When N is represented, X 1 Representation N, NR 3 Or CR (CR) 4 And when X 2 X when C is represented 1 Represents N or NR 3 . For example, when X 2 When N is represented, X 1 Can represent N or CR 4 And when X 2 X when C is represented 1 Can be represented by NR 3 . In the formula (1) of the present invention,represents a single bond or a double bond, respectively, depending on the substituents bonded. For example, when X 2 When N is represented, it is connected to X 2 Upper->Represents a single bond, and when X 1 When N is represented, it is connected to X 1 Upper->Representing a double bond.
R 3 And R is 4 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or may be attached to one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, R 3 And R is 4 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-to 25-membered) heteroaryl. According to another embodiment of the disclosure, R 3 And R is 4 Each independently represents hydrogen, deuterium, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C18) aryl, or unsubstituted (5-to 20-membered) heteroaryl. For example, R 3 Each independently may represent phenyl, and R 4 Each independently may represent hydrogen.
In formula 1, ar 1 And Ar is a group 2 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) arylsilylA substituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group. According to one embodiment of the present disclosure, ar 1 And Ar is a group 2 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 25-membered) heteroaryl, substituted or unsubstituted mono-or di- (C1-C20) alkylamino, substituted or unsubstituted mono-or di- (C6-C25) arylamino, or substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylamino. According to another embodiment of the present disclosure, ar 1 Each independently represents an unsubstituted (C6-C18) aryl group; (5-to 20-membered) heteroaryl, unsubstituted or substituted by one or more (C6-C18) aryl groups and/or one or more (3-to 20-membered) heteroaryl groups; or di (C6-C18) arylamino which is unsubstituted or substituted by one or more (C1-C6) alkyl groups. According to another embodiment of the present disclosure, ar 2 Each independently represents hydrogen, deuterium, unsubstituted (C6-C18) aryl, or unsubstituted (5-to 20-membered) heteroaryl. For example, ar 1 Each independently represents phenyl; a biphenyl group; pyridyl unsubstituted or substituted with one or more phenyl groups; pyrimidinyl unsubstituted or substituted with one or more phenyl groups; triazinyl which is unsubstituted or substituted with at least one of one or more phenyl groups, one or more biphenyl groups, one or more naphthyl groups and one or more dibenzofuranyl groups; quinazolinyl substituted with one or more phenyl groups; quinoxalinyl substituted with one or more phenyl groups; carbazolyl; dibenzofuranyl; benzoquinazolinyl substituted with one or more phenyl groups; benzoquinoxalinyl substituted with one or more phenyl groups; or dimethylfluorenylphenylamino and the like. For example, ar 2 Each independently represents hydrogen, deuterium, phenyl, pyridyl, or the like.
In formula 1, L 1 Each independently represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group.According to one embodiment of the present disclosure, L 1 Each independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5-to 25-membered) heteroarylene group. According to another embodiment of the present disclosure, L 1 Each independently represents a single bond, an unsubstituted (C6-C18) arylene group, or a (5-to 20-membered) heteroarylene group which is unsubstituted or substituted with one or more (C6-C10) aryl groups. For example, L 1 Each independently represents a single bond, phenylene, naphthylene, biphenylene, pyridylene, pyrimidinylene substituted with one or more phenyl groups, triazinylene substituted with one or more phenyl groups, quinazolinylene, quinoxalinylene, benzoquinazolinylene, benzoquinoxalinylene, or the like.
The compound represented by formula 1 may be represented by any one of the following formulas 2 to 8.
In formulae 2 to 4, Y 1 Represents NR 5 O, S or CR 6 R 7 . According to one embodiment of the present disclosure, Y 1 Represents O or S.
In formulae 5 to 7, T 1 To T 4 Each independently represents CR 8 Or N.
In formulae 2 to 8, R 1 、R 2 And R 5 To R 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstitutedA tri (C6-C30) arylsilyl group, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group. If a plurality of R 1 A plurality of R 2 And a plurality of R 8 Each independently of the other, each R 1 Each R 2 And each R 8 May be the same or different. According to one embodiment of the present disclosure, R 1 、R 2 And R 5 To R 8 Each independently represents hydrogen, deuterium, unsubstituted (C1-C20) alkyl, unsubstituted (C6-C25) aryl, or unsubstituted (3-to 25-membered) heteroaryl. According to one embodiment of the present disclosure, R 1 、R 2 And R 5 To R 8 Each independently represents hydrogen or deuterium. For example, R 1 、R 2 And R 5 To R 8 Each independently may represent hydrogen.
In formulas 2 to 8, a each independently represents an integer of 1 or 2; b and c each independently represent an integer of 1 to 4; and d represents an integer of 1 to 3. Each R 1 And each R 2 May be the same or different.
In formulae 2 to 8, A 1 To A 11 、X 1 、X 2 、L 1 、Ar 1 And Ar is a group 2 Is as defined in formula 1 above.
The compound represented by formula 1 may be represented by any one of the following formulas 11 to 13.
In formulae 11 to 13, A 1 To A 11 、R 3 、L 1 、Ar 1 And Ar is a group 2 Is as defined in formula 1 above.
The compound represented by formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.
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The organic electroluminescent compounds of the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the organic electroluminescent compounds of the present disclosure may be prepared by referring to the following reaction scheme, but are not limited thereto.
Reaction scheme 1
Reaction scheme 2
Reaction scheme 3
Reaction scheme 4
Reaction scheme 5
Reaction scheme 6
Reaction scheme 7
Reaction scheme 8
Reaction scheme 9
Reaction scheme 10
In reaction schemes 1 to 10, A 1 To A 11 、X 1 、X 2 、R 1 、R 2 、R 5 、L 1 、Ar 1 And Ar is a group 2 Each as shown in formulas 1 to 8Defined as follows.
Although illustrative synthetic examples of the compounds represented by formula 1 are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartmash (Buchwald-Hartwig) cross-coupling reactions, N-arylation reactions, acidified montmorillonite (H-mont) mediated etherification reactions, miyaura) boronation reactions, suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, pd (II) catalyzed oxidative cyclization reactions, grignard reactions (Grignard reaction), heck reactions (Heck reactions), dehydrocyclization reactions, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, vilsmeier-Haack reaction (Vilsmeier-Haack reaction), etc., and the above reaction proceeds even if a substituent defined in the above formula 1 but not specified in a specific synthesis example is bonded.
The dopant that may be used in combination with the compounds of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant is not particularly limited, but may be preferably selected from a metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from an ortho-metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallized iridium complex compound.
The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following formula 101, but is not limited thereto.
In formula 101, L is selected from structures 1 and 2 below:
R 100 to R 103 And R is 104 To R 107 Each independently represents hydrogen, deuterium, halogen, or noSubstituted or substituted (C1-C30) alkyl substituted by one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to adjacent substituents to form one or more rings. Specifically, adjacent R 100 To R 103 May be linked to each other to form a ring with pyridine, such as a substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline ring;
R 104 to R 107 May be attached to adjacent substituents to form together with benzene one or more rings, for example a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuranopyridine or benzothiophenopyridine ring;
R 201 to R 211 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl substituted by one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to adjacent substituents to form one or more rings; and is also provided with
s represents an integer of 1 to 3.
Specific examples of the dopant are as follows, but are not limited thereto.
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The compound represented by formula 1 of the present disclosure may be included in at least one layer constituting the organic electroluminescent device, and for example, in at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. The compound represented by formula 1 of the present disclosure is not limited thereto, but may be contained in the light emitting layer, and may be contained in the light emitting layer as a host material.
The organic electroluminescent material of the present disclosure, for example, at least one of a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transporting material, and an electron injecting layer, may include a compound represented by formula 1. The material may be a luminescent material. The light emitting material may be composed of only the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent material.
An organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include at least one light emitting layer, and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.
The first electrode and the second electrode may each be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type according to the kind of material forming the first and second electrodes. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.
The organic electroluminescent device of the present disclosure may include the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent device. The organic electroluminescent device including the organic electroluminescent compound represented by formula 1 of the present disclosure may exhibit high luminous efficiency and/or long life characteristics.
The present disclosure may provide a display system by using the compound represented by formula 1. Furthermore, display systems or illumination systems may be produced by using the compounds of the present disclosure. In particular, display systems, such as those for smartphones, tablet computers, notebook computers, PCs, TVs, or automobiles, may be produced by using the compounds of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, the preparation method of the compound according to the present disclosure and its characteristics will be explained in detail. However, the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-15
Synthesis of Compound 1-1
In a reaction vessel, 100g of 1-fluoro-2-nitrobenzene (0.709 mol), 90.4g of 2-chloroaniline (0.709 mol), 59.7g of potassium hydroxide (1.063 mol) and 800mL of dimethyl sulfoxide were added, and the mixture was stirred at 150℃for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 62g of Compound 1-1 (yield: 35%).
Synthesis of Compounds 1-2
In a reaction vessel, 72g of Compound 1-1 (0.290 mol), 326.6g of tin (II) chloride dihydrate (1.448 mol) and 1400mL of ethanol were added, and the mixture was stirred at 70℃for 2 hours. After the reaction was completed, the reaction mixture was slowly cooled to 0 ℃ and then neutralized with aqueous sodium hydroxide solution. After neutralization, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 53g of Compound 1-2 (yield: 63%).
Synthesis of Compound 2-1
In a reaction vessel, 60g of oxindole (0.450 mol), 105mL of N, N-dimethylformamide (1.350 mol), 126mL of phosphorus oxychloride (1.350 mol) and 1200mL of 1, 2-dichloroethylene were added, and the mixture was stirred at 50℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then neutralized with an aqueous potassium carbonate solution. After neutralization, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 35g of Compound 2-1 (yield: 43%).
Synthesis of Compound 2-2
In a reaction vessel, 32.5g of Compound 2-1 (0.181 mol), 33.1g of phenylboronic acid (0.271 mol), 10.5g of tetrakis (triphenylphosphine) palladium (0) (0.009 mol), 48g of potassium carbonate (0.452 mol), 880mL of toluene, 220mL of ethanol and 220mL of distilled water were added, and the mixture was stirred at 130℃for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 38.3g of compound 2-2 (yield: 95%).
Synthesis of Compound 3-1
In a reaction vessel, 20.7g of Compound 1-2 (95.0 mmol), 21g of Compound 2-2 (95.0 mmol), 21.7g of sodium metabisulfite (114.0 mmol) and 320mL of N, N-dimethylformamide were added, and the mixture was stirred at 180℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 19.5g of compound 3-1 (yield: 40%).
Synthesis of Compound 3-2
In a reaction vessel, 19g of Compound 3-1 (45.2 mmol), 1.0g of palladium (II) acetate (4.52 mmol), 3.3g of tricyclohexylphosphine tetrafluoroborate (9.04 mmol), 44.2g of cesium carbonate (135.6 mmol) and 230mL of N, N-dimethylacetamide were added, and the mixture was stirred at 130℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 3.5g of compound 3-2 (yield: 20%).
Synthesis of Compound C-15
In a reaction vessel, 2.7g of Compound 3-2 (7.0 mmol), 1.7g of 2-chloro-4-phenylquinazoline (7.0 mmol), 0.32g of tris (dibenzylideneacetone) dipalladium (0) (0.35 mmol), 0.32mL of tri-tert-butylphosphine (0.70 mmol), 1.7g of sodium tert-butoxide (18.0 mmol) and 135mL of o-xylene were added, and the mixture was stirred at 120℃for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by rotary evaporator. The residue was separated by column chromatography to obtain 2.7g of Compound C-15 (yield: 65%).
The physical properties of the synthesized compounds are summarized in table 1 below.
TABLE 1
| Compounds of formula (I) | Yield (%) | MP(℃) | Tg(℃) |
| C-15 | 65 | 222 | 154 |
H-NMR data of Compound C-15
1 H NMR(600MHz,CDCl 3 ,δ)8.310-8.297(d,1H),8.153-8.128(t,2H),7.652-7.310(t,1H),7.825-7.809(m,1H),7.754-7.726(m,2H),7.639-7.627(d,2H),7.614-7.587(t,1H),7.579-7.565(d,1H),7.469-7.424(m,4H),7.406-7.382(m,6H),7.167-7.121(m,4H)。
Hereinafter, characteristics of an OLED including the compound according to the present disclosure will be explained. However, the following examples only illustrate the characteristics of the OLED according to the present disclosure in detail, and the present disclosure is not limited to the following examples.
Device example 1: producing an OLED comprising a compound according to the disclosure
An OLED comprising an organic electroluminescent compound according to the present disclosure was produced as follows: a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (japanese Ji Aoma limited (GEOMATEC co., ltd., japan)) on a glass substrate for OLED was sequentially subjected to ultrasonic washing with acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Introducing the compound HI-1 into a cell of a vacuum vapor deposition apparatus, and then controlling the pressure in the chamber of the apparatus to 10 -6 And (5) a bracket. Thereafter, a current was applied to the cells to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate. Next, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus,and evaporating the compound by applying a current to the cells, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Then, the compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a first hole transport layer having a thickness of 10nm on the second hole injection layer. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the compound described as a host material in table 2 was introduced as a host into one cell of a vacuum vapor deposition apparatus, and the compound D-39 was introduced as a dopant into the other cell. The two materials were evaporated and the dopant was deposited in a doping amount of 3wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Next, the compound ET-1 and the compound EI-1 were evaporated in two other cells at a rate of 1:1 to deposit an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thereby, an OLED is produced.
Comparative example 1: producing an OLED comprising a compound not according to the present disclosure
An OLED was produced in the same manner as in device example 1, except that the compound CBP was used as a host of the light-emitting layer.
The results of the driving voltage and the light emitting efficiency of the OLEDs produced in the device examples and the comparative examples at a luminance of 1,000 nit, and the time taken for the reduction from 100% initial luminance to 95% luminance at a constant current at a luminance of 5,000 nit (lifetime: T95) are shown in table 2 below.
TABLE 2
As can be confirmed from table 2 above, the OLED including the compound according to the present disclosure as a host material has a low driving voltage and high light emitting efficiency and/or long life compared to the OLED including the conventional organic electroluminescent compound. Further, it can be appreciated that the organic electroluminescent compounds of the present disclosure have a highly condensed structure such that it has a relatively high glass transition temperature (Tg) compared to other organic electroluminescent compounds having similar molecular weights, and thus the compounds of the present disclosure have good thermal stability.
The compounds used in the device examples and comparative examples are shown in table 3 below.
TABLE 3
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Claims (6)
1. An organic electroluminescent compound represented by the following formula 8:
wherein the method comprises the steps of
X 1 And X 2 Represents N;
R 1 represents hydrogen or deuterium;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted phenyl group; and is also provided with
L 1 Represents a substituted or unsubstituted quinazolinylene group, a quinoxalinylene group, a benzoquinazolinylene group or a benzoquinoxalinylene group;
c each independently represents an integer of 1 to 4; d represents an integer of 1 to 3;
wherein if a plurality of R 1 Exists, each R 1 May be the same or different and may be used,
wherein the substituted phenyl group and the substituted quinazoline, quinoxalinylene, benzoquinazoline, and benzoquinoxalinylene substituents are each independently at least one selected from the group consisting of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.
2. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 8 is any one selected from the group consisting of:
3. the organic electroluminescent compound according to claim 1, wherein the compound represented by formula 8 is
4. An organic electroluminescent material comprising the organic electroluminescent compound according to any one of claims 1 to 3.
5. An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 5, wherein the organic electroluminescent compound is contained as a host material.
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| WO2018021841A1 (en) * | 2016-07-27 | 2018-02-01 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR20180099547A (en) * | 2017-02-28 | 2018-09-05 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent device |
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| WO2018021841A1 (en) * | 2016-07-27 | 2018-02-01 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR20180099547A (en) * | 2017-02-28 | 2018-09-05 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent device |
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