CN111868210A - Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same - Google Patents
Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- CN111868210A CN111868210A CN201980018976.2A CN201980018976A CN111868210A CN 111868210 A CN111868210 A CN 111868210A CN 201980018976 A CN201980018976 A CN 201980018976A CN 111868210 A CN111868210 A CN 111868210A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- alkyl
- membered
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 72
- 239000002131 composite material Substances 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- -1 cyano, carboxyl Chemical group 0.000 claims description 239
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 58
- 125000001769 aryl amino group Chemical group 0.000 claims description 36
- 125000005104 aryl silyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 150000002431 hydrogen Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000005549 heteroarylene group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 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 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 239000010410 layer Substances 0.000 description 122
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 239000002019 doping agent Substances 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 17
- 238000007740 vapor deposition Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000001041 indolyl group Chemical group 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical group C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 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 class C1N(CC)CCC2C1C1=CC=C(C)C=C1C2C1=CC=C(C)C=C1 AYJJTPLDSZAGGA-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl 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 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 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
- 239000010408 film Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004957 naphthylene group Chemical group 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
- 230000001590 oxidative effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 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 class C1=CC=NC2=C3CC4=CC=CC=C4C3=CC=C21 ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 0.000 description 1
- QAHMKHHCOXNIHO-UHFFFAOYSA-N 2,4-diphenylquinazoline Chemical group C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QAHMKHHCOXNIHO-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
- 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
- VDDAVZWCRBHDLQ-UHFFFAOYSA-N 2-phenylquinazoline Chemical compound C1=CC=CC=C1C1=NC=C(C=CC=C2)C2=N1 VDDAVZWCRBHDLQ-UHFFFAOYSA-N 0.000 description 1
- QWNCDHYYJATYOG-UHFFFAOYSA-N 2-phenylquinoxaline Chemical compound C1=CC=CC=C1C1=CN=C(C=CC=C2)C2=N1 QWNCDHYYJATYOG-UHFFFAOYSA-N 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
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XDNADZYPWVQFRI-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinoline Chemical class 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 class C1=CC=NC2=C3C4=CC=CC=C4SC3=CC=C21 CWDFYKZZCSEOPO-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical group C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 1
- LJOLGGXHRVADAA-UHFFFAOYSA-N benzo[e][1]benzothiole Chemical group C1=CC=C2C(C=CS3)=C3C=CC2=C1 LJOLGGXHRVADAA-UHFFFAOYSA-N 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=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
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 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
- 238000007639 printing Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition 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
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 125000005558 triazinylene group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D487/16—Peri-condensed systems
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to a composition material for an organic electroluminescent device, various host materials, and an organic electroluminescent device including the same. By including the composition material for an organic electroluminescent device comprising a specific combination of compounds, an organic electroluminescent device having characteristics of high luminous efficiency and/or long life can be produced.
Description
Technical Field
The present disclosure relates to a composition material for an organic electroluminescent device, various host materials, and an organic electroluminescent device including the same.
Background
Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al, Eastman Kodak, Inc. (Eastman Kodak) in 1987 by using a TPD/ALq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. At present, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. For displays that are used for a long time and have high resolution, OLEDs having characteristics of high luminous efficiency and/or long lifetime are required.
Us patent No. 6,902,831 discloses azulene derivatives as organic electroluminescent compounds, and korean patent application laid-open nos. 2016-0022784 and 2017-0001563 disclose an organic electroluminescent device comprising carbazole derivatives and compounds having a carbazole-carbazole structure as a plurality of host compounds. However, there is still a need to develop a method for improving the performance of the organic electroluminescent device.
Disclosure of Invention
Technical problem
An object of the present disclosure is to provide an organic electroluminescent device having characteristics of high luminous efficiency and/or long life by including a composition material for an organic electroluminescent compound comprising a specific combination of compounds.
Solution to the problem
The present inventors found that the above object can be achieved by a composition material for an organic electroluminescent device comprising a compound represented by the following formula 1 and a compound represented by the following formula 2:
wherein
M represents N-L- (Ar)aS or O;
l represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
ar 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 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;
Y1To Y12Each independently represents N or CR1；
R1Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or adjacent R1May be fused to each other to form a substituted or unsubstituted ring; and is
a represents an integer of 1 to 4, wherein if a is an integer of 2 or more, each Ar may be the same or different;
wherein
Ar1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
X1To X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Condensed to form a ring, provided that X1To X8Is not a substituted or unsubstituted carbazolyl group; and is
R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
The invention has the advantages of
By using the composition material for an organic electroluminescent device according to the present disclosure, an organic electroluminescent device having characteristics of high luminous efficiency and/or long life can be produced.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.
The term "composition material for an organic electroluminescent device" in the present disclosure means that at least two materials that can be used for an organic electroluminescent device are present together or are ready to be present together. Herein, "present together" means not only that at least two materials are mixed but also that at least two materials are separated from each other. Further, the composition material for the organic electroluminescent device is a concept covering a material included before (e.g., before vapor deposition) in the organic electroluminescent device and a material included after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the composition material for an organic electroluminescent device may include at least two of a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (host material and/or dopant material), an electron buffering material, a hole blocking material, an electron transport material, and an electron injection material. The composition material for the organic electroluminescent device may include at least two hole injection materials, at least two hole transport materials, at least two hole assist materials, at least two light emission assist materials, at least two electron blocking materials, at least two light emitting materials (host materials and/or dopant materials), at least two electron buffering materials, at least two hole blocking materials, at least two electron transport materials, and/or at least two electron transport materials. The composition material for an organic electroluminescent device of the present disclosure may be contained in any layer constituting the organic electroluminescent device. The at least two materials contained in the composition material may be contained together in one layer or may be contained in different layers, respectively. When at least two materials are contained in one layer, they may be mixedly evaporated to form a layer, or may be separately co-evaporated at the same time to form a layer.
The term "plurality of host materials" in the present disclosure means a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material contained before (e.g., before vapor deposition) in the organic electroluminescent device and a material contained after (e.g., after vapor deposition) in the organic electroluminescent device. For example, the various host materials of the present disclosure may be a combination of at least two host materials, and optionally may further include conventional materials included in the organic electroluminescent material. At least two compounds included in the various host materials of the present disclosure may be included together in one light emitting layer or may be included in different light emitting layers, respectively, by a method known in the art. For example, the at least two compounds may be evaporated in mixture or co-evaporated, or may be evaporated individually.
As used herein, "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "(3-to 7-membered) heterocycloalkyl" means a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably selected from the group consisting of O, S, and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, and the like. "(C6-C30) (arylene) group" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, wherein the number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, phenanthrenyl, anthryl, indenyl, triphenylenyl, pyrenyl, and phenanthrenyl, 
Naphthyl, naphthyl,Fluoranthenyl, spirobifluorenyl, azulenyl and the like. More specifically, the above-mentioned aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthonaphthyl, pyrenyl, 1-
Base 2-
Base 3-
Base, 4-
Base 5-
Base 6-
Radical, benzo [ c]Phenanthryl, benzo [ g ]]
A group, a 1-triphenylene group, a 2-triphenylene group, a 3-triphenylene group, a 4-triphenylene group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 9-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, an o-terphenyl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-quaterphenyl group, a 3-fluoranthyl group, a 4-fluoranthyl group, an 8-fluoranthyl group, a 9-fluoranthyl group, a benzofluoranthyl group, an o, 3, 4-xylyl group, 2, 5-xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-tert-butylphenyl group, p- (2-phenylpropyl) phenyl group, 4 '-methylbiphenyl group, 4' -tert-butyl-p-terphenyl-4-yl group, 9-dimethyl-1-fluorenyl group, 9-dimethyl-2-fluorenyl group, 9-dimethyl-3-fluorenyl group, 9-dimethyl-4-fluorenyl group, 9-diphenylbiphenyl-4-yl group A group of 1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl and the like. "(3-to 50-membered) (arylene) heteroaryl" means an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si and P, and 3 to 50 ring backbone atoms; wherein the number of ring backbone atoms is preferably from 3 to 30, more preferably from 5 to 20; and may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a (arylene) heteroaryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and include monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused-ring heteroaryl groups including benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzonaphthothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, quinoxalinyl, phenanthridinyl, benzodioxolyl and the like. More specifically, the above-mentioned 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, and the like, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl A group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuryl group, 3-benzofuryl group, 4-benzofuryl group, 5-benzofuryl group, 6-benzofuryl group, 7-benzofuryl group, 1-isobenzofuryl group, 3-isobenzofuryl group, 4-isobenzofuryl group, 5-isobenzofuryl group, 6-isobenzofuryl group, 7-isobenzofuryl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 3-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl, 8-isoquinolyl, 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, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-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-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 2-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzothiophenyl, and 4-dibenzo, 4-dibenzothiophenyl, 1-silafluorenyl (1-silafluoryl group), 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl group, 2-germanofluorenyl, 3-germanofluorenyl, and 4-germanofluorenyl. "halogen" includes F, Cl, Br, and I.
Further, "ortho (o-)", "meta (m-)" and "para (p-)" are prefixes, and respectively indicate the relative positions of substituents. The ortho position means that two substituents are adjacent to each other, and for example when two substituents in a benzene derivative occupy positions 1 and 2, it is referred to as ortho position. Meta indicates that the two substituents are at positions 1 and 3, and is referred to as meta, for example, when the two substituents in the benzene derivative occupy positions 1 and 3. Para represents the two substituents at positions 1 and 4, and is referred to as para, for example, when the two substituents in the benzene derivative occupy positions 1 and 4.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., substituent). Ar, L, R1To R9、R16、A1、L1And X1To X8The substituents of substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (arylene) heteroaryl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono-or di-alkylamino, substituted mono-or di-arylamino, and substituted alkylarylamino in (a) are each independently at least one selected from the group consisting of: deuterium; halogen; a 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; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 50-membered) heteroaryl unsubstituted or substituted by (C1-C30) alkyl, (C6-C30) aryl and/or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3-to 50-membered) heteroaryl and/or tris (C6-C30) arylsilyl; a tri (C1-C30) alkylsilyl group; 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; (C1-C30) alkyl (C6- C30) An arylamino group; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. Preferably, the substituent may be at least one selected from the group consisting of: (C1-C20) alkyl; (C6-C25) aryl unsubstituted or substituted with (C1-C20) alkyl and/or (3-to 30-membered) heteroaryl; (3-to 40-membered) heteroaryl and di (C6-C20) arylamino, unsubstituted or substituted with (C1-C20) aryl and/or (C6-C25) aryl. For example, the substituent may be methyl; a tertiary butyl group; phenyl which is unsubstituted or substituted by pyridyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl and/or dibenzothiophenyl; naphthyl unsubstituted or substituted by diphenyltriazinyl; a biphenyl group; a naphthyl phenyl group; a terphenyl group; a dimethyl fluorenyl group; a phenyl fluorenyl group; a diphenylfluorenyl group; phenanthryl; benzophenanthryl; a pyridyl group; triazinyl substituted with at least one of phenyl and naphthyl; indolyl substituted by diphenyl; benzimidazole substituted with phenyl; a quinolyl group; quinazolinyl substituted with phenyl and/or biphenyl; a quinoxalinyl group substituted with a phenyl group; carbazolyl, unsubstituted or substituted with phenyl; a dibenzofuranyl group; a dibenzothienyl group; benzocarbazolyl, unsubstituted or substituted with phenyl; a dibenzocarbazolyl group; benzophenanthrothiophenyl; a diphenylamino group; dimethylfluorenylphenylamino; or a substituted or unsubstituted (16-to 33-membered) heteroaryl group containing at least one of nitrogen, oxygen, or sulfur.
In the formulae of the present disclosure, if adjacent substituents are connected or fused to each other to form a substituted or unsubstituted (3-to 30-membered) ring, the ring may be a monocyclic or polycyclic, alicyclic or aromatic ring, or a combination thereof, wherein the ring may contain at least one heteroatom selected from nitrogen, oxygen and sulfur. For example, the ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.
In the formulae of the present disclosure, the (arylene) groups may each independently contain at least one heteroatom selected from B, N, O, S, Si and P. In addition, the heteroatom may be combined with 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 (5-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 the above formula 1, M represents N-L- (Ar)aS or O.
In formula 1 above, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5-to 18-membered) heteroarylene, wherein the heteroarylene may contain at least one of nitrogen, oxygen, and sulfur. According to an embodiment of the present disclosure, in formula 1, L may represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted benzoxazolinylene group, a substituted or unsubstituted benzothienopyrimidylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted (13-to 16-membered) heteroarylene group containing at least one of nitrogen, oxygen, and sulfur.
In formula 1 above, Ar 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 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; preferably, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-to 30-membered) heteroaryl, or a substituted or unsubstituted di (C6-C25) arylamino; and more preferably, a substituted or unsubstituted (C6-C18) aryl, a substituted or unsubstituted (5-to 25-membered) heteroaryl, or a substituted or unsubstituted di (C6-C18) arylamino.
According to an embodiment of the present disclosure, in formula 1, Ar may represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted benzothienoquinolinyl group, a substituted or unsubstituted benzofuroquinolinyl group, a substituted or unsubstituted triindenyl (triaindenyl) group, a substituted or unsubstituted phenanthroimidazolyl group, a substituted or unsubstituted (9-to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted fluorenylphenylamino group, or a substituted or unsubstituted fluorenylbiphenylamino group.
In formula 1 above, a represents an integer of 1 to 4, preferably 1 or 2. If a is an integer of 2 or more, each Ar may be the same or different.
In the above formula 1, Y1To Y12Each independently represents N or CR1. According to an embodiment of the present disclosure, Y1To Y12All may represent CR1. According to another embodiment of the present disclosure, Y1To Y12May represent N.
In this context, R1Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; or adjacent R1May be fused to each other to form a substituted or unsubstituted ring. Preferably, R 1Represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 25-membered) heteroaryl, or substituted or unsubstituted di (C6-C25) arylamino; or adjacent R1May be fused to each other to form a substituted or unsubstituted, mono-or polycyclic, (C3-C25) aromatic ring, wherein at least one carbon atom of the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. More preferably, R1Represents hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-to 18-membered) heteroaryl, or substituted or unsubstituted di (C6-C18) arylamino; or adjacent R1May be fused to each other to form a substituted or unsubstituted, mono-or polycyclic, (C5-C18) aromatic ring, wherein at least one carbon atom of the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. According to an embodiment of the present disclosure, R1May represent hydrogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenylbiphenylamino group, or the like.
According to an embodiment of the present disclosure, in formula 1, Y1To Y12At least one adjacent pair of (a) represents CR1And two adjacent CR1R of (A) to (B)1Are fused with each other to independently form a ring represented by any one of the following formulas 1-11 to 1-15, but are not limited thereto. In this context, Y1And Y2、R5And Y6And Y9And Y10Are also considered to be adjacent to each other. For example, the ring formed may be a substituted or unsubstituted benzene ring, a naphthalene ring, a furan ring, a thiophene ring, a substituted or unsubstituted pyrrole ring, a pyridine ring, a benzofuran ring, a benzothiophene ring, a substituted or unsubstituted indole ring, a dibenzofuran ring, a dibenzothiophene ring, a substituted or unsubstituted carbazole ring, or a phenanthrene ring, including rings represented by formulas 1-11 to 1-15.
In the above formulas 1-11 to 1-15,
adjacent CR of formula 11C and R in (1)1Fused ofA site.
In the above formulae 1-13 to 1-15, X represents N or CR4. According to embodiments of the present disclosure, all xs may be CR4. According to another embodiment of the present disclosure, at least one X may be N. R4Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; preferably, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-to 25-membered) heteroaryl; and more preferably, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-to 18-membered) heteroaryl.
In the above formulae 1 to 14, R3Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; preferably, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-to 25-membered) heteroaryl; and more preferably, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-to 18-membered) heteroaryl; for example, phenyl。
The compound represented by formula 1 may be represented by the following formula 1-1 or 1-2.
In the above formulas 1-1 and 1-2, M and Y2To Y12As defined in formula 1, and Y13And Y 14Each independently as for Y2As defined.
In the above formula 1-1, Y1Represents N or CR2Wherein R is2Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group.
In the above formula 2, A1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group; preferably an unsubstituted (C6-C25) aryl, or a (5-to 25-membered) heteroaryl unsubstituted or substituted with a (C6-C30) aryl; and more preferably an unsubstituted (C6-C18) aryl, or a (5-to 18-membered) heteroaryl unsubstituted or substituted with a (C6-C18) aryl. For example, A 1May represent a phenyl group; a naphthyl group; a biphenyl group; a terphenyl group; triazinyl substituted with at least one of phenyl, naphthyl and biphenyl; a diphenylpyridyl group; a phenyl quinoline; a phenyl quinoxaline; a phenylquinazoline; a diphenyl quinazoline; quinazolinyl substituted with phenylcarbazole; a dibenzofuranyl group; a dibenzothienyl group; or phenylcarbazolyl.
In the above formula 2, L1Represents a single bond, orSubstituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-to 30-membered) heteroarylene; preferably, a single bond, an unsubstituted (C6-C25) arylene, or an unsubstituted (5-to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5-to 18-membered) heteroarylene. For example, L1May represent a single bond, phenylene, naphthylene, biphenylene, quinolylene, quinoxalylene, quinazolinylene or carbazolyl.
In the above formula 2, X1To X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR 5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Fused to form a ring; preferably, hydrogen, unsubstituted (C6-C25) aryl, or unsubstituted (5-to 25-membered) heteroaryl; or may be adjacent to X1To X8Fused to form a ring; and more preferably, hydrogen, unsubstituted (C6-C18) aryl, or unsubstituted (5-to 18-membered) heteroaryl; or may be adjacent to X1To X8Fused to form a ring. However, X1To X8Is not a substituted or unsubstituted carbazolyl group. For example, X1To X8Each independently may represent hydrogen, phenyl, dibenzofuranyl or dibenzothiophenyl, or may be adjacent to X1To X8Fused to form a benzene ring, a substituted indole ring, a benzothiophene ring, a benzofuran ring, a substituted benzindole ring, a naphthofuran ring, a naphthothiophene ring or an aza ring
And (4) a ring. The substituent of the substituted indole ring may be at least one selected from the group consisting of: unsubstituted or substituted phenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinylPhenyl substituted with dibenzofuranyl and/or dibenzothiophenyl; unsubstituted naphthylphenyl; an unsubstituted biphenyl group; unsubstituted terphenyl; a quinoxalinyl group substituted with a phenyl group; a quinazolinyl group substituted with a phenyl group; and naphthyl substituted by diphenyltriazinyl. The substituent of the substituted benzindole ring may be at least one selected from the group consisting of: phenyl unsubstituted or substituted by benzofuranyl or dibenzothiophenyl; a naphthyl phenyl group; a biphenyl group; and a dibenzofuranyl group.
In the above formula 2, R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
The compound represented by formula 2 may be represented by any one of the following formulae 2-1 to 2-8.
In the above formulae 2-1 to 2-8, A1、L1And X1To X4As defined in formula 2; x9To X38Each independently as for X1Defining; b. e, f, g, h and l each independently represent 1 or 2; c. d and i each independently represent an integer of 1 to 3; j and k each independently represent an integer of 1 to 4; wherein if b to l are integers of 2 or more, X9、X14、X19、X20、X21、X30、X31And X35To X38Each of which may be the same or different. In the above formula 2-2, Z represents O or S.
In the above formulae 2-1 and 2-4 to 2-6, V and W each independently represent a single bond, NR16O or S, provided that both V and W are not simultaneously single bonds and both V and W are not simultaneously NR16. According to an embodiment of the present disclosure, one of V and W may represent a single bond, and the other one represents NR 16O or S.
R16Represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; preferably, a (C6-C25) aryl group unsubstituted or substituted with a (3-to 30-membered) heteroaryl group, or a (5-to 25-membered) heteroaryl group unsubstituted or substituted with a (C6-C30) aryl group; and more preferably a (C6-C18) aryl group unsubstituted or substituted with a (5-to 25-membered) heteroaryl group, or a (5-to 18-membered) heteroaryl group unsubstituted or substituted with a (C6-C18) aryl group. For example, R16May represent phenyl which is unsubstituted or substituted by diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzothienyl and/or dibenzofuranyl; naphthyl substituted with diphenyltriazinyl; a biphenyl group; a terphenyl group; a naphthyl phenyl group; a quinazolinyl group substituted with a phenyl group; or a quinoxalinyl group substituted with a phenyl group.
In the above formulae 2-1 to 2-8, X1To X4And X9To X38Each independently preferably represents hydrogen or an unsubstituted (C6-C25) aryl group; or may be adjacent to X 1To X4And X9To X38Fused to form a ring; more preferably represents hydrogen or an unsubstituted (C6-C18) aryl group; or may be adjacent to X1To X4And X9To X38Fused to form a ring. For example, X1To X4And X9To X30May each independently represent hydrogen or phenyl; x31To X38May represent hydrogen; x1And X2、X3And X4And two adjacent X21Each independently may be fused to each other to form an indole ring substituted with a phenyl group, or an unsubstituted benzene ring.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
The compound represented by formula 1 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared according to the following reaction scheme.
[ reaction scheme 1]
[ reaction scheme 2]
[ reaction scheme 3]
[ reaction scheme 4]
[ reaction scheme 5]
[ reaction scheme 6]
In schemes 1 to 6, L, Ar, Y1To Y12And a is as defined in formula 1.
The compounds represented by formula 2 of the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared by referring to korean patent application laid-open nos. 2015-0135109 (published 2015 at 12/2), 2015-0032447 (published 2015 at 3/26), 2016-0099471 (published 2016 at 8/22), and 2018-0012709 (published 2018 at 2/6), but is not limited thereto.
Meanwhile, the composition material for an organic electroluminescent device of the present disclosure may be various host materials, wherein the compound represented by formula 1 may be a first host material and the compound represented by formula 2 may be a second host material. The composition material for an organic electroluminescent device of the present disclosure may consist of only the first host material represented by formula 1 and the second host material represented by formula 2, or may further include conventional materials included in the host materials. The composition material for an organic electroluminescent device of the present disclosure may include the compound represented by formula 1 and the compound represented by formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70: 30. Further, the compound represented by formula 1 and the compound represented by formula 2 may be combined in amounts of a desired ratio by placing them in a shaker and then mixing them, dissolving them by placing them in a glass tube by heating, and then collecting the resultant, or by dissolving them in a solvent, or the like. According to an embodiment of the present disclosure, there is provided an organic electroluminescent material including a plurality of host materials of the present disclosure.
In addition, an organic electroluminescent device including the compound represented by formula 1 and the compound represented by formula 2 of the present disclosure may be provided. Specifically, the organic electroluminescent device of the present disclosure may include at least one light emitting layer between an anode and a cathode, wherein the light emitting layer may include a host and a dopant, and the host may include the composition material for an organic electroluminescent device of the present disclosure. The organic electroluminescent device of the present disclosure may include a compound represented by formula 1 as a first host material and a compound represented by formula 2 as a second host material.
Herein, the light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. According to an embodiment of the present disclosure, a doping concentration of the dopant compound may be less than 20 wt% with respect to the host compound in the light emitting layer.
The organic electroluminescent device of the present disclosure 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 emission assist layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer.
The dopant included in the organic electroluminescent device of the present disclosure is at least one phosphorescent dopant or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably selected from complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably from complex compounds of ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The dopant included in the organic electroluminescent device according to 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 the following structures 1 to 3:
R100to R103Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be adjacent to R100To R103Linked to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline;
R104To R107Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be adjacent to R104To R107Linked to form a substituted or unsubstituted fused ring, such as a substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;
R201to R220Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkylUnsubstituted (C6-C30) aryl; or may be adjacent to R201To R220Linked to form a substituted or unsubstituted fused ring; and is
n represents an integer of 1 to 3.
Specifically, the dopant compound includes the following compounds, but is not limited thereto.
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 includes a 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 emission 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. Each layer may further be composed of a plurality of layers.
The first and second electrodes may be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-side emission type according to the kind of materials forming the first electrode and the second electrode. 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 layer may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
Further, in the organic electroluminescent device according to the present disclosure, the organic layer may further include at least one metal selected from the group consisting of: an organometallic of a metal of group 1, a metal of group 2, a transition metal of period 4, a transition metal of period 5, a lanthanide and a d-transition element of the periodic table, or at least one complex compound comprising said metals.
In addition, the organic electroluminescent device according to the present disclosure may emit white light by further including at least one light emitting layer including a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound known in the art in addition to the compound according to the present disclosure. In addition, it may further include a yellow or orange light emitting layer, if necessary.
In the organic electroluminescent device according to the present disclosure, at least one layer (hereinafter, "surface layer") is preferably placed on one or more inner surfaces of one or both electrodes; selected from the group consisting of chalcogenide layers, metal halide layers, and metal oxide layers. In particular, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide comprises SiOX(1≤X≤2)、AlOX(X is more than or equal to 1 and less than or equal to 1.5), SiON, SiAlON and the like; the metal halide comprises LiF, MgF2、CaF2Rare earth metal fluorides, etc.; and the metal oxide comprises Cs 2O、Li2O, MgO, SrO, BaO, CaO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. The hole transport layer or the electron blocking layer may also be a multilayer.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be a multi-layer to control injection of electrons and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds at the same time. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein each of the multiple layers may use multiple compounds.
The light emission assisting layer may be disposed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When a light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used to facilitate hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to facilitate electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and the hole transport rate (or the hole injection rate) may be effectively promoted or blocked, thereby enabling control of charge balance. In addition, an electron blocking layer may be disposed between the hole transport layer (or the hole injection layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. When the organic electroluminescent device includes two or more hole transport layers, the hole transport layers further included may serve as a hole assist layer or an electron blocking layer. The hole assist layer and the electron blocking layer may have an effect of improving the efficiency and/or lifetime of the organic electroluminescent device.
In the organic electroluminescent device according to the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the light emitting medium. Further, the hole-transporting compound is oxidized into cations, and thus it becomes easier to inject and transport holes from the mixed region to the light-emitting medium. Preferably, the oxidizing dopant includes various lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers emitting white light.
The organic electroluminescent material according to the embodiments of the present disclosure may be used as a light emitting material for a white organic light emitting device. According to the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light emitting cells, a white organic light emitting device has been proposed to have various structures, such as a parallel arrangement (side-by-side) method, a stacking method, or a Color Conversion Material (CCM) method, etc. In addition, the organic electroluminescent material according to the embodiments of the present disclosure may also be applied to an organic electroluminescent device including QDs (quantum dots).
In order to form each layer constituting the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, or the like may be used.
When a wet film-forming method is used, a thin film is formed by dissolving or dispersing the material constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like. The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvent having no problem in film-forming ability.
The present disclosure may provide a display device using a composition material for an organic electroluminescent device including a compound represented by formula 1 and a compound represented by formula 2. That is, the composition material for an organic electroluminescent device of the present disclosure may be used to produce a display system or a lighting system. Specifically, a display system, such as a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using the composition material for an organic electroluminescent device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, the luminous efficiency and lifetime characteristics of the OLED device improved by including the composition material for an organic electroluminescent device of the present disclosure will be explained. However, the following examples are intended to explain the features of the OLED device including the composition material for an organic electroluminescent device of the present disclosure, and the present disclosure is not limited to the following examples.
Device examples 1 to 18: production of OLED devices comprising the composition materials for OLED devices according to the present disclosure
Product produced by birth
Producing an Organic Light Emitting Diode (OLED) device comprising the composition material for an OLED device according to the present disclosure. A transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomantec, Japan) on a glass substrate for an OLED device was sequentially ultrasonically washed with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of the vacuum vapor deposition apparatus. Introducing a compound HI-1 into a chamber of the vacuum vapor deposition apparatus, and then controlling the pressure inside the chamber of the apparatus to 10-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate. Then, the compound HI-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 injection layer having a thickness of 5nm on the first hole injection layer. A 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. Introducing a compound HT-2 into another chamber of the vacuum vapor deposition apparatus and evaporating the compound by applying an electric current to the chamber, Thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After the hole injection layer and the hole transport layer are formed, a light emitting layer is then deposited as follows. The first and second host compounds shown in table 1 below were introduced as hosts into one cell of the vacuum vapor deposition apparatus, and compound D-39 was introduced into the other cell. Two host materials were evaporated at a rate of 1:1, and a dopant material was simultaneously evaporated at different rates, and these were deposited at a doping amount of 3 wt% 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 transporting layer. The compound ET-1 and the compound EI-1 were then introduced into two additional cells, evaporated at a rate of 1:1, and deposited to form an electron transport layer having a thickness of 35nm on the light-emitting layer. Next, after depositing the compound EI-1 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. Thus, an OLED device was produced.
Comparative example 1: production of OLED devices comprising conventional Compounds
An OLED device was produced in the same manner as in device example 1, except that compound a was used as the second host compound.
The luminous efficiency of the produced OLED device at a luminance of 5,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a constant current and at a luminance of 5,000 nits (lifetime; T95) are provided in table 1 below.
[ Table 1]
From table 1 above, it can be seen that the organic electroluminescent device comprising the compounds represented by formulae 1 and 2 of the present disclosure as a host exhibits higher luminous efficiency and longer life characteristics as compared to the organic electroluminescent device comprising the conventional organic electroluminescent compound. By using the composition material for an organic electroluminescent device of the present disclosure, both of the luminous efficiency and the lifetime characteristics in the organic electroluminescent device, which conflict with each other, can be improved.
The compounds used in the apparatus examples and comparative examples are shown in table 2 below.
[ Table 2]
Claims (10)
1. A composition material for an organic electroluminescent device, the composition material comprising a compound represented by the following formula 1 and a compound represented by the following formula 2:
wherein
M represents N-L- (Ar)aS or O;
l represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
Ar 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 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;
Y1to Y12Each independently represents N or CR1；
R1Represents 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 unsubstitutedSubstituted 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 adjacent R 1May be fused to each other to form a substituted or unsubstituted ring; and is
a represents an integer of 1 to 4, wherein if a is an integer of 2 or more, each Ar may be the same or different;
wherein
Ar1Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-to 30-membered) heteroarylene;
X1to X8Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, -NR5R6or-SiR7R8R9(ii) a Or may be adjacent to X1To X8Condensed to form a ring, provided that X1To X8Is not a substituted or unsubstituted carbazolyl group; and is
R5To R9Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be adjacent to R5To R9Fused to form a ring.
2. The composition material for an organic electroluminescent device according to claim 1, wherein formula 1 is represented by the following formula 1-1 or 1-2:
wherein the content of the first and second substances,
m and Y2To Y12As defined in claim 1;
Y13and Y14Each independently as for Y2Defining; and is
Y1Represents N or CR2Wherein R is2Represents 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 a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group.
3. The composition material for organic electroluminescent device according to claim 1, wherein, in formula 1, Y is 1To Y12At least one adjacent pair of (a) represents CR1And two adjacent CR1R of (A) to (B)1Fused with each other to independently form a ring represented by any one of the following formulas 1-11 to 1-15:
wherein the content of the first and second substances,
x represents N or CR4；
R3And R4Each 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) alkyl di (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, substituted or unsubstituted mono-C6-C30) arylamino, Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; and is
4. The composition material for organic electroluminescent device according to claim 1, wherein Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted benzoisoquinolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted benzothienoquinolinyl group, a substituted or unsubstituted benzofuroquinolinyl group, a substituted or unsubstituted triindenyl group, a substituted or unsubstituted phenanthroimidazolyl group, a substituted or unsubstituted (9-to 25-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenyldiphenylamino group, or a substituted or unsubstituted fluorenylphenylamino group.
5. The composition material for an organic electroluminescent device according to claim 1, wherein formula 2 is represented by any one of the following formulae 2-1 to 2-8:
wherein the content of the first and second substances,
A1、L1and X1To X4As defined in claim 1;
X9to X38Each independently as for X1Defining;
b. e, f, g, h and l each independently represent 1 or 2; c. d and i each independently represent an integer of 1 to 3; j and k each independently represent an integer of 1 to 4; wherein if b to l are integers of 2 or more, X9、X14、X19、X20、X21、X30、X31And X35To X38Each of which may be the same or different;
z represents O or S;
v and W each independently represent a single bond, NR16O or S, provided that both V and W are not simultaneously single bonds and both V and W are not simultaneously NR16(ii) a And areAnd is
R16Represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl.
6. The composition material for organic electroluminescent device according to claim 1, wherein Ar, L, R 1、A1、L1、X1To X8And R5To R9The substituents of substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (arylene) heteroaryl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono-or di-alkylamino, substituted mono-or di-arylamino, and substituted alkylarylamino in (a) are each independently at least one selected from the group consisting of: deuterium; halogen; a 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; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 50-membered) heteroaryl unsubstituted or substituted with (C1-C30) alkyl, (C6-C30) aryl or di (C6-C30) arylamino; (C6-C30) aryl unsubstituted or substituted with cyano, (3-to 50-membered) heteroaryl or tri (C6-C30) arylsilyl; a tri (C1-C30) alkylsilyl group; 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; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronocarbonyl A group; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
7. The composition material for organic electroluminescent device according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
8. the composition material for organic electroluminescent device according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
9. a plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises the compound represented by formula 1 according to claim 1, and the second host material comprises the compound represented by formula 2 according to claim 1.
10. An organic electroluminescent device comprising the composition material for organic electroluminescent device as claimed in claim 1.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20180030943 | 2018-03-16 | ||
| KR10-2018-0030943 | 2018-03-16 | ||
| KR10-2019-0028057 | 2019-03-12 | ||
| KR1020190028057A KR20190109261A (en) | 2018-03-16 | 2019-03-12 | Composition material for organic electroluminescent device, plurality of host materials, and organic electroluminescent device comprising the same |
| PCT/KR2019/002998 WO2019177407A1 (en) | 2018-03-16 | 2019-03-15 | Composition material for organic electroluminescent device, plurality of host materials, and organic electroluminescent device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111868210A true CN111868210A (en) | 2020-10-30 |
Family
ID=68068673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980018976.2A Pending CN111868210A (en) | 2018-03-16 | 2019-03-15 | Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US20210043848A1 (en) |
| KR (1) | KR20190109261A (en) |
| CN (1) | CN111868210A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113416537A (en) * | 2021-06-09 | 2021-09-21 | 上海大学 | Host-guest composition and organic electroluminescent element comprising same |
| CN113501810A (en) * | 2021-06-09 | 2021-10-15 | 浙江华显光电科技有限公司 | Organic compound and organic photoelectric element containing same |
| CN114349741A (en) * | 2021-12-31 | 2022-04-15 | 武汉天马微电子有限公司 | Organic compound and application thereof |
| CN114920748A (en) * | 2022-06-02 | 2022-08-19 | 上海天马微电子有限公司 | Organic compound and application thereof in OLED (organic light emitting diode) device |
| CN115215871A (en) * | 2021-04-16 | 2022-10-21 | 陕西莱特迈思光电材料有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102562401B1 (en) * | 2017-11-28 | 2023-08-03 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR102582803B1 (en) * | 2019-03-25 | 2023-09-27 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR102469106B1 (en) * | 2019-09-11 | 2022-11-21 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR102411143B1 (en) * | 2019-10-17 | 2022-06-20 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR20210054737A (en) * | 2019-11-06 | 2021-05-14 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| CN113801127B (en) * | 2020-07-07 | 2022-11-18 | 北京八亿时空液晶科技股份有限公司 | Oxa-thiaazulene derivatives and their use |
| CN113968863A (en) * | 2020-07-24 | 2022-01-25 | 北京鼎材科技有限公司 | Organic compound and application thereof |
| KR102671850B1 (en) * | 2020-08-10 | 2024-05-31 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic device, organic optoelectronic device and display device |
| WO2022059923A1 (en) * | 2020-09-18 | 2022-03-24 | 주식회사 엘지화학 | Novel compound and organic light-emitting device comprising same |
| CN112209937B (en) * | 2020-10-19 | 2022-02-25 | 宁波卢米蓝新材料有限公司 | Organic nitrogen-containing heterocyclic compound and application thereof |
| KR20220062988A (en) * | 2020-11-09 | 2022-05-17 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic device, organic optoelectronic device and display device |
| KR102349311B1 (en) * | 2021-08-20 | 2022-01-10 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150121337A (en) * | 2014-04-18 | 2015-10-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN106414662A (en) * | 2014-05-23 | 2017-02-15 | 罗门哈斯电子材料韩国有限公司 | Multi-component host material and an organic electroluminescence device comprising the same |
| CN106575663A (en) * | 2014-07-18 | 2017-04-19 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6902831B2 (en) | 2002-11-26 | 2005-06-07 | Canon Kabushiki Kaisha | Azulene-based compounds in organic light emitting device elements |
| KR102445503B1 (en) | 2014-08-20 | 2022-09-22 | 롬엔드하스전자재료코리아유한회사 | Multi-component host material and an organic electroluminescence device comprising the same |
| KR20170001552A (en) | 2015-06-26 | 2017-01-04 | 롬엔드하스전자재료코리아유한회사 | Multi-component host material and organic electroluminescent device comprising the same |
| WO2018159964A1 (en) * | 2017-02-28 | 2018-09-07 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
-
2019
- 2019-03-12 KR KR1020190028057A patent/KR20190109261A/en not_active Application Discontinuation
- 2019-03-15 US US16/981,243 patent/US20210043848A1/en active Pending
- 2019-03-15 CN CN201980018976.2A patent/CN111868210A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150121337A (en) * | 2014-04-18 | 2015-10-29 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN106414662A (en) * | 2014-05-23 | 2017-02-15 | 罗门哈斯电子材料韩国有限公司 | Multi-component host material and an organic electroluminescence device comprising the same |
| CN106575663A (en) * | 2014-07-18 | 2017-04-19 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
| US20170170408A1 (en) * | 2014-07-18 | 2017-06-15 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device |
Non-Patent Citations (3)
| Title |
|---|
| 安玲玲;等: "有机电致发光器件发光材料研究进展-蓝光和绿光材料", 山东化工, vol. 46, no. 14, 23 July 2017 (2017-07-23), pages 39 - 43 * |
| 苏玉苗;等: "咔唑及其衍生物在蓝光OLED中的应用", 化学进展, no. 10, 24 October 2015 (2015-10-24), pages 1384 - 1399 * |
| 马昌期, 等: "有机电致发光空穴传输材料研究进展", 化学进展, vol. 15, no. 06, 24 November 2003 (2003-11-24), pages 495 - 504 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115215871A (en) * | 2021-04-16 | 2022-10-21 | 陕西莱特迈思光电材料有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
| CN115215871B (en) * | 2021-04-16 | 2023-10-31 | 陕西莱特迈思光电材料有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
| CN113416537A (en) * | 2021-06-09 | 2021-09-21 | 上海大学 | Host-guest composition and organic electroluminescent element comprising same |
| CN113501810A (en) * | 2021-06-09 | 2021-10-15 | 浙江华显光电科技有限公司 | Organic compound and organic photoelectric element containing same |
| CN114349741A (en) * | 2021-12-31 | 2022-04-15 | 武汉天马微电子有限公司 | Organic compound and application thereof |
| CN114349741B (en) * | 2021-12-31 | 2023-03-24 | 武汉天马微电子有限公司 | Organic compound and application thereof |
| CN114920748A (en) * | 2022-06-02 | 2022-08-19 | 上海天马微电子有限公司 | Organic compound and application thereof in OLED (organic light emitting diode) device |
| CN114920748B (en) * | 2022-06-02 | 2023-11-10 | 上海天马微电子有限公司 | Organic compound and application thereof in OLED device |
Also Published As
| Publication number | Publication date |
|---|---|
| US20210043848A1 (en) | 2021-02-11 |
| KR20190109261A (en) | 2019-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111868210A (en) | Composition material for organic electroluminescent device, various host materials and organic electroluminescent device comprising the same | |
| CN112930382A (en) | Multiple light emitting materials and organic electroluminescent device comprising the same | |
| CN111801399A (en) | Composition material for organic electroluminescent device, various host materials, and organic electroluminescent device comprising same | |
| CN112679310A (en) | Multiple light emitting materials and organic electroluminescent device comprising the same | |
| CN113015777A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN112585777A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN111566186A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN113661582A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN113950475A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN112300053A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN112209802A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN112955523A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN113072925A (en) | Organic electroluminescent materials and organic electroluminescent device comprising the same | |
| CN113454186A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN114380804A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN114497423A (en) | Organic electroluminescent device | |
| CN113444096A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN112689911A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN112437989A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN112119139A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN114085202A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN111511879A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN113698304A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| CN113410415A (en) | Multiple host materials and organic electroluminescent device comprising the same | |
| CN113372257A (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |