CN116514629A - Multiple host materials and organic electroluminescent device comprising the same - Google Patents
Multiple host materials and organic electroluminescent device comprising the same Download PDFInfo
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- CN116514629A CN116514629A CN202310062074.7A CN202310062074A CN116514629A CN 116514629 A CN116514629 A CN 116514629A CN 202310062074 A CN202310062074 A CN 202310062074A CN 116514629 A CN116514629 A CN 116514629A
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- substituted
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- membered
- alkyl
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- 239000000463 material Substances 0.000 title claims abstract description 154
- 150000001875 compounds Chemical class 0.000 claims abstract description 167
- 125000003118 aryl group Chemical group 0.000 claims description 117
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 105
- 229910052805 deuterium Inorganic materials 0.000 claims description 105
- 125000005104 aryl silyl group Chemical group 0.000 claims description 100
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 89
- 125000001072 heteroaryl group Chemical group 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 34
- 125000001931 aliphatic group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 32
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 17
- 125000005549 heteroarylene group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000004973 liquid crystal related substance Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 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 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 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
- 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
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 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
- 125000003107 substituted aryl 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- -1 polycyclic hydrocarbon Chemical class 0.000 description 257
- 239000010410 layer Substances 0.000 description 142
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 62
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- 230000000903 blocking effect Effects 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 125000003373 pyrazinyl group Chemical group 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 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
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ANSIWEGOCFWRSC-UHFFFAOYSA-N 1,2-dimethyl-1h-indene Chemical class C1=CC=C2C(C)C(C)=CC2=C1 ANSIWEGOCFWRSC-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YQDSWSPIWVQKBC-UHFFFAOYSA-N 1h-cyclopenta[l]phenanthrene Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1CC=C2 YQDSWSPIWVQKBC-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102100039856 Histone H1.1 Human genes 0.000 description 2
- 101001035402 Homo sapiens Histone H1.1 Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- 150000002475 indoles Chemical group 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004957 naphthylene group Chemical class 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- ZARCYQBIHIVLOO-UHFFFAOYSA-N pyridine;triazine Chemical compound C1=CC=NC=C1.C1=CN=NN=C1 ZARCYQBIHIVLOO-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl 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
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 125000006835 (C6-C20) arylene group Chemical class 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 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
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GVOCEFPRUHNACL-UHFFFAOYSA-N 5-tert-butyl-2,5-diphenylcyclohexa-1,3-diene Chemical group C(C)(C)(C)C1(CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 GVOCEFPRUHNACL-UHFFFAOYSA-N 0.000 description 1
- CUFNKYGDVFVPHO-UHFFFAOYSA-N Azulene Natural products C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005870 benzindolyl group Chemical group 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 150000001616 biphenylenes Chemical class 0.000 description 1
- 125000005566 carbazolylene group Chemical class 0.000 description 1
- 150000001768 cations Chemical class 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
- 238000000576 coating method Methods 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 150000002469 indenes Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 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
- 230000007774 longterm Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical class 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
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- 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
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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Abstract
The present disclosure relates to a plurality of host materials comprising at least one first host compound represented by formula 1 and at least one second host compound represented by formula 2, wherein the first host compound and the second host compound are different from each other; and an organic electroluminescent device comprising the plurality of host materials. Furthermore, the present disclosure relates to a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by formula 2', and wherein the first host compound and the second host compound are different from each other; and an organic electroluminescent device comprising the plurality of host materials. By including a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device having significantly improved driving voltage, current efficiency, and/or lifetime characteristics may be provided.
Description
Technical Field
The present disclosure relates to a variety of host materials and an organic electroluminescent device including the same.
Background
In 1987, tang et al, eastman Kodak, had developed for the first time a method of forming a light-emitting layer and a charge-transporting layer by using TPD/Alq 3 Double-layered small molecule green organic electroluminescent devices (OLEDs). Thereafter, the development of the OLED is rapidly completed and the OLED has been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel realization. However, in many applications such as TV and lighting devices, the lifetime of the OLED is insufficient and still a higher efficiency of the OLED is required. In general, the lifetime of an OLED becomes shorter as the luminance of the OLED becomes higher. Accordingly, for long-term use and high resolution displays, OLEDs having high luminous efficiency and/or long lifetime are required.
Various materials or concepts for organic layers of organic electroluminescent devices have been proposed in order to improve luminous efficiency, driving voltage and/or lifetime, but they are not satisfactory in practical use. Accordingly, there has been a continued need to develop organic electroluminescent materials having improved properties (e.g., improved driving voltage, luminous efficiency, power efficiency, and/or lifetime characteristics) compared to the combination of the specific compounds previously disclosed.
Meanwhile, japanese patent application laid-open No. 2015-18883 discloses various host materials containing anthracene and/or cyclopentaphenanthrene structures, and korean patent application laid-open No. 2019-0140421 discloses compounds containing anthracene structures as host materials. In addition, chinese patent application publication No. 110294663 discloses a compound containing a cyclopentaphenanthrene structure as a host material. However, the foregoing references do not specifically disclose the specific combinations of host materials claimed in the present disclosure. Furthermore, there has been a continuing need to develop luminescent materials with more improved properties (e.g., improved driving voltage, luminous efficiency, power efficiency and/or lifetime characteristics) compared to the compounds disclosed in the aforementioned references.
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide host materials capable of producing an organic electroluminescent device having a low driving voltage, high current efficiency and/or improved lifetime characteristics. It is another object of the present disclosure to provide an organic electroluminescent device having a low driving voltage, high current efficiency, and/or improved lifetime characteristics by including a specific combination of compounds according to the present disclosure as a variety of host materials.
Solution to the problem
As a result of intensive studies to solve the above technical problems, the present inventors have found that the above objects can be achieved by a plurality of host materials comprising at least one first host compound represented by the following formula 1 and at least one second host compound represented by the following formula 2, wherein the first host compound and the second host compound are different from each other. Furthermore, the inventors of the present invention found that the above object can be achieved by a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by the following formula 2', and wherein the first host compound and the second host compound are different from each other.
In the formula (1) of the present invention,
L 1 and L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 1 to R 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-membered) A substituted or unsubstituted (C1-C30) heterocycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri (C1-C30) alkylsilyl, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, a substituted or unsubstituted tri (C6-C30) arylsilyl, a substituted or unsubstituted (C3-C30) aliphatic ring or rings and a substituted or unsubstituted (C6-C30) aromatic ring, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino, a substituted or unsubstituted mono-or di- (C2-C30) alkenylamino, a substituted or unsubstituted mono-or di- (C6-C30) arylamino, a substituted or unsubstituted mono-or di- (3-to 30) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl (C2-alkenyl (C2-C30) alkylamino, a substituted or unsubstituted (C1-C30) alkylamino, a substituted or unsubstituted (C2-C30) alkylamino, a substituted or unsubstituted (C30-C30) alkylamino, an aryl amino Or a substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino group; and is also provided with
a and b each independently represent an integer of 1 or 2, wherein each Ar, if a and b are 2 1 And each Ar 2 May be the same or different from each other;
in the formula (2) of the present invention,
Ar A represents the following formula A-1 or A-2:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
T 2 Represents CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
ring C represents a substituted or unsubstituted naphthalene ring;
R 11 to R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused ring, or an aromatic group L, or an unsubstituted fused ring 13 -N(Ar 13 )(Ar 14 )；
R 19 、R 20 And R is 31 To R 34 Each independently represents and L 12 A site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-C7) heterocycloalkyl, 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, one or more fused (C3-C30) aliphatic rings and one or more (C6-C30) alicyclic rings or an unsubstituted or aromatic group, L-or L-substituted or unsubstituted aryl group 13 -N(Ar 13 )(Ar 14 )；
R a And R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group,Or a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 to L 13 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
Ar 13 And Ar is a group 14 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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.
In the formula 2' of the present invention,
Ar A represents the following formula A-1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
R 11 To R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more (C6-C30) fused ring-substituted or unsubstituted aromatic groups;
R 19 and R is 20 Each independently represents and L 12 A site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more (C6-C30) fused ring-substituted or unsubstituted aromatic groups;
R a And R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene groupAn aryl group; and is also provided with
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
The beneficial effects of the invention are that
An organic electroluminescent device having a lower driving voltage, higher current efficiency, and/or improved lifetime characteristics as compared to conventional organic electroluminescent devices may be manufactured by including a specific combination of compounds according to the present disclosure as various host materials, and a display system or an illumination system may be manufactured using the organic electroluminescent device.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure.
The present disclosure relates to a plurality of host materials including a first host material including at least one compound represented by formula 1 and a second host material including at least one compound represented by formula 2, wherein the compound represented by formula 1 and the compound represented by formula 2 are different from each other; and an organic electroluminescent device comprising the host material. Furthermore, the present disclosure relates to a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by formula 2', and wherein the first host compound and the second host compound are different from each other.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any material layer constituting the organic electroluminescent device as needed.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The term "plurality of organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of two or more compounds, which materials may be contained in any layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of organic electroluminescent materials may be a combination of two or more compounds, which may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two or more compounds may be contained in the same layer or different layers, and may be mixed evaporated or co-evaporated, or may be evaporated separately.
The term "multiple host materials" in the present disclosure means an organic electroluminescent material comprising a combination of two or more host materials. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. The plurality of host materials of the present disclosure may be contained in any light emitting layer constituting an organic electroluminescent device, wherein two or more compounds contained in the plurality of host materials may be contained together in one light emitting layer or may be contained in different light emitting layers, respectively. When two or more host materials are contained in one layer, for example, they may be mixed and evaporated to form a layer, or they may be simultaneously co-evaporated separately to form a layer.
In this context, the term "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like.
The term "(C6-C30) aryl", "(C6-C30) arylene" or "(C6-C30) aromatic hydrocarbon" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having from 6 to 30 ring backbone carbon atoms, which may be partially saturated, wherein the number of ring backbone carbon atoms is preferably from 6 to 20, and more preferably from 6 to 15. The aryl group may include a spiro structure. The aryl group may include phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, naphthacene, perylenyl, benzofluorenyl, and the like,Radical, benzo->Group, naphto-naphthyl group, fluoranthenyl group, benzofluoranthenyl group, tolyl group, xylyl group, mesityl group, cumenyl group, spiro [ fluorene-fluorene ]]Base, spiro [ fluorene-benzofluorene ]]Radicals, azulene radicals, tetramethyl dihydrophenanthryl radicals, and the like. More specifically, the aryl group may include o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl Phenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl 9, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl 9, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11-dimethyl-1-benzo [ a ]]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ] ]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-)8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ]]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ] ]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl, 11-diphenyl-3-benzo [ c ]]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9 10-dihydro-4-phenanthryl and the like.
The term "(3-to 30-membered) heteroaryl", "(3-to 30-membered) heteroarylene" or "(3-to 30-membered) heteroarene" in the present disclosure means an aryl or arylene group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si and P. The number of ring skeleton atoms is preferably 3 to 30, and more preferably 5 to 20. It may be a single ring or a fused ring condensed with at least one benzene ring, and may be partially saturated. In addition, the above heteroaryl or heteroarylene group includes a heteroaryl or heteroarylene group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and may include a spiro structure. The above heteroaryl group may include monocyclic heteroaryl groups such as 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, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzobenzoquinolinyl, benzobenzobenzoquinazolinyl, benzonaphthyridinyl, naphthofuranpyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzonaphthyridinyl, benzofuranpyrimidinyl, benzoquinolinyl, benzofuranyl, benzoquinolinyl, and benzoquinolinyl, benzoquinolinyl benzothiophenopyrimidinyl, naphthyridopyrimidinyl, pyrimidoindolyl, benzopyrimidino indolyl, benzofuranopyrazinyl, naphtofuranopyrazinyl, benzothiophenopyrazinyl, naphtofenaopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzofuranopyrazinyl, benzofuranyl, naphthyridinyl, benzofuranyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolicidinyl, acridinyl, silafluorenyl, germanium fluorenyl, benzotriazole yl, phenazinyl, imidazopyridinyl, chromenequinazolinyl, thiochromenoquinazolinyl, dimethylphenylpyrimidinyl, indolocarbazolyl, indenocarbazolyl, and the like. More specifically, the process is carried out, heteroaryl groups may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-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-indolicidinyl, 2-indolicidinyl, 3-indolicidinyl, 5-indolicidinyl, 6-indolicidinyl, 7-indolicidinyl, 8-indolicidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 3-phenanthridinyl, 2-thienyl, 3-thienyl, 2-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzo- [ 2-benzo-3-benzofuranyl, 2-benzofuranyl ] -2- [2, 2-b ] -2-naphtho-1-benzofuranyl, 2- [ b ] -2, 2-b ] -2-naphtalenyl 5-naphtho- [1,2-b ] -benzofuranyl, 6-naphtho- [1,2-b ] -benzofuranyl, 7-naphtho- [1,2-b ] -benzofuranyl, 8-naphtho- [1,2-b ] -benzofuranyl, 9-naphtho- [1,2-b ] -benzofuranyl, 10-naphtho- [1,2-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-naphtho- [2,3-b ] -benzofuranyl, 3-naphtho- [2,3-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 6-naphtho- [2,3-b ] -benzofuranyl, 7-naphtho- [2,3-b ] -benzofuranyl, 8-naphtho- [2,3-b ] -benzofuranyl, 9-naphtho- [2,3-b ] -benzofuranyl, 10-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2, 2-b ] -benzofuranyl, 5-naphtho-b ] -benzofuranyl, 6-naphtho- [2,1-b ] -benzofuranyl, 7-naphtho- [2,1-b ] -benzofuranyl, 8-naphtho- [2,1-b ] -benzofuranyl, 9-naphtho- [2,1-b ] -benzofuranyl, 10-naphtho- [2,1-b ] -benzofuranyl, 1-naphtho- [1,2-b ] -benzothienyl, 2-naphtho- [1,2-b ] -benzothienyl, 3-naphtho- [1,2-b ] -benzothienyl, 4-naphtho- [1,2-b ] -benzothienyl, 5-naphtho- [1,2-b ] -benzothienyl, 6-naphtho- [1,2-b ] -benzothienyl 7-naphtho- [1,2-b ] -benzothienyl, 8-naphtho- [1,2-b ] -benzothienyl, 9-naphtho- [1,2-b ] -benzothienyl, 10-naphtho- [1,2-b ] -benzothienyl, 1-naphtho- [2,3-b ] -benzothienyl, 2-naphtho- [2,3-b ] -benzothienyl, 3-naphtho- [2,3-b ] -benzothienyl, 4-naphtho- [2,3-b ] -benzothienyl, 5-naphtho- [2,3-b ] -benzothienyl, 1-naphtho- [2,1-b ] -benzothienyl, 2-naphtho- [2,1-b ] -benzothienyl, 3-naphtho- [2,1-b ] -benzothienyl, 4-naphtho- [2,1-b ] -benzothienyl, 5-naphtho- [2,1-b ] -benzothienyl, 6-naphtho- [2,1-b ] -benzothienyl, 7-naphtho- [2,1-b ] -benzothienyl, 8-naphtho- [2,1-b ] -benzothienyl, 9-naphtho- [2,1-b ] -benzothienyl, 10-naphtho- [2,1-b ] -benzothienyl, 2-benzofuro [3,2-d ] pyrimidinyl, 6-benzofuro [3,2-d ] pyrimidinyl, 7-benzofuro [3,2-d ] pyrimidinyl, 8-benzofuro [3,2-d ] pyrimidinyl, 9-benzofuro [3,2-d ] pyrimidinyl, 2-benzothio [3,2-d ] pyrimidinyl, 6-benzo [3, 1-b ] -benzothienyl, 6-benzo [2, 1-d ] pyrimidinyl, 6-benzo [3, 1-b ] -benzothienyl, 2-benzofuro [3,2-d ] pyrimidinyl, 6-benzofuro [3,2-d ] pyrazinyl, 7-benzofuro [3,2-d ] pyrazinyl, 8-benzofuro [3,2-d ] pyrazinyl, 9-benzofuro [ 2-d ] 2-d-naphtyl, 6-benzofurano [2, 2-d ] pyrazinyl, 6-b-benzofurano [ 2-d-b ] pyrazinyl, 2-benzothio [3,2-d ] pyrazinyl, 6-benzothio [3,2-d ] pyrazinyl, 7-benzothio [3,2-d ] pyrazinyl, 8-benzothio [3,2-d ] pyrazinyl, 9-benzothio [3,2-d ] pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, and the like.
The term "fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings" means at least one fused ring group of an aliphatic ring having 3 to 30 ring backbone carbon atoms, preferably 3 to 25 ring backbone carbon atoms, and more preferably 3 to 18 ring backbone carbon atoms, and at least one aromatic ring having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, and more preferably 6 to 18 ring backbone carbon atoms, for example, a fused ring group of at least one benzene and at least one cyclohexane, or a fused ring group of at least one naphthalene and at least one cyclopentane, and the like. In the present disclosure, the carbon atoms of the fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings may be replaced by at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. In the present disclosure, "halogen" includes F, cl, br and I.
In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2. Meta indicates that two substituents are in positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is referred to as meta. Para indicates that two substituents are in positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is referred to as para.
The term "ring formed by the connection of adjacent substituents" means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring or combination thereof, preferably a substituted or unsubstituted mono-or polycyclic (5-to 25-membered) alicyclic or aromatic ring or combination thereof. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is 5 to 20, and according to another embodiment of the present disclosure, the number of ring backbone atoms is 5 to 15. For example, the fused ring may take the form: 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 benzofluorene 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, a substituted or unsubstituted carbazole ring, and the like.
Further, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced with a group formed by the connection of two or more substituents among the above-mentioned substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazines may be interpreted as heteroaryl substituents, or substituents in which two heteroaryl groups are linked. In the formulas of the present disclosure, one or more substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring groups of the one or more aliphatic rings and the one or more aromatic rings, substituted mono-or di-alkylamino, substituted mono-or di-alkenylamino, substituted mono-or di-arylamino, substituted mono-or di-heteroarylamino, substituted alkylalkylenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted arylheteroarylamino, substituted aromatic hydrocarbon ring, substituted heteroaromatic ring, and substituted naphthalene ring are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (C1-C30) alkyl unsubstituted or substituted by deuterium; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; a (3-to 30-membered) heteroaryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups; (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, one or more (C1-C30) alkyl groups, one or more (C6-C30) aryl groups and one or more (3-to 30-membered) heteroaryl groups; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylborocarbonyl; (C6-C30) arylphosphines; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl, which may be further substituted with deuterium. According to one embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; (C1-C20) alkyl unsubstituted or substituted by deuterium; a (3-to 20-membered) heteroaryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C20) aryl groups; and (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, one or more (C1-C20) alkyl groups, one or more (C6-C20) aryl groups, and one or more (6-to 20-membered) heteroaryl groups. For example, the one or more substituents may each independently be at least one selected from the group consisting of: deuterium, methyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl and carbazolyl, wherein the above substituents may be further substituted with deuterium.
Hereinafter, a plurality of host materials according to one embodiment will be described in more detail.
The plurality of host materials according to the present disclosure include a first host material and a second host material, wherein the first host material includes at least one compound represented by formula 1, and the second host material includes at least one compound represented by formula 2, wherein the compound represented by formula 1 and the compound represented by formula 2 are different from each other.
A first host material that is a host material according to one embodiment is represented by the following formula 1.
In the formula (1) of the present invention,
L 1 and L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 1 to R 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-C7) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused rings, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) arylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, substituted or unsubstituted amino Substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino; and is also provided with
a and b are each independentlyAn integer representing 1 or 2, wherein each Ar, if a and b are 2 1 And each Ar 2 May be the same or different from each other.
According to one embodiment of the present disclosure, L 1 And L 2 Each independently represents a single bond or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond or an unsubstituted or deuterium-substituted (C6-C20) arylene group. For example, L 1 And L 2 Each independently may be a single bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted naphthylene, or unsubstituted or deuterium-substituted phenanthrylene.
According to one embodiment of the present disclosure, ar 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, preferably a (C6-C30) aryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups, and more preferably a (C6-C28) aryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C20) aryl groups. For example, ar 1 And Ar is a group 2 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group, wherein one or more substituents of the substituted phenyl group, the substituted biphenyl group, the substituted terphenyl group, the substituted naphthyl group, and the substituted phenanthryl group may each independently be at least one of deuterium, phenyl group, biphenyl group, terphenyl group, naphthyl group, and phenanthryl group.
According to one embodiment of the present disclosure, R 1 To R 8 May each independently be hydrogen or deuterium.
The second host material, which is the other host material according to one embodiment, includes a compound represented by the following formula 2.
In the formula (2) of the present invention,
Ar A represents the following formula A-1 or A-2:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
T 2 Represents CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
ring C represents a substituted or unsubstituted naphthalene ring;
R 11 to R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused ring, or an aromatic group L, or an unsubstituted fused ring 13 -N(Ar 13 )(Ar 14 )；
R 19 、R 20 And R is 31 To R 34 Each independently represents and L 12 A site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstitutedDi (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 fused ring groups of one or more (C3-C30) aliphatic and one or more (C6-C30) aromatic rings, or-L 13 -N(Ar 13 )(Ar 14 )；
R a And R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 to L 13 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
Ar 13 And Ar is a group 14 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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.
According to one embodiment of the present disclosure, ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring, preferably a substituted or unsubstituted (C6-C20) aromatic hydrocarbon ring, or a substituted or unsubstituted (6-to 20-membered) heteroaromatic hydrocarbon ring, and more preferably a (C6-C20) aromatic hydrocarbon ring that is unsubstituted or substituted with deuterium and at least one of one or more (C1-C10) alkyl groups; or a (6-to 20-membered) heteroarene ring that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C15) aryl groups. For example, ring a and ring B may each independently be a benzene ring, a naphthalene ring, a dimethylfluorene ring, a dibenzofuran ring, or a carbazole ring substituted with one or more phenyl groups, which may be further substituted with deuterium.
According to one embodiment of the present disclosure, ring C may be an unsubstituted or deuterium substituted naphthalene ring.
According to one embodiment of the present disclosure, R 19 And R is 20 Can each independently be with L 12 A site of ligation; or may be hydrogen or deuterium.
According to one embodiment of the present disclosure, R 11 To R 18 May each independently be hydrogen or deuterium.
According to one embodiment of the present disclosure, R 31 To R 34 Can each independently be with L 12 A site of ligation; or may be hydrogen or deuterium.
According to one embodiment of the present disclosure, R a And R is b May each independently represent a substituted or unsubstituted (C1-C20) alkyl group, preferably a substituted or unsubstituted (C1-C10) alkyl group. For example, R a And R is b Each independently may be a methyl group unsubstituted or substituted with deuterium.
According to one embodiment of the present disclosure, L 11 To L 13 Each independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (3-to 28-membered) heteroarylene group, preferably a single bond; (C6-C18) arylene, unsubstituted or substituted with deuterium; or unsubstituted or deuterium-substituted (6-to 20-membered) heteroarylene. For example, L 11 To L 13 Each independently may be a single bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted naphthylene, or unsubstituted or deuterium-substituted carbazolylene.
According to one embodiment of the present disclosure, ar 11 Represents a substituted or unsubstituted (C6-C28) aryl orA (C6-C28) aryl group substituted or unsubstituted (3-to 25-membered) heteroaryl group, preferably unsubstituted or substituted with at least one of deuterium, one or more (C1-C10) alkyl groups, one or more (C6-C20) aryl groups and one or more (6-to 25-membered) heteroaryl groups; or a (3-to 25-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and one or more (C6-C20) aryl groups. For example, ar 11 May be at least one of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dimethylfluorenyl, spirobifluorenyl, benzofluorenyl, dimethylbenzofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzonaphthofuranyl, or benzonaphthothiophenyl, wherein the one or more substituents may be at least one of deuterium, methyl, phenyl, biphenyl, naphthyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.
According to one embodiment of the present disclosure, ar A Can be represented by any one of the following formulas b-1 to b-4.
In formulae b-1 to b-4,
R 21 To R 26 Each independently represents and L 12 A site of ligation; or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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 di (C1-C30) arylsilyl(C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings,
R 35 to R 42 Is as for R 31 To R 34 Defined, and
T 1 、T 2 、R 19 、R 20 and R is 31 To R 34 Is as defined in formula 2.
According to one embodiment of the present disclosure, R 21 To R 26 Each independently represents and L 12 The site of attachment, or represents hydrogen or deuterium; or may be attached to one or more adjacent substituents to form one or more rings. According to one embodiment of the present disclosure, by R 21 To R 26 The one or more rings formed by the attachment of adjacent substituents of (a) may be a substituted or unsubstituted monocyclic or polycyclic (3-to 30-membered) alicyclic or aromatic ring or a combination thereof, which may contain at least one heteroatom selected from B, N, O, S, si and P. For example, by R 21 To R 26 The one or more rings formed by the connection of adjacent substituents of (a) may be an unsubstituted or deuterium-substituted benzene ring, an unsubstituted or deuterium-substituted dimethylindene ring, an unsubstituted or deuterium-substituted benzofuran ring, or an unsubstituted or deuterium-substituted phenylindole ring, etc.
According to one embodiment of the present disclosure, formula 2 may be represented by the following formula 2-1 or 2-2.
In formulas 2-1 and 2-2,
R 21 to R 26 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenylSubstituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings,
R 27 to R 29 Each independently represents and L 12 The site of attachment, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, or-L 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings, an
T 1 、R 11 To R 20 、L 11 To L 13 、Ar 11 、Ar 13 And Ar is a group 14 Is as defined in formula 2.
According to one embodiment of the present disclosure, R 21 To R 26 Each independently represents hydrogen or deuterium; or may be attached to one or more adjacent substituents to form one or more rings. According to one of the present disclosure In one embodiment, R is 21 To R 26 The one or more rings formed by the attachment of adjacent substituents of (a) may be a substituted or unsubstituted monocyclic or polycyclic (3-to 30-membered) alicyclic or aromatic ring or a combination thereof, which may contain at least one heteroatom selected from B, N, O, S, si and P. For example, by R 21 To R 26 The one or more rings formed by the connection of adjacent substituents of (a) may be an unsubstituted or deuterium-substituted benzene ring, an unsubstituted or deuterium-substituted dimethylindene ring, an unsubstituted or deuterium-substituted benzofuran ring, or an unsubstituted or deuterium-substituted phenylindole ring, etc.
According to one embodiment of the present disclosure, R 27 To R 29 Each independently represents and L 12 The site of attachment, or represents hydrogen or deuterium.
According to one embodiment of the present disclosure, formula 2 may be represented by the following formula 3-1.
In the formula 3-1 of the present invention,
R 31 to R 38 And R is 40 Is as for R 11 To R 18 Defined, and T 2 、R 11 To R 18 、L 11 、L 12 And Ar is a group 11 Is as defined in formula 2.
According to one embodiment of the present disclosure, at least one of formulas 1 and 2 may include deuterium.
According to one embodiment of the present disclosure, the first host material represented by formula 1 may be more specifically exemplified as the following compound, but is not limited thereto.
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In the compounds C-56 to C-100, C-102 and C-104, dn means that n number of hydrogen atoms are replaced with deuterium, and n is an integer from 1 to 34. Specifically, n is at least 1 and is an integer equal to the maximum number of hydrogen atoms in the compound.
According to one embodiment of the present disclosure, if the compound represented by formula 1 contains deuterium, the compound contains at least one deuterium, preferably R 1 To R 8 At least one of them contains deuterium, more preferably R 1 To R 8 and-L 1 -(Ar 1 ) a Containing at least one deuterium, still more preferably R 1 To R 8 Each of, -L 1 -(Ar 1 ) a and-L 2 -(Ar 2 ) b Contains at least one deuterium. According to one embodiment of the present disclosure, if the compound represented by formula 1 contains deuterium, the deuterium substitution rate is preferably 20% or more, more preferably 30% or more, still more preferably 40% or more, still more preferably 45% or more of the total number of hydrogen atoms. The compound having formula 1 substituted with deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.
According to one embodiment of the present disclosure, the second host material represented by formula 2 may be more specifically exemplified as the following compound, but is not limited thereto.
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In the compounds H1-226 to H1-285 and H1-291 to H1-295, dn means that n number of hydrogen atoms are replaced with deuterium, and n is an integer from 1 to 30. Specifically, n is at least 1 and is an integer equal to the maximum number of hydrogen atoms in the compound.
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In the compounds H2-66 to H2-115, dn means that n number of hydrogen atoms are replaced with deuterium, and n is an integer from 1 to 33. Specifically, n is at least 1 and is an integer equal to the maximum number of hydrogen atoms in the compound.
According to one embodiment of the present disclosure, if the compound represented by formula 2 contains deuterium, the compound contains at least one deuterium, preferably R 11 To R 18 At least one of them contains deuterium, more preferably R 11 To R 18 and-L 11 -Ar 11 Deuterium containing; or R is 11 To R 18 and-L 12 -Ar A Containing at least one deuterium, still more preferably R 11 To R 18 Each of, -L 11 -Ar 11 and-L 12 -Ar A Contains at least one deuterium. According to one embodiment of the present disclosure, if the compound represented by formula 2 contains deuterium, the deuterium substitution rate is preferably 20% or more, more preferably 30% or more, still more preferably 40% or more, and still more preferably 45% or more of the total number of hydrogen atoms. The compound having formula 2 substituted with deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.
Hereinafter, a variety of host materials according to one embodiment of the present disclosure will be described in detail.
The plurality of host materials according to the present disclosure comprise at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by the following formula 2', and wherein the first host compound and the second host compound are different from each other.
The first host compound and the second host compound, which are host materials according to one embodiment of the present disclosure, are represented by the following formula 2'.
In the formula 2' of the present invention,
Ar A represents the following formula A-1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
R 11 to R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C3) 0) An arylsilyl group, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings;
R 19 and R is 20 Each independently represents and L 12 The attached site, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more fused ring-C6-C30 aromatic groups;
R a and R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 And L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
According to one embodiment of the present disclosure, formula 2' may be represented by the following formula 2-1 or 2-2.
In formulas 2-1 and 2-2,
R 21 to R 26 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)An alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3-to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; or may be attached to one or more adjacent substituents to form one or more rings;
R 27 To R 29 Each independently represents and L 12 The site of attachment, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or one or more substituted or unsubstituted fused ring groups of a (C3-C30) aliphatic ring and one or more (C6-C30) aromatic ring; or may be attached to one or more adjacent substituents to form one or more rings; and is also provided with
T 1 、R 11 To R 20 、L 11 、L 12 And Ar is a group 11 Is as defined in formula 2'.
According to one embodiment of the present disclosure, the first host material and the second host material including the compound represented by formula 2' may be more specifically exemplified as the following compounds, but are not limited thereto.
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In the compounds H1-226 to H1-285 and H1-291 to H1-295, dn means that n number of hydrogen atoms are replaced with deuterium, and n is an integer from 1 to 30. Specifically, n is at least 1 and is an integer equal to the maximum number of hydrogen atoms in the compound.
According to one embodiment of the present disclosure, if the compound represented by formula 2' contains deuterium, the compound contains at least one deuterium, preferably R 11 To R 18 At least one of them contains deuterium, more preferably R 11 To R 18 and-L 11 -Ar 11 Deuterium containing; or R is 11 To R 18 and-L 12 -Ar A Containing at least one deuterium, still more preferably R 11 To R 18 Each of, -L 11 -Ar 11 and-L 12 -Ar A Contains at least one deuterium. According to one embodiment of the present disclosure, if the compound represented by formula 2 contains deuterium, the deuterium substitution rate is preferably 20% or more, more preferably 30% or more, still more preferably 40% or more, still more preferably 45% or more of the total number of hydrogen atoms. The compound having formula 2' substituted with the deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.
The compounds represented by formulas 1, 2 and 2' according to the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by formula 1 of the present disclosure may be prepared by referring to korean patent application laid-open No. 2021-0046437, etc., but is not limited thereto. The compounds represented by formulas 2 and 2' of the present disclosure may be prepared by referring to korean patent application laid-open No. 2010-0109060, chinese patent application laid-open No. 110294663, and the like, but are not limited thereto. The deuterium substituted compound among the compounds represented by formulas 1, 2 and 2' may be prepared by referring to korean patent application publication No. 2012-0101029, etc., in addition to the above-mentioned references, but is not limited thereto.
Although illustrative synthetic examples of the compounds represented by formulas 1, 2 and 2' are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartmash (Buchwald-Hartwig) cross-coupling reactions, N-arylation reactions, acidified montmorillonite (H-mont) -mediated etherification reactions, miyaura) boronation reactions, suzuki (Suzuki) cross-coupling reactions, intramolecular acid inductionGuided cyclization, pd (II) -catalyzed oxidative cyclization, grignard (Grignard Reaction), heck (Heck reaction), dehydrative cyclization, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and the above reaction proceeds even when substituents defined by formulas 1, 2, and 2' but not specified in specific synthesis examples are bonded.
Hereinafter, an organic electroluminescent device using a plurality of host materials as described above will be described.
According to one embodiment of the present disclosure, an organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer, wherein the light emitting layer may include a plurality of host materials including at least one first host material represented by formula 1 above and at least one second host material represented by formula 2 above, and wherein the first host material and the second host material are different from each other.
According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure comprises at least one compound selected from the group consisting of compounds C-1 to C-104 (which is a first host material) and at least one compound selected from the group consisting of compounds H1-1 to H1-295 and H2-1 to H2-115 (which is a second host material). The plurality of host materials may be contained in the same organic layer, such as a light-emitting layer, or may be contained in different light-emitting layers each.
According to another embodiment of the present disclosure, an organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer, wherein the light emitting layer may include a plurality of host materials including at least one first host material and at least one second host material represented by formula 2', wherein the first host material and the second host material are different from each other.
According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure includes at least one compound selected from the group consisting of compounds H1-1 to H1-295 as a first host material and a second host material, respectively, wherein the first host material and the second host material are different from each other. The plurality of host materials may be contained in the same organic layer, such as a light-emitting layer, or may be contained in different light-emitting layers each.
The organic layer may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. In addition to the luminescent materials of the present disclosure, the organic layer may further comprise an amine-based compound and/or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole assist layer, the light emitting assist layer, or the electron blocking layer may contain an amine-based compound (e.g., an arylamine-based compound, a styrylarylamine-based compound, or the like) as a hole injection material, a hole transport material, a hole assist material, a light emitting assist material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may contain azine-based compounds as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: group 1, group 2, group 4 transition metal, group 5 transition metal, lanthanide, and organometal of the d-transition element, or at least one complex compound comprising such a metal.
A variety of host materials according to the present disclosure may be used as a light emitting material for a white organic light emitting device. Various structures of a white organic light emitting device have been proposed, such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light emitting members, or a Color Conversion Material (CCM) method, or the like. Furthermore, a variety of host materials according to the present disclosure may also be used in organic electroluminescent devices comprising Quantum Dots (QDs).
One of the first electrode and the second electrode may be an anode, and the other may be a cathode. In this case, each of the first electrode and the second electrode may be formed of a transparent conductive material, or a transflective or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type according to the type of material forming the first and second electrodes.
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 so as to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayer. In addition, the hole injection layer may be doped with a p-type dopant. An electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and may block electrons from the light emitting layer from overflowing and confine excitons in the light emitting layer to prevent light leakage. The hole transporting layer or the electron blocking layer may be a multilayer, wherein a plurality of compounds may be used in each of the 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 multilayer in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein two compounds may be simultaneously used in each of the multilayer. The hole blocking layer is a layer located between the electron transport layer (or electron injection layer) and the light emitting layer, and prevents holes from reaching the cathode, thereby increasing the recombination probability of electrons and holes in the light emitting layer. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein a plurality of compounds may be used in each of the multilayer. In addition, the electron injection layer may be doped with an n-type dopant.
The light emitting auxiliary layer is a layer placed between the anode and the light emitting layer or between the cathode and the light emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to promote hole injection and/or 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 transport or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer to exhibit an effect of promoting or blocking a hole transport rate (or injection rate), thereby enabling control of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving efficiency and/or lifetime of the organic electroluminescent device.
In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer may be preferably placed on one or more inner surfaces of one or both electrodes. In particular, a chalcogenide (including oxide) layer of silicon or aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The surface layer may provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (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, mgF 2 、CaF 2 Rare earth metal fluorides, etc.; and the metal oxide includes Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
In the organic electroluminescent device of the present disclosure, it is preferable that a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant is disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus injection and transport of electrons from the mixing region to the electroluminescent medium becomes easier. Furthermore, the hole transporting compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the electroluminescent medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds; and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing 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.
According to an embodiment of the present disclosure, the organic electroluminescent device may further include at least one dopant in the light emitting layer.
The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and preferably is a fluorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but may be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably ortho-metallized complex compounds selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following formula D, but is not limited thereto.
In the formula D, the amino acid sequence of the formula,
R 101 to R 111 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L' 4 -N-(Ar' 4 )(Ar' 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to adjacent substituents to form one or more rings;
Y' 1 represents B;
X' 1 and X' 2 Each independently represents NR';
r ' each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or-L ' ' 4 -N-(Ar' 4 )(Ar' 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or can be connected to R 101 、R 108 、R 109 And R is 111 Forming one or more rings on at least one of the rings;
L' 4 each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar' 4 And Ar' 5 Each independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment of the present disclosure, R 101 To R 111 Can each independently be hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 20-membered) heteroaryl, or-L' 4 -N-(Ar' 4 )(Ar' 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to adjacent substituents to form one or more rings.
In another embodiment of the present disclosure, R 101 To R 111 May each independently be hydrogen, deuterium, unsubstituted (C1-C10) alkyl; unsubstituted or substituted by one or more (C1-C10) alkyl groups, one or more (13-to 18-membered) heteroaryl groups, and one or more di (C6-C18) arylamino groupsOne less substituted (C6-C18) aryl; (5-to 18-membered) heteroaryl, unsubstituted or substituted by one or more (C1-C10) alkyl groups; or-L' 4 -N-(Ar' 4 )(Ar' 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to adjacent substituents to form one or more rings. For example, R 101 To R 111 Each independently may be hydrogen, methyl, tert-butyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, triphenylene, carbazolyl, phenoxazinyl, phenothiazinyl, dimethylacridyl, dimethylxanthenyl, diphenylamino, phenylnaphthylamino, biphenylamino, phenylamino substituted by one or more phenylcarbazolyl or one or more dibenzofuranyl, or (17-to 21-membered) heteroaryl substituted by at least one of one or more methyl and one or more phenyl; or may be attached to adjacent substituents to form a benzene ring, an indole ring substituted with at least one of one or more phenyl groups and one or more diphenylamino groups, a benzofuran ring, a benzothiophene ring, or a 19-membered heterocyclic ring substituted with one or more methyl groups. The one or more substituents of the substituted phenyl group may be at least one of methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl, and dimethylacridyl.
According to one embodiment, the compound represented by the above formula D may be exemplified by the following compounds, but is not limited thereto.
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In the above compounds, D2 to D5 mean that two (2) to five (5) hydrogen atoms are replaced with deuterium.
Each layer of the organic electroluminescent device of the present disclosure may be formed by a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating, or the like, or a wet film forming method such as any one of spin coating, dip coating, flow coating, or the like. When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer is soluble or dispersible and which has no problem in terms of film forming ability.
Further, the first and second host materials according to one embodiment of the present disclosure may be formed into films by the methods listed above, typically by co-evaporation or hybrid evaporation. Co-evaporation is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and an electric current is applied to both chambers simultaneously to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in one crucible source before evaporation, and an electric current is applied to the cell to evaporate the materials.
When the first and second host compounds are present in the same layer or different layers in the organic electroluminescent device according to one embodiment of the present disclosure, the two host compounds may individually form a film, respectively. For example, the second host material may be evaporated after the first host material is evaporated.
The present disclosure may provide a display system including a plurality of host materials including a first host material represented by formula 1 and a second host material represented by formula 2; or a plurality of host materials including a first host material and a second host material represented by formula 2'. Further, a display system, for example, 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 organic electroluminescence device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, driving voltage, current efficiency, CIE color coordinates, and lifetime characteristics of the OLED according to the present disclosure will be explained. However, the following examples merely explain the characteristics of the OLED according to the present disclosure for a detailed understanding thereof, and the present disclosure is not limited to the following examples.
Examples of the apparatus 1-1 to 1-3, 2-1 to 2-3, 4-1 to 4-4, 5-1 to 5-3, 6-1 to 6-3, and 7-1 to 7-3: using
Production of OLEDs from a variety of host materials comprising specific combinations of compounds according to the present disclosure
An OLED according to the present disclosure was produced. A transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (gematec co., ltd., japan Ji Aoma limited)) on a glass substrate for OLED was sequentially ultrasonically washed with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI was introduced into one cell of the vacuum vapor deposition apparatus and compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates and compound HI was deposited at a doping level of 3wt% based on the total of compound HI and compound HT-1 to form a hole injection with a thickness of 10nmA layer. Subsequently, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby depositing a second hole transport layer having a thickness of 5nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: the compounds shown in tables 1, 2 and 4 to 7 below were introduced as a main body into two cells of a vacuum vapor deposition apparatus at a ratio of 1:1, and the compound BD was introduced as a dopant into the other cell. The dopant materials were simultaneously evaporated at different rates and the dopants were deposited in a doping amount of 2wt% based on the total amount of host and dopant to form a light emitting layer having a thickness of 20nm on the second hole transport layer. The compound EI-1 and the compound EI-2 were introduced into two other cells and evaporated at a rate of 1:1 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-2 was deposited as an electron injection layer having a thickness of 2nm, an Al cathode having a thickness of 80nm was deposited by using another vacuum vapor deposition apparatus, thereby producing an OLED. Each compound for each material was prepared by mixing at 10 a -6 Purification was performed by vacuum sublimation under the tray.
Comparative examples 1-1, 1-2, 2-1 to 2-3, 4-1 to 4-3, 5-1, 5-2, 6-1 to 6-3 and 7-1 to 7-3: production bag
OLED containing conventional compounds as unitary host materials
OLEDs were produced in the same manner as in device examples 1-1 to 1-3, 2-1 to 2-3, 4-1 to 4-4, 5-1 to 5-3, 6-1 to 6-3, and 7-1 to 7-3, except that only the compounds shown in tables 1, 2, and 4 to 7 below were used as the host materials of the light-emitting layers.
Device example 3-1: production using multiple host materials comprising specific combinations of compounds according to the present disclosure
OLED
An OLED was produced in the same manner as in device examples 1-1 to 1-3, 2-1 to 2-3, 4-1 to 4-4, 5-1 to 5-3, 6-1 to 6-3, and 7-1 to 7-3 except that the compounds shown in Table 3 below were used as host materials for the light-emitting layers to deposit the light-emitting layers, and Compound ET-1 was deposited as an electron buffer layer having a thickness of 5nm, followed by introducing Compound EI-1 and Compound EI-2 into two different cells and evaporating them at a ratio of 1:1 to deposit an electron transport layer having a thickness of 30nm on the light-emitting layers.
Comparative examples 3-1 and 3-2: production of OLED comprising conventional compounds as unitary host material
An OLED was produced in the same manner as in device example 3-1, except that only the compounds shown in table 3 below were used as the host material of the light-emitting layer.
The driving voltage, current efficiency (cd/a) and CIE color coordinates at a luminance of 1,000 nit and the shortest time it takes for the luminance to decrease from 100% to 95% at a luminance of 1,280 nit (lifetime: T95) of the OLEDs produced in the above device examples and comparative examples are provided in the following tables 1 to 7.
TABLE 1
TABLE 2
TABLE 3
TABLE 4
TABLE 5
TABLE 6
TABLE 7
From tables 1 to 7 above, it can be confirmed that the organic electroluminescent device including the specific combination of the compounds according to the present disclosure as a host material exhibits a lower driving voltage, higher current efficiency, and/or improved lifetime characteristics, particularly significantly improved lifetime characteristics, compared to the organic electroluminescent device including the conventional compound as a single host material.
The compounds used in the device examples and comparative examples are shown in table 8 below.
TABLE 8
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Claims (16)
1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2, and wherein the first host compound and the second host compound are different from each other:
In the formula (1) of the present invention,
L 1 and L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 and Ar is a group 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 1 to R 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-C7) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused rings, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted di (C1-C30) alkylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) arylsilyl, substituted or unsubstituted di (C6-C30) arylsilyl, substituted or unsubstituted amino Substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino; and is also provided with
a and b each independently represent an integer of 1 or 2, wherein each Ar, if a and b are 2 1 And each Ar 2 May be the same or different from each other;
in the formula (2) of the present invention,
Ar A represents the following formula A-1 or A-2:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
T 2 Represents CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
ring C represents a substituted or unsubstituted naphthalene ring;
R 11 to R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused ring, or an aromatic group L, or an unsubstituted fused ring 13 -N(Ar 13 )(Ar 14 )；
R 19 、R 20 And R is 31 To R 34 Each independently represents and L 12 The attached site or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkylA group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tri (C1-C30) alkylsilyl group, a substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L 13 -N(Ar 13 )(Ar 14 )；
R a And R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 to L 13 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
Ar 13 and Ar is a group 14 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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.
2. The plurality of host materials of claim 1, wherein Ar 1 And Ar is a group 2 Unsubstituted or substituted by deuterium and one or more (C6-C30) aryl groupsOne less substituted (C6-C30) aryl.
3. The plurality of host materials of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.
4. The plurality of host materials of claim 1, wherein Ar A Represented by any one of the following formulas b-1 to b-4:
in formulae b-1 to b-4,
R 21 to R 26 Each independently represents and L 12 The attached site or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic and one or more (C6-C30) fused ring or fused ring, substituted or fused ring L, or L 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
R 35 to R 42 Is as for R 31 To R 34 Defined as follows; and is also provided with
T 1 、T 2 、R 19 、R 20 And R is 31 To R 34 Is as defined in claim 1.
5. The plurality of host materials of claim 1, wherein formula 2 is represented by the following formula 2-1 or 2-2:
in formulas 2-1 and 2-2,
R 21 to R 26 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, one or more (C3-C30) aliphatic rings and one or more (C6-C30) fused ring, or an aromatic group L, or an unsubstituted fused ring 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
R 27 to R 29 Each independently represents and L 12 The attached site or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30 Aryl silyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L 13 -N(Ar 13 )(Ar 14 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings; and is also provided with
T 1 、R 11 To R 20 、L 11 To L 13 、Ar 11 、Ar 13 And Ar is a group 14 Is as defined in claim 1.
6. The plurality of host materials of claim 1, wherein formula 2 is represented by the following formula 3-1:
in the formula 3-1 of the present invention,
R 31 to R 38 And R is 40 Is as for R 11 To R 18 Defined as follows; and is also provided with
T 2 、R 11 To R 18 、L 11 、L 12 And Ar is a group 11 Is as defined in claim 1.
7. The plurality of host materials of claim 1, wherein at least one of formulas 1 and 2 comprises deuterium.
8. The plurality of host materials of claim 1, wherein the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkylyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring groups of the one or more aliphatic and one or more aromatic rings, the substituted mono-or di-alkylamino, the substituted mono-or di-alkenylamino, the substituted mono-or di-arylamino, the substituted mono-or di-heteroarylamino, the substituted alkylarylamino, the substituted alkylheteroarylamino, the substituted alkenylheteroarylamino, the substituted heteroarylamino, the substituted heteroaryl, the substituted aromatic and the substituted aromatic ring, each of which is independently selected from the group consisting of at least one of the following, the substituted aromatic rings, and the substituted aromatic ring, and the one or more groups thereof: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (C1-C30) alkyl unsubstituted or substituted by deuterium; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; a (3-to 30-membered) heteroaryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups; (C6-C30) aryl unsubstituted or substituted with at least one of deuterium, one or more (C1-C30) alkyl groups, one or more (C6-C30) aryl groups and one or more (3-to 30-membered) heteroaryl groups; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylborocarbonyl; (C6-C30) arylphosphines; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
9. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
wherein Dn means that n number of hydrogen atoms are replaced by deuterium, and
n is an integer from 1 to 34.
10. The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
wherein Dn means that n number of hydrogen atoms are replaced by deuterium, and
n is an integer from 1 to 30.
11. The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
/>
/>
wherein Dn means that n number of hydrogen atoms are replaced by deuterium, and
n is an integer from 1 to 33.
12. An organic electroluminescent device, comprising: an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises the plurality of host materials according to claim 1.
13. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound and the second host compound are represented by the following formula 2', and wherein the first host compound and the second host compound are different from each other:
In the formula 2' of the present invention,
Ar A represents the following formula A-1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
T 1 representation O, S, or CR a R b ；
Ring a and ring B each independently represent a substituted or unsubstituted (C6-C30) aromatic hydrocarbon ring, or a substituted or unsubstituted (3-to 30-membered) heteroaromatic hydrocarbon ring;
R 11 to R 18 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more (C6-C30) fused ring-substituted or unsubstituted aromatic groups;
R 19 and R is 20 Each independently represents and L 12 The attached site, or represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more fused ring-C6-C30 aromatic groups;
R a And R is b Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be connected to each other to form one or more rings;
L 11 and L 12 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 11 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
14. The plurality of host materials of claim 13, wherein formula 2' is represented by the following formula 2-1 or 2-2:
in formulas 2-1 and 2-2,
R 21 to R 26 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-to 7-membered) heterocycloalkyl, 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, or one or more (C3-C30) aliphatic and one or more (C6-C30) fused ring-substituted or unsubstituted aromatic groups; or may be attached to one or more adjacent substituents to form one or more rings;
R 27 To R 29 Each independently represents and L 12 The attached site or 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 unsubstitutedA substituted or unsubstituted fused ring group of an unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, or one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; or may be attached to one or more adjacent substituents to form one or more rings; and is also provided with
T 1 、R 11 To R 20 、L 11 、L 12 And Ar is a group 11 Is as defined in claim 13.
15. The plurality of host materials of claim 13, wherein the compound represented by formula 2' is at least one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
wherein Dn means that n number of hydrogen atoms are replaced by deuterium, and
n is an integer from 1 to 30.
16. An organic electroluminescent device, comprising: an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of host materials according to claim 13.
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| KR20220178324 | 2022-12-19 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117886786A (en) * | 2024-03-12 | 2024-04-16 | 浙江华显光电科技有限公司 | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117886786A (en) * | 2024-03-12 | 2024-04-16 | 浙江华显光电科技有限公司 | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device |
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