WO2019022512A1 - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents
A plurality of host materials and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- WO2019022512A1 WO2019022512A1 PCT/KR2018/008434 KR2018008434W WO2019022512A1 WO 2019022512 A1 WO2019022512 A1 WO 2019022512A1 KR 2018008434 W KR2018008434 W KR 2018008434W WO 2019022512 A1 WO2019022512 A1 WO 2019022512A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- membered
- aryl
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 117
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- -1 benzoimidazolyl Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000005104 aryl silyl group Chemical group 0.000 claims description 36
- 239000002019 doping agent Substances 0.000 claims description 35
- 125000001769 aryl amino group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 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
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 150
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- 238000007740 vapor deposition Methods 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 230000000903 blocking effect Effects 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 101000843236 Homo sapiens Testis-specific H1 histone Proteins 0.000 description 8
- 102100031010 Testis-specific H1 histone Human genes 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- GLYYLMBVQZMMMS-UHFFFAOYSA-N 12h-[1]benzothiolo[3,2-a]carbazole Chemical class S1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 GLYYLMBVQZMMMS-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000001704 evaporation Methods 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
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 2
- DERKMBVPWKXOHM-UHFFFAOYSA-N 12h-[1]benzofuro[3,2-a]carbazole Chemical compound O1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 DERKMBVPWKXOHM-UHFFFAOYSA-N 0.000 description 2
- AYJJTPLDSZAGGA-UHFFFAOYSA-N 2-ethyl-7-methyl-5-(4-methylphenyl)-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine Chemical class C1N(CC)CCC2C1C1=CC=C(C)C=C1C2C1=CC=C(C)C=C1 AYJJTPLDSZAGGA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ANSIWEGOCFWRSC-UHFFFAOYSA-N 1,2-dimethyl-1h-indene Chemical group C1=CC=C2C(C)C(C)=CC2=C1 ANSIWEGOCFWRSC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 11h-indeno[1,2-h]quinoline Chemical class C1=CC=NC2=C3CC4=CC=CC=C4C3=CC=C21 ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical group N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- ALIHHRJMNTXXJT-UHFFFAOYSA-N 2-phenyl-1h-benzo[g]indole Chemical group N1C(C2=CC=CC=C2C=C2)=C2C=C1C1=CC=CC=C1 ALIHHRJMNTXXJT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- WCXNEXQHQNXXEA-UHFFFAOYSA-N 4,6-bis(3,5-dipyridin-4-ylphenyl)-2-methylpyrimidine Chemical compound N=1C(C)=NC(C=2C=C(C=C(C=2)C=2C=CN=CC=2)C=2C=CN=CC=2)=CC=1C(C=1)=CC(C=2C=CN=CC=2)=CC=1C1=CC=NC=C1 WCXNEXQHQNXXEA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XDNADZYPWVQFRI-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinoline Chemical class C1=CC=NC2=C3C4=CC=CC=C4OC3=CC=C21 XDNADZYPWVQFRI-UHFFFAOYSA-N 0.000 description 1
- CWDFYKZZCSEOPO-UHFFFAOYSA-N [1]benzothiolo[2,3-h]quinoline Chemical class C1=CC=NC2=C3C4=CC=CC=C4SC3=CC=C21 CWDFYKZZCSEOPO-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- LJOLGGXHRVADAA-UHFFFAOYSA-N benzo[e][1]benzothiole Chemical group C1=CC=C2C(C=CS3)=C3C=CC2=C1 LJOLGGXHRVADAA-UHFFFAOYSA-N 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-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
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 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
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000007704 transition Effects 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- the present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
- An electroluminescent device is a self-light-emitting device which has advantages in that it provides a wide viewing angle, a great contrast ratio, and a fast response time.
- the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- An organic electroluminescent device is a device changing electrical energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode.
- the organic layer of an organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
- the materials used for the organic layer are categorized by their functions in a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (including host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
- a hole injection material a hole transport material
- a hole auxiliary material a hole auxiliary material
- a light-emitting auxiliary material an electron blocking material
- a light-emitting material including host and dopant materials
- an electron buffer material a hole blocking material
- an electron transport material including host and dopant materials
- a light-emitting material must have high quantum efficiency, high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable.
- Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, and additionally yellow or orange light-emitting materials.
- light-emitting materials can also be categorized into host and dopant materials according to their functions.
- the host material which acts as a solvent in a solid state and transfers energy, needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve long lifespan, ease of forming an amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
- a light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability.
- a device having excellent EL characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system as a light-emitting material, their selection is important.
- Korean Patent Application Laying-Open No. 2011-0066766 discloses an organic EL device using a benzothienocarbazole derivative fused with a benzene ring as a host material. Further, Korean Patent Application Laying-Open No. 2016-0149994 discloses an organic EL device using a compound, in which an arylamine is bonded directly or via a linker to a carbazole, as a host material.
- references do not specifically disclose an organic EL device using a compound, in which an arylamine is bonded directly or via a linker to a carbazole, and a benzothieno carbazole, benzofurano carbazole, indolocarbazole, or indenocarbazole derivative fused with a benzene ring, as a plurality of host materials.
- the organic EL devices disclosed in said references still need to be improved in terms of driving voltage, current efficiency, and operational lifespan.
- the objective of the present disclosure is to provide an organic electroluminescent device having long lifespan, while maintaining low driving voltage and/or high luminous efficiency.
- the present inventors found that the objective above 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 is represented by the following formula 1, and the second host compound is represented by the following formula 2:
- Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar 1 and Ar 2 , and Ar 3 and Ar 4 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;
- L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryl(ene);
- L 2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
- Ar 1 or Ar 2 represents a substituted or unsubstituted (C6-C30)aryl
- L 1 represents a substituted or unsubstituted (C6-C30)arylene
- Ar 1 or Ar 2 and L 1 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
- Ar 3 or Ar 4 represents a substituted or unsubstituted (C6-C30)aryl
- L 2 represents a substituted or unsubstituted (C6-C30)arylene
- Ar 3 or Ar 4 and L 2 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
- R 1 and R 2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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-C
- n and n each independently represent an integer of 0 to 2, with a proviso that at least one of m and n is 1 or more;
- each of R 1 and R 2 may be the same or different;
- X represents -NR 11 -, -CR 12 R 13 -, -O-, or -S-;
- HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl
- L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
- R 11 to R 13 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
- R 3 to R 5 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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-C
- a, b, and c each independently represent an integer of 1 to 4, in which if a, b, and c represent an integer of 2 or more, each of R 3 , R 4 , and R 5 may be the same or different.
- an organic electroluminescent device having long lifespan while maintaining low driving voltage and/or high luminous efficiency is provided, and a display device or a lighting device using the organic electroluminescent device can be manufactured.
- Figure 1 illustrates current efficiency versus luminance of organic electroluminescent devices produced in Comparative Example 1 and Device Example 2.
- organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
- organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
- the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
- the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (a host material or a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
- a plurality of organic electroluminescent materials in the present disclosure means an organic electroluminescent material as a combination of at least two compounds, which may be comprised in any layer constituting an organic electroluminescent device. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition).
- a plurality of organic electroluminescent materials may be a combination of at least two compounds which may be comprised in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
- At least two compounds may be comprised in the same layer or different layers, and may be mixture-evaporated or co-evaporated, or may be individually evaporated.
- a plurality of host materials in the present disclosure means an organic electroluminescent material as a combination of at least two host materials. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition).
- a plurality of host materials of the present disclosure may be comprised in any light-emitting layer constituting an organic electroluminescent device. At least two compounds comprised in a plurality of host materials may be comprised together in one light-emitting layer or may respectively be comprised in different light-emitting layers. If at least two host materials are comprised in one layer, for example, they may be mixture-evaporated to form a layer, or may be separately co-evaporated at the same time to form a layer.
- the combination of said two compounds may be used as a host material of a light-emitting layer to provide an organic electroluminescent device having high efficiency and long lifespan together with low driving voltage.
- N ext external quantum efficiency of an organic electroluminescent device means the number of photons emitted outside compared to the number of charges injected, and the definition is as follows:
- N ext is the external quantum efficiency
- N int is the internal quantum efficiency
- N out is the emission rate outside the device to the internally produced light.
- ⁇ is the combining rate of holes and electrons
- N ex is a producing rate of the excitons
- ⁇ p is the PL quantum efficiency.
- the carbazole group material fused with a hetero group, etc. used as the second host is used alone in a light-emitting layer, a charge-balance factor corresponding to ⁇ may be reduced due to relatively fast electron current characteristic.
- the insufficient hole current characteristic is compensated by an appropriate charge balance through the first host compound and the factor corresponding to ⁇ is improved, which may contribute to an enhancement of the organic electroluminescent device performance.
- the interfacial characteristic is improved by releasing the excitons extremely formed between the hole transport layer and the light-emitting layer to the light emitting layer/electron transport zone’s side.
- the compound of formula 1 can be represented by formula 1-1 or 1-2:
- Ar 11 to Ar 13 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar 11 and Ar 12 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;
- L 11 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
- Ar 11 or Ar 12 represents a substituted or unsubstituted (C6-C30)aryl
- L 11 represents a substituted or unsubstituted (C6-C30)arylene
- Ar 11 or Ar 12 and L 11 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
- X 1 represents NR 31 , O, S, or CR 32 R 33 ;
- R 31 to R 33 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
- R 21 to R 26 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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-C
- r 1 or 2.
- Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar 1 and Ar 2 , and Ar 3 and Ar 4 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring.
- Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C25)aryl.
- Ar 1 to Ar 4 each independently represent a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, or a tri(C6-C12)arylsilyl.
- Ar 1 to Ar 4 may each independently represent phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenanthrenylphenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbezofluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophenyl, phenyl substituted with triphenylsilyl, etc.
- L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryl(ene) (if n is 0, L 1 is an aryl, and if n is 1 or more, L 1 is an arylene). In one embodiment of the present disclosure, L 1 represents a substituted or unsubstituted (C6-C25)aryl(ene). In another embodiment of the present disclosure, L 1 represents a (C6-C25)aryl(ene) unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, or a tri(C6-C12)arylsilyl.
- L 1 may represent phenyl(ene), naphthyl(ene), biphenyl(ene), terphenyl(ene), naphthylphenyl(ene), phenylnaphthyl(ene), dimethylfluorenyl(ene), diphenylfluorenyl(ene), phenyl(ene) substituted with dibenzofuranyl, phenyl(ene) substituted with dibenzothiophenyl, phenyl(ene) substituted with triphenylsilyl, etc.
- L 2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene. In one embodiment of the present disclosure, L 2 represents a substituted or unsubstituted (C6-C20)arylene. In another embodiment of the present disclosure, L 2 represents an unsubstituted (C6-C20)arylene. Specifically, L 2 may represent phenylene, biphenylene, terphenylene, etc.
- Ar 1 or Ar 2 represents a substituted or unsubstituted (C6-C30)aryl
- L 1 represents a substituted or unsubstituted (C6-C30)arylene
- Ar 1 or Ar 2 and L 1 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring.
- Ar 1 or Ar 2 and L 1 may be linked via a single bond to form a carbazole ring.
- Ar 3 or Ar 4 represents a substituted or unsubstituted (C6-C30)aryl
- L 2 represents a substituted or unsubstituted (C6-C30)arylene
- Ar 3 or Ar 4 and L 2 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring.
- Ar 3 or Ar 4 and L 2 may be linked via a single bond to form a carbazole ring.
- R 1 and R 2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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
- R 1 and R 2 each independently represent hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic (5- to 15-membered) ring.
- R 1 and R 2 each independently represent hydrogen, an unsubstituted (C6-C12)aryl, or an unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a mono- or polycyclic (5- to 15-membered) ring unsubstituted or substituted with a (C1-C6)alkyl or an (C6-C12)aryl.
- R 1 and R 2 may each independently represent hydrogen, phenyl, dibenzofuranyl, dibenzothiophenyl, etc.; or may be linked to an adjacent substituent to form a benzene ring, a dimethylindene ring, a benzofuran ring, a benzothiophene ring, a naphthothiophene ring, a phenylindole ring, or a phenylbenzindole ring.
- n and n each independently represent an integer of 0 to 2, with a proviso that at least one of m and n is 1 or more. In one embodiment of the present disclosure, if m is 0, n is 1 or 2, and if m is 1, n is 0.
- p and q each independently represent an integer of 1 to 4, in which if p and q represent an integer of 2 or more, each of R 1 and R 2 may be the same or different.
- X represents -NR 11 -, -CR 12 R 13 -, -O-, or -S-.
- HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl. In one embodiment of the present disclosure, HAr represents a substituted or unsubstituted, nitrogen-containing (3- to 30-membered)heteroaryl. In another embodiment of the present disclosure, HAr represents a substituted or unsubstituted, nitrogen-containing (5- to 20-membered)heteroaryl.
- HAr represents a nitrogen-containing (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, or (C6-C12)aryl(5- to 15- membered)heteroaryl.
- HAr represents a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted benzoimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indo
- L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene.
- L represents a single bond, or a substituted or unsubstituted (C6-C12)arylene.
- L represents a single bond, or an unsubstituted (C6-C12)arylene.
- L may represent a single bond, phenylene, or naphthylene.
- R 11 to R 13 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
- R 11 represents a substituted or unsubstituted (C6-C12)aryl
- R 12 and R 13 each independently represent a substituted or unsubstituted (C1-C6)alkyl.
- R 11 represents an unsubstituted (C6-C12)aryl
- R 12 and R 13 each independently represent an unsubstituted (C1-C6)alkyl
- R 11 may represent phenyl
- R 12 and R 13 may each independently represent methyl
- R 3 to R 5 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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
- a, b, and c each independently represent an integer of 1 to 4, in which if a, b, and c represent an integer of 2 or more, each of R 3 , R 4 , and R 5 may be the same or different.
- the ring may be a mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in which the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- the heteroaryl(ene) may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P.
- the heteroatom may be substituted with at least one substituent selected from the group consisting of deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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,
- (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- (C3-C30)cycloalkyl is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (C6-C30)aryl(ene) is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 25, and more preferably 6 to 20, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, phenanthrenylphenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- (3- to 30-membered)heteroaryl(ene) is meant to be an aryl group having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
- the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond.
- the above heteroaryl may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, naphthothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazo
- Nitrogen-containing (5- to 30-membered)heteroaryl is meant to be an aryl group having 5 to 30 ring backbone atoms, including at least one heteroatom of N, in which the number of the ring backbone atoms is preferably 5 to 20, and more preferably 5 to 15, and the number of heteroatoms is preferably 1 to 4.
- the above nitrogen-containing heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond.
- the above nitrogen-containing heteroaryl may include a monocyclic ring-type heteroaryl such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridinyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, benzoquinazoliny
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
- said substituent may be methyl, phenyl, biphenyl, phenanthrenyl, naphthylphenyl, methylphenyl, dimethylfluorenyl, triphenylsilyl, dibenzofuranyl, dibenzothiophenyl, or phenylcarbazolyl.
- the compound represented by formula 1 includes the following compounds, but is not limited thereto:
- the compound represented by formula 2 includes the following compounds, but is not limited thereto:
- the compounds represented by formulas 1 and 2 according to the present disclosure can be prepared by a synthetic method known to a person skilled in the art.
- the compound represented by formula 1 can be prepared by referring to Korean Patent Application Laying-Open Nos. 2013-0106255 (published on September 27, 2013), 2014-0108637 (published on September 12, 2014), 2014-0068883 (published on June 9, 2014), etc.
- the compound represented by formula 2 can be prepared by referring to Korean Patent Application Laying-Open No. 2015-0032447 (published on March 26, 2015), etc., but is not limited thereto.
- the present disclosure provides a mixture comprising a combination of the compound represented by formula 1 and the compound represented by formula 2.
- the mixture may be used as an organic electroluminescent material.
- the organic electroluminescent device comprises an anode, a cathode, and at least one organic layer between the anode and the cathode.
- the organic layer may comprise a plurality of organic electroluminescent materials in which the compound represented by formula 1 is included as a first organic electroluminescent material, and the compound represented by formula 2 is included as a second organic electroluminescent material.
- the organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, in which the light-emitting layer may comprise the compound represented by formula 1 and the compound represented by formula 2.
- the organic electroluminescent device comprises an anode, a cathode, and at least one organic layer between the anode and the cathode, in which the organic layer comprises a light-emitting layer.
- the light-emitting layer comprises a host and a phosphorescent dopant.
- the host comprises a plurality of host materials, in which at least a first host compound of the plural host materials is represented by formula 1, and a second host compound is represented by formula 2.
- the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer of which two or more layers are stacked.
- the first and second host materials may both be comprised in one layer or may be respectively comprised in different light-emitting layers.
- the doping concentration of the dopant compound with respect to the host compound is less than 20 wt%.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, a hole blocking layer, and an electron blocking layer.
- the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1.
- the weight ratio is preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to 60:40, and still more preferably about 50:50.
- the dopant comprised in the organic electroluminescent device according to the present disclosure may be at least one fluorescent or phosphorescent dopant, and preferably at least one phosphorescent dopant.
- the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
- the dopant comprised in the organic electroluminescent device according to the present disclosure may include the compound represented by the following formula 101, but is not limited thereto.
- L is selected from the following structures:
- R 100 to R 103 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (C3-C30)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R 100 to R 103 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsub
- R 104 to R 107 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R 104 to R 107 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or
- R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or adjacent substituents of R 201 to R 211 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring; and
- n an integer of 1 to 3.
- the dopant material includes the following compounds, but is not limited thereto:
- the organic electroluminescent device according to the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
- the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
- a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer is preferably placed on an inner surface(s) of at least one of a pair of electrodes.
- a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a hole injection layer Between the anode and the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used. Multiple hole injection layers can be used in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds can be simultaneously used in each layer.
- the hole transport layer or the electron blocking layer can also be formed of multi-layers.
- an electron buffer layer Between the light-emitting layer and the cathode, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used.
- Multiple electron buffer layers can be used in order to control the injection of the electrons and enhance the interfacial characteristics between the light-emitting layer and the electron injection layer.
- Two compounds can be simultaneously used in each layer.
- the hole blocking layer or the electron transport layer can also be formed of multi-layers, and each layer can comprise two or more compounds.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge-generating layer to produce an electroluminescent device having two or more light-emitting layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
- a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
- first and the second host compounds of the present disclosure may be film-formed in the above-listed methods, commonly by a co-evaporation process or a mixture-evaporation process.
- the co-evaporation is a mixed deposition method in which two or more materials are placed in a respective individual crucible source and a current is applied to both cells at the same time to evaporate the materials.
- the mixture-evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporating them, and a current is applied to the cell to evaporate the materials.
- a display system or a lighting system can be produced.
- An OLED not according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -7 torr.
- ITO indium tin oxide
- Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
- a light-emitting layer was then deposited as follows.
- Compound H2-1 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-39 as a dopant was introduced into another cell of the apparatus.
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- compound ET-1 and compound EI-1 were evaporated in a weight ratio of 50:50 as electron transport materials to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- All the materials used for producing the OLED were purified by vacuum sublimation at 10 -6 torr.
- OLEDs were produced in the same manner as in Comparative Example 1, except that the first and second host compounds shown in Table 1 below as hosts were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited at a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- the first and second host compounds shown in Table 1 below as hosts were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited at a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm
- the driving voltage, luminous efficiency, light-emitting color, and the time taken for luminance to decrease from 100% to 95% at a luminance of 5,000 nit (lifespan; T95) of the OLEDs produced in Comparative Example 1 and Device Examples 1 to 5 are provided in Table 1 below.
- Figure 1 illustrates current efficiency versus luminance of the OLEDs produced in Comparative Example 1 and Device Example 2.
- the plurality of host materials of the present disclosure may be used to improve luminous efficiency and lifespan characteristic, while maintaining the driving voltage at a similar level or reducing the driving voltage.
- the combination of the host materials significantly improves roll-off compared to the comparative example using a single host material.
- HOD Hole Only Device
- EOD Electron Only Device
- An ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
- Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -7 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 10 nm on the ITO substrate.
- Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the hole injection layer.
- compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 10 nm on the first hole transport layer.
- a light-emitting layer was formed thereon as follows: Compound H2-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the second hole transport layer.
- Compound HT-1 was then introduced into one cell of the vacuum vapor deposition apparatus and evaporated to form an electron blocking layer having a thickness of 20 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron blocking layer by another vacuum vapor deposition apparatus.
- an OLED was produced.
- HOD was produced in the same manner, except that, in the case of a mixture of a first host compound and a second host compound, the first host compound (H1-7) and the second host compound (H2-1) were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited at a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm. Voltages at the current density of 10 mA/cm 2 and 100 mA/cm 2 are shown in Table 2 below.
- B4PyMPM 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the hole blocking layer.
- Compound ET-1 and lithium quinolate were introduced into one cell and another cell of the vacuum vapor deposition apparatus, respectively, and the two materials were evaporated at the same rate and doped in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
- All the materials used for producing the OLED were purified by vacuum sublimation at 10 -6 torr.
- EOD was produced in the same manner, except that, in the case of a mixture of a first host compound and a second host compound, the first host compound ( H1-7 ) and the second host compound ( H2-1 ) were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited in a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm. Voltages at the current density of 10 mA/cm 2 and 100 mA/cm 2 are shown in Table 3 below.
- the device comprising a light-emitting layer of only compound H2-1 showed relatively high driving voltage characteristic compared to the device comprising the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound), and thus it shows a hole injection blocking characteristic. Meanwhile, it is confirmed that the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound) showed significantly improved hole current chatacteristic due to compound H1-7 (the first host compound).
- the device comprising a light-emitting layer of only compound H2-1 showed relatively low driving voltage characteristic compared to the device comprising the combination of Compound H1-7 (the first host compound) and compound H2-1 (the second host compound). Meanwhile, it is confirmed that the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound) showed slightly reduced electron current chatacteristic due to compound H1-7 (the first host compound). As a result, the combination of the first host compound and the second host compound according to the present disclosure showed relatively good charge balance characteristic by relatively improving hole current characteristic and slightly reducing electron current characteristic.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to a plurality of host materials comprising a compound represented by formula 1 and a compound represented by formula 2, and an organic electroluminescent device comprising the same. The organic electroluminescent device according to the present disclosure can exhibit excellent lifespan characteristic, while maintaining low driving voltage and high luminous efficiency, by comprising a plurality of host compounds in a specific combination.
Description
The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
An electroluminescent device (EL device) is a self-light-emitting device which has advantages in that it provides a wide viewing angle, a great contrast ratio, and a fast response time. The first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
An organic electroluminescent device (OLED) is a device changing electrical energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of an organic EL device may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used for the organic layer are categorized by their functions in a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (including host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. In the organic EL device, due to an application of a voltage, holes are injected from the anode to the light-emitting layer, electrons are injected from the cathode to the light-emitting layer, and excitons of high energies are formed by a recombination of the holes and the electrons. By this energy, organic luminescent compounds reach an excited state, and light emission occurs by emitting light from energy due to the excited state of the organic luminescent compounds returning to a ground state.
The most important factor determining luminous efficiency in an organic EL device is light-emitting materials. A light-emitting material must have high quantum efficiency, high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable. Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, and additionally yellow or orange light-emitting materials. In addition, light-emitting materials can also be categorized into host and dopant materials according to their functions. Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, materials showing better characteristics than conventional ones must be urgently developed. The host material, which acts as a solvent in a solid state and transfers energy, needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve long lifespan, ease of forming an amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
A light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability. Generally, a device having excellent EL characteristics has a structure comprising a light-emitting layer formed by doping a dopant to a host. Since host materials greatly influence the efficiency and lifespan of the EL device when using a dopant/host material system as a light-emitting material, their selection is important.
Korean Patent Application Laying-Open No. 2011-0066766 discloses an organic EL device using a benzothienocarbazole derivative fused with a benzene ring as a host material. Further, Korean Patent Application Laying-Open No. 2016-0149994 discloses an organic EL device using a compound, in which an arylamine is bonded directly or via a linker to a carbazole, as a host material. However, said references do not specifically disclose an organic EL device using a compound, in which an arylamine is bonded directly or via a linker to a carbazole, and a benzothieno carbazole, benzofurano carbazole, indolocarbazole, or indenocarbazole derivative fused with a benzene ring, as a plurality of host materials. In addition, the organic EL devices disclosed in said references still need to be improved in terms of driving voltage, current efficiency, and operational lifespan.
The objective of the present disclosure is to provide an organic electroluminescent device having long lifespan, while maintaining low driving voltage and/or high luminous efficiency.
As a result of intensive studies, the present inventors found that the objective above 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 is represented by the following formula 1, and the second host compound is represented by the following formula 2:
wherein
Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar1 and Ar2, and Ar3 and Ar4 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;
L1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryl(ene);
L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
if Ar1 or Ar2 represents a substituted or unsubstituted (C6-C30)aryl, and L1 represents a substituted or unsubstituted (C6-C30)arylene, Ar1 or Ar2 and L1 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
if Ar3 or Ar4 represents a substituted or unsubstituted (C6-C30)aryl, and L2 represents a substituted or unsubstituted (C6-C30)arylene, Ar3 or Ar4 and L2 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
R1 and R2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring;
m and n each independently represent an integer of 0 to 2, with a proviso that at least one of m and n is 1 or more; and
p and q each independently represent an integer of 1 to 4, in which if p and q represent an integer of 2 or more, each of R1 and R2 may be the same or different;
wherein
X represents -NR11-, -CR12R13-, -O-, or -S-;
HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;
L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
R11 to R13 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R3 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring; and
a, b, and c each independently represent an integer of 1 to 4, in which if a, b, and c represent an integer of 2 or more, each of R3, R4, and R5 may be the same or different.
According to the present disclosure, an organic electroluminescent device having long lifespan while maintaining low driving voltage and/or high luminous efficiency is provided, and a display device or a lighting device using the organic electroluminescent device can be manufactured.
Figure 1 illustrates current efficiency versus luminance of organic electroluminescent devices produced in Comparative Example 1 and Device Example 2.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The term "organic electroluminescent compound" in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. The organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (a host material or a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
The term "a plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material as a combination of at least two compounds, which may be comprised in any layer constituting an organic electroluminescent device. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds which may be comprised in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be comprised in the same layer or different layers, and may be mixture-evaporated or co-evaporated, or may be individually evaporated.
The term "a plurality of host materials" in the present disclosure means an organic electroluminescent material as a combination of at least two host materials. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition). A plurality of host materials of the present disclosure may be comprised in any light-emitting layer constituting an organic electroluminescent device. At least two compounds comprised in a plurality of host materials may be comprised together in one light-emitting layer or may respectively be comprised in different light-emitting layers. If at least two host materials are comprised in one layer, for example, they may be mixture-evaporated to form a layer, or may be separately co-evaporated at the same time to form a layer.
The benzothieno carbazole, benzofurano carbazole, indolocarbazole, or indenocarbazole derivative fused with a benzene ring, which corresponds to formula 2, inherently has high electronegativity and an electron-enriched group, and is rigid as a fused structure, and thus intermolecular transition is easy. In addition, if the intermolecular stacking is enhanced, the horizontal molecular orientation is more easily achieved, thereby realizing fast current characteristic. Thus, using the limited structures of triazine, quinazoline, quinoxaline, pyrimidine derivatives, etc., as host materials, light-emitting devices having a relatively low driving voltage, excellent luminous efficiency such as current efficiency and power efficiency, and capable of realizing high color purity have been provided. However, since said compounds have relatively strong electron current characteristic, excitons generated in an organic electroluminescent device are extremely formed between a hole transport layer and a light-emitting layer, resulting in exciton quenching or triplet-polaron quenching. Thus, improvement of efficiency and lifespan still has been required.
To solve the above problems, the compound represented by formula 1, in which carbazole or fused carbazole is substituted with an amine having strong hole current characteristic, is used as a first host, and the fused cabazole group material having strong electron current characteristic is used as a second host. The combination of said two compounds may be used as a host material of a light-emitting layer to provide an organic electroluminescent device having high efficiency and long lifespan together with low driving voltage.
Generally, external quantum efficiency (Next) of an organic electroluminescent device means the number of photons emitted outside compared to the number of charges injected, and the definition is as follows:
Herein, Next is the external quantum efficiency, Nint is the internal quantum efficiency, and Nout is the emission rate outside the device to the internally produced light. In addition, γ is the combining rate of holes and electrons, Nex is a producing rate of the excitons, and Øp is the PL quantum efficiency.
If the carbazole group material fused with a hetero group, etc. used as the second host is used alone in a light-emitting layer, a charge-balance factor corresponding to γ may be reduced due to relatively fast electron current characteristic. However, in the combination of organic electroluminescent compounds according to the present disclosure, the insufficient hole current characteristic is compensated by an appropriate charge balance through the first host compound and the factor corresponding to γ is improved, which may contribute to an enhancement of the organic electroluminescent device performance. Further, the interfacial characteristic is improved by releasing the excitons extremely formed between the hole transport layer and the light-emitting layer to the light emitting layer/electron transport zone’s side. Thus, an organic electroluminescent device of a relatively low driving voltage, excellent luminous efficiency such as current efficiency and power efficiency, and capable of realizing high color purity may be provided.
Hereinafter, a plurality of host materials comprising the organic electroluminescent compounds represented by formulas 1 and 2 will be described in more detail.
The compound of formula 1 can be represented by formula 1-1 or 1-2:
wherein
Ar11 to Ar13 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar11 and Ar12 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;
L11 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
if Ar11 or Ar12 represents a substituted or unsubstituted (C6-C30)aryl, and L11 represents a substituted or unsubstituted (C6-C30)arylene, Ar11 or Ar12 and L11 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;
at least one of a and b, b and c, c and d, e and f, f and g, or g and h in formulas 1-1 and 1-2 and two * positions of the following formula 1-a, 1-b, or 1-c may be fused to form a ring:
X1 represents NR31, O, S, or CR32R33;
R31 to R33 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R21 to R26 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; and
r represents 1 or 2.
In formula 1, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar1 and Ar2, and Ar3 and Ar4 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring. In an embodiment of the present disclosure, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C25)aryl. In another embodiment of the present disclosure, Ar1 to Ar4 each independently represent a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, or a tri(C6-C12)arylsilyl. Specifically, Ar1 to Ar4 may each independently represent phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenanthrenylphenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbezofluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophenyl, phenyl substituted with triphenylsilyl, etc.
In formula 1, L1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryl(ene) (if n is 0, L1 is an aryl, and if n is 1 or more, L1 is an arylene). In one embodiment of the present disclosure, L1 represents a substituted or unsubstituted (C6-C25)aryl(ene). In another embodiment of the present disclosure, L1 represents a (C6-C25)aryl(ene) unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, or a tri(C6-C12)arylsilyl. Specifically, L1 may represent phenyl(ene), naphthyl(ene), biphenyl(ene), terphenyl(ene), naphthylphenyl(ene), phenylnaphthyl(ene), dimethylfluorenyl(ene), diphenylfluorenyl(ene), phenyl(ene) substituted with dibenzofuranyl, phenyl(ene) substituted with dibenzothiophenyl, phenyl(ene) substituted with triphenylsilyl, etc.
In formula 1, L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene. In one embodiment of the present disclosure, L2 represents a substituted or unsubstituted (C6-C20)arylene. In another embodiment of the present disclosure, L2 represents an unsubstituted (C6-C20)arylene. Specifically, L2 may represent phenylene, biphenylene, terphenylene, etc.
In formula 1, if Ar1 or Ar2 represents a substituted or unsubstituted (C6-C30)aryl, and L1 represents a substituted or unsubstituted (C6-C30)arylene, Ar1 or Ar2 and L1 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring. In one embodiment of the present disclosure, if Ar1 or Ar2 represents a phenyl and L1 represents a phenylene, Ar1 or Ar2 and L1 may be linked via a single bond to form a carbazole ring.
In formula 1, if Ar3 or Ar4 represents a substituted or unsubstituted (C6-C30)aryl, and L2 represents a substituted or unsubstituted (C6-C30)arylene, Ar3 or Ar4 and L2 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring. In one embodiment of the present disclosure, if Ar3 or Ar4 represents an phenyl and L2 represents an phenylene, Ar3 or Ar4 and L2 may be linked via a single bond to form a carbazole ring.
In formula 1, R1 and R2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring. In one embodiment of the present disclosure, R1 and R2 each independently represent hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic (5- to 15-membered) ring. In another embodiment of the present disclosure, R1 and R2 each independently represent hydrogen, an unsubstituted (C6-C12)aryl, or an unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a mono- or polycyclic (5- to 15-membered) ring unsubstituted or substituted with a (C1-C6)alkyl or an (C6-C12)aryl. Specifically, R1 and R2 may each independently represent hydrogen, phenyl, dibenzofuranyl, dibenzothiophenyl, etc.; or may be linked to an adjacent substituent to form a benzene ring, a dimethylindene ring, a benzofuran ring, a benzothiophene ring, a naphthothiophene ring, a phenylindole ring, or a phenylbenzindole ring.
In formula 1, m and n each independently represent an integer of 0 to 2, with a proviso that at least one of m and n is 1 or more. In one embodiment of the present disclosure, if m is 0, n is 1 or 2, and if m is 1, n is 0.
In formula 1, p and q each independently represent an integer of 1 to 4, in which if p and q represent an integer of 2 or more, each of R1 and R2 may be the same or different.
In formula 2, X represents -NR11-, -CR12R13-, -O-, or -S-.
In formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl. In one embodiment of the present disclosure, HAr represents a substituted or unsubstituted, nitrogen-containing (3- to 30-membered)heteroaryl. In another embodiment of the present disclosure, HAr represents a substituted or unsubstituted, nitrogen-containing (5- to 20-membered)heteroaryl. In a further embodiment of the present disclosure, HAr represents a nitrogen-containing (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, or (C6-C12)aryl(5- to 15- membered)heteroaryl. Specifically, HAr represents a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted benzoimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridyl, a substituted or unsubstituted phenanthridinyl, a substituted or unsubstituted benzofuranopyrimidinyl, a substituted or unsubstituted benzothiophenopyrimidinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted pyridoquinoxalinyl, a substituted or unsubstituted pyrazinoquinoxalinyl, a substituted or unsubstituted dibenzoquinoxalinyl, or a substituted or unsubstituted pyridobenzoquinoxalinyl, in which these may be further substituted with at least one substituent selected from the group consisting of phenyl, naphthyl, biphenyl, naphthylphenyl, methylphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and phenylcarbazolyl.
In formula 2, L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene. In one embodiment of the present disclosure, L represents a single bond, or a substituted or unsubstituted (C6-C12)arylene. In another embodiment of the present disclosure, L represents a single bond, or an unsubstituted (C6-C12)arylene. Specifically, L may represent a single bond, phenylene, or naphthylene.
In formula 2, R11 to R13 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl. In one embodiment of the present disclosure, R11 represents a substituted or unsubstituted (C6-C12)aryl, and R12 and R13 each independently represent a substituted or unsubstituted (C1-C6)alkyl. In another embodiment of the present disclosure, R11 represents an unsubstituted (C6-C12)aryl, and R12 and R13 each independently represent an unsubstituted (C1-C6)alkyl. Specifically, R11 may represent phenyl, and R12 and R13 may each independently represent methyl.
In formula 2, R3 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring. In one embodiment of the present disclosure, R3 to R5 each independently represent hydrogen.
In formula 2, a, b, and c each independently represent an integer of 1 to 4, in which if a, b, and c represent an integer of 2 or more, each of R3, R4, and R5 may be the same or different.
In the formulas of the present disclosure, if a substituent is linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring, the ring may be a mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in which the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
In the formulas of the present disclosure, the heteroaryl(ene) may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be substituted with at least one substituent selected from the group consisting of deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, and a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
Herein, "(C1-C30)alkyl" is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30)alkenyl" is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30)alkynyl" is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. "(C3-C30)cycloalkyl" is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7- membered)heterocycloalkyl" is meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si, and P, and preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. "(C6-C30)aryl(ene)" is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 25, and more preferably 6 to 20, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, phenanthrenylphenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. "(3- to 30-membered)heteroaryl(ene)" is meant to be an aryl group having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond. The above heteroaryl may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, naphthothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, benzoquinazolinyl, benzoquinoxalinyl, pyridoquinoxalinyl, pyrazinoquinoxalinyl, dibenzoquinoxalinyl, and pyridobenzoquinoxalinyl. "Nitrogen-containing (5- to 30-membered)heteroaryl" is meant to be an aryl group having 5 to 30 ring backbone atoms, including at least one heteroatom of N, in which the number of the ring backbone atoms is preferably 5 to 20, and more preferably 5 to 15, and the number of heteroatoms is preferably 1 to 4. The above nitrogen-containing heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond. The above nitrogen-containing heteroaryl may include a monocyclic ring-type heteroaryl such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridinyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, benzoquinazolinyl, benzoquinoxalinyl, pyridoquinoxalinyl, pyrazinoquinoxalinyl, dibenzoquinoxalinyl, and pyridobenzoquinoxalinyl. "Halogen" includes F, Cl, Br, and I.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent. In formulas 1, 2, 1-1, and 1-2, the substituents of the substituted alkyl, the substituted alkoxy, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di- alkylamino, the substituted mono- or di- arylamino, the substituted alkylarylamino, and the substituted ring in Ar1 to Ar4, Ar11 to Ar13, HAr, R1 to R5, R11 to R13, R21 to R26, R31 to R33, L, L1, L2, and L11 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30) alkenyl, a (C2-C30) alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (3- to 7-membered)heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di- (C1-C30)alkylamino, a mono- or di- (C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl; preferably at least one selected from the group consisting of a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl, a (C6-C20)aryl, a tri(C6-C12)arylsilyl, and a (C1-C6)alkyl(C6-C20)aryl. Specifically, said substituent may be methyl, phenyl, biphenyl, phenanthrenyl, naphthylphenyl, methylphenyl, dimethylfluorenyl, triphenylsilyl, dibenzofuranyl, dibenzothiophenyl, or phenylcarbazolyl.
The compound represented by formula 1 includes the following compounds, but is not limited thereto:
The compound represented by formula 2 includes the following compounds, but is not limited thereto:
The compounds represented by formulas 1 and 2 according to the present disclosure can be prepared by a synthetic method known to a person skilled in the art. For example, the compound represented by formula 1 can be prepared by referring to Korean Patent Application Laying-Open Nos. 2013-0106255 (published on September 27, 2013), 2014-0108637 (published on September 12, 2014), 2014-0068883 (published on June 9, 2014), etc., and the compound represented by formula 2 can be prepared by referring to Korean Patent Application Laying-Open No. 2015-0032447 (published on March 26, 2015), etc., but is not limited thereto.
The present disclosure provides a mixture comprising a combination of the compound represented by formula 1 and the compound represented by formula 2. The mixture may be used as an organic electroluminescent material.
The organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may comprise a plurality of organic electroluminescent materials in which the compound represented by formula 1 is included as a first organic electroluminescent material, and the compound represented by formula 2 is included as a second organic electroluminescent material. In one embodiment of the present disclosure, the organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, in which the light-emitting layer may comprise the compound represented by formula 1 and the compound represented by formula 2.
The organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one organic layer between the anode and the cathode, in which the organic layer comprises a light-emitting layer. The light-emitting layer comprises a host and a phosphorescent dopant. The host comprises a plurality of host materials, in which at least a first host compound of the plural host materials is represented by formula 1, and a second host compound is represented by formula 2.
The light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer of which two or more layers are stacked. In the plurality of host materials according to the present disclosure, the first and second host materials may both be comprised in one layer or may be respectively comprised in different light-emitting layers. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound with respect to the host compound is less than 20 wt%.
The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, a hole blocking layer, and an electron blocking layer.
In the organic electroluminescent device according to the present disclosure, the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1. The weight ratio is preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to 60:40, and still more preferably about 50:50.
The dopant comprised in the organic electroluminescent device according to the present disclosure may be at least one fluorescent or phosphorescent dopant, and preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The dopant comprised in the organic electroluminescent device according to the present disclosure may include the compound represented by the following formula 101, but is not limited thereto.
In formula 101, L is selected from the following structures:
R100 to R103 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (C3-C30)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R100 to R103 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline;
R104 to R107 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or adjacent substituents of R104 to R107 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine;
R201 to R211, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or adjacent substituents of R201 to R211 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring; and
n represents an integer of 1 to 3.
Specifically, the dopant material includes the following compounds, but is not limited thereto:
The organic electroluminescent device according to the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
In addition, in the organic electroluminescent device according to the present disclosure, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
In the organic electroluminescent device according to the present disclosure, at least one layer (hereinafter, "a surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer is preferably placed on an inner surface(s) of at least one of a pair of electrodes. Specifically, a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Between the anode and the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used. Multiple hole injection layers can be used in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds can be simultaneously used in each layer. The hole transport layer or the electron blocking layer can also be formed of multi-layers.
Between the light-emitting layer and the cathode, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used. Multiple electron buffer layers can be used in order to control the injection of the electrons and enhance the interfacial characteristics between the light-emitting layer and the electron injection layer. Two compounds can be simultaneously used in each layer. The hole blocking layer or the electron transport layer can also be formed of multi-layers, and each layer can comprise two or more compounds.
In addition, in the organic electroluminescent device according to the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge-generating layer to produce an electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
When using a solvent in a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
In addition, the first and the second host compounds of the present disclosure may be film-formed in the above-listed methods, commonly by a co-evaporation process or a mixture-evaporation process. The co-evaporation is a mixed deposition method in which two or more materials are placed in a respective individual crucible source and a current is applied to both cells at the same time to evaporate the materials. The mixture-evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporating them, and a current is applied to the cell to evaporate the materials.
By using the organic electroluminescent device of the present disclosure, a display system or a lighting system can be produced.
Hereinafter, the luminescent properties of the organic electroluminescent device comprising the plurality of host materials of the present disclosure will be explained in detail with reference to the following examples.
Comparative Example 1: Production of a red light-emitting OLED not
according to the present disclosure
An OLED not according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-7 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Compound HI-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. Compound H2-1 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-39 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 were evaporated in a weight ratio of 50:50 as electron transport materials to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED was produced. All the materials used for producing the OLED were purified by vacuum sublimation at 10-6 torr.
Device Examples 1 to 5: Production of a red light-emitting OLED
according to the present disclosure
In Device Examples 1 to 5, OLEDs were produced in the same manner as in Comparative Example 1, except that the first and second host compounds shown in Table 1 below as hosts were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited at a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
The driving voltage, luminous efficiency, light-emitting color, and the time taken for luminance to decrease from 100% to 95% at a luminance of 5,000 nit (lifespan; T95) of the OLEDs produced in Comparative Example 1 and Device Examples 1 to 5 are provided in Table 1 below. In addition, Figure 1 illustrates current efficiency versus luminance of the OLEDs produced in Comparative Example 1 and Device Example 2.
From Device Examples 1 to 3, it is confirmed that the plurality of host materials of the present disclosure may be used to improve luminous efficiency and lifespan characteristic, while maintaining the driving voltage at a similar level or reducing the driving voltage. In particular, as in Figure 1, the combination of the host materials significantly improves roll-off compared to the comparative example using a single host material.
[Characteristic Analysis]
In order to support the theory of the combination of host compounds mentioned herein, a Hole Only Device (HOD) and an Electron Only Device (EOD) were produced to compare the current characteristic of the combination of the first and second host compounds used in the present disclosure versus only the second host compound. The device structures of the HOD and EOD are as follows.
Hole Only Device (HOD) Example
An ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-7 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 10 nm on the ITO substrate. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the hole injection layer. Next, compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 10 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, a light-emitting layer was formed thereon as follows: Compound H2-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the second hole transport layer. Compound HT-1 was then introduced into one cell of the vacuum vapor deposition apparatus and evaporated to form an electron blocking layer having a thickness of 20 nm on the light-emitting layer. Next, an Al cathode having a thickness of 80 nm was deposited on the electron blocking layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. HOD was produced in the same manner, except that, in the case of a mixture of a first host compound and a second host compound, the first host compound (H1-7) and the second host compound (H2-1) were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited at a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm. Voltages at the current density of 10 mA/cm2 and 100 mA/cm2 are shown in Table 2 below.
Electron Only Device (EOD) Example
4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine (B4PyMPM) was introduced into one cell of a vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate, thereby forming a hole blocking layer (HBL) having a thickness of 10 nm on ITO. Next, compound H2-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the hole blocking layer. Compound ET-1 and lithium quinolate were introduced into one cell and another cell of the vacuum vapor deposition apparatus, respectively, and the two materials were evaporated at the same rate and doped in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. All the materials used for producing the OLED were purified by vacuum sublimation at 10-6 torr. EOD was produced in the same manner, except that, in the case of a mixture of a first host compound and a second host compound, the first host compound (H1-7) and the second host compound (H2-1) were introduced into two cells of the vacuum vapor deposition apparatus and compound D-39 was introduced into another cell of the apparatus, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously deposited in a different rate in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm. Voltages at the current density of 10 mA/cm2 and 100 mA/cm2 are shown in Table 3 below.
As can be seen from Table 2 above, according to the HOD Example, the device comprising a light-emitting layer of only compound H2-1 showed relatively high driving voltage characteristic compared to the device comprising the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound), and thus it shows a hole injection blocking characteristic. Meanwhile, it is confirmed that the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound) showed significantly improved hole current chatacteristic due to compound H1-7 (the first host compound). In addition, as can be seen from Table 3 above, according to the EOD Example, the device comprising a light-emitting layer of only compound H2-1 showed relatively low driving voltage characteristic compared to the device comprising the combination of Compound H1-7 (the first host compound) and compound H2-1 (the second host compound). Meanwhile, it is confirmed that the combination of compound H1-7 (the first host compound) and compound H2-1 (the second host compound) showed slightly reduced electron current chatacteristic due to compound H1-7 (the first host compound). As a result, the combination of the first host compound and the second host compound according to the present disclosure showed relatively good charge balance characteristic by relatively improving hole current characteristic and slightly reducing electron current characteristic.
The compounds used in the Comparative Example and Device Examples are shown in Table 4 below.
Claims (8)
- 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:whereinAr1 to Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar1 and Ar2, and Ar3 and Ar4 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;L1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryl(ene);L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;if Ar1 or Ar2 represents a substituted or unsubstituted (C6-C30)aryl, and L1 represents a substituted or unsubstituted (C6-C30)arylene, Ar1 or Ar2 and L1 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;if Ar3 or Ar4 represents a substituted or unsubstituted (C6-C30)aryl, and L2 represents a substituted or unsubstituted (C6-C30)arylene, Ar3 or Ar4 and L2 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;R1 and R2 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring;m and n each independently represent an integer of 0 to 2, with a proviso that at least one of m and n is 1 or more; andp and q each independently represent an integer of 1 to 4, in which if p and q represent an integer of 2 or more, each of R1 and R2 may be the same or different;whereinX represents -NR11-, -CR12R13-, -O-, or -S-;HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;R11 to R13 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;R3 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) ring; anda, b, and c each independently represent an integer of 1 to 4, in which if a, b, and c represent an integer of 2 or more, each of R3, R4, and R5 may be the same or different.
- The plurality of host materials according to claim 1, wherein formula 1 is represented by the following formula 1-1 or 1-2:whereinAr11 to Ar13 each independently represent a substituted or unsubstituted (C6-C30)aryl; or Ar11 and Ar12 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) ring;L11 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;if Ar11 or Ar12 represents a substituted or unsubstituted (C6-C30)aryl, and L11 represents a substituted or unsubstituted (C6-C30)arylene, Ar11 or Ar12 and L11 may be linked via a single bond to form a substituted or unsubstituted (3- to 30-membered) ring;at least one of a and b, b and c, c and d, e and f, f and g, or g and h in formulas 1-1 and 1-2 and two * positions of the following formula 1-a, 1-b, or 1-c may be fused to form a ring:X1 represents NR31, O, S, or CR32R33;R31 to R33 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;R21 to R26 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, 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 mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; andr represents 1 or 2.
- The plurality of host materials according to claim 1, wherein HAr in formula 2 represents a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted benzoimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridyl, a substituted or unsubstituted phenanthridinyl, a substituted or unsubstituted benzofuranopyrimidinyl, a substituted or unsubstituted benzothiophenopyrimidinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted pyridoquinoxalinyl, a substituted or unsubstituted pyrazinoquinoxalinyl, a substituted or unsubstituted dibenzoquinoxalinyl, or a substituted or unsubstituted pyridobenzoquinoxalinyl.
- The plurality of host materials according to claim 1, wherein the substituents of the substituted alkyl, the substituted alkoxy, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di- alkylamino, the substituted mono- or di- arylamino, the substituted alkylarylamino, and the substituted ring in Ar1 to Ar4, HAr, R1 to R5, R11 to R13, L, L1, and L2 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30) alkenyl, a (C2-C30) alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (3- to 7-membered)heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di- (C1-C30)alkylamino, a mono- or di- (C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl.
- The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds:
- The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is selected from the following compounds:
- A mixture comprising a combination of the compound represented by formula 1 according to claim 1 and the compound represented by formula 2 according to claim 1.
- An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, and the host comprises the plurality of host materials according to claim 1.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410828777.0A CN118834156A (en) | 2017-07-26 | 2018-07-25 | Multiple host materials and organic electroluminescent device comprising the same |
| CN201880049333.XA CN110945675B (en) | 2017-07-26 | 2018-07-25 | Multiple host materials and organic electroluminescent device comprising the same |
| US16/631,186 US20200216392A1 (en) | 2017-07-26 | 2018-07-25 | A plurality of host materials and organic electroluminescent device comprising the same |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20170094827 | 2017-07-26 | ||
| KR10-2017-0094827 | 2017-07-26 | ||
| KR1020180083455A KR102667927B1 (en) | 2017-07-26 | 2018-07-18 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR10-2018-0083455 | 2018-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2019022512A1 true WO2019022512A1 (en) | 2019-01-31 |
Family
ID=65040668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2018/008434 WO2019022512A1 (en) | 2017-07-26 | 2018-07-25 | A plurality of host materials and organic electroluminescent device comprising the same |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN118834156A (en) |
| WO (1) | WO2019022512A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| CN112239666A (en) * | 2019-07-18 | 2021-01-19 | 罗门哈斯电子材料韩国有限公司 | Multiple host materials and organic electroluminescent device comprising the same |
| US12108666B2 (en) | 2018-09-26 | 2024-10-01 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140141933A (en) * | 2013-06-03 | 2014-12-11 | 롬엔드하스전자재료코리아유한회사 | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| KR20150001101A (en) * | 2013-06-26 | 2015-01-06 | 덕산하이메탈(주) | An organic electronic element using compound for organic electronic element, and an electronic device thereof |
| KR20160011582A (en) * | 2014-07-22 | 2016-02-01 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescence Device |
| KR20170049714A (en) * | 2015-10-27 | 2017-05-11 | 삼성디스플레이 주식회사 | An organic light emitting device |
| KR20170075877A (en) * | 2015-12-23 | 2017-07-04 | 삼성디스플레이 주식회사 | Organic light-emitting device |
-
2018
- 2018-07-25 CN CN202410828777.0A patent/CN118834156A/en active Pending
- 2018-07-25 WO PCT/KR2018/008434 patent/WO2019022512A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140141933A (en) * | 2013-06-03 | 2014-12-11 | 롬엔드하스전자재료코리아유한회사 | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| KR20150001101A (en) * | 2013-06-26 | 2015-01-06 | 덕산하이메탈(주) | An organic electronic element using compound for organic electronic element, and an electronic device thereof |
| KR20160011582A (en) * | 2014-07-22 | 2016-02-01 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescence Device |
| KR20170049714A (en) * | 2015-10-27 | 2017-05-11 | 삼성디스플레이 주식회사 | An organic light emitting device |
| KR20170075877A (en) * | 2015-12-23 | 2017-07-04 | 삼성디스플레이 주식회사 | Organic light-emitting device |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10672989B2 (en) | 2017-12-06 | 2020-06-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10680181B2 (en) | 2017-12-06 | 2020-06-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11557730B2 (en) | 2017-12-06 | 2023-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11569449B2 (en) | 2017-12-06 | 2023-01-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US12108666B2 (en) | 2018-09-26 | 2024-10-01 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
| CN112239666A (en) * | 2019-07-18 | 2021-01-19 | 罗门哈斯电子材料韩国有限公司 | Multiple host materials and organic electroluminescent device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN118834156A (en) | 2024-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3268449A1 (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
| WO2016148390A1 (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
| EP3551623A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3446345A1 (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
| WO2015160224A1 (en) | Multi-component host material and an organic electroluminescence device comprising the same | |
| WO2016013867A1 (en) | Organic electroluminescent device | |
| WO2016010402A1 (en) | Organic electroluminescent device | |
| EP3207045A1 (en) | A plurality of host materials and an organic electroluminescence device comprising the same | |
| EP3183234A1 (en) | A plurality of host materials and an organic electroluminescence device comprising the same | |
| WO2015167259A1 (en) | Multi-component host material and organic electroluminescent device comprising the same | |
| WO2015178732A1 (en) | Multi-component host material and an organic electroluminescence device comprising the same | |
| WO2016036171A1 (en) | A plurality of host materials and organic electroluminescent devices comprising the same | |
| EP3494117A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3313958A1 (en) | Multi-component host material and organic electroluminescent device comprising the same | |
| WO2016080791A1 (en) | A plurality of host materials and an organic electroluminescent device comprising the same | |
| WO2018021841A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3140367A1 (en) | Multi-component host material and organic electroluminescent device comprising the same | |
| EP3172780A1 (en) | Organic electroluminescent device | |
| WO2015037965A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| EP3119751A1 (en) | Electron buffering material and organic electroluminescent device | |
| WO2014185751A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2016013875A1 (en) | Organic electroluminescent device | |
| WO2015142040A1 (en) | Electron buffering material and organic electroluminescent device | |
| EP3201200A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2017183859A1 (en) | A plurality of host materials and organic electroluminescent device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 18838408 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 18838408 Country of ref document: EP Kind code of ref document: A1 |