CN106164046A - 多组分主体材料和包含所述多组分主体材料的有机电致发光装置 - Google Patents
多组分主体材料和包含所述多组分主体材料的有机电致发光装置 Download PDFInfo
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- CN106164046A CN106164046A CN201580019468.8A CN201580019468A CN106164046A CN 106164046 A CN106164046 A CN 106164046A CN 201580019468 A CN201580019468 A CN 201580019468A CN 106164046 A CN106164046 A CN 106164046A
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- alkyl
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- 239000000463 material Substances 0.000 title abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 45
- -1 xenyl Chemical group 0.000 claims description 45
- 229910000077 silane Inorganic materials 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001343 alkyl silanes Chemical group 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 238000006884 silylation reaction Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- RQQDJYROSYLPPK-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 RQQDJYROSYLPPK-UHFFFAOYSA-N 0.000 claims description 4
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 150000005054 naphthyridines Chemical class 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical group C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 117
- 239000002585 base Substances 0.000 description 93
- 238000004519 manufacturing process Methods 0.000 description 20
- 230000005540 biological transmission Effects 0.000 description 17
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000010549 co-Evaporation Methods 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
- 230000004888 barrier function Effects 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical compound [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-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
- 241000790917 Dioxys <bee> Species 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 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
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 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
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- 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
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 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
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- 150000003852 triazoles Chemical class 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种多组分主体材料和一种包含所述多组分主体材料的有机电致发光装置。通过包含多组分主体化合物的特定组合,根据本发明的有机电致发光装置可提供高的发光效率和优异的使用寿命特性。
Description
技术领域
本发明涉及多组分主体材料和包含所述多组分主体材料的有机电致发光装置。
背景技术
电致发光装置(EL装置)为一种自发光装置,其优点在于其提供较宽的视角、较大的对比率和较快的响应时间。有机EL装置最初由Eastman Kodak通过使用小芳香族二胺分子和铝配合物作为材料以形成发光层[应用物理学报(Appl.Phys.Lett.)51,913,1987]而开发。
有机EL装置(OLED)为通过向有机电致发光材料施加电力而将电能改变成光的装置,且一般具有包含阳极、阴极及在阳极与阴极之间的有机层的结构。有机EL装置的有机层可以由空穴注入层、空穴传输层、电子阻挡层、发光层(其包含主体材料和掺杂材料)、电子缓冲层、空穴阻挡层、电子传输层、电子注入层等组成,并且用于有机层的材料由其功能分类为空穴注入材料、空穴传输材料、电子阻挡材料、发光材料、电子缓冲材料、空穴阻挡材料、电子传输材料、电子注入材料等。在有机EL装置中,由于电压的施加,空穴从阳极注入到发光层,电子从阴极注入到发光层,且高能量的激子通过空穴和电子的再结合形成。通过此能量,发光有机化合物达到激发态,且通过由于发光有机化合物的激发态回到基态产生的能量发射光而发光。
决定有机EL装置中的发光效率的最重要因素是发光材料。发光材料必须具有高量子效率、高电子及空穴迁移率,且形成的发光材料层必须均匀且稳定。发光材料根据发光的颜色分为发蓝光材料、发绿光材料及发红光材料,另外发黄光材料或发橙光材料。此外,发光材料还可根据其功能分类为主体材料和掺杂材料。近来,开发具有高效率和使用寿命的有机EL装置装置是迫切的问题。具体来说,考虑OLED的中等或大尺寸面板的EL特性需求,必须迫切地开发与常规材料相比显示更好性能的材料。以固态用作溶剂且传递能量的主体材料需要具有高纯度及适于真空沉积的分子量。此外,主体材料需要具有高玻璃化转变温度及高热分解温度以实现热稳定性、高电-化学稳定性以实现长使用寿命、易于形成非晶形薄膜、对邻近层材料的良好粘合性及不迁移至其它层。
发光材料可以主体和掺杂剂的组合形式使用来提高色纯度、发光效率和稳定性。一般而言,具有优异特性的EL装置具有包含通过将掺杂剂掺杂到主体形成的发光层。由于当使用掺杂剂/主体材料系统作为发光材料时,主体材料极大地影响EL装置的效率和使用寿命,因此其选择是至关重要的。
国际公布第WO 2013/168688A1号和第WO 2009/060757A1号和日本专利申请公开第2013-183036A1号等公开一种使用双咔唑衍生物作为主体材料的有机电致发光装置。然而,这些参考文献未能公开一种使用包含包括含氮杂芳基的双咔唑衍生物和咔唑衍生物的多组分主体的有机电致发光装置。
发明内容
需要解决的问题
本发明的目标是提供一种具有高效率和长使用寿命的有机电致发光装置。
问题的解决方案
本发明人发现上述目标可以通过一种有机电致发光装置来实现,所述有机电致发光装置包含至少一个在阳极与阴极之间的发光层,其中发光层包含主体和磷光掺杂剂,主体由多组分主体化合物组成,多组分主体化合物的至少第一主体化合物由以下式1表示并且第二主体化合物由以下式2表示:
其中
A1和A2各自独立地表示经取代或未经取代的(C6-C30)芳基;
L1表示经取代或未经取代的(C6-C30)亚芳基;
X1到X16各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换;
其中
Ma表示经取代或未经取代的含氮(5元到11元)杂芳基;
La表示单键或经取代或未经取代的(C6-C30)亚芳基;
Xa到Xh各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换;并且
杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
本发明的效果
根据本发明,提供一种具有高效率及长使用寿命的有机电致发光装置,且有可能使用所述有机电致发光装置制造显示装置或照明装置。
具体实施方式
在下文中,将对本发明进行详细描述。然而,以下描述旨在解释本发明,并且不打算以任何方式限制本发明的范围。
在下文中,将详细地描述包含式1和式2的有机电致发光化合物的有机电致发光装置。
由式1表示的化合物可由式3、4、5或6表示:
其中
A1、A2、L1和X1到X16如式1中所定义。
在以上式1中,A1及A2各独立地表示经取代或未经取代的(C6-C30)芳基;优选地,各独立地表示经取代或未经取代的(C6-C18)芳基;更优选地,各独立地表示未经氰基、(C1-C6)烷基、(C6-C12)芳基或三(C6-C12)芳基硅烷基取代或经其取代的(C6-C18)芳基,并且甚至更优选地,各独立地表示苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、三亚苯基、芘基、并四苯基、苝基、屈基或荧蒽基。
在以上式1中,X1到X16各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换,优选地,各自独立地表示氢、氰基、经取代或未经取代的(C6-C20)芳基、经取代或未经取代的(5元到20元)杂芳基或经取代或未经取代的三(C6-C12)芳基硅烷基,并且更优选地,各自独立地表示氢、氰基、未经氰基取代或经其取代的(C6-C20)芳基、未经取代的(5元到20元)杂芳基或未经取代的三(C6-C12)芳基硅烷基。
在以上式1中,L1表示经取代或未经取代的(C6-C30)亚芳基,优选地表示经取代或未经取代的(C6-C15)亚芳基,并且更优选地,表示未经氰基、(C1-C6)烷基或三(C6-C12)芳基硅烷基取代或经其取代的(C6-C15)亚芳基。
此外,L1可由式7到式19中的一者表示:
其中
Xi到Xp各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换。
优选地,Xi到Xp可各自独立地表示氢、卤素、氰基、(C1-C10)烷基、(C3-C20)环烷基、(C6-C12)芳基、(C1-C6)烷基二(C6-C12)芳基硅烷基或三(C6-C12)芳基硅烷基,并且更优选地,各自独立地表示氢、氰基、(C1-C6)烷基或三(C6-C12)芳基硅烷基。
在以上式2中,Ma表示经取代或未经取代的含氮(5元到11元)杂芳基,优选地,表示经取代或未经取代的含氮(6元到10元)杂芳基,并且更优选地,表示经未经取代的(C6-C18)芳基取代的含氮(6元到10元)杂芳基、经氰基取代的(C6-C12)芳基、经(C1-C6)烷基取代的(C6-C12)芳基、经三(C6-C12)芳基硅烷基取代的(C6-C12)芳基或(6元到15元)杂芳基。
此外,Ma可表示单环杂芳基或稠合杂芳基,所述单环杂芳基选自由以下各者组成的群组:吡咯基、咪唑基、吡唑基、三嗪基、四嗪基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基,所述稠合杂芳基选自由以下各者组成的群组:苯并咪唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、萘啶基和喹喏啉基,并且优选地可表示三嗪基、嘧啶基、吡啶基、喹啉基、异喹啉基、喹唑啉基、萘啶基或喹喏啉基。
在以上式2中,La表示单键或经取代或未经取代的(C6-C30)亚芳基,优选地表示单键或经取代或未经取代的(C6-C12)亚芳基,并且更优选地,表示单键或未经三(C6-C10)芳基硅烷基取代或经其取代的(C6-C12)亚芳基。
此外,La可表示单键或由如上式7到式19中的一者表示。
在以上式2中,Xa到Xh各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换,优选地各自独立地表示氢、氰基、经取代或未经取代的(C6-C15)芳基、经取代或未经取代的(10元到20元)杂芳基或经取代或未经取代的三(C6-C10)芳基硅烷基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C6-C20)芳香族环,并且更优选地,各自独立地表示氢;氰基;未经三(C6-C10)芳基硅烷基取代或经其取代的(C6-C15)芳基;未经(C6-C12)芳基或氰基(C6-C12)芳基取代或经其取代的(10元到20元)杂芳基;或未经取代的三(C6-C10)芳基硅烷基;或者键联到相邻取代基以形成经取代或未经取代的苯、经取代或未经取代的吲哚、经取代或未经取代的苯并吲哚、经取代或未经取代的茚、经取代或未经取代的苯并呋喃或经取代或未经取代的苯并噻吩。
本文中,“(C1-C30)烷基”意指具有1到30个碳原子的直链或支链烷基,其中碳原子的数目优选为1到20,更优选为1到10,并且包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等;“(C2-C30)烯基”意指具有2到30个碳原子的直链或支链烯基,其中碳原子的数目优选为2到20,更优选为2到10,且包括乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;“(C2-C30)炔基”意指具有2到30个碳原子的直链或支链炔基,其中碳原子的数目优选为2到20,更优选为2到10,且包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等;“(C3-C30)环烷基”为具有3到30个碳原子的单环或多环烃,其中碳原子的数目优选为3到20,更优选为3到7,且包括环丙基、环丁基、环戊基、环己基等;“(3元到7元)杂环烷基”为具有3到7个,优选5到7个环主链原子(包括至少一个选自B、N、O、S、P(=O)、Si以及P,优选O、S以及N的杂原子)的环烷基,并且包括四氢呋喃、吡咯烷、硫杂环戊烷、四氢吡喃等;“(C6-C30)(亚)芳基”为衍生自具有6到30个碳原子的芳香族烃的单环或稠环,其中碳原子的数目优选为6到20,更优选6到15,并且包括苯基、联苯基、三联苯基、萘基、联萘基、苯基萘基、萘基苯基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、三亚苯基、芘基、并四苯基、苝基、屈基、稠四苯基(naphthacenyl)、荧蒽基等;“(3元到30元)杂芳基”为具有3到30个环主链原子(包括至少一个,优选1到4个选自由B、N、O、S、P(=O)、Si和P组成的群组的杂原子)的芳基;为单环或与至少一个苯环稠合的稠环;可为部分饱和的;可为通过使至少一个杂芳基或芳基经由单键键联到杂芳基所形成的基团;并且包括单环型杂芳基,包括呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,和稠环型杂芳基,包括苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、苯并吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喏啉基、咔唑基、啡噁嗪基、啡啶基、苯并间二氧杂环戊烯基等;“含氮(5元到30元)杂芳基”为具有5到30,优选5到20,并且更优选5到15个环主链原子(包括至少一个杂原子,N)的芳基;为单环或与至少一个苯环稠合的稠环;可为部分饱和的;可通过使至少一个杂芳基或芳基经由单键键联到杂芳基形成的基团;并且包括单环型杂芳基,包括吡咯基、咪唑基、吡唑基、三嗪基、四嗪基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,和稠环型杂芳基,包括苯并咪唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喏啉基、咔唑基、啡啶基等。另外,“卤素”包括F、Cl、Br和I。
本文中,表述“经取代或未经取代的”中的“经取代的”意指某一官能团中的氢原子被另一个原子或基团(即取代基)替换。在式1和2中的A1、A2、L1、X1到X16、Ma、La以及Xa到Xh中,经取代的烷基、经取代的烯基、经取代的炔基、经取代的环烷基、经取代的(亚)芳基、经取代的杂芳基、经取代的三烷基硅烷基、经取代的三芳基硅烷基、经取代的二烷基芳基硅烷基、经取代的烷基二芳基硅烷基、经取代的单或二芳基氨基以及经取代的含氮杂芳基的取代基各自独立为至少一个选自由以下各者组成的群组:氘、卤素、氰基、羧基、硝基、羟基、(C1-C30)烷基、卤代(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)环烷基、(C3-C30)环烯基、(3元到7元)杂环烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、未经(C6-C30)芳基取代或经其取代的(3元到30元)杂芳基、未经氰基取代或经其取代的(C6-C30)芳基、(3元到30元)杂芳基、或三(C6-C30)芳基硅烷基、三(C1-C30)烷基硅烷基、三(C6-C30)芳基硅烷基、二(C1-C30)烷基(C6-C30)芳基硅烷基、(C1-C30)烷基二(C6-C30)芳基硅烷基、氨基、单或二(C1-C30)烷基氨基、单或二(C6-C30)芳基氨基、(C1-C30)烷基(C6-C30)芳基氨基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基和(C1-C30)烷基(C6-C30)芳基,并且优选为至少一个选自由以下各者组成的群组:氰基、(C1-C6)烷基、(5元到15元)杂芳基、未经氰基或三(C6-C12)芳基硅烷基取代或经其取代的(C6-C18)芳基、三(C6-C12)芳基硅烷基以及(C1-C6)烷基(C6-C12)芳基。
在式1中,作为X1到X16的三芳基硅烷基优选为三苯基硅烷基。
由式1表示的第一主体化合物包括以下化合物,但不限于此:
由式2表示的第二主体化合物包括以下化合物,但是不限于此:
根据本发明有机电致发光装置包含阳极;阴极;以及至少一个在阳极和阴极之间的有机层。有机层包含发光层,并且发光层包含主体和磷光掺杂剂。主体由多组分主体化合物组成,多组分主体化合物的至少第一主体化合物由式1表示并且第二主体化合物由式2表示。
发光层为光从其发射的层,并且可为单层或堆叠有两层或更多层的多层。在发光层中,优选的是以主体化合物计掺杂化合物的掺杂浓度小于20wt%。
所述有机层包含发光层,并且可进一步包含至少一个选自由空穴注入层、空穴传输层、电子传输层、电子注入层、夹层、空穴阻挡层以及电子阻挡层组成的群组的层。
根据本发明的有机电致发光装置,第一主体材料与第二主体材料的重量比在1:99到99:1的范围内。
掺杂剂优选为至少一种磷光掺杂剂。应用于根据本发明的有机电致发光装置的掺杂剂材料不受限制,但可优选选自铱、锇、铜以及铂的金属配合物,更优选地选自铱、锇、铜和铂的邻位金属配合物,且甚至更优选地为邻位金属化铱配合物。
磷光掺杂剂优选选自由以下式101到式103表示的化合物。
其中L选自以下结构:
R100表示氢、经取代或未经取代的(C1-C30)烷基或经取代或未经取代的(C3-C30)环烷基;
R101到R109和R111到R123各自独立地表示氢、氘、卤素、未经氘或卤素取代或经其取代的(C1-C30)烷基、氰基、经取代或未经取代的(C1-C30)烷氧基、经取代或未经取代的(C6-C30)芳基或经取代或未经取代的(C3-C30)环烷基;R106到R109的相邻取代基可彼此键联以形成经取代或未经取代的稠环,例如,未经烷基取代或经其取代的芴、未经烷基取代或经其取代的二苯并噻吩或未经烷基取代或经其取代的二苯并呋喃;且R120到R123的相邻代基可彼此键联以形成经取代或未经取代的稠环,例如,未经卤素、烷基或芳基取代或经其取代的喹啉;
R124到R127各自独立地表示氢、氘、卤素、经取代或未经取代的(C1-C30)烷基或经取代或未经取代的(C6-C30)芳基;并且R124到R127的相邻取代基可彼此键联以形成经取代或未经取代的稠环,例如,未经烷基取代或经其取代的芴、未经烷基取代或经其取代的二苯并噻吩或未经烷基取代或经其取代的二苯并呋喃;
R201到R211各自独立地表示氢、氘、卤素、未经取代或经氘或卤素取代的(C1-C30)烷基、经取代或未经取代的(C3-C30)环烷基或经取代或未经取代的(C6-C30)芳基,且R208到R211的相邻取代基可彼此键联以形成经取代或未经取代的稠环,例如,未经取代或经烷基取代的芴、未经取代或经烷基取代的二苯并噻吩或未经取代或经烷基取代的二苯并呋喃;
r和s各自独立地表示1到3的整数;当r或s为2或更大的整数时,每个R100可相同或不同;并且
e表示1到3的整数。
具体来说,磷光掺杂剂材料包括以下:
根据本发明的有机电致发光装置可进一步包含至少一种选自由有机层中的芳胺基化合物和苯乙烯基芳基胺基化合物组成的群组的化合物。
此外,在根据本发明的有机电致发光装置中,所述有机层可进一步包含至少一种选自由以下各者组成的群组的金属:周期表的第1族金属、第2族金属、第4周期过渡金属、第5周期过渡金属、镧系元素和d-过渡元素的有机金属,或包含所述金属的至少一种配合物。
根据本发明,至少一个层(下文中,“表面层”)优选地位于一个或两个电极的内表面上;选自硫族化合物层、金属卤化物层和金属氧化物层。具体来说,硅或铝的硫族化合物(包括氧化物)层优选地位于电致发光中间层的阳极表面上,并且金属卤化物层或金属氧化物优选地位于电致发光中间层的阴极表面上。此类表面层为有机电致发光装置提供运行稳定性。优选地,所述硫族化合物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;所述金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;并且所述金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在阳极和发光层之间,可使用选自空穴注入层、空穴传输层或电子阻挡层或由其组合形成的层。空穴注入层可使用多层以便降低从阳极到空穴传输层或电子阻挡层的空穴注入屏障(或空穴注入电压)。两种化合物可同时用于各层中。空穴传输层或电子阻挡层还可由多层形成。
在发光层和阴极之间,可使用选自电子缓冲层、空穴阻挡层、电子传输层或电子注入层或由其组合形成的层。电子缓冲层可使用多层以便控制电子的注入并且提高发光层与电子注入层之间的界面特性。两种化合物可同时用于各层中。空穴阻挡层或电子传输层还可由多层形成,且每层可包含两种或更多种化合物。
在根据本发明的有机电致发光装置中,电子传输化合物和还原性掺杂剂的混合区域、或空穴传输化合物和氧化性掺杂剂的混合区域优选地位于一对电极的至少一个表面上。在这种情况下,电子传输化合物被还原为阴离子,并且因此从混合区域注入电子并将其传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化为阳离子,且因此从混合区域注入空穴并将其传输到电致发光介质变得更加容易。优选地,氧化性掺杂剂包括各种路易斯酸(Lewis acid)和受体化合物;并且还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属以及其混合物。还原性掺杂剂层可用作电荷产生层以制造具有两个或更多个电致发光层并且发射白光的电致发光装置。
为了形成本发明的有机电致发光装置的每一层,可使用干膜形成方法,如真空蒸发、溅镀、等离子体以及离子电镀方法;或湿膜形成方法,如喷墨印刷、喷嘴印刷、狭缝涂布、旋转涂布、浸渍涂布以及流动涂布方法。本发明的第一主体化合物和第二主体化合物可经共-蒸发或混合物蒸发。
当使用湿膜形成方法时,薄膜可通过将形成每一层的材料溶解或扩散到任何适合的溶剂中来形成,所述溶剂如乙醇、氯仿、四氢呋喃、二噁烷等。溶剂可以为形成每一层的材料可溶解或扩散于其中并且不存在成膜能力问题的任何溶剂。
在本文中,共蒸发指示用于使两种或更多种材料沉积为混合物的方法,通过将所述两种或更多种材料中的每种引入到相应坩埚单元中,且向所述单元施加电流以便所述材料中的每种材料蒸发来进行。在本文中,混合物蒸发指示用于使两种或更多种材料沉积为混合物的方法,通过将所述两种或更多种材料在一个坩埚单元中混合,随后沉积,且向所述单元施加电流以便所述混合物蒸发来进行。
通过使用本发明的有机电致发光装置,可制造显示系统或照明系统。
在下文中,将参考以下实例详细说明包含本发明的主体化合物的装置的发光特性。
装置实例1-1至装置实例1-6:通过共-蒸发本发明的第一主体化合物和第二主体
化合物制备OLED装置
使用根据本发明的有机电致发光化合物制造OLED装置。将有机发光二极体(OLED)装置(吉奥马(Geomatec))的玻璃衬底上的透明电极氧化铟锡(ITO)薄膜(10Ω/sq)依次用三氯乙烯、丙酮、乙醇及蒸馏水进行超声洗涤,且然后储存于异丙醇中。然后,将ITO衬底安装在真空气相沉积设备的衬底固持器上。将N4,N4'-二苯基-N4,N4'-双(9-苯基-9H-咔唑-3-基)-[1,1'-联苯]-4,4'-二胺(化合物HI-1)引入到所述真空气相沉积设备的单元中,并且然后将所述设备的腔室中的压力控制到10-6托。此后,向所述单元施加电流以蒸发上述引入的材料,从而在ITO衬底上形成厚度为80nm的第一空穴注入层。接着,将1,4,5,8,9,12-六氮杂三亚苯基-六甲腈(化合物HI-2)引入到所述真空气相沉积设备的另一单元中,且通过向所述单元施加电流蒸发,从而在第一空穴注入层上形成厚度为5nm的第二空穴注入层。然后,将N-([1,1'-联苯]-4-基)-9,9-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-9H-芴-2-胺(化合物HT-1)引入到所述真空气相沉积设备的另一单元中,并且通过向所述单元施加电流而蒸发,从而在第二空穴注入层上形成厚度为10nm的第一空穴传输层。之后,将N,N-二([1,1'-联苯]-4-基)-4'-(9H-咔唑-9-基)-[1,1'-联苯]-4-胺(化合物HT-2)引入到所述真空气相沉积设备的另一单元中,并且通过向所述单元施加电流而蒸发,从而在第一空穴传输层上形成厚度为60nm的第二空穴传输层。将第一主体化合物和第二主体化合物作为主体材料分别引入到真空气相沉积设备的两个单元中。将掺杂剂化合物D-96引入到另一单元中。两种主体材料以1:1速率蒸发,而掺杂剂以与主体材料不同的速率蒸发,使得掺杂剂以按主体及掺杂剂的总量计3wt%的掺杂量沉积,以在空穴传输层上形成厚度为40nm的发光层。然后,分别将2,4-双(9,9-二甲基-9H-芴-2-基)-6-(萘-2-基)-1,3,5-三嗪(化合物ET-1)和喹啉锂(化合物EI-1)引入到真空气相沉积设备的两个单元中,并且以1:1速率蒸发以在发光层上形成厚度为30nm的电子传输层。在电子传输层上沉积喹啉锂(化合物EI-1)作为厚度为2nm的电子注入层之后,通过另一真空气相沉积设备沉积厚度为80nm的Al阴极。由此,制造OLED装置。
比较实例1-1至比较实例1-3:仅使用第二主体化合物作为主体制备OLED装置
以与装置实例1-1至装置实例1-6相同的方式制造OLED装置,不同之处在于,仅使用第二主体化合物作为发光层的主体。
在如上制造OLED的恒定电流下,测量了在1,000尼特下的驱动电压、发光效率、CIE颜色坐标以及5,000尼特亮度从100%降低到80%所花费的时间。
以下表1示出了如以上实例中制造的有机电致发光装置的发光特性。
[表1]
装置实例2-1至装置实例2-7:通过共-蒸发本发明的第一主体化合物和第二主体
化合物制备OLED装置
以与装置实例1-1至装置实例1-6相同的方式制造OLED装置,不同之处在于,形成3nm的第二空穴注入层;形成40nm的第一空穴传输层;未形成第二空穴传输层;掺杂化合物D-25以按主体和掺杂剂的总量计15wt%的掺杂量作为发光层的掺杂剂;通过以4:6的速率蒸发2,4-双(9,9-二甲基-9H-芴-2-基)-6-(萘-2-基)-1,3,5-三嗪和喹啉锂形成35nm的电子传输层;并且使用在发光层的主体中使用的第一主体化合物和第二主体化合物的其它组合。
装置实例2-8至装置实例2-9:通过共-蒸发本发明的第一主体化合物和第二主体
化合物制备OLED装置
以与装置实例1-1至装置实例1-6相同的方式制造OLED装置,不同之处在于,形成3nm的第二空穴注入层;形成40nm的第一空穴传输层;未形成第二空穴传输层;掺杂化合物D-1以按主体和掺杂剂的总量计15wt%的掺杂量作为发光层的掺杂剂;通过以4:6的速率蒸发2,4-双(9,9-二甲基-9H-芴-2-基)-6-(萘-2-基)-1,3,5-三嗪和喹啉锂形成35nm的电子传输层;并且使用在发光层的主体中使用的第一主体化合物和第二主体化合物的其它组合。
装置实例2-10:通过共-蒸发本发明的第一主体化合物和第二主体化合物制备
OLED装置
以与装置实例1-1至装置实例1-6相同的方式制造OLED装置,不同之处在于形成3nm的第二空穴注入层;形成40nm的第一空穴传输层;未形成第二空穴传输层;掺杂化合物D-136以按主体和掺杂剂的总量计15wt%的掺杂量作为发光层的掺杂剂;通过以4:6的速率蒸发2,4-双(9,9-二甲基-9H-芴-2-基)-6-(萘-2-基)-1,3,5-三嗪和喹啉锂形成35nm的电子传输层;并且使用在发光层的主体中使用的第一主体化合物和第二主体化合物的其它组合。
装置实例3-1至装置实例3-3:通过共-蒸发本发明的第一主体化合物和第二主体
化合物制备OLED装置
以与装置实例2-1至装置实例2-7相同的方式制造OLED装置,不同之处在于,形成10nm的第一空穴注入层;使用化合物HT-3形成30nm的第二空穴传输层;使用化合物D-136作为发光层的掺杂剂;并且使用在发光层的主体中使用的第一主体化合物和第二主体化合物的其它组合。
装置实例3-4:通过共-蒸发本发明的第一主体化合物和第二主体化合物制备OLED
装置
以与装置实例2-1至装置实例2-7相同的方式制造OLED装置,不同之处在于,形成10nm的第一空穴注入层;使用化合物HT-3形成30nm的第二空穴传输层;使用化合物D-168作为发光层的掺杂剂;并且使用在发光层的主体中使用的第一主体化合物和第二主体化合物的其它组合。
比较实例2-1至比较实例2-3:仅使用第一主体化合物作为主体制备OLED装置
以与装置实例2-1至装置实例2-7相同的方式制造OLED装置,不同之处在于,仅使用第一主体化合物作为发光层的主体。
比较实例3-1至比较实例3-3:仅使用第二主体化合物作为主体制备OLED装置
以与装置实例2-1至装置实例2-7相同的方式制造OLED装置,不同之处在于,仅使用第二主体化合物作为发光层的主体。
比较实例3-4至比较实例3-6:仅使用第二主体化合物作为主体制备OLED装置
以与装置实例2-8至装置实例2-9相同的方式制造OLED装置,不同之处在于,仅使用第二主体化合物作为发光层的主体。
比较实例4-1至比较实例4-3:仅使用第二主体化合物作为主体制备OLED装置
以与装置实例3-1至装置实例3-3相同的方式制造OLED装置,不同之处在于,仅使用第二主体化合物作为发光层的主体。
在如上制造OLED的恒定电流下,测量了在1,000尼特下的驱动电压、发光效率、CIE颜色坐标以及15,000尼特亮度从100%降低到80%所花费的时间。
以下表2示出了如以上实例中制造的有机电致发光装置的发光特性。
[表2]
装置实例4-1:通过共-蒸发本发明的第一主体化合物和第二主体化合物制备OLED
装置
以与装置实例1-1至装置实例1-6相同的方式制造OLED装置,不同之处在于,使用用于第二空穴传输层的化合物HT-4,并且使用如以下表3中列出的用于在发光层的主体中使用的第一主体化合物和第二主体化合物的化合物。
比较实例5-1:仅使用第二主体化合物作为主体制备OLED装置
以与装置实例4-1中相同的方式制造OLED装置,不同之处在于,仅使用表3的第二主体化合物作为发光层的主体。
在如上制造OLED的恒定电流下,测量了在1,000尼特下的驱动电压、发光效率、CIE颜色坐标以及5,000尼特亮度从100%降低到90%所花费的时间。
以下表3示出了如以上实例中制造的有机电致发光装置的发光特性。
[表3]
本发明的有机电致发光装置包含包含主体和磷掺杂剂的发光层,并且所述主体由多组分主体化合物的特定组合组成。本发明的装置相对于常规装置提供了优良的使用寿命特性。
Claims (9)
1.一种有机电致发光装置,其包含至少一个在阳极与阴极之间的发光层,其中所述发光层包含主体和磷光掺杂剂,所述主体由多组分主体化合物组成,所述多组分主体化合物的至少第一主体化合物由以下式1表示,并且第二主体化合物由以下式2表示。
其中
A1和A2各自独立地表示经取代或未经取代的(C6-C30)芳基;
L1表示经取代或未经取代的(C6-C30)亚芳基;
X1到X16各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换;
其中
Ma表示经取代或未经取代的含氮(5元到11元)杂芳基;
La表示单键或经取代或未经取代的(C6-C30)亚芳基;
Xa到Xh各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换;并且
所述杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子。
2.根据权利要求1所述的有机电致发光装置,其中在式1中,
A1及A2各自独立地选自由以下各者组成的群组:苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、三亚苯基、芘基、并四苯基、苝基、□基及荧蒽基。
3.根据权利要求1所述的有机电致发光装置,其中在式1中,
L1由以下式7到式19中的任一者表示:
其中
Xi到Xp各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换。
4.根据权利要求1所述的有机电致发光装置,其中在式2中,
Ma表示单环杂芳基或稠合杂芳基,所述单环杂芳基选自由以下各者组成的群组:吡咯基、咪唑基、吡唑基、三嗪基、四嗪基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基,所述稠合杂芳基选自由以下各者组成的群组:苯并咪唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、萘啶基和喹喏啉基。
5.根据权利要求1所述的有机电致发光装置,其中在式2中,La为单键或由下式7到式19中的一者表示:
其中
Xi到Xp各自独立地表示氢、氘、卤素、氰基、经取代或未经取代的(C1-C30)烷基、经取代或未经取代的(C2-C30)烯基、经取代或未经取代的(C2-C30)炔基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C6-C60)芳基、经取代或未经取代的(3元到30元)杂芳基、经取代或未经取代的三(C1-C30)烷基硅烷基、经取代或未经取代的三(C6-C30)芳基硅烷基、经取代或未经取代的二(C1-C30)烷基(C6-C30)芳基硅烷基、经取代或未经取代的(C1-C30)烷基二(C6-C30)芳基硅烷基或经取代或未经取代的单或二(C6-C30)芳基氨基;或键联到相邻取代基以形成经取代或未经取代的单环或多环(C3-C30)脂环族环或芳香族环,其碳原子可被至少一个选自氮、氧和硫的杂原子替换。
6.根据权利要求1所述的有机电致发光装置,其中在式2中,
Xa到Xh各自独立地表示氢;氰基;未经三(C6-C10)芳基硅烷基取代或经其取代的(C6-C15)芳基;未经(C6-C12)芳基或氰基(C6-C12)芳基取代或经其取代的(10元到20元)杂芳基;或未经取代的三(C6-C10)芳基硅烷基;或键联到相邻取代基以形成经取代或未经取代的苯、经取代或未经取代的吲哚、经取代或未经取代的苯并吲哚、经取代或未经取代的茚、经取代或未经取代的苯并呋喃或经取代或未经取代的苯并噻吩。
7.根据权利要求1所述的有机电致发光装置,其中在式1中,作为X1到X16的三芳基硅烷基为三苯基硅烷基。
8.根据权利要求1所述的有机电致发光装置,其中所述由式1表示的化合物选自由以下各者组成的群组:
9.根据权利要求1所述的有机电致发光装置,其中所述由式2表示的化合物选自由以下各者组成的群组:
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Also Published As
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EP3131879B1 (en) | 2023-09-13 |
JP6681340B2 (ja) | 2020-04-15 |
US20240090328A1 (en) | 2024-03-14 |
WO2015160224A1 (en) | 2015-10-22 |
KR101502316B1 (ko) | 2015-03-13 |
US20170125699A1 (en) | 2017-05-04 |
JP2017514302A (ja) | 2017-06-01 |
EP3131879A4 (en) | 2018-01-03 |
US20220216429A1 (en) | 2022-07-07 |
US20220216430A1 (en) | 2022-07-07 |
CN114551746A (zh) | 2022-05-27 |
EP3131879A1 (en) | 2017-02-22 |
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