CN108699069A - Heterocyclic compound and organic electroluminescent device comprising it - Google Patents
Heterocyclic compound and organic electroluminescent device comprising it Download PDFInfo
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- CN108699069A CN108699069A CN201780011526.1A CN201780011526A CN108699069A CN 108699069 A CN108699069 A CN 108699069A CN 201780011526 A CN201780011526 A CN 201780011526A CN 108699069 A CN108699069 A CN 108699069A
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- heterocyclic compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 37
- 239000000126 substance Substances 0.000 claims description 56
- 239000005416 organic matter Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 dimethyl fluorenyl Chemical group 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 238000002347 injection Methods 0.000 claims description 30
- 239000007924 injection Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 230000005540 biological transmission Effects 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 17
- 230000004888 barrier function Effects 0.000 claims description 11
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 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 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 168
- 230000000052 comparative effect Effects 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 150000001721 carbon Chemical group 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N CHCl3 Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- 238000001704 evaporation Methods 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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052738 indium Inorganic materials 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 150000003643 triphenylenes Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical group [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UJHSIDUUJPTLDY-UHFFFAOYSA-N (2-nitrophenyl)-phenylmethanone Chemical class [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 UJHSIDUUJPTLDY-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
- MPEOPBCQHNWNFB-UHFFFAOYSA-N 1-chloro-2-iodobenzene Chemical class ClC1=CC=CC=C1I MPEOPBCQHNWNFB-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- KIWFWRIRMKCXFZ-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)-1,3-oxazole Chemical compound C1=COC(C2=NNC=C2)=N1 KIWFWRIRMKCXFZ-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical class C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QBAMZCNRXHSQBH-UHFFFAOYSA-N C(C(C)C)OCC(C(OOCCCCC)(OC(C)CC)OC(C)(C)C)(C)C Chemical compound C(C(C)C)OCC(C(OOCCCCC)(OC(C)CC)OC(C)(C)C)(C)C QBAMZCNRXHSQBH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
This specification provides heterocyclic compound and the organic electroluminescent device comprising it.
Description
Technical field
This specification is related to heterocyclic compound and the organic electroluminescent device comprising it.
This specification advocates the South Korea patent application 10-2016- submitted to Koran Office on 2 15th, 2016
No. 0017271 priority, its contents are contained in this manual.
Background technology
Electroluminescent cell is one kind of emissive type display element, has that visual angle is wide, contrast is excellent and response speed
Spend fast advantage.
Organic illuminating element has the structure that organic film is configured between 2 electrodes.When to having with this structure
When machine light-emitting component applies voltage, it is combined into organic film from the electrons and holes of 2 electrode injections and is quenched to after
It shines simultaneously.Above-mentioned organic film can be made of as needed single-layer or multi-layer.
The material of organic film can have lighting function as needed.For example, as organic film material, can also make
Can be separately formed the compound of luminescent layer with itself, or can also use can play host-dopant system luminescent layer
Main body or dopant effect compound.In addition to this, as the material of organic film, can also use can play hole
The compound of the effects that injection, hole transport, electronic blocking, hole barrier, electron-transport or electron injection.
In order to improve performance, service life or the efficiency of organic electroluminescent device, the lasting material for requiring exploitation organic film.
Invention content
This specification provides heterocyclic compound and the organic electroluminescent device comprising it.
The application provides the heterocyclic compound indicated by following chemical formula 1.
[Chemical formula 1]
In above-mentioned chemical formula 1, Ar1 and Ar2 are same or different to each other, be each independently substituted or unsubstituted aryl,
Or substituted or unsubstituted heterocycle,
L1 to L3 is same or different to each other, and is each independently Direct Bonding, substituted or unsubstituted arlydene or takes
The heterocycle of generation or unsubstituted divalent,
R1 to R3 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted first
Silylation, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heterocycle, a are 0 to 2
Integer, the integer that b and c are 0 to 4, substituent group when a to c is 2 or more in bracket is identical or different.
In addition, the application provide organic electroluminescent device comprising:It is first electrode, opposed with above-mentioned first electrode
And the second electrode that has and have 1 layer or more of organic matter layer between above-mentioned first electrode and above-mentioned second electrode,
1 layer of above-mentioned heterocyclic compound contained above in above-mentioned organic matter layer.
Heterocyclic compound involved by the embodiment of the application is used for organic electroluminescent device, so as to drop
The driving voltage of low organic electroluminescent device is improved light efficiency, the longevity of element can be improved using the thermal stability of compound
Order characteristic.
Description of the drawings
Fig. 1 illustrates be sequentially laminated with substrate 1, anode 2, luminescent layer 3, cathode 4 organic electroluminescent device example.
Fig. 2, which is illustrated, is sequentially laminated with substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 3, electronics biography
The example of the organic electroluminescent device of defeated layer 7 and cathode 4.
Fig. 3 is the LC/MS spectrograms of the chemical formula 1-c of reaction equation 1.
Fig. 4 is the LC/MS spectrograms of the chemical formula 1A of reaction equation 1.
Fig. 5 is the LC/MS spectrograms of the compound 2 of synthesis example 2.
Fig. 6 is the LC/MS spectrograms of the compound 3 of synthesis example 3.
Fig. 7 is the LC/MS spectrograms of the compound 5 of synthesis example 5.
Symbol description
1:Substrate
2:Anode
3:Luminescent layer
4:Cathode
5:Hole injection layer
6:Hole transmission layer
7:Electron transfer layer
Specific implementation mode
In the following, being illustrated in more details to this specification.
This specification provides the heterocyclic compound indicated by above-mentioned chemical formula 1.
The illustration of substituent group is described below in this specification, and but not limited to this.
Above-mentioned " substitution " this term means that the hydrogen atom for the carbon atom for being incorporated into compound is replaced by other and takes
Dai Ji, substituted position do not limit as long as the position that hydrogen atom can be replaced with substituted position, i.e. substituent group
Fixed, when replacing 2 or more, 2 or more substituent groups can be the same or different from each other.
" substituted or unsubstituted " this term is meant by selected from deuterium, halogen group, cyano, nitre in this specification
1 or 2 or more substituent group substitution in base, hydroxyl, alkyl, naphthenic base, alkenyl, alkoxy, aryl and heterocycle,
Either is replaced or do not had any by the substituent group that 2 or more substituent groups in foregoing illustrative substituent group are formed by connecting
Substituent group.For example, " substituent group that 2 or more substituent groups are formed by connecting " can be xenyl.That is, xenyl can be virtue
Base can also be construed to the substituent group that 2 phenyl are formed by connecting.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, abovementioned alkyl can be linear chain or branched chain, and carbon atom number is not particularly limited, preferably 1 to 50.
As specific example, have methyl, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tertiary butyl, sec-butyl,
1- methyl butyls, 1- ethyl-butyls, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methylpents
Base, 2- methyl amyls, 4- methyl -2- amyls, 3,3- dimethylbutyls, 2- ethyl-butyls, heptyl, n-heptyl, 1- methylhexyls,
Cyclopentyl-methyl, cyclohexyl methyl, octyl, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propylpentyls, just
Nonyl, 2,2- dimethyl heptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methylhexyls,
5- methylhexyls etc., but not limited to this.
In this specification, naphthenic base is not particularly limited, but the naphthenic base that preferably carbon atom number is 3 to 60, specifically,
There are cyclopropyl, cyclobutyl, cyclopenta, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- first
Butylcyclohexyl, 2,3- Dimethylcyclohexyls, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl etc.,
But not limited to this.
In this specification, above-mentioned alkoxy can be straight chain, branch or ring.The carbon atom number of alkoxy does not limit especially
It is fixed, but preferably carbon atom number is 1 to 20.Specifically, can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, positive fourth
Oxygroup, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, isoamoxy, positive hexyloxy, 3,3- diformazans
Base butoxy, 2- ethyl-butoxies, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzyloxy, to methylbenzyloxy etc., but not
It is defined in this.
In this specification, above-mentioned alkenyl can be linear chain or branched chain, and carbon atom number is not particularly limited, but preferably 2 to
40.As specific example, there are vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- amylenes
Base, 2- pentenyls, 3- pentenyls, 3-methyl-1-butene base, 1,3- butadiene, allyl, 1- phenylethylene -1- bases, 2- phenyl
Ethylene -1- bases, 2,2- diphenylethlene -1- bases, 2- phenyl -2- (naphthalene -1- bases) ethylene -1- bases, bis- (hexichol -1- bases) second of 2,2-
Alkene -1- bases, Stilbene base, styryl etc., but not limited to this.
In this specification, in the case where above-mentioned aryl is monocyclic aryl, carbon atom number is not particularly limited, but preferred carbon
Atomicity is 6 to 25.Can be phenyl, xenyl, terphenyl etc., but be not limited to specifically, as monocyclic aryl
This.
Above-mentioned aryl be polyaromatic in the case of, carbon atom number is not particularly limited, but preferably carbon atom number be 10 to
24.Specifically, as polyaromatic can be naphthalene, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but do not limit
In this.
In this specification, above-mentioned fluorenyl can be substituted, and adjacent substituent group can be bonded to each other and form ring.
In the case of above-mentioned fluorenyl is substituted, Ke Yiwei Deng but not limited to this.
In this specification, heterocycle includes the hetero atom of more than one non-carbon, specifically, above-mentioned hetero atom can wrap
Atom containing more than one in O, N, Se and S etc..The carbon atom number of heterocycle is not particularly limited, and carbon atom number is preferably
2 to 60.As the example of heterocycle, have thiophenyl, furyl, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Diazole
Base, triazolyl, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, acridinyl, hydrogenated acridine base (for example,), pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrrole
Pyridine and pyrazinyl, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazole
Base, benzo carbazole base, dibenzo-carbazole base, aisaa benzothiophenyl, dibenzo thiophenyl, benzofuranyl, dibenzofuran group, benzene
And it is Silole base, dibenzo Silole base, phenanthroline (phenanthrolinylgroup), differentAzoles
Base, thiadiazolyl group, phenothiazinyl, phenoPiperazine base and their fused structure etc., it is not limited to this.In addition to this,
As the example of heterocycle, also include the heterocycle structure of sulfonyl, such as has
Deng.
In this specification, above-mentioned fused structure can be structure made of aromatic series hydrocarbon ring is condensed in the substituent group.For example,
As the condensed ring of benzimidazole, Ke Yiwei
Deng but not limited to this.
In this specification, arlydene refers to the group there are two binding site, i.e. divalent group in aryl.They are respectively 2
Valence base can be applicable in the explanation of above-mentioned aryl in addition to this.
In this specification, it is enterprising that " adjacent " group can refer to the atom being directly connected in the atom replaced with the substituent group
The substituent group of row substitution or other substituent groups replaced on the atom replaced by the substituent group.For example, in phenyl ring
Ortho position (ortho) substitution 2 substituent groups and same carbon in aliphatic ring on 2 substituent groups replacing be considered as
" adjacent " group each other.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, be each independently substitution or not
The heterocycle of the aryl of substituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 60.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, be each independently substitution or not
The heterocycle of the aryl of substituted carbon atom number 6 to 20 or substituted or unsubstituted carbon atom number 2 to 30.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, be each independently substitution or not
Substituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene
Base, substituted or unsubstituted dimethyl fluorenyl, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzo thiophene
Pheno base or substituted or unsubstituted carbazyl.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, and are each independently and are taken by aryl
Generation or unsubstituted phenyl are substituted with aryl or unsubstituted xenyl, are substituted with aryl or unsubstituted terphenyl, fragrant
The substituted or unsubstituted triphenylene of base is substituted with aryl or unsubstituted dimethyl fluorenyl, is substituted with aryl or unsubstituted
Dibenzofuran group is substituted with aryl or unsubstituted dibenzothiophene or is substituted with aryl or unsubstituted carbazyl.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, and are each independently and are taken by phenyl
Generation or unsubstituted phenyl, be substituted by phenyl or unsubstituted xenyl, be substituted by phenyl or unsubstituted terphenyl, by benzene
The substituted or unsubstituted triphenylene of base is substituted by phenyl or unsubstituted dimethyl fluorenyl, is substituted by phenyl or unsubstituted
Dibenzofuran group is substituted by phenyl or unsubstituted dibenzothiophene or is substituted by phenyl or unsubstituted carbazyl.
In one embodiment of this specification, Ar1 and Ar2 are same or different to each other, and are each independently and are taken by phenyl
Generation or unsubstituted phenyl, xenyl, terphenyl, triphenylene, be substituted by phenyl or unsubstituted dimethyl fluorenyl, by benzene
The substituted or unsubstituted dibenzofuran group of base is substituted by phenyl or unsubstituted dibenzothiophene or is substituted by phenyl
Or unsubstituted carbazyl.
In one embodiment of this specification, L1 is the Asia of Direct Bonding, substituted or unsubstituted carbon atom number 6 to 30
The heterocycle of aryl or the divalent of substituted or unsubstituted carbon atom number 2 to 60.
In one embodiment of this specification, L1 is the Asia of Direct Bonding, substituted or unsubstituted carbon atom number 6 to 20
The heterocycle of aryl or the divalent of substituted or unsubstituted carbon atom number 2 to 30.
In one embodiment of this specification, L1 is Direct Bonding, substituted or unsubstituted phenylene, substitution or does not take
The dibenzofuran group of the divalent in generation, the dibenzo thiophenyl of substituted or unsubstituted divalent or substituted or unsubstituted divalent
Fluorenyl.
In one embodiment of this specification, L1 be Direct Bonding, by the substituted or unsubstituted phenylene of alkyl, by alkane
The dibenzofuran group of the substituted or unsubstituted divalent of base, by the dibenzo thiophenyl of the substituted or unsubstituted divalent of alkyl or
By the fluorenyl of the substituted or unsubstituted divalent of alkyl.
In one embodiment of this specification, L1 is Direct Bonding, phenylene, the dibenzofuran group of divalent, divalent
The dimethyl fluorenyl of dibenzo thiophenyl, the fluorenyl of divalent or divalent.
In one embodiment of this specification, L2 and L3 are same or different to each other, be each independently Direct Bonding or
The substituted or unsubstituted arlydene of person.
In one embodiment of this specification, L2 and L3 are same or different to each other, be each independently Direct Bonding or
Arlydene.
In one embodiment of this specification, L2 and L3 are same or different to each other, be each independently Direct Bonding or
Phenylene.
In one embodiment of this specification, R1 to R3 is same or different to each other, and is each independently hydrogen or deuterium.
In one embodiment of this specification, R1 to R3 is hydrogen.
In one embodiment of this specification, the compound indicated by above-mentioned chemical formula 1 is in following structural formula
Either one or two of.
Compound involved by one embodiment of this specification can be manufactured by aftermentioned manufacturing method.
[Reaction equation 1]
1) manufacture of chemical formula 1-c
By the chloro- 2- iodobenzenes 200.00g (1.00eq) of the bromo- 1- of 4-, (2- nitrobenzophenones) boric acid ((2-nitrophenyl)
Boronic acid) 105.78g (1.0eq), 7.31g (0.01eq) Pd (PPh3)4It is dissolved in after being stirred in the THF of 1.5L, it will
The K of 113.78g (1.3eq)2CO3It is dissolved in the water of 400ml and adds, it is stirred at 60 DEG C.After 2 hours, reaction terminates
When, after detaching organic layer, is depressurized, eliminate solvent.Product is dissolved completely in CHCl3Afterwards, it is washed with water, by solution
It is concentrated under reduced pressure into 50% or so, ethyl alcohol is added, removes crystallization, is filtered.Then it is purified using column chromatography.It obtains
The chemical formula 1-c (yield 87%) of 171.30g.[M+H]=310
2) manufacture of chemical formula 1-b
The chemical formula 1-c of 171.30g (1.0eq) is dissolved in the triethyl phosphite (P (OEt) of 500mL3) in, reflux
Stirring.At the end of being reacted after 3 hours, vacuum decompression removes 50% or so solvent, and crystallization is removed in cooling.It is completely dissolved after filtering
It in ethyl acetate, is then washed with water, solution decompression is concentrated into 70% or so, crystallization is removed in cooling, filters.Then column is utilized
Chromatography is purified.The chemical formula 1-b (yield 81%) of 124.48g is obtained.[M+H]=279
3) manufacture of chemical formula 1-a
By the iodobenzene of chemical formula 1-b, 100.10g (1.1eq) of 124.48g (1.0eq), 25.49g (0.3eq) CuI,
The K of 12.34g (2.0eq)2CO3It is added to the two of 1LIn alkane, the ethylenediamine of 30ml is added dropwise, is stirred at 80 DEG C.Reaction terminates
When, after being cooled to room temperature, after the whole solvents of solution decompression removal dissolved with product, it is dissolved completely in CHCl3, it is washed with water
It washs, is depressurized again, remove solvent, it is purified using column chromatography.Chemical formula 1-a (the yields of 123.56g are obtained
78%).[M+H]=355
4) manufacture of chemical formula 1A
In the chemical formula 1-a of 123.55g (1.0eq), by the Pd (t-Bu of 0.75g (0.005eq)3P)2,126.05g
The K of (2.00eq)2CO3It is added in the dimethylacetylamide (Dimethylacetamide) of 800mL, return stirring.After 3 hours
Water, removal crystallization, filtering are imported to reactant.It after the solid of filtering is dissolved completely in ethyl acetate, is washed with water, will dissolve
There is the solution decompression of product to concentrate, is purified using column chromatography.The chemical formula 1A (yield 83%) of 86.90g is obtained.
[M]=275
In addition, this specification provides the above-mentioned organic electroluminescent device for including compound.
The embodiment of the application organic electroluminescent device is provided comprising:First electrode, with above-mentioned the
One electrode contraposition and the second electrode that has and has 1 layer or more between above-mentioned first electrode and above-mentioned second electrode
Organic matter layer, 1 layer of above-mentioned heterocyclic compound contained above in above-mentioned organic matter layer.
In this specification, when pointing out that a certain component is located at another component "upper", not only comprising a certain component and separately
The case where one component contacts further includes the case where there are other components between two components.
In this specification, when pointing out a certain inscape of certain a part of "comprising", as long as no especially opposite record,
Then mean that other inscapes can be further included, rather than other inscapes are excluded.
The organic matter layer of the organic electroluminescent device of the application can be formed by single layer structure, can also be by being laminated with 2
Layer or more the multilayered structure of organic matter layer formed.For example, the representative example of the organic electroluminescent device as the present invention
Son, organic electroluminescent device can have comprising hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electronics note
Enter the structure as organic matter layer such as layer.But it's not limited to that for the structure of organic electroluminescent device, can include less
Organic layer.
In the embodiment of the application, the thickness of above-mentioned organic matter layer isExtremely
In the embodiment of the application, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes above-mentioned heterocycle
Compound.
In the embodiment of the application, above-mentioned organic matter layer includes hole injection layer or hole transmission layer, above-mentioned sky
Cave implanted layer or hole transmission layer include above-mentioned heterocyclic compound.
In the embodiment of the application, above-mentioned organic matter layer includes electron transfer layer or electron injecting layer, above-mentioned electricity
Sub- transport layer or electron injecting layer include above-mentioned heterocyclic compound.
In the embodiment of the application, above-mentioned organic matter layer includes electronic barrier layer or hole blocking layer, above-mentioned electricity
Sub- barrier layer or hole blocking layer include above-mentioned heterocyclic compound.
In the embodiment of the application, above-mentioned organic matter layer includes electronic barrier layer, and above-mentioned electronic barrier layer includes
Above-mentioned heterocyclic compound.
In the embodiment of the application, above-mentioned organic electroluminescent device includes:First electrode and above-mentioned first electricity
The extremely opposed and second electrode that has and has luminescent layer between above-mentioned first electrode and above-mentioned second electrode, has
2 layers or more between above-mentioned luminescent layer and above-mentioned first electrode or between above-mentioned luminescent layer and above-mentioned second electrode organic
Nitride layer, at least one layer in above-mentioned 2 layers or more of organic matter layer include above-mentioned heterocyclic compound.
In the embodiment of the application, above-mentioned 2 layers or more of organic matter layer can select electron transfer layer, electronics
Implanted layer, the layer for being carried out at the same time electron-transport and electron injection and 2 or more in hole blocking layer.
In the embodiment of the application, above-mentioned organic matter layer includes 2 layers or more of electron transfer layer, above-mentioned 2 layers
At least one layer in above electron transfer layer includes above-mentioned heterocyclic compound.Specifically, in an implementation of this specification
In mode, above compound may be embodied in 1 in above-mentioned 2 layers or more of electron transfer layer layer, can also be separately contained in 2
Layer or more electron transfer layer in.
In addition, in the embodiment of the application, when above-mentioned heterocyclic compound is separately contained in above-mentioned 2 layers or more
In the case of in electron transfer layer, the other materials other than above-mentioned heterocyclic compound can be the same or different from each other.
In the embodiment of the application, above-mentioned organic matter layer is in addition to the organic matter layer containing above-mentioned heterocyclic compound
In addition, also include hole injection layer or hole transmission layer, it is described containing hole injection layer or hole transmission layer include containing fragrant amino,
The compound of carbazyl or benzo carbazole base.
In another embodiment, organic electroluminescent device can be sequentially laminated on substrate anode, 1 layer with
On organic matter layer and cathode structure (standard type (normal type)) organic electroluminescent device.
In another embodiment, organic electroluminescent device can be sequentially laminated on substrate cathode, 1 layer with
On organic matter layer and anode reverse structure (inversion type (inverted type)) organic electroluminescent device.
For example, the structure of the organic electroluminescent device involved by the embodiment of the application is illustrated in Fig. 1 and 2.
Fig. 1 instantiate be sequentially laminated with substrate 1, anode 2, luminescent layer 3, cathode 4 organic electroluminescent device structure.
In this configuration, above-mentioned heterocyclic compound may be embodied in above-mentioned luminescent layer 3.
Fig. 2, which is instantiated, is sequentially laminated with substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 3, electronics biography
The structure of the organic electroluminescent device of defeated layer 7 and cathode 4.In this configuration, above-mentioned heterocyclic compound may be embodied in
It states in 1 layer or more in hole injection layer 5, hole transmission layer 6, luminescent layer 3 and electron transfer layer 7.
In this configuration, above-mentioned heterocyclic compound may be embodied in above-mentioned hole injection layer, hole transmission layer, luminescent layer
In 1 layer or more in electron transfer layer.
In the organic electroluminescent device of the application, the compound of 1 layer of the application contained above in organic matter layer is wrapped
Containing above compound, in addition to this, material well-known in the art and method can be utilized to manufacture.
In the case that above-mentioned organic electroluminescent device includes multiple organic matter layers, above-mentioned organic matter layer can be by identical
Substance or different substances formed.
In the organic electroluminescent device of the application, 1 layer of above-mentioned heterocyclic compound contained above in organic matter layer, i.e., by
The heterocyclic compound that above-mentioned chemical formula 1 indicates can utilize material well-known in the art and method to manufacture in addition to this.
For example, the organic electroluminescent device of the application can be by stacking gradually first electrode, organic matter on substrate
Layer and second electrode manufacture.At this moment, it can manufacture as follows:Utilize sputtering method (sputtering) or electron-beam vapor deposition method (e-
Beam evaporation) etc PVD (physical vapor deposition (physical Vapor Deposition)) method, in substrate
Upper evaporation metal or conductive metal oxide or their alloy and form anode, then on the anode formed packet
Then organic matter layer containing hole injection layer, hole transmission layer, luminescent layer and electron transfer layer is deposited available on organic matter layer
Make the substance of cathode to manufacture.In addition to this approach, can also on substrate successively evaporation cathode substance, organic matter layer,
Anode material and manufacture organic electroluminescent device.
In addition, the compound about above-mentioned chemical formula 1 can not only utilize true when manufacturing organic electroluminescent device
Empty vapour deposition method can also form organic matter layer using solution coating method.Here, so-called solution coating method refers to spin-coating method, leaching
Coating, knife coating, ink jet printing method, silk screen print method, spray-on process, rolling method etc., but not limited to this.
In addition to this approach, can also on substrate successively evaporation cathode substance, organic matter layer, anode material and make
Make organic electroluminescent device (International Patent Application Publication the 2003/012890th).But manufacturing method is not limited to
This.
In the embodiment of the application, above-mentioned first electrode is anode, and above-mentioned second electrode is cathode.
In another embodiment, above-mentioned first electrode is cathode, and above-mentioned second electrode is anode.
As above-mentioned anode material, generally for enabling hole successfully to be injected to organic matter layer, preferably work function
Big substance.As can be used for the present invention anode material concrete example, have the metals such as vanadium, chromium, copper, zinc, gold or they
Alloy;The metal oxides such as zinc oxide, indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO);ZnO:Al or SnO2:Sb etc.
The combination of metal and oxide;Poly- (3 methyl thiophene), Ju [3,4- (ethylidene -1,2- dioxies) Sai Fen ](PEDOT), polypyrrole
With the electroconductive polymers such as polyaniline etc., but not limited to this.
As above-mentioned cathode substance, generally for making electronics easily be injected to organic matter layer, preferably work function is small
Substance.As the concrete example of cathode substance, have the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or it
Alloy;LiF/Al or LiO2Multilayered structures substance such as/Al etc., it is not limited to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, as hole injecting material, preferably followingization
Close object:Have the ability of transporting holes, there is hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole inject effect, prevent in luminescent layer generated exciton to be migrated to electron injecting layer or electron injection material, and thin
Film Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO) (the highest occupied of hole injecting material
Molecular orbital)) between the work function and the HOMO of surrounding organic matter layer of anode material.It is injected as hole
The concrete example of substance has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, six nitriles, six azepine benzophenanthrene system
It is organic matter, anthraquinone and polyaniline and poly- thiophene that organic matter, quinacridone (quinacridone), which are organic matter, (perylene),
Pheno system electroconductive polymer etc., but not limited to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as
Hole transporting material is the substance that can be received the hole from anode or hole injection layer and transfer them to luminescent layer, right
The substance that the mobility in hole is big is suitable.As concrete example, have the organic matter of aryl amine system, electroconductive polymer and
The block copolymer etc. of conjugate moiety and non-conjugated portion is existed simultaneously, it is not limited to this.
It is that can receive hole and electronics respectively from hole transmission layer and electron transfer layer and make as above-mentioned luminescent substance
They in conjunction with and send out the substance of the light of visible light region, preferably for the high substance of the quantum efficiency of fluorescence or phosphorescence.As
Concrete example has 8- Hydroxy-quinolin aluminum complexes (Alq3);Carbazole based compound;Two polystyrene-based (dimerized
Styryl) compound;BAlq;10- hydroxy benzo quinoline metal compounds;BenzoAzoles, benzothiazole and benzimidazole system
Close object;Poly- (to phenylene vinylidene) (PPV) is macromolecule;Loop coil (spiro) compound;Polyfluorene, rubrene etc., but not
It is only limitted to this.
Above-mentioned luminescent layer can include material of main part and dopant material.Material of main part has aromatic fused ring derivative or contains
Heterocyclic compound etc..Specifically, as aromatic fused ring derivative, there are anthracene derivant, pyrene derivatives, naphthalene derivatives and five
Benzene derivative, phenanthrene compound, fluoranthene compound etc. have compound, dibenzofuran derivative, ladder as nitrogen-containing heterocgcies
Type furan compound Pyrimidine derivatives etc., but not limited to this.
Above-mentioned electron transfer layer is from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer, as electronics
Transport materials are can to receive electronics well from cathode and transfer them to the substance of luminescent layer, big to the mobility of electronics
Substance be suitable.As concrete example, there are the Al complexs of 8-hydroxyquinoline, includes Alq3Complex, organic free radical
Compound, hydroxyl brass-metal complex etc., it is not limited to this.Electron transfer layer can be as used in the prior art
As be used together with the cathode substance of any desired.In particular, the example of suitable cathode substance is with low work function
And with aluminium layer or the common substance of silver layer.Specifically, be caesium, barium, calcium, ytterbium and samarium, in the case of each substance, and aluminium
Layer or silver layer accompany.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound:With transmission electronics
Ability, there is electron injection effect from cathode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent
Only generated exciton is migrated to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone,
Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles,
Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous 5 membered ring derivatives etc., but simultaneously
It is not limited to this.
As above-mentioned metal complex, have 8-hydroxyquinoline lithium, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinoline) copper,
It is bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double
(10- Qiang Jibenbings [h]Quinoline) beryllium, bis- (10- Qiang Jibenbings [h]Quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides, bis- (2-
Methyl -8- quinoline) (o-cresol) gallium, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (beta naphthals)
Gallium etc., but not limited to this.
Above-mentioned hole blocking layer is the layer for preventing hole from reaching cathode, can generally utilize item identical with hole injection layer
Part is formed.Specifically, havingOxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, aluminum complex
(aluminum complex) etc., but not limited to this.
Embodiment
In the following, enumerating embodiment in order to illustrate this specification and being described in detail.But according to this specification
Embodiment can be deformed into various forms, should not be construed as scope of the present application and be defined in embodiment as detailed below.This
The embodiment of application provides to more completely illustrate this specification to those skilled in the art.
1. compound 1 of synthesis example
By the N- (4- (9,9- dimethyl -9H- fluorenes -2- bases) of chemical formula 1A, 14.44g (1.1eq) of 10.0g (1.0eq)
Phenyl) biphenyl -4- amine, 6.98g (2.0eq) NaOtBu, 0.09g (0.005eq) Pd (t-Bu3P)2It is dissolved in the two of 90ml
In toluene (Xylene), return stirring.It is depressurized at the end of being reacted after 1 hour, eliminates solvent.Then it is dissolved completely in
CHCl3In, it is washed with water, is depressurized again, eliminate 50% or so solvent.Again at reflux, acetic acid is added
Ethyl ester removes crystallization, cooled and filtered.It is carried out column chromatography and has obtained the compound 1 (yield 79%) of 17.24g.[M+
H]=677
2. compound 2 of synthesis example
By N- (xenyl -4- bases) -9,9- dimethyl-of chemical formula 1A, 17.48g (1.1eq) of 10.0g (1.0eq)
9H- fluorenyl -3- amine, 6.98g (2.0eq) NaOtBu, 0.09g (0.005eq) Pd (t-Bu3P)2It is dissolved in the diformazan of 90ml
In benzene (Xylene), return stirring.It is depressurized at the end of being reacted after 1 hour, eliminates solvent.Then it is dissolved completely in
CHCl3In, it is washed with water, is depressurized again, eliminate 50% or so solvent.Again at reflux, acetic acid is added
Ethyl ester removes crystallization, cooled and filtered.It is carried out column chromatography and has obtained the compound 2 (yield 81%) of 19.91g.[M]
=600
3. compound 3 of synthesis example
By N- (4- (the Er Benbing [ of chemical formula 1A, 14.44g (1.1eq) of 10.0g (1.0eq);b,d]Furans -4- bases) benzene
Base) xenyl -4- amine, 6.98g (2.0eq) NaOtBu, 0.09g (0.005eq) Pd (t-Bu3P)2It is dissolved in the two of 90ml
Toluene (Xylene), return stirring.It is depressurized at the end of reaction response after 1 hour, eliminates solvent.Then it is dissolved completely in
CHCl3In, it is washed with water, is depressurized again, eliminate 50% or so solvent.Again at reflux, acetic acid is added
Ethyl ester removes crystallization, cooled and filtered.It is carried out column chromatography and has obtained the compound 3 (yield 77%) of 16.80g.[M+
H]=651
4. compound 4 of synthesis example
By N (4- (the Er Benbing [ of chemical formula 1A, 16.44g (1.1eq) of 10.0g (1.0eq);b,d]Thiene-3-yl) benzene
Base) xenyl -4- amine, 6.98g (2.0eq) NaOtBu, 0.09g (0.005eq) Pd (t-Bu3P)2It is dissolved in the two of 90ml
In toluene (Xylene), return stirring.It is depressurized at the end of being reacted after 1 hour, eliminates solvent.Then it is dissolved completely in
CHCl3In, it is washed with water, is depressurized again, eliminate 50% or so solvent.Again at reflux, acetic acid is added
Ethyl ester removes crystallization, cooled and filtered.Its column chromatography the compound 4 (yield 83%) of 19.62g has been obtained into.[M]=666
5. compound 5 of synthesis example
By 4- (xenyl -4- bases (4- (the Er Benbing [ of chemical formula 1A, 21.88g (1.1eq) of 10.0g (1.0eq);b,d]
Thiophene -4- bases) phenyl) amino) phenylboric acid, the 15.43g (2.0eq) being dissolved in the water of 40ml K3PO4,0.09g
Pd (the t-Bu of (0.005eq)3P)2It is dissolved in the two of 90mlIn alkane, return stirring.At the end of being reacted after 1 hour, subtracted
Pressure, eliminates solvent.Then it is dissolved completely in CHCl3In, be washed with water, depressurized again, eliminate 50% or so it is molten
Agent.Again at reflux, ethyl acetate is added, removes crystallization, cooled and filtered.Its column chromatography 21.85g has been obtained into
Compound 5 (yield 81%).[M+H]=743
6. compound 6 of synthesis example
By 4- (xenyl -4- bases (4- (the 9,9- dimethyl-of chemical formula 1A, 22.28g (1.1eq) of 10.0g (1.0eq)
9H- fluorenes -2- bases) phenyl) amino) phenylboric acid, the 15.43g (2.0eq) being dissolved in the water of 40ml K3PO4,0.09g
Pd (the t-Bu of (0.005eq)3P)2It is dissolved in the two of 90mlIn alkane, return stirring.Subtracted at the end of being reacted after 1 hour
Pressure, eliminates solvent.Then it is dissolved completely in CHCl3In, be washed with water, depressurized again, eliminate 50% or so it is molten
Agent.Again at reflux, ethyl acetate is added, removes crystallization, cooled and filtered.Its column chromatography 23.24g has been obtained into
Compound 6 (yield 85%).[M]=752
7. compound 7 of synthesis example
By the 4- ((4- (9,9- dimethyl -9H- fluorenes -2- bases) of chemical formula 1A, 25.24g (1.1eq) of 10.0g (1.0eq)
Phenyl) (triphenylene -2- bases) amino) phenylboric acid, the 15.43g (2.0eq) being dissolved in the water of 40ml K3PO4,0.09g
Pd (the t-Bu of (0.005eq)3P)2It is dissolved in the two of 90mlIn alkane, return stirring.At the end of being reacted after 1 hour, subtracted
Pressure, eliminates solvent.Then it is dissolved completely in CHCl3In, be washed with water, depressurized again, eliminate 50% or so it is molten
Agent.Again at reflux, ethyl acetate (Ethyl acetate) is added, removes crystallization, cooled and filtered.By its column layer
It analyses and has obtained the compound 7 (yield 86%) of 25.83g.[M]=826
8. compound 8 of synthesis example
By 4- ((4- (the Er Benbing [ of chemical formula 1A, 24.84g (1.1eq) of 10.0g (1.0eq);b,d]Thiophene -4- bases)
Phenyl) (triphenylene -2- bases) amino) phenylboric acid, the 15.43g (2.0eq) being dissolved in the water of 40ml K3PO4,0.09g
Pd (the t-Bu of (0.005eq)3P)2It is dissolved in the two of 90mlIn alkane, return stirring.At the end of being reacted after 1 hour, subtracted
Pressure, eliminates solvent.Then it is dissolved completely in CHCl3In, be washed with water, depressurized again, eliminate 50% or so it is molten
Agent.Again at reflux, ethyl acetate is added, removes crystallization, cooled and filtered.Its column chromatography 24.63g has been obtained into
Compound 8 (yield 83%).[M+H]=817
<Bi compare Li >
It will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide (indium tin oxide))
It is put into the distilled water dissolved with detergent, utilizes ultrasonic washing.At this moment, as detergent, Fei Xier companies have been used
The product of (Fischer Co.) has used the filtering manufactured using Millipore Corp. (Millipore Co.) as distilled water
Device (Filter) filter 2 times after distilled water.After ITO is washed 30 minutes, using distilled water repeatedly 2 times and carry out 10 minutes it is super
Sonic washing.After distilling water washing, with the solvent progress ultrasonic washing of isopropanol, acetone, methanol and after drying, conveying
To plasma washing machine.In addition, cleaning aforesaid substrate after five minutes using oxygen plasma, vacuum steaming is delivered the substrate to
Plating machine.On the ito transparent electrode prepared in this way withThickness thermal vacuum vapor deposition following chemical formula six nitriles, six azepine
Benzophenanthrene (hexaazatriphenylene;HAT-CN) hole injection layer is formed.On above-mentioned hole injection layer, by conduct
Following compounds of the substance of transporting holesIt carries out vacuum evaporation and forms hole transmission layer.Then, exist
On above-mentioned hole transmission layer, withThe following compound EB of film thickness vacuum evaporation and form electronic barrier layer.Then,
On above-mentioned electronic barrier layer, withFilm thickness by following BH and BD with 25:1 weight ratio carry out vacuum evaporation and
Form luminescent layer.On above-mentioned luminescent layer, by above compound ET and above compound LiQ (8-hydroxyquinoline lithiums
(Lithium Quinolate)) with 1:1 weight ratio carries out vacuum evaporation, thus withThickness form electronics note
Enter and transport layer.In above-mentioned electron injection and transport layer successively by lithium fluoride (LiF) withThickness, by aluminium with
Thickness is deposited, so as to form cathode.In above process, the evaporation rate of organic matter maintainsIt is cloudy
The lithium fluoride of pole maintainsEvaporation rate, aluminium maintainEvaporation rate, vapor deposition when vacuum degree maintain
2×10-7~5 × 10-6Torr, to make organic electroluminescent device.
<Experimental example 1-1>
In above-mentioned comparative example, compound EB is replaced using above compound 1, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-2>
In above-mentioned comparative example, compound EB is replaced using above compound 2, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-3>
In above-mentioned comparative example, compound EB is replaced using above compound 3, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-4>
In above-mentioned comparative example, compound EB is replaced using above compound 4, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-5>
In above-mentioned comparative example, compound EB is replaced using above compound 5, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-6>
In above-mentioned comparative example, compound EB is replaced using above compound 6, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-7>
In above-mentioned comparative example, compound EB is replaced using above compound 7, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Experimental example 1-8>
In above-mentioned comparative example, compound EB is replaced using above compound 8, in addition to this, by identical with comparative example
Method has made organic electroluminescent device.
<Comparative example 1>
In above-mentioned comparative example, using above-mentioned H-1 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
<Comparative example 2>
In above-mentioned comparative example, using above-mentioned H-2 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
<Comparative example 3>
In above-mentioned comparative example, using above-mentioned H-3 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
<Comparative example 4>
In above-mentioned comparative example, using above-mentioned H-4 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
<Comparative example 5>
In above-mentioned comparative example, using above-mentioned H-5 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
<Comparative example 6>
In above-mentioned comparative example, using above-mentioned H-6 compound replace compound EB, in addition to this, by with above-mentioned comparison
The identical method of example has made organic electroluminescent device.
When applying electric current to the organic illuminating element made by experimental example 1-1 to 1-8 and comparative example 1 to 6, electricity is measured
Pressure, current density, brightness, chromaticity coordinates and service life the results are shown in Xia Shu [Table 1].T95 indicates brightness from initial stage brightness
(650nit) is reduced to the time needed for 95%.
[Table 1]
As shown in Table 1 above, organic electroluminescent device the compound of the present invention made as electronic barrier layer
In the case of, excellent characteristic is shown in terms of the efficiency of organic electroluminescent device, driving voltage and/or stability.
The core of the present application and the organic electroluminescence for manufacturing the compound of comparative example 1 to 6 as electronic barrier layer
Light-emitting component is compared, and shows low-voltage, high efficiency and the characteristic of long-life.Voltage reduces 5~10% or so, and efficiency increases
10% or more.By existing indoles and [3,2,1-jk]The direction of No. 2, No. 10, No. 11 upper amine connected of carbazole is to such as originally
The connection of direction (No. 1) more than the such steric hindrance of compound of invention, and when being connected to the direction of conjugated fracture, show efficiency
Rise, voltage is reduced, the characteristic of long-life, it is known that core indoles and [3,2,1-jk]The stability of carbazole itself also improves.Separately
Outside, since the part that core is connect with amine is more bent, also have the advantages that in terms of thermal stability excellent.
Claims (12)
1. a kind of heterocyclic compound indicated by following chemical formula 1:
Chemical formula 1
In the chemical formula 1, Ar1 and Ar2 are same or different to each other, be each independently substituted or unsubstituted aryl or
Substituted or unsubstituted heterocycle,
L1 to L3 is same or different to each other, be each independently Direct Bonding, substituted or unsubstituted arlydene or substitution or
The heterocycle of unsubstituted divalent,
R1 to R3 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted monosilane
Base, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heterocycle,
The integer that the integer that a is 0 to 2, b and c are 0 to 4, substituent group when a to c is 2 or more in bracket are identical or different.
2. heterocyclic compound according to claim 1, which is characterized in that the Ar1 and Ar2 are same or different to each other, respectively
From the aryl or substituted or unsubstituted carbon atom number 2 to 30 for independently being substituted or unsubstituted carbon atom number 6 to 30
Heterocycle.
3. heterocyclic compound according to claim 1, wherein the Ar1 and Ar2 are same or different to each other, respectively independent
Ground is to be substituted by phenyl or unsubstituted phenyl, be substituted by phenyl or unsubstituted xenyl, be substituted by phenyl or unsubstituted
Terphenyl is substituted by phenyl or unsubstituted triphenylene, is substituted by phenyl or unsubstituted dimethyl fluorenyl, is taken by phenyl
Generation or unsubstituted dibenzofuran group are substituted by phenyl or unsubstituted dibenzothiophene or are substituted by phenyl or not
Substituted carbazyl.
4. heterocyclic compound according to claim 1, wherein the L1 be Direct Bonding, phenylene, divalent dibenzo
The dimethyl fluorenyl of furyl, the dibenzo thiophenyl of divalent, the fluorenyl of divalent or divalent.
5. heterocyclic compound according to claim 1, wherein the L2 and L3 are same or different to each other, each independently
For Direct Bonding or phenylene.
6. heterocyclic compound according to claim 1, wherein the R1 to R3 is hydrogen.
7. heterocyclic compound according to claim 1, wherein the compound of the chemical formula 1 is selected from following structural formula:
8. a kind of organic electroluminescent device comprising:First electrode, it is opposed with the first electrode and have second
Electrode and has 1 layer or more of organic matter layer between the first electrode and the second electrode, the organic matter layer
In at least one layer include heterocyclic compound described in any one of claim 1 to 7.
9. organic electroluminescent device according to claim 8, wherein the organic matter layer includes luminescent layer, the hair
Photosphere includes the heterocyclic compound.
10. organic electroluminescent device according to claim 8, wherein the organic matter layer include hole injection layer or
Hole transmission layer, the hole injection layer or hole transmission layer include the heterocyclic compound.
11. organic electroluminescent device according to claim 8, wherein the organic matter layer include electron transfer layer or
Electron injecting layer, the electron transfer layer or electron injecting layer include the heterocyclic compound.
12. organic electroluminescent device according to claim 8, wherein the organic matter layer includes electronic barrier layer, institute
It includes the heterocyclic compound to state electronic barrier layer.
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| US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
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| US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
| TW202208594A (en) * | 2020-05-27 | 2022-03-01 | 德商麥克專利有限公司 | Materials for electronic devices |
| KR102212689B1 (en) * | 2020-08-25 | 2021-02-05 | 주식회사 이엘엠 | Composition For Capping Layer of Organic Light Emitting Diode and Organic Light Emitting Diode Having The Same |
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| CN111004243B (en) * | 2019-12-02 | 2021-08-03 | 武汉华星光电半导体显示技术有限公司 | Indolo [3,2,1-jk ] carbazole derivative, organic electroluminescent device, and display panel |
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| Publication number | Publication date |
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| JP6705586B2 (en) | 2020-06-03 |
| JP2019507737A (en) | 2019-03-22 |
| KR101919223B1 (en) | 2018-11-15 |
| WO2017142310A1 (en) | 2017-08-24 |
| KR20170095755A (en) | 2017-08-23 |
| CN108699069B (en) | 2021-06-01 |
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