CN113461627B - Compound, electroluminescent device and application thereof - Google Patents
Compound, electroluminescent device and application thereof Download PDFInfo
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- CN113461627B CN113461627B CN202010239279.4A CN202010239279A CN113461627B CN 113461627 B CN113461627 B CN 113461627B CN 202010239279 A CN202010239279 A CN 202010239279A CN 113461627 B CN113461627 B CN 113461627B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- -1 triarylamine compound Chemical class 0.000 claims abstract description 75
- 239000000463 material Substances 0.000 claims abstract description 56
- 125000001424 substituent group Chemical group 0.000 claims abstract description 52
- 239000010410 layer Substances 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 36
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 31
- 229910052805 deuterium Inorganic materials 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000006467 substitution reaction Methods 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims description 11
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 11
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 11
- 150000004696 coordination complex Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 18
- 230000006872 improvement Effects 0.000 abstract description 5
- 238000013461 design Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 125000005259 triarylamine group Chemical group 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000003111 delayed effect Effects 0.000 description 10
- 239000012634 fragment Substances 0.000 description 10
- 125000005549 heteroarylene group Chemical group 0.000 description 9
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- DLGZLIXYVSQGOX-UHFFFAOYSA-N 4-[8-[4-(4-tert-butylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]furan-2-carboxamide Chemical compound C1CN(C(C)(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=COC(C(N)=O)=C1 DLGZLIXYVSQGOX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 3
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 3
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 3
- 235000019798 tripotassium phosphate Nutrition 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001616 biphenylenes Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
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- YRPIGRRBBMFFBE-UHFFFAOYSA-N 1-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=CC=CC=C12 YRPIGRRBBMFFBE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
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Abstract
The invention provides a compound, an electroluminescent device and application thereof, wherein the compound has a structure shown in a formula I, is a novel triarylamine compound which is connected by an azaaromatic ring and contains naphthalene or azanaphthalene structural units, and can be used as a charge transport material or a main body material in the electroluminescent device. The compound realizes the improvement of the structure through the design of the molecular structure and the substituent, can reduce the driving voltage of the electroluminescent device, improve the luminous efficiency, remarkably prolong the service life of the device and enable the electroluminescent device to fully meet the requirements of commercial application.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a compound, an electroluminescent device and application thereof.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices, among others. OLEDs are becoming increasingly popular for their unique advantageous properties of wide color gamut, almost infinitely high contrast, extremely high response speed, flexibility, energy conservation, etc.
In 1987, tang and Van Slyke of Islaman kodak reported a two-layer organic electroluminescent device comprising a hole transport layer of arylamine, and electron transport and light emitting layers of tris-8-hydroxyquinoline-aluminum; once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern OLEDs. Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.
OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and Van Slyke invention is a fluorescent OLED that uses only singlet light emission, and the triplet states generated in the device are wasted through non-radiative decay channels. Therefore, the Internal Quantum Efficiency (IQE) of the fluorescent OLED is only 25%, so that the commercialization of the fluorescent OLED is hindered by the limitation. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters, enabling harvesting of singlet and triplet states, achieving 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds; these emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.
Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.
The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, the field of OLED devices is also expected to have more saturated emission spectra, lower driving voltages, higher efficiency and longer device lifetime.
In order to improve the performance of electroluminescent devices, research and development of host materials matched with phosphorescent materials in the light-emitting layer is very important. For example, CN108117525A discloses a general structure ofSpecific examples of the compounds of (2) are +.>This application notes the unique properties of triazine-linked triarylamine structured compounds, but does not disclose the use of naphthalene or naphthyridine building blocks in triarylamine building blocks, nor does it disclose the effect that triarylamine fragments can bring about by introducing naphthalene or naphthyridine building blocks.
Although many electroluminescent materials comprising triazine structural segments have been developed, the conventional materials still have various disadvantages such as high energy consumption, low luminous efficiency, short working life, and the like. Thus, the development of higher performance electroluminescent materials and devices remains an important topic of research in the art.
Disclosure of Invention
In order to develop higher performance electroluminescent materials, it is an object of the present invention to provide a compound having a structure as shown in formula I:
in the formula I, ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and combinations thereof;
In the formula I, L 1 Selected from the group consisting of: substituted or unsubstituted C6-C18 arylene, substituted or unsubstituted heteroarylene having 5 to 13 ring atoms, and combinations thereof;
in the formula I, L 2 Selected from the group consisting of: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene, and combinations thereof;
and when L 1 L is selected from substituted or unsubstituted phenylene 2 Selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, and combinations thereof;
in the formula I, L 3 Selected from the group consisting of: a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C3 to C30 heteroarylene, and combinations thereof;
in the formula I, X 1 、X 2 、X 3 Each independently selected from N or C-R x And X is 1 、X 2 、X 3 At least 2 of which are N;
in the formula I, Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from C, C-R y Or N;
R x 、R y and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Adjacent substituents R y Can optionally be linked to form a ring.
In the compound provided by the invention, an azaaromatic ring structure (such as triazine and the like) is connected with a triarylamine fragment through an aromatic bridging structure, and a naphthalene or azanaphthalene condensed structural unit is introduced into the triarylamine fragment, so that the electroluminescent material obtained has unexpected improvement in performance, especially in the aspect of device service life, and a bipolar main body material with excellent performance can be obtained.
It is a second object of the present invention to provide an electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a compound according to one of the objects.
It is a further object of the present invention to provide an electroluminescent device as defined in the second object for use in an electronic apparatus, an electronic component module, a display device or a lighting device.
It is a fourth object of the present invention to provide a compound formulation comprising a compound according to one of the objects.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a compound, which connects an aza-aromatic ring structure with a triarylamine fragment through an aromatic bridging structure, introduces a condensed structural unit into the triarylamine fragment, and obtains a bipolar compound with excellent performance, and can be used as a main body material or a charge transport material of an electroluminescent device. The compound realizes the improvement of the structure through the design of the molecular structure and the substituent, so that the compound can be used as a main material of a luminescent layer to reduce the driving voltage of an electroluminescent device, improve the luminous efficiency, remarkably prolong the service life of the device and fully meet the requirements of commercial application.
Drawings
FIG. 1 is a schematic diagram of an organic light emitting device containing a compound and a compound formulation provided by the present invention;
FIG. 2 is a schematic diagram of another organic light emitting device containing the compounds and compound formulations provided herein.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
OLEDs can be fabricated on a variety of substrates, such as glass, plastic or metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent No. 7279704B2 at columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5844363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6303238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. patent nos. 5703436 and 5707745, which are incorporated by reference in their entirety, which include composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. patent No. 6097147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent No. 7968146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in other organic electronic devices as listed above.
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. Where a first layer is described as "disposed" on a second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (iric) rate is sufficiently fast to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.
Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe S-T ). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe S-T . These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-includes straight and branched alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbon in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.
Cycloalkyl-as used herein, includes cyclic alkyl. Preferred cycloalkyl groups are cycloalkyl groups containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, cycloalkyl groups may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, covers both straight chain and branched alkene groups. Preferred alkenyl groups are alkenyl groups containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, covers both straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl.
Heterocyclyl or heterocycle-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated that may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothiophene pyridine, thienodipyridine, benzothiophene bipyridine, benzoselenophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-1, 3-aza-borane, 1-borane, 4-borane, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples of alkyl groups and preferred examples are the same as described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy groups. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.
Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include phenoxy and diphenoxy.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, aralkyl groups may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-chlorophenyl, 1-isopropyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl.
The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, refers to any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted aralkyl having 1 to 20 carbon atoms, unsubstituted alkoxy having 6 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, and substituted aryl having 3 to 30 carbon atoms, and the combination thereof.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, poly (heavy) substitution refers to a range of substitution inclusive of di (heavy) substitution up to the maximum available substitution. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where adjacent substituents can optionally be joined to form a ring, the ring formed may be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
The expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
furthermore, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
in one embodiment, the present invention provides a compound having a structure as shown in formula I:
in the formula I, ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and combinations thereof;
in the formula I, L 1 Selected from the group consisting of: substituted or unsubstituted C6-C18 arylene, substituted or unsubstituted heteroarylene having 5 to 13 ring atoms, and combinations thereof;
in the formula I, L 2 Selected from the group consisting of: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene, and combinations thereof; wherein "L 2 Is a single bond "means naphthyl in formula IOr the fused structure of the naphthyridinyl is directly linked to N;
and when L 1 L is selected from substituted or unsubstituted phenylene 2 Selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, and combinations thereof;
in the formula I, L 3 Selected from the group consisting of: a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C3 to C30 heteroarylene, and combinations thereof;
in the formula I, X 1 、X 2 、X 3 Each independently selected from N or C-R x And X is 1 、X 2 、X 3 At least 2 of them are N, e.g. X 1 、X 2 、X 3 Wherein 2 or 3 of them are N;
in the formula I, Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from C, C-R y Or N;
R x 、R y and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Adjacent substituents R y Can optionally be linked to form a ring.
Herein, adjacent substituents R y Can optionally be linked to form a ring, intended to mean that when multiple substituents R are present y When adjacent substituents R y Can be connected to form a ring. Obviously, theseNone of the substituents may be joined to form a ring.
In a preferred embodiment, the X 1 、X 2 、X 3 Are all N.
In one embodiment, the Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from C or C-R y 。
In a preferred embodiment, the Y 1 Is C, Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from C-R y 。
In a preferred embodiment, the Y 2 Is C, Y 1 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from C-R y 。
In one embodiment, the Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 At least 1 of them is N, for example, 1, 2, 3 or 4, etc.
In a preferred embodiment, the Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 1 of them is N.
In a preferred embodiment, the Y 5 、Y 6 、Y 7 、Y 8 1 of them is N.
In one embodiment, the L 1 Selected from the group consisting of: substituted or unsubstituted C6-C12 arylene, substituted or unsubstituted heteroarylene having 5 to 13 ring atoms, and combinations thereof.
In a preferred embodiment, the L 1 Selected from the group consisting of: substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted Substituted or unsubstituted thienylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothienylene, and combinations thereof.
In a preferred embodiment, the L 1 Selected from substituted or unsubstituted biphenylene groups.
In one embodiment, the L 1 Selected from the group consisting of the following structures:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R L1 Substitution, said R L1 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In a preferred embodiment, the R L1 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, and combinations thereof.
In a preferred embodiment, the R L1 And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluorine, phenyl, and combinations thereof.
In one embodiment, the L 2 Selected from the group consisting of the following structures:
a single bond,/>
Wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R L2 Substitution, said R L2 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In a preferred embodiment, the R L2 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, and combinations thereof.
In a preferred embodiment, the R L2 And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluorine, phenyl, and combinations thereof.
In one embodiment, the L 3 Selected from the group consisting of the following structures:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R L3 Substitution, said R L3 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In a preferred embodiment, the R L3 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, and combinations thereof.
In a preferred embodiment, the R L3 And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluorine, phenyl, and combinations thereof.
In one embodiment, the Ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of the following structures:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R Ar3 Substitution;
R Ar 、R Ar1 、R Ar2 、R Ar3 and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In a preferred embodiment, the R Ar 、R Ar1 、R Ar2 、R Ar3 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, and combinations thereof.
In a preferred embodiment, the R Ar 、R Ar1 、R Ar2 、R Ar3 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, phenyl, and combinations thereof.
In one embodiment, the compound has a structure as shown in formula II:
in formula II, R y1 Represents mono-, poly-or unsubstituted;
in the formula II, X 1 、X 2 、X 3 、Ar 1 、Ar 2 、Ar 3 、L 2 、L 3 Each independently having the same defined ranges as in formula I;
in the formula II, L 4 Selected from the group consisting of the following structures:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R L4 Substitution;
the R is y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In a preferred embodiment, the R y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, and combinations thereof.
In a preferred embodiment, the R y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluorine, phenyl, and combinations thereof.
In a preferred embodiment, the compound has a structure as shown in formula II-1, formula II-2 or formula II-3:
in the formula II-1, formula II-2 or formula II-3, X 1 、X 2 、X 3 、Ar 1 、Ar 2 、Ar 3 、L 4 、R y1 Each independently has the same defined range as in formula II.
In a preferred embodiment, the compounds are selected from the group consisting of compounds 1 to 864, wherein compounds 1 to 184 are ordered in sequence according to the numerical numbers, the specific structure of which is given in claim 11.
In a preferred embodiment, the hydrogen in the compounds 1 to 864 can be optionally substituted with deuterium, fluorine or cyano.
In one embodiment, the present invention provides an electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a compound as described above.
In one embodiment, the organic layer is a light emitting layer and the compound is a host material of the light emitting layer.
In a specific embodiment, the light emitting layer further comprises at least one phosphorescent light emitting material, the phosphorescent light emitting material being a metal complex comprising at least one ligand comprising any one of the following structures:
wherein R is a 、R b 、R c Each independently represents mono-, poly-or unsubstituted;
X b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, N-R N1 And CR (CR) C1 R C2 ；
X c 、X d And is selected identically or differently on each occurrence from the group consisting ofGroup: o, S, se and N-R N2 ；
R a 、R b 、R c 、R N1 、R N2 、R C1 、R C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
In the structure of the ligand, adjacent substituents can optionally be linked to form a ring.
In this embodiment, adjacent substituents can optionally be linked to form a ring, intended to mean between adjacent substituents, e.g., two R a Between two R b Between two R c Between, substituent R a And R is b Between, substituent R a And R is c Between, substituent R b And R is c Between, substituent R a And R is N1 Between, substituent R b And R is N1 Between, substituent R a And R is C1 Between, substituent R a And R is C2 Between, substituent R b And R is C1 Between, substituent R b And R is C2 Between, substituent R a And R is N2 Between, substituent R b And R is N2 Between, and R C1 And R is C2 In between, any one or more of these substituent groups may be linked to form a ring. It will be apparent to those skilled in the art that none of these substituents may be linked to form a ring.
In a specific embodiment, the metal of the metal complex is selected from Cu, ag, au, ru, rh, pd, pt, os or Ir.
In a preferred embodiment, the metal of the metal complex is selected from Ir, pt or Os.
In a preferred embodiment, the metal of the metal complex is Ir.
In one embodiment, the metal complex has the structural formula Ir (L a )(L b )(L c ) The L is a 、L b 、L c Each independently selected from any of the ligands described above.
In a preferred embodiment, the phosphorescent material is selected from the group consisting of the following structures:
wherein X is f And is selected identically or differently on each occurrence from the group consisting of: o, S, se, N-R N3 And CR (CR) C3 R C4 ；
X e Is selected identically or differently on each occurrence from N or C-R d ；
R a 、R b Each independently represents mono-, poly-or unsubstituted;
R a 、R b 、R c 、R d 、R N3 、R C3 、R C4 and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyanoIsocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one embodiment, the invention provides the use of an electroluminescent device as described above in an electronic apparatus, an electronic component module, a display device or a lighting device.
In one embodiment, the present invention provides a compound formulation comprising a compound as described above.
The compounds provided by the invention can be prepared by the synthesis methods disclosed in the prior art, and are not listed one by one for the sake of brevity. Illustratively, the synthetic route for the compounds is as follows:
the compounds having the structure shown in formula I may be formed from organometallic reagents (e.g., boric acid, borate, grignard, tin, silicon, etc.) of halogenated aza-aromatic ring (e.g., triazine) fragments and triarylamine fragments linked by a transition metal catalyzed C-C coupling reaction. For example, a haloazaaromatic ring (e.g., triazine) segment and a boric acid (ester) segment of a triarylamine are formed by bell wood coupling under the catalysis of a transition metal (e.g., palladium), as illustrated by the following formula:
or as indicated by the following formula:
the compounds having the structure shown in formula I may also be formed from a haloazaaromatic ring (e.g., triazine) segment linked to a secondary amine segment by a transition metal (e.g., palladium or copper) catalyzed C-N coupling reaction, as illustrated, for example, by the following formula:
Combined with other materials
The materials described herein for specific layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the materials disclosed herein may be used in combination with a variety of light emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art, including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bay's sublimator, etc., in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, suzhou, a lifetime test system, or an ellipsometer manufactured by Beijing mass extension, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
Material synthesis examples:
the preparation method of the compound of the present invention is not limited, and is typically, but not limited to, exemplified by the following compounds, the synthetic routes and preparation methods thereof are as follows:
Synthesis example 1
This example provides a compound 97, having the following specific structure:
(1) Synthesis of intermediate 97-A
4-aminobiphenyl (3.0 g,17.5 mmol), 2, 3-dibromonaphthalene (5.0 g,17.5 mmol), palladium acetate Pd (OAc) 2 (200 mg,0.9 mmol), 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos, 1036mg,1.8 mmol), sodium t-butoxide (tBuona, 3.4g,35.2 mmol) was added to a 500mL three-necked flask, and then 100mL Toluene (tolene) was added, and the reaction solution was heated to 80℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with petroleum ether PE/dichloromethane dcm=4:1 ratio, to give intermediate 97-a (4.2 g, 82.5% yield) as a white solid.
(2) Synthesis of intermediate 97-B
Intermediate 97-A (4.0 g,10.69 mmol), phenylboronic acid (2.0 g,16.02 mmol), tetrakis triphenylphosphine palladium Pd (PPh) 3 ) 4 (570 mg,0.5 mmol) and potassium carbonate (2.9 g,21.1 mmol) were added to a 500mL three-necked flask, followed by150mL of 1, 4-Dioxane (Dioxane) and 50mL of distilled water were added. The reaction was heated to 90 ℃ overnight under nitrogen. After the reaction was completed, cooled, ethyl acetate was added, washed with water, and the organic phase was dried by spin-drying, and purified by silica gel chromatography, eluting with petroleum ether PE/ethyl acetate ea=5:1, to give intermediate 97-B (3.3 g, yield 84%) as a yellow solid.
(3) Synthesis of intermediate 97-C
Intermediate 97-B (3.3 g,9.0 mmol), p-bromoiodobenzene (5.0 g,18.0 mmol), palladium acetate Pd (OAc) 2 (151 mg,0.67 mmol), xantphos (771 mg,1.34 mmol), tBuONa (2.6 g,27.0 mmol) were added to a 500mL three-necked flask, then 100mL toluene was added, and the reaction was heated to 70℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=5:1 ratio, to give intermediate 97-C (3.6 g, 76% yield) as a white solid.
(4) Synthesis of intermediate 97-D
Intermediate 97-C (3.5 g,6.6 mmol), pinacol biborate (2.9 g,11.4 mmol), palladium acetate (85 mg,0.38 mmol), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (sphos, 312mg,0.76 mmol), potassium acetate (KOAc, 1.5g,15.2 mmol) were placed in a 250mL three-necked flask, 80mL of 1, 4-dioxane was added, and the mixture was heated to 105℃under nitrogen and refluxed overnight. After the reaction was completed, it was cooled, ethyl acetate was added, washed with water, and the organic phase was dried by spin-drying, followed by purification by silica gel chromatography using PE/ea=5:1 as eluent to give intermediate 97-D (2.8 g, yield 73.9%) as a white solid.
(5) Synthesis of Compound 97
Intermediate 97-D (2.8 g,4.8 mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (2.4 g,6.2 mmol), palladium acetate (92 mg,0.41 mmol), sphos (336 mg,0.82 mmol), tripotassium phosphate (4.4 g,16.50 mmol) were added to a 250mL three-necked flask, followed by addition of a mixed solvent (Toluene/ethanol EtOH/water=40/10/10 mL) and reaction at 100℃under nitrogen blanket. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, purified by silica gel chromatography, eluting with PE/dcm=4:1, and the product was collected and recrystallized from toluene to give compound 97 (3.1 g, yield 85.6%) as a white solid. The product was identified as the target product and had a molecular weight of 754.
Synthesis example 2
This example provides a compound 183 having the following structure:
(1) Synthesis of intermediate 183-A
O-aminobiphenyl (3.5 g,19.4 mmol), 1- (4-bromophenyl) naphthalene (5.0 g,17.6 mmol), palladium acetate (201 mg,0.9 mmol), xantphos (1036 mg,1.8 mmol), sodium t-butoxide (3.4 g,35.2 mmol) were added to a 500mL three-necked flask, 100mL toluene was added, and the reaction mixture was heated to 80℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=4:1 ratio, to give intermediate 183-a (5.4 g, 82.5% yield) as a white solid.
(2) Synthesis of intermediate 183-B
Intermediate 183-A (5.0 g,13.5 mmol), p-bromoiodobenzene (5.7 g,20.2 mmol), palladium acetate (151 mg,0.67 mmol), xantphos (771 mg,1.34 mmol), sodium t-butoxide (2.6 g,27.0 mmol) were added to a 500mL three-necked flask, then 150mL toluene was added, and the reaction was heated to 70℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=5:1 ratio, to give intermediate 183-B (4.4 g, yield 62%) as a white solid.
(3) Synthesis of intermediate 183-C
Intermediate 183-B (4.0 g,7.6 mmol), pinacol biborate (2.9 g,11.4 mmol), palladium acetate (85 mg,0.38 mmol), sphos (312 mg,0.76 mmol), potassium acetate (1.5 g,15.2 mmol) were placed in a 250mL three-necked flask, 80mL of 1, 4-dioxane was added, and the mixture was heated to 105℃under nitrogen and refluxed overnight. After the reaction was completed, cooled, ethyl acetate was added, washed with water, and the organic phase was spin-dried, purified by silica gel chromatography using PE/ea=5:1 as eluent, and the solid was collected and slurried with n-hexane to give intermediate 183-C (3.6 g, yield 82.6%) as a white solid.
(4) Synthesis of Compound 183
Intermediate 183-C (3.6 g,6.28 mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (3.2 g,8.25 mmol), palladium acetate (92 mg,0.41 mmol), sphos (336 mg,0.82 mmol), tripotassium phosphate (4.4 g,16.50 mmol) were added to a 250mL three-necked flask, followed by addition of a mixed solvent (toluene/ethanol/water=40/10/10 mL) and the mixture was heated to 100 ℃ under nitrogen protection overnight. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=4:1, to give compound 183 (3.5 g, 73.9% yield) as a white solid. The product was identified as the target product and had a molecular weight of 754.
Synthesis example 3
This example provides a compound 195 having the following structure:
(1) Synthesis of intermediate 195-A
O-aminobiphenyl (3.5 g,19.4 mmol), 2- (4-bromophenyl) naphthalene (5.0 g,17.6 mmol), palladium acetate (201 mg,0.9 mmol), xantphos (1036 mg,1.8 mmol), sodium t-butoxide (3.4 g,35.2 mmol) were added to a 500mL three-necked flask, 100mL toluene was added, and the reaction mixture was heated to 80℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=4:1 ratio, to give intermediate 195-a (5.0 g, 69.6% yield) as a white solid.
(2) Synthesis of intermediate 195-B
Intermediate 195-A (5.0 g,13.5 mmol), p-bromoiodobenzene (5.7 g,20.2 mmol), palladium acetate (151 mg,0.67 mmol), xantphos (771 mg,1.34 mmol), sodium t-butoxide (2.6 g,27.0 mmol) were added to a 500mL three-necked flask, followed by 150mL toluene, and the reaction was heated to 70℃overnight under nitrogen. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=5:1 ratio, to give intermediate 195-B (4.1 g, 53% yield) as a white solid.
(3) Synthesis of intermediate 195-C
Intermediate 195-B (4.0 g,7.6 mmol), pinacol biborate (2.9 g,11.4 mmol), palladium acetate (85 mg,0.38 mmol), sphos (312 mg,0.76 mmol), potassium acetate (1.5 g,15.2 mmol) were placed in a 250mL three-necked flask, 80mL of 1,4 dioxane was added, and the mixture was heated to 105℃under nitrogen and refluxed overnight. After the reaction was completed, cooled, ethyl acetate was added, washed with water, and the organic phase was spin-dried, purified by silica gel chromatography using PE/ea=5:1 as eluent, and the solid was collected and slurried with n-hexane to give intermediate 195-C (2.9 g, yield 66.4%) as a white solid.
(4) Synthesis of Compound 195
Intermediate 195-C (2.9 g,5.2 mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (3.2 g,8.25 mmol), palladium acetate (92 mg,0.41 mmol), sphos (336 mg,0.82 mmol), tripotassium phosphate (4.4 g,16.50 mmol) were added to a 250mL three-necked flask, followed by addition of a mixed solvent (toluene/ethanol/water=40/10/10 mL) and the mixture was heated to 100 ℃ under nitrogen protection overnight. After the reaction was completed, the organic phase was cooled, washed with water, and dried by spin-drying, and purified by silica gel chromatography, eluting with PE/dcm=4:1, to give compound 195 (2.5 g, yield 63.7%) as a white solid. The product was identified as the target product and had a molecular weight of 754.
Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.
Device example 1
The embodiment of the present device provides an electroluminescent device, which sequentially includes: substrate, ITO anode 120nm, hole injection layerHole transport layer->Electron blocking layer->Luminous layer->Hole blocking layer->Electron transport layer->Electron injection layer->Cathode (aluminum)>The preparation method comprises the following steps:
(1) Cleaning a glass substrate having an Indium Tin Oxide (ITO) anode of 120nm thickness, then treating with UV ozone and oxygen plasma, after the treatment, drying the substrate in a glove box filled with nitrogen gas to remove moisture, then mounting the substrate on a substrate holder and loading into a vacuum chamber, then placing the organic layer designated below in a vacuum of about 10 -8 In the case of a palletSequentially evaporating on an ITO anode through thermal vacuum evaporation:
(2) The compound HI is used as a Hole Injection Layer (HIL);
(3) Evaporating a compound HT on the hole injection layer to serve as a Hole Transport Layer (HTL);
(4) Evaporating a compound H1 on the hole transport layer to serve as an Electron Blocking Layer (EBL);
(5) Vapor-depositing a light-emitting layer on the electron blocking layer, co-vapor-depositing a light-emitting layer (EML) using the compound 97 provided in synthetic example 1 of the present invention as a host and the compound RD (2% by weight) as a dopant;
(6) Evaporating a compound H2 on the light-emitting layer to serve as a Hole Blocking Layer (HBL);
(7) Co-evaporating a compound ET and 8-hydroxyquinoline-lithium (Liq) as an Electron Transport Layer (ETL) on the HBL;
(8) Depositing Liq as an Electron Injection Layer (EIL) on the electron transport layer, and depositing 120nm Al as a cathode;
the device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
Device example 2
Device example 2 differs from device example 1 only in that compound 97 in step (5) was replaced with compound 183 provided in synthetic example 2.
Device example 3
Device example 3 differs from device example 1 only in that compound 97 in step (5) was replaced with compound 195 provided in synthesis example 3.
Device comparative example 1
Device ratio 1 differs from device example 1 only in that compound 97 in step (5) was replaced with compound H3.
Device comparative example 2
Device ratio 2 differs from device example 1 only in that compound 97 in step (5) was replaced with compound H4.
Device comparative example 3
Device ratio 3 differs from device example 1 only in that compound 97 in step (5) was replaced with compound H5.
The detailed device layer structure and thickness are shown in table 1 below. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
Table 1 device structures of device examples and comparative examples
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The material structure used in the device is as follows:
the HI of the compound isCompound HT is->Compound H1 is->Compound RD->Compound H2 is->Compound ET is->Compound H3 isCompound H4 is->Compound H5 isThe present invention provides a compound which is useful for the treatment of cancer,
at 15mA/cm 2 The device drive voltage (V), current efficiency (CE, in Cd/A), external Quantum Efficiency (EQE) and CIE color coordinates are measured below; at 80mA/cm 2 The lifetime LT97 (hr) of the device to 97% of the initial brightness was measured at constant current. The above test data are shown in table 2.
Table 2 device data
| Device numbering | Driving voltage (V) | CE(Cd/A) | EQE(％) | LT97(hr) | CIE(x,y) |
| Example 1 | 4.45 | 20.3 | 24.5 | 40.0 | (0.686,0.313) |
| Example 2 | 4.71 | 21.8 | 25.8 | 15.0 | (0.685,0.314) |
| Example 3 | 4.73 | 21.4 | 25.5 | 18.0 | (0.685,0.313) |
| Comparative example 1 | 5.36 | 20.7 | 24.5 | 2.3 | (0.684,0.314) |
| Comparative example 2 | 5.15 | 20.2 | 23.8 | 0.1 | (0.684,0.313) |
| Comparative example 3 | 4.85 | 20.6 | 24.3 | 0.9 | (0.684,0.314) |
As shown in Table 2, the constant current was 15mA/cm 2 In the following, the CIE coordinates of examples 1 to 3 of the inventive devices were substantially identical to those of comparative examples 1 to 3. The driving voltages of examples 1 to 3 were lowered compared with each of the comparative examples, and the effect of the lowering of example 1 was most remarkable, and the driving voltages were lowered by 0.91V, 0.70V and 0.40V compared with comparative examples 1 to 3, respectively. In terms of current efficiency, both examples and comparative examples can reach higher levels, with example 1 being leveled with each comparative example, and comparative example 1, which is more efficient than example 2 and example 3, still has 5.3% and 3.4% improvement. Meanwhile, the external quantum efficiency of example 2 and example 3 was also improved by 5.3% and 4.1%, respectively, as compared with comparative example 1. In terms of service life of the device, the three embodiments are far higher than the comparative examples, and can meet the requirements of commercial application.
From the test results, the electroluminescent device containing the compound has high luminous efficiency and long service life. Compared with the main compound used in the comparative example, the compound provided by the invention introduces a naphthalene structure at the triarylamine end, uses biphenyl as a connection between the triarylamine and triazine, adds phenylene between naphthalene and the nitrogen atom of the arylamine as an aromatic bridging structure and adds substituent groups to the naphthalene for modification. From the measurement result of the device, the compound provided by the invention can reduce the driving voltage of the device through structural improvement, improve the luminous efficiency, effectively improve the defect of shorter service life of the device, and has high commercial development potential.
The applicant states that the present invention is illustrated by the above examples as a compound of the invention, electroluminescent device and its use, but the invention is not limited to, i.e. does not mean that the invention has to be carried out in dependence of, the above process steps. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (19)
1. A compound, wherein the compound has a structure according to formula II-1 or formula II-3:
wherein Ar is 1 、Ar 2 、Ar 3 Each independently selected from the following groups:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R Ar3 Substitution;
R Ar3 and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, unsubstituted C1-C20 alkyl;
X 1 、X 2 、X 3 are all N;
L 4 selected from the group consisting of the following structures:
wherein represents the attachment site of the group;
the hydrogen energy in the above radicals is optionally replaced by at least 1R L4 Substitution;
wherein R is y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, unsubstituted C1-C20 alkyl, unsubstituted C6-C12 aryl.
2. The compound of claim 1, wherein R Ar3 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen.
3. The compound of claim 1, wherein R Ar3 And are selected identically or differently on each occurrence from unsubstituted C1-C20 alkyl groups.
4. The compound of claim 1, wherein R Ar3 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl.
5. The compound of claim 1, wherein R y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, unsubstituted C6 to C12 aryl.
6. The compound of claim 1, wherein R y1 Selected from unsubstituted C6-C12 aryl groups at each occurrence.
7. The compound of claim 1, wherein R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen.
8. The compound of claim 1, wherein R y1 、R L4 And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluorine, phenyl.
9. The compound of claim 1, wherein the compound is selected from the group consisting of:
10. an electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising the compound of any one of claims 1-9.
11. The electroluminescent device of claim 10, wherein the organic layer is a light-emitting layer and the compound is a host material for the light-emitting layer.
12. The electroluminescent device of claim 11, wherein the light-emitting layer further comprises at least one phosphorescent light-emitting material that is a metal complex comprising at least one ligand comprising any one of the following structures:
wherein R is a 、R b 、R c Each independently represents mono-, poly-or unsubstituted;
X b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, N-R N1 And CR (CR) C1 R C2 ；
X c 、X d And is selected identically or differently on each occurrence from the group consisting of: o, S, se and N-R N2 ；
R a 、R b 、R c 、R N1 、R N2 、R C1 、R C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine A base, and combinations thereof;
in the structure of the ligand, adjacent substituents can optionally be linked to form a ring.
13. The electroluminescent device of claim 12, wherein the metal of the metal complex is selected from Cu, ag, au, ru, rh, pd, pt, os or Ir.
14. The electroluminescent device of claim 12, wherein the metal of the metal complex is Ir, pt or Os.
15. The electroluminescent device of claim 12, wherein the metal of the metal complex is Ir.
16. The electroluminescent device of claim 12, wherein the metal complex has the formula Ir (L a )(L b )(L c ) The L is a 、L b 、L c Each independently selected from any of the ligands described above.
17. The electroluminescent device of claim 16, wherein the phosphorescent light emitting material is selected from the group consisting of:
wherein X is f And is selected identically or differently on each occurrence from the group consisting of: o, S, se, N-R N3 And CR (CR) C3 R C4 ；
X e Is selected identically or differently on each occurrence from N or C-R d ；
R a 、R b Each independently represents mono-, poly-or unsubstituted;
R a 、R b 、R c 、R d 、R N3 、R C3 、R C4 and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C0-C20 amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
18. Use of an electroluminescent device as claimed in any one of claims 10 to 17 in an electronic apparatus, an electronic component module, a display device or a lighting device.
19. A compound formulation comprising a compound according to any one of claims 1 to 9.
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