CN113527316A - Electroluminescent material and device - Google Patents
Electroluminescent material and device Download PDFInfo
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- CN113527316A CN113527316A CN202010285016.7A CN202010285016A CN113527316A CN 113527316 A CN113527316 A CN 113527316A CN 202010285016 A CN202010285016 A CN 202010285016A CN 113527316 A CN113527316 A CN 113527316A
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- 239000000463 material Substances 0.000 title claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 238000009472 formulation Methods 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 313
- 125000001424 substituent group Chemical group 0.000 claims description 130
- -1 cyano, isocyano, mercapto, sulfinyl Chemical group 0.000 claims description 96
- 239000010410 layer Substances 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 37
- 229910052805 deuterium Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 20
- 125000005104 aryl silyl group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 20
- 238000006467 substitution reaction Methods 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004185 ester group Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 13
- 150000004696 coordination complex Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 21
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 13
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 12
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 239000007787 solid Substances 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000477 aza group Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- 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
- 239000005711 Benzoic acid Substances 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical group 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000011161 development 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
- 238000000295 emission spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 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
- 239000007788 liquid Substances 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004433 nitrogen atom Chemical group 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
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000013086 organic photovoltaic Methods 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
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 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
- 230000002441 reversible effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical compound B1=CC=CN=C1 HWIATMHDQVGMFQ-UHFFFAOYSA-N 0.000 description 1
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- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical compound B1=CC=NC=C1 OBUDOIAYABJUHQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical group C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
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- 108091008695 photoreceptors Proteins 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
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Abstract
An electroluminescent material and device are disclosed. The electroluminescent material is a compound formed by bonding indole and pyrrole fused azamacrocycles, quinazoline, quinoxaline and similar structures on a specific ring, and can be used as a main body material in an electroluminescent device. The novel compounds can effectively improve the efficiency of the device, reduce the driving voltage of the device and provide better device performance. An electroluminescent device and compound formulation are also disclosed.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound in which indole and pyrrole fused azamacrocycles are bonded to quinazoline, quinoxaline and the like on a specific ring, and an organic electroluminescent device and a compound formulation comprising the same.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (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 plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise 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. Since OLEDs are a self-emissive solid state device, it offers 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 the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through 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 are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
US20180337340a1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, comprising an organic layer comprising one or more hosts, the first host of which is an organic optical compound having the structure:
However, there is still room for improvement in the currently reported host materials, and in order to meet the increasing demands of the industry, especially for the requirements of higher device efficiency, longer device lifetime, and lower driving voltage, the new materials still need to be further researched and developed.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing a series of compounds having indole and pyrrole fused azamacrocycles bonded to specific rings, quinazoline, quinoxaline and similar structures. The compounds are useful as host materials in organic electroluminescent devices. The novel compounds can effectively improve the efficiency of the device, reduce the driving voltage of the device and provide better device performance.
According to one embodiment of the invention, a compound is disclosed having the structure of H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy，Y5To Y8Each independently selected from N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of H-L-E;
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Selected from N or CR, the same or different at each occurrence,ring A, ring B and ring C, identically or differently on each occurrence, are selected from carbocyclic rings having from 5 to 18 carbon atoms, or heterocyclic rings having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy；Y5To Y8Each independently selected from N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
According to another embodiment of the invention, a compound formulation is also disclosed, comprising the compound having the structure of H-L-E.
According to another embodiment of the present invention, a display assembly is also disclosed, which comprises the electroluminescent device described in the above embodiment.
The novel compound with indole and pyrrole fused azamacrocyclic structure connecting quinazoline, quinoxaline and similar structures can be used as a main body material in an electroluminescent device. These novel compounds have an electron transport unit of quinazoline, quinoxaline and the like, and a hole transport unit having an indole and pyrrole fused azamacrocycle structure attached to a specific ring of the electron transport unit. The novel compound has excellent performance on the balance of hole and electron transmission, so that the efficiency of a device can be effectively improved, the driving voltage of the device can be reduced, and better device performance can be provided.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures 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, an emissive 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 described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA 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. 6,303,238 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 at 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. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may 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 via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some 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 sub-layers. 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, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against 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 a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various 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, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "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 "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the 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 retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-comprises both straight and branched chain 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 carbons 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 preferable.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. 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 atomsAn aryl group of 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 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-quaterphenyl.
Heterocyclyl or heterocyclic-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 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 which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 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, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, cinnolino, benzoselenophenopyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. 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 a phenoxy group and a biphenyloxy group.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 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-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable.
The term "aza" in aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in the corresponding aromatic moiety 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 may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in 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 amine, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amine, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more moieties selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on 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 to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom 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 it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. 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 carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as 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 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:
further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
according to one embodiment of the invention, a compound is disclosed having the structure of H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy，Y5To Y8Each independently selected from N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
In the present embodiment, "+" in formula 1 denotes a position where the structure represented by formula 1 is connected to L; "") in formula 2 represents a position where the structure represented by formula 2 is connected to the L.
In this context, the adjacent substituents R, RXCan optionally be linked to form a ring, intended to mean between adjacent substituents, e.g. between two R, two RXR and RXOptionally linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In this context, adjacent substituents RyCan optionally be linked to form a ring, intended to mean any two adjacent RyCan be connected to form a ring. Obviously, adjacent RyMay not be connected to form a ring.
According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, which occur identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.
According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, which occur identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
According to an embodiment of the present invention, wherein the H has a structure represented by formula 1-a:
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, X1To X10Selected, identically or differently, on each occurrence from N or CRx；
Wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted hetero having 1 to 20 carbon atomsAn alkyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
In the present embodiment, "+" in formula 1-a indicates a position where the structure represented by formula 1-a is connected to L.
In this example, the adjacent substituents R, RxCan optionally be linked to form a ring, is intended to mean that adjacent substituents R can optionally be linked to form a ring, is also intended to mean X1To X3In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X4To X6In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X7To X10In (B) an adjacent substituent RxCan optionally be linked to form a ring, and are also intended to represent adjacent substituents RxR and RxCan optionally be joined to form a ring, e.g. A1And X3And/or A3And X10And/or X6And X7Can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, RxOr may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents RxNor linked to form a ring, and/or adjacent substituents R and RxNor are they linked to form a ring.
According to one embodiment of the invention, wherein R,Rxeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, cyano, isocyano, mercapto, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
In this example, the adjacent substituents R, RxCan optionally be linked to form a ring, is intended to mean that adjacent substituents R can optionally be linked to form a ring, is also intended to mean X1To X3In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X4To X6In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X7To X10In (B) an adjacent substituent RxCan optionally be linked to form a ring, and are also intended to represent adjacent substituents RxR and RxCan optionally be joined to form a ring, e.g. A1And X3And/or A3And X10And/or X6And X7Can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, RxOr may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents RxNor linked to form a ring, and/or adjacent substituents R and RxNor are they linked to form a ring.
According to one embodiment of the present invention, wherein in said formula 1-a, R and RxAt least one of which is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to one embodiment of the present invention, wherein in said formula 1-a, R and RxAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.
According to an embodiment of the present invention, wherein in said formula 1-a, A1To A3Adjacent substituents R, X between1To X3Adjacent substituent R betweenx，X4To X6Adjacent substituent R betweenxAnd X7To X10Adjacent substituent R betweenxAt least one of these adjacent substituent groups is linked to form a ring.
In this embodiment, at least one of the adjacent substituent groups is linked to form a ring, which is intended to mean that for the adjacent substituent groups present in formula 1-a, for example, A1And A2Two adjacent substituents R, A2And A3Two adjacent substituents R, X1And X2Two adjacent substituents R inx，X2And X3Two adjacent substituents R inx，X4And X5Two adjacent substituents R inx，X5And X6Two adjacent substituents R inx，X7And X8Two adjacent substituents R inx，X8And X9Two adjacent substituents R inxAnd X9And X10Two adjacent substituents R inxAt least one of these substituent groups is linked to form a ring.
According to one embodiment of the invention, wherein H is selected from the group consisting of the following structures:
in this embodiment, "+" indicates the position where the structures represented by H-1 to H-130 are connected to L.
According to one embodiment of the present invention, wherein the hydrogen in the above structures of H-1 to H-130 can be partially or completely substituted with deuterium.
According to an embodiment of the present invention, wherein E is selected from a structure represented by any one of the group consisting of formula 2-a to formula 2-h:
wherein Y is selected from CR, the same or different at each occurrencey；
Wherein R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atomsSubstituted or unsubstituted aryloxy groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted amine groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
In this embodiment, "+" indicates the position where the structures represented by formulas 2-a to 2-h are connected to L.
In this example, adjacent substituents R can optionally be joined to form a ring, intended to mean when there are multiple R' syIn which any two adjacent R areyCan be linked to form a ring. Obviously, when there are a plurality of RyWhen the two or more rings are not connected, they may form a ring.
According to one embodiment of the invention, wherein, in the structures represented by formulae 2-a to 2-h, Y is selected, identically or differently on each occurrence, from CRy；RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano, and combinations thereof.
According to one embodiment of the invention, wherein, in the structures represented by formulae 2-a to 2-h, Y is selected, identically or differently on each occurrence, from CRy；RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, triphenylene, and combinations thereof.
According to an embodiment of the present invention, wherein in the structures represented by the formulas 2-a to 2-h, in the nitrogen heterocycleY in a six-membered ring is selected from CRyAnd said R isySelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the present invention, wherein in the structures represented by formulas 2-a to 2-h, Y in the aza six-membered ring is selected from CRyAnd said R isySelected from phenyl, biphenyl, naphthyl phenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, pyrimidyl or phenylpyridyl.
According to one embodiment of the invention, wherein E is selected from the group consisting of:
in this embodiment, "+" indicates the position where the structures denoted by E-1 to E-210 are connected to L.
According to one embodiment of the present invention, wherein hydrogen in the above structures of E-1 to E-210 can be partially or completely substituted with deuterium.
According to an embodiment of the invention, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof.
According to an embodiment of the invention, wherein L is selected from the group consisting of:
in this embodiment, "+" indicates the positions where the structures denoted by L-1 to L-26 are connected to the H and E, respectively.
According to one embodiment of the present invention, wherein hydrogen in the above structures of L-1 to L-26 can be partially or completely substituted with deuterium.
According to one embodiment of the present invention, wherein the compound having the structure of H-L-E is selected from the group consisting of compound 1 to compound 1000. The specific structures of the compounds 1 to 1000 are shown in claim 12.
According to one embodiment of the present invention, wherein hydrogen in the structures of compounds 1 to 1000 can be partially or completely substituted with deuterium.
According to an embodiment of the present invention, there is also disclosed an electroluminescent device, including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of H-L-E;
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy，Y5To Y8Each independently selected from N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20A cycloalkyl group having a ring carbon atom, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
In the present embodiment, "+" in formula 1 denotes a position where the structure represented by formula 1 is connected to L; "") in formula 2 represents a position where the structure represented by formula 2 is connected to the L.
According to one embodiment of the present invention, in the device, the organic layer is a light emitting layer, and the compound is a host material.
According to one embodiment of the invention, in the device, the light emitting layer further comprises at least one phosphorescent light emitting material.
According to one embodiment of the invention, in the device, the phosphorescent light emitting material is a metal complex comprising at least one ligand comprising the structure of any one of:
wherein the content of the first and second substances,
Ra，Rband RcIn each occurrence identically or differently, represents a single substitution, moreSubstituted, or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1，CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
In this example, adjacent substituents can optionally be joined to form a ring, intended to mean wherein adjacent groups of substituents, for example, two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1To R7Each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, in the device, wherein the phosphorescent light emitting material is an Ir, Pt or Os complex.
According to an embodiment of the present invention, the device, wherein the phosphorescent light emitting material is an Ir complex and has Ir (L)a)(Lb)(Lc) The structure of (1);
wherein L isa，LbAnd LcEach occurrence, identically or differently, is selected from any one of the group consisting of:
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
In this example, adjacent substituents can optionally be joined to form a ring, intended to mean wherein adjacent groups of substituents, for example, two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, the device, wherein the Ir complex is selected from the group consisting of:
wherein, XfEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN3And CRC3RC4；
Wherein, XeSelected from CR, identically or differently at each occurrencedOr N;
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Ra，Rb，Rc，Rd，RN3，RC3and RC4Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to another embodiment of the invention, a compound formulation is also disclosed, comprising a compound of the structure H-L-E. The specific structure of the compound is shown in any one of the embodiments.
According to another embodiment of the present invention, there is also disclosed a display assembly comprising the electroluminescent device of any of the above embodiments.
In combination with other materials
The materials described herein for use in particular 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 Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced 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 being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, light emitting dopants, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced 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.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek'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, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Materials synthesis example:
the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Compound 2
Step 1: synthesis of intermediate 1
2-bromo-3-chloronitrobenzene (100g, 425.5mmol), 2-aminophenylboronic acid pinacol ester (102g, 468.1mmol), tetratriphenylphosphine palladium (4.9g, 4.25mmol), potassium carbonate (115g, 852mmol), toluene (1000mL), water (200mL) and ethanol (200mL) were added to a three-necked flask under nitrogen and reacted at 100 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 4:1) gave intermediate 1(90g, yield: 85%) as a yellow oil.
Step 2: synthesis of intermediate 2
Intermediate 1(90g, 363mmol), acetonitrile (1000mL) were each placed in a three-necked flask and p-toluenesulfonic acid (193.2g, 1088mmol) was added portionwise at 0 ℃ and stirred for 30min, at which temperature an aqueous solution of a mixture of sodium nitrite (69g, 726mmol) and potassium iodide (150.6g, 907mmol) was slowly added dropwise. After the dropwise addition, the temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After completion of the reaction, a saturated aqueous solution of sodium thiosulfate was added dropwise to quench the reaction, the reaction mixture was concentrated and diluted with water, the mixed solution was extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and the mixture was subjected to column chromatography (PE/DCM ═ 10/1) to give intermediate 2(85g, yield: 65%) as a yellow solid.
And step 3: synthesis of intermediate 4
Intermediate 2(20g, 55.7mmol), intermediate 3(24.5g, 83.6mmol), tetrakistriphenylphosphine palladium (1.9g, 1.67mmol), potassium carbonate (15.4g, 111.4mmol), tetrahydrofuran (500mL), water (100mL), ethanol (100mL) were added to a three-necked flask under nitrogen and reacted at 70 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA ═ 4:1) to obtain intermediate 4(12g, yield: 55%) as a yellow solid.
And 4, step 4: synthesis of intermediate 5
Intermediate 4(12g, 30.15mmol), palladium acetate (338mg, 1.5mmol), tri-tert-butylphosphine (606mg, 3.0mmol), cesium carbonate (20g, 60.3mmol) and xylene (230mL) were added to a three-necked flask under nitrogen and reacted at 140 ℃ for 10 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 6:1) gave intermediate 5(9g, yield: 80%) as a yellow solid.
And 5: synthesis of intermediate 6
Intermediate 5(9g, 24.9mmol), triphenylphosphine (19.6g, 74.7mmol) and o-dichlorobenzene (o-DCB) (100mL) were added to a three-necked flask under nitrogen and reacted at 200 ℃ for 12 h. After completion of the reaction, the solvent was removed by concentration, and the crude product was separated by column chromatography to give intermediate 6(7g, yield: 85%) as a yellow solid.
Step 6: synthesis of Compound 2
Intermediate 7(3.2g, 10mmol), intermediate 6(3g, 9.1mmol), palladium acetate (101.9mg, 0.46mmol), tri-tert-butylphosphine tetrafluoroborate (266.8mg, 0.92mmol), sodium tert-butoxide (1.7g, 18.2mmol), xylene (100mL) were added to a three-necked flask under nitrogen and reacted at 140 ℃ overnight. After cooling to room temperature, distilled water was then added, the mixture was extracted with dichloromethane, the solvent was removed from the organic phase, and the residue was purified by column chromatography (PE/DCM ═ 1:1) to give compound 2(4.0g, yield: 73%) as a yellow solid, which was confirmed to be the objective product with a molecular weight of 610.2.
Synthesis example 2: synthesis of Compound 70
Intermediate 6(3g, 9.1mmol), intermediate 8(3.2g, 9.1mmol), palladium acetate (101.9mg, 0.46mmol), Sphos (369mg, 0.9mmol), cesium carbonate (5.9g, 60.3mmol), and xylene (100ml) were charged into a three-necked flask under nitrogen and reacted at 120 ℃ for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and the mixture was purified by column chromatography (PE/EA ═ 6:1) to obtain compound 70(2.9g, yield: 53%) as a yellow solid, which was confirmed to be the objective product having a molecular weight of 610.2.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Device embodiments
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 120nm thick, was cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of Torr
The rate of (a) was successively evaporated on the ITO anode by thermal vacuum. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of
Then, the compound 2 of the present invention as a host and the compound RD as a dopant were co-evaporated to be used as an emission layer (EML) with a thickness of
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron-transporting layer (ETL) with a thickness of
Finally, evaporation
8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited
As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device example 2
Device example 2 was carried out in the same manner as in device example 1 except that the compound 70 of the present invention was used as a host in place of the compound 2 of the present invention in the light-emitting layer (EML).
Device comparative example 1
Device comparative example 1 was the same as device example 1 except that compound a was used as a host in place of compound 2 of the present invention in the light emitting layer (EML).
The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
TABLE 1 device structures of device examples and comparative examples
The material structure used in the device is as follows:
table 2 shows the values at 15mA/cm2Under the conditions, measured Current Efficiency (CE), driving voltage (V), maximum wavelength (λ)max) And External Quantum Efficiency (EQE).
TABLE 2 device data
Discussion:
as shown in table 2, the maximum wavelength of the two examples and comparative examples remained substantially unchanged. At 15mA/cm2The EQE of example 1 measured at the current density was 23.8%, which is 5% higher than the EQE of comparative example 1 (18.8%), and the increase was 26.6%; CE (19) of example 1 was improved by 26.7% as compared with CE (15) of comparative example 1; the driving voltage (3.6V) of example 1 was reduced by 10% compared to the driving voltage (4.0) of comparative example 1; the EQE of the example 2 is 20.4% which is improved by 1.6% compared with the EQE (18.8%) of the comparative example 1, and the improvement range reaches 8.5%; CE (16) of example 2 was increased by 6.7% as compared with CE (15) of comparative example 1; the driving voltage (3.2V) of example 2 was reduced by 20% compared to the driving voltage (4.0V) of comparative example 1; the data show that the embodiment has more excellent device performance, namely, the compound of the invention which has a hole transport unit formed by fusing indole and pyrrole with azamacrocycle and is bonded with a specific ring of an electron transport unit of quinoxaline, quinazoline and similar structures has better stability of electron transport than the compound A bonded with 2-position of the quinazoline electron transport unit due to the special selection of the bonding position of the electron transport unit, and can enable the hole transport and the electron transport in a light-emitting layer to reach a more balanced state, so that the device can obtain lower driving voltage and simultaneously remarkably improve the efficiency of the device, and the device performance is remarkably improved. The unique advantages of the compounds of the present invention are demonstrated.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (20)
1. A compound having the structure H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy；Y5To Y8Each independently selected from N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atomsAn alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
2. The compound of claim 1, wherein each occurrence of ring a, ring B, and ring C, the same or different, is selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;
preferably, said ring a, ring B and ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
3. The compound of claim 2, wherein the H has a structure represented by formula 1-a:
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, X1To X10Selected, identically or differently, on each occurrence from N or CRx；
Wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
4. The compound of claim 3, wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, cyano, isocyano, mercapto, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
5. A compound according to claim 3 or 4, wherein R and RxToAt least one member selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
preferably, R and RxAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.
6. The compound of claim 3 or 4, wherein A is1To A3Adjacent substituents R, X between1To X3Adjacent substituent R betweenx，X4To X6Adjacent substituent R betweenxAnd X7To X10Adjacent substituent R betweenxAt least one of these adjacent substituent groups is linked to form a ring.
7. The compound of any one of claims 1 to 6, wherein said H is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
8. The compound of any one of claims 1 to 7, wherein E is selected from the structures represented by any one of the groups consisting of formula 2-a to formula 2-h:
wherein Y is selected from CR, the same or different at each occurrencey；
Wherein R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents RyCan optionally be linked to form a ring;
preferably, RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano, and combinations thereof;
more preferably, RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenylBiphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, triphenylene, and combinations thereof.
9. The compound of claim 8, wherein in the structures represented by formulas 2-a through 2-h, Y in the aza six-membered ring is selected from CRyAnd said R isySelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
preferably, said R isySelected from phenyl, biphenyl, naphthyl phenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, pyrimidyl or phenylpyridyl.
10. The compound of claim 8 or 9, wherein E is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
11. The compound of any one of claims 1 to 10, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof;
preferably, said L is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the structures of L-1 to L-26 above can be partially or completely substituted with deuterium.
12. The compound of claim 11, wherein the compound is selected from the group consisting of compounds 1 through 1000, the compounds 1 through 1000 having the structure of H-L-E, wherein H, L and E each correspond to a structure selected from the following table:
wherein, optionally, the hydrogen in the structure of the above compound can be partially or completely substituted with deuterium.
13. An electroluminescent device, comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of H-L-E;
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y4Any two of which are selected from N, the remaining two are each independently selected from CRy；Y5To Y8Are independently selected fromFrom N, C or CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
14. The electroluminescent device of claim 13, wherein the organic layer is a light emitting layer and the compound is a host material.
15. The electroluminescent device of claim 14 wherein said light-emitting layer further comprises at least one phosphorescent light-emitting material.
16. The electroluminescent device of claim 15, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand comprising the structure of any one of:
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
17. The electroluminescent device of claim 15, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand having the structure:
wherein R is1To R7Each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, wherein R1-R3At least one or two of which are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof;
more preferably, R1-R3At least two of which, on each occurrence, are selected, identically or differently, from substituted or unsubstituted C2-20 atomsA substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
18. An electroluminescent device as claimed in claim 16 or 17 wherein the phosphorescent light emitting material is an Ir, Pt or Os complex;
preferably, wherein the phosphorescent light-emitting material is an Ir complex and has Ir (L)a)(Lb)(Lc) The structure of (1);
wherein L isa，LbAnd LcA ligand selected from any of the above, identically or differently at each occurrence;
more preferably, wherein said Ir complex is selected from the group consisting of the following structures:
wherein, XfEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN3And CRC3RC4；
Wherein, XeSelected from CR, identically or differently at each occurrencedOr N;
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Ra，Rb，Rc，Rd，RN3，RC3and RC4Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkane having 3 to 20 ring carbon atomsA group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, sulfonyl, phosphino, and combinations thereof.
19. A compound formulation comprising a compound of any one of claims 1 to 12.
20. A display assembly comprising an electroluminescent device as claimed in any one of claims 13 to 18.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114437086A (en) * | 2022-02-24 | 2022-05-06 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound and preparation method and application thereof |
| CN114478551A (en) * | 2022-02-22 | 2022-05-13 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound, organic electroluminescent device and display device |
| CN114605413A (en) * | 2022-03-24 | 2022-06-10 | 上海八亿时空先进材料有限公司 | Carboline derivative and application thereof |
| CN115819427A (en) * | 2023-02-23 | 2023-03-21 | 夏禾科技(江苏)有限公司 | Synthetic method of benzo-quinoxaline-substituted indole and pyrrole fused azamacrocyclic compound |
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| KR20150077220A (en) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108391433A (en) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
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| KR20150077220A (en) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108391433A (en) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114478551A (en) * | 2022-02-22 | 2022-05-13 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound, organic electroluminescent device and display device |
| CN114478551B (en) * | 2022-02-22 | 2023-08-22 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound, organic electroluminescent device and display device |
| CN114437086A (en) * | 2022-02-24 | 2022-05-06 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound and preparation method and application thereof |
| CN114605413A (en) * | 2022-03-24 | 2022-06-10 | 上海八亿时空先进材料有限公司 | Carboline derivative and application thereof |
| CN114605413B (en) * | 2022-03-24 | 2024-03-19 | 上海八亿时空先进材料有限公司 | Carboline derivative and application thereof |
| CN115819427A (en) * | 2023-02-23 | 2023-03-21 | 夏禾科技(江苏)有限公司 | Synthetic method of benzo-quinoxaline-substituted indole and pyrrole fused azamacrocyclic compound |
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