CN116284032B - Organic compound, organic electroluminescent device and display device - Google Patents
Organic compound, organic electroluminescent device and display device Download PDFInfo
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- CN116284032B CN116284032B CN202310295965.7A CN202310295965A CN116284032B CN 116284032 B CN116284032 B CN 116284032B CN 202310295965 A CN202310295965 A CN 202310295965A CN 116284032 B CN116284032 B CN 116284032B
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- compound
- organic
- organic compound
- electroluminescent device
- organic electroluminescent
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 14
- 150000001875 compounds Chemical group 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 20
- -1 benzofluorenyl Chemical group 0.000 claims description 29
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 238000001308 synthesis method Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000004949 mass spectrometry Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 10
- 238000001514 detection method Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FJXPZWHFJUYIDO-UHFFFAOYSA-N CSC=1C(=CC2=CC=CC=C2C=1)B(O)O Chemical compound CSC=1C(=CC2=CC=CC=C2C=1)B(O)O FJXPZWHFJUYIDO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YVCYOVLYYZRNJC-UHFFFAOYSA-N (2-methoxyphenoxy)boronic acid Chemical compound COC1=CC=CC=C1OB(O)O YVCYOVLYYZRNJC-UHFFFAOYSA-N 0.000 description 1
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- QXBWTYBCNFKURT-UHFFFAOYSA-N (2-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=CC=C1B(O)O QXBWTYBCNFKURT-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical group C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- PPUZKAPOPPRMFE-UHFFFAOYSA-N 1,5-dibromo-2,4-difluorobenzene Chemical compound FC1=CC(F)=C(Br)C=C1Br PPUZKAPOPPRMFE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- DUZUYBOBIMKSPF-UHFFFAOYSA-N 2-naphthalen-2-ylsulfanylnaphthalene Chemical compound C1=CC=CC2=CC(SC=3C=C4C=CC=CC4=CC=3)=CC=C21 DUZUYBOBIMKSPF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical group C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- DUXKPIWSSPISSE-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C=C3C4=CC=C(B(O)O)C=C4OC3=CC2=C1 DUXKPIWSSPISSE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
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Abstract
The invention provides an organic compound, an organic electroluminescent device and a display device. The organic compound has a structure represented by the following formula BH-A. According to the invention, the compound structure is designed, and the compound is used as a main material of the luminous layer of the OLED device, so that the OLED device has lower driving voltage, higher current efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound, an organic electroluminescent device and a display device, and more particularly relates to a naphthobenzo aromatic compound, an organic electroluminescent device and a display device.
Background
Organic electroluminescence (OLED) display technology is a new generation of display technology based on electroluminescence, following CRT kinescope and LCD liquid crystal display. As a new generation of display technology, the display technology has the advantages of good display effect, low power consumption, high flexibility, ultra-thin performance and the like, and is widely applied to product screens of mobile phones, automobiles, intelligent wearing equipment and the like.
The OLED basic device structure comprises a cathode, an electron injection layer, an electron transport layer, an organic light emitting layer, a hole transport layer, a hole injection layer, an anode and a substrate. The color of the light emitted by the OLED depends on the type of organic molecules of the light emitting layer, and a color display is formed by placing several organic thin films on the same OLED. The brightness or intensity of the light depends on the properties of the luminescent material and the magnitude of the applied current, the greater the current, the higher the brightness of the light for the same OLED.
At present, various novel organic electroluminescent materials with excellent performance are developed successively, but with the rapid development of information technology, people also put forward new targets and requirements on the performance of an information display system, especially in the aspects of efficiency, service life, voltage and the like. Therefore, how to design a novel organic electroluminescent material to meet the use requirement of the novel organic electroluminescent material in high-performance OLED devices is an important subject for research by researchers in the field.
Disclosure of Invention
In view of the shortcomings of the prior art, an object of the present invention is to provide an organic compound, an organic electroluminescent device and a display device. According to the invention, the compound structure is designed, and the compound is used as a main material of the luminous layer of the OLED device, so that the OLED device has lower driving voltage, higher current efficiency and longer service life.
To achieve the purpose, the invention adopts the following technical scheme:
In a first aspect, the present invention provides an organic compound having the structure of formula BH-a:
wherein Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;
X is selected from O or S;
Ar 1 and Ar 2 are independently selected from at least one of-D, -F, -CN, C1-C10 alkyl, C1-C5 alkoxy or C6-C15 aryl;
the hydrogen atoms in the compound of formula BH-A may each independently be substituted with at least one of-D, -F, -CN, C1-C5 alkyl, C1-C5 alkoxy, C6-C20 aryl or C12-C20 heteroaryl.
According to the invention, through designing the structure of the naphtho-benzo heteroaromatic compound and controlling the hydrogen atom on the naphtho-benzo heteroaromatic compound to be substituted by a specific substituent, the naphtho-benzo heteroaromatic compound with a specific structure is obtained. The naphtho-benzo heteroaromatic compound provided by the invention can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
The compound of the invention adopts naphtho benzo heteroarylThe broken line represents the substituent connecting site) is used as a mother nucleus, has higher charge mobility and good stability, improves the efficiency and service life of an OLED device using the compound, and reduces the voltage.
In the present invention, ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6 to C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl groups and substituted or unsubstituted C12 to C20 (for example, C12, C14, C16, C18 or C20, etc.) heteroaryl groups.
The substituents described for Ar 1 and Ar 2 are each independently selected from at least one of-D, -F, -CN, C1-C10 alkyl (which may be, for example, methyl, ethyl, propyl, t-butyl, cyclopentyl or cyclohexyl, etc.), C1-C5 alkoxy (which may be, for example, methoxy, ethoxy or propoxy, etc.), or C6-C15 aryl (which may be, for example, phenyl or naphthyl, etc.).
The hydrogen atoms in the naphtho-benzo heteroaromatic compound of the formula BH-A can be each independently substituted by at least one of-D, -F, -CN, C1-C5 alkyl (for example, methyl, ethyl, propyl, etc.), C1-C5 alkoxy (for example, methoxy, ethoxy, propoxy, etc.), C6-C20 aryl (for example, phenyl, naphthyl, bivalent phenyl, etc.), or C12-C20 heteroaryl (for example, dibenzothienyl, dibenzofuranyl, etc.).
In the present invention, "D" represents a deuterium atom, and the same applies below.
The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention.
As a preferable embodiment of the present invention, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylene, fluoranthryl, hydrogenated benzoanthryl, indenofluorenyl, benzindene fluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, and benzonaphtofluorenyl.
As a preferable embodiment of the present invention, the C12-C20 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, dinaphthofuranyl and dinaphthothienyl.
As a preferable embodiment of the present invention, the C6-C20 is selected from any one of phenyl, biphenyl and naphthyl.
As a preferred embodiment of the present invention, each of Ar 1 and Ar 2 is independently selected from any one of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, naphthodibenzofuranyl, and naphthodibenzothienyl.
As a preferred embodiment of the present invention, the hydrogen atoms in the compound of formula BH-A may each independently be substituted by at least one of-D, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl.
As a preferred embodiment of the present invention, the compound of formula BH-a is selected from any one of the following compounds:
wherein X is selected from O or S.
Preferably, the compound of formula BH-a is selected from any one of the following compounds:
In a second aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
The material of the organic thin film layer comprises a naphtho-benzo-heteroaromatic compound according to the first aspect.
As a preferred embodiment of the present invention, the organic thin film layer includes a light emitting layer;
the material of the light emitting layer comprises a naphtho-benzo-heteroaromatic compound according to the first aspect.
In a third aspect, the present invention provides a display device comprising the organic electroluminescent device of the second aspect.
Compared with the prior art, the invention has the following beneficial effects:
According to the invention, through designing the structure of the naphtho-benzo heteroaromatic compound and controlling the hydrogen atom on the naphtho-benzo heteroaromatic compound to be substituted by a specific substituent, the naphtho-benzo heteroaromatic compound with a specific structure is obtained. The naphtho-benzo heteroaromatic compound provided by the invention can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Preparation example 1
The preparation example provides an intermediate M-7 and a synthesis method thereof, wherein the synthesis method comprises the following steps:
(1) Synthesis of intermediate M-1
100ML of THF and 40mL of water are sequentially added into a 250mL three-necked flask under the protection of nitrogen, then intermediate 1, 5-dibromo-2, 4-difluorobenzene (8.16 g,30 mmol), o-methoxyphenylboric acid (4.56 g,30 mmol), potassium carbonate (6.21 g,45 mmol) and tetrakis triphenylphosphine palladium (0.347 g,0.30 mmol) are added, the temperature is slowly increased to 65 ℃ for reaction for 12h, the temperature is reduced to room temperature, water is added, aqueous toluene is extracted once, the organic phases are combined, after the organic phases are washed with water, magnesium sulfate is dried, the solvent is removed under reduced pressure after the magnesium sulfate is removed, and the intermediate M-1 (5.38 g) is obtained through silica gel column chromatography separation and petroleum ether elution.
Mass spectrometry detection was performed on intermediate M-1, and the mass-to-charge ratio (M/z) was: 297.98&299.98.
(2) Synthesis of intermediate M-2
50ML of toluene, 25mL of ethanol and 25mL of water are sequentially added into a three-necked flask under the protection of nitrogen, then intermediate M-1 (5.00 g,16.72 mmol), 3-methoxy-2-naphthalene boric acid (3.72 g,18.39 mmol), potassium carbonate (3.46 g,25.08 mmol) and tetrakis triphenylphosphine palladium (0.193 g,0.167 mmol) are added, the temperature is slowly increased to 85 ℃ for reaction for 8h, the temperature is reduced to room temperature, water is added, aqueous phase toluene is extracted once, the organic phases are combined, after the organic phases are washed with water, magnesium sulfate is dried, the solvent is removed by filtration, the toluene and ethanol mixed solvent is removed under reduced pressure for crystallization, and intermediate M-2 (5.35 g) is obtained.
Mass spectrometry detection was performed on intermediate M-2, and the mass-to-charge ratio (M/z) was: 376.13.
(3) Synthesis of intermediate M-3
DCM (50 mL) was added to a 250mL three-necked flask under the protection of nitrogen, intermediate M-2 (5.35 g,14.22 mmol) was added, the temperature was lowered to 0 ℃, BBr 3 (14.22 mL,28.44mmol,2.0 mol/L) was started to be added dropwise, the reaction was carried out at 0 ℃ for 1h, then the temperature was naturally raised to room temperature, the reaction was carried out for 2h, the reaction system was cooled to below 0 ℃, water (50 mL) was slowly added dropwise, the organic phases were combined, the organic phases were washed with water, dried over magnesium sulfate, after the removal of magnesium sulfate by filtration, the solvent was removed under reduced pressure, and the mixed solvent of toluene and n-heptane was crystallized to obtain intermediate M-3 (4.70 g).
Mass spectrometry detection was performed on intermediate M-3, and the mass-to-charge ratio (M/z) was: 348.10.
(4) Synthesis of intermediate M-4
DMF (90 mL) and intermediate M-3 (4.50 g,12.92 mmol) and potassium carbonate (8.91 g,64.60 mmol) were added into a 250mL three-necked flask under the protection of nitrogen, the mixture was slowly warmed to 135 ℃ to react for 5h, cooled to room temperature, quenched by adding water, stirred for 1h, solid was separated out, filtered, filter cake was washed with water, filtered and dried to obtain intermediate M-4 (3.78 g).
Mass spectrometry detection was performed on intermediate M-4, and the mass-to-charge ratio (M/z) was: 308.08.
(5) Synthesis of intermediate M-5
Chloroform (105 mL) was added to a 250mL three-necked flask under the protection of nitrogen, intermediate M-4 (3.50 g,11.35 mmol) was further added, the temperature was lowered to 0℃and dropwise addition of a chloroform solution of bromine (14 mL) was started, the reaction was continued at 0℃for 10 hours, a saturated aqueous sodium sulfite solution (60 mL) was slowly added to the reaction system after the completion of the reaction, the solution was separated, the organic phase was washed with water, dried over magnesium sulfate, the magnesium sulfate was removed by filtration, and the solvent was removed under reduced pressure, and the mixed solvent of toluene and ethanol was crystallized to give intermediate M-5 (3.08 g).
Mass spectrometry was performed on intermediate M-5, and the two peaks with the largest mass-to-charge ratios (M/z) were: 385.99&387.99.
And performing nuclear magnetic resonance detection on the obtained M-5, wherein the data are as follows: 1 H-NMR (Bruker, switzerland, avance II 400MHz Nuclear magnetic resonance spectrometer ,CDCl3),δ：8.15(m,1H),7.98(m,1H),7.84(m,1H),7.50-7.52(m,3H),7.49(s,1H),7.45(s,1H),7.42(s,1H),7.31-7.39(m,2H).)
(6) Synthesis of intermediate M-6
Under the protection of nitrogen, 30mL of DMF (dimethyl formamide) and a compound shown as M-5 (3.00 g,7.75 mmol) are added into a three-port bottle under the protection of the nitrogen, the temperature is raised to 40 ℃ under stirring, N-iodosuccinimide solid (1.92 g,8.53 mmol) is added in batches, the mixture is reacted for 2 hours at the temperature of 40 ℃, the temperature is raised to 80 ℃ for 12 hours, the temperature is reduced to room temperature, water and chloroform are added for separating liquid, after the organic layer is washed by water, magnesium sulfate is dried, the solvent is removed under reduced pressure after the magnesium sulfate is filtered, and the petroleum ether is separated by silica gel column chromatography, wherein dichloromethane=20:1 (volume ratio) is eluted, so that an intermediate M-6 (2.01 g) is obtained.
Mass spectrometry was performed on intermediate M-6, and the two peaks with the largest mass-to-charge ratios (M/z) were: 511.89&513.89.
(7) Synthesis of intermediate M-7
20ML of toluene, 10mL of ethanol and 10mL of water are sequentially added into a 100mL three-necked flask under the protection of nitrogen, then intermediate M-6 (2.00 g,3.90 mmol), phenylboronic acid (0.48 g,3.90 mmol), sodium carbonate (0.83 g,7.80 mmol) and tetraphenylphosphine palladium (0.045 g,0.039 mmol) are added, the temperature is slowly increased to 50 ℃ for reaction for 2h, the temperature is increased to 70 ℃ for reaction for 6h, the temperature is reduced to room temperature, the water is added, the organic layer is washed with water, magnesium sulfate is dried, the solvent is removed by filtration, and the mixed solvent of toluene and ethanol is crystallized to obtain intermediate M-7 (1.51 g).
Mass spectrometry was performed on intermediate M-7, and the two peaks with the largest mass-to-charge ratios (M/z) were: 462.03&464.02.
Preparation examples 2 to 8
Preparation examples 2 to 8 each provided an intermediate, the synthesis method of which was referred to the synthesis method of intermediate M-7, except that phenylboronic acid in step (7) of preparation example 1 was replaced with other boric acid compounds (see Table 1 for details) in the amounts of the corresponding equivalent substances, and the other conditions were the same as the synthesis method of intermediate M-7, and mass spectrometry was performed on the intermediate, and the test data were shown in Table 1 below.
TABLE 1
Example 1
The present example provides a compound 1 and a method of synthesis thereof, the method of synthesis being as follows:
15mL of toluene, 7.5mL of ethanol and 7.5mL of water are sequentially added into a 100mL three-necked flask under the protection of nitrogen, then intermediate M-7 (1.50 g,3.24 mmol), 2-naphthalene boric acid (0.61 g,3.56 mmol), potassium carbonate (0.67 g,4.86 mmol) and tetrakis triphenylphosphine palladium (0.037 g,0.032 mmol) are added, the temperature is slowly increased to 85 ℃ for reaction for 6h, the temperature is reduced to room temperature, water is added, the toluene is extracted once, the organic phases are combined, after the organic phases are washed with water, magnesium sulfate is dried, the solvent is removed by filtration, the toluene and ethanol mixed solvent is removed under reduced pressure for crystallization, and the compound 1 (1.41 g) is obtained.
Mass spectrometry was performed on compound 1, and the mass-to-charge ratio (m/z) was: 510.16.
Examples 2 to 16
Examples 2 to 16 each provide a compound, the synthesis of which is referred to the synthesis of compound 1, except that intermediate M-7 is replaced with other intermediate in the amount of the same substance (see table 2 for details), 2-naphthalene boronic acid is replaced with other boronic acid compound in the amount of the same substance (see table 2 for details), and the mass spectrometry is performed on the synthesized compound under the same conditions as in the synthesis of compound 1, and the test data are shown in table 2 for details.
TABLE 2
Example 17
This example provides a compound 17 and a method of synthesis thereof, the method of synthesis being as follows:
(1) Synthesis of intermediate M-1S
The synthesis method of intermediate M-1 is referred to, and the difference is that 2-methoxyphenylboronic acid is replaced with an equivalent amount of 2-methylthiophenylboronic acid, and the other conditions are referred to the synthesis method of intermediate M-1.
Mass spectrometry detection was carried out on the intermediate M-1S, and the two peaks with the largest mass-to-charge ratios (M/z) are: 313.96&315.96.
(2) Synthesis of intermediate M-2S
Under the protection of nitrogen, 50mL of tetrahydrofuran is placed in a 250mL three-necked flask, 2-naphthalenyl sulfide (5.00 g,29 mmol) and triisopropyl borate (7.02 g,37 mmol) are added, the temperature is reduced to-70 ℃ to-90 ℃, n-butyllithium (14.94 mL,37 mmol) is added dropwise, the temperature is controlled to-70 ℃ to-90 ℃ for full reaction for 3-6h, the temperature is increased to 10 ℃ to 30 ℃, 100mL of acid water is added for quenching, extraction and decompression concentration are carried out, suction filtration is carried out, and crude product n-heptane solvent crystallization is obtained, thus obtaining 3-methylthio-2-naphthalene boric acid (5.01 g).
The synthesis method of M-1S to M-2S is different from the synthesis method of the intermediate M-2 only in that 3-methylthio-2-naphthaleneboronic acid is replaced with an equivalent amount of 3-methylthio-2-naphthaleneboronic acid, and other conditions are referred to the synthesis method of the intermediate M-2.
Mass spectrometry detection was carried out on the intermediate M-2S, and the mass-to-charge ratio (M/z) was: 408.08.
(3) Synthesis of intermediate M-6S
The synthesis methods of the intermediates M-3 to M-6 are referred to, and the difference is only that the intermediate M-2 is replaced with the equivalent amount of the substance M-2S, and the other conditions are referred to the synthesis methods of the intermediates M-3 to M-6.
Mass spectrometry detection was performed on intermediate M-2S, and the two peaks with the largest mass-to-charge ratios (M/z) were: 543.85&545.84.
(4) Synthesis of intermediate M-7S
The synthesis method of intermediate M-7 is referred to, and the difference is that phenylboronic acid is replaced with 1-naphthylboronic acid in the same amount, and other conditions are referred to the synthesis method of intermediate M-7.
Mass spectrometry detection was performed on intermediate M-7S, and the two peaks with the largest mass-to-charge ratios (M/z) were: 544.00&545.99.
(5) Synthesis of Compound 17
The synthesis method of the reference compound 1 is different from the synthesis method of the compound 1 only in that the intermediate M-7 is replaced by an intermediate M-7S having the same amount of the same substance, and the 2-naphthalene boric acid is replaced by 4-biphenyl boric acid having the same amount of the same substance, and other conditions are the same as those of the synthesis method of the compound 1.
Mass spectrometry was performed on compound 17, and the mass-to-charge ratio (m/z) was: 618.15.
Example 18
This example provides a compound 18 and a method of synthesis thereof, the method of synthesis being as follows:
(1) Synthesis of intermediate M-8S
The synthesis method of intermediate M-7 is referred to, and differs from the synthesis method of intermediate M-7 only in that intermediate M-6 is replaced with intermediate M-6S in an equal amount, and phenylboronic acid is replaced with 4-biphenylboronic acid in an equal amount, under the same conditions as in the synthesis method of intermediate M-7.
Mass spectrometry detection was carried out on the intermediate M-8S, and the two peaks with the largest mass-to-charge ratios (M/z) are: 570.01&572.01.
(2) Synthesis of Compound 18
The synthesis method of the reference compound 1 is different from the synthesis method of the compound 1 only in that the intermediate M-7 is replaced by an intermediate M-8S in an equal amount, and the 2-naphthalene boronic acid is replaced by a benzo [ b ] naphtho [2,3-d ] furan-3-yl boronic acid in an equal amount, and other conditions are the same as those of the compound 1.
Mass spectrometry was performed on compound 18, with a mass to charge ratio (m/z) of: 708.16.
Other compounds not specifically listed can be synthesized by referring to the above examples in combination with common knowledge in the art.
The specific structures of the partial compositions used in the following application examples and application comparative examples are as follows:
Application example 1
The application example provides an organic electroluminescent device, wherein the compound 1 provided in the embodiment 1 of the invention is used as a main material of a luminescent layer;
The organic electroluminescent device structure is as follows: ITO/HT (40 nm)/luminescent layer host material: BD-23% (30 nm)/TPBI (30 nm)/LiF (0.5 nm)/Al (150 nm).
The preparation method of the organic electroluminescent device comprises the following steps:
the glass substrate coated with the ITO transparent conductive layer (serving as an anode) is subjected to ultrasonic treatment in a cleaning agent, then washed in deionized water, then subjected to ultrasonic degreasing in a mixed solvent of acetone and ethanol, then baked in a clean environment until the water is completely removed, cleaned by ultraviolet light and ozone, and bombarded on the surface by a low-energy cation beam so as to improve the property of the surface and the bonding capability with a hole layer.
And placing the material in a vacuum cavity, vacuumizing to 1X 10 -5～1×10-6 Pa, and sequentially carrying out vacuum evaporation on the cleaned ITO substrate. Wherein, the luminescent layer host material: BD-23% (30 nm) refers to the fact that in the device, the host material of the light-emitting layer and BD-2 were co-evaporated in a volume ratio of 97:3 to form the light-emitting layer, which had a thickness of 30nm.
Application examples 2 to 10
Application examples 2 to 10 each provide an organic electroluminescent device differing from application example 1 only in the host material of the light-emitting layer (see table 3 below), and the other conditions are the same as application example 1.
Comparative examples 1 to 2 were used
Application comparative examples 1 to 2 each provide an organic electroluminescent device differing from application example 1 only in the light-emitting layer main body (see table 3 below for details), and the other conditions are the same as application example 1.
Performance testing
The testing method comprises the following steps: the OLED-1000 multichannel accelerated aging life and photochromic performance analysis system manufactured in Hangzhou is used for testing the driving voltage, the current efficiency and the life LT90 of the OLED device; the LT90 is the time required for maintaining the current density at the initial luminance of 1000nit and reducing the luminance to 90% of the original luminance, and the test items include luminance, driving voltage and current efficiency of the organic electroluminescent device, and the driving voltage and current efficiency and LT90 data are relative values at the luminance of 1000cd/m 2.
The performance test results of the organic electroluminescent device are shown in the following table 3:
TABLE 3 Table 3
As is clear from the contents of Table 3, according to the present invention, a naphtho-benzo-heteroaromatic compound having a specific structure is obtained by designing the structure of the naphtho-benzo-heteroaromatic compound. The naphtho-benzo heteroaromatic compound provided by the invention can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
The applicant states that the detailed process flow of the present invention is illustrated by the above examples, but the present invention is not limited to the above detailed process flow, i.e. it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (7)
1. An organic compound, characterized in that the organic compound has a structure represented by the following formula BH-a:
wherein Ar 1 and Ar 2 are each independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;
X is selected from O or S;
Ar 1 and Ar 2 are independently selected from at least one of-D, -F, -CN, C1-C10 alkyl, C1-C5 alkoxy or C6-C15 aryl;
The hydrogen atoms in the compound of the formula BH-A are each independently and optionally substituted by at least one of-D, -F, -CN, C1-C5 alkyl, C1-C5 alkoxy;
The C6-C40 aryl is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylene, fluoranthryl, hydrogenated benzoanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl;
The C12-C20 heteroaryl is selected from dibenzofuranyl dibenzothienyl group benzodibenzofuranyl group benzodibenzothienyl dinaphthofuranyl or dinaphtho any one of thienyl.
2. The organic compound according to claim 1, wherein Ar 1 and Ar 2 are each independently selected from any one of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl.
3. The organic compound of claim 1, wherein the hydrogen atoms in the compound of formula BH-a are each independently optionally substituted with at least one of-D, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy.
4. The organic compound of claim 1, wherein the compound of formula BH-a is selected from any one of the following compounds:
wherein X is selected from O or S.
5. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
the material of the organic thin film layer includes the organic compound according to any one of claims 1 to 4.
6. The organic electroluminescent device according to claim 5, wherein the organic thin film layer comprises a light emitting layer, and a material of the light emitting layer comprises the organic compound according to any one of claims 1 to 4.
7. A display device, characterized in that the display device comprises the organic electroluminescent device as claimed in claim 5 or 6.
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| KR20210010006A (en) * | 2019-07-19 | 2021-01-27 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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