CN117794916A - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- CN117794916A CN117794916A CN202380013130.6A CN202380013130A CN117794916A CN 117794916 A CN117794916 A CN 117794916A CN 202380013130 A CN202380013130 A CN 202380013130A CN 117794916 A CN117794916 A CN 117794916A
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- 229910052805 deuterium Inorganic materials 0.000 claims description 27
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PJRJXFPRMUZBHQ-UHFFFAOYSA-N [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 Chemical compound [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 PJRJXFPRMUZBHQ-UHFFFAOYSA-N 0.000 description 1
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- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 150000001616 biphenylenes Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- BGTFRFFRQKBWLS-UHFFFAOYSA-M lithium;quinolin-2-olate Chemical compound [Li+].C1=CC=CC2=NC([O-])=CC=C21 BGTFRFFRQKBWLS-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical group [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection 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
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification relates to a compound and an organic light emitting device including the same.
The present application claims priority from korean patent application No. 10-2022-0032155, filed to the korean patent office on 15 th 2022, the entire contents of which are incorporated herein.
Background
In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor substance, and communication of holes and/or electrons between an electrode and the organic semiconductor substance is required. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first is a light-emitting device in which an exciton (exiton) is formed in an organic layer by photons flowing into the device from an external light source, and the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which a voltage or a current is applied to 2 or more electrodes, holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes, and the injected electrons and holes operate.
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons re-transition to a ground state. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.
Materials used as an organic layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, such as a hole injecting material, a hole transporting material, an electron inhibiting substance, an electron transporting material, an electron injecting material, and the like, according to functions. Depending on the emission color, the luminescent materials are blue, green, red luminescent materials, and yellow and orange luminescent materials, which are required to achieve better natural colors.
In addition, for the purpose of an increase in color purity and an increase in luminous efficiency based on energy transfer, as a light emitting material, a host/dopant system may be used. The principle is that when a dopant having a smaller band gap and excellent light emission efficiency than a host mainly constituting the light emitting layer is mixed in a small amount in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the kind of the dopant to be used.
In order to fully develop the excellent characteristics of the organic light-emitting device, materials constituting the organic layer in the device, for example, hole injection materials, hole transport materials, light-emitting materials, electron-suppressing materials, electron transport materials, electron injection materials, and the like are stable and effective materials, and therefore development of new materials is continuously demanded.
Disclosure of Invention
Technical problem
The present specification describes compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound of the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
l1 and L2 are identical to or different from each other and are each independently a direct bond, unsubstituted arylene, or heteroarylene,
Ar1 is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the above-mentioned chemical formula 2,
x1 is NR, O, S, CR R2, N linked to L1, or CR1 linked to L1,
x2 to X5 are identical to or different from each other and are each, independently of one another, N, CR3 or C linked to L1,
r and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may be combined with each other with adjacent substituents to form a substituted or unsubstituted ring,
however, one of X1 to X5 is linked to L1, the remainder being NR, or at least one of X2 to X5 being N,
in the above-mentioned chemical formula 3, a compound represented by formula 1,
y1 is O or S, and the total number of the components is equal to or less than zero,
y2 and Y3 are identical to or different from each other and are each independently N or CR4,
y4 to Y7 are identical to or different from each other and are each independently N, CR5 or C linked to L1,
any one of Y4 to Y7 is C connected to L1,
r4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may combine with each other with an adjacent substituent to form a substituted or unsubstituted ring,
ar2 is represented by the following chemical formula 4,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
x6 to X11 are identical to or different from each other and are each, independently of one another, N, CR6 or C combined with L2,
any one of X6 to X11 is C bonded to L2, at least one of the others is N,
r6 is deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may be combined with each other with an adjacent substituent to form a substituted or unsubstituted ring,
however, ar1 is not a carbazolyl group.
In addition, according to an embodiment of the present invention, there is provided an organic light emitting device including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.
Effects of the invention
The compound of the present invention can be used as a material of an organic layer of an organic light emitting device. When the compound of the present invention is contained in an electron injection and transport layer of an organic light-emitting device, the compound of the present invention has high intramolecular polarizability and good electron transfer effect, and thus an organic light-emitting device having long-life characteristics can be produced.
Drawings
Fig. 1 and 2 illustrate examples of an organic light emitting device according to the present invention.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group (-CN), silyl group, boron group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents bonded with the above exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).
In this specification, the silyl group may be substituted or unsubstituted with deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or the like. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be substituted or unsubstituted with deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include, but are not limited to, dimethylboronyl, diethylboronyl, t-butylmethylboronyl, diphenylboronyl, phenylboronyl, and the like.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and the like.
In the present specification, the amine group may be selected from the group consisting of-NH 2 Alkylamino, N-alkylaryl aminesThe group, arylamino group, N-arylheteroarylamino group, N-alkylheteroarylamino group and heteroarylamino group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methylanthracenylamine group, a diphenylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.
In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.
In the present specification, an N-arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group.
In the present specification, an N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group.
In the present specification, alkylamino, N-arylalkylamino, alkylthio Alkylsulfonyl->The alkyl group in the N-alkylheteroaryl amine group is the same as exemplified above for the alkyl group. Specifically, the alkylthio group includes a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, and the alkylsulfonyl group includes a methanesulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and the like, but is not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the heteroaryl group is a cyclic group containing 1 or more of N, O, P, S, si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
In the present specification, the definition of arylene is the same as that of aryl described above except that arylene is a 2-valent group.
In the present specification, the heteroaryl group is defined as in the above heteroaryl group except that the heteroaryl group is a 2-valent group.
In this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the above chemical formulas 1-1 to 1-6, the above L1, L2, ar1 and Ar2 are as defined in chemical formula 1.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent naphthyl, 2-valent anthryl, 2-valent phenanthryl, 2-valent pyrenyl, 2-valent carbazolyl, 2-valent pyridyl, 2-valent pyrimidinyl, 2-valent triazinyl, 2-valent dibenzofuranyl, 2-valent dibenzothiophenyl, 2-valent furanyl, 2-valent thiophenyl, 2-valent benzimidazolyl or 2-valent benzo An azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent naphthyl, 2-valent terphenyl, 2-valent carbazolyl, 2-valent pyridyl, 2-valent pyrimidinyl, 2-valent triazinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent furyl, 2-valent thienyl, 2-valent benzimidazolyl or 2-valent benzoAn azole group.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, a phenylene group, a 2-valent biphenyl group, a 2-valent naphthyl group, or a 2-valent terphenyl group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, a carbazolyl group of 2 valences, a pyridyl group of 2 valences, a pyrimidinyl group of 2 valences, a triazinyl group of 2 valences, a dibenzofuranyl group of 2 valences, a dibenzothienyl group of 2 valences, a furyl group of 2 valences, a thienyl group of 2 valences, a benzimidazolyl group of 2 valences or a benzo group of 2 valencesAn azole group.
According to one embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent Is a terphenyl group, a 2-valent naphthyl group, a 2-valent anthryl group, a 2-valent phenanthryl group, a 2-valent pyrenyl group, a 2-valent carbazolyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, a 2-valent triazinyl group, a 2-valent dibenzofuranyl group, a 2-valent dibenzothienyl group, a 2-valent furanyl group, a 2-valent thienyl group, a 2-valent benzimidazolyl group or a 2-valent benzo groupAn azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent carbazolyl, 2-valent pyridyl, 2-valent pyrimidinyl, 2-valent triazinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent furyl, 2-valent thienyl, 2-valent benzimidazolyl or 2-valent benzoAn azole group.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, a phenylene group, a 2-valent biphenyl group, a 2-valent naphthyl group, or a 2-valent terphenyl group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, a carbazolyl group of 2 valences, a pyridyl group of 2 valences, a pyrimidinyl group of 2 valences, a triazinyl group of 2 valences, a dibenzofuranyl group of 2 valences, a dibenzothienyl group of 2 valences, a furyl group of 2 valences, a thienyl group of 2 valences, a benzimidazolyl group of 2 valences or a benzo group of 2 valences An azole group.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and are each independently phenylene, naphthyl of 2 valency, biphenyl of 2 valency or terphenyl of 2 valency.
According to one embodiment of the present specification, L1 and L2 are the same or different from each other and each is independently a carbazolyl group having a valence of 2, a pyridyl group having a valence of 2,Pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, furanyl, thienyl, benzimidazolyl, or benzo, respectively, 2An azole group.
According to an embodiment of the present disclosure, the L1 and L2 are directly bonded.
According to an embodiment of the present specification, the above L1 and L2 are phenylene groups.
According to one embodiment of the present specification, L1 and L2 are 2-valent naphthyl groups.
According to an embodiment of the present specification, L1 and L2 are biphenyl groups having a valence of 2.
According to one embodiment of the present specification, L1 and L2 are 2-valent terphenyl groups.
According to an embodiment of the present disclosure, L1 is a direct bond.
According to one embodiment of the present specification, L1 is phenylene.
According to one embodiment of the present specification, L1 is a 2-valent naphthyl group.
According to one embodiment of the present specification, L1 is a 2-valent biphenyl group.
According to one embodiment of the present specification, L1 is a 2-valent terphenyl group.
According to an embodiment of the present disclosure, the L2 is a direct bond.
According to an embodiment of the present specification, the L2 is phenylene.
According to one embodiment of the present specification, L2 is a 2-valent naphthyl group.
According to one embodiment of the present specification, L2 is a 2-valent biphenyl group.
According to one embodiment of the present specification, L2 is a 2-valent terphenyl group.
According to one embodiment of the present specification, X1 is NR.
According to one embodiment of the present specification, X1 is O.
According to one embodiment of the present disclosure, X1 is S.
According to one embodiment of the present disclosure, X1 is CR1R2.
According to one embodiment of the present specification, X1 is CR1 bonded to L.
According to an embodiment of the present disclosure, X2 is N.
According to an embodiment of the present disclosure, X3 is N.
According to an embodiment of the present disclosure, X4 is N.
According to an embodiment of the present disclosure, X5 is N.
According to one embodiment of the present disclosure, X2 is CR3.
According to one embodiment of the present disclosure, X3 is CR3.
According to an embodiment of the present disclosure, X4 is CR3.
According to one embodiment of the present disclosure, X5 is CR3.
According to an embodiment of the present specification, X2 is C bonded to L.
According to an embodiment of the present specification, X3 is C bonded to L.
According to an embodiment of the present specification, X4 is C bonded to L.
According to an embodiment of the present specification, X5 is C bonded to L.
According to an embodiment of the present specification, X1 is O, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is O, any two of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present specification, X1 is O, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present disclosure, X1 is O, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is S, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present disclosure, X1 is S, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is S, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present disclosure, X1 is S, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is CR1R2, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is CR1R2, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is CR1R2, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present disclosure, X1 is CR1 bonded to L, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is NR, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is NR, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is NR, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present specification, X1 is NR, and X2 to X5 are CR3.
According to one embodiment of the present disclosure, X1 is N or CR1 bonded to L.
According to one embodiment of the present disclosure, X2 and X3 are CR3, and adjacent R3 are bonded to each other to form a ring substituted or unsubstituted with an unsubstituted alkyl group or an unsubstituted aryl group.
According to an embodiment of the present specification, X3 and X4 are CR3, and adjacent R3 are bonded to each other to form a ring substituted or unsubstituted with an unsubstituted alkyl group or an unsubstituted aryl group.
According to one embodiment of the present specification, X4 and X5 are CR3, and adjacent R3 are bonded to each other to form a ring substituted or unsubstituted with an unsubstituted alkyl group or an unsubstituted aryl group.
According to an embodiment of the present specification, at least one of X2 to X5 is N.
According to one embodiment of the present disclosure, Y1 is O.
According to one embodiment of the present disclosure, Y1 is S.
According to an embodiment of the present disclosure, Y2 is N.
According to one embodiment of the present disclosure, Y2 is CR4.
According to one embodiment of the present disclosure, Y3 is N.
According to one embodiment of the present disclosure, Y3 is CR4.
According to an embodiment of the present disclosure, Y2 and Y3 are N.
According to an embodiment of the present disclosure, Y2 and Y3 are CR4.
According to one embodiment of the present disclosure, Y2 is N, and Y3 is CR4.
According to one embodiment of the present disclosure, Y3 is N, and Y2 is CR4.
According to an embodiment of the present specification, at least one of Y2 to Y7 is N.
According to an embodiment of the present specification, three of Y4 to Y7 are CR5, and the remaining one is C bonded to L.
According to an embodiment of the present specification, three of Y4 to Y7 are N, and the remaining one is C combined with L.
According to one embodiment of the present specification, Y4 is C connected to L1.
According to one embodiment of the present specification, Y5 is C connected to L1.
According to one embodiment of the present specification, Y6 is C connected to L1.
According to one embodiment of the present specification, Y7 is C connected to L1.
According to an embodiment of the present specification, ar1 is any one of the following structural formulas, which are substituted or unsubstituted.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, each independently hydrogen, deuterium, unsubstituted alkyl or unsubstituted aryl, or are combined with each other with adjacent substituents to form a ring substituted or unsubstituted with unsubstituted alkyl or unsubstituted aryl.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl or anthracenyl, or form a ring substituted or unsubstituted with any one or more selected from methyl, ethyl, propyl, isopropyl, butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl and anthracenyl, in combination with each other with an adjacent substituent.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl, or forms an aromatic hydrocarbon ring substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, or naphthyl, or forms a benzene ring substituted or unsubstituted with any one or more selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, and naphthyl.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, or naphthyl, or forms a naphthalene ring substituted or unsubstituted with any one or more selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, and naphthyl.
According to one embodiment of the present specification, ar1 is benzimidazolyl substituted or unsubstituted with an alkyl or aryl group, imidazolyl substituted or unsubstituted with an alkyl or aryl group, or benzo substituted or unsubstituted with an alkyl or aryl group Oxazolyl, substituted or unsubstituted by alkyl or aryl ++>Diazolyl, or benzothiazolyl substituted or unsubstituted with alkyl or aryl.
According to one embodiment of the present specification, ar1 is benzimidazolyl, imidazolyl, or benzoAzolyl, (-) -and (II) radicals>An oxadiazolyl group or a benzothiazolyl group,
the benzimidazolyl group described above; imidazolyl; benzo (E) benzo (EAn azole group; />The diazolyl or benzothiazolyl group is substituted or unsubstituted with any one or more selected from the group consisting of methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, biphenyl, naphthyl and terphenyl.
According to an embodiment of the present specification, ar1 is any one of the following structures.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least one of the others is N, and the others are CR6.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least two of the others are N, and the others are CR6.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least three of the others are N, and the others are CR6.
According to an embodiment of the present specification, X6 of the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X7 of the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X8 in the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X9 of the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X10 of the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X11 of the above X6 to X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X6 and X8 among X6 to X11 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X6 and X7 among X6 to X11 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X6 and X9 in X6 to X11 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, X6, X8, and X10 among X6 to X11 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, R6 is deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R6 is deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or may be bonded to each other with an adjacent substituent to form a ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, ar2 mentioned above is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.
According to an embodiment of the present specification, ar2 is a pyridinyl group substituted or unsubstituted with an aryl group, a pyrimidinyl group substituted or unsubstituted with an aryl group, or a triazinyl group substituted or unsubstituted with an aryl group.
According to an embodiment of the present specification, ar2 is a pyridinyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a pyrimidinyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or a triazinyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, ar2 is a pyridyl group, a pyrimidinyl group or a triazinyl group, which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, the above Ar2 is a pyridyl group, a pyrimidinyl group or a triazinyl group, which is substituted or unsubstituted with any one or more selected from phenyl, biphenyl, terphenyl and naphthyl.
According to an embodiment of the present specification, the above Ar2 is a pyridyl group, a pyrimidinyl group or a triazinyl group, which are substituted with any one or more selected from phenyl, biphenyl, terphenyl and naphthyl groups.
According to an embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.
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The substituents of the compound of the above chemical formula 1 may be combined according to a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.
In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required for each organic layer can be synthesized by introducing substituents mainly used in the hole injection layer substance, the hole transport substance, the light emitting layer substance, and the electron transport layer substance used in manufacturing the organic light emitting device into the above-described core structure.
In addition, the organic light emitting device according to the present invention is characterized by comprising: a first electrode, a second electrode disposed opposite to the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the above-mentioned compound.
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers or a greater number of organic layers.
In the organic light emitting device of the present invention, the electron injection layer, the electron transport layer, or the electron injection and transport layer further contains a metal complex or an n-type dopant.
In the organic light emitting device of the present invention, the electron transport layer or the electron injection and transport layer further contains a metal complex or an n-type dopant.
In the organic light emitting device of the present invention, the organic layer may include 1 or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and 1 or more of the layers may include the compound represented by the chemical formula 1.
In another organic light emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by the chemical formula 1.
In the organic light emitting device of the present invention, the electron injection and transport layer includes the compound of the above chemical formula 1 and a metal complex.
In the organic light emitting device of the present invention, the electron injection and transport layer contains the compound of the above chemical formula 1 and lithium quinolinolate.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:5 to 5:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate at a weight ratio of 1:10 to 10:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate in a weight ratio of 1:5 to 5:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate in a weight ratio of 1:3 to 3:1.
In the organic light emitting device of the present invention, the organic layer includes a hole blocking layer including the compound of formula 1.
In the organic light emitting device of the present invention, the organic layer may include 1 or more layers of a hole injection layer, a hole transport layer, and a layer in which hole injection and hole transport are simultaneously performed, and 1 or more layers of the layers may include the compound represented by the chemical formula 1.
In another organic light emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by chemical formula 1.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, an organic layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport layer 8.
For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and then an organic layer including 1 or more layers selected from a hole injection layer, a hole transport layer, a layer in which hole transport and hole injection are performed simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and a layer in which electron transport and electron injection are performed simultaneously is formed on the anode, and then a substance usable as a cathode is deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented.
According to an embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.
[ chemical formula HI-1]
In the above-mentioned chemical formula HI-1,
r300 to R308 are identical to or different from each other and are each independently hydrogen, deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other with adjacent groups to form a substituted or unsubstituted ring,
r301 and r302 are each integers from 1 to 4,
r303 and r304 are each integers from 1 to 3,
when R301 is 2 or more, R301 may be the same or different from each other,
when R302 is 2 or more, R302 may be the same or different from each other,
when R303 is 2 or more, R303 may be the same or different from each other,
when R304 is 2 or more, R304 may be the same or different from each other.
According to an embodiment of the present disclosure, R301 to R304 are hydrogen.
According to one embodiment of the present disclosure, R300 is a substituted or unsubstituted aryl group.
According to one embodiment of the present specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present disclosure, R300 is phenyl.
According to an embodiment of the present specification, the above R305 to R308 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, R305 to R308 are the same or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, the above R305 to R308 are the same or different from each other, and each is independently a phenyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group.
According to one embodiment of the present specification, the above formula HI-1 is represented by the following chemical.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
According to an embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.
[ chemical formula HT-1]
In the above-mentioned chemical formula HT-1,
at least one of X '1 to X'6 is N, the remainder are CH,
r309 to R314 are the same or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, X '1 to X'6 are N.
According to one embodiment of the present disclosure, R309 to R314 are nitrile groups.
According to one embodiment of the present specification, the above formula HT-1 is represented by the following compounds.
According to an embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
[ chemical formula HT-2]
In the above-mentioned chemical formula HT-2,
r315 to R317 are the same or different from each other and are each independently any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with each other with adjacent groups to form a substituted or unsubstituted ring,
R315 is an integer of 1 to 5, and when R315 is 2 or more, 2 or more of R315 are the same or different from each other,
r316 is an integer of 1 to 5, and when R316 is 2 or more, 2 or more R316 are the same or different from each other.
According to an embodiment of the present disclosure, R317 is any one selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof.
According to an embodiment of the present specification, R317 is any one selected from carbazolyl, phenyl, biphenyl, and combinations thereof.
According to an embodiment of the present specification, R315 and R316 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group, or are combined with each other to form an alkyl-substituted aromatic hydrocarbon ring.
According to an embodiment of the present specification, R315 and R316 are the same or different from each other, each independently is phenyl, or are combined with each other with adjacent groups to form methyl-substituted indene.
According to one embodiment of the present specification, the above formula HT-2 is represented by the following compounds.
/>
An electron-inhibiting layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-inhibiting layer may be formed using the spiro compound described above or a material known in the art.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Main material as luminous layerExamples of the materials include aromatic condensed ring derivatives and heterocyclic compounds. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.
According to an embodiment of the present specification, the body includes a compound represented by the following chemical formula H-1, but is not limited thereto.
[ chemical formula H-1]
In the above-mentioned chemical formula H-1,
l20 and L21 are the same or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group of 2 valency,
ar20 and Ar21 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r201 is an integer of 1 to 8, and when R201 is 2 or more, 2 or more R201 are the same or different from each other.
In one embodiment of the present specification, L20 and L21 are the same or different from each other, and each is independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In an embodiment of the present specification, the above L20 and L21 are the same or different from each other, and each is independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothienyl group.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; thienyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; dibenzofuranyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
In an embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted with deuterium, a thienyl group substituted or unsubstituted with phenyl group, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothienyl group, or a naphthobenzothienyl group.
In one embodiment of the present specification, ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R201 is hydrogen.
According to an embodiment of the present specification, the above formula H-1 is represented by the following compound.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene having an arylamine group,Bisindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
According to an embodiment of the present specification, the dopant includes a compound represented by the following chemical formula D-1, but is not limited thereto.
[ chemical formula D-1]
In the above-mentioned chemical formula D-1,
t1 to T6 are identical to or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
t5 and t6 are each an integer of 1 to 4,
when T5 is 2 or more, T5 of 2 or more are the same or different from each other,
when T6 is 2 or more, T6 s of 2 or more are the same or different from each other.
According to an embodiment of the present specification, T1 to T6 are the same or different from each other, and each is independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned T1 to T6 are the same or different from each other, each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a nitrile group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other, and each is independently hydrogen, isopropyl, phenyl substituted with nitrile group, or phenyl substituted with methyl group.
According to an embodiment of the present specification, the above chemical formula D-1 is represented by the following compound.
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer, the electron transport layer, and the electron injection and transport layer may further comprise a metal complex or an n-type dopant.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Concrete embodimentsAs the solvent, fluorenone, anthraquinone-dimethane, diphenoquinone, thiopyran dioxide, and the like are mentioned,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the electron injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The method of manufacturing the compound of chemical formula 1 above and the manufacture of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following reaction formulae, the kinds and numbers of substituents can be appropriately selected according to the known starting materials by those skilled in the art to synthesize various types of intermediates. The type of reaction and the reaction conditions may utilize techniques known in the art.
The method of manufacturing the compound of chemical formula 1 above and the manufacture of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following reaction formulae, the kinds and numbers of substituents can be appropriately selected according to the known starting materials by those skilled in the art to synthesize various types of intermediates. The type of reaction and the reaction conditions may utilize techniques known in the art.
[ general formula 1]
In the above reaction formula 1, L2, ar1 and Ar2 are as defined in the above chemical formula 1, and Y is a halogen group, preferably a bromine group or a chlorine group.
The above reaction is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be modified according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
If the production formula described in the examples of the present specification and the above intermediate are appropriately combined based on common technical knowledge, all the compounds of the above chemical formula 1 described in the present specification can be produced.
Synthesis example
Synthesis example 1: production of Compound E1
E1-A (20 g,41.5 mmol) and E1-B (18.1 g,41.5 mmol) were added to 400ml of 1,4-di under nitrogenThe mixture was stirred and refluxed in an alkane (1, 4-Dioxane). Then, potassium phosphate (26.4 g,124.5 mmol) was dissolved in 26ml of water and added thereto, and after stirring well, dibenzylideneacetone palladium (0.7 g,1.2 mmol) and tricyclohexylphosphine (0.7 g,2.5 mmol) were added thereto. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into 940mL of chloroform and dissolved, the organic layer was separated after washing with water 2 times, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to yield yellow solid compound E1 (4.7 g, 15%).
MS:[M+H] + ＝755
Synthesis example 2: production of Compound E2
The compound E2 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝707
Synthesis example 3: production of Compound E3
The compound E3 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝772
Synthesis example 4: production of Compound E4
The compound E4 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝728
Synthesis example 5: production of Compound E5
The compound E5 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝730
Synthesis example 6: production of Compound E6
The compound E6 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝707
Synthesis example 7: production of Compound E7
The compound E7 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝730
Synthesis example 8: production of Compound E8
The compound E8 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝707
Synthesis example 9: production of Compound E9
The compound E9 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝799
Synthesis example 10: production of Compound E10
The compound E10 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝633
Synthesis example 11: production of Compound E11
The compound E11 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝680
Synthesis example 12: production of Compound E12
The compound E12 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝730
Synthesis example 13: production of Compound E13
The compound E13 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝730
Synthesis example 14: production of Compound E14
The compound E14 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝707
Synthesis example 15: production of Compound E15
The compound E15 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝755
Experimental example
Experimental example 1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HI-A was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, hexanitrile hexaazabenzophenanthrene (HAT, -/-A) of the following chemical formula is formed>) And the following compound HT-A->Vacuum evaporation is sequentially performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe following compounds BH and BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. / >
On the light-emitting layer, the compound E1 produced in Synthesis example 1 and the following compound [ LiQ ]]Vacuum evaporation was performed at a weight ratio of 1:1 to obtain a solution of lithium quinolineForm electron transport and injection layers. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 ～5×10 -8 The support is thus fabricated into an organic light emitting device.
Experimental examples 2 to 15
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1.
Comparative examples 1 to 7
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1. The compounds of ET-1 to ET-7 used in table 1 below are shown below.
The organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples were subjected to a temperature of 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 The time (T) at which the initial luminance was 90% was measured at the current density of (2) 90 ). The results are shown in table 1 below.
TABLE 1
As described in the above table 1, it was confirmed that the organic light emitting device using the compound represented by chemical formula 1 of the present invention was excellent in voltage, efficiency and/or lifetime (T 90 ) Exhibits excellent characteristics.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental examples 1 to 3, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in terms of efficiency and lifetime compared to the organic light emitting device using the L-substituted compound.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental example 4, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in terms of efficiency compared to the organic light emitting device using the different compounds of Ar1 and Ar 2.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental example 5, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in terms of lifetime compared to the organic light emitting device using the compound unsubstituted with a nitrile group.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental examples 6 to 7, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in efficiency and lifetime compared to the organic light emitting device using the compound substituted with two nitrile groups.
Claims (13)
1. A compound of the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
l1 and L2 are identical to or different from each other and are each independently a direct bond, unsubstituted arylene, or heteroarylene,
ar1 is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the chemical formula 2 described above, the chemical formula,
x1 is NR, O, S, CR R2, N linked to L1, or CR1 linked to L1,
x2 to X5 are identical to or different from each other and are each, independently of one another, N, CR3 or C linked to L1,
r and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are capable of forming a substituted or unsubstituted ring in combination with each other with the adjacent substituents,
however, one of X1 to X5 is linked to L1, the remainder being NR, or at least one of X2 to X5 being N,
in the chemical formula 3 described above, the chemical formula,
Y1 is O or S, and the total number of the components is equal to or less than zero,
y2 and Y3 are identical to or different from each other and are each independently N or CR4,
y4 to Y7 are identical to or different from each other and are each independently N, CR5 or C linked to L1,
any one of Y4 to Y7 is C connected to L1,
r4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are capable of forming a substituted or unsubstituted ring in combination with each other with the adjacent substituents,
ar2 is represented by the following chemical formula 4,
[ chemical formula 4]
In the chemical formula 4 described above, the chemical formula,
x6 to X11 are identical to or different from each other and are each, independently of one another, N, CR6 or C combined with L2,
any one of X6 to X11 is C bonded to L2, at least one of the others is N,
r6 is deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or is capable of forming a substituted or unsubstituted ring in combination with each other with the adjacent substituent,
however, ar1 is not a carbazolyl group.
2. The compound of claim 1, wherein L1 and L2 are the same or different from each other, each independently being a direct bond, an arylene group of 6 to 30 carbon atoms, or a heteroarylene group of 3 to 30 carbon atoms.
3. The compound of claim 1, wherein any one of X6 to X11 is C bound to L2, at least one of the others is N, and the others are CR6.
4. The compound of claim 1, wherein at least one of X2 to X5 is N.
5. The compound of claim 1, wherein at least one of Y2 to Y7 is N.
6. The compound of claim 1, wherein R and R1 to R3 are the same or different from each other, each independently hydrogen, deuterium, unsubstituted alkyl, or unsubstituted aryl, or combine with adjacent substituents with each other to form a ring substituted or unsubstituted with unsubstituted alkyl or unsubstituted aryl.
7. The compound of claim 1, wherein Ar1 is benzimidazolyl substituted or unsubstituted with alkyl or aryl, imidazolyl substituted or unsubstituted with alkyl or aryl, benzo substituted or unsubstituted with alkyl or arylOxazolyl, substituted or unsubstituted by alkyl or aryl ++>Diazolyl, or benzothiazolyl substituted or unsubstituted with alkyl or aryl.
8. The compound of claim 1, wherein Ar2 is substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazinyl.
9. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the chemical formulas 1-1 to 1-6, the L1, L2, ar1 and Ar2 are as defined in chemical formula 1.
10. The compound of claim 1, wherein the chemical formula 1 is any one of the following compounds:
11. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 10.
12. The organic light-emitting device according to claim 11, wherein the organic layer includes 1 or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and 1 or more of the layers contains the compound represented by the chemical formula 1.
13. The organic light emitting device of claim 12, wherein the electron transport layer, electron injection layer, or electron injection and transport layer comprises the compound of chemical formula 1 and a metal complex in a weight ratio of 1:3 to 3:1.
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| KR20220032155 | 2022-03-15 | ||
| KR10-2022-0032155 | 2022-03-15 | ||
| PCT/KR2023/003377 WO2023177176A1 (en) | 2022-03-15 | 2023-03-13 | Compound and organic light-emitting element comprising same |
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| Country | Link |
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| KR (1) | KR20230134993A (en) |
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| ES2887148T3 (en) | 2015-03-25 | 2021-12-21 | Nat Cancer Ct | Therapeutic agent against bile duct cancer |
| KR101946020B1 (en) * | 2015-09-10 | 2019-02-08 | 엘티소재주식회사 | Hetero-cyclic compound and organic light emitting device using the same |
| KR102101473B1 (en) * | 2017-07-10 | 2020-04-16 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| EP3556746A1 (en) * | 2018-04-18 | 2019-10-23 | Novaled GmbH | Compound, method for preparing the same, organic semiconducting layer, organic electronic device, display and lighting device comprising the same |
| CN112047930B (en) * | 2019-06-06 | 2024-03-12 | 北京鼎材科技有限公司 | Compound and application thereof, and organic electroluminescent device comprising compound |
| CN113045553A (en) * | 2021-03-30 | 2021-06-29 | 烟台显华化工科技有限公司 | Aza-aromatic compound used as electron transport material and application thereof |
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