CN113227063B - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- CN113227063B CN113227063B CN202080007245.0A CN202080007245A CN113227063B CN 113227063 B CN113227063 B CN 113227063B CN 202080007245 A CN202080007245 A CN 202080007245A CN 113227063 B CN113227063 B CN 113227063B
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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
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 125000003943 azolyl group Chemical group 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
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- 125000006267 biphenyl group 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
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- 150000001638 boron Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000001716 carbazoles Chemical class 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
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- 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
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
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- 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 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
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000000623 heterocyclic group 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
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 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
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 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
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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Abstract
The present invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2019-0017983, 2 nd month 15 of 2019, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
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 has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, excitons (exciton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to a ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
[ Prior Art literature ]
[ Patent literature ]
(Patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 to L 3 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
A is phenanthryl, triphenylene, dibenzofuranyl or dibenzothiophenyl,
Wherein, the A is unsubstituted or independently selected from C 1-20 alkyl; c 6-20 aryl; and more than 1 substituent substitution in a C 2-20 heteroaryl group comprising any one or more heteroatoms selected from N, O and S,
B is a substituent represented by the following chemical formula 2,
Ar is a substituent represented by the following chemical formula 2; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
[ Chemical formula 2]
In the above-mentioned chemical formula 2,
X is O or S, and the X is O or S,
One of R 1 to R 3 is combined with L 2 or L 3, the others each independently being hydrogen; deuterium; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
However, in the case where L 2 or L 3 is bound to R 1 or R 2, the unbound R 1 or R 2 is not hydrogen,
N is an integer from 1 to 4.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjustment layer 8, a light-emitting layer 4, an electron adjustment layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
Definition of terms
In the present description of the invention,And/>Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]Alkyl thioxy) of the formula (i); arylthio (/ >) Aryl thioxy) of the formula (i); alkylsulfonyl (/ >)Alkyl sulfoxy) of the formula (i); arylsulfonyl (/ >)Aryl sulfoxy) of the formula (i); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom, or a substituent linked with 2 or more substituents in the above-exemplified substituents. 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.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is 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 specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are 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, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is 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, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl,/>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo/>Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline, iso/>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In this specification, alkenyl groups in aralkenyl groups are the same as the examples of alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied thereto. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
Compounds of formula (I)
In another aspect, the present invention provides an amine compound represented by the above chemical formula 1.
The amine-based compound represented by the above chemical formula 1 contains any one substituent of phenanthryl, triphenylene, dibenzofuranyl, and dibenzothienyl and any one substituent of benzofuranyl and benzothienyl at the same time, whereby high efficiency, low driving voltage, long life, and the like of an organic light emitting device using the same can be achieved. In this case, when L 2 or L 3 is bonded to R 1 or R 2 of the chemical formula 2, the organic light-emitting device using a compound in which R 1 or R 2 which is not bonded is hydrogen is excluded from the present invention because the voltage is high, the efficiency is low, and the lifetime characteristics are poor, as compared with the organic light-emitting device using a compound represented by the chemical formula 1, as can be confirmed in the comparative example described later.
In the above chemical formula 1, preferably, each of L 1 to L 3 is independently a single bond, phenylene, biphenyldiyl or naphthylene.
More preferably, each of L 1 to L 3 is independently a single bond, or any one selected from the following groups:
Preferably, a is phenanthryl, triphenylene, dibenzofuranyl or dibenzothiophenyl, wherein the above a is unsubstituted or substituted with 1 to 3 substituents each independently selected from C 1-20 alkyl and C 6-60 aryl.
More preferably, a is represented by any one of the following chemical formulas a1 to a4.
In the above chemical formulas a1 to a4,
Each R is independently hydrogen or C 6-20 aryl.
At this time, 2R in the chemical formulas a3 and a4 may be the same or different from each other, for example, R are each independently hydrogen, phenyl or naphthyl.
Preferably, in the above chemical formula 2, R 1 to R 3 not bonded to L 2 or L 3 are each independently hydrogen, deuterium, C 1-10 alkyl or C 6-20 aryl, and n is 1,2 or 3. In this case, when n is 2 or more, R 3 are the same or different from each other.
More preferably, the substituent represented by the above chemical formula 2 is represented by any one of the following chemical formulas b1 to b 3:
in the above formulas b1 to b3,
X is O or S, and the X is O or S,
R 1 and R 2 are each independently C 1-10 alkyl or C 6-20 aryl,
R 3 and R 1 'to R 3' are each independently hydrogen, C 1-10 alkyl, C 6-20 aryl, or C 2-20 heteroaryl containing a heteroatom O or S, and 2R 3 in formula b2 may be the same or different from each other.
Most preferably, in the above formulas b1 and b2,
R 1 is methyl, ethyl, phenyl, biphenyl or naphthyl,
R 2 is methyl, ethyl, phenyl or biphenyl,
R 3 is each independently hydrogen, methyl or phenyl,
In the above-mentioned chemical formula b3,
R 1 'to R 3' are each independently hydrogen, methyl, isopropyl, naphthyl, phenyl or dibenzothienyl.
Preferably, ar is a substituent represented by the above chemical formula 2; any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spiro [ cyclopentane-1, 9 '-fluorenyl ] group and spiro [ cyclohexane-1, 9' -fluorenyl ] group; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl and carbazolyl,
Wherein the above aryl or heteroaryl groups are each independently unsubstituted or substituted with 1 to 5 substituents each independently selected from deuterium, C 1-10 alkyl and C 6-20 aryl.
More preferably, the above aryl or heteroaryl groups are each independently unsubstituted or substituted with 1 to 5 substituents each independently selected from deuterium, methyl and phenyl.
Most preferably, ar is any one selected from the following groups:
Of the above-mentioned groups, the group,
Y is O, S, N (phenyl) or C (methyl) 2.
Preferably, the above compound is represented by any one of the following chemical formulas 1-1 to 1-6:
In the above chemical formulas 1-1 to 1-6,
The description of L 1 to L 3, B and Ar is the same as that defined in the above chemical formula 1,
Q is O or S, and the total number of the components is O or S,
R is hydrogen, phenyl or naphthyl.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
/>
/>
/>
On the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1. The above-described production method can be more specifically described in the production example described later.
[ Reaction type 1]
In the above reaction formula 1, each X' is independently halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description.
Step 1-1 is a step of producing an intermediate compound X (int.x) by introducing an SM2 radical into a primary amine of a starting material SM1, and step 1-2 is a step of producing a compound represented by the above chemical formula 1 as a tertiary amine compound by introducing an SM3 radical into a secondary amine of the intermediate compound X (int.x). Steps 1-1 and 1-2 above are both carried out by a Buchwald-Hartmay (Buchwald-Hartwig) reaction, which are preferably carried out in the presence of a palladium catalyst. Such a manufacturing method can be more concretely described in a manufacturing example described later.
Organic light emitting device
In another aspect, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of 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 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.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of 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, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller or larger number of organic layers.
The organic light-emitting device according to the present invention may have a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on a substrate. The organic light-emitting device according to the present invention may have a reverse structure (inverted type (INVERTED TYPE)) in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjustment layer 8, a light-emitting layer 4, an electron adjustment layer 9, an electron injection and transport layer 5, and a cathode 6. In the above-described structure, the compound represented by the above chemical formula 1 may be contained in the hole transport layer, the hole adjustment layer, or both the hole transport layer and the hole adjustment layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor deposited on the organic layer. 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.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a 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, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material 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); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred 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; a multilayer structure such as LiF/Al or LiO 2/Al, but not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include 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, but are not limited thereto.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. As the hole transporting substance, the compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, or the like may be used, but the present invention is not limited thereto.
The hole regulating layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and the hole transport layer is preferably provided so as to be in contact with the light emitting layer, thereby improving the efficiency of the organic light emitting device by adjusting the hole mobility, preventing excessive migration of electrons and increasing the probability of hole-electron bonding. The hole-regulating layer contains a hole-regulating substance, and as an example of such a hole-regulating substance, a compound represented by the above chemical formula 1, an arylamine-based organic substance, or the like may be used, but is not limited thereto.
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 preferably has high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); 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.
The light emitting layer may include a host material and a dopant material as described above. The host material may further contain an aromatic condensed ring derivative, a heterocyclic compound, or the like. 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.
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 arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a 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 more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino 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.
The above-mentioned electronic regulating layer means the following layer: the organic light-emitting device is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and has an effect of improving the efficiency of the organic light-emitting device by adjusting electron mobility, preventing excessive migration of holes, and increasing the probability of hole-electron bonding. The electron mediator layer contains an electron mediator, and as examples of such electron mediator, triazine derivatives, triazole derivatives, triazine derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from the electrode and transports the received electrons to the light emitting layer and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the electron modulation layer. Such an electron injection and transport substance is a substance that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a substance having a large mobility of electrons. Examples of the specific electron injection and transport substance include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole (S),The compounds are used together with diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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 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.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated 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.
Synthesis example 1: manufacture of substituents
In order to introduce the substituent represented by the above chemical formula 2 into the compound represented by the above chemical formula 1, intermediate compounds int.(b 1), int.(b 2) and int.(b 3) were produced using the following reaction formulae 2-1, 2-2 and 2-3, respectively.
[ Reaction type 2-1]
In the above reaction formula 2-1, X' is halogen, and the description of the remaining substituents is the same as that described above. The step 2-1a is a step of introducing a bromo group into the starting material SM1 (b 1), and the step 2-1b is a step of introducing a linking group by a suzuki coupling reaction, thereby producing the intermediate compound int. (b 1). However, when L 2 is a single bond, step 2-1b may be omitted. The specific manufacturing method is as follows.
1) Step 2-1a: production of intermediate compound SM2 (b 1)
After SM1 (b 1) (1 equivalent) was dissolved in THF (excess), 2.5M N-BuLi (1 equivalent) was added dropwise after the temperature was lowered to-78℃and the mixture was stirred for 3 hours, and then N-bromosuccinimide (1 equivalent) was added. Then, the reaction mixture was heated to room temperature and stirred for 10 hours, and 1N HCl (excess) was added to terminate the reaction. After the completion of the reaction, the solvent was removed by layer separation, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the title compound was produced.
2) Step 2-1b: production of intermediate compound int. (b 1)
After SM2 (b 1) (1 equivalent) and SM3 (1.02 equivalent) were added to tetrahydrofuran (excess), 2M aqueous potassium carbonate (30 vol% based on THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed to conduct layer separation. After removal of the solvent, vacuum distillation and recrystallization from ethyl acetate and hexane gave the title compound.
[ Reaction type 2-2]
In the above reaction formula 2-2, X' is halogen, and the description of the remaining substituents is the same as that described above. The above step 2-2a is a step of introducing a bromo group into the starting material SM1 (b 2), and the above step 2-2b is a step of introducing a linking group by a suzuki coupling reaction, thereby producing the intermediate compound int. (b 2). However, when L 2 is a single bond, step 2-2b may be omitted. The specific manufacturing method is as follows:
1) Step 2-2a: production of intermediate compound SM2 (b 2)
After SM1 (b 2) (1 equivalent) was dissolved in DMF (excess), the temperature was lowered to 0℃and after stabilization, N-bromosuccinimide (1 equivalent) was added. Then, the reaction mixture was heated to room temperature, stirred for 1 hour, and then 1N HCl (excess) was added to terminate the reaction. After the completion of the reaction, the solvent was removed by layer separation, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the title compound was obtained.
2) Step 2-2b: production of intermediate compound int. (b 2)
The title compound was obtained in the same manner as in the above-described step 2-1b except that SM2 (b 2) was used as the starting material in place of SM2 (b 1) in the above-described step 2-1 b.
[ Reaction type 2-3]
In the above reaction formulae 2 to 3, X' is halogen, and the description of the remaining substituents is the same as that described above. The above step 2-3 is a step of introducing a linking group by a suzuki coupling reaction to produce the intermediate compound int. (b 3). In this case, starting material SM1 (b 3) can be produced by a method known from journals "Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists(Journal of Medicinal Chemistry,1997,vol.40,#3,p.322-330)" and "Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals(Tetrahedron,2015,vol.71,#29,p.4835-4841)", etc., and when L 2 is a single bond, step 2-3 can be omitted. The specific manufacturing method is as follows.
1) Step 2-3: production of intermediate compound int. (b 3)
The title compound was obtained in the same manner as in the above-described step 2-1b except that SM1 (b 3) was used as the starting material instead of SM2 (b 1) in the above-described step 2-1 b.
Using the methods of the above equations 2-1 to 2-3, the intermediate compounds of the following table 1 were obtained, and the respective yields and MS data are shown below.
TABLE 1
/>
/>
Synthesis example 2: production of Compounds 1 to 21 represented by chemical formula 1
The compound represented by the above chemical formula 1 is produced by the following reaction formula 1.
[ Reaction type 1]
In the above reaction formula 1, each X' is independently halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description. The specific manufacturing method is as follows.
1) Step 1-1: production of intermediate compounds INT.X (X1 to X21)
SM1 (1 equivalent), SM2 (1.02 equivalent), and sodium t-butoxide (1.4 equivalent) were added to xylene, and after heating and stirring, the mixture was refluxed, and [ bis (tri-t-butylphosphine) ] palladium (1 mol%) was added. Then, the temperature was lowered to normal temperature, and after completion of the reaction, recrystallization was performed using tetrahydrofuran and ethyl acetate, whereby the intermediate compounds X1 to X21 of table 2 below were obtained, and the respective yields and MS data are shown below.
TABLE 2
/>
/>
/>
2) Step 1-2: production of final Compounds 1 to 21
Intermediate compounds int.x (1 eq) and SM3 (1.02 eq), sodium t-butoxide (1.4 eq) were added to xylene, heated, stirred and then refluxed, and [ bis (tri-t-butylphosphine) ] palladium (1 mol%) was added. Then, the temperature was lowered to normal temperature, and after completion of the reaction, recrystallization was performed using tetrahydrofuran and ethyl acetate, whereby the following final compounds 1 to 21 were obtained, and the respective yields and MS data are shown in table 3.
/>
TABLE 3
Synthesis example 3: production of Compound 22 represented by chemical formula 1
The final compound 22 represented by the above chemical formula 1, in which the substituents-L 2 -B and-L 3 -Ar are the same, is produced by the following reaction formula 1'.
[ Reaction type 1]
In the above reaction formula 1', X' is halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description. Specifically, the final compound 22 was obtained in the same manner as in step 1-1 of synthesis example 2, and the yield and MS data are shown in table 4.
TABLE 4
Example 1: OLED fabrication
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was distilled water filtered twice using a Filter (Filter) manufactured by millbore co., ltd. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazabenzophenanthrene, hexanitrile hexaazatriphenylene) was depositedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, compound 1/>, which was synthesized in Synthesis example 2 above, was used as a hole-transporting substanceAfter vacuum deposition, HT2 is deposited as film thickness/>, on the hole transport layerVacuum evaporation was performed to form a hole adjusting layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were mixed to form a light-emitting layerVacuum evaporation was performed on the thickness of (c).
Then, E1 compoundAfter vapor deposition was performed to form an electronic control layer, an E2 compound and Liq were vapor deposited at a ratio (wt%) of 1:1Thereby sequentially performing thermal vacuum evaporation as an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added as/>To aluminium/>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance/>Vapor deposition rate per second, aluminum maintenance/>Vapor deposition rate per second.
Examples 2 to 7 and comparative examples 1 to 3
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 5 below was used instead of the compound 1 used in the hole transport layer.
The compounds used in the above examples and comparative examples are shown below.
/>
Experimental example 1
When current was applied to the organic light emitting devices manufactured in examples 1 to 7 and comparative examples 1 to 3 described above, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 5 below. At this time, T95 means a time required for the luminance to decrease from the initial luminance to 95%.
TABLE 5
As shown in table 5 above, it was confirmed that the organic light-emitting device using the compound of the present invention as a hole transport layer substance smoothly injected into the light-emitting layer by holes and the balance of holes and electrons of the organic light-emitting device according to the chemical structure, thereby exhibiting excellent characteristics in terms of driving voltage, efficiency and lifetime as compared with the organic light-emitting device using the compound of the comparative example as a hole transport layer substance.
Example 8: OLED fabrication
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of feiher company, and the distilled water was distilled water filtered twice by a filter manufactured by milbo company. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazabenzophenanthrene, hexanitrile hexaazatriphenylene) was depositedAnd performing thermal vacuum evaporation to form a hole injection layer. HT1/>, which is a hole transporting substance, on the hole injection layerAfter vacuum deposition, the compound 2 synthesized in the above synthesis example 2 was deposited on the hole transport layer as film thickness/>Vacuum evaporation was performed to form a hole adjusting layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were mixed to form a light-emitting layerVacuum evaporation was performed on the thickness of (c).
Then, E1 compoundAfter vapor deposition was performed to form an electronic control layer, an E2 compound and Liq were vapor deposited at a ratio (wt%) of 1:1Thereby sequentially performing thermal vacuum evaporation as an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added as/>To aluminium/>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance/>Vapor deposition rate per second, aluminum maintenance/>Vapor deposition rate per second.
Examples 9 to 29 and comparative examples 4 to 7
An organic light-emitting device was manufactured in the same manner as in example 8 above, except that the compound described in table 6 below was used instead of the compound HT1 used in the hole transport layer and the compound 2 used in the hole adjustment layer.
Experimental example 2
When electric current was applied to the organic light emitting devices manufactured in examples 8 to 29 and comparative examples 4 to 7 described above, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 6 below. At this time, T95 means a time required for the luminance to decrease from the initial luminance to 95%.
TABLE 6
/>
As shown in table 6 above, it was confirmed that the organic light emitting device using the compound of the present invention as a hole adjusting layer substance or as both a hole adjusting layer substance and a hole transporting layer substance exhibited excellent characteristics in terms of driving voltage, efficiency and lifetime as compared to the organic light emitting device using the compound of the comparative example, by smoothly injecting holes into the light emitting layer and balancing holes and electrons of the organic light emitting device according to the chemical structure.
[ Description of the symbols ]
1: Substrate 2: anode
3: Hole transport layer 4: light-emitting layer
5: Electron injection and transport layer 6: cathode electrode
7: Hole injection layer 8: hole regulating layer
9: An electronically modulating layer.
Claims (8)
1. A compound represented by the following chemical formula 1:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 is a single bond, phenylene or naphthylene,
L 2 and L 3 are single bonds; or a phenylene group, or a combination of the two,
A is phenanthryl or triphenylene,
Wherein A is optionally substituted with 1 or more substituents each independently selected from C 1-20 alkyl and C 6-20 aryl,
B is a substituent represented by the following chemical formula 2,
Ar is any one selected from the following groups:
Wherein Y is N (phenyl) or C (methyl) 2,
Chemical formula 2
In the chemical formula 2 described above, the chemical formula,
X is O or S, and the X is O or S,
One of R 1 to R 3 is combined with L 2, and the others are each independently hydrogen; deuterium; c 1-10 alkyl; or a C 6-20 aryl group, which is a group,
But in the case where L 2 is bound to R 1 or R 2, the unbound R 1 or R 2 is not hydrogen,
N is 1.
2. The compound of claim 1, wherein each of L 2 to L 3 is independently a single bond.
3. The compound according to claim 1, wherein a is represented by any one of the following chemical formulas a1 to a 2:
in the chemical formulas a1 to a2,
Each R is independently hydrogen or C 6-20 aryl.
4. The compound according to claim 1, wherein the substituent represented by the chemical formula 2 is represented by any one of the following chemical formulas b1 to b 3:
in the chemical formulas b1 to b3,
X is O or S, and the X is O or S,
R 1 and R 2 are each independently C 1-10 alkyl or C 6-20 aryl,
R 1 'to R 2' are each independently hydrogen, C 1-10 alkyl, or C 6-20 aryl,
R 3 and R 3' are each independently hydrogen.
5. The compound according to claim 4, wherein, in the chemical formulas b1 and b2,
R 1 is methyl, ethyl, phenyl, biphenyl or naphthyl,
R 2 is methyl, ethyl, phenyl or biphenyl,
Each R 3 is independently hydrogen,
In the chemical formula b3 described above, the chemical formula,
R 1 'to R 2' are each independently hydrogen, methyl, isopropyl, naphthyl, or phenyl,
R 3' is hydrogen.
6. A compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-3:
In the chemical formulas 1-1 to 1-3,
The description of L 1 to L 3, B and Ar is as defined in claim 1,
In the chemical formulas 1-1 to 1-3, R is hydrogen, phenyl or naphthyl.
7. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
8. An organic light emitting device, comprising: a first electrode; a second electrode disposed 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 7.
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| KR20110134581A (en) * | 2010-06-09 | 2011-12-15 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2012051855A (en) * | 2010-09-03 | 2012-03-15 | Canon Inc | Organic compound and organic light-emitting device using the same |
| CN103797604A (en) * | 2011-09-09 | 2014-05-14 | 株式会社Lg化学 | Material for organic light-emitting device, and organic light-emitting device using same |
| KR20140087987A (en) * | 2012-12-31 | 2014-07-09 | 제일모직주식회사 | COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC LiGHT EMITTING DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LiGHT EMITTING DIODE |
| CN107667099A (en) * | 2015-05-06 | 2018-02-06 | 东进世美肯株式会社 | Compounds and the organic luminescent device for including it |
| KR20160149879A (en) * | 2015-06-19 | 2016-12-28 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| CN106883205A (en) * | 2015-09-10 | 2017-06-23 | 东进世美肯株式会社 | New compound and the organic illuminating element comprising it |
| CN107778212A (en) * | 2016-08-26 | 2018-03-09 | 北京鼎材科技有限公司 | One kind 1,5 2 substitutes naphthalene derivatives and its application |
| WO2018093107A1 (en) * | 2016-11-16 | 2018-05-24 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| CN109293645A (en) * | 2018-09-29 | 2019-02-01 | 武汉天马微电子有限公司 | Benzoheterocyclic compounds, display panel and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020166874A1 (en) | 2020-08-20 |
| CN113227063A (en) | 2021-08-06 |
| KR102665294B1 (en) | 2024-05-10 |
| KR102579367B1 (en) | 2023-09-14 |
| KR20230025838A (en) | 2023-02-23 |
| CN117143087A (en) | 2023-12-01 |
| KR20200099844A (en) | 2020-08-25 |
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