CN116965179A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN116965179A CN116965179A CN202280014856.7A CN202280014856A CN116965179A CN 116965179 A CN116965179 A CN 116965179A CN 202280014856 A CN202280014856 A CN 202280014856A CN 116965179 A CN116965179 A CN 116965179A
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- emitting device
- organic light
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- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000006165 cyclic alkyl 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
- 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
- 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
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film 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
- 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
- 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
- 125000005549 heteroarylene 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical compound [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [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
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 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
- 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
- 125000005561 phenanthryl group Chemical group 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
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 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
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 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
- 150000003839 salts Chemical class 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying 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
- 125000004434 sulfur atom Chemical group 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
- 229930192474 thiophene Natural products 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
- 230000007704 transition Effects 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- 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
- 239000008096 xylene Substances 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
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- 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
- H10K50/15—Hole 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
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- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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]
- H10K50/18—Carrier blocking layers
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- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application provides an organic light emitting device.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2021-0067128, 5.25 of 2021, the entire contents of the disclosures of which are incorporated as part of the present specification.
The present application relates to an organic light emitting device.
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. 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 (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
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
(patent document 0002) U.S. patent publication No. 2007-0196692
(patent document 0003) korean patent laid-open No. 10-2017-0048159
(patent document 0004) U.S. patent No. 6821643
Disclosure of Invention
Technical problem
The present application relates to an organic light emitting device.
Solution to the problem
The present application provides the following organic light emitting device.
An organic light emitting device, comprising:
an anode;
a light emitting layer;
a hole blocking layer;
an electron transport layer, an electron injection layer, or an electron transport and injection layer; and
a cathode electrode, which is arranged on the surface of the cathode,
the hole blocking layer contains a compound represented by the following chemical formula 1,
the above electron transport layer, electron injection layer, or electron transport and injection layer contains a compound represented by the following chemical formula 2 or 3:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 3 Each independently is N or CH, and X 1 To X 3 At least one of which is N,
L 1 to L 3 Each independently is a direct bond, or a substituted or unsubstituted C 6-60 Arylene group, ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group,
Ar 3 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
[ chemical formula 2]
[ chemical formula 3]
In the above chemical formula 2 or chemical formula 3,
R 1 to R 4 Each independently of the other is hydrogen or deuterium,
n1 to n4 are integers of 1 to 4,
L 4 and L 5 Each independently is a direct bond, or a substituted or unsubstituted C 6-60 Arylene group, ar 4 And Ar is a group 5 Each independently is a substituent represented by the following chemical formula 4,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
X 4 to X 8 Each independently is N or C (R 5 ) And X is 4 To X 8 At least two of which are N,
R 5 each independently is hydrogen; deuterium; substituted or unsubstituted C 1-20 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl, or 2R's adjacent thereto 5 And combine to form a benzene ring.
Effects of the application
The organic light emitting device described above adjusts the compounds contained in the light emitting layer and the electron transporting layer, so that an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics can be achieved in the organic light emitting device.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, a hole blocking layer 4, an electron transport and injection 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 8, an electron suppression layer 9, a light-emitting layer 3, a hole blocking layer 4, an electron transport and injection layer 5, and a cathode 6.
Detailed Description
In the following, the application will be described in more detail in order to aid understanding thereof.
In the present description of the application,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; a nitrile 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 groupArylthio->Alkylsulfonyl->Arylsulfonyl->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 comprising N, O and 1 or more of heterocyclic groups of 1 or more of S atoms is substituted or unsubstituted, or a substituent comprising 2 or more of the above-exemplified substituents is bondedSubstituted or unsubstituted. 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 application 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 fluorenyl group is substituted, it may be that
Etc. However, the present application is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinylPyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), 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, and the arylamine 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-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. 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 heterocyclic 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. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of a heterocyclic group can be applied thereto.
The present application provides an organic light emitting device, including: an anode; a hole transport layer; a light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer includes a compound represented by the chemical formula 1, and the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer includes any one or more of a compound represented by the chemical formula 2 and a compound represented by the chemical formula 3.
The organic light emitting device according to the present application adjusts the compound contained in the light emitting layer and the compound contained in the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer, so that an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics can be achieved in the organic light emitting device.
The present application will be described in detail with reference to the following configurations.
Anode and cathode
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); 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.
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; liF/Al or LiO 2 And/or Al, but is not limited thereto.
Hole injection layer
The organic light emitting device according to the present application may include a hole injection layer between the anode and the hole transport layer as needed.
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, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
Hole transport layer
The hole-transporting layer used in the present application is a layer that receives holes from the anode or a hole-injecting layer formed on the anode and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer is suitable, 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.
Electron suppression layer
The organic light emitting device according to the present application may include an electron suppressing layer between the hole transporting layer and the light emitting layer as needed. The electron suppression layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and improving the probability of hole-electron bonding. The electron-inhibiting layer contains an electron-inhibiting substance, and as an example of such an electron-inhibiting substance, an arylamine-based organic substance or the like can be used, but the electron-inhibiting substance is not limited thereto.
Light-emitting layer
The light-emitting substance included in the light-emitting layer 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. 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.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and 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 application is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
Hole blocking layer
The organic light emitting device according to the present application may include a hole blocking layer between the above light emitting layer and the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer as needed. Preferably, the hole blocking layer is in contact with the light emitting layer.
The hole blocking layer suppresses the transfer of holes injected from the anode to the cathode without recombination in the light emitting layer, thereby improving the efficiency of the organic light emitting device. In the present application, as a substance constituting the hole blocking layer, a compound represented by the above chemical formula 1 is used.
Preferably L 1 And L 2 Each independently is a direct bond or phenylene group, L 3 Is a direct bond, phenylene, biphenyldiyl, or terphenyldiyl group.
Preferably Ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, or naphthyl.
Preferably Ar 3 Is any one of substituents represented by the following chemical formulas 1-1 to 1-7:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
In the above chemical formulas 1-1 to 1-7,
R 6 and R is 7 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-60 Aryl, Z is each independently NR 9 O, or S, R 8 And R is 9 Each independently is a substituted or unsubstituted C 6-60 Aryl groups.
Preferably, R 6 And R is 7 Each independently is hydrogen, deuterium, methyl, or substituted or unsubstituted phenyl, R 8 And R is 9 Is phenyl.
Preferably Ar 3 Is any one selected from the group consisting of:
representative examples of the compounds represented by the above chemical formula 1 are shown below:
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the present application also provides a method for producing a compound represented by the above chemical formula 1, which is represented by the following chemical formula 1.
[ reaction type 1]
In the above reaction formula 1, X 1 To X 3 、L 1 To L 3 And Ar 1 To Ar 3 As defined above, Z is halogen, preferably bromine or chlorine.
The above-described production method can be more specifically described in the production example described later.
An electron transport layer, an electron injection layer, or an electron transport and injection layer
The organic light emitting device according to the present application may include an electron transport layer, an electron injection layer, or an electron transport and injection layer between the above-described light emitting layer and the cathode.
The electron transporting layer is a layer that receives electrons from the cathode or an electron injecting layer formed on the cathode and transports the electrons to the light emitting layer, and suppresses the transfer of holes from the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light emitting layer, and in the present application, any one or more of the compound represented by the above chemical formula 2 and the compound represented by the chemical formula 3 may be contained.
The electron injection layer is a layer that injects electrons from an electrode, and may contain any one or more of the compound represented by chemical formula 2 and the compound represented by chemical formula 3 as a compound that 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, prevention of migration of excitons generated in the light-emitting layer to a hole injection layer, and excellent thin film formation ability.
The electron transporting and injecting layer is a layer that performs electron transporting and injecting simultaneously, and may include a compound represented by the above chemical formula 2 or 3.
Preferably, the above chemical formula 2 is represented by the following chemical formula 2-1, and the above chemical formula 3 is represented by the following chemical formula 3-1.
[ chemical formula 2-1]
[ chemical formula 3-1]
In the above chemical formula 2-1 or chemical formula 3-1Wherein L is 4 、L 5 、Ar 4 And Ar is a group 5 The same definition as above.
Preferably L 4 And L 5 Each independently is a direct bond, phenylene, or biphenyldiyl.
Preferably Ar 4 And Ar is a group 5 Each independently is any one selected from the group consisting of:
in the above group, R 5 The same definition as above.
Preferably, R 5 Each independently is hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl, or thienyl, or 2R's adjacent thereto 5 And are bonded to form a benzene ring, and each of the phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl, or thienyl is independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.
Preferably Ar 4 And Ar is a group 5 Each independently is any one selected from the group consisting of:
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representative examples of the compounds represented by the above chemical formulas 2 or 3 are shown below:
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the present application also provides a method for producing a compound represented by the above chemical formula 2 or 3, as shown in the following reaction formulas 2 to 5.
[ reaction type 2]
[ reaction type 3]
[ reaction type 4]
[ reaction type 5]
In the above equations 2 to 5, L is each independently L 4 Or L 5 The method comprises the steps of carrying out a first treatment on the surface of the Ar is each independently Ar 4 Or Ar 5 The method comprises the steps of carrying out a first treatment on the surface of the R is each independently R 1 To R 4 Any one of them; each n is independently any one of n1 to n 4. In addition, L 4 、L 5 、Ar 4 、Ar 5 、R 1 To R 4 And n1 to n4 are as defined above, Z is halogen, preferably bromine or chlorine.
In addition, the electron transport layer may further include a metal complex. 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 electron injection layer may further contain a metal complex. 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).
Organic light emitting device
A structure of an organic light emitting device according to the present application is illustrated in fig. 1. Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, a hole blocking layer 4, an electron transport and injection layer 5, and a cathode 6.
Fig. 2 shows an example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 8, an electron suppression layer 9, a light-emitting layer 3, a hole blocking layer 4, an electron transport and injection layer 5, and a cathode 6.
The organic light emitting device according to the present application can be manufactured by sequentially laminating the above-described constitution. This can be manufactured as follows: PVD (physical Vapor Deposition: physical vapor deposition) methods such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) are used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then the above layers are formed on the anode, and then a substance that can be used as a cathode is deposited thereon. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material to an anode material on a substrate in reverse order of the above-described constitution (WO 2003/012890). In addition, the host and the dopant may be formed into the light-emitting layer not only by a vacuum vapor deposition method but also by a solution coating method. 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.
On the other hand, the organic light emitting device according to the present application may be a bottom emission (bottom emission) device, a top emission (top emission) device, or a bi-directional light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
In the following, preferred embodiments are presented to aid in understanding the present application. However, the following examples are provided only for easier understanding of the present application, and the content of the present application is not limited thereto.
Production example
Production example 1-1: production of Compound B1
B1-A (20 g,43.1 mmol) and B1-B (10.3 g,43.1 mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (17.9 g,129.2 mmol) was dissolved in 18ml of water and charged, and after stirring well, tetrakis (triphenylphosphine) palladium (1.5 g,1.3 mmol) was charged. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. This was again poured into 20 times 498mL of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate, thereby compound B1 (12.9 g, 52%) was produced as a white solid.
MS:[M+H] + ＝578
Production examples 1 to 2: production of Compound B2
The compound B2 was produced by the same method as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝625
Production examples 1 to 3: production of Compound B3
The compound B3 was produced in the same manner as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝617
Production examples 1 to 4: production of Compound B4
The compound B4 was produced in the same manner as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝654
Production examples 1 to 5: production of Compound B5
The compound B5 was produced in the same manner as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝653
Production examples 1 to 6: production of Compound B6
The compound B6 was produced in the same manner as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝653
Production examples 1 to 7: production of Compound B7
The compound B7 was produced in the same manner as the production method of production example 1-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝624
Production examples 1 to 8: production of Compound B8
B8-A (20 g,43.1 mmol) and B8-B (15.4 g,43.1 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, sodium t-butoxide (12.4 g,129.2 mmol) was added thereto, and after stirring thoroughly, bis (tri-t-butylphosphine) palladium (0.7 g,1.3 mmol) was added thereto. After 1 hour of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again poured into 320mL of chloroform 10 times and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, whereby yellow solid compound B8 (18.2 g, 57%) was produced.
MS:[M+H] + ＝742
Production example 2-1: production of Compound E1
E1-A (20 g,64.1 mmol) and E1-B (55.8 g,128.2 mmol) were added to tetrahydrofuran (400 ml) under nitrogen, stirred and refluxed. Then, potassium carbonate (26.6 g,192.3 mmol) was dissolved in water (27 ml) and then charged with well-stirred, and then, tetrakis (triphenylphosphine) palladium (2.2 g,1.9 mmol) was charged. After 1 hour of reaction, the mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again poured into chloroform (20 times, 986 mL) and dissolved, after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to yield compound E1 (32.5 g, 66%) as a white solid.
MS:[M+H] + ＝769
Production example 2-2: production of Compound E2
The compound E2 was produced by the same method as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝767
Production example 2-3: production of Compound E3
The compound E3 was produced by the same method as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝715
Production examples 2 to 4: production of Compound E4
The compound E4 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝615
Production examples 2 to 5: production of Compound E5
The compound E5 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction formula.
MS:[M+H] + ＝619
Production examples 2 to 6: production of Compound E6
The compound E6 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝715
Production examples 2 to 7: production of Compound E7
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The compound E7 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝919
Production examples 2 to 8: production of Compound E8
E8-A (20 g,47.6 mmol) and E8-B (28 g,47.6 mmol) were added to 1, 4-di-under nitrogenThe mixture was stirred and refluxed in an alkane (1, 4-Dioxane). Then, potassium phosphate (30.3 g,142.9 mmol) was dissolved in water (30 ml) and then, after stirring thoroughly, dibenzylideneacetone palladium (0.8 g,1.4 mmol) and tricyclohexylphosphine (0.8 g,2.9 mmol) were added. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was poured into chloroform (30 times, 1207 mL) and dissolved, after washing with water 2 times, the organic layer was separated, 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 compound E8 (6 g, 15%) as a white solid.
MS:[M+H] + ＝845
Production examples 2 to 9: production of Compound E9
The above-mentioned compound E9 was produced by the same method as the production methods of production examples 2 to 8, except that each starting material was used as in the above-mentioned reaction formula.
MS:[M+H] + ＝769
Production examples 2 to 10: production of Compound E10
The above-mentioned compound E10 was produced by the same method as the production methods of production examples 2 to 8, except that each starting material was used as in the above-mentioned reaction formula.
MS:[M+H] + ＝843
Production examples 2 to 11: production of Compound E11
The compound E11 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝769
Production examples 2 to 12: production of Compound E12
The compound E12 was produced by the same method as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝715
Production examples 2 to 13: production of Compound E13
The compound E13 was produced in the same manner as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝795
Production examples 2 to 14: production of Compound E14
The compound E14 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝869
Production examples 2 to 15: production of Compound E15
The compound E15 was produced in the same manner as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝919
Production examples 2 to 16: production of Compound E16
The above-mentioned compound E16 was produced by the same method as the production methods of production examples 2 to 8, except that each starting material was used as in the above-mentioned reaction formula.
MS:[M+H] + ＝768
Production examples 2 to 17: production of Compound E17
The above-mentioned compound E17 was produced by the same method as the production methods of production examples 2 to 8, except that each starting material was used as in the above-mentioned reaction formula.
MS:[M+H] + ＝845
Production examples 2 to 18: production of Compound E18
The above-mentioned compound E18 was produced by the same method as the production methods of production examples 2 to 8, except that each starting material was used as in the above-mentioned reaction formula.
MS:[M+H] + ＝775
Production examples 2 to 19: production of Compound E19
The compound E19 was produced in the same manner as the production method of production example 2-1, except that each starting material was used in the above reaction scheme.
MS:[M+H] + ＝921
Production examples 2 to 20: production of Compound E20
The compound E20 was produced in the same manner as the production method of production example 2-1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝919
Examples (example)
Example 1
To ITO (indium tin oxide)The 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. In addition, oxygen plasma is utilized to makeAfter the substrate was cleaned 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,) 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.
The compound B1 is applied on the light-emitting layer to form a light-emitting layerAnd performing thermal vacuum evaporation to form a hole blocking layer. On the hole blocking layer, the compound E1 and the following compound [ LiQ ]](lithium quinoline) vacuum evaporation was performed at a weight ratio of 1:1, thereby +.>Form 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 cathode/sec->Vapor deposition rate per second, aluminum maintenance->Vapor deposition rate per second, vacuum degree was maintained at 1×10 during vapor deposition -7 ～5×10 -8 The support is thus fabricated into an organic light emitting device.
Examples 2 to 160
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 B1 or the compound E1.
Comparative examples 1 to 191
An organic light emitting device was manufactured by the same method as in example 1, except that the compound of table 1 below was used instead of the compound B1 or the compound E1. The compounds of ET-1 to ET-19 used in table 1 below are shown below.
The organic light-emitting devices manufactured in the above examples and comparative 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
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As described in table 1 above, the compound represented by chemical formula 1 of the present application can be used for an organic layer corresponding to a hole blocking layer of an organic light emitting device.
As described in table 1 above, the compound represented by chemical formula 2 or chemical formula 3 of the present application can be used for an organic layer of an organic light-emitting device capable of simultaneously performing electron transport and electron injection.
Comparing the above-described experimental examples 1 to 160 of table 1 with comparative experimental examples 1 to 20, it was confirmed that the organic light emitting device including the compound represented by chemical formula 1 and the heterocyclic compound represented by chemical formula 2 or 3 of the present application showed significantly superior characteristics in efficiency and lifetime compared to the organic light emitting device including no compound of chemical formula 1.
Comparing experimental examples 1 to 160 of table 1 with comparative experimental examples 21 to 191, it was confirmed that the organic light emitting device including the compound represented by chemical formula 1 and the heterocyclic compound represented by chemical formula 2 or 3 of the present application showed significantly superior characteristics in efficiency and lifetime compared to the organic light emitting device not including the heterocyclic compound represented by chemical formula 2 or 3.
[ description of the symbols ]
1: substrate 2: anode
3: light emitting layer 4: hole blocking layer
5: electron transport and injection layer 6: cathode electrode
7: hole injection layer 8: hole transport layer
9: an electron suppression layer.
Claims (13)
1. An organic light emitting device comprising:
an anode;
a light emitting layer;
a hole blocking layer;
an electron transport layer, an electron injection layer, or an electron transport and injection layer; and
a cathode electrode, which is arranged on the surface of the cathode,
wherein the hole blocking layer comprises a compound represented by the following chemical formula 1,
wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer comprises a compound represented by the following chemical formula 2 or 3:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
X 1 to X 3 Each independently is N or CH, and X 1 To X 3 At least one of which is N,
L 1 to L 3 Each independently is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group,
Ar 3 is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
[ chemical formula 2]
[ chemical formula 3]
In the chemical formula 2 or 3 described above,
R 1 to R 4 Each independently of the other is hydrogen or deuterium,
n1 to n4 are integers of 1 to 4,
L 4 and L 5 Each independently is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 4 and Ar is a group 5 Each independently is a substituent represented by the following chemical formula 4,
[ chemical formula 4]
In the chemical formula 4 described above, the chemical formula,
X 4 to X 8 Each independently of the otherIs N or C (R) 5 ) And X is 4 To X 8 At least two of which are N,
R 5 each independently is hydrogen; deuterium; substituted or unsubstituted C 1-20 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl, or 2 adjacent R 5 And combine to form a benzene ring.
2. The organic light-emitting device of claim 1, wherein L 1 And L 2 Each independently is a direct bond or phenylene,
L 3 is a direct bond, phenylene, biphenyldiyl, or terphenyldiyl group.
3. The organic light-emitting device of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, or naphthyl.
4. The organic light-emitting device of claim 1, wherein Ar 3 Is any one of substituents represented by the following chemical formulas 1-1 to 1-7:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
In the chemical formulas 1-1 to 1-7,
R 6 and R is 7 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-60 An aryl group,
z is each independently NR 9 O, or S,
R 8 and R is 9 Each independently is a substituted or unsubstituted C 6-60 Aryl groups.
5. The organic light-emitting device of claim 4, wherein R 6 And R is 7 Each independently hydrogen, deuterium, methyl, or substituted or unsubstituted phenyl,
R 8 and R is 9 Is phenyl.
6. The organic light-emitting device of claim 1, wherein Ar 3 Is any one selected from the group consisting of:
7. the organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
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8. the organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by the following chemical formula 2-1,
the chemical formula 3 is represented by the following chemical formula 3-1:
[ chemical formula 2-1]
[ chemical formula 3-1]
In the chemical formula 2-1 or chemical formula 3-1,
L 4 、L 5 、Ar 4 and Ar is a group 5 As defined in claim 1.
9. The organic light-emitting device of claim 1, wherein L 4 And L 5 Each independently is a direct bond, phenylene, or biphenyldiyl.
10. The organic light-emitting device of claim 1, wherein Ar 4 And Ar is a group 5 Each independently is any one selected from the group consisting of:
in the group of the two-dimensional objects,
R 5 as defined in claim 1.
11. The organic light-emitting device of claim 1, wherein R 5 Each independently is hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, furyl, or thienyl, or 2 adjacent R' s 5 To form a benzene ring by combination,
the phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, furanyl, or thiophenyl groups are each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.
12. The organic light-emitting device of claim 1, wherein Ar 4 And Ar is a group 5 Each independently is any one selected from the group consisting of:
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13. the organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 2 or 3 is any one selected from the group consisting of:
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| KR1020210067128A KR20220163537A (en) | 2021-05-25 | 2021-05-25 | Organic light emitting device |
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| PCT/KR2022/007243 WO2022250386A1 (en) | 2021-05-25 | 2022-05-20 | Organic light-emitting device |
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