KR102600009B1 - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
- Publication number
- KR102600009B1 KR102600009B1 KR1020220096679A KR20220096679A KR102600009B1 KR 102600009 B1 KR102600009 B1 KR 102600009B1 KR 1020220096679 A KR1020220096679 A KR 1020220096679A KR 20220096679 A KR20220096679 A KR 20220096679A KR 102600009 B1 KR102600009 B1 KR 102600009B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- light emitting
- layer
- organic light
- compound
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005165 aryl thioxy group 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
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 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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- 239000011651 chromium Substances 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
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- 230000008025 crystallization Effects 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
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- 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
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
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- 238000000295 emission spectrum Methods 0.000 description 1
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- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
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- 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
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- 125000001153 fluoro group Chemical group F* 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
- 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
- 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
- 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-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
- 150000002503 iridium Chemical class 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
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 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
- 125000004433 nitrogen atom Chemical group N* 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
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-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
- 150000005041 phenanthrolines 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
- 150000003057 platinum Chemical class 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-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
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 229910052710 silicon 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 유기 발광 소자를 제공한다. The present invention provides an organic light emitting device.
Description
본 발명은 구동 전압이 낮고, 발광 효율이 높으며, 수명이 우수한 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device with low driving voltage, high luminous efficiency, and excellent lifespan.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in organic light-emitting devices as described above is continuously required.
본 발명은 구동 전압이 낮고, 발광 효율이 높으며, 수명이 우수한 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device with low driving voltage, high luminous efficiency, and excellent lifespan.
상기 과제를 해결하기 위하여, 본 발명은 하기의 유기 발광 소자를 제공한다.In order to solve the above problems, the present invention provides the following organic light emitting device.
본 발명에 따른 유기 발광 소자는,The organic light emitting device according to the present invention,
양극; anode;
상기 양극에 대향하여 구비된 음극;a cathode provided opposite the anode;
상기 양극과 음극 사이에 구비된 발광층;A light emitting layer provided between the anode and the cathode;
상기 양극과 발광층 사이에 구비된 정공수송영역; 및A hole transport area provided between the anode and the light emitting layer; and
상기 발광층과 음극 사이에 구비된 전자수송영역을 포함하고,It includes an electron transport region provided between the light emitting layer and the cathode,
상기 전자수송영역은 하기 화학식 1로 표시되는 제1 화합물을 포함하고,The electron transport region includes a first compound represented by the following formula (1),
상기 발광층은 하기 화학식 2로 표시되는 제2 화합물을 포함하고,The light-emitting layer includes a second compound represented by the following formula (2),
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
X1 내지 X3는 각각 독립적으로, N 또는 CH이되, X1 내지 X3 중 적어도 하나는 N이고,X 1 to X 3 are each independently N or CH, but at least one of X 1 to X 3 is N,
L1은 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고,L 1 is a single bond; Substituted or unsubstituted C 6-60 arylene; or a C 2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
L2 및 L3는 각각 독립적으로, 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고,L 2 and L 3 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; or a C 2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
Ar3 및 Ar4는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
R은 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 카바졸일; 치환 또는 비치환된 디벤조퓨라닐; 또는 치환 또는 비치환된 디벤조티오페닐이다.R is substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted dibenzofuranyl; Or substituted or unsubstituted dibenzothiophenyl.
상술한 유기 발광 소자는 발광층과 전자수송영역 각각에 특정 구조의 화합물을 각각 포함하여, 낮은 구동 전압, 높은 발광 효율 및 장수명 특성을 나타낼 수 있다. The above-described organic light-emitting device includes compounds of a specific structure in each of the light-emitting layer and the electron transport region, and can exhibit low driving voltage, high luminous efficiency, and long lifespan characteristics.
도 1은 기판(10), 양극(20), 정공수송영역(30), 발광층(40), 전자수송영역(50) 및 음극(60)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판(10), 양극(20), 정공수송영역(30), 발광층(40), 전자수송영역(50) 및 음극(60)으로 이루어지고, 상기 정공수송영역(30)은 양극(20)으로부터 차례로 적층된 정공주입층(31), 정공수송층(33) 및 전자차단층(35)을 구비하고, 상기 전자수송영역(50)은 발광층(40)으로부터 차례로 적층된 정공차단층(51), 전자수송층(53) 및 전자주입층(55)을 구비한 유기 발광 소자의 예를 도시한 것이다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60.
Figure 2 consists of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60, and the hole transport region 30 is an anode ( A hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20), and the electron transport region 50 is a hole blocking layer 51 stacked sequentially from the light emitting layer 40. ), shows an example of an organic light-emitting device having an electron transport layer 53 and an electron injection layer 55.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid understanding.
본 명세서에서, 및 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에, 한정되는 것은 아니다. In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에, 한정되는 것은 아니다.In this specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be straight chain or branched, 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 include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에, 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 비페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난쓰레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 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 a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, It can be etc. However, it is not limited to this.
본 명세서에 있어서, 헤테로아릴은 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로아릴로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as a heteroelement, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group group, phenothiazinyl group, and dibenzofuranyl group, but are not limited to these.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다.In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding heteroaryl described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of heteroaryl described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of heteroaryl described above can be applied, except that the heterocycle is not monovalent and is formed by combining two substituents.
본 발명은 하기 구조를 갖는 유기 발광 소자를 제공한다:The present invention provides an organic light-emitting device having the following structure:
양극; anode;
상기 양극에 대향하여 구비된 음극;a cathode provided opposite the anode;
상기 양극과 음극 사이에 구비되고, 상기 제2 화합물을 포함하는 발광층;a light emitting layer provided between the anode and the cathode and containing the second compound;
상기 양극과 발광층 사이에 구비된 정공수송영역; 및A hole transport area provided between the anode and the light emitting layer; and
상기 발광층과 음극 사이에 구비되고, 상기 제1 화합물을 포함하는 전자수송영역.An electron transport region provided between the light emitting layer and the cathode and including the first compound.
이하, 각 구성 별로 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail for each configuration.
양극 및 음극anode and cathode
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SNO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
정공수송영역Hole transport area
본 발명에 따른 유기 발광 소자는 양극과 발광층 사이에 구비된 정공수송영역을 포함한다. 상기 정공수송영역은 양극으로부터 정공을 수취하여 발광층까지 정공을 수송하는 영역으로, 정공에 대한 이동성이 큰 물질을 포함하는 것이 적합하다. 바람직하게는, 상기 정공수송영역은 상기 양극으로부터 차례로 적층되어 있는 정공주입층, 정공수송층 및 전자차단층을 포함한다. The organic light emitting device according to the present invention includes a hole transport region provided between the anode and the light emitting layer. The hole transport region is a region that receives holes from the anode and transports the holes to the light-emitting layer, and is preferably made of a material with high mobility for holes. Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked from the anode.
(정공주입층)(hole injection layer)
상기 정공주입층은 상기 양극 상에 위치하여, 양극으로부터 정공을 주입하는 층으로, 정공 주입 물질을 포함한다. 이러한 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 특히, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 적합하다.The hole injection layer is located on the anode, is a layer that injects holes from the anode, and includes a hole injection material. These hole injection materials have the ability to transport holes and have an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. A compound that prevents and has excellent thin film forming ability is preferred. In particular, it is suitable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
상기 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrilehexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene. These include, but are not limited to, series of organic materials, anthraquinone, polyaniline, and polythiophene series of conductive polymers.
(정공수송층)(Hole transport layer)
상기 정공수송층은 상기 정공주입층 상에 형성되어, 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 역할을 한다. 상기 정공수송층은 정공 수송 물질을 포함하고, 이러한 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 정공에 대한 이동성이 큰 물질이 적합하다. The hole transport layer is formed on the hole injection layer, and serves to receive holes from the hole injection layer and transport the holes to the light emitting layer. The hole transport layer includes a hole transport material, and a material with high mobility for holes that can transport holes from an anode or a hole injection layer and transfer them to the light emitting layer is suitable as the hole transport material.
상기 정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
(전자차단층)(electron blocking layer)
상기 전자차단층은 상기 정공수송층 상에 형성되어, 바람직하게는 발광층에 접하여 구비되어, 정공 이동도를 조절하고, 전자의 과다한 이동을 방지하여 정공-전자간 결합 확률을 높여줌으로써 유기 발광 소자의 효율을 개선하는 역할을 한다. 상기 전자차단층은 전자 차단 물질을 포함하고, 이러한 전자 차단 물질로는 발광층에서 전자가 흘러나오지 않을 수 있는 안정된 구조를 갖는 물질이 적합하다.The electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, to control hole mobility and prevent excessive movement of electrons to increase the probability of coupling between holes and electrons, thereby increasing the efficiency of the organic light emitting device. plays a role in improving. The electron blocking layer includes an electron blocking material, and a material having a stable structure that prevents electrons from flowing out of the light emitting layer is suitable as the electron blocking material.
상기 전자 차단 물질의 구체적인 예로는 아릴아민 계열의 유기물 등이 있으나, 이에 한정되는 것은 아니다. Specific examples of the electron blocking material include arylamine-based organic materials, but are not limited thereto.
발광층luminescent layer
본 발명에 따른 유기 발광 소자는 상기 화학식 2로 표시되는 제2 화합물인, 2번, 9번 및 10번 위치가 치환된 안트라센 화합물을 호스트 물질로 포함한다. 특히, 상기 제2 화합물은 9번 및 10번 위치에 동일 또는 상이한 치환기가 도입됨과 동시에 2번 위치에 치환기가 도입된 구조를 가져, 2번 위치에 치환기가 도입되지 않은 화합물에 비하여, 물질 안정성이 우수하여 유기 발광 소자에 사용 시 수명 특성 향상에 기여할 수 있다. The organic light emitting device according to the present invention includes the second compound represented by Chemical Formula 2, an anthracene compound substituted at positions 2, 9, and 10, as a host material. In particular, the second compound has a structure in which the same or different substituents are introduced at the 9th and 10th positions and at the same time a substituent is introduced at the 2nd position, so that compared to the compound without a substituent introduced at the 2nd position, the material stability is improved. It is excellent and can contribute to improving lifespan characteristics when used in organic light-emitting devices.
바람직하게는, 상기 화학식 2에서, L2 및 L3는 각각 독립적으로, 단일결합, 또는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:Preferably, in Formula 2, L 2 and L 3 may each independently be a single bond or any one selected from the group consisting of:
상기에서,In the above,
Y1은 O, S, N(C6-20 아릴), C(C1-4 알킬)2, 또는 C(C6-20 아릴)2이다.Y 1 is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
예를 들어, Y1은 O, S, N(페닐), C(메틸)2, 또는 C(페닐)2이다.For example, Y 1 is O, S, N(phenyl), C(methyl) 2 , or C(phenyl) 2 .
보다 바람직하게는, L2 및 L3는 각각 독립적으로, 단일결합, 또는 페닐렌이다. More preferably, L 2 and L 3 are each independently a single bond or phenylene.
바람직하게는, Ar3 및 Ar4는 각각 독립적으로, C6-20 아릴; 또는 O 또는 S를 포함하는 C2-60 헤테로아릴이다.Preferably, Ar 3 and Ar 4 are each independently C 6-20 aryl; or C 2-60 heteroaryl containing O or S.
보다 바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 디벤조퓨라닐, 또는 디벤조티오페닐이다.More preferably, Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.
바람직하게는, R은 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 트리페닐레닐, 플루오레닐, 카바졸일, 디벤조퓨라닐, 또는 디벤조티오페닐이고,Preferably, R is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,
여기서, R은 비치환되거나, 또는 중수소, C1-10 알킬, 트리(C1-4 알킬)실릴 및 C6-20 아릴로 구성되는 군으로부터 각각 독립적으로 선택되는 1개 내지 5개의 치환기로 치환될 수 있다.Here, R is unsubstituted or substituted with 1 to 5 substituents each independently selected from the group consisting of deuterium, C 1-10 alkyl, tri(C 1-4 alkyl)silyl, and C 6-20 aryl. It can be.
보다 바람직하게는, R은 하기로 구성되는 군으로부터 선택되는 어느 하나이다:More preferably, R is any one selected from the group consisting of:
상기에서,In the above,
Q는 수소, C1-10 알킬, Si(C1-4 알킬)3, 또는 C6-20 아릴이고,Q is hydrogen, C 1-10 alkyl, Si(C 1-4 alkyl) 3 , or C 6-20 aryl,
Y2는 O, S, N(C6-20 아릴), C(C1-4 알킬)2, 또는 C(C6-20 아릴)2이다.Y 2 is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
예를 들어, Q는 수소, tert-부틸, Si(메틸)3, 페닐, 또는 나프틸이고,For example, Q is hydrogen, tert-butyl, Si(methyl) 3 , phenyl, or naphthyl,
Y2는 O, S, N(페닐), C(메틸)2, 또는 C(페닐)2이다.Y 2 is O, S, N(phenyl), C(methyl) 2 , or C(phenyl) 2 .
바람직하게는, 상기 제2 화합물은 하기 화학식 2-1 또는 2-2로 표시된다:Preferably, the second compound is represented by the following formula 2-1 or 2-2:
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
상기 화학식 2-1 및 2-2에서,In Formulas 2-1 and 2-2,
L3, Ar4 및 R은 상기 화학식 2에서 정의한 바와 같다.L 3 , Ar 4 and R are as defined in Formula 2 above.
상기 제2 화합물의 대표적인 예는 하기와 같다:Representative examples of the second compounds are as follows:
..
..
이때, 상기 제2 화합물은 일례로 하기 반응식 2와 같은 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. At this time, the second compound can be prepared, for example, by a production method as shown in Scheme 2 below. The manufacturing method may be further detailed in the manufacturing examples described later.
[반응식 2][Scheme 2]
상기 반응식 2에서, T는 할로겐이고, 바람직하게는 브로모, 또는 클로로이고, 다른 치환기에 대한 정의는 앞서 설명한 바와 같다. In Scheme 2, T is halogen, preferably bromo or chloro, and the definitions of other substituents are as described above.
구체적으로, 상기 화학식 2로 표시되는 화합물은 스즈키 커플링 반응을 통해 출발물질에 R 치환기가 도입되어 제조된다. 이러한 스즈키 커플링 반응은 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.Specifically, the compound represented by Formula 2 is prepared by introducing an R substituent to the starting material through a Suzuki coupling reaction. This Suzuki coupling reaction is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.
한편, 상기 발광층은 도펀트 재료를 더 포함할 수 있다. 상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에, 한정되는 것은 아니다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에, 한정되는 것은 아니다. 바람직하게는, 상기 발광층은 이리듐 착체를 도펀트 재료로 포함할 수 있다. Meanwhile, the light emitting layer may further include a dopant material. The dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes. Preferably, the light emitting layer may include an iridium complex as a dopant material.
상술한 호스트 물질과 도펀트 물질을 포함하는 발광층을 구비한 유기 발광 소자는 발광스펙트럼에서의 최대파장(λmax)을 약 400 nm 내지 약 500 nm에서 나타낼 수 있다. 따라서, 상기 유기 발광 소자는 청색 발광 유기 발광 소자이다.An organic light-emitting device having a light-emitting layer containing the above-described host material and a dopant material may exhibit a maximum wavelength (λ max ) in the light emission spectrum of about 400 nm to about 500 nm. Therefore, the organic light emitting device is a blue light emitting organic light emitting device.
전자수송영역Electronic transport area
본 발명에 따른 유기 발광 소자는 상기 발광층과 음극 사이에 구비된, 음극에서 발광층까지 전자를 수송하는 전자수송영역을 포함하고, 상기 전자수송영역은 상기 화학식 1로 표시되는 제1 화합물을 포함한다.The organic light-emitting device according to the present invention includes an electron transport region provided between the light-emitting layer and the cathode, transporting electrons from the cathode to the light-emitting layer, and the electron transport region includes the first compound represented by Formula 1.
상기 제1 화합물은 전자가 풍부한 스피로[플루오렌-9,9'-잔텐) 코어에 전자 부족 치환체(electron deficient substituent)인 N 함유-6원 헤테로고리기가 결합된 구조를 가져, 낮은 쌍극자 모멘트(dipole moment) 값 및 무정형 특성을 나타낸다. 따라서, 이러한 제1 화합물을 유기 발광 소자에 채용 시, 소자 작동 시 발생하는 열로 야기될 수 있는 결정화에 의한 소자 파괴가 방지될 수 있고, 이에 따라 상기 제1 화합물이 채용된 유기 발광 소자는 구동전압이 낮고 높은 효율을 나타낼 수 있다. The first compound has a structure in which an electron-deficient substituent, an N-containing 6-membered heterocyclic group, is bonded to an electron-rich spiro[fluorene-9,9'-xanthene) core, resulting in a low dipole moment. moment) value and amorphous characteristics. Therefore, when this first compound is employed in an organic light-emitting device, destruction of the device due to crystallization that may be caused by heat generated during operation of the device can be prevented, and accordingly, the organic light-emitting device employing the first compound can be operated at a driving voltage. This can show low and high efficiency.
상기 제1 화합물은 N 함유-6원 헤테로고리기의 치환 위치에 따라, 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시된다:The first compound is represented by any one of the following formulas 1-1 to 1-4, depending on the substitution position of the N-containing 6-membered heterocyclic group:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
상기 화학식 1-1 내지 1-4에서,In Formulas 1-1 to 1-4,
L1, X1 내지 X3, Ar1 및 Ar2는 상기 화학식 1에서 정의한 바와 같다.L 1 , X 1 to X 3 , Ar 1 and Ar 2 are as defined in Formula 1 above.
바람직하게는, 상기 제1 화합물은 상기 화학식 1-1 내지 1-3 중 어느 하나로 표시된다.Preferably, the first compound is represented by any one of Formulas 1-1 to 1-3.
바람직하게는, X1 내지 X3는 모두 N이거나;Preferably, X 1 to X 3 are all N;
X1 및 X2는 N이고, X3는 CH이거나;X 1 and X 2 are N and X 3 is CH;
X1 및 X3는 N이고, X2는 CH이거나;X 1 and X 3 are N and X 2 is CH;
X1는 N이고, X2 및 X3는 CH이거나; 또는 X 1 is N and X 2 and X 3 are CH; or
X3는 N이고, X1 및 X2는 CH이다.X 3 is N, and X 1 and X 2 are CH.
바람직하게는, L1은 단일결합, 또는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, L 1 is a single bond or any one selected from the group consisting of:
상기에서,In the above,
X는 O, S, N(C6-20 아릴), C(C1-4 알킬)2, 또는 C(C6-20 아릴)2이다.X is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
예를 들어, X는 O, S, N(페닐), C(메틸)2, 또는 C(페닐)2이다.For example, X is O, S, N(phenyl), C(methyl) 2 , or C(phenyl) 2 .
보다 바람직하게는, L1은 단일결합, 페닐렌, 또는 비페닐디일이다. More preferably, L 1 is a single bond, phenylene, or biphenyldiyl.
가장 바람직하게는, L1은 단일결합, 또는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Most preferably, L 1 is a single bond or any one selected from the group consisting of:
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 트리페닐레닐, 플루오레닐, 스피로비플루오레닐, 카바졸일, 디벤조퓨라닐, 또는 디벤조티오페닐이고,Preferably, Ar 1 and Ar 2 are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzo. furanyl, or dibenzothiophenyl,
여기서, Ar1 및 Ar2는 비치환되거나, 또는 중수소, 시아노, 할로겐, Si(C1-4 알킬)3, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 각각 독립적으로 선택되는 1개 내지 5개의 치환기로 치환될 수 있다.Here, Ar 1 and Ar 2 are unsubstituted or each independently selected from the group consisting of deuterium, cyano, halogen, Si(C 1-4 alkyl) 3, C 1-10 alkyl, and C 6-20 aryl. It may be substituted with 1 to 5 substituents.
보다 바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나이다: More preferably, Ar 1 and Ar 2 are each independently selected from the group consisting of:
상기에서,In the above,
Z는 수소, 시아노, 할로겐, Si(C1-4 알킬)3, C1-10 알킬, 또는 C6-20 아릴이고,Z is hydrogen, cyano, halogen, Si(C 1-4 alkyl) 3 , C 1-10 alkyl, or C 6-20 aryl,
X'는 O, S, N(C6-20 아릴), C(C1-4 알킬)2, 또는 C(C6-20 아릴)2이다. X' is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
예를 들어, Z는 수소, 시아노, 플루오로, Si(CH3)3, 메틸, 페닐, 나프틸, 또는 페난쓰레닐이고, X'는 O, S, N(페닐), N(나프틸), C(메틸)2, 또는 C(페닐)2이다. For example, Z is hydrogen, cyano, fluoro, Si(CH 3 ) 3, methyl, phenyl, naphthyl, or phenanthrenyl, and X' is O, S, N(phenyl), N(naphthyl) ), C (methyl) 2 , or C (phenyl) 2 .
상기 제1 화합물의 대표적인 예는 하기와 같다:Representative examples of the first compounds are as follows:
..
이때, 상기 제1 화합물은 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. At this time, the first compound can be prepared, for example, using a production method as shown in Scheme 1 below. The manufacturing method may be further detailed in the manufacturing examples described later.
[반응식 1][Scheme 1]
상기 반응식 1에서, T는 각각 독립적으로 할로겐이고, 바람직하게는 브로모, 또는 클로로이고, 다른 치환기에 대한 정의는 앞서 설명한 바와 같다. In Scheme 1, T is each independently halogen, preferably bromo or chloro, and the definitions of other substituents are as described above.
구체적으로, 상기 단계 1-1 및 1-2는 강염기 존재 하에서 출발물질을 환원시킨 후, 고리형성 반응을 통해 스피로[플루오렌-9,9'-잔텐) 코어를 제조하는 단계이고, 상기 단계 1-3은 제조된 코어에 스즈키 커플링 반응을 진행하기 위한 반응기를 도입하는 단계이며, 상기 단계 1-4는 스즈키 커플링 반응을 통해서 상기 코어에 N 함유-6원 헤테로고리기를 도입하여 화학식 1로 표시되는 화합물을 제조하는 단계이다. 이러한 스즈키 커플링 반응은 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.Specifically, steps 1-1 and 1-2 are steps for producing a spiro[fluorene-9,9'-xanthene) core through a ring formation reaction after reducing the starting material in the presence of a strong base, and step 1 -3 is a step of introducing a reactor for conducting a Suzuki coupling reaction in the prepared core, and steps 1-4 are a step of introducing an N-containing 6-membered heterocyclic group into the core through the Suzuki coupling reaction, as shown in Formula 1 This is the step of preparing the displayed compound. This Suzuki coupling reaction is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.
한편, 상기 전자수송영역은 발광층으로부터 차례로 적층되어 있는 정공차단층 및 전자수송층; 정공차단층 및 전자주입 및 수송층; 또는 정공차단층, 전자수송층 및 전자주입층으로 구성될 수 있다. 바람직하게는, 상기 정공차단층은 상기 발광층에 접하여 위치하고, 상기 제1 화합물은 상기 정공차단층 또는 상기 전자수송층에 포함된다. 보다 바람직하게는, 상기 제1 화합물은 상기 전자수송층에 포함된다. Meanwhile, the electron transport region includes a hole blocking layer and an electron transport layer sequentially stacked from the light emitting layer; Hole blocking layer and electron injection and transport layer; Alternatively, it may be composed of a hole blocking layer, an electron transport layer, and an electron injection layer. Preferably, the hole blocking layer is located in contact with the light emitting layer, and the first compound is included in the hole blocking layer or the electron transport layer. More preferably, the first compound is included in the electron transport layer.
이하, 각 유기층에 대하여 상세히 설명한다. Hereinafter, each organic layer will be described in detail.
(정공차단층)(hole blocking layer)
상기 정공차단층은 상기 발광층 상에 형성되어, 구체적으로 상기 정공차단층은 발광층에 접하여 구비되어, 정공의 과다한 이동을 방지하여 정공-전자간 결합 확률을 높여줌으로써 유기 발광 소자의 효율을 개선하는 역할을 한다. 상기 정공차단층은 정공 차단 물질을 포함하고, 이러한 정공 차단 물질로는 발광층에서 정공이 흘러나오지 않을 수 있는 안정된 구조를 갖는 물질이 적합하다. The hole blocking layer is formed on the light emitting layer. Specifically, the hole blocking layer is provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by preventing excessive movement of holes and increasing the probability of hole-electron coupling. Do it. The hole blocking layer includes a hole blocking material, and a material having a stable structure that prevents holes from flowing out of the light emitting layer is suitable as the hole blocking material.
바람직하게는, 상기 정공 차단 물질로 상기 화학식 1로 표시되는 제1 화합물을 사용한다. 또는, 상기 정공 차단 물질로 트리아진을 포함한 아진류 유도체; 트리아졸 유도체; 옥사디아졸 유도체; 페난트롤린 유도체; 포스핀옥사이드 유도체 등의 전자흡인기가 도입된 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다.Preferably, the first compound represented by Formula 1 is used as the hole blocking material. Alternatively, the hole blocking material may be an azine derivative including triazine; triazole derivatives; Oxadiazole derivatives; phenanthroline derivatives; Compounds into which electron-withdrawing groups are introduced, such as phosphine oxide derivatives, may be used, but are not limited thereto.
(전자수송층)(electron transport layer)
상기 전자수송층은 상기 발광층과 음극 사이, 바람직하게는 상기 정공차단층과 후술하는 전자주입층 사이에 형성되어 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 역할을 한다. 상기 전자수송층은 전자 수송 물질을 포함하고, 이러한 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. The electron transport layer is formed between the light emitting layer and the cathode, preferably between the hole blocking layer and the electron injection layer described later, and serves to receive electrons from the electron injection layer and transport electrons to the light emitting layer. The electron transport layer contains an electron transport material, and the electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light emitting layer, and a material with high mobility for electrons is suitable.
바람직하게는, 상기 전자 수송 물질로 상기 화학식 1로 표시되는 제1 화합물을 사용한다. 또는, 상기 전자 수송 물질로 피리딘 유도체; 피리미딘 유도체; 트리아졸 유도체; 트리아진 유도체; 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등을 사용할 수 있으나, 이에 한정되는 것은 아니다. Preferably, the first compound represented by Formula 1 is used as the electron transport material. Alternatively, the electron transport material may be a pyridine derivative; pyrimidine derivatives; triazole derivatives; triazine derivatives; Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes may be used, but are not limited thereto.
또한, 상기 전자수송층은 상기 전자 수송 물질과 함께 금속 착체 화합물을 포함할 수 있다. 상기 금속 착체 화합물로는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에, 한정되는 것은 아니다.Additionally, the electron transport layer may include a metal complex compound along with the electron transport material. The metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
(전자주입층)(electron injection layer)
상기 전자주입층은 상기 전자수송층과 음극 사이에 위치하여, 음극으로부터 전자를 주입하는 역할을 한다. 상기 전자주입층은 전자 주입 물질을 포함하고, 이러한 전자 주입 물질로는 전자를 수송하는 능력을 가지면서, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 박막형성능력이 우수한 물질이 적합하다.The electron injection layer is located between the electron transport layer and the cathode and serves to inject electrons from the cathode. The electron injection layer includes an electron injection material, and a material that has the ability to transport electrons, has an excellent electron injection effect with respect to the light-emitting layer or light-emitting material, and has excellent thin film forming ability is suitable as the electron injection material.
상기 전자 주입 물질의 구체적인 예로는, LiF, NaCl, CsF, Li2O, BaO, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에, 한정되는 것은 아니다. Specific examples of the electron injection material include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, Examples include, but are not limited to, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.
유기 발광 소자organic light emitting device
본 발명에 따른 유기 발광 소자의 구조를 도 1 및 도 2에 예시하였다.The structure of the organic light emitting device according to the present invention is illustrated in Figures 1 and 2.
도 1은 기판(10), 양극(20), 정공수송영역(30), 발광층(40), 전자수송영역(50) 및 음극(60)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 제1 화합물은 상기 전자수송영역(50)에, 상기 제2 화합물은 상기 발광층(40)에 각각 포함될 수 있다.Figure 1 shows an example of an organic light emitting device consisting of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60. In this structure, the first compound may be included in the electron transport region 50, and the second compound may be included in the light-emitting layer 40.
도 2는 기판(10), 양극(20), 정공수송영역(30), 발광층(40), 전자수송영역(50) 및 음극(60)으로 이루어지고, 상기 정공수송영역(30)은 양극(20)으로부터 차례로 적층된 정공주입층(31), 정공수송층(33) 및 전자차단층(35)을 구비하고, 상기 전자수송영역(50)은 발광층(40)으로부터 차례로 적층된 정공차단층(51), 전자수송층(53) 및 전자주입층(55)을 구비한 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 제1 화합물은 상기 정공차단층(51) 또는 전자수송층(53)에, 상기 제2 화합물은 상기 발광층(40)에 각각 포함될 수 있다.Figure 2 consists of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50, and a cathode 60, and the hole transport region 30 is an anode ( A hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20), and the electron transport region 50 is a hole blocking layer 51 stacked sequentially from the light emitting layer 40. ), shows an example of an organic light-emitting device having an electron transport layer 53 and an electron injection layer 55. In this structure, the first compound may be included in the hole blocking layer 51 or the electron transport layer 53, and the second compound may be included in the light-emitting layer 40.
본 발명에 따른 유기 발광 소자는 상술한 구성을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 상술한 각 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 발광층은 호스트 및 도펀트를 진공 증착법 뿐만 아니라 용액 도포법에 의하여 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described structures. At this time, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming each of the above-described layers thereon and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. Additionally, the light-emitting layer can be formed by using a solution coating method as well as a vacuum deposition method for the host and dopant. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, 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 to this.
한편, 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.Meanwhile, the organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
상기 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.Manufacturing of the organic light emitting device will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
제조예 1: 화합물 1-1의 제조Preparation Example 1: Preparation of Compound 1-1
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A(12.13g, 26.49mmol), (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산(8.50g, 24.08mmol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액(100ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.83g, 0.72mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 280ml로 재결정하여 화합물 1-1 (11.16g, 72%)를 제조하였다.Compound A (12.13 g, 26.49 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (8.50 g, 24.08mmol) was completely dissolved in 200ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (100ml) was added, tetrakis-(triphenylphosphine)palladium (0.83g, 0.72mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of ethyl acetate to prepare Compound 1-1 (11.16 g, 72%).
MS[M+H]+= 640MS[M+H] + = 640
제조예 2: 화합물 1-2의 제조Preparation Example 2: Preparation of Compound 1-2
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 B(10.70g, 23.37mmol), 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진(7.5g, 21.25mmol)을 테트라하이드로퓨란 220ml에 완전히 녹인 후 2M 탄산칼륨수용액(110ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.74g, 0.64mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 240ml로 재결정하여 화합물 1-2 (8.46g, 62%)를 제조하였다.Compound B (10.70 g, 23.37 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5- in a 500 ml round bottom flask under nitrogen atmosphere. Triazine (7.5 g, 21.25 mmol) was completely dissolved in 220 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (110 ml) was added, tetrakis-(triphenylphosphine) palladium (0.74 g, 0.64 mmol) was added, and then 4 It was heated and stirred for an hour. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to prepare Compound 1-2 (8.46 g, 62%).
MS[M+H]+= 640MS[M+H] + = 640
제조예 3: 화합물 1-3의 제조Preparation Example 3: Preparation of Compound 1-3
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 C(7.49g, 16.36mmol), 2-(4-브로모페닐)-4-(나프탈렌-1-일)-6-페닐-1,3,5-트리아진(6.50g, 14.87mmol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액(100ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.52g, 0.45mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 180ml로 재결정하여 화합물 1-3 (5.89g, 62%)를 제조하였다.Compound C (7.49 g, 16.36 mmol), 2-(4-bromophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine in a 500 ml round bottom flask under nitrogen atmosphere. (6.50g, 14.87mmol) was completely dissolved in 200ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (100ml) was added, and tetrakis-(triphenylphosphine)palladium (0.52g, 0.45mmol) was added and incubated for 3 hours. It was heated and stirred. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to prepare Compound 1-3 (5.89 g, 62%).
MS[M+H]+= 690MS[M+H] + = 690
제조예 4: 화합물 2-1의 제조Preparation Example 4: Preparation of Compound 2-1
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 2-브로모-10-(나프탈렌-1-일)-9-페닐안트라센(15.50g, 33.84mmol), 나프탈렌-2-일보론산(6.40g, 37.23mmol)을 테트라하이드로퓨란 260ml에 완전히 녹인 후 2M 탄산칼륨수용액(130ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(1.17g, 1.02mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250ml로 재결정하여 화합물 2-1 (8.64g, 50%)를 제조하였다.Compounds 2-bromo-10-(naphthalen-1-yl)-9-phenylanthracene (15.50 g, 33.84 mmol) and naphthalen-2-ylboronic acid (6.40 g, 37.23 mmol) were added to a 500 ml round bottom flask in a nitrogen atmosphere. After completely dissolving in 260ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (130ml) was added, tetrakis-(triphenylphosphine)palladium (1.17g, 1.02mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare Compound 2-1 (8.64 g, 50%).
MS[M+H]+= 507MS[M+H] + = 507
제조예 5: 화합물 2-2의 제조Preparation Example 5: Preparation of Compound 2-2
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 2-브로모-10-(페난쓰렌-9-일)-9-페닐안트라센(9.50g, 18.70mmol), 디벤조[b,d]퓨란-2-일보론산(4.36g, 20.57mmol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액(120ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.65g, 0.56mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 240ml로 재결정하여 화합물 2-2 (6.44g, 58%)를 제조하였다.Compound 2-bromo-10-(phenanthren-9-yl)-9-phenylanthracene (9.50 g, 18.70 mmol) and dibenzo[b,d]furan-2-ylboronic acid in a 500 ml round bottom flask under nitrogen atmosphere. (4.36g, 20.57mmol) was completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.65g, 0.56mmol) was added, and then allowed to brew for 4 hours. It was heated and stirred. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to prepare Compound 2-2 (6.44 g, 58%).
MS[M+H]+= 597MS[M+H] + = 597
제조예 6: 화합물 2-3의 제조Preparation Example 6: Preparation of Compound 2-3
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 3-(3-브로모-10-페닐안트라센-9-일)디벤조[b,d]티오펜(7.50g, 14.59mmol), [1,1'-비페닐]-3-일보론산(3.18g, 16.05mmol)을 테트라하이드로퓨란 180ml에 완전히 녹인 후 2M 탄산칼륨수용액(90ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.51g, 0.44mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 270ml로 재결정하여 화합물 2-3 (5.11g, 89%)를 제조하였다.Compound 3-(3-bromo-10-phenylanthracen-9-yl)dibenzo[b,d]thiophene (7.50 g, 14.59 mmol), [1,1'-bi] was added to a 500 ml round bottom flask in a nitrogen atmosphere. Phenyl]-3-ylboronic acid (3.18g, 16.05mmol) was completely dissolved in 180ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (90ml) was added, and tetrakis-(triphenylphosphine)palladium (0.51g, 0.44mmol) was added. ) was added and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 ml of ethyl acetate to prepare Compound 2-3 (5.11 g, 89%).
MS[M+H]+= 589MS[M+H] + = 589
실시예 1Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 HI-1 및 하기 화합물 HI-2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다.On the ITO transparent electrode prepared in this way, the following compound HI-1 and the following compound HI-2 were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer.
상기 정공 주입층 위에 정공을 수송하는 물질인 하기 화합물 HT-1 (1150Å)를 진공 증착하여 정공 수송층을 형성하였다.A hole transport layer was formed by vacuum depositing the following compound HT-1 (1150Å), a hole transport material, on the hole injection layer.
이어서, 상기 정공수송층 위에 막 두께 50Å으로 하기 화합물 EB-1를 진공 증착하여 전자차단층을 형성하였다.Next, the following compound EB-1 was vacuum deposited on the hole transport layer to a film thickness of 50 Å to form an electron blocking layer.
이어서, 상기 전자차단층 위에 막 두께 200Å으로 상기 제조예 4에서 제조한 화합물 2-1(호스트)과 하기 화합물 BD-1(도펀트)를 40:1의 중량비로 진공증착하여 발광층을 형성하였다.Next, Compound 2-1 (host) prepared in Preparation Example 4 and Compound BD-1 (dopant) below were vacuum deposited at a weight ratio of 40:1 with a film thickness of 200 Å on the electron blocking layer to form a light-emitting layer.
상기 발광층 위에 막 두께 50Å으로 하기 화합물 HB-1를 진공 증착하여 정공차단층을 형성하였다.A hole blocking layer was formed by vacuum depositing the following compound HB-1 to a film thickness of 50 Å on the light emitting layer.
이어서, 상기 정공차단층 위에 하기 제조예 1에서 제조한 화합물 1-1과 하기 화합물 LiQ(Lithium Quinolate)를 1:1의 중량비로 진공증착하여 300Å의 두께로 전자수송층을 형성하였다. Next, compound 1-1 prepared in Preparation Example 1 below and the following compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å.
상기 전자수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 증착하여 각각 전자주입층 및 음극을 형성하였다.Lithium fluoride (LiF) to a thickness of 12Å and aluminum to a thickness of 2,000Å were sequentially deposited on the electron transport layer to form an electron injection layer and a cathode, respectively.
상기의 과정에서 유기물의 증착속도는 0.4~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2 ⅹ10-7 ~5 ⅹ10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2ⅹ10-7. An organic light emitting device was manufactured by maintaining ~5 x 10-6 torr.
상기 실시예 1에 사용된 화합물은 하기와 같다.The compounds used in Example 1 are as follows.
실시예 2 내지 실시예 9 및 비교예 1 내지 10Examples 2 to 9 and Comparative Examples 1 to 10
상기 실시예 1에서 호스트 화합물 2-1 및 전자수송층의 화합물 1-1 대신 하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 상기 실시예 및 비교예에서 사용된 화합물은 하기와 같다.An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of the host compound 2-1 and the electron transport layer compound 1-1. The compounds used in the above examples and comparative examples are as follows.
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 20 mA/cm2의 전류를 인가하였을 때, 상기 제조한 유기 발광 소자를 20 mA/cm2의 전류밀도에서 구동 전압, 발광 효율, 색 좌표를 측정하였고, 20 mA/cm2의 전류밀도에서 초기 휘도 대비 95%가 되는 시간(T95)을 측정하였다. 그 결과를 하기 표 1에 나타내었다. 이때, T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current of 20 mA/cm 2 was applied to the organic light-emitting device manufactured in the Examples and Comparative Examples, the driving voltage, luminous efficiency, and color coordinates of the organic light-emitting device were changed at a current density of 20 mA/cm 2 The time for reaching 95% of the initial luminance (T95) was measured at a current density of 20 mA/cm 2 . The results are shown in Table 1 below. At this time, T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
(전자수송층)compound
(electron transport layer)
(발광층
호스트)compound
(luminous layer
host)
(V
@20mA
/cm2)Voltage
(V
@20mA
/cm 2 )
(cd/A
@20mA
/cm2 efficiency
(cd/A
@20mA
/cm 2
(x,y)Color coordinates
(x,y)
(hr)T95
(hr)
상기 표 1에 나타난 바와 같이, 상기 화학식 1로 표시되는 화합물을 전자수송층 물질로 사용하고 상기 화학식 2로 표시되는 화합물을 발광층의 호스트 물질로 동시에 사용한 실시예의 유기 발광 소자는, 상기 화학식 1 및 2로 표시되는 화합물 중 하나만을 채용하거나, 둘 다 채용하지 않는 비교예의 유기 발광 소자에 비하여, 구동 전압, 발광 효율 및 수명 측면 모두에서 우수한 특성을 나타내었다. As shown in Table 1, the organic light-emitting device of the example in which the compound represented by Formula 1 was used as the electron transport layer material and the compound represented by Formula 2 was simultaneously used as the host material of the light-emitting layer had the formulas 1 and 2. Compared to the organic light-emitting device of the comparative example in which only one or both of the displayed compounds was used, it showed excellent characteristics in terms of driving voltage, luminous efficiency, and lifespan.
구체적으로, 비교예 1 내지 3 및 비교예 8 내지 10을 살펴보면, 상기 화학식 1로 표시되는 화합물은 9,9-디페닐-9H-플루오렌에 트리아지닐기가 연결된 ET-1 및 트리페닐렌에 트리아지닐기가 연결된 비교예 화합물 ET-2에 비하여, 전자주입 특성 및 발광층으로 전자를 이동시키는 특성이 우수하여 소자의 효율 향상에 기여함을 알 수 있다. 그리고, 비교예 4 내지 7, 비교예 9 및 비교예 10을 살펴보면, 상기 화학식 2로 표시되는 화합물은 안트라센 2번 위치에 치환기를 갖지 않는 비교예 화합물 BH-1 및 BH-2에 비하여, 물질 안정성이 우수하여 소자의 장수명 특성에 기여함을 알 수 있다. Specifically, looking at Comparative Examples 1 to 3 and Comparative Examples 8 to 10, the compound represented by Formula 1 is ET-1 in which a triazinyl group is connected to 9,9-diphenyl-9H-fluorene and triazinyl group is connected to triphenylene. It can be seen that compared to the comparative example compound ET-2 to which a zyl group is connected, the electron injection characteristics and electron transfer characteristics to the light-emitting layer are excellent, contributing to improving the efficiency of the device. And, looking at Comparative Examples 4 to 7, Comparative Example 9, and Comparative Example 10, the compound represented by Formula 2 has material stability compared to Comparative Example compounds BH-1 and BH-2, which do not have a substituent at the anthracene 2 position. It can be seen that this is excellent and contributes to the long life characteristics of the device.
또한, ET-2 및 BH-2와 ET-1 및 BH-1를 서로 조합하더라도 효율 및 수명 특성이 동시에 향상되지는 않는 비교예 9 및 10의 유기 발광 소자와는 달리, 상기 화학식 1로 표시되는 화합물과 상기 화학식 2로 표시되는 화합물을 모두 채용한 본 발명에 따른 실시예의 유기 발광 소자는 효율 및 수명 특성이 동시에 향상됨이 확인된다. 이는 일반적으로 유기 발광 소자의 발광 효율 및 수명 특성은 서로 트레이드-오프(Trade-off) 관계를 갖는 점을 고려할 때 본 발명의 화합물간의 조합을 채용한 유기 발광 소자는 비교예 소자 대비 현저히 향상된 소자 특성을 가짐을 알 수 있다.In addition, unlike the organic light emitting devices of Comparative Examples 9 and 10 in which efficiency and lifespan characteristics are not simultaneously improved even when ET-2 and BH-2 and ET-1 and BH-1 are combined, the organic light emitting devices represented by Formula 1 above do not improve simultaneously. It was confirmed that the efficiency and lifespan characteristics of the organic light-emitting device of an example according to the present invention employing both the compound and the compound represented by Formula 2 were improved at the same time. Considering that the luminous efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, the organic light-emitting devices using the combination of compounds of the present invention have significantly improved device characteristics compared to the comparative devices. It can be seen that it has .
10: 기판 20: 양극
30: 정공수송영역 31: 정공주입층
33: 정공수송층 35: 전자차단층
40: 발광층 50: 전자수송영역
51: 정공차단층 53: 전자수송층
55: 전자주입층 60: 음극10: substrate 20: anode
30: Hole transport area 31: Hole injection layer
33: hole transport layer 35: electron blocking layer
40: light emitting layer 50: electron transport area
51: hole blocking layer 53: electron transport layer
55: electron injection layer 60: cathode
Claims (12)
상기 양극에 대향하여 구비된 음극;
상기 양극과 음극 사이에 구비된 발광층;
상기 양극과 발광층 사이에 구비된 정공수송영역; 및
상기 발광층과 음극 사이에 구비된 전자수송영역을 포함하고,
상기 전자수송영역은 하기 화학식 1로 표시되는 제1 화합물을 포함하고,
상기 발광층은 하기 화학식 2로 표시되는 제2 화합물을 포함하는,
유기 발광 소자:
[화학식 1]
상기 화학식 1에서,
X1 내지 X3는 각각 독립적으로, N 또는 CH이되, X1 내지 X3 중 적어도 하나는 N이고,
L1은 단일결합, 페닐렌, 또는 비페닐디일이고,
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 또는 트리페닐레닐이고,
여기서, Ar1 및 Ar2는 비치환되거나, 또는 중수소, 시아노, 할로겐, Si(C1-4 알킬)3, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 각각 독립적으로 선택되는 1개 내지 5개의 치환기로 치환되고,
[화학식 2]
상기 화학식 2에서,
L2는 단일 결합이고,
L3는 단일 결합이고,
Ar3는 페닐이고,
Ar4는 비페닐릴, 터페닐릴, 페난쓰레닐, 디벤조퓨라닐, 또는 디벤조티오페닐이고,
R은 하기로 구성되는 군으로부터 선택되는 어느 하나이고,
상기에서,
Q는 수소, tert-부틸, Si(메틸)3, 페닐, 또는 나프틸이고,
Y2는 O, S, N(페닐), C(메틸)2, 또는 C(페닐)2이다.
anode;
a cathode provided opposite the anode;
A light emitting layer provided between the anode and the cathode;
A hole transport area provided between the anode and the light emitting layer; and
It includes an electron transport region provided between the light emitting layer and the cathode,
The electron transport region includes a first compound represented by the following formula (1),
The light-emitting layer includes a second compound represented by the following formula (2),
Organic light emitting device:
[Formula 1]
In Formula 1,
X 1 to X 3 are each independently N or CH, but at least one of X 1 to X 3 is N,
L 1 is a single bond, phenylene, or biphenyldiyl,
Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, or triphenylenyl,
Here, Ar 1 and Ar 2 are unsubstituted or each independently selected from the group consisting of deuterium, cyano, halogen, Si(C 1-4 alkyl) 3, C 1-10 alkyl, and C 6-20 aryl. is substituted with 1 to 5 substituents,
[Formula 2]
In Formula 2,
L 2 is a single bond,
L 3 is a single bond,
Ar 3 is phenyl,
Ar 4 is biphenylyl, terphenylyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl,
R is any one selected from the group consisting of:
In the above,
Q is hydrogen, tert-butyl, Si(methyl) 3 , phenyl, or naphthyl,
Y 2 is O, S, N(phenyl), C(methyl) 2 , or C(phenyl) 2 .
상기 제1 화합물은 하기 화학식 1-1 내지 1-3 중 어느 하나로 표시되는,
유기 발광 소자:
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
상기 화학식 1-1 내지 1-3에서,
L1, X1 내지 X3, Ar1 및 Ar2는 제1항에서 정의한 바와 같다.
According to paragraph 1,
The first compound is represented by any one of the following formulas 1-1 to 1-3,
Organic light emitting device:
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
In Formulas 1-1 to 1-3,
L 1 , X 1 to X 3 , Ar 1 and Ar 2 are as defined in clause 1.
X1 내지 X3는 모두 N이거나;
X1 및 X2는 N이고, X3는 CH이거나;
X1 및 X3는 N이고, X2는 CH이거나;
X1는 N이고, X2 및 X3는 CH이거나; 또는
X3는 N이고, X1 및 X2는 CH인,
유기 발광 소자.
According to paragraph 1,
X 1 to X 3 are all N;
X 1 and X 2 are N and X 3 is CH;
X 1 and X 3 are N and X 2 is CH;
X 1 is N and X 2 and X 3 are CH; or
X 3 is N, X 1 and X 2 are CH,
Organic light emitting device.
L1은 단일결합, 또는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to paragraph 1,
L 1 is a single bond or any one selected from the group consisting of:
Organic light emitting device:
Ar1 및 Ar2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
상기에서,
Z는 수소, 시아노, 플루오로, 메틸, 페닐, 나프틸, 또는 페난쓰레닐이다.
According to paragraph 1,
Ar 1 and Ar 2 are each independently selected from the group consisting of:
Organic light emitting device:
In the above,
Z is hydrogen, cyano, fluoro, methyl, phenyl, naphthyl, or phenanthrenyl.
상기 제1 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
.
According to paragraph 1,
The first compound is any one selected from the group consisting of:
Organic light emitting device:
.
상기 제2 화합물은 하기 화학식 2-1로 표시되는,
유기 발광 소자:
[화학식 2-1]
상기 화학식 2-1에서,
Ar4는 페난쓰레닐, 또는 디벤조티오페닐이고,
L3 및 R은 제1항에서 정의한 바와 같다.
According to paragraph 1,
The second compound is represented by the following formula 2-1,
Organic light emitting device:
[Formula 2-1]
In Formula 2-1,
Ar 4 is phenanthrenyl, or dibenzothiophenyl,
L 3 and R are as defined in paragraph 1.
상기 제2 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
.
According to paragraph 1,
The second compound is any one selected from the group consisting of:
Organic light emitting device:
.
상기 전자수송영역은 정공차단층, 전자수송층 및 전자주입층을 포함하고
상기 정공차단층은 상기 발광층에 접하여 위치하고,
상기 제1 화합물은 상기 정공차단층 또는 상기 전자수송층에 포함되는,
유기 발광 소자.According to paragraph 1,
The electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer.
The hole blocking layer is located in contact with the light emitting layer,
The first compound is included in the hole blocking layer or the electron transport layer,
Organic light emitting device.
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