KR102583027B1 - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR102583027B1 KR102583027B1 KR1020190028864A KR20190028864A KR102583027B1 KR 102583027 B1 KR102583027 B1 KR 102583027B1 KR 1020190028864 A KR1020190028864 A KR 1020190028864A KR 20190028864 A KR20190028864 A KR 20190028864A KR 102583027 B1 KR102583027 B1 KR 102583027B1
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- organic light
- emitting device
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 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
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- 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
- 238000003618 dip coating Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 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
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- 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
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 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
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- 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
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- 239000011133 lead Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
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- 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
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- 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
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- 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
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- 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
- 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
- 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 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
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 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
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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Abstract
본 발명은 신규한 화합물 및 이를 이용한 유기발광 소자를 제공한다. The present invention provides a novel compound and an organic light-emitting device using the same.
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to novel compounds and organic light-emitting devices containing them.
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 유기물층을 포함하는 구조를 가진다. 상기 유기물층은 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 material 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 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to novel compounds and organic light-emitting devices containing them.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by the following formula (1):
[화학식 1] [Formula 1]
상기 화학식 1에서,In Formula 1,
L1 및 L2는 각각 독립적으로, 단일결합; 또는 치환 또는 비치환된 C6-60 아릴렌이고,L 1 and L 2 are each independently a single bond; Or substituted or unsubstituted C 6-60 arylene,
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 안트라세닐, 트리페닐레닐, 파이레닐, 크라이세닐, 나프타세닐, 카바졸일, 디벤조퓨라닐, 디벤조티오페닐, 벤조나프토퓨라닐, 또는 벤조나프토티오페닐이고,Ar 1 and Ar 2 are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, carbazolyl, and dibenzofuranyl. , dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,
여기서, 상기 Ar1 및 Ar2는 비치환되거나, 또는 C1-20 알킬 및 C6-20 아릴로 구성되는 군으로부터 각각 독립적으로 선택되는 1개 이상의 치환기로 치환되고,Here, Ar 1 and Ar 2 are unsubstituted or substituted with one or more substituents each independently selected from the group consisting of C 1-20 alkyl and C 6-20 aryl,
Ar3는 치환 또는 비치환된 비페닐릴이다.Ar 3 is substituted or unsubstituted biphenylyl.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. .
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다.The compound represented by the above-described formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device.
도 1은 기판(1), 양극(2), 정공수송층(3), 발광층(4), 전자주입 및 수송층(5) 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판(1), 양극(2), 정공주입층(7), 정공수송층(3), 전자억제층(8), 발광층(4), 정공저지층(9), 전자주입 및 수송층(5) 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Figure 2 shows a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light emitting layer (4), a hole blocking layer (9), an electron injection and transport layer ( 5) and a cathode 6. An example of an organic light-emitting device is shown.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid understanding.
(용어의 정의)(Definition of Terms)
본 명세서에서, 및 는 다른 치환기에 연결되는 결합을 의미한다.In this specification, and means a bond connected to another substituent.
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 헤테로아릴로 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, 비페닐이기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 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 heteroaryl 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 한정되지 않는다. 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 한정되지 않는다.In the present 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, 사이클로헥틸메틸, 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 한정되지 않는다.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, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 방향족성(aromaticity)을 갖는 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, 비페닐이기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난쓰레닐기, 트리페닐레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기 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 with aromaticity. 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, triphenylenyl group, pyrenyl group, perylenyl group, chrysenyl group, etc., but is not limited thereto.
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, 벤조옥사졸기, 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, benzooxazole 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, 아릴실릴기 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, arylamine group, and arylsilyl 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.
(화합물)(compound)
한편, 본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. Meanwhile, the present invention provides a compound represented by Formula 1 above.
구체적으로, 상기 화학식 1로 표시되는 화합물은 Ar3 치환기가 비페닐-1,4-디일 링커(ortho-비페닐릴 링커)에 의해 N 원자와 연결된 아민계 화합물이다. 이때, 상기 Ar3 치환기는 치환 또는 비치환된 비페닐기로, 바람직하게는 2개 이상의 페닐기들이 연결된 단환식 치환기 구조를 갖는다. 이에 따라 상기 화합물은 상기 링커를 갖지 않거나 혹은 2개 이상의 페닐기들이 연결된 단환식 치환기 구조를 갖지 않는 화합물에 비하여, 향상된 정공 수송 능력 및 개선된 열안정성을 나타낼 수 있다. 이로써, 상기 화합물을 채용한 유기 발광 소자는 고효율, 저 구동 전압 및 장수명 등의 특성을 나타낼 수 있다. Specifically, the compound represented by Formula 1 is an amine-based compound in which the Ar 3 substituent is linked to the N atom by a biphenyl-1,4-diyl linker (ortho-biphenylyl linker). At this time, the Ar 3 substituent is a substituted or unsubstituted biphenyl group, and preferably has a monocyclic substituent structure in which two or more phenyl groups are connected. Accordingly, the compound may exhibit improved hole transport ability and improved thermal stability compared to a compound that does not have the linker or a monocyclic substituent structure in which two or more phenyl groups are connected. As a result, organic light-emitting devices employing the above compounds can exhibit characteristics such as high efficiency, low driving voltage, and long lifespan.
상기 화학식 1에서, 바람직하게는, L1 및 L2는 각각 독립적으로, 단일결합, 페닐렌. 비페닐디일, 또는 나프틸렌이다.In Formula 1, preferably, L 1 and L 2 are each independently a single bond and phenylene. Biphenyldiyl, or naphthylene.
보다 바람직하게는, L1 및 L2는 단일결합, 또는 1,4-페닐렌이다.More preferably, L 1 and L 2 are a single bond or 1,4-phenylene.
..
바람직하게는, Ar1 및 Ar2는 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 트리페닐레닐, 카바졸일, 디벤조퓨라닐, 디벤조티오페닐, 벤조나프토퓨라닐, 또는 벤조나프토티오페닐이고, 여기서, 상기 Ar1 및 Ar2는 비치환되거나, 또는 C6-20 아릴로 치환된다. Preferably, Ar 1 and Ar 2 are phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or It is benzonaphthothiophenyl, wherein Ar 1 and Ar 2 are unsubstituted or substituted with C 6-20 aryl.
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,
R은 수소 또는 페닐이다.R is hydrogen or phenyl.
이때, Ar1 및 Ar2는 서로 동일할 수 있다. 바람직하게는, Ar1 및 Ar2가 모두 페닐인 경우는 상기 화합물의 유리전이온도(Tg)가 낮아질 수 있어 제외된다. At this time, Ar 1 and Ar 2 may be the same. Preferably, when both Ar 1 and Ar 2 are phenyl, they are excluded because the glass transition temperature (Tg) of the compound may be lowered.
다르게는, Ar1 및 Ar2는 서로 상이할 수 있다. Alternatively, Ar 1 and Ar 2 may be different from each other.
바람직하게는, Ar3는 비치환되거나, 또는 페닐, 비페닐릴, 또는 터페닐릴로 치환된 비페닐릴이다.Preferably, Ar 3 is biphenylyl, which is unsubstituted or substituted with phenyl, biphenylyl, or terphenylyl.
보다 바람직하게는, Ar3는 비페닐릴, 터페닐릴, 또는 쿼터페닐릴이다.More preferably, Ar 3 is biphenylyl, terphenylyl, or quarterphenylyl.
가장 바람직하게는, Ar3는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Most preferably, Ar 3 is any one selected from the group consisting of:
바람직하게는, 상기 화합물은 하기 화학식 1-1 내지 1-3 중 어느 하나로 표시된다:Preferably, the compound is represented by any one of the following formulas 1-1 to 1-3:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
상기 화학식 1-1 내지 1-3에서,In Formulas 1-1 to 1-3,
Ar1 및 Ar2에 대한 설명은 상기 화학식 1에서 정의한 바와 같고,The description of Ar 1 and Ar 2 is as defined in Formula 1 above,
Ph는 페닐을 의미하고,Ph means phenyl,
n은 0 또는 1이고,n is 0 or 1,
m은 0, 1, 또는 2이다.m is 0, 1, or 2.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 하기와 같다:Representative examples of compounds represented by Formula 1 are as follows:
한편, 상기 화학식 1로 표시되는 화합물은 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. Meanwhile, the compound represented by Chemical Formula 1 can be prepared, for example, by 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, 각 치환기에 대한 설명은 앞서 정의한 바와 같다. 상기 단계 1-1은 출발물질 S-1에 브로모기를 도입하여 중간체 화합물 I-1을 제조하는 단계이고, 상기 단계 1-2는 Suzuki-coupling 반응에 의해 브로모가 치환된 자리에 치환기 Ar3를 도입하여 중간체 화합물 I-2를 제조하는 단계로 팔라듐 촉매 및 염기 하에서 수행되는 것이 바람직하고, 상기 단계 1-3은 2차 아민인 중간체 화합물 I-2에 치환기를 도입하여 3차 아민 화합물인 상기 화학식 1로 표시되는 화합물을 제조하는 반응으로, 팔라듐 촉매 하에서 수행하는 것이 바람직하다. 이러한 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.In Scheme 1, the description of each substituent is as defined above. Step 1-1 is a step of preparing intermediate compound I-1 by introducing a bromo group into the starting material S-1, and step 1-2 is a step of adding a substituent Ar 3 to the position where bromo was substituted by Suzuki-coupling reaction. The step of preparing intermediate compound I-2 by introducing a substituent into intermediate compound I-2, which is a secondary amine, is preferably performed under a palladium catalyst and a base, and step 1-3 is a tertiary amine compound of the formula above The reaction for producing the compound represented by 1 is preferably carried out under a palladium catalyst. This manufacturing method can be further detailed in the manufacturing examples described later.
(유기 발광 소자)(Organic light emitting device)
한편, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. Meanwhile, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. In one example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. .
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 Contains the indicated compounds.
또한, 상기 유기물층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1.
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 발광층 이외에, 상기 제1전극과 상기 발광층 사이의 정공주입층 및 정공수송층, 및 상기 발광층과 상기 제2전극 사이의 전자수송층 및 전자주입층을 더 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention is an organic material layer that, in addition to the light-emitting layer, further includes a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode. It can have a structure that does. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic layers.
또한, 본 발명에 따른 유기 발광 소자는, 상기 제1 전극이 양극이고 상기 제2 전극은 음극인, 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는, 상기 제1 전극이 음극이고 상기 제2 전극은 양극인, 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.In addition, the organic light emitting device according to the present invention is a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate where the first electrode is an anode and the second electrode is a cathode. It may be a device. In addition, the organic light emitting device according to the present invention is an inverted type organic device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate where the first electrode is a cathode and the second electrode is an anode. It may be a light emitting device. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 정공수송층(3), 발광층(4), 전자주입 및 수송층(5) 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공수송층에 포함될 수 있다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In this structure, the compound represented by Formula 1 may be included in the hole transport layer.
도 2는 기판(1), 양극(2), 정공주입층(7), 정공수송층(3), 전자억제층(8), 발광층(4), 정공저지층(9), 전자주입 및 수송층(5) 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 또는 전자억제층에 포함될 수 있다.Figure 2 shows a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light emitting layer (4), a hole blocking layer (9), an electron injection and transport layer ( 5) and a cathode 6. An example of an organic light-emitting device is shown. In this structure, the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.
본 발명에 따른 유기 발광 소자는, 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Chemical Formula 1. Additionally, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 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 정공 주입층, 정공 수송층, 발광층 및 전자수송층을 포함하는 유기물층을 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. For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. 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 an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer 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.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 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.Additionally, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. 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.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 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 multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 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. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 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, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable 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 material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. These include organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 상기 정공 수송 물질로 상기 화학식 1로 표시되는 화합물을 사용하거나, 또는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등을 사용할 수 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and has high mobility for holes. The material is suitable. As the hole transport material, a compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having both a conjugated and non-conjugated portion may be used, but is not limited thereto. .
상기 전자억제층은 상기 정공수송층 상에 형성되어, 바람직하게는 발광층에 접하여 구비되어, 정공이동도를 조절하고, 전자의 과다한 이동을 방지하여 정공-전자간 결합 확률을 높여줌으로써 유기 발광 소자의 효율을 개선하는 역할을 하는 층을 의미한다. 상기 전자억제층은 전자저지물질을 포함하고, 이러한 전자저지물질의 예로 상기 화학식 1로 표시되는 화합물을 사용하거나, 또는 아릴아민 계열의 유기물 등을 사용할 수 있으나, 이에 한정되는 것은 아니다.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 hole-electron coupling, thereby increasing the efficiency of the organic light emitting device. This refers to the layer that plays a role in improving. The electron blocking layer includes an electron blocking material, and examples of the electron blocking material include the compound represented by Chemical Formula 1, or an arylamine-based organic material, but are not limited thereto.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이에 한정되는 것은 아니다. The light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
상기 발광층은 상술한 바와 같이 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 더 포함할 수 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다. The light emitting layer may include a host material and a dopant material as described above. The host material may further include a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
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.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.
상기 정공저지층은 발광층 상에 형성되어, 바람직하게는 발광층에 접하여 구비되어, 전자이동도를 조절하고 정공의 과다한 이동을 방지하여 정공-전자간 결합 확률을 높여줌으로써 유기 발광 소자의 효율을 개선하는 역할을 하는 층을 의미한다. 상기 정공저지층은 정공저지물질을 포함하고, 이러한 정공저지물질의 예로 트리아진을 포함한 아진류유도체; 트리아졸 유도체; 옥사디아졸 유도체; 페난트롤린 유도체; 포스핀옥사이드 유도체 등의 전자흡인기가 도입된 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다.The hole blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, to improve the efficiency of the organic light-emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling. It refers to the layer that plays a role. The hole blocking layer includes a hole blocking material. Examples of the hole blocking material include azine derivatives 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.
상기 전자 주입 및 수송층은 전극으로부터 전자를 주입하고, 수취된 전자를 발광층까지 수송하는 전자수송층 및 전자주입층의 역할을 동시에 수행하는 층으로, 상기 발광층 또는 상기 정공저지층 상에 형성된다. 이러한 전자 주입 및 수송물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 전자 주입 및 수송물질의 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물; 트리아진 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 또는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물, 또는 질소 함유 5원환 유도체 등과 함께 사용할 수도 있으나, 이에 한정되는 것은 아니다. The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer, injecting electrons from an electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. As such an electron injection and transport material, a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons, is suitable. Specific examples of electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complex; Triazine derivatives, etc., but are not limited to these. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds. , or a nitrogen-containing 5-membered ring derivative, etc., but is not limited thereto.
상기 금속 착체 화합물로서는 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.Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.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.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.Additionally, the compound represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The preparation of the compound represented by Formula 1 and an organic light-emitting device containing the same 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.
제조예Manufacturing example 1: 화합물 1의 제조 1: Preparation of Compound 1
단계 1-1: N-(비페닐-4-일)-5-Step 1-1: N-(biphenyl-4-yl)-5- 브로모비페닐Bromobiphenyl -2--2- 아민의Amin's 제조 manufacturing
질소 분위기에서 1000 mL 둥근 바닥 플라스크에 화합물 N-([1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민(100.0 g, 311.52 mmol) 및 NBS(55.46 g, 310.52 mmol)를 DMF 600 mL에 완전히 녹인 후, 5 시간 동안 상온에서 교반하였다. filter하여 얻은 물질을 에틸아세테이트 850 mL로 재결정하여 표제 화합물(89.91 g, 수율 72%)을 제조하였다.Compound N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (100.0 g, 311.52 mmol) and NBS in a 1000 mL round bottom flask under nitrogen atmosphere. (55.46 g, 310.52 mmol) was completely dissolved in 600 mL of DMF and stirred at room temperature for 5 hours. The material obtained through filtering was recrystallized with 850 mL of ethyl acetate to prepare the title compound (89.91 g, yield 72%).
MS[M+H]+= 400MS[M+H] + = 400
단계 1-2: 화합물 A-1의 제조Step 1-2: Preparation of Compound A-1
질소 분위기에서 500 mL 둥근 바닥 플라스크에 상기 단계 1-1에서 제조한 화합물 N-(비페닐-4-일)-5-브로모비페닐-2-아민(15.0 g, 37.50 mmol) 및 화합물 b1(7.43 g, 37.50 mmol)을 테트라하이드로퓨란(THF) 300 mL에 완전히 녹인 후 2M 탄산칼륨수용액(150 mL)을 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(1.30 g, 1.13 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고, 무수황산마그네슘으로 건조한 후 감압 농축시키고, 에틸아세테이트 320 mL로 재결정하여 화합물 A-1(12.47 g, 수율 70%)을 제조하였다.Compound N-(biphenyl-4-yl)-5-bromoviphenyl-2-amine (15.0 g, 37.50 mmol) and compound b1 (7.43 mmol) prepared in step 1-1 above were added to a 500 mL round bottom flask in a nitrogen atmosphere. g, 37.50 mmol) was completely dissolved in 300 mL of tetrahydrofuran (THF), then 2M potassium carbonate aqueous solution (150 mL) was added, tetrakis(triphenylphosphine)palladium (1.30 g, 1.13 mmol) was added, and then 3 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 320 mL of ethyl acetate to prepare Compound A-1 (12.47 g, yield 70%).
MS[M+H]+= 474MS[M+H] + = 474
단계 1-3: 화합물 1의 제조Step 1-3: Preparation of Compound 1
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A-1(9.72 g, 20.56mmol), 및 화합물 a1(6.50 g, 19.58 mmol)을 자일렌 280 mL에 완전히 녹인 후 NaOtBu(2.82 g, 29.37 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.20 g, 0.39 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 화합물 1(7.44 g, 수율: 52%)를 제조하였다.Compound A-1 (9.72 g, 20.56 mmol) and compound a1 (6.50 g, 19.58 mmol) were completely dissolved in 280 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (2.82 g, 29.37 mmol) was added. Then, bis(tri-tert-butylphosphine)palladium(0) (0.20 g, 0.39 mmol) was added, and then heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to prepare Compound 1 (7.44 g, yield: 52%).
MS[M+H]+= 726MS[M+H] + = 726
제조예Manufacturing example 2: 화합물 2의 제조 2: Preparation of Compound 2
상기 제조예 1에서 화합물 b1 대신 화합물 b2를 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-2를 제조하였다.Compound A-2 was prepared using the same method as Preparation Example 1, except that Compound b2 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A-2(9.69 g, 20.48mmol), 및 화합물 a2(5.50 g, 19.50 mmol)을 자일렌 290 mL에 완전히 녹인 후 NaOtBu(4.22 g, 43.95 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.15 g, 0.29 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 화합물 2(8.24 g, 수율: 62%)를 제조하였다.Next, Compound A-2 (9.69 g, 20.48 mmol) and Compound a2 (5.50 g, 19.50 mmol) were completely dissolved in 290 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (4.22 g, 43.95 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 0.29 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare Compound 2 (8.24 g, yield: 62%).
MS[M+H]+= 676MS[M+H] + = 676
제조예Manufacturing example 3: 화합물 3의 제조 3: Preparation of Compound 3
상기 제조예 1에서 화합물 b1 대신 화합물 b3을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-3을 제조하였다.Compound A-3 was prepared using the same method as Preparation Example 1, except that Compound b3 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A-3(7.93 g, 16.76mmol), 및 화합물 a3(4.50 g, 15.96 mmol)을 자일렌 230 mL에 완전히 녹인 후 NaOtBu(2.30 g, 23.94 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.16 g, 0.32 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 3(6.36 g, 수율: 59%)를 제조하였다.Next, Compound A-3 (7.93 g, 16.76 mmol) and Compound a3 (4.50 g, 15.96 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (2.30 g, 23.94 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.32 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 3 (6.36 g, yield: 59%).
MS[M+H]+= 676MS[M+H] + = 676
제조예Manufacturing example 4: 화합물 4의 제조 4: Preparation of Compound 4
상기 제조예 1에서 화합물 b1 대신 화합물 b4를 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-4를 제조하였다.Compound A-4 was prepared using the same method as Preparation Example 1, except that Compound b4 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B-1(12.24 g, 22.30mmol), 및 화합물 a4(6.50 g, 21.24 mmol)을 자일렌 230 mL에 완전히 녹인 후 NaOtBu(3.06 g, 31.86 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.22 g, 0.42 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 280 mL으로 재결정하여 화합물 4(10.07 g, 수율: 61%)를 제조하였다.Next, Compound B-1 (12.24 g, 22.30 mmol) and Compound a4 (6.50 g, 21.24 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and then NaOtBu (3.06 g, 31.86 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.22 g, 0.42 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare compound 4 (10.07 g, yield: 61%).
MS[M+H]+= 776MS[M+H] + = 776
제조예Manufacturing example 5: 화합물 5의 제조 5: Preparation of Compound 5
상기 제조예 1에서 화합물 b1 대신 화합물 b5를 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-5를 제조하였다.Compound A-5 was prepared using the same method as Preparation Example 1, except that Compound b5 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B-2(15.23 g, 27.74mmol), 및 화합물 a5(6.50 g, 26.42 mmol)을 자일렌 260 mL에 완전히 녹인 후 NaOtBu(3.81 g, 39.63 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.27 g, 0.53 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 210 mL으로 재결정하여 화합물 5(9.74 g, 수율: 51%)를 제조하였다.Next, Compound B-2 (15.23 g, 27.74 mmol) and Compound a5 (6.50 g, 26.42 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and then NaOtBu (3.81 g, 39.63 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.27 g, 0.53 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate to prepare Compound 5 (9.74 g, yield: 51%).
MS[M+H]+= 716MS[M+H] + = 716
제조예Manufacturing example 6: 화합물 6의 제조 6: Preparation of Compound 6
상기 제조예 1에서 화합물 b1 대신 화합물 b6을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-6을 제조하였다.Compound A-6 was prepared using the same method as Preparation Example 1, except that Compound b6 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B-3(12.10 g, 22.04mmol), 및 화합물 a6(5.50 g, 20.99 mmol)을 자일렌 240 mL에 완전히 녹인 후 NaOtBu(3.03 g, 31.49 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.21 g, 0.42 mmol)을 넣은 후 35간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 화합물 6(9.74 g, 수율: 51%)를 제조하였다.Next, Compound B-3 (12.10 g, 22.04 mmol) and Compound a6 (5.50 g, 20.99 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (3.03 g, 31.49 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.21 g, 0.42 mmol) was added, followed by heating and stirring for 35 minutes. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to prepare compound 6 (9.74 g, yield: 51%).
MS[M+H]+= 732MS[M+H] + = 732
제조예Manufacturing example 7: 화합물 7의 제조 7: Preparation of compound 7
상기 제조예 1에서 화합물 b1 대신 화합물 b7을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-7을 제조하였다.Compound A-7 was prepared using the same method as Preparation Example 1, except that Compound b7 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C-1(14.64 g, 26.66 mmol), 및 화합물 a7(6.50 g, 25.39 mmol)을 자일렌 230 mL에 완전히 녹인 후 NaOtBu(3.66 g, 38.09 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.26 g, 0.51 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 화합물 7(6.88 g, 수율: 37%)를 제조하였다.Next, Compound C-1 (14.64 g, 26.66 mmol) and Compound a7 (6.50 g, 25.39 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (3.66 g, 38.09 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.26 g, 0.51 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to prepare compound 7 (6.88 g, yield: 37%).
MS[M+H]+= 726MS[M+H]+= 726
제조예Manufacturing example 8: 화합물 8의 제조 8: Preparation of compound 8
상기 제조예 1에서 화합물 b1 대신 화합물 b8을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-8을 제조하였다.Compound A-8 was prepared using the same method as Preparation Example 1, except that Compound b8 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C-2(12.17 g, 22.16mmol), 및 화합물 a8(6.50 g, 21.10 mmol)을 자일렌 250 mL에 완전히 녹인 후 NaOtBu(3.04 g, 31.66 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.22 g, 0.42 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 화합물 8(11.55 g, 수율: 70%)를 제조하였다.Next, Compound C-2 (12.17 g, 22.16 mmol) and Compound a8 (6.50 g, 21.10 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (3.04 g, 31.66 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.22 g, 0.42 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to prepare compound 8 (11.55 g, yield: 70%).
MS[M+H]+= 778MS[M+H] + = 778
제조예Manufacturing example 9: 화합물 9의 제조 9: Preparation of Compound 9
상기 제조예 1에서 화합물 b1 대신 화합물 b9를 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-9를 제조하였다.Compound A-9 was prepared using the same method as Preparation Example 1, except that Compound b9 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 D-1(16.60 g, 27.13mmol), 및 화합물 a9(7.50 g, 26.60 mmol)을 자일렌 230 mL에 완전히 녹인 후 NaOtBu(3.83 g, 39.89 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.14 g, 0.27 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 테트라하이드로퓨란 230 mL으로 재결정하여 화합물 9(13.27 g, 수율: 61%)를 제조하였다.Next, Compound D-1 (16.60 g, 27.13 mmol) and Compound a9 (7.50 g, 26.60 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (3.83 g, 39.89 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.14 g, 0.27 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 230 mL of tetrahydrofuran to prepare compound 9 (13.27 g, yield: 61%).
MS[M+H]+= 778MS[M+H]+= 778
제조예Manufacturing example 10: 화합물 10의 제조 10: Preparation of compound 10
상기 제조예 1에서 화합물 b1 대신 화합물 b10을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법을 사용하여, 화합물 A-10을 제조하였다.Compound A-10 was prepared using the same method as Preparation Example 1, except that Compound b10 was used instead of Compound b1 in Preparation Example 1.
다음으로, 질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 D-2(11.21 g, 17.93mmol), 및 화합물 a10(5.50 g, 17.08 mmol)을 자일렌 240 mL에 완전히 녹인 후 NaOtBu(2.46 g, 25.62 mmol)을 첨가하고, 비스(트리-tert-부틸포스핀) 팔라듐(0)(0.17 g, 0.34 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 화합물 10(8.87 g, 수율: 60%)를 제조하였다.Next, Compound D-2 (11.21 g, 17.93 mmol) and Compound a10 (5.50 g, 17.08 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round bottom flask under a nitrogen atmosphere, and then NaOtBu (2.46 g, 25.62 mmol) ) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.34 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare compound 10 (8.87 g, yield: 60%).
MS[M+H]+= 868MS[M+H] + = 868
실시예Example 1: 유기 발광 소자의 제조 1: Manufacturing of organic light emitting device
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 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150Å)을 진공 증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 50Å으로 상기 제조예 1에서 제조한 화합물 1을 진공 증착하여 전자억제층을 형성하였다. On the ITO transparent electrode, which is the anode prepared in this way, the compounds of the following compound HI1 and the following compound HI2 were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by the following chemical formula HT1 on the hole injection layer. Next, Compound 1 prepared in Preparation Example 1 was vacuum deposited on the hole transport layer with a film thickness of 50 Å to form an electron blocking layer.
이어서, 상기 전자억제층 위에 막 두께 200Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. Subsequently, a compound represented by the following formula BH and a compound represented by the following formula BD were vacuum deposited on the electron blocking layer at a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.
상기 발광층 위에 막 두께 50Å으로 하기 화학식 HB1으로 표시되는 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 310Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. A hole blocking layer was formed by vacuum depositing a compound represented by the following chemical formula HB1 with a film thickness of 50 Å on the light emitting layer. Next, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
상기의 과정에서 유기물의 증착속도는 0.4~0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2ⅹ10-7 ~ 5ⅹ10-6 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 5×10 -6 torr.
실시예Example 2 내지 2 to 실시예Example 10 10
제조예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of the compounds of Preparation Example 1.
비교예Comparative example 1 내지 4 1 to 4
제조예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 EB1, EB2, EB3 및 EB4의 화합물을 하기와 같다.An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used instead of the compounds of Preparation Example 1. The compounds EB1, EB2, EB3, and EB4 used in Table 1 below are as follows.
실험예Experiment example 1 One
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light-emitting devices manufactured in the examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
(전자억제층)compound
(electron suppression layer)
(V
@10mA/cm2)Voltage
(V
@10mA/cm 2 )
(cd/A
@10mA/cm2)efficiency
(cd/A
@10mA/cm 2 )
(x,y)Color coordinates
(x,y)
(hr)T95
(hr)
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자억제층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.As shown in Table 1, the organic light-emitting device using the compound of the present invention as an electron blocking layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
구체적으로, 실시예 1 내지 10에서 'N원자'와 '치환 또는 비치환된 비페닐릴기'가 비페닐-1,4-디일로 연결된 아민계 물질을 전자억제층으로 사용한 유기 발광 소자는, 아민기의 치환기 중 하나로 플루오레닐을 갖는 화합물 EB1을 사용한 비교예 1, 비페닐-1,4-디일에 플루오로기가 연결된 화합물 EB2를 사용한 비교예 2, 비페닐-1,4-디일에 치환기가 없는 화합물 EB4를 사용한 비교예 4, 비페닐-1,4-디일에 페닐기가 연결된 화합물 EB3을 사용한 비교예 3의 유기 발광 소자에 비하여, 저전압, 고효율 및 장수명의 특성을 보이는 것을 알 수 있었다.Specifically, in Examples 1 to 10, the organic light-emitting device using an amine-based material in which the 'N atom' and the 'substituted or unsubstituted biphenylyl group' are linked by biphenyl-1,4-diyl as the electron suppressing layer is an amine. Comparative Example 1 using compound EB1 having fluorenyl as one of the substituents of the group, Comparative Example 2 using compound EB2 in which a fluoro group is linked to biphenyl-1,4-diyl, and biphenyl-1,4-diyl having a substituent Compared to the organic light emitting device of Comparative Example 4 using the compound EB4 without the compound EB4 and Comparative Example 3 using the compound EB3 in which a phenyl group is linked to biphenyl-1,4-diyl, it was found to exhibit the characteristics of low voltage, high efficiency and long lifespan.
1: 기판 2: 양극
3: 정공수송층 4: 발광층
5: 전자주입 및 수송층 6: 음극
7: 정공주입층 8: 전자억제층
9: 정공저지층 1: Substrate 2: Anode
3: hole transport layer 4: light emitting layer
5: Electron injection and transport layer 6: Cathode
7: hole injection layer 8: electron suppression layer
9: Hole blocking layer
Claims (8)
[화학식 1]
상기 화학식 1에서,
L1 및 L2는 각각 독립적으로, 단일결합; 또는 C6-20 아릴렌이고,
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 안트라세닐, 트리페닐레닐, 파이레닐, 크라이세닐, 나프타세닐, 디벤조퓨라닐, 디벤조티오페닐, 벤조나프토퓨라닐, 또는 벤조나프토티오페닐이고,
Ar3는 비치환되거나, 또는 페닐, 비페닐릴, 또는 터페닐릴로 치환된 비페닐릴이다.
Compound represented by Formula 1:
[Formula 1]
In Formula 1,
L 1 and L 2 are each independently a single bond; or C 6-20 arylene,
Ar 1 and Ar 2 are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, dibenzofuranyl, dibenzo thiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,
Ar 3 is unsubstituted or biphenylyl substituted with phenyl, biphenylyl, or terphenylyl.
L1 및 L2는 각각 독립적으로, 단일결합, 페닐렌, 비페닐디일, 또는 나프틸렌인,
화합물.
According to paragraph 1,
L 1 and L 2 are each independently a single bond, phenylene, biphenyldiyl, or naphthylene,
compound.
Ar1 및 Ar2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
상기에서,
R은 수소이다.
According to paragraph 1,
Ar 1 and Ar 2 are each independently selected from the group consisting of:
compound:
In the above,
R is hydrogen.
Ar3는 비페닐릴, 터페닐릴, 또는 쿼터페닐릴인,
화합물.
According to paragraph 1,
Ar 3 is biphenylyl, terphenylyl, or quarterphenylyl,
compound.
Ar3는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
According to paragraph 1,
Ar 3 is any one selected from the group consisting of:
compound:
상기 화합물은 하기 화학식 1-1 내지 1-3 중 어느 하나로 표시되는,
화합물:
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
상기 화학식 1-1 내지 1-3에서,
Ar1 및 Ar2에 대한 설명은 제1항에서 정의한 바와 같고,
Ph는 페닐을 의미하고,
n은 0 또는 1이고,
m은 0, 1, 또는 2이다.
According to paragraph 1,
The compound is represented by any one of the following formulas 1-1 to 1-3,
compound:
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
In Formulas 1-1 to 1-3,
The description of Ar 1 and Ar 2 is as defined in paragraph 1,
Ph means phenyl,
n is 0 or 1,
m is 0, 1, or 2.
상기 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인, 화합물:
According to paragraph 1,
The compound is any one selected from the group consisting of the following compounds:
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