KR20210020842A - 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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- KR20210020842A KR20210020842A KR1020200102763A KR20200102763A KR20210020842A KR 20210020842 A KR20210020842 A KR 20210020842A KR 1020200102763 A KR1020200102763 A KR 1020200102763A KR 20200102763 A KR20200102763 A KR 20200102763A KR 20210020842 A KR20210020842 A KR 20210020842A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 202
- -1 naphthylphenyl Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
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- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 40
- 239000011368 organic material Substances 0.000 abstract description 18
- 239000000126 substance Substances 0.000 abstract description 11
- 239000010410 layer Substances 0.000 description 111
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- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 60
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 60
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 35
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 150000004982 aromatic amines Chemical class 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
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- OMEKXUAFGFANKD-UHFFFAOYSA-N c1ccc2[s]c3cc(-c4nc(-[n](c(cc5)c6c7c5[o]c5c7c(-c7ccccc7-7)ccc5)c5c6c-7ccc5)nc5ccccc45)ccc3c2c1 Chemical compound c1ccc2[s]c3cc(-c4nc(-[n](c(cc5)c6c7c5[o]c5c7c(-c7ccccc7-7)ccc5)c5c6c-7ccc5)nc5ccccc45)ccc3c2c1 OMEKXUAFGFANKD-UHFFFAOYSA-N 0.000 description 1
- VTGIADWPFRBSRR-UHFFFAOYSA-N c1ccc2[s]c3cccc(-c4c(-[n](c5ccc6[o]c7cccc(-c8c-9cccc8)c7c6c55)c6c5c-9ccc6)nc(cccc5)c5n4)c3c2c1 Chemical compound c1ccc2[s]c3cccc(-c4c(-[n](c5ccc6[o]c7cccc(-c8c-9cccc8)c7c6c55)c6c5c-9ccc6)nc(cccc5)c5n4)c3c2c1 VTGIADWPFRBSRR-UHFFFAOYSA-N 0.000 description 1
- YKOHCEJCTPVQRV-UHFFFAOYSA-N c1ccc2c(cccc3)c3c(-c3c(-[n](c(cc4)c5c6c4[o]c4cccc(-c7c-8cccc7)c64)c4c5c-8ccc4)nc(cccc4)c4n3)cc2c1 Chemical compound c1ccc2c(cccc3)c3c(-c3c(-[n](c(cc4)c5c6c4[o]c4cccc(-c7c-8cccc7)c64)c4c5c-8ccc4)nc(cccc4)c4n3)cc2c1 YKOHCEJCTPVQRV-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- 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
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- 239000010931 gold Substances 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
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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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
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- 238000010030 laminating Methods 0.000 description 1
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
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- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 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
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- 239000007773 negative electrode material Substances 0.000 description 1
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- 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
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
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- 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
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- 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- 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
- 150000003918 triazines Chemical class 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
- 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
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
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- H01L51/0071—
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- H01L51/5012—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
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, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are 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. The organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.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 a novel compound and an organic light emitting device comprising the same.
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,
X는 O 또는 S이고,X is O or S,
L은 단일결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고,L is a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms of N, O and S,
Ar은 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고, Ar is a substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms of N, O and S,
R1 내지 R4는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,R 1 to R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
a는 0 내지 3의 정수이고,a is an integer from 0 to 3,
b는 0 내지 4의 정수이고, b is an integer from 0 to 4,
c는 0 내지 3의 정수이고,c is an integer from 0 to 3,
d는 0 내지 2의 정수이고,d is an integer from 0 to 2,
a, b, c 및 d가 각각 2 이상인 경우, 괄호 안의 치환기들은 서로 동일하거나 상이하다. When a, b, c and d are each 2 or more, the substituents in parentheses are the same or different from each other.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하는 유기 발광 소자로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes a compound represented by
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용되어, 유기 발광 소자의 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. The compound represented by Chemical Formula 1 is used as a material for the organic material layer of the organic light-emitting device, and thus the efficiency of the organic light-emitting device can be improved, low driving voltage, and/or lifetime characteristics can be improved.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판(1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자억제층(7), 정공저지층(8), 전자주입 및 수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 1 shows an example of an organic light emitting device comprising a
2 shows a
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail to aid the understanding of the present invention.
(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.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy 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 it means 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 substituents connected among the above-exemplified substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to 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 the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having 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 ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic 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 the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having 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 is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되는 것은 아니다.In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group 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 a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, and the like, but are not limited thereto.
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 a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary 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, and the like, but are not limited thereto.
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 is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but 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, 비페닐이기, 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary 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, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, 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 bonded to each other to form a spiro structure. When the fluorenyl group is substituted, Etc. However, it 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 잔텐(xanthene), 티오잔텐(thioxanthen), 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, 이에 한정되는 것은 아니다.In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, 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 ( phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 방향족 고리는 고리 형성 원자로서 탄소만을 포함하면서 분자 전체가 방향족성(aromaticity)을 갖는 축합단환 또는 축합다환 고리를 의미한다. 상기 방향족 고리의 탄소수는 6 내지 60, 또는 6 내지 30, 또는 6 내지 20이나, 이에 한정되는 것은 아니다. 또한, 상기 방향족 고리로는 벤젠 고리, 나프탈렌 고리, 안트라센 고리, 페난쓰렌 고리, 파이렌 고리 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aromatic ring refers to a condensed monocyclic or condensed polycyclic ring including only carbon as a ring-forming atom and having aromaticity in the entire molecule. The number of carbon atoms in the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. In addition, the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a pyrene ring, but is not limited thereto.
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 the present specification, the aryl group in 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 the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the above-described description of heteroaryl may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
(화합물)(compound)
상기 화학식 1로 표시되는 화합물은, 벤조퓨로[2,3-c]카바졸의 1번 및 12번 위치가 1,2-페닐렌 링커에 의해 연결된 8각형 코어 및 상기 코어에 포함된 N 원자가 헤테로아릴 치환기로 치환된 구조를 갖는다. 이러한 화합물은 상기 8각형 코어 구조를 포함하지 않는 화합물 및 상기 코어에 포함된 N 원자에 헤테로아릴이 아닌 다른 치환기가 치환된 화합물에 비하여, 도펀트로의 에너지 전달율이 높고, 전자 및 정공에 대한 안정도가 향상될 수 있다. 이에 따라, 이러한 화합물을 채용한 유기 발광 소자의 효율 및 수명이 동시에 향상될 수 있다.The compound represented by
바람직하게는, L은 단일결합; 또는 비치환되거나 또는 중수소로 치환된 C6-20 아릴렌일 수 있다. 구체적으로, 상기 중수소로 치환된 C6-20 아릴렌은 모든 수소가 중수소로 치환되어 있을 수 있다.Preferably, L is a single bond; Or it may be unsubstituted or C 6-20 arylene substituted with deuterium. Specifically, in the C 6-20 arylene substituted with deuterium, all hydrogens may be substituted with deuterium.
보다 바람직하게는, L은 단일결합; 비치환되거나 또는 중수소로 치환된 페닐렌; 또는 비치환되거나 또는 중수소로 치환된 나프틸렌일 수 있다. 구체적으로, L은 단일결합, 페닐렌, 또는 나프틸렌일 수 있다. More preferably, L is a single bond; Phenylene unsubstituted or substituted with deuterium; Or it may be unsubstituted or naphthylene substituted with deuterium. Specifically, L may be a single bond, phenylene, or naphthylene.
예를 들어, L은 단일결합 또는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있으나, 이에 한정되는 것은 아니다:For example, L may be a single bond or any one selected from the group consisting of, but is not limited thereto:
. .
바람직하게는, Ar은 비치환되거나, 또는 중수소 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환된, N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴일 수 있다. Preferably, Ar is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl, C 2- containing one or more heteroatoms of N, O and S. 60 heteroaryl.
보다 바람직하게는, Ar은 비치환되거나, 또는 중수소 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환된, 적어도 1개의 N 원자를 포함하는 C2-60 헤테로아릴; 비치환되거나, 또는 중수소 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환된, 적어도 1개의 N 원자 및 적어도 1개의 O 원자를 포함하는 C2-60 헤테로아릴; 또는 비치환되거나, 또는 중수소 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환된, 적어도 1개의 N 원자 및 적어도 1개의 S 원자를 포함하는 C2-60 헤테로아릴일 수 있다.More preferably, Ar is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl, C 2-60 heteroaryl including at least one N atom; C 2-60 heteroaryl containing at least 1 N atom and at least 1 O atom, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl; Or unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl, and may be a C 2-60 heteroaryl containing at least one N atom and at least one S atom. have.
구체적으로, Ar은 하기 화학식 2A 내지 2D로 표시되는 치환기 중 어느 하나일 수 있다: Specifically, Ar may be any one of the substituents represented by the following formulas 2A to 2D:
상기 화학식 2A 내지 2D에서,In Formulas 2A to 2D,
Y는 O 또는 S이고,Y is O or S,
Q 중 하나는 상기 화학식 1의 L과 결합되는 C이고, 나머지는 각각 독립적으로, N 또는 CR이고, 단, 나머지 중 적어도 하나는 N이고, One of Q is C bonded to L in
R, R' 및 R"는 각각 독립적으로, 수소, 중수소, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R, R'and R" are each independently hydrogen, deuterium, C 6-20 aryl; Or C 2-20 heteroaryl comprising one or more heteroatoms of N, O and S,
여기서, 상기 R, R' 및 R"는 비치환되거나, 또는 중수소, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되고,Here, the R, R'and R" are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl,
m은 0 내지 4의 정수이고,m is an integer from 0 to 4,
n은 0 내지 6의 정수이다.n is an integer from 0 to 6.
보다 구체적으로, Ar은 하기 화학식으로 표시되는 치환기 중 어느 하나일 수 있으나, 이에 한정되는 것은 아니다. More specifically, Ar may be any one of the substituents represented by the following formula, but is not limited thereto.
상기에서,Above,
Y는 O 또는 S이고,Y is O or S,
Z는 각각 독립적으로, N 또는 CH이고, 단, Z 중 적어도 하나는 N이고,Z is each independently N or CH, provided that at least one of Z is N,
R, R' 및 R"는 각각 독립적으로, 수소, 중수소, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R, R'and R" are each independently hydrogen, deuterium, C 6-20 aryl; Or C 2-20 heteroaryl comprising one or more heteroatoms of N, O and S,
여기서, 상기 R, R' 및 R"는 비치환되거나, 또는 중수소, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되고,Here, the R, R'and R" are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl,
m은 0 내지 4의 정수이고,m is an integer from 0 to 4,
n은 0 내지 6의 정수이다.n is an integer from 0 to 6.
바람직하게는, 상기에서,Preferably, in the above,
Z는 모두 N이고,Z is all N,
R 및 R'는 각각 독립적으로, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R and R'are each independently C 6-20 aryl; Or C 2-20 heteroaryl containing one or more heteroatoms of N, O and S,
여기서, R 및 R'는 비치환되거나, 또는 중수소, 메틸, 페닐 및 나프틸로 구성되는 군으로부터 선택되는 1개 또는 2개의 치환기로 치환되고, Here, R and R'are unsubstituted or substituted with one or two substituents selected from the group consisting of deuterium, methyl, phenyl and naphthyl,
R"는 수소 또는 중수소일 수 있다.R" may be hydrogen or deuterium.
보다 바람직하게는, More preferably,
R 및 R'는 각각 독립적으로, 페닐, 나프틸페닐, 비페닐릴, 터페닐릴, 나프틸, 페닐나프틸, 페난쓰레닐, 9,9-디메틸플루오레닐, 카바졸일, 9-페닐카바졸일, 디벤조퓨라닐, 또는 디벤조티오페닐이고,R and R'are each independently, phenyl, naphthylphenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, phenanthrenyl, 9,9-dimethylfluorenyl, carbazolyl, 9-phenylcarba Zolyl, dibenzofuranyl, or dibenzothiophenyl,
R"는 수소, 또는 중수소일 수 있다.R" may be hydrogen or deuterium.
예를 들어, R 및 R'는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있으나, 이에 한정되는 것은 아니다:For example, R and R'may each independently be any one selected from the group consisting of, but are not limited thereto:
. .
또한, m은 0, 1, 2, 3, 또는 4이고, n은 0, 1, 2, 3, 4, 5, 또한 6일 수 있다.Further, m may be 0, 1, 2, 3, or 4, and n may be 0, 1, 2, 3, 4, 5, or 6.
바람직하게는, R1 내지 R4는 각각 독립적으로, 수소, 또는 중수소이다. 이때, R1의 치환기의 개수를 나타내는 a는 0, 1, 2, 또는 3이고, R2의 치환기의 개수를 나타내는 b는 0, 1, 2, 3, 또는 4이고, R3의 치환기의 개수를 나타내는 c는 0, 1, 2, 또는 3이고, R4의 치환기의 개수를 나타내는 d는 0, 1, 또는 2이다. 예를 들어, a, b, c 및 d는 각각 독립적으로, 0 또는 1이다.Preferably, R 1 to R 4 are each independently hydrogen or deuterium. At this time, a representing the number of substituents of R 1 is 0, 1, 2, or 3, b representing the number of substituents of R 2 is 0, 1, 2, 3, or 4, and the number of substituents of R 3 C represents 0, 1, 2, or 3, and d represents the number of substituents of R 4 is 0, 1, or 2. For example, a, b, c and d are each independently 0 or 1.
구체적으로, 상기 화학식 1로 표시되는 상기 화합물은 하기 화학식 3a, 3b-1, 3b-2, 3c-1 내지 3c-4 및 3d-1 내지 3d-4 중 어느 하나로 표시될 수 있다:Specifically, the compound represented by
상기 화학식 3a, 3b-1, 3b-2, 3c-1 내지 3c-4 및 3d-1 내지 3d-4 에서,In Formulas 3a, 3b-1, 3b-2, 3c-1 to 3c-4, and 3d-1 to 3d-4,
Y는 O 또는 S이고,Y is O or S,
Z는 각각 독립적으로, N 또는 CH이고, 단, Z 중 적어도 하나는 N이고,Z is each independently N or CH, provided that at least one of Z is N,
R 및 R'는 각각 독립적으로, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R and R'are each independently C 6-20 aryl; Or C 2-20 heteroaryl containing one or more heteroatoms of N, O and S,
여기서, 상기 R 및 R'는 비치환되거나, 또는 중수소, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되고,Wherein R and R'are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl,
X 및 L은 상기 화학식 1에서 정의한 바와 같다.X and L are as defined in
상기 화학식 3a, 3b-1, 3b-2, 3c-1 내지 3c-4 및 3d-1 내지 3d-4 에서,In Formulas 3a, 3b-1, 3b-2, 3c-1 to 3c-4, and 3d-1 to 3d-4,
Z는 모두 N일 수 있고,Z can be all N,
R 및 R'는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다::R and R'may each independently be any one selected from the group consisting of:
. .
예를 들어, 상기 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나이다: For example, the compound is any one selected from the group consisting of the following compounds:
한편, 상기 화학식 1로 표시되는 화합물은 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다. On the other hand, the compound represented by
[반응식 1][Scheme 1]
상기 반응식 1에서, X"는 할로겐이고, 바람직하게는 브로모, 또는 클로로이고, 다른 치환기에 대한 정의는 앞서 설명한 바와 같다.In
구체적으로, 상기 화학식 1로 표시되는 화합물은 아민 치환 반응을 통해 출발물질 SM1 및 SM2가 결합하여 제조된다. 이러한 아민 치환 반응은 팔라듐 촉매와 염기의 존재 하에 수행하는 것이 바람직하다. 또한, 상기 아민 치환 반응을 위한 반응기는 적절히 변경될 수 있고, 화학식 1로 표시되는 화합물의 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.Specifically, the compound represented by
(유기 발광 소자)(Organic light emitting device)
또한, 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 발광층을 포함하는 유기 발광 소자로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present invention provides an organic light-emitting device including the compound represented by
또한, 본 발명에 따른 유기 발광 소자는, 제1 전극이 양극이고, 제2 전극이 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 제1 전극이 음극이고, 제2 전극이 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 in which a first electrode is an anode and a second electrode is a cathode. Can be In addition, the organic light-emitting device according to the present invention has an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate in which the first electrode is the cathode and the second electrode is the anode. Can be 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), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 1 shows an example of an organic light emitting device comprising a
도 2는 기판(1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자억제층(7), 정공저지층(8), 전자주입 및 수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다.2 shows a
본 발명에 따른 유기 발광 소자는, 상기 발광층이 본 발명에 따른 화합물을 포함하고, 상술한 방법과 같이 제조되는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조할 수 있다.The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that the emission layer includes the compound according to the present invention and is manufactured as described above.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 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 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. For example, the organic light-emitting device according to the present invention may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.
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 such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.For example, the first electrode is an anode, 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 화합물 등이 있으나, 이에 한정되는 것은 아니다. As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode 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 compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
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, 이에 한정되는 것은 아니다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material 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 a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
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 유기물 층의 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 화합물 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds, but are not limited thereto.
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. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 화합물, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 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 emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
일 구현예에 따른 유기 발광 소자는 상기 정공수송층 상에 전자억제층을 더 포함할 수 있다. 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 전자억제물질을 포함하고, 이러한 전자억제물질의 예로 상기 화학식 1로 표시되는 화합물을 사용하거나, 또는 아릴아민 계열의 유기물 등을 사용할 수 있으나, 이에 한정되는 것은 아니다.The organic light-emitting device according to an embodiment may further include an electron suppression layer on the hole transport layer. The electron suppression layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. It refers to the layer that plays a role in improving the value. The electron-suppressing layer includes an electron-suppressing material, and examples of the electron-suppressing material include a compound represented by
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료로는 상술한 화학식 1로 표시되는 화합물이 사용될 수 있다. 또한, 호스트 재료로는 상기 화학식 1로 표시되는 화합물 이외에 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 추가로 사용할 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 emission layer may include a host material and a dopant material. As the host material, the compound represented by
또한, 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.Further, the dopant material includes an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
보다 구체적으로는, 상기 도펀트 재료로 하기와 같은 화합물이 사용될 수 있으나, 이에 한정되는 것은 아니다:More specifically, the following compound may be used as the dopant material, but is not limited thereto:
. .
또한, 일 구현예에 따른 유기 발광 소자는 상기 발광층 상에 정공저지층을 더 포함할 수 있다. 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 아진류 유도체; 트리아졸 유도체; 옥사디아졸 유도체; 페난트롤린 유도체; 포스핀옥사이드 유도체 등의 전자흡인기가 도입된 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다.In addition, the organic light-emitting device according to an embodiment may further include a hole blocking layer on the emission layer. The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by increasing the probability of hole-electron coupling by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is 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, 플루오레닐리덴 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 serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As such an electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives and the like, but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or a nitrogen-containing 5-membered cyclic derivative, but may be used, but is not limited thereto.
상기 전자 주입 및 수송층은 전자주입층 및 전자수송층과 같은 별개의 층으로도 형성될 수 있다. 이와 같은 경우, 전자 수송층은 상기 발광층 또는 상기 정공저지층 상에 형성되고, 상기 전자 수송층에 포함되는 전자 수송 물질로는 상술한 전자 주입 및 수송 물질이 사용될 수 있다. 또한, 전자 주입층은 상기 전자 수송층 상에 형성되고, 상기 전자 주입층에 포함되는 전자 주입 물질로는 LiF, NaCl, CsF, Li2O, BaO, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 벤조이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 사용될 수 있다.The electron injection and transport layer may be formed as separate layers such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the emission layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, etc. I can.
또한, 본 발명에 따른 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
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.Preparation of the compound represented by
합성예 및 실시예Synthesis Examples and Examples
본 발명의 화합물은 대표적인 반응으로 Buchwald-Hartwi g couplin g reaction, Heck couplin g reaction, Suzuki couplin g reaction 등을 이용하여 제조되었다.The compounds of the present invention were prepared using Buchwald-Hartwi g couplin g reaction, Heck couplin g reaction, and Suzuki couplin g reaction as representative reactions.
제조예 A. 화합물 a의 제조Preparation Example A. Preparation of compound a
1) 화합물 1-1-3의 제조1) Preparation of compound 1-1-3
(3-하이드록시-9H-카바졸-4-일)보론산 200.0 g (1.0 eq)와 1-브로모-3-플루오로-2-아이오도벤젠 291.58 g (1.1 eq)을 THF 2 L에 넣고 교반한 다음 포타슘 카보네이트 365.26 g (3.0 eq)를 물에 녹여 투입하고 충분히 교반한 후 환류하였다. 이후, 여기에 Pd(t-Bu3P)2 4.50 g (0.01 eq)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1-3 229.06 g 을 얻었다. (수율 73%, MS: [M+H]+= 357)(3-hydroxy-9H-carbazol-4-yl) boronic acid 200.0 g (1.0 eq) and 1-bromo-3-fluoro-2-iodobenzene 291.58 g (1.1 eq) in THF 2 L After stirring, potassium carbonate 365.26 g (3.0 eq) was dissolved in water, added, stirred sufficiently, and refluxed. Then, Pd(t-Bu 3 P) 2 4.50 g (0.01 eq) was added thereto. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 229.06 g of compound 1-1-3. (Yield 73%, MS: [M+H] + = 357)
2) 화합물 1-1-2의 제조2) Preparation of compound 1-1-2
화합물 1-1-3 229.06 g (1.0 eq) 에 K2CO3 266.64 g (3.00 eq) 을 다이에틸아세트아마이드(Dimethylacetamide) 1.5 L에 넣고 환류하여 교반하였다. 2시간 후 반응물을 물에 부어서 결정화를 시킨 후 여과하였다. 여과한 고체를 톨루엔에 완전히 녹인 후 물로 씻어주고 생성물이 녹아있는 용액을 감압 농축하여 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼 크로마토그래피로 정제하여 화합물 1-1-2 144.85 g (수율 67 %, MS: [M+H]+=337)을 얻었다. To 229.06 g (1.0 eq) of compound 1-1-3, 266.64 g ( 3.00 eq) of K 2 CO 3 was added to 1.5 L of diethylacetamide, followed by reflux and stirred. After 2 hours, the reactant was poured into water to crystallize and then filtered. The filtered solid was completely dissolved in toluene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by column chromatography to obtain 144.85 g of compound 1-1-2 (yield 67%, MS: [M+H] + =337).
3) 화합물 1-1-1의 제조3) Preparation of compound 1-1-1
화합물 1-1-2 144.85 g (1.0 eq))와 (2-클로로페닐)보론산 74.11 g, (1.1 eq) 를 THF 1 L에 넣고 교반한 다음 포타슘 카보네이트 178.65 g (3.0 eq)를 물에 녹여 투입하고 충분히 교반한 후 환류하였다. 이후, 여기에 Pd(t-Bu3P)2 2.20 g (0.01 eq)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1-1 122.03 g 을 얻었다. (수율 77%, MS: [M+H]+= 369)Compound 1-1-2 144.85 g (1.0 eq)), (2-chlorophenyl) boronic acid 74.11 g, and (1.1 eq) were added to 1 L of THF, stirred, and then potassium carbonate 178.65 g (3.0 eq) was dissolved in water. It was added and sufficiently stirred, and then refluxed. Then, 2.20 g (0.01 eq) of Pd(t-Bu 3 P) 2 was added thereto. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 122.03 g of compound 1-1-1. (Yield 77%, MS: [M+H] + = 369)
4) 화합물 a의 제조4) Preparation of compound a
화합물 1-1-1 122.03 g (1.0 eq), K3PO4 211.27 g (3.0 eq) 을 DMAc 1L 에 녹여 환류하여 교반하였다. 3 시간 후 반응이 종료되면 물에 부어서 결정화를 시킨 후 여과하였다. 이 후 에틸 아세테이트에 완전히 녹여서 물로 씻어주고 다시 감압하여 용매를 70% 정도 제거하였다. 다시 환류 상태에서 헥산을 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼 크로마토그래피하여 화합물 a 69.26 g (수율 63 %, MS: [M+H]+=332)를 얻었다. Compound 1-1-1 122.03 g (1.0 eq) and K 3 PO 4 211.27 g (3.0 eq) were dissolved in 1 L of DMAc and refluxed and stirred. When the reaction was completed after 3 hours, it was poured into water to crystallize and then filtered. Then, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 69.26 g of a compound a (yield 63%, MS: [M+H] + =332).
제조예 B: 화합물 b의 제조Preparation B: Preparation of compound b
1) 화합물 1-2-3의 제조1) Preparation of compound 1-2-3
(9H-카바졸-4-일)보론산 300.0 g (1.0 eq))와 1-브르모-2-아이오도-3-(메틸설피닐)벤젠 539.48 g, (1.1 eq) 를 THF 4 L에 넣고 교반한 다음 포타슘 카보네이트 589.43 g (3.0 eq)를 물에 녹여 투입하고 충분히 교반한 후 환류하였다. 이후, 여기에 Pd(t-Bu3P)2 7.26 g (0.01 eq)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-2-3 387.87 g 을 얻었다. (수율 71%, MS: [M+H]+= 384)(9H-carbazol-4-yl) boronic acid 300.0 g (1.0 eq)) and 1-bromo-2-iodo-3-(methylsulfinyl)benzene 539.48 g, (1.1 eq) to 4 L of THF After stirring, potassium carbonate 589.43 g (3.0 eq) was dissolved in water and added thereto, stirred sufficiently, and refluxed. Then, 7.26 g (0.01 eq) of Pd(t-Bu 3 P) 2 was added thereto. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 387.87 g of compound 1-2-3. (Yield 71%, MS: [M+H] + = 384)
2) 화합물 1-2-2의 제조2) Preparation of compound 1-2-2
화합물 1-2-3 387.87 g (1.0 eq) 에 황산 1 L에 녹이고 환류하여 교반하였다. 5시간 후 반응물을 물에 부어서 결정화를 시킨 후 여과하였다. 여과한 고체를 톨루엔에 완전히 녹인 후 K3PO4 수용액으로 여러번 씻어 주며 중화 시켰다. 이후 생성물이 녹아있는 용액에 무수황산마그네슘을 넣고 교반한 후 여과하여 감압 농축하여 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼 크로마토그래피로 정제하여 화합물 1-2-2 184.87 g (수율 52 %, MS: [M+H]+=353)을 얻었다. Compound 1-2-3 was dissolved in 1 L of sulfuric acid in 387.87 g (1.0 eq) and stirred under reflux. After 5 hours, the reactant was poured into water to crystallize and then filtered. The filtered solid was completely dissolved in toluene, washed several times with an aqueous K 3 PO 4 solution, and neutralized. Thereafter, anhydrous magnesium sulfate was added to the solution in which the product was dissolved, stirred, filtered, concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by column chromatography to obtain 184.87 g of compound 1-2-2 (yield 52%, MS: [M+H] + =353).
3) 화합물 1-2-1의 제조3) Preparation of compound 1-2-1
화합물 1-2-2 184.87 g (1.0 eq))와 (2-클로로페닐)보론산 90.27 g, (1.1 eq) 를 THF 1.5 L에 넣고 교반한 다음 포타슘 카보네이트 217.62 g (3.0 eq)를 물에 녹여 투입하고 충분히 교반한 후 환류하였다. 이후, 여기에 Pd(t-Bu3P)2 2.68 g (0.01 eq)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-2-1 149.09 g 을 얻었다. (수율 74%, MS: [M+H]+= 384)Compound 1-2-2 184.87 g (1.0 eq)) and 90.27 g of (2-chlorophenyl) boronic acid, and (1.1 eq) were added to 1.5 L of THF, stirred, and then 217.62 g (3.0 eq) of potassium carbonate was dissolved in water. It was added and sufficiently stirred, and then refluxed. Thereafter, 2.68 g (0.01 eq) of Pd(t-Bu 3 P) 2 was added thereto. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 149.09 g of compound 1-2-1. (Yield 74%, MS: [M+H] + = 384)
4) 화합물 b의 제조4) Preparation of compound b
화합물 a-1 149.09 g (1.0 eq), K3PO4 247.33 g (3.0 eq) 을 DMAc 1L 에 녹여 환류하여 교반하였다. 3 시간 후 반응이 종료되면 물에 부어서 결정화를 시킨 후 여과하였다. 이 후 에틸 아세테이트에 완전히 녹여서 물로 씻어주고 다시 감압하여 용매를 70% 정도 제거하였다. 다시 환류 상태에서 헥산을 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼 크로마토그래피하여 화합물 b 82.31 g (수율 61 %, MS: [M+H]+=348)를 얻었다. Compound a-1 149.09 g (1.0 eq), K 3 PO 4 247.33 g (3.0 eq) was dissolved in 1 L of DMAc and stirred under reflux. When the reaction was completed after 3 hours, it was poured into water to crystallize and then filtered. Then, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 82.31 g of a compound b (yield 61%, MS: [M+H] + =348).
합성예 1: 화합물 1의 제조Synthesis Example 1: Preparation of
질소 분위기에서 sub 1 (10 g, 25.4mmol), 화합물 a (8.4 g, 25.4 mmol), 소듐 tert-부톡사이드 (4.9 g, 50.8 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 1 5.6 g 을 얻었다. (수율 32%, MS: [M+H]+= 690)In a nitrogen atmosphere, sub 1 (10 g, 25.4 mmol), compound a (8.4 g, 25.4 mmol), and sodium tert-butoxide (4.9 g, 50.8 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.6 g of
합성예 2: 화합물 2의 제조Synthesis Example 2: Preparation of
질소 분위기에서 sub 2 (10 g, 27.2mmol), 화합물 a (9 g, 27.2 mmol), 소듐 tert-부톡사이드 (5.2 g, 54.4 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 2 10.3 g 을 얻었다. (수율 57%, MS: [M+H]+= 664)In a nitrogen atmosphere, sub 2 (10 g, 27.2 mmol), compound a (9 g, 27.2 mmol), and sodium tert-butoxide (5.2 g, 54.4 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of
합성예 3: 화합물 3의 제조Synthesis Example 3: Preparation of
질소 분위기에서 sub 3 (10 g, 24.5mmol), 화합물 a (8.1 g, 24.5 mmol), 소듐 tert-부톡사이드 (4.7 g, 49 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 3시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 3 6.7 g 을 얻었다. (수율 39%, MS: [M+H]+= 704)In a nitrogen atmosphere, sub 3 (10 g, 24.5 mmol), compound a (8.1 g, 24.5 mmol), and sodium tert-butoxide (4.7 g, 49 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of
합성예 4: 화합물 4의 제조Synthesis Example 4: Preparation of
질소 분위기에서 sub 4 (10 g, 25.4mmol), 화합물 a (8.4 g, 25.4 mmol), 소듐 tert-부톡사이드 (4.9 g, 50.8 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 3시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물4 6.8 g 을 얻었다. (수율 39%, MS: [M+H]+= 690)In a nitrogen atmosphere, sub 4 (10 g, 25.4 mmol), compound a (8.4 g, 25.4 mmol), and sodium tert-butoxide (4.9 g, 50.8 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.8 g of
합성예 5: 화합물 5의 제조Synthesis Example 5: Preparation of
질소 분위기에서 sub 5 (10 g, 28.8mmol), 화합물 a (9.6 g, 28.8 mmol), 소듐 tert-부톡사이드 (5.5 g, 57.7 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.6 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물5 6.5 g 을 얻었다. (수율 35%, MS: [M+H]+= 643)In a nitrogen atmosphere, sub 5 (10 g, 28.8 mmol), compound a (9.6 g, 28.8 mmol), and sodium tert-butoxide (5.5 g, 57.7 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.5 g of
합성예 6: 화합물 6의 제조Synthesis Example 6: Preparation of
질소 분위기에서 sub 6 (10 g, 22.3mmol), 화합물 a (7.4 g, 22.3 mmol), 소듐 tert-부톡사이드 (4.3 g, 44.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.4 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물6 8.1 g 을 얻었다. (수율 49%, MS: [M+H]+= 745)In a nitrogen atmosphere, sub 6 (10 g, 22.3 mmol), compound a (7.4 g, 22.3 mmol), and sodium tert-butoxide (4.3 g, 44.5 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.1 g of
합성예 7: 화합물 7의 제조Synthesis Example 7: Preparation of
질소 분위기에서 sub 7 (10 g, 23.6mmol), 화합물 a (7.8 g, 23.6 mmol), 소듐 tert-부톡사이드 (4.5 g, 47.3 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물7 8 g 을 얻었다. (수율 47%, MS: [M+H]+= 719)In a nitrogen atmosphere, sub 7 (10 g, 23.6 mmol), compound a (7.8 g, 23.6 mmol), and sodium tert-butoxide (4.5 g, 47.3 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8 g of
합성예 8: 화합물 8의 제조Synthesis Example 8: Preparation of
질소 분위기에서 sub 8 (10 g, 24.8mmol), 화합물 a (8.2 g, 24.8 mmol), 소듐 tert-부톡사이드 (4.8 g, 49.6 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물8 9.2 g 을 얻었다. (수율 53%, MS: [M+H]+= 699)In a nitrogen atmosphere, sub 8 (10 g, 24.8 mmol), compound a (8.2 g, 24.8 mmol), and sodium tert-butoxide (4.8 g, 49.6 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of
합성예 9: 화합물 9의 제조Synthesis Example 9: Preparation of
질소 분위기에서 sub 9 (10 g, 26.3 mmol), 화합물 a (8.7 g, 26.3 mmol), 소듐 tert-부톡사이드 (5 g, 52.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물9 5.7 g 을 얻었다. (수율 32%, MS: [M+H]+= 677)In a nitrogen atmosphere, sub 9 (10 g, 26.3 mmol), compound a (8.7 g, 26.3 mmol), and sodium tert-butoxide (5 g, 52.5 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.7 g of
합성예 10: 화합물 10의 제조Synthesis Example 10: Preparation of Compound 10
질소 분위기에서 sub 10 (10 g, 28mmol), 화합물 a (9.3 g, 28 mmol), 소듐 tert-부톡사이드 (5.4 g, 56.1 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.6 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 10 9.3 g 을 얻었다. (수율 51%, MS: [M+H]+= 653)In a nitrogen atmosphere, sub 10 (10 g, 28 mmol), compound a (9.3 g, 28 mmol), sodium tert-butoxide (5.4 g, 56.1 mmol) was added to 200 mL of xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 10. (Yield 51%, MS: [M+H] + = 653)
합성예 11: 화합물 11의 제조Synthesis Example 11: Preparation of compound 11
질소 분위기에서 sub 11 (10 g, 27mmol), 화합물 a (8.9 g, 27 mmol), 소듐 tert-부톡사이드 (5.2 g, 53.9 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 11 6.6 g 을 얻었다. (수율 37%, MS: [M+H]+= 667)In a nitrogen atmosphere, sub 11 (10 g, 27 mmol), compound a (8.9 g, 27 mmol), sodium tert-butoxide (5.2 g, 53.9 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.6 g of compound 11. (Yield 37%, MS: [M+H] + = 667)
합성예 12: 화합물 12의 제조Synthesis Example 12: Preparation of Compound 12
질소 분위기에서 sub 12 (10 g, 25.8mmol), 화합물 a (8.6 g, 25.8 mmol), 소듐 tert-부톡사이드 (5 g, 51.7 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 12 5.6 g 을 얻었다. (수율 32%, MS: [M+H]+= 683)In a nitrogen atmosphere, sub 12 (10 g, 25.8 mmol), compound a (8.6 g, 25.8 mmol), and sodium tert-butoxide (5 g, 51.7 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.6 g of compound 12. (Yield 32%, MS: [M+H] + = 683)
합성예 13: 화합물 13의 제조Synthesis Example 13: Preparation of compound 13
질소 분위기에서 sub 13 (10 g, 31.6mmol), 화합물 a (10.5 g, 31.6 mmol), 소듐 tert-부톡사이드 (6.1 g, 63.1 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.6 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 13 9.8 g 을 얻었다. (수율 51%, MS: [M+H]+= 613)In a nitrogen atmosphere, sub 13 (10 g, 31.6 mmol), compound a (10.5 g, 31.6 mmol), sodium tert-butoxide (6.1 g, 63.1 mmol) was added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of compound 13. (Yield 51%, MS: [M+H] + = 613)
합성예 14: 화합물 14의 제조Synthesis Example 14: Preparation of Compound 14
질소 분위기에서 sub 14 (10 g, 24.6mmol), 화합물 a (8.2 g, 24.6 mmol), 소듐 tert-부톡사이드 (4.7 g, 49.3 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 3시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 14 5.2 g 을 얻었다. (수율 30%, MS: [M+H]+= 702)In a nitrogen atmosphere, sub 14 (10 g, 24.6 mmol), compound a (8.2 g, 24.6 mmol), and sodium tert-butoxide (4.7 g, 49.3 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.2 g of compound 14. (Yield 30%, MS: [M+H] + = 702)
합성예 15: 화합물 15의 제조Synthesis Example 15: Preparation of compound 15
질소 분위기에서 sub 15 (10 g, 26.3mmol), 화합물 a (8.7 g, 26.3 mmol), 소듐 tert-부톡사이드 (5 g, 52.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 15 5.9 g 을 얻었다. (수율 33%, MS: [M+H]+= 677)In a nitrogen atmosphere, sub 15 (10 g, 26.3 mmol), compound a (8.7 g, 26.3 mmol), sodium tert-butoxide (5 g, 52.5 mmol) was added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.9 g of compound 15. (Yield 33%, MS: [M+H] + = 677)
합성예 16: 화합물 16의 제조Synthesis Example 16: Preparation of Compound 16
질소 분위기에서 sub 16 (10 g, 26.3mmol), 화합물 b (9.1 g, 26.3 mmol), 소듐 tert-부톡사이드 (5 g, 52.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 16 9.2 g 을 얻었다. (수율 48%, MS: [M+H]+= 732)In a nitrogen atmosphere, sub 16 (10 g, 26.3 mmol), compound b (9.1 g, 26.3 mmol), and sodium tert-butoxide (5 g, 52.5 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of compound 16. (Yield 48%, MS: [M+H] + = 732)
합성예 17: 화합물 17의 제조Synthesis Example 17: Preparation of compound 17
질소 분위기에서 sub 17 (10 g, 25.4mmol), 화합물 b (8.8 g, 25.4 mmol), 소듐 tert-부톡사이드 (4.9 g, 50.8 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 3시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 17 5.9 g 을 얻었다. (수율 33%, MS: [M+H]+= 706)In a nitrogen atmosphere, sub 17 (10 g, 25.4 mmol), compound b (8.8 g, 25.4 mmol), and sodium tert-butoxide (4.9 g, 50.8 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.9 g of compound 17. (Yield 33%, MS: [M+H] + = 706)
합성예 18: 화합물 18의 제조Synthesis Example 18: Preparation of Compound 18
질소 분위기에서 sub 18 (10 g, 22.2mmol), 화합물 b (7.7 g, 22.2 mmol), 소듐 tert-부톡사이드 (4.3 g, 44.4 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.4 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 18 9.6 g 을 얻었다. (수율 57%, MS: [M+H]+= 762)In a nitrogen atmosphere, sub 18 (10 g, 22.2 mmol), compound b (7.7 g, 22.2 mmol), and sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6 g of compound 18. (Yield 57%, MS: [M+H] + = 762)
합성예 19: 화합물 19의 제조Synthesis Example 19: Preparation of compound 19
질소 분위기에서 sub 19 (10 g, 23.1mmol), 화합물 b (8 g, 23.1 mmol), 소듐 tert-부톡사이드 (4.4 g, 46.2 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 19 7.9 g 을 얻었다. (수율 46%, MS: [M+H]+= 745)In a nitrogen atmosphere, sub 19 (10 g, 23.1 mmol), compound b (8 g, 23.1 mmol), and sodium tert-butoxide (4.4 g, 46.2 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 19. (Yield 46%, MS: [M+H] + = 745)
합성예 20: 화합물 20의 제조Synthesis Example 20: Preparation of Compound 20
질소 분위기에서 sub 20 (10 g, 28.8mmol), 화합물 b (10 g, 28.8 mmol), 소듐 tert-부톡사이드 (5.5 g, 57.7 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.6 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 20 8.3 g 을 얻었다. (수율 44%, MS: [M+H]+= 659)In a nitrogen atmosphere, sub 20 (10 g, 28.8 mmol), compound b (10 g, 28.8 mmol), and sodium tert-butoxide (5.5 g, 57.7 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.3 g of compound 20. (Yield 44%, MS: [M+H] + = 659)
합성예 21: 화합물 21의 제조Synthesis Example 21: Preparation of Compound 21
질소 분위기에서 sub 21 (10 g, 23.6mmol), 화합물 b (8.2 g, 23.6 mmol), 소듐 tert-부톡사이드 (4.5 g, 47.3 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물21 9.4 g 을 얻었다. (수율 54%, MS: [M+H]+= 735)In a nitrogen atmosphere, sub 21 (10 g, 23.6 mmol), compound b (8.2 g, 23.6 mmol), and sodium tert-butoxide (4.5 g, 47.3 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 21. (Yield 54%, MS: [M+H] + = 735)
합성예 22: 화합물 22의 제조Synthesis Example 22: Preparation of Compound 22
질소 분위기에서 sub 22 (10 g, 25.8mmol), 화합물 b (9 g, 25.8 mmol), 소듐 tert-부톡사이드 (5 g, 51.7 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 22 8.8 g 을 얻었다. (수율 49%, MS: [M+H]+= 699)In a nitrogen atmosphere, sub 22 (10 g, 25.8 mmol), compound b (9 g, 25.8 mmol), and sodium tert-butoxide (5 g, 51.7 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of compound 22. (Yield 49%, MS: [M+H] + = 699)
합성예 23: 화합물 23의 제조Synthesis Example 23: Preparation of Compound 23
질소 분위기에서 sub 23 (10 g, 25.9mmol), 화합물 b (9 g, 25.9 mmol), 소듐 tert-부톡사이드 (5 g, 51.8 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 23 8.8 g 을 얻었다. (수율 49%, MS: [M+H]+= 698)In a nitrogen atmosphere, sub 23 (10 g, 25.9 mmol), compound b (9 g, 25.9 mmol), sodium tert-butoxide (5 g, 51.8 mmol) was added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of compound 23. (Yield 49%, MS: [M+H] + = 698)
합성예 24: 화합물 24의 제조Synthesis Example 24: Preparation of Compound 24
질소 분위기에서 sub 24 (10 g, 30.2mmol), 화합물 b (10.5 g, 30.2 mmol), 소듐 tert-부톡사이드 (5.8 g, 60.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.6 mmol)을 투입하였다. 3시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 24 11.4 g 을 얻었다. (수율 59%, MS: [M+H]+= 643)In a nitrogen atmosphere, sub 24 (10 g, 30.2 mmol), compound b (10.5 g, 30.2 mmol), and sodium tert-butoxide (5.8 g, 60.5 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 24. (Yield 59%, MS: [M+H] + = 643)
합성예 25: 화합물 25의 제조Synthesis Example 25: Preparation of compound 25
질소 분위기에서 sub 25 (10 g, 23.1mmol), 화합물 b (8 g, 23.1 mmol), 소듐 tert-부톡사이드 (4.4 g, 46.2 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.2 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 25 8.6 g 을 얻었다. (수율 50%, MS: [M+H]+= 745)In a nitrogen atmosphere, sub 25 (10 g, 23.1 mmol), compound b (8 g, 23.1 mmol), and sodium tert-butoxide (4.4 g, 46.2 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound 25. (Yield 50%, MS: [M+H] + = 745)
합성예 26: 화합물 26의 제조Synthesis Example 26: Preparation of Compound 26
질소 분위기에서 sub 26 (10 g, 35.6mmol), 화합물 b (12.4 g, 35.6 mmol), 소듐 tert-부톡사이드 (6.8 g, 71.2 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.4 g, 0.7 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 26 9.9 g 을 얻었다. (수율 47%, MS: [M+H]+= 593)In a nitrogen atmosphere, sub 26 (10 g, 35.6 mmol), compound b (12.4 g, 35.6 mmol), and sodium tert-butoxide (6.8 g, 71.2 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of compound 26. (Yield 47%, MS: [M+H] + = 593)
합성예Synthesis example 27: 화합물 27의 제조 27: Preparation of compound 27
질소 분위기에서 sub 27 (10 g, 25.8mmol), 화합물 b (9 g, 25.8 mmol), 소듐 tert-부톡사이드 (5 g, 51.7 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 27 7.8 g 을 얻었다. (수율 43%, MS: [M+H]+= 699)In a nitrogen atmosphere, sub 27 (10 g, 25.8 mmol), compound b (9 g, 25.8 mmol), and sodium tert-butoxide (5 g, 51.7 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 27. (Yield 43%, MS: [M+H] + = 699)
합성예 28: 화합물 28의 제조Synthesis Example 28: Preparation of compound 28
질소 분위기에서 sub 28 (10 g, 26.3mmol), 화합물 b (9.1 g, 26.3 mmol), 소듐 tert-부톡사이드 (5 g, 52.5 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 28 9.4 g 을 얻었다. (수율 52%, MS: [M+H]+= 693)In a nitrogen atmosphere, sub 28 (10 g, 26.3 mmol), compound b (9.1 g, 26.3 mmol), and sodium tert-butoxide (5 g, 52.5 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 28. (Yield 52%, MS: [M+H] + = 693)
합성예Synthesis example 29: 화합물 29의 제조 29: Preparation of compound 29
질소 분위기에서 sub 29 (10 g, 25.2mmol), 화합물 b (8.8 g, 25.2 mmol), 소듐 tert-부톡사이드 (4.8 g, 50.4 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 2시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 29 8.7 g 을 얻었다. (수율 49%, MS: [M+H]+= 709)In a nitrogen atmosphere, sub 29 (10 g, 25.2 mmol), compound b (8.8 g, 25.2 mmol), and sodium tert-butoxide (4.8 g, 50.4 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 29. (Yield 49%, MS: [M+H] + = 709)
합성예 30: 화합물 30의 제조Synthesis Example 30: Preparation of Compound 30
질소 분위기에서 sub 30 (10 g, 25.2mmol), 화합물 b (8.8 g, 25.2 mmol), 소듐 tert-부톡사이드 (4.8 g, 50.4 mmol) 을 자일렌 200 mL에 넣고 교반 및 환류하였다. 이 후 비스(트리-tert-부틸포스핀)팔라듐(0) (0.3 g, 0.5 mmol)을 투입하였다. 4시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거하였다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물30 10 g 을 얻었다. (수율 56%, MS: [M+H]+= 709)In a nitrogen atmosphere, sub 30 (10 g, 25.2 mmol), compound b (8.8 g, 25.2 mmol), and sodium tert-butoxide (4.8 g, 50.4 mmol) were added to 200 mL of xylene, followed by stirring and refluxing. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 30. (Yield 56%, MS: [M+H] + = 709)
비교예 1: 유기 발광 소자의 제조Comparative Example 1: Fabrication 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 사용했다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행했다. 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) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 하기 HI-1 화합물을 1150Å의 두께로 형성하되 하기 A-1 화합물을 1.5% 농도로 p-doping 하였다. 상기 정공주입층 위에 하기 HT-1 화합물을 진공 증착하여 막 두께 800Å 의 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 150Å으로 하기 EB-1 화합물을 진공 증착하여 전자억제층을 형성하였다. The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150Å, but the following compound A-1 was p-doping at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, an electron suppressing layer was formed by vacuum depositing the following EB-1 compound having a thickness of 150 Å on the hole transport layer.
이어서, 상기 EB-1 증착막 위에 호스트 물질로 하기 RH-1 화합물과 도펀트 물질로 하기 Dp-7 화합물을 98:2의 중량비로 진공 증착하여 400Å 두께의 적색 발광층을 형성하였다. Subsequently, the following RH-1 compound as a host material and the following Dp-7 compound as a dopant material were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition layer to form a red light emitting layer having a thickness of 400 Å.
상기 발광층 위에 막 두께 30Å으로 하기 HB-1 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 ET-1 화합물과 하기 LiQ 화합물을 2:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. A hole blocking layer was formed by vacuum depositing the following HB-1 compound with a thickness of 30 Å on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å.
상기 전자 주입 및 수송층 위에 순차적으로 12Å 두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
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 제작했다.In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å/sec, lithium fluoride at the cathode was maintained at 0.3 Å/sec, and the deposition rate for aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10 -7 ~ An organic light-emitting device was fabricated by maintaining 5x10 -6 torr.
실시예 1 내지 실시예 30Examples 1 to 30
비교예 1의 유기 발광 소자에서 발광층의 호스트 물질로 RH-1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. In the organic light-emitting device of Comparative Example 1, an organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of RH-1 as the host material of the emission layer.
비교예 2 내지 비교예 9Comparative Examples 2 to 9
비교예 1의 유기 발광 소자에서 발광층의 호스트 물질로 RH-1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 이때, 비교예에 사용된 화합물 C-1 내지 C-8의 구조는 하기와 같다.In the organic light-emitting device of Comparative Example 1, an organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of RH-1 as the host material of the emission layer. At this time, the structures of compounds C-1 to C-8 used in Comparative Examples are as follows.
실험예 1: 소자 특성 평가Experimental Example 1: Evaluation of device characteristics
상기 실시예 1 내지 실시예 30 및 비교예 1 내지 비교예 9에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율을 측정(10 mA/cm2)하고 그 결과를 하기 표1애 나타내었다. 이때, 수명 T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current was applied to the organic light emitting devices prepared in Examples 1 to 30 and Comparative Examples 1 to 9, voltage and efficiency were measured (10 mA/cm 2 ), and the results are shown in Table 1 below. Done. At this time, the lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
(V)Driving voltage
(V)
(cd/A)efficiency
(cd/A)
(hr)Life T95
(hr)
상기 표에 나타난 바와 같이, 적색 발광층의 호스트 물질로 상기 화학식 1로 표시되는 화합물을 사용한 실시예의 유기 발광 소자는, 비교예의 유기 발광 소자에 비하여, 구동 전압이 낮으면서, 효율이 높고 현저히 긴 수명을 나타내었다. 이는, 상기 화학식 1로 표시되는 화합물이 비교예에 사용된 본원과 상이한 구조를 갖는 화합물에 비하여, 적색 도펀트로의 에너지 전달이 잘 이루어졌기 때문인 것으로 판단된다. 또한, 비교예의 소자에 비해 실시예의 소자가 효율 및 수명이 동시에 향상된 것으로 보아, 상기 화학식 1로 표시되는 화합물은 전자와 정공에 대한 안정도가 높음을 알 수 있다. 따라서, 유기 발광 소자의 호스트 물질로 상기 화학식 1로 표시되는 화합물을 채용하는 경우, 유기 발광 소자의 구동 전압, 발광 효율 및/또는 수명 특성이 향상됨을 확인할 수 있다.As shown in the table above, the organic light-emitting device of the Example using the compound represented by
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공주입층
6: 정공수송층
7: 전자억제층
8: 정공저지층
9: 전자 주입 및 수송층1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: hole blocking layer
9: electron injection and transport layer
Claims (8)
[화학식 1]
상기 화학식 1에서,
X는 O 또는 S이고,
L은 단일결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고,
Ar은 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
R1 내지 R4는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
a는 0 내지 3의 정수이고,
b는 0 내지 4의 정수이고,
c는 0 내지 3의 정수이고,
d는 0 내지 2의 정수이다.
Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
X is O or S,
L is a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms of N, O and S,
Ar is a substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms of N, O and S,
R 1 to R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
a is an integer from 0 to 3,
b is an integer from 0 to 4,
c is an integer from 0 to 3,
d is an integer from 0 to 2.
L은 단일결합, 페닐렌, 또는 나프틸렌인,
화합물.
The method of claim 1,
L is a single bond, phenylene, or naphthylene,
compound.
Ar은 하기 화학식 2A 내지 2D로 표시되는 치환기 중 어느 하나인,
화합물:
상기 화학식 2A 내지 2D에서,
Y는 O 또는 S이고,
Q 중 하나는 상기 화학식 1의 L과 결합되는 C이고, 나머지는 각각 독립적으로, N 또는 CR이고, 단, 나머지 중 적어도 하나는 N이고,
R, R' 및 R"는 각각 독립적으로, 수소, 중수소, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,
여기서, 상기 R, R' 및 R"는 비치환되거나, 또는 중수소, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되고,
m은 0 내지 4의 정수이고,
n은 0 내지 6의 정수이다.
The method of claim 1,
Ar is any one of the substituents represented by the following formulas 2A to 2D,
compound:
In Formulas 2A to 2D,
Y is O or S,
One of Q is C bonded to L in Formula 1, and the others are each independently N or CR, provided that at least one of the others is N,
R, R'and R" are each independently hydrogen, deuterium, C 6-20 aryl; Or C 2-20 heteroaryl comprising one or more heteroatoms of N, O and S,
Here, the R, R'and R" are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl,
m is an integer from 0 to 4,
n is an integer from 0 to 6.
R 및 R'는 각각 독립적으로, 페닐, 나프틸페닐, 비페닐릴, 터페닐릴, 나프틸, 페닐나프틸, 페난쓰레닐, 9,9-디메틸플루오레닐, 카바졸일, 9-페닐카바졸일, 디벤조퓨라닐, 또는 디벤조티오페닐이고,
R"는 수소, 또는 중수소인,
화합물.
The method of claim 3,
R and R'are each independently, phenyl, naphthylphenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, phenanthrenyl, 9,9-dimethylfluorenyl, carbazolyl, 9-phenylcarba Zolyl, dibenzofuranyl, or dibenzothiophenyl,
R" is hydrogen or deuterium,
compound.
R1 내지 R4는 각각 독립적으로, 수소, 또는 중수소인,
화합물.
The method of claim 1,
R 1 to R 4 are each independently hydrogen or deuterium,
compound.
상기 화합물은 하기 화학식 3a, 3b-1, 3b-2, 3c-1 내지 3c-4 및 3d-1 내지 3d-4 중 어느 하나로 표시되는,
화합물:
상기 화학식 3a, 3b-1, 3b-2, 3c-1 내지 3c-4 및 3d-1 내지 3d-4 에서,
Y는 O 또는 S이고,
Z는 각각 독립적으로, N 또는 CH이고, 단, Z 중 적어도 하나는 N이고,
R 및 R'는 각각 독립적으로, C6-20 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,
여기서, 상기 R 및 R'는 비치환되거나, 또는 중수소, C1-10 알킬 및 C6-20 아릴로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되고,
X 및 L은 제1항에서 정의한 바와 같다.
The method of claim 1,
The compound is represented by any one of the following formulas 3a, 3b-1, 3b-2, 3c-1 to 3c-4, and 3d-1 to 3d-4,
compound:
In Formulas 3a, 3b-1, 3b-2, 3c-1 to 3c-4, and 3d-1 to 3d-4,
Y is O or S,
Z is each independently N or CH, provided that at least one of Z is N,
R and R'are each independently C 6-20 aryl; Or C 2-20 heteroaryl containing one or more heteroatoms of N, O and S,
Wherein R and R'are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl,
X and L are as defined in claim 1.
상기 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
.
The method of claim 1,
The compound is any one selected from the group consisting of the following compounds,
compound:
.
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CN107880056A (en) * | 2016-09-30 | 2018-04-06 | 南京高光半导体材料有限公司 | Organic electroluminescent compounds and the organic electroluminescence device using the compound |
KR20180099547A (en) * | 2017-02-28 | 2018-09-05 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent device |
KR20200103524A (en) * | 2019-02-25 | 2020-09-02 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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