KR102406563B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents
Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof Download PDFInfo
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- KR102406563B1 KR102406563B1 KR1020210004208A KR20210004208A KR102406563B1 KR 102406563 B1 KR102406563 B1 KR 102406563B1 KR 1020210004208 A KR1020210004208 A KR 1020210004208A KR 20210004208 A KR20210004208 A KR 20210004208A KR 102406563 B1 KR102406563 B1 KR 102406563B1
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- South Korea
- Prior art keywords
- organic
- layer
- group
- compound
- light emitting
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 239000000463 material Substances 0.000 claims description 56
- 230000005525 hole transport Effects 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 239000011368 organic material Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 238000003618 dip coating Methods 0.000 claims description 3
- 238000007641 inkjet printing Methods 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 201
- 230000000052 comparative effect Effects 0.000 description 96
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000002347 injection Methods 0.000 description 31
- 239000007924 injection Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 22
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- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229960001866 silicon dioxide Drugs 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- OLLJKISFWSJGID-UHFFFAOYSA-N 4-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C=2C(Br)=CC=CC=2N1C1=CC=CC=C1 OLLJKISFWSJGID-UHFFFAOYSA-N 0.000 description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 5
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- 229910052736 halogen Inorganic materials 0.000 description 5
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
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- SOODLDGRGXOSTA-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 SOODLDGRGXOSTA-UHFFFAOYSA-N 0.000 description 3
- WUXIRZBTTICLCG-UHFFFAOYSA-N 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=C1 WUXIRZBTTICLCG-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
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- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
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- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 2
- GTJFRSVWOUWTDJ-UHFFFAOYSA-N 4-bromo-2-nitro-1-phenylbenzene Chemical group [O-][N+](=O)C1=CC(Br)=CC=C1C1=CC=CC=C1 GTJFRSVWOUWTDJ-UHFFFAOYSA-N 0.000 description 2
- CBJHFGQCHKNNJY-UHFFFAOYSA-N 4-bromo-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2Br CBJHFGQCHKNNJY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYXFUZQLJCJCIC-UHFFFAOYSA-N BrC1=C(C(=CC=C1)[N+](=O)[O-])C1CC=CC=C1 Chemical group BrC1=C(C(=CC=C1)[N+](=O)[O-])C1CC=CC=C1 OYXFUZQLJCJCIC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000005567 fluorenylene group Chemical group 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- BJOZUBWLKNXFFK-UHFFFAOYSA-N 1-bromo-2-iodo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1I BJOZUBWLKNXFFK-UHFFFAOYSA-N 0.000 description 1
- OYSGKCMNNSUNCD-UHFFFAOYSA-N 11-(4-phenylquinazolin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[a]carbazole Chemical compound CC1(C)OB(OC1(C)C)C1=C2C(=CC=C1)N(C1=C2C=CC2=CC=CC=C12)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1 OYSGKCMNNSUNCD-UHFFFAOYSA-N 0.000 description 1
- GLYYLMBVQZMMMS-UHFFFAOYSA-N 12h-[1]benzothiolo[3,2-a]carbazole Chemical compound S1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 GLYYLMBVQZMMMS-UHFFFAOYSA-N 0.000 description 1
- QRQUUKAKCHENHO-UHFFFAOYSA-N 3-[3-(4-bromocarbazol-9-yl)phenyl]-N,N-diphenylaniline Chemical compound BrC1=CC=CC=2N(C3=CC=CC=C3C1=2)C=1C=C(C=CC=1)C1=CC(=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 QRQUUKAKCHENHO-UHFFFAOYSA-N 0.000 description 1
- XLUAZLDTZYHVSO-UHFFFAOYSA-N 4-bromo-1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1I XLUAZLDTZYHVSO-UHFFFAOYSA-N 0.000 description 1
- TZZWXCRSAXVRBE-UHFFFAOYSA-N 4-bromo-9-(4-phenylquinazolin-2-yl)carbazole Chemical compound BrC1=CC=CC2=C1C1=C(C=CC=C1)N2C1=NC2=C(C=CC=C2)C(=N1)C1=CC=CC=C1 TZZWXCRSAXVRBE-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- SQBFYYCRNFQSGC-UHFFFAOYSA-N 6h-thieno[3,2-c]carbazole Chemical compound C1=CC=C2C3=C(SC=C4)C4=CC=C3NC2=C1 SQBFYYCRNFQSGC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- CONCJLAGZOBHMC-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=C(C=C1)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N(C1=CC=C(C=C1)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 CONCJLAGZOBHMC-UHFFFAOYSA-N 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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Images
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Abstract
본 발명은 소자의 발광효율, 안정성 및 수명을 향상시킬 수 있는 신규 화합물 및 이를 이용한 유기전기소자, 그 전자 장치를 제공한다.The present invention provides a novel compound capable of improving the luminous efficiency, stability and lifespan of a device, an organic electric device using the same, and an electronic device thereof.
Description
본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다.A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.
유기 전기 발광소자에 있어 가장 문제시되는 것은 수명과 효율인데, 디스플레이가 대면적화되면서 이러한 효율이나 수명 문제는 반드시 해결해야되는 상황이다.Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.
효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동시 발생되는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.
하지만 상기 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면 각 유기물층 간의 에너지 준위 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다. However, the efficiency cannot be maximized by simply improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.
또한, 최근 유기 전기 발광소자에 있어 정공수송층에서의 발광 문제를 해결하기 위해서는 반드시 정공수송층과 발광층 사이에 발광보조층이 존재하여야 하며, 각각의 발광층(R, G, B)에 따른 서로 다른 발광 보조층의 개발이 필요한 시점이다. In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) supports different light emission. It is time for layer development.
일반적으로 전자수송층에서 발광층으로 전자(electron)가 전달되고 정공(hole)이 정공수송층에서 발광층으로 전달되어 재조합(recombination)에 의해 엑시톤(exciton)이 생성된다. In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.
하지만 정공수송층에 사용되는 물질의 경우 낮은 HOMO 값을 가져야 하기 때문에 대부분 낮은 T1 값을 가지며, 이로 인해 발광층에서 생성된 엑시톤(exciton)이 정공수송층으로 넘어가게 되어 결과적으로 발광층 내 전하 불균형(charge unbalance)을 초래하여 정공수송층 계면에서 발광하게 된다.However, most materials used for the hole transport layer have a low T1 value because they have to have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. This results in light emission at the hole transport layer interface.
정공수송층 계면에서 발광될 경우, 유기전기소자의 색순도 및 효율이 저하되고 수명이 짧아지는 문제점이 발생하게 된다. 따라서 높은 T1 값을 가지며, 정공 수송층 HOMO 에너지 준위와 발광층의 HOMO 에너지 준위 사이의 HOMO 준위를 갖는 발광보조층이 개발이 절실히 요구된다.When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it is urgently required to develop a light emitting auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.
한편, 유기전기소자의 수명단축 원인 중 하나인 양극전극(ITO)으로부터 금속 산화물이 유기층으로 침투확산되는 것을 지연시키면서, 소자 구동시 발생되는 주울열(Joule heating)에 대해서도 안정된 특성, 즉 높은 유리 전이 온도를 갖는 정공 주입층 재료에 대한 개발이 필요하다. 정공수송층 재료의 낮은 유리전이 온도는 소자 구동시, 박막 표면의 균일도를 저하시키는 특성이 있는바, 이는 소자수명에 큰 영향을 미치는 것으로 보고되고 있다. 또한, OLED 소자는 주로 증착 방법에 의해 형성되는데, 증착시 오랫동안 견딜 수 있는 재료, 즉 내열특성이 강한 재료 개발이 필요한 실정이다. On the other hand, while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of the organic electric device, stable characteristics against Joule heating generated during device driving, that is, high glass transition There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a characteristic of lowering the uniformity of the thin film surface when driving the device, which is reported to have a significant effect on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance.
즉, 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질, 발광보조층 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정되고 효율적인 유기전기소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 새로운 재료의 개발이 계속 요구되고 있으며, 특히 발광보조층과 정공수송층의 재료에 대한 개발이 절실히 요구되고 있다.That is, in order to sufficiently exhibit the excellent characteristics of an organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc. is stable and efficient. Supported by materials should be preceded, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently developed. Therefore, the development of new materials is continuously required, and in particular, the development of materials for the light emitting auxiliary layer and the hole transport layer is urgently required.
본 발명은 소자의 높은 발광효율, 낮은 구동전압, 고내열성, 색순도 및 수명을 향상시킬 수 있는 화합물, 이를 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다. An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity and lifespan of the device, an organic electric device using the same, and an electronic device thereof.
일 측면에서, 본 발명은 하기 화학식으로 표시되는 화합물을 제공한다.In one aspect, the present invention provides a compound represented by the following formula.
다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공한다.In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
본 발명에 따른 화합물을 이용함으로써 소자의 높은 발광효율, 낮은 구동전압, 고내열성을 달성할 수 있고, 소자의 색순도 및 수명을 크게 향상시킬 수 있다. By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be greatly improved.
도 1은 본 발명에 따른 유기전기발광소자의 예시도이다. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
이하, 본 발명의 실시예를 첨부된 도면을 참조하여 상세하게 설명한다.Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.
각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.
또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a),(b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is formed between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”
본 명세서 및 첨부된 청구의 범위에서 사용된 바와 같이, 달리 언급하지 않는 한, 하기 용어의 의미는 하기와 같다:As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings:
본 명세서에서 사용된 용어 "할로" 또는 "할로겐"은 다른 설명이 없는 한 불소(F), 브롬(Br), 염소(Cl) 또는 요오드(I)이다.As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.
본 발명에 사용된 용어 "알킬" 또는 "알킬기"는 다른 설명이 없는 한 1 내지 60의 탄소수의 단일결합을 가지며, 직쇄 알킬기, 분지쇄 알킬기, 사이클로알킬(지환족)기, 알킬-치환된 사이클로알킬기, 사이클로알킬-치환된 알킬기를 비롯한 포화 지방족 작용기의 라디칼을 의미한다.The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond of 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups and cycloalkyl-substituted alkyl groups.
본 발명에 사용된 용어 "할로알킬기" 또는 "할로겐알킬기"는 다른 설명이 없는 한 할로겐으로 치환된 알킬기를 의미한다.As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with halogen unless otherwise specified.
본 발명에 사용된 용어 "헤테로알킬기"는 알킬기를 구성하는 탄소 원자 중 하나 이상이 헤테로원자로 대체된 것을 의미한다.As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.
본 발명에 사용된 용어 "알켄일기" 또는 "알킨일기"는 다른 설명이 없는 한 각각 2 내지 60의 탄소수의 이중결합 또는 삼중결합을 가지며, 직쇄형 또는 측쇄형 사슬기를 포함하며, 여기에 제한되는 것은 아니다. The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not
본 발명에 사용된 용어 "시클로알킬"은 다른 설명이 없는 한 3 내지 60의 탄소수를 갖는 고리를 형성하는 알킬을 의미하며, 여기에 제한되는 것은 아니다. As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.
본 발명에 사용된 용어 "알콕실기", "알콕시기", 또는 "알킬옥시기"는 산소 라디칼이 부착된 알킬기를 의미하며, 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, and is limited thereto. it is not
본 발명에 사용된 용어 "알켄옥실기", "알켄옥시기", "알켄일옥실기", 또는 "알켄일옥시기"는 산소 라디칼이 부착된 알켄일기를 의미하며, 다른 설명이 없는 한 2 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" refer to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.
본 발명에 사용된 용어 "아릴옥실기" 또는 "아릴옥시기"는 산소 라디칼이 부착된 아릴기를 의미하며, 다른 설명이 없는 한 6 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. 본 발명에서 아릴기 또는 아릴렌기는 단일 고리 또는 다중 고리의 방향족을 의미하며, 이웃한 치환기가 결합 또는 반응에 참여하여 형성된 방향족 고리를 포함한다. 예컨대, 아릴기는 페닐기, 비페닐기, 플루오렌기, 스파이로플루오렌기일 수 있다. The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.
접두사 "아릴" 또는 "아르"는 아릴기로 치환된 라디칼을 의미한다. 예를 들어 아릴알킬기는 아릴기로 치환된 알킬기이며, 아릴알켄일기는 아릴기로 치환된 알켄일기이며, 아릴기로 치환된 라디칼은 본 명세서에서 설명한 탄소수를 가진다.The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the number of carbon atoms described herein.
또한 접두사가 연속으로 명명되는 경우 먼저 기재된 순서대로 치환기가 나열되는 것을 의미한다. 예를 들어, 아릴알콕시기의 경우 아릴기로 치환된 알콕시기를 의미하며, 알콕실카르보닐기의 경우 알콕실기로 치환된 카르보닐기를 의미하며, 또한 아릴카르보닐알켄일기의 경우 아릴카르보닐기로 치환된 알켄일기를 의미하며 여기서 아릴카르보닐기는 아릴기로 치환된 카르보닐기이다.Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group and wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.
본 명세서에서 사용된 용어 "헤테로알킬"은 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하는 알킬을 의미한다. 본 발명에 사용된 용어 "헤테로아릴기" 또는 "헤테로아릴렌기"는 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 아릴기 또는 아릴렌기를 의미하며, 여기에 제한되는 것은 아니며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 이웃한 작용기기가 결합하여 형성될 수도 있다.As used herein, the term “heteroalkyl” refers to an alkyl containing one or more heteroatoms, unless otherwise specified. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, No, it includes at least one of a single ring and a multiple ring, and may be formed by combining adjacent functional groups.
본 발명에 사용된 용어 "헤테로고리기"는 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하고, 2 내지 60의 탄소수를 가지며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 헤테로지방족 고리 및 헤테로방향족 고리를 포함한다. 이웃한 작용기가 결합하여 형성될 수도 있다. The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a hetero aromatic rings. It may be formed by combining adjacent functional groups.
본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타낸다. As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.
또한 "헤테로고리기"는, 고리를 형성하는 탄소 대신 SO2를 포함하는 고리도 포함할 수 있다. 예컨대, "헤테로고리기"는 다음 화합물을 포함한다. In addition, the "heterocyclic group" may include a ring containing SO 2 instead of carbon forming the ring. For example, "heterocyclic group" includes the following compounds.
다른 설명이 없는 한, 본 발명에 사용된 용어 "지방족"은 탄소수 1 내지 60의 지방족 탄화수소를 의미하며, "지방족고리"는 탄소수 3 내지 60의 지방족 탄화수소 고리를 의미한다. Unless otherwise specified, as used herein, the term "aliphatic" refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
다른 설명이 없는 한, 본 발명에 사용된 용어 "고리"는 탄소수 3 내지 60의 지방족고리 또는 탄소수 6 내지 60의 방향족고리 또는 탄소수 2 내지 60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화 고리를 포함한다.Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a combination thereof, saturated or unsaturated rings.
전술한 헤테로화합물 이외의 그 밖의 다른 헤테로화합물 또는 헤테로라디칼은 하나 이상의 헤테로원자를 포함하며, 여기에 제한되는 것은 아니다. Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.
다른 설명이 없는 한, 본 발명에 사용된 용어 "카르보닐"이란 -COR'로 표시되는 것이며, 여기서 R'은 수소, 탄소수 1 내지 20 의 알킬기, 탄소수 6 내지 30 의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것이다.Unless otherwise specified, the term "carbonyl" used in the present invention is represented by -COR', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. of a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
다른 설명이 없는 한, 본 발명에 사용된 용어 "에테르"란 -R-O-R'로 표시되는 것이며, 여기서 R 또는 R'은 각각 서로 독립적으로 수소, 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것이다.Unless otherwise specified, as used herein, the term "ether" is represented by -R-O-R', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 30 carbon atoms. An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
또한 명시적인 설명이 없는 한, 본 발명에서 사용된 용어 "치환 또는 비치환된"에서 "치환"은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C1~C20의 알콕실기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알켄일기, C2~C20의 알킨일기, C3~C20의 시클로알킬기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C8~C20의 아릴알켄일기, 실란기, 붕소기, 게르마늄기, 및 C2~C20의 헤테로고리기로 이루어진 군으로부터 선택되는 1개 이상의 치환기로 치환됨을 의미하며, 이들 치환기에 제한되는 것은 아니다. In addition, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in the present invention, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 1 ~ C 20 Alkoxyl group, C 1 ~ C 20 Alkylamine group, C 1 ~ C 20 Alkylthiophene group, C 6 ~ C 20 Arylthiophene group, C 2 ~ C 20 Alkenyl group, C 2 ~ C 20 alkynyl group, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 20 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 8 ~ C 20 arylalkenyl group, silane group, boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C 2 ~ C 20 heterocyclic group, but is not limited to these substituents.
또한 명시적인 설명이 없는 한, 본 발명에서 사용되는 화학식은 하기 화학식의 지수 정의에 의한 치환기 정의와 동일하게 적용된다.In addition, unless there is an explicit explanation, the formula used in the present invention applies the same as the definition of the substituent by the exponential definition of the following formula.
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하며, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 각각 다음과 같이 결합하며 이때 R1은 서로 동일하거나 다를 수 있으며, a가 4 내지 6의 정수인 경우 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, 한편 벤젠 고리를 형성하는 탄소에 결합된 수소의 표시는 생략한다.Here, when a is an integer of 0, the substituent R 1 is absent, and when a is an integer of 1, one substituent R 1 is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3 Each is bonded as follows, wherein R 1 may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is omitted.
도 1은 본 발명에 일 실시예에 따른 유기전기소자에 대한 예시도이다.1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(110)과 제 2전극(180) 사이에 본 발명에 따른 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.Referring to FIG. 1 , the organic
유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 발광층(150)을 제외한 나머지 층들이 형성되지 않을 수 있다. 정공저지층, 전자저지층, 발광보조층(151), 버퍼층(141) 등을 더 포함할 수도 있고, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있을 것이다. The organic material layer may sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . In this case, the remaining layers except for the emission layer 150 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151 , a buffer layer 141 , and the like, and the electron transport layer 160 and the like may serve as a hole blocking layer.
또한, 미도시하였지만, 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극 중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층 또는 광효율 개선층(Capping layer)을 더 포함할 수 있다. In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
상기 유기물층에 적용되는 본 발명에 따른 화합물은 정공주입층(130), 정공수송층(140), 전자수송층(160), 전자주입층(170), 발광층(150)의 호스트 또는 도펀트 또는 광효율 개선층의 재료로 사용될 수 있을 것이다. 바람직하게는, 본 발명의 화합물은 발광층(150), 정공수송층(140) 및/또는 발광보조층(151)으로 사용될 수 있을 것이다.The compound according to the present invention applied to the organic layer is a host or dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the light emitting layer 150, or the light efficiency improvement layer. material may be used. Preferably, the compound of the present invention may be used as the light emitting layer 150 , the hole transport layer 140 , and/or the light emission auxiliary layer 151 .
한편, 동일한 코어일지라도 어느 위치에 어느 치환기를 결합시키냐에 따라 밴드갭(band gap), 전기적 특성, 계면 특성 등이 달라질 수 있으므로, 코어의 선택 및 이에 결합된 서브(sub)-치환체의 조합도 아주 중요하며, 특히 각 유기물층 간의 에너지 준위 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있다.On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position of the substituent is bonded to the same core, so the selection of the core and the combination of the sub-substituents coupled thereto are also very In particular, when the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.
이미 설명한 것과 같이, 최근 유기 전기 발광소자에 있어 정공수송층에서의 발광 문제를 해결하기 위해서는 정공수송층과 발광층 사이에 발광보조층이 형성하는 것이 바람직하며, 각각의 발광층(R, G, B)에 따른 서로 다른 발광 보조층의 개발이 필요한 시점이다. 한편, 발광보조층의 경우 정공수송층 및 발광층(호스트)과의 상호관계를 파악해야하므로 유사한 코어를 사용하더라도 사용되는 유기물층이 달라지면 그 특징을 유추하기는 매우 어려울 것이다. As already described, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each light emitting layer (R, G, B) It is time to develop different light emitting auxiliary layers. On the other hand, in the case of the light emitting auxiliary layer, it is necessary to understand the relationship between the hole transport layer and the light emitting layer (host), so even if a similar core is used, it will be very difficult to infer its characteristics if the organic material layer used is different.
따라서, 본 발명에서는 화학식 1로 표시되는 화합물을 사용하여 발광층, 정공수송층 또는 발광보조층을 형성함으로써 각 유기물층 간의 에너지 레벨(level) 및 T1 값, 물질의 고유특성(mobility, 계면특성 등) 등을 최적화하여 유기전기소자의 수명 및 효율을 동시에 향상시킬 수 있다. Therefore, in the present invention, by forming a light emitting layer, a hole transport layer or a light emitting auxiliary layer using the compound represented by Formula 1, the energy level and T1 value between each organic material layer, the intrinsic properties of the material (mobility, interfacial properties, etc.), etc. By optimizing it, the lifespan and efficiency of the organic electric device can be improved at the same time.
본 발명의 일 실시예에 따른 유기전기발광소자는 PVD(physical vapor deposition) 방법을 이용하여 제조될 수 있다. 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(120)을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극(180)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, the anode 120 is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer ( 160) and an organic material layer including the electron injection layer 170 is formed, and then a material usable as the cathode 180 is deposited thereon.
또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정, 롤투롤 공정, 닥터 블레이딩 공정, 스크린 프린팅 공정, 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
본 발명에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric device according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
WOLED(White Organic Light Emitting Device)는 고해상도 실현이 용이하고 공정성이 우수한 한편, 기존의 LCD의 칼라필터 기술을 이용하여 제조될 수 있는 이점이 있다. 주로 백라이트 장치로 사용되는 백색 유기발광소자에 대한 다양한 구조들이 제안되고 특허화되고 있다. 대표적으로, R(Red), G(Green), B(Blue) 발광부들을 상호평면적으로 병렬배치(side-by-side) 방식, R, G, B 발광층이 상하로 적층되는 적층(stacking) 방식이 있고, 청색(B) 유기발광층에 의한 전계발광과 이로부터의 광을 이용하여 무기형광체의 자발광(photo-luminescence)을 이용하는 색변환물질(color conversion material, CCM) 방식 등이 있는데, 본 발명은 이러한 WOLED에도 적용될 수 있을 것이다.WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent in processability, and can be manufactured using the existing color filter technology of LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting units are mutually planar, and a stacking method in which R, G, and B light emitting layers are stacked up and down There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using the light therefrom. could also be applied to such WOLEDs.
또한, 본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 중 하나일 수 있다.In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and a single color or white lighting device.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.
이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, the compound according to one aspect of the present invention will be described.
본 발명의 일측면에 따른 화합물은 하기 화학식 1로 표시된다.The compound according to one aspect of the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
상기 화학식 1에서,In Formula 1,
Ar1 및 Ar2는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are each independently a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 A fused ring group of an aliphatic ring and a C 6 ~ C 60 aromatic ring; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; C 1 ~ C 30 An alkoxyl group; C 6 ~ C 30 Aryloxy group; and -L'-N(R a )(R b );
R1 내지 R14는 ⅰ) 서로 독립적으로 수소; 중수소; 할로겐; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의ⅰ 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되거나, 또는 ⅱ) 이웃하는 기끼리 서로 결합하여 고리를 형성할 수 있다. 한편, 이웃하는 기끼리 서로 결합하여 고리를 형성하는 것은 R1과 R2, R2와 R3, R3과 R4, R5와 R6, R6과 R7, R7과 R8, R9와 R10, R10과 R11 및 R13과 R14가 서로 결합하여 고리를 형성하는 것을 의미하며, 상기 고리는 C3~C60의 지방족고리, C6~C60의 방향족고리, C2~C60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화 고리를 포함한다.R 1 to R 14 are i) independently of each other hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 A fused ring group of i aliphatic ring and C 6 ~ C 60 aromatic ring; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; C 1 ~ C 30 An alkoxyl group; C 6 ~ C 30 Aryloxy group; and -L′-N(R a )(R b ); or ii) adjacent groups may be bonded to each other to form a ring. On the other hand, neighboring groups are bonded to each other to form a ring, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 and R 13 and R 14 are bonded to each other to form a ring, wherein the ring is a C 3 ~ C 60 aliphatic ring, a C 6 ~ C 60 aromatic ring, C 2 ~ C 60 Refers to a fused ring consisting of a heterocycle or a combination thereof, including a saturated or unsaturated ring.
상기 L'은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; 및 C2~C60의 헤테로고리기;로 이루어진 군에서 선택되며,The L' are each independently a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; C 3 ~ C 60 A fused ring group of an aliphatic ring and a C 6 ~ C 60 aromatic ring; And C 2 ~ C 60 A heterocyclic group; is selected from the group consisting of,
상기 Ra 및 Rb은 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;로 이루어진 군에서 선택된다.The R a and R b are each independently a C 6 ~ C 60 aryl group; fluorenyl group; C 3 ~ C 60 A fused ring group of an aliphatic ring and a C 6 ~ C 60 aromatic ring; And O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; is selected from the group consisting of.
여기서 상기 아릴기, 플루오렌일기, 헤테로고리기, 융합고리기, 알킬기, 알켄일기, 알킨일기, 알콕실기, 아릴옥시기, 아릴렌기, 플루오렌일렌기는 각각 중수소; 할로겐; 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; -L'-N(Ra)(Rb); C1~C20의 알킬싸이오기; C1~C20의 알콕실기; C1~C20의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C6~C20의 아릴기; 중수소로 치환된 C6~C20의 아릴기; 플루오렌일기; C2~C20의 헤테로고리기; C3~C20의 시클로알킬기; C7~C20의 아릴알킬기 및 C8~C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더욱 치환될 수 있으며, 또한 이들 치환기들은 서로 결합하여 고리를 형성할 수도 있으며, 상기 고리는 C3~C60의 지방족고리, C6~C60의 방향족고리, C2~C60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화 고리를 포함한다.다.wherein the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, and fluorenylene group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -L'-N(R a )(R b ); C 1 ~ C 20 Alkylthio group; C 1 ~ C 20 An alkoxyl group; C 1 ~ C 20 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; of C 6 to C 20 aryl group; C 6 ~ C 20 Aryl group substituted with deuterium; fluorenyl group; C 2 ~ C 20 A heterocyclic group; C 3 ~ C 20 Cycloalkyl group; It may be further substituted with one or more substituents selected from the group consisting of a C 7 ~ C 20 arylalkyl group and a C 8 ~ C 20 arylalkenyl group, and these substituents may be combined with each other to form a ring, wherein the ring is C 3 ~ C 60 aliphatic ring, C 6 ~ C 60 aromatic ring, C 2 ~ C 60 It refers to a fused ring consisting of a heterocycle or a combination thereof, including a saturated or unsaturated ring.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 화학식 4로 표시될 수 있다.Specifically, the compound represented by Formula 1 may be represented by Formulas 2 to 4 below.
<화학식 2> <화학식 3><Formula 2> <Formula 3>
<화학식 4><Formula 4>
상기 화학식 2 내지 4에서,In Formulas 2 to 4,
R1 내지 R14, L', Ra 및 Rb는 상기 화학식 1의 정의와 동일하며,R 1 to R 14 , L′, R a and R b are the same as defined in Formula 1 above,
Ar3 내지 Ar5는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기;로 이루어진 군에서 선택된다.Ar 3 To Ar 5 Are each independently a C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 A fused ring group of an aliphatic ring and a C 6 ~ C 60 aromatic ring; C 1 ~ C 50 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; C 1 ~ C 30 An alkoxyl group; And C 6 ~ C 30 Aryloxy group; is selected from the group consisting of.
보다 구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중 어느 하나일 수 있다.More specifically, the compound represented by Formula 1 may be any one of the following compounds.
본 발명의 또 다른 구체 예에서, 본 발명은 제 1전극; 제 2전극; 및 상기 제 1전극과 제 2전극 사이에 위치하는 유기물층;을 포함하는 유기전기소자에 있어서, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 유기전기소자를 제공한다. 구체적으로, 본 발명은 상기 유기물층에 상기 화학식 2 내지 화학식 4로 표시되는 화합물 중 하나를 포함하는 유기전기소자를 제공한다. 더욱 구체적으로, 본 발명은 상기 유기물층에 상기 개별 화학식으로 표시되는 화합물을 포함하는 유기전기소자를 제공한다.In another embodiment of the present invention, the present invention provides a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer provides an organic electric device including the compound represented by Formula 1 above. Specifically, the present invention provides an organic electric device including one of the compounds represented by Chemical Formulas 2 to 4 in the organic material layer. More specifically, the present invention provides an organic electric device including the compound represented by the individual formula in the organic material layer.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 유기물층에 적어도 정공수송층을 포함하며, 상기 정공수송층은 상기 화합물을 포함하는 것을 특징으로 하는 유기전기소자를 제공한다..In another embodiment of the present invention, the present invention provides an organic electric device comprising at least a hole transport layer in the organic material layer, wherein the hole transport layer includes the compound.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 유기물층에 적어도 발광보조층을 포함하며, 상기 발광보조층은 상기 화합물을 포함하는 것을 특징으로 하는 유기전기소자를 제공한다.In another embodiment of the present invention, the present invention provides an organic electric device comprising at least a light emission auxiliary layer on the organic material layer, and the light emission auxiliary layer includes the compound.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 유기물층에 적어도 발광층을 포함하며, 상기 화합물은 상기 발광층의 호스트 물질로 사용되는 것을 특징으로 하는 유기전기소자를 제공한다.In another embodiment of the present invention, the present invention provides an organic electric device comprising at least a light emitting layer in the organic material layer, and the compound is used as a host material for the light emitting layer.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 제 1전극의 일측면 중 상기 유기물층과 반대되는 일측 또는 상기 제 2전극의 일측면 중 상기 유기물층과 반대되는 일측 중 적어도 하나에 형성되는 광효율 개선층을 더 포함하는 유기전기소자를 제공한다.In another embodiment of the present invention, the present invention provides a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device further comprising a.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 유기물층이 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정 및 롤투롤 공정 중 어느 하나에 의해 형성되는 유기전기소자를 제공한다.In another embodiment of the present invention, the present invention provides an organic electric device in which the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process do.
본 발명의 또 다른 구체 예에서, 본 발명은 상기 유기물층을 포함하는 유기전기소자를 포함하는 디스플레이장치; 및 상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치를 제공한다.In another embodiment of the present invention, the present invention is a display device comprising an organic electric device including the organic material layer; and a controller for driving the display device.
본 발명의 또 다른 구체 예에서, 본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 및 단색 또는 백색 조명용 소자 중 적어도 하나일 수 있다.In another embodiment of the present invention, the organic electric device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organophotoreceptor (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting. can be one
이하에서, 본 발명에 따른 화학식 1로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, examples of the synthesis of the compound represented by Formula 1 and the preparation of an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.
합성예Synthesis example
본 발명에 따른 화학식 1로 표시되는 화합물(Product)은 하기 반응식 1과 같이 Sub 1과 Sub 2를 반응시켜 제조되며, 이에 한정되는 것은 아니다.The compound (Product) represented by Formula 1 according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.
<반응식 1><Scheme 1>
Ⅰ. 중간체의 합성I. synthesis of intermediates
1. One. SubSub 1의 합성 1 synthesis
상기 반응식 1의 Sub 1은 하기 반응식 2의 반응경로에 의해 합성될 수 있으며, 이에 한정된 것은 아니다.Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
<반응식 2><Scheme 2>
(1) (One) SubSub 1-3 합성 1-3 synthesis
2L 둥근바닥플라스크에 phenylboronic acid (628mmol), THF (700mL), H2O (350mL)을 넣고 녹인 후에 4-bromo-1-iodo-2-nitrobenzene (690mmol), NaOH (1035mmol), Pd(PPh3)4 (17.3mmol)을 순서대로 넣고 80℃에서 24시간 동안 반응을 진행한다. 반응이 완료되면 메틸렌클로라이드와 물, brine을 이용하여 추출하고 MgSO4로 유기층을 건조한다. 얻어진 유기층을 silicagel column (메틸렌클로라이드 : 헥산 = 1 : 3)하여 4-bromo-2-nitro-1,1'-biphenyl을 얻었다. In a 2L round-bottom flask, phenylboronic acid (628mmol), THF (700mL), H 2 O (350mL) were added and dissolved, followed by 4-bromo-1-iodo-2-nitrobenzene (690mmol), NaOH (1035mmol), Pd(PPh 3 ) 4 (17.3 mmol) is added in order, and the reaction proceeds at 80° C. for 24 hours. When the reaction is complete, extraction is performed using methylene chloride, water, and brine, and the organic layer is dried with MgSO 4 . The obtained organic layer was subjected to silicagel column (methylene chloride: hexane = 1: 3) to obtain 4-bromo-2-nitro-1,1'-biphenyl.
(2) (2) SubSub 1-4 합성 1-4 synthesis
4-bromo-2-nitro-1,1'-biphenyl에 triethylphosphate를 넣고 160℃ ~ 165℃ 상태에서 14시간 동안 가열 환류시킨다. 반응이 완료되면 감압증류로 남은 triethylphosphite를 제거하고, MeOH : H2O = 1:1 혼합용매로 희석시킨 후 생성된 고체를 여과한다. 얻어진 고체를 MeOH : H2O = 1:1 혼합용매와 petroleum ether로 씻어준다. 상기 고체를 메틸렌클로라이드에 녹인 후에 MgSO4로 건조하여 농축하고 silicagel column하여 2-bromo-9H-carbazole을 얻는다(petroleum ether : methylene chloride = 2:1).Add triethylphosphate to 4-bromo-2-nitro-1,1'-biphenyl and heat to reflux at 160°C to 165°C for 14 hours. When the reaction is complete, the remaining triethylphosphite is removed by distillation under reduced pressure, diluted with MeOH:H 2 O = 1:1 mixed solvent, and the resulting solid is filtered. Wash the obtained solid with MeOH : H 2 O = 1:1 mixed solvent and petroleum ether. After dissolving the solid in methylene chloride, it is dried over MgSO 4 , concentrated, and subjected to silicagel column to obtain 2-bromo-9H-carbazole (petroleum ether: methylene chloride = 2:1).
(3) (3) SubSub 1-6 합성 1-6 Synthesis
2-bromo-9H-carbazole (327mmol)과 iodobenzene (360mmol), 톨루엔 (2800mL)에 혼합 후에 Pd2(dba)3 (8.24g, 9mmol), PPh3 (7.87g, 30mmol), NaOt-Bu (86.5g, 900mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반 환류시킨다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 2-bromo-9-phenyl-9H-carbazole을 얻었다.After mixing in 2-bromo-9H-carbazole (327mmol), iodobenzene (360mmol) and toluene (2800mL), Pd 2 (dba) 3 (8.24g, 9mmol), PPh 3 (7.87g, 30mmol), NaO t -Bu ( 86.5 g, 900 mmol) were added, respectively, and stirred and refluxed at 100° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO 4 , concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 2-bromo-9-phenyl-9H-carbazole.
(4) (4) SubSub 1 합성 1 synthesis
2-bromo-9-phenyl-9H-carbazole (1당량)을 둥근바닥플라스크에 DMF로 녹인 후에, Bis(pinacolato)diboron (1.1당량), Pd(dppf)Cl2 (0.03당량), KOAc (3당량)를첨가하고 90℃에서 교반하였다. 반응이 완료되면 증류를 통해 DMF를 제거하고 CH2Cl2와 물로 추출하였다. 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을silicagel column 및 재결정하여 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole를 얻었다.After dissolving 2-bromo-9-phenyl-9H-carbazole (1 equivalent) with DMF in a round bottom flask, Bis(pinacolato)diboron (1.1 equivalent), Pd(dppf)Cl 2 (0.03 equivalent), KOAc (3 equivalents) ) was added and stirred at 90 °C. When the reaction was completed, DMF was removed through distillation, and the mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized by silicagel column and 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H -Carbazole was obtained.
Sub 1의 예시는 다음과 같으나 이에 한정되는 것은 아니며, 이들의 FD-MS는 하기 표 1과 같다.Examples of Sub 1 are as follows, but are not limited thereto, and their FD-MS is shown in Table 1 below.
[표 1][Table 1]
2. 2. SubSub 2의 합성 2 synthesis
상기 반응식 1의 Sub 2는 하기 반응식 3의 반응경로에 의해 합성될 수 있으며, 이에 한정된 것은 아니다.Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.
<반응식 3><Scheme 3>
(1) (One) SubSub 2-3 합성 2-3 synthesis
2L 둥근바닥플라스크에 phenylboronic acid (628mmol), THF (700mL), H2O (350mL)을 넣고 녹인 후에 1-bromo-2-iodo-3-nitrobenzene (690mmol), NaOH (1035mmol), Pd(PPh3)4 (17.3mmol)을 순서대로 넣고 80℃에서 24시간 동안 반응을 진행한다. 반응이 완료되면 메틸렌클로라이드와 물, brine을 이용하여 추출하고 MgSO4로 유기층을 건조한다. 얻어진 유기층을 silicagel column (메틸렌클로라이드 : 헥산 = 1 : 3)하여 2'-bromo-6'-nitro-1,2-dihydro-1,1'-biphenyl을 얻었다. In a 2L round-bottom flask, phenylboronic acid (628mmol), THF (700mL), H 2 O (350mL) were added and dissolved, followed by 1-bromo-2-iodo-3-nitrobenzene (690mmol), NaOH (1035mmol), Pd(PPh 3 ) 4 (17.3 mmol) is added in order, and the reaction proceeds at 80° C. for 24 hours. When the reaction is complete, extraction is performed using methylene chloride, water, and brine, and the organic layer is dried with MgSO 4 . The obtained organic layer was subjected to silicagel column (methylene chloride: hexane = 1: 3) to obtain 2'-bromo-6'-nitro-1,2-dihydro-1,1'-biphenyl.
(2) (2) SubSub 2-4 합성 2-4 synthesis
2'-bromo-6'-nitro-1,2-dihydro-1,1'-biphenyl에 triethylphosphate를 넣고 160℃ ~ 165℃ 상태에서 14시간 동안 가열 환류시킨다. 반응이 완료되면 감압증류로 남은 triethylphosphite를 제거하고, MeOH : H2O = 1:1 혼합용매로 희석시킨 후 생성된 고체를 여과한다. 얻어진 고체를 MeOH : H2O = 1:1 혼합용매와 petroleum ether로 씻어준다. 상기 고체를 메틸렌클로라이드에 녹인 후에 MgSO4로 건조하여 농축하고 silicagel column하여 4-bromo-9H-carbazole을 얻는다(petroleum ether : methylene chloride = 2:1).Add triethylphosphate to 2'-bromo-6'-nitro-1,2-dihydro-1,1'-biphenyl and heat to reflux at 160°C to 165°C for 14 hours. When the reaction is complete, the remaining triethylphosphite is removed by distillation under reduced pressure, diluted with MeOH:H 2 O = 1:1 mixed solvent, and the resulting solid is filtered. Wash the obtained solid with MeOH : H 2 O = 1:1 mixed solvent and petroleum ether. After dissolving the solid in methylene chloride, it is dried over MgSO 4 , concentrated, and subjected to silicagel column to obtain 4-bromo-9H-carbazole (petroleum ether: methylene chloride = 2:1).
(3) (3) SubSub 2 합성 2 synthesis
4-bromo-9H-carbazole (327mmol)과 iodobenzene (360mmol), 톨루엔 (2800mL)에 혼합 후에 Pd2(dba)3 (8.24g, 9mmol), PPh3 (7.87g, 30mmol), NaOt-Bu (86.5g, 900mmol)을 각각 첨가한 뒤, 100℃에서 24시간 교반 환류시킨다. ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하여 4-bromo-9-phenyl-9H-carbazole을 얻었다.After mixing in 4-bromo-9H-carbazole (327mmol), iodobenzene (360mmol) and toluene (2800mL), Pd 2 (dba) 3 (8.24g, 9mmol), PPh 3 (7.87g, 30mmol), NaO t -Bu ( 86.5 g, 900 mmol) were added, respectively, and stirred and refluxed at 100° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 4-bromo-9-phenyl-9H-carbazole.
Sub 2의 예시는 다음과 같으나 이에 한정되는 것은 아니며, 이들의 FD-MS는 하기 표 2와 같다.Examples of Sub 2 are as follows, but are not limited thereto, and their FD-MS is shown in Table 2 below.
[표 2][Table 2]
Ⅱ. 최종 생성물(II. final product ( FinalFinal ProductProduct )의 합성) synthesis
둥근바닥플라스크에 Sub 1 화합물 (1당량), Sub 2 화합물 (1.1당량), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 최종 생성물을 얻었다.Sub 1 compound (1 equiv), Sub 2 compound (1.1 equiv), Pd(PPh 3 ) 4 (0.03-0.05 equiv), NaOH (3 equiv), THF (3mL/1mmol), water (1.5mL) in a round bottom flask /1 mmol) is added. After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain a final product.
1. 1-9 합성1. 1-9 Synthesis
둥근바닥플라스크에 9-(2,4-diphenylpyrimidin-5-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (10.5g, 20mmol)을 넣고 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 10.0g (수율: 78%)을 얻었다.9-(2,4-diphenylpyrimidin-5-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (10.5 g) in a round-bottom flask , 20mmol), 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh 3 ) 4 (0.03~0.05 eq), NaOH (3 eq), THF (3mL/1mmol), water (1.5mL/1mmol) is added. After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 10.0 g (yield: 78%) of the product.
2. 2-15 합성2. 2-15 Synthesis
둥근바닥플라스크에 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (7.4g, 20mmol)을 넣고 4-bromo-9-(4-phenylquinazolin-2-yl)-9H-carbazole (9.9g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 9.2g (수율: 75%)을 얻었다.Put 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (7.4g, 20mmol) in a round bottom flask and 4-bromo-9 -(4-phenylquinazolin-2-yl)-9H-carbazole (9.9g, 22mmol), Pd(PPh 3 ) 4 (0.03-0.05 equiv), NaOH (3 equiv), THF (3mL/1mmol), water (1.5 mL/1 mmol) is added. After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 9.2 g (yield: 75%) of the product.
3. 3-1 합성3. 3-1 Synthesis
둥근바닥플라스크에 N,N-diphenyl-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)aniline (10.7g, 20mmol)을 넣고 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 9.3g (수율: 71%)을 얻었다.N,N-diphenyl-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)aniline (10.7 g, 20mmol), 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh 3 ) 4 (0.03-0.05 equiv), NaOH (3 equiv), THF (3mL/1mmol), Add water (1.5mL/1mmol). After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 9.3 g (yield: 71%) of the product.
4. 4-30 합성4. 4-30 Synthesis
둥근바닥플라스크에 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (7.4g, 20mmol)을 넣고 3'-(4-bromo-9H-carbazol-9-yl)-N,N-diphenyl-[1,1'-biphenyl]-3-amine (12.4g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 9.9g (수율: 68%)을 얻었다.Put 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (7.4g, 20mmol) in a round bottom flask and 3'-(4 -bromo-9H-carbazol-9-yl)-N,N-diphenyl-[1,1'-biphenyl]-3-amine (12.4g, 22mmol), Pd(PPh 3 ) 4 (0.03-0.05 equivalent), Add NaOH (3 eq), THF (3mL/1mmol) and water (1.5mL/1mmol). After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 9.9 g (yield: 68%) of the product.
5. 5-11 합성5. 5-11 Synthesis
둥근바닥플라스크에 12-phenyl-9-(9-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-3-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole (14.3g, 20mmol)을 넣고 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 11.1g (수율: 67%)을 얻었다.12-phenyl-9-(9-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-3-yl)- in a round bottom flask Add 12H-benzo[4,5]thieno[3,2-a]carbazole (14.3g, 20mmol) and 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh 3 ) 4 ( 0.03~0.05 equiv), NaOH (3 equiv), THF (3mL/1mmol), and water (1.5mL/1mmol) are added. After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 11.1 g (yield: 67%) of the product.
6. 6-4 합성6. 6-4 Synthesis
둥근바닥플라스크에 5-(4-phenylquinazolin-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[4,5]thieno[3,2-c]carbazole (12.1g, 20mmol)을 넣고 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 9.9g (수율: 69%)을 얻었다.5-(4-phenylquinazolin-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[4,5] in a round bottom flask Add thieno[3,2-c]carbazole (12.1g, 20mmol), 4-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh 3 ) 4 (0.03~0.05 equivalent), NaOH ( 3 eq), THF (3mL/1mmol) and water (1.5mL/1mmol). After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized using silicagel column to obtain 9.9 g (yield: 69%) of the product.
7. 6-6 합성7. 6-6 Synthesis
둥근바닥플라스크에 11-(4-phenylquinazolin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-11H-benzo[a]carbazole (10.9g, 20mmol)을 넣고 2-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3mL/1mmol), 물 (1.5mL/1mmol)을 넣는다. 그런 후에 80℃ ~ 90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 9.7g (수율: 73%)을 얻었다.11-(4-phenylquinazolin-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-11H-benzo[a]carbazole ( 10.9g, 20mmol) and 2-bromo-9-phenyl-9H-carbazole (7.1g, 22mmol), Pd(PPh 3 ) 4 (0.03-0.05 equiv), NaOH (3 equiv), THF (3mL/1mmol) , add water (1.5mL/1mmol). After that, it is heated and refluxed at 80°C to 90°C. When the reaction is complete, dilute with distilled water at room temperature, and extract with methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized by silicagel column to obtain 9.7 g (yield: 73%) of the product.
상기와 같은 합성예에 따라 제조된 화학식 1의 최종 생성물의 FD-MS의 값은 하기 표 3과 같다.The values of FD-MS of the final product of Formula 1 prepared according to the above synthesis example are shown in Table 3 below.
[표 3][Table 3]
유기전기소자의 제조평가Manufacturing evaluation of organic electric devices
[[ 실험예Experimental example Ⅰ] 그린유기발광소자( Ⅰ] Green organic light emitting device ( 정공수송층hole transport layer ))
유기 기판에 형성된 ITO층(양극) 위에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (이하, "2-TNATA"로 약기함)을 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 본 발명에 따른 화합물을 60nm 두께로 진공증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 상에 4,4'-N,N'-dicarbazole-biphenyl (이하, "CBP"로 약기함)을 호스트로, tris(2-phenylpyridine)-iridium (이하, "Ir(ppy)3"로 약기함)을 도판트로 하여 90:10 중량비로 도핑한 혼합물을 30nm 두께로 진공증착하여 발광층을 형성하였다. 이어서, 상기 발광층 상에 (1,1’-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄 (이하 "BAlq"로 약기함)을 10nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄 (이하 "Alq3"로 약칭함)을 40nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 할로젠화 알칼리 금속인 LiF를 0.2nm 두께로 증착하여 전자주입층을 형성하고, 이어서 Al을 150nm 두께로 증착하여 음극을 형성함으로써 유기전기발광소자를 제조하였다.On the ITO layer (anode) formed on the organic substrate, N 1 -(naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene- 1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then the compound according to the present invention was vacuum-deposited on the hole injection layer to a thickness of 60 nm. A hole transport layer was formed. Then, on the hole transport layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as "CBP") as a host, tris(2-phenylpyridine)-iridium (hereinafter, "Ir(ppy)" 3 ") as a dopant and a mixture doped at a weight ratio of 90:10 was vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Then, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited on the light emitting layer to a thickness of 10 nm. A hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as "Alq 3 ") was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
[[ 비교예comparative example Ⅰ] I] 비교예comparative example (1) ~ (4) (1) to (4)
비교예comparative example (1) (One)
정공수송층 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 A를 사용한 것을 제외하고는 상기 실험예 Ⅰ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that the following comparative compound A was used instead of the compound according to the present invention as the hole transport layer material.
<비교화합물 A><Comparative compound A>
비교예comparative example (2) (2)
정공수송층 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 B를 사용한 것을 제외하고는 상기 실험예 Ⅰ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that the following comparative compound B was used instead of the compound according to the present invention as the hole transport layer material.
<비교화합물 B><Comparative compound B>
비교예comparative example (3) (3)
정공수송층 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 C를 사용한 것을 제외하고는 상기 실험예 Ⅰ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that the following comparative compound C was used instead of the compound according to the present invention as the hole transport layer material.
<비교화합물 C><Comparative compound C>
비교예comparative example (4) (4)
정공수송층 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 D를 사용한 것을 제외하고는 상기 실험예 Ⅰ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that the following comparative compound D was used instead of the compound according to the present invention as the hole transport layer material.
<비교화합물 D><Comparative compound D>
이와 같이 제조된 실험예 Ⅰ(실험예(1) 내지 실험예(76)) 및 비교예 Ⅰ(비교예(1) 내지 비교예(4))에 의한 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 또한 5000cd/㎡ 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다.A forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example I (Experimental Example (1) to Experimental Example (76)) and Comparative Example I (Comparative Example (1) to Comparative Example (4)) prepared in this way. In addition, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and T95 lifespan was measured using life measuring equipment manufactured by McScience at 5000 cd/m2 standard luminance.
하기 표 4는 본 발명에 따른 화합물을 적용한 실험예 Ⅰ(실험예(1) 내지 실험예(76)) 및 비교예 Ⅰ(비교예(1) 내지 비교예(4))에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 4 below shows the device fabrication for Experimental Example I (Experimental Example (1) to Experimental Example (76)) and Comparative Example I (Comparative Example (1) to Comparative Example (4)) to which the compound according to the present invention is applied and its An evaluation result is shown.
[표 4][Table 4]
상기 표 4의 결과로부터 알 수 있듯이, 본 발명의 유기전기발광소자용 재료를 정공수송층으로 사용한 유기전기발광소자는 높은 발광효율, 낮은 구동전압 및 수명을 현저히 개선시킬 수 있다.As can be seen from the results of Table 4, the organic electroluminescent device using the material for the organic electroluminescent device of the present invention as a hole transport layer can significantly improve high luminous efficiency, low driving voltage and lifespan.
즉, NPB인 비교화합물A, 3-3'위치에 치환된 Biscarbazole인 비교화합물 B, 2-2'위치에 치환된 Biscarbazole인 비교화합물 C, 2-3'위치에 치환된 Biscarbazole인 비교화합물D 보다 2-4'위치에 치환된 Biscarbazole인 볼 발명에 따른 화합물이 우수한 소자결과를 나타내었다.That is, the comparative compound A which is NPB, the comparative compound B which is a biscarbazole substituted at the 3-3' position, the comparative compound C which is a biscarbazole substituted at the 2-2' position, and the comparative compound D which is a biscarbazole substituted at the 2-3' position. The compound according to the invention, which is a biscarbazole substituted at the 2-4' position, showed excellent device results.
<비교화합물 B> <비교화합물 C> <비교화합물 D> <1-1><Comparative compound B> <Comparative compound C> <Comparative compound D> <1-1>
이는 화합물의 꺾인 위치로 설명할 수 있는데, 상기 그림(화학식 중 굵은 부분)과 같이 비교화합물 B는 meta, 비교화합물 C는 para, 비교화합물 D는 meta인 반면 자사 발명 화합물은 ortho 위치로 비교 화합물들에 비해 꺾인 각도가 가장 큰 것을 확인할 수 있다. This can be explained by the bent position of the compound, as shown in the figure (the bold part in the formula), comparative compound B is meta, comparative compound C is para, and comparative compound D is meta, whereas our inventive compound is ortho position. It can be seen that the bending angle is the largest compared to .
이는 2개의 카바졸이 연결된 위치에 따른 결합각에 따라 밴드갭(band gap) 및 T1 값의 차이가 발생하여, 효율 및 수명에 따른 차이가 발생하는 것으로, 효율 및 수명은 o-(otho) > m-(meta) > p-(para) 순서로 나타나는 것을 확인할 수 있다. This is because the difference in the band gap and T1 value occurs depending on the bonding angle according to the position where the two carbazoles are connected, resulting in a difference according to the efficiency and lifespan, and the efficiency and lifespan are o-(otho) > It can be seen that m-(meta) > p-(para) appears in the order.
따라서, 밴드갭(band gap)과 T1 값이 커질수록 전자차단(electron blocking) 능력이 커지며, 비교적 낮은 HOMO 값을 갖게 되며, 이로 인해 발광층 내 전하균형(charge balance)이 좋아져 효율 및 수명이 상승한 것으로 판단된다.Therefore, as the band gap and T1 values increase, the electron blocking ability increases, and it has a relatively low HOMO value. is judged
[[ 실험예Experimental example Ⅱ] 레드유기발광소자( Ⅱ] Red organic light emitting device ( 발광보조층light emitting layer ))
유기 기판에 형성된 ITO층(양극) 위에 2-TNATA를 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 4,4-비스[N-(1-나프틸)-N-페닐아미노]비페닐 (이하 "NPD"로 약기함)을 60nm 두께로 진공증착하여 정공수송층을 형성하였다. 다음으로, 상기 정공수송층 상에 본 발명에 따른 화합물을 20nm 두께로 진공증착하여 발광보조층을 형성하였다. 이어서, 상기 발광보조층 상에 CBP를 호스트로, bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (이하 "(piq)2Ir(acac)"로 약기함)를 도판트로 하여 95:5 중량비로 도핑한 혼합물을 30nm 두께로 진공증착하여 발광층을 형성하였다. 이어서, 상기 발광층 상에 BAlq를 10nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3을 40nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 할로젠화 알칼리 금속인 LiF를 0.2nm 두께로 증착하여 전자주입층을 형성하고, 이어서 Al을 150nm 두께로 증착하여 음극을 형성함으로써 유기전기발광소자를 제조하였다.After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the organic substrate to form a hole injection layer, 4,4-bis[N-(1-naphthyl)-N on the hole injection layer -Phenylamino]biphenyl (hereinafter abbreviated as "NPD") was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. Next, the compound according to the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light emitting auxiliary layer. Then, on the light emitting auxiliary layer, CBP as a host and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as “(piq) 2 Ir(acac)”) as a dopant were used as a dopant in a 95:5 weight ratio. The doped mixture was vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Then, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
[[ 비교예comparative example Ⅱ] II] 비교예comparative example (5) ~ (8) (5) to (8)
비교예comparative example (5) (5)
발광보조층을 형성하지 않은 것을 제외하고는 상기 실험예 Ⅱ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that the light-emitting auxiliary layer was not formed.
비교예comparative example (6) (6)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 B를 사용한 것을 제외하고는 상기 실험예 Ⅱ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound B was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
비교예comparative example (7) (7)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 C를 사용한 것을 제외하고는 상기 실험예 Ⅱ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound C was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
비교예comparative example (8) (8)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 D를 사용한 것을 제외하고는 상기 실험예 Ⅱ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound D was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
이와 같이 제조된 실험예 Ⅱ(실험예(77) 내지 실험예(114)) 및 비교예 Ⅱ(비교예(5) 내지 비교예(8))에 의한 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 또한 2500cd/㎡ 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다.A forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example II (Experimental Example (77) to Experimental Example (114)) and Comparative Example II (Comparative Example (5) to Comparative Example (8)) thus prepared. In addition, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and T95 lifetime was measured using a life measuring device manufactured by McScience at a luminance of 2500 cd/m2.
하기 표 5는 본 발명에 따른 화합물을 적용한 실험예 Ⅱ(실험예(77) 내지 실험예(114)) 및 비교예 Ⅱ(비교예(5) 내지 비교예(8))에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 5 below shows the device fabrication for Experimental Example II (Experimental Example (77) to Experimental Example (114)) and Comparative Example II (Comparative Example (5) to Comparative Example (8)) to which the compound according to the present invention is applied An evaluation result is shown.
[표 5][Table 5]
[[ 실험예Experimental example Ⅲ] 그린유기발광소자( Ⅲ] Green organic light emitting device ( 발광보조층light emitting layer ))
유기 기판에 형성된 ITO층(양극) 위에 2-TNATA를 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 NPD를 60nm 두께로 진공증착하여 정공수송층을 형성하였다. 다음으로, 상기 정공수송층 상에 본 발명에 따른 화합물을 20nm 두께로 진공증착하여 발광보조층을 형성하였다. 이어서, 상기 발광보조층 상에 CBP를 호스트로, Ir(ppy)3을 도판트로 하여 95:5 중량비로 도핑한 혼합물을 30nm 두께로 진공증착하여 발광층을 형성하였다. 이어서, 상기 발광층 상에 BAlq를 10nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3을 40nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 할로젠화 알칼리 금속인 LiF를 0.2nm 두께로 증착하여 전자주입층을 형성하고, 이어서 Al을 150nm 두께로 증착하여 음극을 형성함으로써 유기전기발광소자를 제조하였다.After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the organic substrate to form a hole injection layer, NPD was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Next, the compound according to the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light emitting auxiliary layer. Then, a mixture doped with CBP as a host and Ir(ppy) 3 as a dopant in a 95:5 weight ratio on the light emitting auxiliary layer was vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Then, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
[[ 비교예comparative example Ⅲ] III] 비교예comparative example (9) ~ (12) (9) to (12)
비교예comparative example (9) (9)
발광보조층을 형성하지 않은 것을 제외하고는 상기 실험예 Ⅲ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that the light-emitting auxiliary layer was not formed.
비교예comparative example (10) (10)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 B를 사용한 것을 제외하고는 상기 실험예 Ⅲ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound B was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
비교예comparative example (11) (11)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 C를 사용한 것을 제외하고는 상기 실험예 Ⅲ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound C was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
비교예comparative example (12) (12)
발광보조층 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 D를 사용한 것을 제외하고는 상기 실험예 Ⅲ과 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound D was used instead of the compound according to the present invention as a light emitting auxiliary layer material.
이와 같이 제조된 실험예 Ⅲ(실험예(115) 내지 실험예(152)) 및 비교예 Ⅲ(비교예(9) 내지 비교예(12))에 의한 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 또한 5000cd/㎡ 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다.A forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example III (Experimental Example 115 to Experimental Example 152) and Comparative Example III (Comparative Example (9) to Comparative Example (12)) prepared in this way. In addition, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and T95 lifespan was measured using life measuring equipment manufactured by McScience at 5000 cd/m2 standard luminance.
하기 표 6은 본 발명에 따른 화합물을 적용한 실험예 Ⅲ(실험예(115) 내지 실험예(152)) 및 비교예 Ⅲ(비교예(9) 내지 비교예(12))에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 6 below shows the device fabrication for Experimental Example III (Experimental Example 115 to Experimental Example (152)) and Comparative Example III (Comparative Example (9) to Comparative Example (12)) to which the compound according to the present invention is applied An evaluation result is shown.
[표 6][Table 6]
상기 표 5 및 표 6의 결과로부터 알 수 있듯이, 본 발명의 유기전기발광소자용 재료를 발광보조층으로 사용할 경우 발광효율 및 수명을 현저히 개선시키는 것을 확인 할 수 있었다. 이는 상기 실험예 Ⅰ에서 설명하였듯이 2-4' 위치에 치환된 Bis-Carbazole인 본 발명에 따른 화합물은 높은 T1 에너지 레벨과 비교적 낮은 HOMO 에너지 레벨을 갖고 있어 발광층 내 전하균형(charge balance)이 좋아져 효율 및 수명이 증가되는 것으로 판단된다. As can be seen from the results of Tables 5 and 6, when the material for an organic light emitting device of the present invention is used as a light emitting auxiliary layer, it can be confirmed that the luminous efficiency and lifespan are significantly improved. As described in Experimental Example I, the compound according to the present invention, which is Bis-Carbazole substituted at the 2-4' position, has a high T1 energy level and a relatively low HOMO energy level, so that the charge balance in the light emitting layer is improved and the efficiency is improved. And it is judged that the lifespan is increased.
[[ 실험예Experimental example Ⅳ] 그린유기발광소자(인광호스트) Ⅳ] Green organic light emitting device (phosphorescent host)
유기 기판에 형성된 ITO층(양극) 위에 2-TNATA를 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 NPD를 60nm 두께로 진공증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 상에 본 발명에 따른 화합물을 호스트로, Ir(ppy)3을 도판트로 하여 95:5 중량비로 도핑한 혼합물을 30nm 두께로 진공증착하여 발광층을 형성하였다. 이어서, 상기 발광층 상에 BAlq를 10nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3을 40nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 할로젠화 알칼리 금속인 LiF를 0.2nm 두께로 증착하여 전자주입층을 형성하고, 이어서 Al을 150nm 두께로 증착하여 음극을 형성함으로써 유기전기발광소자를 제조하였다.After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the organic substrate to form a hole injection layer, NPD was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Then, a mixture doped with the compound according to the present invention as a host and Ir(ppy) 3 as a dopant in a 95:5 weight ratio on the hole transport layer was vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Then, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
[[ 비교예comparative example Ⅳ] IV] 비교예comparative example (13) ~ (16) (13) to (16)
비교예comparative example (13) (13)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 E를 사용한 것을 제외하고는 상기 실험예 Ⅳ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that the following comparative compound E was used instead of the compound according to the present invention as the host material of the light emitting layer.
<비교화합물 E><Comparative compound E>
비교예comparative example (14) (14)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 F를 사용한 것을 제외하고는 상기 실험예 Ⅳ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that the following comparative compound F was used instead of the compound according to the present invention as the host material of the light emitting layer.
<비교화합물 F><Comparative compound F>
비교예comparative example (15) (15)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 G를 사용한 것을 제외하고는 상기 실험예 Ⅳ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that the following comparative compound G was used instead of the compound according to the present invention as the host material of the light emitting layer.
<비교화합물 G><Comparative compound G>
비교예comparative example (16) (16)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 하기 비교화합물 H를 사용한 것을 제외하고는 상기 실험예 Ⅳ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that the following comparative compound H was used instead of the compound according to the present invention as the host material of the light emitting layer.
<비교화합물 H><Comparative compound H>
이와 같이 제조된 실험예 Ⅳ(실험예(153) 내지 실험예(179)) 및 비교예 Ⅳ(비교예(13) 내지 비교예(16))에 의한 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 또한 5000cd/㎡ 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다.A forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example IV (Experimental Example (153) to Experimental Example (179)) and Comparative Example IV (Comparative Example (13) to Comparative Example (16)) prepared as described above. In addition, electroluminescence (EL) characteristics were measured with PR-650 of photoresearch, and T95 lifespan was measured using life measuring equipment manufactured by McScience at 5000 cd/m2 standard luminance.
하기 표 7은 본 발명에 따른 화합물을 적용한 실험예 Ⅳ(실험예(153) 내지 실험예(179)) 및 비교예 Ⅳ(비교예(13) 내지 비교예(16))에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 7 below shows device fabrications for Experimental Example IV (Experimental Example (153) to Experimental Example (179)) and Comparative Example IV (Comparative Example (13) to Comparative Example (16)) to which the compound according to the present invention is applied An evaluation result is shown.
[표 7][Table 7]
[[ 실험예Experimental example Ⅴ] Ⅴ] 레드유기발광소자Red organic light emitting device (인광호스트)(Phosphor Host)
유기 기판에 형성된 ITO층(양극) 위에 2-TNATA를 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 NPD를 60nm 두께로 진공증착하여 정공수송층을 형성하였다. 이어서, 상기 정공주입층 상에 본 발명에 따른 화합물을 호스트로, (piq)2Ir(acac)를 도판트로 하여 95:5 중량비로 도핑한 혼합물을 30nm 두께로 진공증착하여 발광층을 형성하였다. 이어서, 상기 발광층 상에 BAlq를 10nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3을 40nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 할로젠화 알칼리 금속인 LiF를 0.2nm 두께로 증착하여 전자주입층을 형성하고, 이어서 Al을 150nm 두께로 증착하여 음극을 형성함으로써 유기전기발광소자를 제조하였다.After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the organic substrate to form a hole injection layer, NPD was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Then, a mixture doped with the compound according to the present invention as a host and (piq) 2 Ir(acac) as a dopant in a 95:5 weight ratio on the hole injection layer was vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Then, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
[[ 비교예comparative example Ⅴ] Ⅴ] 비교예comparative example (17) ~ (20) (17) to (20)
비교예comparative example (17) (17)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 E를 사용한 것을 제외하고는 상기 실험예 Ⅴ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound E was used instead of the compound according to the present invention as the host material of the light emitting layer.
비교예comparative example (18) (18)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 F를 사용한 것을 제외하고는 상기 실험예 Ⅴ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound F was used instead of the compound according to the present invention as the host material of the light emitting layer.
비교예comparative example (19) (19)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 G를 사용한 것을 제외하고는 상기 실험예 Ⅴ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that the comparative compound G was used instead of the compound according to the present invention as the host material of the light emitting layer.
비교예comparative example (20) (20)
발광층의 호스트 물질로 본 발명에 따른 화합물 대신 상기 비교화합물 H를 사용한 것을 제외하고는 상기 실험예 Ⅴ와 동일하게 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experiment V, except that the comparative compound H was used instead of the compound according to the present invention as the host material of the light emitting layer.
이와 같이 제조된 실험예 Ⅴ(실험예(180) 내지 실험예(237)) 및 비교예 Ⅴ(비교예(17) 내지 비교예(20))에 의한 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 또한 2500cd/㎡ 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다.A forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example V (Experimental Example (180) to Experimental Example (237)) and Comparative Example V (Comparative Example (17) to Comparative Example (20)) prepared in this way. In addition, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and T95 lifetime was measured using a life measuring device manufactured by McScience at a luminance of 2500 cd/m2.
하기 표 8은 본 발명에 따른 화합물을 적용한 Ⅴ(실험예(180) 내지 실험예(237)) 및 비교예 Ⅴ(비교예(17) 내지 비교예(20))에 대한 소자제작 및 그 평가 결과를 나타낸다.Table 8 below shows device fabrication and evaluation results for V (Experimental Example (180) to Experimental Example (237)) and Comparative Example V (Comparative Example (17) to Comparative Example (20)) to which the compound according to the present invention is applied. indicates
[표 8][Table 8]
상기 표 7 및 표 8의 결과로부터 알 수 있듯이, 본 발명의 유기전기발광소자용 재료를 인광호스트로 사용한 유기전기발광소자는 높은 발광효율, 낮은 구동전압 및 수명을 현저히 개선시킬 수 있다. As can be seen from the results of Tables 7 and 8, the organic light emitting device using the material for the organic light emitting device of the present invention as a phosphorescent host can significantly improve high luminous efficiency, low driving voltage and lifespan.
이는 넓은 밴드갭(band gap)을 갖는 자사발명 물질인 2,4'-bis carbazole의 경우 정공수송층으로부터 정공을 원활히 받을 수 있는 HOMO 값을 가져서 비교적 낮은 구동전압을 나타내는 것으로 판단되며, 또한 높은 T1 값으로 인하여 발광층 내 도판트(dopant) 물질과의 에너지 교환(energy transfer)이 잘 이루어져 높은 발광효율 및 수명을 갖는 것으로 판단된다.In the case of 2,4'-bis carbazole, which is a self-invented material having a wide band gap, it has a HOMO value that can smoothly receive holes from the hole transport layer, so it is judged to indicate a relatively low driving voltage, and also a high T1 value Therefore, it is judged that energy transfer with the dopant material in the light emitting layer is well made, so that it has high luminous efficiency and lifespan.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is merely illustrative of the present invention, and various modifications will be possible without departing from the essential characteristics of the present invention by those skilled in the art to which the present invention pertains. Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.
100: 유기전기소자 110: 기판
120: 제 1전극 130: 정공주입층
140: 정공수송층 141: 버퍼층
150: 발광층 151: 발광보조층
160: 전자수송층 170: 전자주입층
180: 제 2전극100: organic electric device 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode
Claims (10)
<화학식 2>
[상기 화학식 2에서,
Ar3 및 Ar4 중 하나는 퀴나졸린이고, 상기 퀴나졸린의 2번에 위치한 탄소가 상기 화학식 2의 N과 결합되며, 상기 퀴나졸린은 C10~C20의 아릴기; 플루오렌일기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기;로 이루어진 군에서 선택된 치환기로 치환되며,
상기 Ar3 및 Ar4 중 나머지 하나는 C6~C20의 아릴기이고,
R1 내지 R14는 수소이며,
여기서 상기 아릴기, 플루오렌일기, 헤테로고리기는 각각 C1~C20의 알킬기 및 C7~C20의 아릴기 중에서 선택된 하나 이상의 치환기로 치환될 수 있다.]A compound represented by the following formula (2).
<Formula 2>
[In Formula 2,
One of Ar 3 and Ar 4 is quinazoline, the carbon at position 2 of the quinazoline is bonded to N of Formula 2, and the quinazoline is a C 10 ~ C 20 aryl group; fluorenyl group; And O, N, S, Si and P containing at least one heteroatom C 2 ~ C 20 A heterocyclic group; is substituted with a substituent selected from the group consisting of,
The other one of Ar 3 and Ar 4 is a C 6 ~ C 20 aryl group,
R 1 to R 14 are hydrogen,
wherein the aryl group, the fluorenyl group, and the heterocyclic group are respectively C 1 ~ C 20 Alkyl group and C 7 ~ C 20 It may be substituted with one or more substituents selected from among aryl groups.]
하기 화합물 중 어느 하나인 것을 특징으로 하는 화합물.
The method of claim 1,
A compound, characterized in that it is any one of the following compounds.
상기 유기물층은 제 1 항 및 제 2 항 중 어느 한 항에 따르는 화합물을 포함하는 것을 특징으로 하는 유기전기소자.a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound according to any one of claims 1 and 2.
상기 유기물층은 정공수송층을 포함하며, 상기 정공수송층은 상기 화합물을 포함하는 것을 특징으로 하는 유기전기소자.4. The method of claim 3,
The organic material layer includes a hole transport layer, the hole transport layer is an organic electric device, characterized in that it includes the compound.
상기 유기물층은 발광보조층을 포함하며, 상기 발광보조층은 상기 화합물을 포함하는 것을 특징으로 하는 유기전기소자.4. The method of claim 3,
The organic material layer includes a light emission auxiliary layer, and the light emission auxiliary layer comprises the compound.
상기 유기물층은 발광층을 포함하며, 상기 화합물은 상기 발광층의 호스트 물질로 사용되는 것을 특징으로 하는 유기전기소자.4. The method of claim 3,
The organic material layer includes an emission layer, and the compound is used as a host material for the emission layer.
상기 제 1전극의 일측면 중 상기 유기물층과 반대되는 일측 또는 상기 제 2전극의 일측면 중 상기 유기물층과 반대되는 일측 중 적어도 하나에 형성되는 광효율 개선층을 더 포함하는 유기전기소자.4. The method of claim 3,
An organic electric device further comprising a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer.
상기 유기물층은 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정 및 롤투롤 공정 중 어느 하나에 의해 형성되는 것을 특징으로 하는 유기전기소자.4. The method of claim 3,
The organic material layer is an organic electric device, characterized in that formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process.
상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.A display device comprising the organic electric device of claim 3; and
An electronic device comprising a; a control unit for driving the display device.
상기 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 및 단색 또는 백색 조명용 소자 중 적어도 하나인 것을 특징으로 하는 전자장치.10. The method of claim 9,
The organic electric device is an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and an electronic device, characterized in that at least one of monochromatic or white lighting device.
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