KR102441870B1 - 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents
유기 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDFInfo
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- KR102441870B1 KR102441870B1 KR1020170107977A KR20170107977A KR102441870B1 KR 102441870 B1 KR102441870 B1 KR 102441870B1 KR 1020170107977 A KR1020170107977 A KR 1020170107977A KR 20170107977 A KR20170107977 A KR 20170107977A KR 102441870 B1 KR102441870 B1 KR 102441870B1
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- Prior art keywords
- group
- aryl
- nuclear atoms
- alkyl
- compound
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- 150000002894 organic compounds Chemical class 0.000 title description 5
- 238000005401 electroluminescence Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 239000011368 organic material Substances 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000004429 atom Chemical group 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 125000005264 aryl amine group Chemical group 0.000 claims description 26
- 125000004104 aryloxy group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 25
- 125000005104 aryl silyl group Chemical group 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 230000005525 hole transport Effects 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 4
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- 239000000463 material Substances 0.000 description 44
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
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- 125000004076 pyridyl group Chemical group 0.000 description 10
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- 239000002019 doping agent Substances 0.000 description 7
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- 125000006267 biphenyl group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- YJBOZANBVKZXFX-UHFFFAOYSA-N 9-chloro-12-azapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound ClC1=C2C(=C3C4=CC=C5C(=C4NC3=C1)C=CC=C5)C=CC=C2 YJBOZANBVKZXFX-UHFFFAOYSA-N 0.000 description 4
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- KPGPIQKEKAEAHM-UHFFFAOYSA-N 2-chloro-3-phenylquinoxaline Chemical compound ClC1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 KPGPIQKEKAEAHM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
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Images
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
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- H01L51/0067—
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Electroluminescent Light Sources (AREA)
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| PCT/KR2018/007415 WO2019039723A1 (fr) | 2017-08-25 | 2018-06-29 | Composé organique et dispositif électroluminescent organique le comprenant |
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