WO2021029598A1 - Compound for organic electronic element, organic electronic element using same, and electronic device thereof - Google Patents
Compound for organic electronic element, organic electronic element using same, and electronic device thereof Download PDFInfo
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- WO2021029598A1 WO2021029598A1 PCT/KR2020/010341 KR2020010341W WO2021029598A1 WO 2021029598 A1 WO2021029598 A1 WO 2021029598A1 KR 2020010341 W KR2020010341 W KR 2020010341W WO 2021029598 A1 WO2021029598 A1 WO 2021029598A1
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- organic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 239000011368 organic material Substances 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 29
- 239000007924 injection Substances 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000005567 fluorenylene group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000002096 quantum dot Substances 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 170
- 239000000463 material Substances 0.000 description 42
- 0 *c1c(*)[n](*)c2c(*)c(*)c(*)c(*)c12 Chemical compound *c1c(*)[n](*)c2c(*)c(*)c(*)c(*)c12 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000006872 improvement Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 238000001308 synthesis method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 10
- KPGPIQKEKAEAHM-UHFFFAOYSA-N 2-chloro-3-phenylquinoxaline Chemical compound ClC1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 KPGPIQKEKAEAHM-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BYHVGQHIAFURIL-UHFFFAOYSA-N 2-chloroquinoxaline Chemical compound C1=CC=CC2=NC(Cl)=CN=C21 BYHVGQHIAFURIL-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- OIRWTLOIOOQSFQ-UHFFFAOYSA-N ClC1=NC(=NC(=N1)C1=CC=CC2=C1C1=C(O2)C=C2C=CC=CC2=C1)C1=CC=CC=C1 Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC2=C1C1=C(O2)C=C2C=CC=CC2=C1)C1=CC=CC=C1 OIRWTLOIOOQSFQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 150000003413 spiro compounds Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical compound OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 2
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- YUFRAQHYKKPYLH-UHFFFAOYSA-N benzo[f]quinoxaline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=N1 YUFRAQHYKKPYLH-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
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- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NGTZUTGLGCUVLT-UHFFFAOYSA-N (3-naphtho[2,3-b][1]benzofuran-2-ylphenyl)boronic acid Chemical compound C1=C(C=CC2=C1C1=C(O2)C=C2C=CC=CC2=C1)C=1C=C(C=CC=1)B(O)O NGTZUTGLGCUVLT-UHFFFAOYSA-N 0.000 description 1
- UQQNPIILEFDCRF-UHFFFAOYSA-N (4-borononaphthalen-1-yl)boronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=C(B(O)O)C2=C1 UQQNPIILEFDCRF-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- JYPGHMDTTDKUEL-UHFFFAOYSA-N 2,4-dichloro-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 JYPGHMDTTDKUEL-UHFFFAOYSA-N 0.000 description 1
- ZAARQOHTIYBPNJ-UHFFFAOYSA-N 2,4-dichloro-6-naphthalen-2-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=C3C=CC=CC3=CC=2)=N1 ZAARQOHTIYBPNJ-UHFFFAOYSA-N 0.000 description 1
- RKIFNDRDRWBSCV-UHFFFAOYSA-N 2-chloro-4-phenylpyrido[3,2-d]pyrimidine Chemical compound C=12N=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 RKIFNDRDRWBSCV-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
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- RLEKCXICDMGMQK-UHFFFAOYSA-N Bc(cc1)ccc1-c1nc(-c2ccc(C(F)(F)F)cc2)nc(-c2c(c3cc(cccc4)c4cc3[o]3)c3ccc2)n1 Chemical compound Bc(cc1)ccc1-c1nc(-c2ccc(C(F)(F)F)cc2)nc(-c2c(c3cc(cccc4)c4cc3[o]3)c3ccc2)n1 RLEKCXICDMGMQK-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001522296 Erithacus rubecula Species 0.000 description 1
- OHGQAGYKUDNGIH-UHFFFAOYSA-N FC(c(cc1)ccc1-c1nc(-c2c(c3cc4ccccc4cc3[o]3)c3ccc2)nc(-c(cc2)ccc2-c2cnc(cccc3)c3n2)n1)(F)F Chemical compound FC(c(cc1)ccc1-c1nc(-c2c(c3cc4ccccc4cc3[o]3)c3ccc2)nc(-c(cc2)ccc2-c2cnc(cccc3)c3n2)n1)(F)F OHGQAGYKUDNGIH-UHFFFAOYSA-N 0.000 description 1
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- 208000006930 Pseudomyxoma Peritonei Diseases 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- HDJHJMOTVCXUGP-UHFFFAOYSA-N [1]benzofuro[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3OC2=N1 HDJHJMOTVCXUGP-UHFFFAOYSA-N 0.000 description 1
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- XEMRLVBSKVCUDL-UHFFFAOYSA-N benzo[g]quinoxaline Chemical compound N1=CC=NC2=CC3=CC=CC=C3C=C21 XEMRLVBSKVCUDL-UHFFFAOYSA-N 0.000 description 1
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 238000007641 inkjet printing Methods 0.000 description 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
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- FZQKJIHMHNYPQM-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran-9-ylboronic acid Chemical compound C1=CC=CC2=C1C1=C(O2)C=C2C=CC(=CC2=C1)B(O)O FZQKJIHMHNYPQM-UHFFFAOYSA-N 0.000 description 1
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- 239000002861 polymer material Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
- the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
- An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
- Materials used as an organic material layer in an organic electric device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.
- the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron have.
- the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.
- a host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through.
- the principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
- Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic substances caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer, and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .
- An object of the present invention is to provide a compound capable of lowering a driving voltage of a device and improving luminous efficiency and lifetime of a device, an organic electric device using the same, and an electronic device thereof.
- the present invention provides a compound represented by the following formula.
- the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
- the compound according to an embodiment of the present invention not only can the driving voltage of the device be lowered, but also the luminous efficiency, color purity, stability, and lifespan of the device can be greatly improved.
- 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
- organic electric device 110 first electrode
- first hole transport layer 340 first emission layer
- second charge generation layer 420 second hole injection layer
- aryl group and arylene group used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto.
- the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated ring system, a spiro compound, and the like.
- a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.
- fluorenyl group used in the present invention refers to a substituted or unsubstituted fluorenyl group
- fluorenylene group refers to a substituted or unsubstituted fluorenyl group, and the fluorenyl group or
- the fluorenylene group includes a spiro compound formed by bonding of R and R′ to each other in the following structure, and also includes a compound in which neighboring R′′ is bonded to each other to form a ring.
- Substituted fluorenyl group and “substituted fluorenylene group” means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the formula below, R" is 1 to 8 days I can.
- a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of the valence.
- spyro compound as used in the present invention has a'spyro linkage', and the spyro linkage refers to a linkage made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.
- heterocyclic group includes not only an aromatic ring such as a “heteroaryl group” or a “heteroarylene group”, but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto.
- heteroatom refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.
- aliphatic ring group used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It refers to a ring of 3 to 60, but is not limited thereto.
- benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.
- the'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of the group reflecting the number', but it is described as the'parent compound name' You may.
- the monovalent'group' is'phenanthryl' and the divalent group can be labeled with the valence by dividing the valency such as'phenanthrylene'. Regardless, it may be described as the parent compound name'phenanthrene'.
- pyrimidine even in the case of pyrimidine, it may be described as'pyrimidine' regardless of the valence, or in the case of monovalent, it may be described as the'name of the group' of the corresponding valency, such as a pyrimidinyl group and in the case of divalent, have.
- the substituent R 1 means that the substituent R 1 does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described.
- a is an integer of 1
- one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6
- R 1 may be the same or different from each other.
- a number in'number-condensed ring' indicates the number of condensed rings.
- a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
- a ring when expressed in the form of a'numeric resource' such as a five-membered ring or a six-membered ring, the number in'number-atomic' indicates the number of elements forming the ring.
- thiophene or furan may correspond to a five-membered ring
- benzene or pyridine may correspond to a six-membered ring.
- the ring formed by bonding of adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ⁇ C 60 aliphatic ring group; may be selected from the group consisting of.
- the term'neighboring groups' refers to the following formula as an example, between R 1 and R 2, between R 2 and R 3, between R 3 and R 4 , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and are not immediately adjacent, such as between R 1 and R 7 , R 1 and R 8 or R 4 and R 5
- Substituents bonded to ring elements may also be included.
- substituents on a ring element such as carbon or nitrogen immediately adjacent to each other, they can be neighboring groups, but if no substituent is bonded to the ring element at the immediately adjacent position, it is bonded to the next ring element. It may be a group adjacent to the substituted substituent, and also the substituents bonded to the carbon constituting the same ring may be referred to as adjacent groups.
- the expression'neighboring groups can be bonded to each other to form a ring' is used in the same meaning as'neighboring groups are selectively bonded to each other to form a ring', and at least one pair of It refers to a case where neighboring groups are bonded to each other to form a ring.
- first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term.
- a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
- a component such as a layer, film, region, or plate
- it is not only “directly over” another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is “directly above” another part, it means that there is no other part in the middle.
- 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
- an organic electric device 100 includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.
- the first electrode 110 may be an anode (anode)
- the second electrode 170 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- the organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160.
- the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.
- a light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improvement layer 180 is formed The light efficiency of the organic electric device can be improved.
- the light efficiency improvement layer 180 may be formed on the second electrode 170.
- the light efficiency improvement layer 180 is formed to form the second electrode 170.
- optical energy loss due to SPPs surface plasmon polaritons
- the light efficiency improvement layer 180 performs a buffering role for the second electrode 170 can do.
- a buffer layer or a light emission auxiliary layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2.
- an organic electric device 200 includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode.
- a hole injection layer 120 a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110
- a light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode.
- a light efficiency improvement layer 180 is formed on the second electrode.
- an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
- the organic material layer may have a form in which a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.
- two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170.
- a set or more may be formed, and a charge generation layer CGL may be formed between the stacks of organic material layers.
- the organic electric device includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a light efficiency improvement layer 180 may be included.
- the first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer 350.
- the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450.
- the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.
- a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2.
- the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361.
- the charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase current efficiency generated in each emission layer and smoothly distribute electric charges.
- the first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first emission layer 340 and the second emission layer 440 according to an embodiment of the present invention is not limited thereto.
- n may be an integer of 1-5.
- a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.
- the compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material for the light efficiency improvement layer 180, but preferably the light emitting layer 140, 340, 440 and/or the light efficiency improvement layer It can be used as a material of 180.
- band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position of the same and similar core, a study on the selection of the core and the combination of sub-substituents bonded thereto In particular, long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.
- the compound represented by Formula 1 as a material for the light emitting layers 140, 340, and 440 and/or the light efficiency improvement layer 180, the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material ( Mobility, interface characteristics, etc.) can be optimized to simultaneously improve the life and efficiency of the organic electric device.
- the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon , After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be produced by depositing a material that can be used as the cathode 170 thereon. have.
- a deposition method such as PVD or CVD.
- a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon .
- After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160 it can be produced by depositing a material that can be used as the cathode 170 thereon. have
- a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140, and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.
- the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer 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 forming method.
- the organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.
- the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
- 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.
- the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.
- a compound according to an aspect of the present invention is represented by the following formula (1).
- Y is O or S.
- L 1 to L 3 are each independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; C 3 ⁇ C 60 aliphatic ring group; And O, N, S, Si and P may be selected from the group consisting of a C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom.
- the arylene group is preferably a C 6 to C 30 arylene group, more preferably a C 6 to C 18 arylene group such as phenylene or biphenyl It may be ene, naphthylene, terphenyl, and the like.
- the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group, such as quinazoline, quinoc Saline, dibenzofuran, dibenzothiophene, and the like.
- Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; And O, N, S, Si and P selected from the group consisting of a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom, Ar 1 and Ar 2 at least one of the 2-condensation containing N It is a heterocyclic group of a ring.
- the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, It may be terphenyl, triphenylene, phenanthrene, anthracene, pyrene, and the like.
- the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 25 heterocyclic group such as pyridine, quinoxaline , Quinoline, isoquinoline, pyridopyrimidine, quinazoline, naphthyridine, pyridopyrazine, phthalazine, dibenzothiophene, dibenzofuran, benzoimidazole, benzoxazole, spiro[fluorene-9, 9'-xanthene] and the like.
- the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spy It may be robin fluorene and the like.
- R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 Alkenyl group; Alkynyl group of C 2 to C 30 ; An alkoxyl group of C 1 to C 30 ; C 6 ⁇ C 30 aryloxy group; And it is selected from the group consisting of -L'-N (R a ) (R b ), and neighboring groups may be bonded to each other to form a ring.
- a is an integer of 0 to 6
- b is an integer of 0 to 4
- the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, Terphenyl, etc.
- L' is independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ⁇ C 60 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
- R a and R b are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic ring group.
- the L 1 ⁇ L 3 , Ar 1 , Ar 2 , R 1 , R 2 , and the rings formed by bonding of adjacent groups to each other are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P
- Formula 1 may be represented by Formula 1-1 or Formula 1-2 below.
- Y, L 1 to L 3 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and X 1 to X 8 are independently of each other C, is CR or N, at least one of X 1 ⁇ X 8 is N, one of X 1 ⁇ X 8 is C.
- R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
- Formula 1 may be represented by one of Formulas 1-3 to 1-6 below.
- Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
- R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
- Formula 1 may be represented by one of Formulas 1-7 to 1-16 below.
- Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
- R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
- the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
- the present invention provides an organic electric device including an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
- the present invention provides an organic electric device including an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer.
- the light efficiency improvement layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improvement layer includes the compound represented by Formula 1 above.
- the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably the compound may be included in the emission layer.
- the organic material layer may include two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks.
- the present invention provides an electronic device including a display device including an organic electric element represented by Formula 1 and a control unit for driving the display device.
- the compound (final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub-1 and Sub-2 as shown in Scheme 1 below, but is not limited thereto.
- Core 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
- the compound belonging to Core 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
- N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 -Diamine (hereinafter abbreviated as "2-TNATA”) film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and then N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as "NPB”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
- 2-TNATA N1,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine
- the compound P-1 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as "(piq) 2 Ir(acac)") as a dopant
- a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 95:5.
- BAlq (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
- Alq 3 tris(8-quinolinol)aluminum
- LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
- Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 3 was used instead of the compound P-1 of the present invention as a host material.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used as a host material.
- Comparing Comparative Compound 1 and the compound of the present invention there is a difference in the substituent group bonded to the triazine. That is, the compound of the present invention necessarily has a 4-condensed ring containing S or O bonded to the triazine, whereas Comparative Compound 1 has a simple aryl group (naphthalene) bonded thereto. Therefore, the compound of the present invention has a higher HOMO value than Comparative Compound 1, so that holes are more easily injected into the emission layer, thereby improving the driving voltage, and the compound of the present invention in which the 4-condensed ring is introduced has a significantly narrower band gap. The efficiency also seems to have improved significantly.
- Comparative Compound 2 when comparing Comparative Compound 2 and the compound of the present invention, Comparative Compound 2 has a triazine bonded to a phenyl (simple aryl group), whereas the compound of the present invention has at least one of Ar 1 and Ar 2 of Formula 1 Since it is a 2-condensed ring containing N, there is a difference in that such a substituent is bonded to the triazine.
- the LUMO value of the compound of the present invention is deeper than that of Comparative Compound 2, electrons are more easily injected into the light emitting layer, resulting in faster driving, and improved charge blance of holes and electrons, thereby exhibiting a high lifespan.
- the compound of the present invention has a narrow band gap and excellent hole and electron mobility, so when it is used as a host, the driving voltage of the device is improved, and efficiency and lifespan are increased.
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Abstract
The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; and an electronic device comprising the organic electric element. The organic layer includes the compound represented by chemical formula 1, and thus the present invention can lower the driving voltage of the organic electronic element and increase the luminous efficiency and lifespan 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 emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, 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. 그리고 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.Materials used as an organic material layer in an organic electric device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. In addition, the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron have. In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트/도판트계를 사용할 수 있다. 그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the color purity increases and energy transfer A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through. The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
현재 휴대용 디스플레이 시장은 대면적 디스플레이로 그 크기가 증가하고 있는 추세이며, 이로 인해 기존 휴대용 디스플레이에서 요구되던 소비적력보다 더 큰 소비전력이 요구되고 있다. 따라서, 배터리라는 제한적인 전력 공급원을 가지고 있는 휴대용 디스플레이 입장에서는 소비전력이 매우 중요한 요소가 되었고, 효율과 수명 문제 또한 반드시 해결해야 하는 상황이다.Currently, the portable display market is increasing in size as a large-area display, and for this reason, power consumption that is greater than the power consumption required by the existing portable display is required. Therefore, power consumption has become a very important factor for portable displays that have a limited power supply source such as a battery, and efficiency and life issues must also be solved.
효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동 시 발생하는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만, 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면, 각 유기물층 간의 에너지 준위(energy level) 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다.Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic substances caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer, and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .
따라서 높은 열적 안정성을 가지며 발광층 내에서 효율적으로 전하 균형(charge balance)을 이룰 수 있는 발광 재료의 개발이 필요하다. 즉, 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하며, 특히 발광층의 호스트 물질에 대한 개발이 필요하다.Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. This should be preceded, and in particular, it is necessary to develop a host material for the light emitting layer.
본 발명은 소자의 구동전압을 낮추고, 소자의 발광효율 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 lowering a driving voltage of a device and improving luminous efficiency and lifetime of a 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 발명의 실시예에 따른 화합물을 이용함으로써 소자의 구동전압을 낮출 수 있을 뿐만 아니라, 소자의 발광효율, 색순도, 안정성 및 수명을 크게 향상시킬 수 있다.By using the compound according to an embodiment of the present invention, not only can the driving voltage of the device be lowered, but also the luminous efficiency, color purity, stability, and lifespan of the device can be greatly improved.
도 1 내지 도 3은 본 발명에 따른 유기전기발광소자의 예시도이다.1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
[부호의 설명][Explanation of code]
100, 200, 300: 유기전기소자 110: 제1 전극100, 200, 300: organic electric device 110: first electrode
120: 정공주입층 130: 정공수송층120: hole injection layer 130: hole transport layer
140: 발광층 150: 전자수송층140: light emitting layer 150: electron transport layer
160: 전자주입층 170: 제2 전극160: electron injection layer 170: second electrode
180: 광효율 개선층 210: 버퍼층180: light efficiency improvement layer 210: buffer layer
220: 발광보조층 320: 제1 정공주입층220: light emission auxiliary layer 320: first hole injection layer
330: 제1 정공수송층 340: 제1 발광층330: first hole transport layer 340: first emission layer
350: 제1 전자수송 층 360: 제1 전하생성층350: first electron transport layer 360: first charge generation layer
361: 제2 전하생성층 420: 제2 정공주입층361: second charge generation layer 420: second hole injection layer
430: 제2 정공수송층 440: 제2 발광층430: second hole transport layer 440: second emission layer
450: 제2 전자수송층 CGL: 전하생성층450: second electron transport layer CGL: charge generation layer
ST1: 제1 스택 ST2: 제2 스택ST1: first stack ST2: second stack
본 발명에서 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 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함할 수 있다. 또한, 본 명세서에서 다른 설명이 없는 한 아릴기에는 플루오렌일기가 포함될 수 있고 아릴렌기에는 플루오렌일렌기가 포함될 수 있다.The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated ring system, a spiro compound, and the like. In addition, unless otherwise stated in the specification, a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.
본 발명에서 사용된 용어 "플루오렌일기"는 치환 또는 비치환된 플루오렌일기를, "플루오렌일렌기"는 치환 또는 비치환된 플루오렌일기를 의미하며, 본 발명에서 사용된 플루오렌일기 또는 플루오렌일렌기는 하기 구조에서 R과 R'이 서로 결합되어 형성된 스파이로 화합물을 포함하고, 이웃한 R"이 서로 결합하여 고리를 형성한 화합물도 포함한다. The term "fluorenyl group" used in the present invention refers to a substituted or unsubstituted fluorenyl group, and "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and the fluorenyl group or The fluorenylene group includes a spiro compound formed by bonding of R and R′ to each other in the following structure, and also includes a compound in which neighboring R″ is bonded to each other to form a ring.
"치환된 플루오렌일기", "치환된 플루오렌일렌기"는 하기 구조에서 R, R', R" 중 적어도 하나가 수소 이외의 치환기인 것을 의미하며, 아래 화학식에서 R"은 1~8개일 수 있다. 본 명세서에서는 가수와 상관없이 플루오렌일기, 플루오렌일렌기, 플루오렌트리일기 등을 모두 플루오렌기라고 명명할 수도 있다."Substituted fluorenyl group" and "substituted fluorenylene group" means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the formula below, R" is 1 to 8 days I can. In the present specification, a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of the valence.
본 발명에서 사용된 용어 "스파이로 화합물"은 '스파이로 연결'을 가지며, 스파이로 연결은 2개의 고리가 오로지 1개의 원자를 공유함으로써 이루어지는 연결을 의미한다. 이때, 두 고리에 공유된 원자를 '스파이로 원자'라 하며, 한 화합물에 들어 있는 스파이로 원자의 수에 따라 이들을 각각 '모노스파이로-', '다이스파이로-', '트라이스파이로-' 화합물이라 한다.The term "spyro compound" as used in the present invention has a'spyro linkage', and the spyro linkage refers to a linkage made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.
본 발명에 사용된 용어 "헤테로고리기"는 "헤테로아릴기" 또는 "헤테로아릴렌기"와 같은 방향족 고리뿐만 아니라 비방향족 고리도 포함하며, 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 고리를 의미하나 여기에 제한되는 것은 아니다. 본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타내며, 헤테로고리기는 헤테로원자를 포함하는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 의미한다. 또한, 고리를 형성하는 탄소 대신 하기 화합물과 같이 SO2, P=O 등과 같은 헤테로원자단을 포함하는 화합물도 헤테로고리기에 포함될 수 있다.The term "heterocyclic group" as used in the present invention includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like. In addition, a compound including a heteroatom group such as SO 2 , P=O, etc. instead of carbon forming a ring may be included in the heterocyclic group.
본 발명에 사용된 용어 "지방족고리기"는 방향족탄화수소를 제외한 고리형 탄화수소를의미하며, 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함하며, 다른 설명이 없는 한 탄소수 3 내지 60의 고리를의미하나 여기에 제한되는 것은 아니다. 예컨대, 방향족고리인 벤젠과 비방향족고리인 사이클로헥산이 융합된 경우에도 지방족고리에 해당한다.The term "aliphatic ring group" used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It refers to a ring of 3 to 60, but is not limited thereto. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.
본 명세서에서 각 기호 및 그 치환기의 예로 예시되는 아릴기, 아릴렌기, 헤테로고리기 등에 해당하는 '기 이름'은 '가수를 반영한 기의 이름'을 기재할 수도 있지만, '모체화합물 명칭'으로 기재할 수도 있다. 예컨대, 아릴기의 일종인 '페난트렌'의 경우, 1가의 '기'는 '페난트릴'로 2가의 기는 '페난트릴렌' 등과 같이 가수를 구분하여 기의 이름을 기재할 수도 있지만, 가수와 상관없이 모체 화합물 명칭인 '페난트렌'으로 기재할 수도 있다. 유사하게, 피리미딘의 경우에도, 가수와 상관없이 '피리미딘'으로 기재하거나, 1가인 경우에는 피리미딘일기, 2가의 경우에는 피리미딘일렌 등과 같이 해당 가수의 '기의 이름'으로 기재할 수도 있다. In the present specification, the'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of the group reflecting the number', but it is described as the'parent compound name' You may. For example, in the case of'phenanthrene', which is a kind of aryl group, the monovalent'group' is'phenanthryl' and the divalent group can be labeled with the valence by dividing the valency such as'phenanthrylene'. Regardless, it may be described as the parent compound name'phenanthrene'. Similarly, even in the case of pyrimidine, it may be described as'pyrimidine' regardless of the valence, or in the case of monovalent, it may be described as the'name of the group' of the corresponding valency, such as a pyrimidinyl group and in the case of divalent, have.
또한, 본 명세서에서는 화합물 명칭이나 치환기 명칭을 기재함에 있어 위치를 표시하는 숫자나 알파벳 등은 생략할 수도 있다. 예컨대, 피리도[4,3-d]피리미딘을 피리도피리미딘으로, 벤조퓨로[2,3-d]피리미딘을 벤조퓨로피리미딘으로, 9,9-다이메틸-9H-플루오렌을 다이메틸플루오렌 등과 같이 기재할 수 있다. 따라서, 벤조[g]퀴녹살린이나 벤조[f]퀴녹살린을 모두 벤조퀴녹살린이라고 기재할 수 있다.In addition, in the present specification, when describing the name of the compound or the name of the substituent, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
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 is applied in the same way as the definition of the substituent group defined by the index definition of the following formula.
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하는 것을 의미하는데, 즉 a가 0인 경우는 벤젠고리를 형성하는 탄소에 모두 수소가 결합된 것을 의미하며, 이때 탄소에 결합된 수소의 표시를 생략하고 화학식이나 화합물을 기재할 수 있다. 또한, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 예컨대 아래와 같이 결합할 수 있고, a가 4 내지 6의 정수인 경우에도 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, a가 2 이상의 정수인 경우 R1은 서로 같거나 상이할 수 있다.Here, when a is an integer of 0, the substituent R 1 means that the substituent R 1 does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described. In addition, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6 In the case of an integer of, it is bonded to carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different from each other.
또한, 본 명세서에서 다른 설명이 없는 한, 축합환을 표시할 때 '숫자-축합환'에서 숫자는 축합되는 고리의 개수를 나타낸다. 예컨대, 안트라센, 페난트렌, 벤조퀴나졸린 등과 같이 3개의 고리가 서로 축합한 형태는 3-축합환으로 표기할 수 있다.In addition, unless otherwise specified in the present specification, when indicating a condensed ring, a number in'number-condensed ring' indicates the number of condensed rings. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.
또한, 본 명세서에서 다른 설명이 없는 한, 5원자 고리, 6원자 고리 등과 같이 '숫자원자' 형식으로 고리를 표현한 경우, '숫자-원자'에서 숫자는 고리를 형성하는 원소의 개수를 나타낸다. 예컨대, 싸이오펜이나 퓨란 등은 5원자 고리에 해당할 수 있고, 벤젠이나 피리딘은 6원자 고리에 해당할 수 있다.In addition, unless otherwise specified in the specification, when a ring is expressed in the form of a'numeric resource' such as a five-membered ring or a six-membered ring, the number in'number-atomic' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.
또한, 본 명세서에서 다른 설명이 없는 한, 이웃한 기끼리 서로 결합하여 형성한 고리는 C6~C60의 방향족고리기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기;로 이루어진 군에서 선택될 수 있다. In addition, unless otherwise described in the specification, the ring formed by bonding of adjacent groups to each other is a C 6 ~ C 60 aromatic ring group; Fluorenyl group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 60 aliphatic ring group; may be selected from the group consisting of.
이때, 본 명세서에서 다른 설명이 없는 한, '이웃한 기끼리'라 함은, 하기 화학식을 예로 들어 설명하면, R1과 R2끼리, R2와 R3끼리, R3과 R4끼리, R5와 R6끼리 뿐만 아니라, 하나의 탄소를 공유하는 R7과 R8끼리도 포함되고, R1과 R7끼리, R1과 R8끼리 또는 R4와 R5끼리 등과 같이 바로 인접하지 않은 고리 구성 원소(탄소나 질소 등)에 결합된 치환기도 포함될 수 있다. 즉, 바로 인접한 탄소나 질소 등과 같은 고리 구성 원소에 치환기가 있을 경우에는 이들이 이웃한 기가 될 수 있지만, 바로 인접한 위치의 고리 구성 원소에 그 어떤 치환기도 결합되지 않은 경우에는 그 다음 고리 구성 원소에 결합된 치환기와 이웃한 기가 될 수 있고, 또한 동일 고리 구성 탄소에 결합된 치환기끼리도 이웃한 기라고 할 수 있다. At this time, unless otherwise described in the specification, the term'neighboring groups' refers to the following formula as an example, between R 1 and R 2, between R 2 and R 3, between R 3 and R 4 , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and are not immediately adjacent, such as between R 1 and R 7 , R 1 and R 8 or R 4 and R 5 Substituents bonded to ring elements (such as carbon or nitrogen) may also be included. In other words, if there are substituents on a ring element such as carbon or nitrogen immediately adjacent to each other, they can be neighboring groups, but if no substituent is bonded to the ring element at the immediately adjacent position, it is bonded to the next ring element. It may be a group adjacent to the substituted substituent, and also the substituents bonded to the carbon constituting the same ring may be referred to as adjacent groups.
하기 화학식에서 R7과 R8처럼 동일 탄소에 결합된 치환기가 서로 결합하여 고리를 형성할 경우에는 스파이로 모이어티가 포함된 화합물이 형성될 수 있다.In the following formula, when substituents bonded to the same carbon as R 7 and R 8 are bonded to each other to form a ring, a compound containing a spiro moiety may be formed.
또한, 본 명세서에서 '이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다'라는 표현은 '이웃한 기끼리 서로 결합하여 선택적으로 고리를 형성한다'라는 것과 동일한 의미로 사용되며, 적어도 한 쌍의 이웃한 기끼리 서로 결합하여 고리를 형성하는 경우를 의미한다. In addition, in the present specification, the expression'neighboring groups can be bonded to each other to form a ring' is used in the same meaning as'neighboring groups are selectively bonded to each other to form a ring', and at least one pair of It refers to a case where neighboring groups are bonded to each other to form a ring.
이하, 본 발명의 화합물이 포함된 유기전기소자의 적층구조에 대하여 도 1 내지 도 3을 참조하여 설명한다.Hereinafter, a laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.
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 elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if 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 subject matter of the present invention, a detailed description thereof will be omitted.
본 발명의 구성 요소를 설명하는 데 있어서, 제1, 제2, 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 구성 요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성 요소에 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 describing the constituent elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
또한, 층, 막, 영역, 판 등의 구성 요소가 다른 구성 요소 "위에" 또는 "상에" 있다고 하는 경우, 이는 다른 구성 요소 "바로 위에" 있는 경우뿐만 아니라 그 중간에 또 다른 구성 요소가 있는 경우도 포함할 수 있다고 이해되어야 할 것이다. 반대로, 어떤 구성 요소가 다른 부분 "바로 위에" 있다고 하는 경우에는 중간에 또 다른 부분이 없는 것을 뜻한다고 이해되어야 할 것이다.In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.
도 1 내지 도 3은 본 발명의 실시예에 따른 유기전기소자의 예시도이다.1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명의 일 실시예에 따른 유기전기소자(100)는 기판(미도시) 상에 형성된 제1 전극(110)과, 제2 전극(170), 그리고 제1 전극(110)과 제2 전극(170) 사이에 형성된 유기물층을 포함한다.Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.
상기 제1 전극(110)은 애노드(양극)이고, 제2 전극(170)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제1 전극이 캐소드이고 제2 전극이 애노드일 수 있다.The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
상기 유기물층은 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함할 수 있다. 구체적으로, 제1 전극(110) 상에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)이 순차적으로 형성될 수 있다.The organic material layer may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.
바람직하게는, 상기 제1 전극(110) 또는 제2 전극(170)의 양면 중에서 유기물층과 접하지 않는 일면에 광효율개선층(180)이 형성될 수 있으며, 광효율개선층(180)이 형성될 경우 유기전기소자의 광효율이 향상될 수 있다.Preferably, a light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improvement layer 180 is formed The light efficiency of the organic electric device can be improved.
예를 들면, 제2 전극(170) 상에 광효율 개선층(180)이 형성될 수 있는데, 전면발광(top emission) 유기발광소자의 경우, 광효율 개선층(180)이 형성됨으로써 제2 전극(170)에서의 SPPs (surface plasmon polaritons)에 의한 광학 에너지 손실을 줄일 수 있고, 배면발광(bottom emission) 유기발광소자의 경우, 광효율 개선층(180)이 제2 전극(170)에 대한 완충 역할을 수행할 수 있다.For example, the light efficiency improvement layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the light efficiency improvement layer 180 is formed to form the second electrode 170. ), optical energy loss due to SPPs (surface plasmon polaritons) can be reduced, and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 performs a buffering role for the second electrode 170 can do.
정공수송층(130)과 발광층(140) 사이에 버퍼층이나 발광보조층이 더 형성될 수 있는데 이에 대해 도 2를 참조하여 설명한다.A buffer layer or a light emission auxiliary layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2.
도 2를 참조하면, 본 발명의 다른 실시예에 따른 유기전기소자(200)는 제1 전극(110) 상에 순차적으로 형성된 정공주입층(120), 정공수송층(130), 버퍼층(210), 발광보조층(220), 발광층(140), 전자수송층(150), 전자주입층(160), 제2 전극(170)을 포함할 수 있고, 제2 전극 상에 광효율개선층(180)이 형성될 수 있다.Referring to FIG. 2, an organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode. Can be.
도 2에 도시되지는 않았으나, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층이 더 형성될 수도 있다.Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
또한, 본 발명의 다른 실시예에 따르면 유기물층은 정공수송층, 발광층 및 전자수송층을 포함하는 스택이 복수개 형성된 형태일 수도 있다. 이에 대해 도 3을 참조하여 설명한다.In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.
도 3을 참조하면, 본 발명의 또 다른 실시예에 따른 유기전기소자(300)는 제1 전극(110)과 제2 전극(170) 사이에 다층으로 이루어진 유기물층의 스택(ST1, ST2)이 두 세트 이상 형성될 수 있고 유기물층의 스택 사이에 전하 생성층(CGL)이 형성될 수도 있다.Referring to FIG. 3, in an organic electric device 300 according to another embodiment of the present invention, two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170. A set or more may be formed, and a charge generation layer CGL may be formed between the stacks of organic material layers.
구체적으로, 본 발명에 일 실시예에 따른 유기전기소자는 제1 전극(110), 제1 스택(ST1), 전하 생성층(CGL: Charge Generation Layer), 제2 스택(ST2), 제2 전극(170) 및 광효율 개선층(180)을 포함할 수 있다. Specifically, the organic electric device according to the embodiment of the present invention includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a light efficiency improvement layer 180 may be included.
제1 스택(ST1)은 제1 전극(110) 상에 형성된 유기물층으로, 이는 제1 정공주입층(320), 제1 정공수송층(330), 제1 발광층(340) 및 제1 전자수송층(350)을 포함할 수 있고, 제2 스택(ST2)은 제2 정공주입층(420), 제2 정공수송층(430), 제2 발광층(440) 및 제2 전자수송층(450)을 포함할 수 있다. 이와 같이 제1 스택과 제2 스택은 동일한 적층 구조를 갖는 유기물층일 수도 있지만 서로 다른 적층 구조의 유기물층일 수도 있다.The first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer 350. ), and the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450. . As described above, the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.
제1 스택(ST1)과 제2 스택(ST2) 사이에는 전하 생성층(CGL)이 형성될 수 있다. 전하 생성층(CGL)은 제1 전하 생성층(360)과 제2 전하 생성층(361)을 포함할 수 있다. 이러한 전하 생성층(CGL)은 제1 발광층(340)과 제2 발광층(440) 사이에 형성되어 각각의 발광층에서 발생하는 전류 효율을 증가시키고, 전하를 원활하게 분배하는 역할을 한다.A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2. The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361. The charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase current efficiency generated in each emission layer and smoothly distribute electric charges.
제1 발광층(340)에는 청색 호스트에 청색 형광 도펀트를 포함하는 발광 재료가 포함될 수 있고, 제2 발광층(440)에는 녹색 호스트에 그리니쉬 옐로우(greenish yellow) 도펀트와 적색 도펀트가 함께 도핑된 재료가 포함될 수 있으나, 본 발명의 실시예에 따른 제1 발광층(340) 및 제2 발광층(440)의 재료가 이에 한정되는 것은 아니다. The first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first emission layer 340 and the second emission layer 440 according to an embodiment of the present invention is not limited thereto.
도 3에서, n은 1~5의 정수일 수 있는데, n이 2인 경우, 제2 스택(ST2) 상에 전하 생성층(CGL)과 제3 스택이 추가적으로 더 적층될 수 있다.In FIG. 3, n may be an integer of 1-5. When n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.
도 3과 같이 다층의 스택 구조 방식에 의해 발광층이 복수개 형성될 경우, 각각의 발광층에서 발광된 광의 혼합 효과에 의해 백색 광이 발광되는 유기전기발광소자를 제조할 수 있을 뿐만 아니라 다양한 색상의 광을 발광하는 유기전기발광소자를 제조할 수도 있다.When a plurality of emission layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each emission layer, as well as various colors of light. An organic electroluminescent device that emits light can also be manufactured.
본 발명의 화학식 1에 의해 표시되는 화합물은 정공주입층(120, 320, 420), 정공수송층(130, 330, 430), 버퍼층(210), 발광보조층(220), 전자수송층(150, 350, 450), 전자주입층(160), 발광층(140, 340, 440) 또는 광효율 개선층(180)의 재료로 사용될 수 있으나, 바람직하게는 발광층(140, 340, 440) 및/또는 광효율 개선층(180)의 재료로 사용될 수 있다.The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material for the light efficiency improvement layer 180, but preferably the light emitting layer 140, 340, 440 and/or the light efficiency improvement layer It can be used as a material of 180.
동일유사한 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 조합에 대한 연구가 필요하며, 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.Since the band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position of the same and similar core, a study on the selection of the core and the combination of sub-substituents bonded thereto In particular, long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.
따라서, 본 발명에서는 화학식 1로 표시되는 화합물을 발광층(140, 340, 440) 및/또는 광효율 개선층(180)의 재료로 사용함으로써, 각 유기물층 간의 에너지 레벨 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등을 최적화하여 유기전기소자의 수명 및 효율을 동시에 향상시킬 수 있다.Therefore, in the present invention, by using the compound represented by Formula 1 as a material for the light emitting layers 140, 340, and 440 and/or the light efficiency improvement layer 180, the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material ( Mobility, interface characteristics, etc.) can be optimized to simultaneously improve the life and efficiency of the organic electric device.
본 발명의 일 실시예에 따른 유기전기발광소자는 다양한 증착법(deposition)을 이용하여 제조될 수 있을 것이다. PVD나 CVD 등의 증착 방법을 사용하여 제조될 수 있는데, 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(110)을 형성하고, 그 위에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함하는 유기물층을 형성한 후, 그 위에 음극(170)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 또한, 정공수송층(130)과 발광층(140) 사이에 발광보조층(220)을, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층(미도시)을 더 형성할 수도 있고 상술한 바와 같이 스택 구조로 형성할 수도 있다.The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon , After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be produced by depositing a material that can be used as the cathode 170 thereon. have. In addition, a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140, and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.
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 material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer 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 forming method.
본 발명의 일 실시예에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.
또한, 본 발명의 일 실시예에 따른 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택될 수 있다.In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display 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. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.
이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, a compound according to an aspect of the present invention will be described.
본 발명의 일 측면에 따른 화합물은 하기 화학식 1로 표시된다.A compound according to an aspect of the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
상기 화학식 1에서 각 기호는 아래와 같이 정의될 수 있다.Each symbol in Formula 1 may be defined as follows.
Y는 O 또는 S이다.Y is O or S.
L1 내지 L3은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택될 수 있다.L 1 to L 3 are each independently a single bond; C 6 ~ C 60 arylene group; Fluorenylene group; C 3 ~ C 60 aliphatic ring group; And O, N, S, Si and P may be selected from the group consisting of a C 2 ~ C 60 heterocyclic group containing at least one heteroatom.
L1 내지 L3 중 적어도 하나가 아릴렌기인 경우, 상기 아릴렌기는 바람직하게는 C6~C30의 아릴렌기, 더욱 바람직하게는 C6~C18의 아릴렌기, 예컨대, 페닐렌, 바이페닐렌, 나프틸렌, 터페닐 등일 수 있다.When at least one of L 1 to L 3 is an arylene group, the arylene group is preferably a C 6 to C 30 arylene group, more preferably a C 6 to C 18 arylene group such as phenylene or biphenyl It may be ene, naphthylene, terphenyl, and the like.
L1 내지 L3 중에서 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C12의 헤테로고리기, 예컨대 퀴나졸린, 퀴녹살린, 다이벤조퓨란, 다이벤조싸이오펜 등일 수 있다.When at least one of L 1 to L 3 is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group, such as quinazoline, quinoc Saline, dibenzofuran, dibenzothiophene, and the like.
Ar1 및 Ar2는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택되고, Ar1과 Ar2 중에서 적어도 하나는 N을 포함하는 2-축합환의 헤테로고리기이다.Ar 1 and Ar 2 are each independently a C 6 ~ C 60 aryl group; Fluorenyl group; And O, N, S, Si and P selected from the group consisting of a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom, Ar 1 and Ar 2 at least one of the 2-condensation containing N It is a heterocyclic group of a ring.
Ar1 및 Ar2 중 적어도 하나가 아릴기인 경우, 상기 아릴기는 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 나프틸, 바이페닐, 터페닐, 트리페닐렌, 페난트렌, 안트라센, 파이렌 등일 수 있다.When at least one of Ar 1 and Ar 2 is an aryl group, the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, It may be terphenyl, triphenylene, phenanthrene, anthracene, pyrene, and the like.
Ar1 및 Ar2 중에서 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C25의 헤테로고리기, 예컨대 피리딘, 퀴녹살린, 퀴놀린, 아이소퀴놀린, 피리도피리미딘, 퀴나졸린, 나프티리딘, 피리도피라진, 프탈라진, 다이벤조싸이오펜, 다이벤조퓨란, 벤조이미다졸, 벤조옥사졸, 스파이로[플루오렌-9,9'-잔텐] 등일 수 있다.When at least one of Ar 1 and Ar 2 is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 25 heterocyclic group such as pyridine, quinoxaline , Quinoline, isoquinoline, pyridopyrimidine, quinazoline, naphthyridine, pyridopyrazine, phthalazine, dibenzothiophene, dibenzofuran, benzoimidazole, benzoxazole, spiro[fluorene-9, 9'-xanthene] and the like.
Ar1 및 Ar2 중 적어도 하나가 플루오렌일기인 경우, 상기 플루오렌일기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌, 9,9'-스파이로바이플루오렌 등일 수 있다.When at least one of Ar 1 and Ar 2 is a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spy It may be robin fluorene and the like.
R1 및 R2는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 ~ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ~ C 60 aliphatic ring group; C 1 ~ C 30 alkyl group; C 2 ~ C 30 Alkenyl group; Alkynyl group of C 2 to C 30 ; An alkoxyl group of C 1 to C 30 ; C 6 ~ C 30 aryloxy group; And it is selected from the group consisting of -L'-N (R a ) (R b ), and neighboring groups may be bonded to each other to form a ring.
a는 0~6의 정수이고, b는 0~4의 정수이며, a가 2 이상의 정수인 경우 R1 각각은 서로 같거나 상이하며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하다.a is an integer of 0 to 6, b is an integer of 0 to 4, when a is an integer of 2 or more, each of R 1 is the same or different from each other, and when b is an integer of 2 or more, each of R 2 is the same or different from each other.
R1 및 R2 중 적어도 하나가 아릴기인 경우, 상기 아릴기는 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 나프틸, 바이페닐, 터페닐 등일 수 있다.When at least one of R 1 and R 2 is an aryl group, the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, Terphenyl, etc.
상기 L'은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.L'is independently a single bond; C 6 ~ C 60 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ~ C 60 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택될 수 있다.R a and R b are each independently a C 6 ~ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 60 It may be selected from the group consisting of an aliphatic ring group.
상기 L1~L3, Ar1, Ar2, R1, R2, 및 이웃한 기끼리 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.The L 1 ~ L 3 , Ar 1 , Ar 2 , R 1 , R 2 , and the rings formed by bonding of adjacent groups to each other are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group.
상기 화학식 1은 하기 화학식 1-1 또는 화학식 1-2로 표시될 수 있다.Formula 1 may be represented by Formula 1-1 or Formula 1-2 below.
<화학식 1-1> <화학식 1-2><Formula 1-1> <Formula 1-2>
상기 화학식 1-1 및 화학식 1-2에서, Y, L1~L3, Ar1, R1, R2, a, b는 화학식 1에서 정의된 것과 같고, X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이고, X1~X8 중에서 하나는 C이다.In Formula 1-1 and Formula 1-2, Y, L 1 to L 3 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and X 1 to X 8 are independently of each other C, is CR or N, at least one of X 1 ~ X 8 is N, one of X 1 ~ X 8 is C.
상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
상기 화학식 1은 하기 화학식 1-3 내지 화학식 1-6 중에서 하나로 표시될 수 있다.Formula 1 may be represented by one of Formulas 1-3 to 1-6 below.
<화학식 1-3> <화학식 1-4><Formula 1-3> <Formula 1-4>
<화학식 1-5> <화학식 1-6><Formula 1-5> <Formula 1-6>
상기 화학식 1-3 내지 화학식 1-6에서, Y, L1~L2, Ar1, R1, R2, a, b는 화학식 1에서 정의된 것과 같고, L4는 C6~C60의 아릴렌기; 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;이며, X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이고, X1~X8 중에서 하나는 C이다.In Formulas 1-3 to 1-6, Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
상기 화학식 1은 하기 화학식 1-7 내지 화학식 1-16 중에서 하나로 표시될 수 있다.Formula 1 may be represented by one of Formulas 1-7 to 1-16 below.
<화학식 1-7> <화학식 1-8> <화학식 1-9><Formula 1-7> <Formula 1-8> <Formula 1-9>
<화학식 1-10> <화학식 1-11> <화학식 1-12><Formula 1-10> <Formula 1-11> <Formula 1-12>
<화학식 1-13> <화학식 1-14> <화학식 1-15><Formula 1-13> <Formula 1-14> <Formula 1-15>
<화학식 1-16><Formula 1-16>
상기 화학식 1-7 내지 화학식 1-16에서, Y, L1~L2, Ar1, R1, R2, a, b는 화학식 1에서 정의된 것과 같고, L4는 C6~C60의 아릴렌기; 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;이며, X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이고, X1~X8 중에서 하나는 C이다.In Formulas 1-7 to 1-16, Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중 하나일 수 있으나, 이에 한정되는 것은 아니다.Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
본 발명의 다른 측면에서, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함하는 유기전기소자를 제공하고, 이때 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다.In another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
본 발명의 또 다른 측면에서, 본 발명은 양극, 음극, 상기 양극과 음극 사이에 형성된 유기물층 및 광효율 개선층을 포함하는 유기전기소자를 제공한다. 이때, 광효율 개선층은 상기 양극 또는 음극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성되며, 상기 유기물층 또는 광효율 개선층은 상기 화학식 1로 표시되는 화합물을 포함한다.In yet another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer. In this case, the light efficiency improvement layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improvement layer includes the compound represented by Formula 1 above.
상기 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송보조층, 전자수송층 및 전자주입층 중 적어도 하나의 층을 포함하고, 바람직하게는 상기 화합물은 상기 발광층에 포함될 수 있다.The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably the compound may be included in the emission layer.
상기 유기물층은 상기 양극 상에 순차적으로 형성된 정공수송층, 발광층 및 전자수송층을 포함하는 스택을 둘 이상 포함할 수 있으며, 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함할 수 있다.The organic material layer may include two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks.
본 발명의 또 다른 측면에서, 본 발명은 상기 화학식 1로 표시되는 유기전기소자를 포함하는 디스플레이장치와, 상기 디스플레이장치를 구동하는 제어부를 포함하는 전자장치를 제공한다.In yet another aspect of the present invention, the present invention provides an electronic device including a display device including an organic electric element represented by Formula 1 and a control unit for driving the display device.
이하에서는 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 for synthesizing the compound represented by Chemical Formula 1 according to the present invention and an example for preparing an organic electric device will be described in detail, but the present invention is not limited to the following examples.
합성예Synthesis example
본 발명에 따른 화학식 1로 표시되는 화합물(final products)은 하기 반응식 1과 같이 Sub-1과 Sub-2를 반응시켜 합성될 수 있으나, 이에 한정되는 것은 아니다. The compound (final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub-1 and Sub-2 as shown in Scheme 1 below, but is not limited thereto.
<반응식 1><Reaction Scheme 1>
Core 1 합성 예시Core 1 synthesis example
반응식 1의 Core 1은 하기 반응식 2의 반응경로에 의해 합성될 수 있으나, 이에 한정된 것은 아니다. Core 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
<반응식 2> <Reaction Scheme 2>
Core 1-A의 합성예시Synthesis example of Core 1-A
Core 1-A-1의 합성Synthesis of Core 1-A-1
Naphtho[2,3-b]benzofuran-1-ylboronic acid (26.2 g, 100 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (27.1 g, 120 mmol), Pd(PPh3)4
(3.46 g, 3 mmol), NaOH (12 g, 300 mmol)을 둥근바닥플라스크에 넣고 THF 300 mL, 물 100 mL을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 25.7 g (수율: 63 %)를 얻었다.Naphtho[2,3-b]benzofuran-1-ylboronic acid (26.2 g, 100 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (27.1 g, 120 mmol), Pd(PPh 3 ) 4 (3.46 g, 3 mmol) and NaOH (12 g, 300 mmol) were added to a round bottom flask, and 300 mL of THF and 100 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 25.7 g (yield: 63%) of the product.
Core 1-A-2의 합성Synthesis of Core 1-A-2
Naphtho[2,3-b]benzofuran-3-ylboronic acid (15 g, 57.2 mmol), 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (19 g, 68.7 mmol), Pd(PPh3)4
(3.3 g, 2.9 mmol), NaOH (6.9 g, 171 mmol)을 둥근바닥플라스크에 넣고 THF 300 mL, 물 100 mL을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 20.2 g (수율: 77 %)를 얻었다.Naphtho[2,3-b]benzofuran-3-ylboronic acid (15 g, 57.2 mmol), 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (19 g, 68.7 mmol), Pd(PPh 3 ) 4 (3.3 g, 2.9 mmol) and NaOH (6.9 g, 171 mmol) were placed in a round bottom flask, and 300 mL of THF and 100 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 20.2 g (yield: 77%) of the product.
Core 1-A-3의 합성Synthesis of Core 1-A-3
Naphtho[2,3-b]benzofuran-9-ylboronic acid (17 g, 64.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5-triazine (23.5 g, 77.8 mmol), Pd(PPh3)4
(3.8 g, 3.2 mmol), NaOH (7.8 g, 194.6 mmol)을 둥근바닥플라스크에 넣고 THF 300 mL, 물 100 mL을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 23.6 g (수율: 75 %)를 얻었다.Naphtho[2,3-b]benzofuran-9-ylboronic acid (17 g, 64.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4,6-dichloro-1,3,5 -triazine (23.5 g, 77.8 mmol), Pd(PPh 3 ) 4 (3.8 g, 3.2 mmol) and NaOH (7.8 g, 194.6 mmol) were added to a round bottom flask, and 300 mL of THF and 100 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 23.6 g (yield: 75%) of the product.
Core 1-A-4의 합성Synthesis of Core 1-A-4
(3-(naphtho[2,3-b]benzofuran-2-yl)phenyl)boronic acid (16 g, 47.3 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (12.9 g, 56.8 mmol), Pd(PPh3)4
(2.7 g, 2.4 mmol), NaOH (5.7 g, 141.9 mmol)을 둥근바닥플라스크에 넣고 THF 300 mL, 물 100 mL을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 16.3 g (수율: 71 %)를 얻었다.(3-(naphtho[2,3-b]benzofuran-2-yl)phenyl)boronic acid (16 g, 47.3 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (12.9 g , 56.8 mmol), Pd(PPh 3 ) 4 (2.7 g, 2.4 mmol) and NaOH (5.7 g, 141.9 mmol) were placed in a round bottom flask, and 300 mL of THF and 100 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 16.3 g (yield: 71%) of the product.
Core 1의 합성예시Synthesis example of Core 1
(1) Core-1 합성(1) Core-1 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine (40.7 g, 100 mmol)와 1,4-phenylenediboronic acid (24.8 g, 150 mmol), Pd(PPh3)4
(3.46 g, 3 mmol), NaOH (12 g, 300 mmol)을 둥근바닥플라스크에 넣고 Toluene 300 mL, Ethanol 100ml, 물 100 mL을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 26.1 g (수율: 53 %)를 얻었다.2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine (40.7 g, 100 mmol) and 1,4-phenylenediboronic acid (24.8 g , 150 mmol), Pd(PPh 3 ) 4 (3.46 g, 3 mmol) and NaOH (12 g, 300 mmol) were placed in a round bottom flask, 300 mL of Toluene, 100 mL of Ethanol, and 100 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.1 g (yield: 53%) of the product.
(2) Core-5 합성(2) Core-5 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine 대신 4-(4-chloro-6-(naphtho[2,3-b]benzofuran-1-yl)-1,3,5-triazin-2-yl)benzonitrile (43.2 g, 100 mmol)을 사용하여 상기 Core-1의 합성법과 같은 방법으로 진행시켜서 생성물 25.4 g (수율: 49 %)를 얻었다.4-(4-chloro-6-(naphtho[2,3-) instead of 2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine b]benzofuran-1-yl)-1,3,5-triazin-2-yl)benzonitrile (43.2 g, 100 mmol) and proceed in the same manner as the synthesis method of Core-1, and the product 25.4 g (yield: 49%).
(3) Core-43 합성(3) Core-43 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine 대신 2-(benzo[b]naphtho[2,3-d]thiophen-1-yl)-4-chloro-6-phenyl-1,3,5-triazine (42.3 g, 100 mmol)를, 1,4-phenylenediboronic acid 대신 naphthalene-1,4-diyldiboronic acid (32.3 g, 150 mmol)를 사용하여 상기 Core-1의 합성법과 같은 방법으로 진행시켜서 생성물 26.3 g (수율: 47 %)를 얻었다.2-(benzo[b]naphtho[2,3-d]thiophen instead of 2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine -1-yl)-4-chloro-6-phenyl-1,3,5-triazine (42.3 g, 100 mmol), instead of 1,4-phenylenediboronic acid, naphthalene-1,4-diyldiboronic acid (32.3 g, 150 mmol) to obtain 26.3 g (yield: 47%) of the product by proceeding in the same manner as in the synthesis method of Core-1.
(4) Core-54 합성(4) Core-54 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(naphthalen-1-yl)-6-(naphtho[2,3-b]benzofuran-11-yl)-1,3,5-triazine (45.7 g, 100 mmol)를 사용하여 상기 Core-1의 합성법과 같은 방법으로 진행시켜서 생성물 28.3 g (수율: 55 %)를 얻었다.2-chloro-4-(naphthalen-1-yl)-6- instead of 2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine Using (naphtho[2,3-b]benzofuran-11-yl)-1,3,5-triazine (45.7 g, 100 mmol), proceed in the same manner as the synthesis method of Core-1, and the product 28.3 g (yield : 55%) was obtained.
(5) Core-60 합성(5) Core-60 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(naphtho[2,3-b]benzofuran-2-yl)-6-phenyl-1,3,5-triazine (40.7 g, 100 mmol)를 사용하여 상기 Core-1의 합성법과 같은 방법으로 진행시켜서 생성물 19.7 g (수율: 40 %)를 얻었다.2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine instead of 2-chloro-4-(naphtho[2,3-b]benzofuran -2-yl)-6-phenyl-1,3,5-triazine (40.7 g, 100 mmol) was used in the same manner as the synthesis method of Core-1 to obtain 19.7 g (yield: 40%) of the product. .
(6) Core-69 합성(6) Core-69 synthesis
2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine 대신 2-(benzo[b]naphtho[2,3-d]thiophen-2-yl)-4-chloro-6-(naphthalen-1-yl)-1,3,5-triazine (47.3 g, 100 mmol)를 사용하여 상기 Core-1의 합성법과 같은 방법으로 진행시켜서 생성물 33 g (수율: 59 %)를 얻었다.2-(benzo[b]naphtho[2,3-d]thiophen instead of 2-chloro-4-(naphtho[2,3-b]benzofuran-1-yl)-6-phenyl-1,3,5-triazine -2-yl)-4-chloro-6-(naphthalen-1-yl)-1,3,5-triazine (47.3 g, 100 mmol) and proceed in the same manner as the synthesis method of Core-1 33 g (yield: 59%) was obtained.
Core 1에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 1은 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.The compound belonging to Core 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
[표 1][Table 1]
최종 화합물의 합성 예시Synthesis example of final compound
P-1 합성예시Synthesis example of P-1
Core-1 (4.33 g, 10 mmol), 2-chloro-3-phenylquinoxaline (2.88 g, 12 mmol), Pd(PPh3)4
(0.34 g, 0.3 mmol), NaOH (1.2 g, 30 mmol)을 둥근바닥플라스크에 넣고, THF 30 mL, 물 10 mL을 첨가한 후 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 4.89 g (수율: 75 %)를 얻었다.Core-1 (4.33 g, 10 mmol), 2-chloro-3-phenylquinoxaline (2.88 g, 12 mmol), Pd(PPh 3 ) 4 (0.34 g, 0.3 mmol) and NaOH (1.2 g, 30 mmol) were added to a round bottom flask, and 30 mL of THF and 10 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 4.89 g (yield: 75%) of the product.
P-5 합성예시Synthesis example of P-5
Core-1 대신 Core-5 (5.18 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloroquinoxaline (1.97 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 5.05 g (수율: 84 %)를 얻었다. Core-5 (5.18 g, 10 mmol) instead of Core-1 and 2-chloroquinoxaline (1.97 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline were used to proceed in the same manner as in the synthesis method of P-1. 5.05 g (yield: 84%) was obtained.
P-18 합성예시Synthesis example of P-18
Core-1 대신 Core-18 (6.19 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloro-4-phenylpyrido[3,2-d]pyrimidine (2.9 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 6.16 g (수율: 79 %)를 얻었다.Core-18 (6.19 g, 10 mmol) instead of Core-1, and 2-chloro-4-phenylpyrido[3,2-d]pyrimidine (2.9 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline Proceeding in the same manner as in the synthesis method of P-1, the product 6.16 g (yield: 79%) was obtained.
P-36 합성예시Synthesis example of P-36
Core-1 대신 Core-36 (5.61 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloroquinoxaline (1.97 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 4.96 g (수율: 77 %)를 얻었다.Core-36 (5.61 g, 10 mmol) instead of Core-1 and 2-chloroquinoxaline (1.97 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline were used to proceed in the same manner as in the synthesis method of P-1. 4.96 g (yield: 77%) was obtained.
P-50 합성예시Synthesis example of P-50
Core-1 대신 Core-43 (5.59 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloroquinoxaline (1.97 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 4.88 g (수율: 76 %)를 얻었다.Core-43 (5.59 g, 10 mmol) instead of Core-1 and 2-chloroquinoxaline (1.97 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline were used to proceed in the same manner as in the synthesis method of P-1. 4.88 g (yield: 76%) was obtained.
P-64 합성예시Synthesis example of P-64
Core-1 대신 Core-54 (5.43 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloroquinoxaline (1.97 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 4.76 g (수율: 76 %)를 얻었다.Core-54 (5.43 g, 10 mmol) instead of Core-1 and 2-chloroquinoxaline (1.97 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline were used to proceed in the same manner as in the synthesis method of P-1. 4.76 g (yield: 76%) was obtained.
P-69 합성예시Synthesis example of P-69
Core-1 대신 Core-58 (5.59 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloroquinoxaline (2.88 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 5.32 g (수율: 74 %)를 얻었다.Core-58 (5.59 g, 10 mmol) instead of Core-1 and 2-chloroquinoxaline (2.88 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline were used to proceed in the same manner as the synthesis method of P-1. 5.32 g (yield: 74%) was obtained.
P-71 합성예시Synthesis example of P-71
Core-1 대신 Core-60 (4.93 g, 10 mmol)를, 2-chloro-3-phenylquinoxaline 대신 2-chloro-3-phenylquinoxaline (2.88 g, 12 mmol)을 사용하여 상기 P-1의 합성법과 같은 방법으로 진행시켜서 생성물 5.22 g (수율: 80 %)를 얻었다.Using Core-60 (4.93 g, 10 mmol) instead of Core-1 and 2-chloro-3-phenylquinoxaline (2.88 g, 12 mmol) instead of 2-chloro-3-phenylquinoxaline, the same method as the synthesis method of P-1 To obtain a product 5.22 g (yield: 80%)
상기와 같은 합성예에 따라 제조된 본 발명의 화합물 P-1 내지 P-100의 FD-MS 값은 하기 표 2와 같다.The FD-MS values of the compounds P-1 to P-100 of the present invention prepared according to the synthesis example as described above are shown in Table 2 below.
[표 2][Table 2]
유기전기소자의 제조평가Manufacturing evaluation of organic electric devices
[[
실시예Example
1] One]
적색유기전기발광소자Red organic electroluminescent device
(인광호스트) (Phosphorescent host)
유리 기판에 형성된 ITO층(양극) 상에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (이하"2-TNATA"로 약기함)막을 진공증착하여 60 nm 두께의 정공주입층을 형성한 후, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하"NPB"로 약기함) 막을 60 nm 두께로 진공증착하여 정공수송층을 형성하였다. On the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 -Diamine (hereinafter abbreviated as "2-TNATA") film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and then N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as "NPB") was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
이후, 상기 정공수송층 상에 본 발명의 화합물 P-1을 호스트 물질로, bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (이하, "(piq)2Ir(acac)"로 약기함)를 도펀트 물질로 사용하되 이들 중량비가 95:5가 되도록 도펀트를 도핑하여 30nm 두께의 발광층을 증착하였다. Thereafter, on the hole transport layer, the compound P-1 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as "(piq) 2 Ir(acac)") as a dopant Although used as a material, a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 95:5.
다음으로, 상기 발광층 상에 (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (이하 "BAlq"로 약기함)을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하여 전자수송층을 형성하였다. Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer. And tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq 3 ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
이후, 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성하고, 상기 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성하였다.Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
[[
실시예Example
2] 내지 [ 2] to [
실시예Example
15] 15]
호스트 물질로 본 발명의 화합물 P-1 대신 하기 표 3에 기재된 본 발명의 화합물을 사용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 3 was used instead of the compound P-1 of the present invention as a host material.
[[
비교예Comparative example
1] One]
및 [비교예And [Comparative Example
2] 2]
호스트 물질로 하기 비교화합물 1 또는 비교화합물 2를 사용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used as a host material.
<비교화합물 1> <비교화합물 2> <Comparative compound 1> <Comparative compound 2>
본 발명의 실시예 1 내지 실시예 15, 비교예 1 및 비교예 2에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 2500cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 3과 같다.By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 15, Comparative Examples 1 and 2 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. It was measured, and the T95 life was measured using a life measurement equipment of McScience at a reference luminance of 2500 cd/m 2 . The measurement results are shown in Table 3 below.
[표 3] [Table 3]
상기 표 3의 결과로부터 알 수 있듯이, 본 발명의 화합물을 발광층 재료로 사용할 경우, 비교화합물 1 및 2를 사용한 경우에 비해 효율과 수명이 현저히 개선되는 것을 알 수 있다. 비교예 1은 비교예 2보다 구동전압 및 효율이 개선되었으며, 비교예 1보다 실시예 1 내지 실시예 15의 경우 구동전압, 효율 및 수명이 모두 현저히 개선되었다.As can be seen from the results of Table 3, when the compound of the present invention is used as a light emitting layer material, it can be seen that the efficiency and lifespan are significantly improved compared to the case of using Comparative Compounds 1 and 2. In Comparative Example 1, the driving voltage and efficiency were improved compared to Comparative Example 2, and in Examples 1 to 15 than in Comparative Example 1, the driving voltage, efficiency, and life were all significantly improved.
비교화합물 1과 본 발명의 화합물을 비교해보면, 트리아진에 결합된 치환기에 있어 차이가 있다. 즉, 본 발명의 화합물은 반드시 S 또는 O를 포함하는 4-축합환이 트리아진에 결합되어 있는 반면, 비교화합물 1은 단순 아릴기(나프탈렌)가 결합되어 있다. 따라서, 본 발명의 화합물은 비교화합물 1에 비해 HOMO값이 높아 정공이 발광층으로 보다 쉽게 주입되어 구동전압이 개선되었고, 또한 4-축합환을 도입한 본 발명의 화합물은 밴드갭이 크게 좁아지게 되면서 효율 또한 크게 향상된 것으로 보인다.Comparing Comparative Compound 1 and the compound of the present invention, there is a difference in the substituent group bonded to the triazine. That is, the compound of the present invention necessarily has a 4-condensed ring containing S or O bonded to the triazine, whereas Comparative Compound 1 has a simple aryl group (naphthalene) bonded thereto. Therefore, the compound of the present invention has a higher HOMO value than Comparative Compound 1, so that holes are more easily injected into the emission layer, thereby improving the driving voltage, and the compound of the present invention in which the 4-condensed ring is introduced has a significantly narrower band gap. The efficiency also seems to have improved significantly.
또한, 비교화합물 2와 본 발명의 화합물을 비교해보면, 비교화합물 2는 트리아진에 페닐(단순 아릴기)이 결합되어 있는 반면, 본 발명의 화합물은 화학식 1의 Ar1과 Ar2 중에서 적어도 하나가 N을 포함하는 2-축합환이므로 트리아진에 이러한 치환기가 결합되어 있다는 점에서 차이가 있다. 이러한 본 발명의 화합물은 비교화합물 2에 비해 LUMO 값이 깊어짐에 따라 전자가 발광층으로 보다 쉽게 주입되어 구동이 빨라졌고, 정공과 전자의 charge blance가 향상되어 고수명을 나타내었다.In addition, when comparing Comparative Compound 2 and the compound of the present invention, Comparative Compound 2 has a triazine bonded to a phenyl (simple aryl group), whereas the compound of the present invention has at least one of Ar 1 and Ar 2 of Formula 1 Since it is a 2-condensed ring containing N, there is a difference in that such a substituent is bonded to the triazine. As the LUMO value of the compound of the present invention is deeper than that of Comparative Compound 2, electrons are more easily injected into the light emitting layer, resulting in faster driving, and improved charge blance of holes and electrons, thereby exhibiting a high lifespan.
즉, 비교화합물 1 및 비교화합물 2에 비해 본 발명의 화합물은 band gap이 좁고, 정공 및 전자 이동 능력이 우수하므로 이를 호스트로 사용할 경우, 소자의 구동전압이 향상되고 효율 및 수명이 증가한 것으로 보인다.That is, compared to Comparative Compound 1 and Comparative Compound 2, the compound of the present invention has a narrow band gap and excellent hole and electron mobility, so when it is used as a host, the driving voltage of the device is improved, and efficiency and lifespan are increased.
이러한 결과는 유사한 화합물일지라도 치환기의 종류에 따라 화합물의 에너지 레벨이나 박막 특성이 현저히 달라지게 되고, 이와 같은 차이가 소자 증착 시 소자 성능 향상에 주요인자(Band gap, 안정성 등)로 작용하여 소자 결과가 달라질 수 있음을 시사하고 있다. This result is that even for similar compounds, the energy level or thin film characteristics of the compound are significantly different depending on the type of substituent, and this difference acts as a major factor (band gap, stability, etc.) in improving device performance during device deposition, resulting in device results. It suggests that it may be different.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명에 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 내의 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.
CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION
본 특허출원은 2019년 08월 14일 한국에 출원한 특허출원번호 제10-2019-0099758호에 대해 미국 특허법 119조 내지 121조, 365조 (35 U.S.C §119조 내지 §121조, §365조)에 따라 우선권을 주장하며, 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다. 아울러, 본 특허출원은 미국 이외에 국가에 대해서도 위와 동일한 이유로 우선권을 주장하면 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다.This patent application is for patent application No. 10-2019-0099758 filed in Korea on August 14, 2019, in the U.S. Patent Law Articles 119 to 121, 365 (35 USC §119 to §121, §365) ), and all the contents are incorporated into this patent application by reference. In addition, if this patent application claims priority for countries other than the United States for the same reason as above, all the contents are incorporated into this patent application as references.
Claims (13)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):<화학식 1><Formula 1>
상기 화학식 1에서,In Formula 1,Y는 O 또는 S이며,Y is O or S,L1 내지 L3은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택되며,L 1 to L 3 are each independently a single bond; C 6 ~ C 60 arylene group; Fluorenylene group; C 3 ~ C 60 aliphatic ring group; And O, N, S, Si and P is selected from the group consisting of a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom,Ar1 및 Ar2는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택되고, Ar1과 Ar2 중에서 적어도 하나는 N을 포함하는 2-축합환의 헤테로고리기이며,Ar 1 and Ar 2 are each independently a C 6 ~ C 60 aryl group; Fluorenyl group; And O, N, S, Si and P selected from the group consisting of a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom, Ar 1 and Ar 2 at least one of the 2-condensation containing N It is a heterocyclic group of a ring,R1 및 R2는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있으며,R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 ~ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ~ C 60 aliphatic ring group; C 1 ~ C 30 alkyl group; C 2 ~ C 30 Alkenyl group; Alkynyl group of C 2 to C 30 ; An alkoxyl group of C 1 to C 30 ; C 6 ~ C 30 aryloxy group; And it is selected from the group consisting of -L'-N (R a ) (R b ), and neighboring groups can be bonded to each other to form a ring,a는 0~6의 정수이고, b는 0~4의 정수이며, a가 2 이상의 정수인 경우 R1 각각은 서로 같거나 상이하며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하며,a is an integer from 0 to 6, b is an integer from 0 to 4, and when a is an integer of 2 or more, each of R 1 is the same or different from each other, and when b is an integer of 2 or more, each of R 2 is the same or different from each other,상기 L'은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,L'is independently a single bond; C 6 ~ C 60 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ~ C 60 aliphatic ring group; And it is selected from the group consisting of a combination thereof,상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택되며,R a and R b are each independently a C 6 ~ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 60 is selected from the group consisting of an aliphatic ring group,상기 L1~L3, Ar1, Ar2, R1, R2, 및 이웃한 기끼리 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.The L 1 ~ L 3 , Ar 1 , Ar 2 , R 1 , R 2 , and the rings formed by bonding of adjacent groups to each other are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group. - 제 1항에서 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 1-1 또는 화학식 1-2로 표시되는 것을 특징으로 하는 화합물:Formula 1 is a compound characterized in that represented by Formula 1-1 or Formula 1-2:<화학식 1-1> <화학식 1-2><Formula 1-1> <Formula 1-2>
상기 화학식 1-1 및 화학식 1-2에서, Y, L1~L3, Ar1, R1, R2, a, b는 제1항에서 정의된 것과 같고,In Formulas 1-1 and 1-2, Y, L 1 to L 3 , Ar 1 , R 1 , R 2 , a, b are the same as defined in claim 1,X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이며,X 1 to X 8 are each independently C, CR, or N, and at least one of X 1 to X 8 is N,상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group. - 제 1항에서 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 1-3 내지 화학식 1-6 중에서 하나로 표시되는 것을 특징으로 하는 화합물:Formula 1 is a compound characterized in that represented by one of the following formulas 1-3 to 1-6:<화학식 1-3> <화학식 1-4><Formula 1-3> <Formula 1-4>
<화학식 1-5> <화학식 1-6><Formula 1-5> <Formula 1-6>
상기 화학식 1-3 내지 화학식 1-6에서, Y, L1~L2, Ar1, R1, R2, a, b는 제1항에서 정의된 것과 같고,In Formulas 1-3 to 1-6, Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are the same as defined in claim 1,L4는 C6~C60의 아릴렌기; 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;이며,L 4 is a C 6 ~ C 60 arylene group; Or a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom of O, N, S, Si and P; and,X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이며,X 1 to X 8 are each independently C, CR, or N, and at least one of X 1 to X 8 is N,상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group. - 제 1항에서 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 1-7 내지 화학식 1-16 중에서 하나로 표시되는 것을 특징으로 하는 화합물:Formula 1 is a compound characterized in that represented by one of the following formulas 1-7 to 1-16:<화학식 1-7> <화학식 1-8> <화학식 1-9><Formula 1-7> <Formula 1-8> <Formula 1-9>
<화학식 1-10> <화학식 1-11> <화학식 1-12><Formula 1-10> <Formula 1-11> <Formula 1-12>
<화학식 1-13> <화학식 1-14> <화학식 1-15><Formula 1-13> <Formula 1-14> <Formula 1-15>
<화학식 1-16><Formula 1-16>
상기 화학식 1-7 내지 화학식 1-16에서, Y, L1~L2, Ar1, R1, R2, a, b는 제1항에서 정의된 것과 같고,In Formulas 1-7 to 1-16, Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are the same as defined in claim 1,L4는 C6~C60의 아릴렌기; 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;이며,L 4 is a C 6 ~ C 60 arylene group; Or a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom of O, N, S, Si and P; and,X1 내지 X8은 서로 독립적으로 C, CR 또는 N이고, X1~X8 중에서 적어도 하나는 N이며,X 1 to X 8 are each independently C, CR, or N, and at least one of X 1 to X 8 is N,상기 R은 수소, 중수소; 할로겐; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루로 이루어진 군에서 선택된다.R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group. - 제 1항에 있어서, The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화합물 중 하나인 것을 특징으로 하는 화합물:The compound represented by Formula 1 is a compound characterized in that one of the following compounds:
.
. - 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서,In an organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,상기 유기물층은 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device, characterized in that the organic material layer comprises a compound represented by the formula (1) of claim 1.
- 제 6항에 있어서,The method of claim 6,상기 양극의 양면 또는 상기 음극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성된 광효율 개선층을 더 포함하는 것을 특징으로 하는 유기전기소자.An organic electric device, further comprising a light efficiency improving layer formed on one surface of the anode or both surfaces of the cathode that is not in contact with the organic material layer.
- 제 6항에 있어서,The method of claim 6,상기 유기물층은 정공주입층, 정공 수송층, 발광보조층, 발광층, 전자수송보조층, 전자수송층 및 전자주입층 중 적어도 하나를 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer.
- 제 8항에 있어서,The method of claim 8,상기 화합물은 상기 발광층 및 발광보조층 중에서 적어도 하나에 포함되는 것을 특징으로 하는 유기전기소자.The compound is an organic electric device, characterized in that included in at least one of the light emitting layer and the light emitting auxiliary layer.
- 제 6항에 있어서,The method of claim 6,상기 유기물층은 상기 양극 상에 순차적으로 형성된 정공수송층, 발광층 및 전자수송층을 포함하는 스택을 둘 이상 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer comprises two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode.
- 제 10항에 있어서,The method of claim 10,상기 유기물층은 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device further comprises a charge generation layer formed between the two or more stacks.
- 제6항의 유기전기소자를 포함하는 디스플레이장치; 및 A display device comprising the organic electric device of claim 6; And상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.Electronic device including; a control unit for driving the display device.
- 제 12항에 있어서,The method of claim 12,상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택되는 것을 특징으로 하는 전자장치.The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
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| CN116217557A (en) * | 2021-12-02 | 2023-06-06 | 常州强力昱镭光电材料有限公司 | Dibenzofuran-containing compound and organic electroluminescent element |
| WO2024071841A1 (en) * | 2022-09-29 | 2024-04-04 | 주식회사 엘지화학 | Novel compound and organic light-emitting device comprising same |
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