WO2022086149A1 - Compound for organic electronic device, organic electronic device including same, and display apparatus including organic electronic device - Google Patents
Compound for organic electronic device, organic electronic device including same, and display apparatus including organic electronic device Download PDFInfo
- Publication number
- WO2022086149A1 WO2022086149A1 PCT/KR2021/014640 KR2021014640W WO2022086149A1 WO 2022086149 A1 WO2022086149 A1 WO 2022086149A1 KR 2021014640 W KR2021014640 W KR 2021014640W WO 2022086149 A1 WO2022086149 A1 WO 2022086149A1
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- WIPO (PCT)
- Prior art keywords
- formula
- substituted
- unsubstituted
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- electronic device
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
- 239000011737 fluorine Substances 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 239000011368 organic material Substances 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 7
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000000126 substance Substances 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 66
- 150000002431 hydrogen Chemical class 0.000 description 21
- 239000000463 material Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000005001 aminoaryl group Chemical group 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- IFDACOHISNXTPJ-UHFFFAOYSA-N 13-iodo-N,N-diphenyl-2,9-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaen-6-amine Chemical compound IC1=CC2=CN=C3C=C(C=C4C3=C2C(=C1)N=C4)N(C4=CC=CC=C4)C4=CC=CC=C4 IFDACOHISNXTPJ-UHFFFAOYSA-N 0.000 description 3
- YNDWPTUMTXBVCS-UHFFFAOYSA-N 4-(4-cyano-N-[13-(N-phenylanilino)-2,9-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaen-6-yl]anilino)benzonitrile Chemical compound C1(=CC=CC=C1)N(C1=CC2=CN=C3C=C(C=C4C3=C2C(=C1)N=C4)N(C4=CC=C(C#N)C=C4)C4=CC=C(C#N)C=C4)C4=CC=CC=C4 YNDWPTUMTXBVCS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XEJVJHWAPMULAQ-UHFFFAOYSA-N 4-(7-bromopyren-2-yl)-N,N-diphenylaniline Chemical compound BrC=1C=C2C=CC3=CC(=CC4=CC=C(C1)C2=C43)C4=CC=C(N(C3=CC=CC=C3)C3=CC=CC=C3)C=C4 XEJVJHWAPMULAQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000000376 reactant Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 1
- AQDSOACLMYTLBR-UHFFFAOYSA-N 6,13-diiodo-2,9-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical compound IC1=CC2=CN=C3C=C(C=C4C=NC(=C1)C2=C43)I AQDSOACLMYTLBR-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- LGLJXZWEUGZQRX-UHFFFAOYSA-N n,n-diphenyl-6-[4-(n-phenylanilino)phenyl]pyren-1-amine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LGLJXZWEUGZQRX-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- -1 spiroflorene Chemical compound 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- HFRYYTUQIYTHCH-UHFFFAOYSA-N tetrasodium butan-1-olate Chemical compound [O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Na+].[Na+].[Na+].[Na+] HFRYYTUQIYTHCH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- 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
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- 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
-
- 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
- H10K50/15—Hole transporting layers
-
- 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
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a compound for an organic electronic device, an organic electronic device including the same, and a display device including the organic electronic device.
- organic light emitting diodes are composed of a cathode, an anode, and an organic material layer interposed between the cathode and the anode.
- transparent ITO anode hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) and It is formed as a cathode such as LiAl, and if necessary, one or two of the organic layer may be omitted.
- HIL hole injection layer
- HTL hole transport layer
- EL hole blocking layer
- ETL electron transport layer
- EIL electron injection layer
- It is formed as a cathode such as LiAl, and if necessary, one or two of the organic layer may be omitted.
- the method of forming the emission layer is a method of doping phosphorescence (organometal) into a fluorescent host (pure organic material) and a method of doping a fluorescent host with a fluorescent dopant (organic material containing nitrogen, etc.) and a method of implementing a long wavelength using a dopant (DCM, Rubrene, DCJTB, etc.) in the light emitting body. Through such doping, it is attempted to improve the emission wavelength, efficiency, driving voltage, and lifespan.
- materials for forming a light emitting layer are a combination of a central body such as benzene, naphthalene, fluorene, spiroflorene, anthracene, pyrene, and carbazole, ligands such as phenyl, biphenyl, naphthalene and heterocycle, and ortho, meta para, etc. positions and structures in which amine, cyan, fluorine, methyl and trimethyl are substituted.
- An object of the present invention is to provide a compound for an organic electronic device capable of providing improved organic light emitting performance of an asymmetric structure having excellent performance, an organic electronic device including the same, and a display device including the organic electronic device.
- the compound for an organic electronic device according to an embodiment of the present invention is represented by the following formula (1).
- Formula 1 is an asymmetric structure
- R 1 To R 6 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Z 1 To Z 2 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group, and the substituents are optionally fused or linked to form a ring.
- Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is a structure of the following Formulas 1-1 to 1-4, and is an asymmetric structure.
- R 1 To R 12 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 to Y 4 are each independently N or CR 13 .
- R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted It is selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Z 1 to Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 An alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group are selected from among.
- Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is a structure of the following Formulas 2-1 to 2-18, and is an asymmetric structure.
- R 7 To R 13 And R 15 are each independently of each other hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, substituted or unsubstituted a C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C5 to C60 heteroaryl group.
- F fluorine
- CN cyan
- CF 3 trifluoromethyl
- the Y 2 to Y 7 are each independently N or CR 13 .
- the Y 8 and Y 9 are each independently N or CH, and either one is N.
- Z 3 and Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 An alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group are selected from among, wherein Z 3 and Z 4 are optionally fused or linked to form a ring.
- X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is represented by any one of Formulas 3-1 to 3-24 below, and has an asymmetric structure.
- R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, substituted or unsubstituted selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- a display device includes the organic electronic device described above.
- a compound for an organic electronic device excellent in performance by providing the structure of an asymmetric compound of [2,3,4,5-lmn]phenanthridine of 1,6 and 2,7, an organic electronic device containing the same, and an organic A display device including an electronic device may be provided.
- substituted at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted amine group, a nitro group, a substituted or unsubstituted silyl group , C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, C1 to C10 such as trifluoromethyl group It means substituted with a trifluoroalkyl group or a cyano group.
- alkyl group refers to an aliphatic hydrocarbon group unless otherwise defined.
- the alkyl group may be a “saturated alkyl group” that does not contain any double or triple bonds.
- the alkyl group may be a C1 to C20 alkyl group. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
- a C1 to C4 alkyl group means that the alkyl chain contains C1 to C4 carbon atoms, and includes methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl It indicates that it is selected from the group consisting of.
- alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. means, etc.
- alkoxy group is a monovalent group of -OR (R is an alkyl group), which may be linear or branched.
- aryl group refers to a substituent in which all elements of a cyclic substituent have p-orbitals, and these p-orbitals form a conjugate.
- heteroaryl group means that it contains 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, and the remainder is carbon.
- a compound for an organic electronic device represented by the following formula (1):
- Formula 1 is an asymmetric structure
- R 1 To R 6 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Z 1 To Z 2 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group, and the substituents are optionally fused or linked to form a ring.
- Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is represented by any one of Formulas 1-1 to 1-4 below, and has an asymmetric structure.
- R 1 To R 12 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 to Y 4 are each independently N and CR 13 , R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Z 1 to Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Z 1 and Z 2 or Z 3 and Z 4 are optionally fused or linked to form a ring.
- Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is represented by any one of Formulas 2-1 to 2-18 below, and has an asymmetric structure.
- R 7 to R 16 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Y 2 to Y 7 are each independently N and CR 13 , R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 8 and Y 9 are each independently N or CH, and either one is N.
- Z 3 and Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Z 3 and Z 4 are optionally fused or linked to form a ring.
- X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- Formula 1 is represented by any one of Formulas 3-1 to 3-24 below, and has an asymmetric structure.
- R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, substituted or unsubstituted selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
- the Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
- the compound for an organic electronic device according to Formula 1 is represented by any one of the following formulas, the compound for an organic electronic device.
- an organic electronic device including a first electrode, a second electrode, and one or more organic material layers interposed between the first electrode and the second electrode, wherein at least one of the organic material layers is
- An organic electronic device comprising the compound for an organic electronic device of Formula 1 is provided.
- the compound for an organic electronic device may be included in the organic material layer in the form of a single material or a mixture of different materials.
- the term "organic material layer” refers to all layers interposed between the first electrode and the second electrode among organic electronic devices.
- the organic material layer may be a layer having hole properties and a layer having electronic properties.
- the organic material layer is a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron transport function and electron injection It may include one or more of the functional layers having a function at the same time.
- At least one of the hole injection layer, the hole transport layer, and the functional layer having both the hole injection function and the hole transport function is a common hole injection material, a hole transport material, and a material simultaneously performing a hole injection and transport function, and a charge- It may further include a product material.
- the organic material layer may include an emission layer, and the emission layer may include at least one of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant.
- the light emitting layer includes the compound for an organic electronic device, i) the fluorescent host is the compound for an organic electronic device, ii) the fluorescent dopant is the compound for an organic electronic device, iii) the fluorescent host and each fluorescent dopant may be a compound for the organic electronic device.
- the light emitting layer may be a red, green or blue light emitting layer.
- the light emitting layer may be a blue light emitting layer.
- the compound for an organic electronic device may be used as a blue host and/or a blue dopant to provide an organic electronic device having high efficiency, high luminance, high color purity, and a long lifespan.
- the organic material layer may include an electron transport layer, and the compound for an organic electronic device may be included in the electron transport layer.
- the electron transport layer may further include a metal-containing compound in addition to the compound for an organic electronic device.
- the organic material layer includes both a light emitting layer and an electron transport layer, and the compound for an organic electronic device (the compound for an organic electronic device included in the light emitting layer and the electron transport layer may be the same or different from each other) is included in each of the light emitting layer and the electron transport layer may have been
- the organic electronic device may be manufactured by a conventional organic electronic device manufacturing method and material, except for using the organic electronic device compound of Formula 1.
- the organic electronic device may be any one of an organic photoelectric device, an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC), an organic transistor (OTFT), and an organic memory device.
- OLED organic light emitting device
- OSC organic solar cell
- e-Paper electronic paper
- OPC organic photoreceptor
- OFT organic transistor
- organic memory device any one of an organic photoelectric device, an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC), an organic transistor (OTFT), and an organic memory device.
- OLED organic light emitting device
- OSC organic solar cell
- e-Paper electronic paper
- OPC organic photoreceptor
- OFT organic transistor
- OFT organic transistor
- a metal or conductive metal oxide or an alloy thereof is deposited on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. to form an anode, and then an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
- PVD physical vapor deposition
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer.
- the organic material layer is formed using a variety of polymer materials, a solvent process rather than a vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method using a smaller number of layers. can be manufactured with
- the organic light emitting diode according to an exemplary embodiment may be a top emission type, a back emission type, or a double side emission type depending on a material used.
- the compound for an organic electronic device according to an embodiment may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an OLED for lighting, a flexible OLED, an organic photoreceptor, an organic transistor, and the like.
- Reactant 2-0 (20.50g, 42mmol) and hydrazine monohydrate (224 mmol) were put in diethylene glycol (2000mL) in a reaction vessel, stirred at 80 °C for 1 hour, and then refluxed for 1 hour. The resulting mixture was treated with KOH (12 g ) solution and refluxed for 2 hours. The resulting mixture was poured into 1000 mL of water, and the precipitate was filtered, washed 5 times with 500 mL of water and dried. 1-2 (15.71 g, 82%) was obtained. LC-MS measurement: 455.87 (theoretical value: 456.02)
- Example B-1 was prepared by the method of Intermediate A-1.
- a glass substrate coated with a thin film of ITO to a thickness of 1500 ⁇ was placed in distilled water in which Fisher's detergent was dissolved and washed with ultrasonic waves for 30 minutes. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After cleaning with distilled water, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol was used, dried, transferred to a plasma cleaner, and the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
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Abstract
The present invention relates to a compound for an organic electronic device, which is represented by chemical formula 1, an organic electronic device including same, and a display apparatus including the organic electronic device. Specific contents of chemical formula 1 are as defined in the specification.
Description
본 발명은 유기전자소자용 화합물, 이를 포함하는 유기전자소자 및 유기전자소자를 포함하는 표시장치에 관한 것이다.The present invention relates to a compound for an organic electronic device, an organic electronic device including the same, and a display device including the organic electronic device.
일반적으로 유기발광 다이오드(OLED: Organic Light Emitting Diodes)는 음극, 양극, 및 음극과 양극 사이에 개재된 유기물층으로 구성되어 있다. 소자의 구성을 전체적으로 보면 투명 ITO 양극, 정공주입층 (HIL), 정공전달층 (HTL), 발광층 (EL), 정공저지층 (HBL), 전자전달층 (ETL), 전자주입층 (EIL) 및 LiAl 등의 음극으로 형성되며, 필요에 따라 유기물층의 1~2 개를 생략하는 경우도 있다. 구성된 양 전극 사이에 전계가 인가되면 음극 측으로 부터 전자가 주입되고 양극 측으로 부터 정공이 주입된다. In general, organic light emitting diodes (OLEDs: Organic Light Emitting Diodes) are composed of a cathode, an anode, and an organic material layer interposed between the cathode and the anode. Looking at the structure of the device as a whole, transparent ITO anode, hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) and It is formed as a cathode such as LiAl, and if necessary, one or two of the organic layer may be omitted. When an electric field is applied between the configured positive electrodes, electrons are injected from the negative side and holes are injected from the positive side.
또한, 이 전자가 발광층에 정공과 재결합하여 여기상태를 생성하고, 여기상태가 기저상태로 되돌아갈 때에 에너지를 빛으로서 방출한다. 이러한 발광 재료는 크게 형광과 인광으로 나뉘며, 발광층 형성방법은 형광 호스트(순수 유기물)에 인광(유기금속)을 도핑하는 방법과 형광 호스트에 형광 도판트(질소 등을 포함하는 유기물)를 도핑하는 방법 및 발광체에 도판트 (DCM, Rubrene, DCJTB 등)를 이용하여 장파장을 구현하는 방법 등이 있다. 이러한 도핑을 통해 발광 파장, 효율, 구동전압 및 수명 등을 개선하려 하고 있다. 일반적으로 발광층 형성용 재료들은 벤젠, 나프탈렌, 플로렌, 스파이로플로렌, 안트라센, 파이렌 및 카바졸 등의 중심체와 페닐, 바이페닐, 나프탈렌 및 헤테로사이클 등의 리간드 그리고 오르소, 메타 파라 등의 결합 위치 및 아민, 시안, 불소, 메틸 및 트리메틸 등이 치환된 구조들을 갖는다.In addition, these electrons recombine with holes in the light emitting layer to generate an excited state, and when the excited state returns to the ground state, energy is emitted as light. These luminescent materials are largely divided into fluorescence and phosphorescence, and the method of forming the emission layer is a method of doping phosphorescence (organometal) into a fluorescent host (pure organic material) and a method of doping a fluorescent host with a fluorescent dopant (organic material containing nitrogen, etc.) and a method of implementing a long wavelength using a dopant (DCM, Rubrene, DCJTB, etc.) in the light emitting body. Through such doping, it is attempted to improve the emission wavelength, efficiency, driving voltage, and lifespan. In general, materials for forming a light emitting layer are a combination of a central body such as benzene, naphthalene, fluorene, spiroflorene, anthracene, pyrene, and carbazole, ligands such as phenyl, biphenyl, naphthalene and heterocycle, and ortho, meta para, etc. positions and structures in which amine, cyan, fluorine, methyl and trimethyl are substituted.
현재 디스플레이의 화면이 대형화 방향으로 진행되면서 고성능의 발광 재료들이 요구되고 있다. 또한 발광파장의 색 좌표 이외에, 소자의 낮은 구동전압에서 높은 발광효율 및 재료의 화학 구조적 열 안정성인 높은 유리전이온도에 대한 특성 향상이 요구되고 있다.Currently, as the screen of the display progresses in the direction of enlargement, high-performance light emitting materials are required. In addition to the color coordinates of the emission wavelength, there is a demand for high luminous efficiency at a low driving voltage of the device and to improve the properties for a high glass transition temperature, which is the chemical structural thermal stability of the material.
본 발명은, 성능이 우수한 비대칭형 구조의 유기발광 성능 향상을 제공할 수 있는 유기전자소자용 화합물, 이를 포함하는 유기전자소자 및 유기전자소자를 포함하는 표시장치를 제공함에 있다. An object of the present invention is to provide a compound for an organic electronic device capable of providing improved organic light emitting performance of an asymmetric structure having excellent performance, an organic electronic device including the same, and a display device including the organic electronic device.
또한, 본 발명이 해결하고자 하는 기술적 과제는 이상에서 언급한 기술적 과제로 제한되지 않으며, 언급되지 않은 또 다른 기술적 과제들은 아래의 기재로부터 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자에게 명확하게 이해될 수 있을 것이다.In addition, the technical problem to be solved by the present invention is not limited to the technical problem mentioned above, and other technical problems not mentioned are clearly to those of ordinary skill in the art to which the present invention belongs from the description below. can be understood
본 발명의 구현예에 따른 유기전자소자용 화합물은 하기 화학식 1로 표시된다. The compound for an organic electronic device according to an embodiment of the present invention is represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1은 비대칭형 구조이며,Formula 1 is an asymmetric structure,
상기 R1 내지 R6은 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 1 To R 6 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y2는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Z1 내지 Z2는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되고, 치환기는 임의로 융합 또는 연결되어 고리를 형성한다.The Z 1 To Z 2 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group, and the substituents are optionally fused or linked to form a ring.
상기 Ar1은 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C6 내지 C40 아미노아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 1-1 내지 1-4의 구조이며, 비대칭 구조이다.Formula 1 is a structure of the following Formulas 1-1 to 1-4, and is an asymmetric structure.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
상기 화학식 1-1 내지 화학식 1-4의 구조는 비대칭형 구조이며,The structures of Formulas 1-1 to 1-4 are asymmetric structures,
상기 R1 내지 R12는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 1 To R 12 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y4는 각각 서로 독립적으로 N 또는 C-R13이다. R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 to Y 4 are each independently N or CR 13 . R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted It is selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Z1 내지 Z4는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기이며 중에서 선택된다.The Z 1 to Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 An alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group are selected from among.
상기 Ar1은 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C6 내지 C40 아미노아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 2-1 내지 2-18의 구조이며, 비대칭 구조이다.Formula 1 is a structure of the following Formulas 2-1 to 2-18, and is an asymmetric structure.
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
[화학식 2-4][Formula 2-4]
[화학식 2-5][Formula 2-5]
[화학식 2-6][Formula 2-6]
[화학식 2-7][Formula 2-7]
[화학식 2-8][Formula 2-8]
[화학식 2-9][Formula 2-9]
[화학식 2-10][Formula 2-10]
[화학식 2-11][Formula 2-11]
[화학식 2-12][Formula 2-12]
[화학식 2-13][Formula 2-13]
[화학식 2-14][Formula 2-14]
[화학식 2-15][Formula 2-15]
[화학식 2-16][Formula 2-16]
[화학식 2-17][Formula 2-17]
[화학식 2-18][Formula 2-18]
상기 R7 내지 R13는 및 R15는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기이다.Wherein R 7 To R 13 And R 15 Are each independently of each other hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, substituted or unsubstituted a C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y2 내지 Y7은 각각 서로 독립적으로 N 또는 C-R13이다.The Y 2 to Y 7 are each independently N or CR 13 .
상기 Y8와 Y9는 각각 서로 독립적으로 N 또는 C-H이며, 어느 하나는 N이다.The Y 8 and Y 9 are each independently N or CH, and either one is N.
상기 Z3과 Z4는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기이며 중에서 선택되고, 상기 Z3과 Z4는 임의로 융합 또는 연결되어 고리를 형성한다.wherein Z 3 and Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 An alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group are selected from among, wherein Z 3 and Z 4 are optionally fused or linked to form a ring.
상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 3-1 내지 3-24 중 어느 하나로 표시되고, 비대칭 구조이다.Formula 1 is represented by any one of Formulas 3-1 to 3-24 below, and has an asymmetric structure.
[화학식 3-1][Formula 3-1]
[화학식 3-2][Formula 3-2]
[화학식 3-3][Formula 3-3]
[화학식 3-4][Formula 3-4]
[화학식 3-5][Formula 3-5]
[화학식 3-6][Formula 3-6]
[화학식 3-7][Formula 3-7]
[화학식 3-8][Formula 3-8]
[화학식 3-9][Formula 3-9]
[화학식 3-10][Formula 3-10]
[화학식 3-11][Formula 3-11]
[화학식 3-12][Formula 3-12]
[화학식 3-13][Formula 3-13]
[화학식 3-14][Formula 3-14]
[화학식 3-15][Formula 3-15]
[화학식 3-16][Formula 3-16]
[화학식 3-17][Formula 3-17]
[화학식 3-18][Formula 3-18]
[화학식 3-19][Formula 3-19]
[화학식 3-20][Formula 3-20]
[화학식 3-21][Formula 3-21]
[화학식 3-22][Formula 3-22]
[화학식 3-23][Formula 3-23]
[화학식 3-24][Formula 3-24]
상기 R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, substituted or unsubstituted selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y2는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
본 발명의 또 다른 구현예에 따른 표시장치는 전술한 유기전자소자를 포함한다. A display device according to another embodiment of the present invention includes the organic electronic device described above.
본 발명에 의하면, 1,6과 2,7의 [2,3,4,5-lmn]phenanthridine의 비대칭 화합물의 구조를 제공하여 성능이 우수한 유기전자소자용 화합물, 이를 포함하는 유기전자소자 및 유기전자소자를 포함하는 표시장치를 제공할 수 있다. According to the present invention, a compound for an organic electronic device excellent in performance by providing the structure of an asymmetric compound of [2,3,4,5-lmn]phenanthridine of 1,6 and 2,7, an organic electronic device containing the same, and an organic A display device including an electronic device may be provided.
이하, 첨부된 도면을 참조하여 본 발명의 실시예들을 상세하게 설명하면 다음과 같다. 다만, 본 기재를 설명함에 있어서, 이미 공지된 기능 혹은 구성에 대한 설명은, 본 기재의 요지를 명료하게 하기 위하여 생략하기로 한다.Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. However, in describing the present description, descriptions of already known functions or configurations will be omitted in order to clarify the gist of the present description.
본 명세서에서 "치환"이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 할로겐기, 히드록시기, 아미노기, 치환 또는 비치환된 아민기, 니트로기, 치환 또는 비치환된 실릴기, C1 내지 C30의 알킬기, C1 내지 C10의 알킬실릴기, C3 내지 C30의 시클로알킬기, C6 내지 C30의 아릴기, C1 내지 C20의 알콕시기, 플루오로기, 트리플루오로메틸기 등의 C1 내지 C10의 트리플루오로알킬기 또는 시아노기로 치환된 것을 의미한다.In the present specification, unless otherwise defined as "substituted", at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted amine group, a nitro group, a substituted or unsubstituted silyl group , C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, C1 to C10 such as trifluoromethyl group It means substituted with a trifluoroalkyl group or a cyano group.
또한 상기 치환된 할로겐기, 히드록시기, 아미노기, 치환 또는 비치환된 아민기, 니트로기, 치환 또는 비치환된 실릴기, C1 내지 C30의 알킬기, C1 내지 C10의 알킬실릴기, C3 내지 C30의 시클로알킬기, C6 내지 C30의 아릴기, C1 내지 C20의 알콕시기, 플루오로기, 트리플루오로메틸기 등의 C1 내지 C10의 트리플루오로알킬기 또는 시아노기 중 인접한 두 개의 치환기가 융합되어 고리를 형성할 수도 있다. In addition, the substituted halogen group, hydroxyl group, amino group, substituted or unsubstituted amine group, nitro group, substituted or unsubstituted silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group , C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, such as C1 to C10 trifluoroalkyl group or cyano group, two adjacent substituents may be fused to form a ring .
본 명세서에서 "알킬(alkyl)기"이란 별도의 정의가 없는 한, 지방족 탄화수소기를 의미한다. 알킬기는 어떠한 이중결합이나 삼중결합을 포함하고 있지 않은 "포화 알킬(saturated alkyl)기"일 수 있다.As used herein, the term “alkyl group” refers to an aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a “saturated alkyl group” that does not contain any double or triple bonds.
알킬기는 C1 내지 C20인 알킬기일 수 있다. 보다 구체적으로 알킬기는 C1 내지 C10인 알킬기 또는 C1 내지 C6인 알킬기일 수도 있다. 예를 들어, C1 내지 C4인 알킬기는 알킬쇄에 C1 내지 C4 개의 탄소원자가 포함되는 것을 의미하며, 메틸, 에틸, 프로필, 이소-프로필, n-부틸, 이소-부틸, sec-부틸 및 t-부틸로 이루어진 군에서 선택됨을 나타낸다.The alkyl group may be a C1 to C20 alkyl group. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group means that the alkyl chain contains C1 to C4 carbon atoms, and includes methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl It indicates that it is selected from the group consisting of.
상기 알킬기는 구체적인 예를 들어 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, t-부틸기, 펜틸기, 헥실기, 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기 등을 의미한다.Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. means, etc.
본 명세서에서， "알콕시기"는 -OR (R은 알킬기)인 1가 그룹으로서， 이는 직쇄상 또는 분지쇄상일 수 있다.In the present specification, "alkoxy group" is a monovalent group of -OR (R is an alkyl group), which may be linear or branched.
본 명세서에 있어서, "아릴(aryl)기"는 환형인 치환기의 모든 원소가 p-오비탈을 가지고 있으며, 이들 p-오비탈이 공액(conjugation)을 형성하고 있는 치환기를 의미한다.As used herein, the term "aryl group" refers to a substituent in which all elements of a cyclic substituent have p-orbitals, and these p-orbitals form a conjugate.
본 명세서에 있어서, "헤테로아릴(heteroaryl)기"는 아릴기 내에 N, O, S 및 P로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 4개 함유하고, 나머지는 탄소인 것을 의미한다.In the present specification, "heteroaryl group" means that it contains 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, and the remainder is carbon.
본 발명의 일 구현예에 따라, 하기 화학식 1로 표시되는 유기전자소자용 화합물이 제공된다. According to one embodiment of the present invention, there is provided a compound for an organic electronic device represented by the following formula (1).
하기 화학식 1로 표시되는 유기전자소자용 화합물:A compound for an organic electronic device represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1은 비대칭형 구조이며,Formula 1 is an asymmetric structure,
상기 R1 내지 R6은 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 1 To R 6 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y2는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Z1 내지 Z2는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되고, 치환기는 임의로 융합 또는 연결되어 고리를 형성한다.The Z 1 To Z 2 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group, and the substituents are optionally fused or linked to form a ring.
상기 Ar1은 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C6 내지 C40 아미노아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 1-1 내지 1-4중 어느 하나로 표시되고, 비대칭 구조이다.Formula 1 is represented by any one of Formulas 1-1 to 1-4 below, and has an asymmetric structure.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
상기 화학식 1-1 내지 화학식 1-4의 구조는 비대칭형 구조이며,The structures of Formulas 1-1 to 1-4 are asymmetric structures,
상기 R1 내지 R12는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 1 To R 12 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y4는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 to Y 4 are each independently N and CR 13 , R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Z1 내지 Z4는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다. 상기 Z1과 Z2 또는 Z3 과 Z4는 임의로 융합 또는 연결되어 고리를 형성한다.The Z 1 to Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group. The Z 1 and Z 2 or Z 3 and Z 4 are optionally fused or linked to form a ring.
상기 Ar1은 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C6 내지 C40 아미노아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Ar 1 is selected from a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C6 to C40 aminoaryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 2-1 내지 2-18중 어느 하나로 표시되고, 비대칭 구조이다.Formula 1 is represented by any one of Formulas 2-1 to 2-18 below, and has an asymmetric structure.
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
[화학식 2-4][Formula 2-4]
[화학식 2-5][Formula 2-5]
[화학식 2-6][Formula 2-6]
[화학식 2-7][Formula 2-7]
[화학식 2-8][Formula 2-8]
[화학식 2-9][Formula 2-9]
[화학식 2-10][Formula 2-10]
[화학식 2-11][Formula 2-11]
[화학식 2-12][Formula 2-12]
[화학식 2-13][Formula 2-13]
[화학식 2-14][Formula 2-14]
[화학식 2-15][Formula 2-15]
[화학식 2-16][Formula 2-16]
[화학식 2-17][Formula 2-17]
[화학식 2-18][Formula 2-18]
상기 R7 내지 R16는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.wherein R 7 to R 16 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y2 내지 Y7은 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.wherein Y 2 to Y 7 are each independently N and CR 13 , R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y8와 Y9는 각각 서로 독립적으로 N 또는 C-H이며, 어느 하나는 N이다.The Y 8 and Y 9 are each independently N or CH, and either one is N.
상기 Z3과 Z4는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다. Z3과 Z4는 임의로 융합 또는 연결되어 고리를 형성한다.wherein Z 3 and Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 It is selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group. Z 3 and Z 4 are optionally fused or linked to form a ring.
상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1은 하기의 화학식 3-1 내지 3-24중 어느 하나로 표시되고, 비대칭 구조이다.Formula 1 is represented by any one of Formulas 3-1 to 3-24 below, and has an asymmetric structure.
[화학식 3-1][Formula 3-1]
[화학식 3-2][Formula 3-2]
[화학식 3-3][Formula 3-3]
[화학식 3-4][Formula 3-4]
[화학식 3-5][Formula 3-5]
[화학식 3-6][Formula 3-6]
[화학식 3-7][Formula 3-7]
[화학식 3-8][Formula 3-8]
[화학식 3-9][Formula 3-9]
[화학식 3-10][Formula 3-10]
[화학식 3-11][Formula 3-11]
[화학식 3-12][Formula 3-12]
[화학식 3-13][Formula 3-13]
[화학식 3-14][Formula 3-14]
[화학식 3-15][Formula 3-15]
[화학식 3-16][Formula 3-16]
[화학식 3-17][Formula 3-17]
[화학식 3-18][Formula 3-18]
[화학식 3-19][Formula 3-19]
[화학식 3-20][Formula 3-20]
[화학식 3-21][Formula 3-21]
[화학식 3-22][Formula 3-22]
[화학식 3-23][Formula 3-23]
[화학식 3-24][Formula 3-24]
상기 R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, substituted or unsubstituted selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 Y1 내지 Y2는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.The Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group.
상기 화학식 1에 따른 유기전자소자용 화합물은 하기 화학식 중 어느 하나로 표시되는, 유기전자소자용 화합물.The compound for an organic electronic device according to Formula 1 is represented by any one of the following formulas, the compound for an organic electronic device.
본 발명의 다른 일 구현예에 따르면, 제1 전극, 제2 전극 및 상기 제1 전극 및 상기 제2 전극 사이에 개재되는 하나 이상의 유기물층을 포함하는 유기전자소자로서, 상기 유기물층 중 하나 이상은 전술한 상기 화학식 1의 유기전자소자용 화합물을 포함하는 유기전자소자가 제공된다.According to another embodiment of the present invention, an organic electronic device including a first electrode, a second electrode, and one or more organic material layers interposed between the first electrode and the second electrode, wherein at least one of the organic material layers is An organic electronic device comprising the compound for an organic electronic device of Formula 1 is provided.
상기 유기전자소자용 화합물은 단일 물질 또는 서로 다른 물질의 혼합물의 형태로 상기 유기물층에 포함될 수 있다. The compound for an organic electronic device may be included in the organic material layer in the form of a single material or a mixture of different materials.
본 명세서 중 "유기물층"은 유기전자소자 중 제1전극과 제2전극 사이에 개재된 모든 층을 가리키는 용어이다. 상기 유기물층은 정공 특성을 가지는 층 및 전자 특성을 가지는 층일 수 있다. 예를 들어, 상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층, 전자 저지층, 발광층, 정공 저지층, 전자 수송층, 전자 주입층 및 전자 수송 기능 및 전자 주입 기능을 동시에 갖는 기능층 중 하나 이상을 포함할 수 있다. In the present specification, the term "organic material layer" refers to all layers interposed between the first electrode and the second electrode among organic electronic devices. The organic material layer may be a layer having hole properties and a layer having electronic properties. For example, the organic material layer is a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron transport function and electron injection It may include one or more of the functional layers having a function at the same time.
상기 정공 주입층, 상기 정공 수송층 및 상기 정공 주입 기능 및 정공 수송 기능을 동시에 갖는 기능층 중 적어도 하나는, 통상의 정공 주입 물질, 정공 수송 물질 및 정공 주입 및 수송 기능을 동시에 하는 물질 외에, 전하-생성 물질을 더 포함할 수 있다.At least one of the hole injection layer, the hole transport layer, and the functional layer having both the hole injection function and the hole transport function is a common hole injection material, a hole transport material, and a material simultaneously performing a hole injection and transport function, and a charge- It may further include a product material.
예를 들어, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광 호스트, 형광 호스트, 인광 도판트 및 형광 도판트 중 하나 이상을 포함할 수 있다. 여기서, 상기 발광층에 상기 유기전자소자용 화합물이 포함되어 있고, i) 상기 형광 호스트가 상기 유기전자소자용 화합물이거나, ii) 상기 형광 도판트가 상기 유기전자소자용 화합물이거나, iii) 상기 형광 호스트 및 형광 도판트 각각이 상기 유기전자소자용 화합물일 수 있다.For example, the organic material layer may include an emission layer, and the emission layer may include at least one of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. Here, the light emitting layer includes the compound for an organic electronic device, i) the fluorescent host is the compound for an organic electronic device, ii) the fluorescent dopant is the compound for an organic electronic device, iii) the fluorescent host and each fluorescent dopant may be a compound for the organic electronic device.
상기 발광층은 적색, 녹색 또는 청색 발광층일 수 있다. 예를 들어, 상기 발광층은 청색 발광층일 수 있다. 이 때, 상기 유기전자소자용 화합물은 청색 호스트 및/또는 청색 도펀트로 사용되어, 고효율, 고휘도, 고색순도, 및 장수명을 갖는 유기전자소자를 제공할 수 있다.The light emitting layer may be a red, green or blue light emitting layer. For example, the light emitting layer may be a blue light emitting layer. In this case, the compound for an organic electronic device may be used as a blue host and/or a blue dopant to provide an organic electronic device having high efficiency, high luminance, high color purity, and a long lifespan.
또한, 상기 유기물층은 전자 수송층을 포함하고, 상기 전자 수송층에 상기 유기전자소자용 화합물이 포함될 수 있다. 여기서, 상기 전자 수송층은 상기 유기전자소자용 화합물 외에, 금속-함유 화합물을 더 포함할 수 있다.In addition, the organic material layer may include an electron transport layer, and the compound for an organic electronic device may be included in the electron transport layer. Here, the electron transport layer may further include a metal-containing compound in addition to the compound for an organic electronic device.
상기 유기물층은 발광층 및 전자 수송층을 모두 포함하고, 상기 발광층 및 전자 수송층 각각에 상기 유기전자소자용 화합물(발광층 및 전자 수송층에 포함된 상기 유기전자소자용 화합물은 서로 동일하거나 상이할 수 있음)가 포함되어 있을 수 있다. The organic material layer includes both a light emitting layer and an electron transport layer, and the compound for an organic electronic device (the compound for an organic electronic device included in the light emitting layer and the electron transport layer may be the same or different from each other) is included in each of the light emitting layer and the electron transport layer may have been
상기 유기전자소자는 화학식 1의 유기전자소자용 화합물을 이용하는 것을 제외하고는, 통상의 유기전자소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic electronic device may be manufactured by a conventional organic electronic device manufacturing method and material, except for using the organic electronic device compound of Formula 1.
상기 유기전자소자는 유기광전소자, 유기발광소자 (OLED), 유기태양전지 (OSC), 전자종이 (e-Paper), 유기감광체(OPC), 유기트랜지스터 (OTFT) 및 유기메모리소자 중 어느 하나일 수 있다. The organic electronic device may be any one of an organic photoelectric device, an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC), an organic transistor (OTFT), and an organic memory device. can
일 예로, 상기 유기발광소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공전달층, 발광층, 정공저지층 및 전자전달층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기물층은 정공주입층, 정공전달층, 발광층, 정공저지층 및 전자전달층 등을 포함하는 다층 구조일 수도 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.For example, in the organic light emitting device, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. to form an anode, and then an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer. In addition, the organic material layer is formed using a variety of polymer materials, a solvent process rather than a vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method using a smaller number of layers. can be manufactured with
일 구현예에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다. 일 구현예에 따른 유기전자소자용 화합물은 유기태양전지, 조명용 OLED, Flexible OLED, 유기감광체, 유기트랜지스터 등을 비롯한 유기전자소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다. The organic light emitting diode according to an exemplary embodiment may be a top emission type, a back emission type, or a double side emission type depending on a material used. The compound for an organic electronic device according to an embodiment may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an OLED for lighting, a flexible OLED, an organic photoreceptor, an organic transistor, and the like.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다. Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples are only provided for easier understanding of the present invention, and thus the content of the present invention is not limited thereto.
또한, 본 발명의 각 실시예에서 제조방법이 구체적으로 개시되지 않은 화합물은 당업계에 통상적인 방법으로 제조하거나 또는 다른 실시예에 기재된 제조방법을 참고하여 제조함을 이해한다.In addition, it is understood that the compound for which the preparation method is not specifically disclosed in each Example of the present invention is prepared by a conventional method in the art or is prepared by referring to the preparation method described in other Examples.
<중간체의 제조> <Preparation of intermediate>
* 중간체 5,10-benzo[lmn][2,7]phenanthroline (1-1)의 제조 * Preparation of intermediate 5,10-benzo[lmn][2,7]phenanthroline (1-1)
반응물 1-0 (9.92g42mmol) 및 히드라진일수화물(Hydrazine monohydrate 224 mmol)을 디에틸렌글리콜(Diethylene glycol 2000mL)에 넣고 80℃에서 1시간 동안 교반 한 다음, 1시간 동안 환류 시켰다. 생성된 혼합물을 실온에서 KOH (12g)용액으로 처리한 후, 2 시간 동안 환류하였다. 생성된 혼합물을 1000 mL의 물에 붓고 침전물을 여과하고, 물 500 mL로 5 회 세척 후 건조시켰다. 수율(7.2g, 85 %) 및 녹색 고체를 얻었다. LC-MS 측정치:204.08 (이론적 값:204.23)The reactant 1-0 (9.92g42mmol) and hydrazine monohydrate (224 mmol) were put in diethylene glycol (2000mL), stirred at 80°C for 1 hour, and then refluxed for 1 hour. The resulting mixture was treated with KOH (12 g) solution at room temperature, and then refluxed for 2 hours. The resulting mixture was poured into 1000 mL of water, and the precipitate was filtered, washed 5 times with 500 mL of water and dried. Yield (7.2 g, 85 %) and a green solid was obtained. LC-MS measured: 204.08 (theoretical value: 204.23)
* 중간체 2,7-diiodo5,10-benzo[lmn][2,7]phenanthroline (1-2)의 제조 * Preparation of intermediate 2,7-diiodo5,10-benzo[lmn][2,7]phenanthroline (1-2)
반응 용기에 반응물 2-0 (20.50g ,42mmol) 및 히드라진일수화물(Hydrazine monohydrate 224 mmol)을 디에틸렌 글리콜(Diethylene glycol 2000mL)에 넣고 80 ℃에서 1시간 동안 교반 한 다음, 1 시간 동안 환류시켰다. 생성된 혼합물을 KOH (12g )용액으로 처리하고, 2 시간 동안 환류 하였다. 생성된 혼합물을 1000 mL의 물에 붓고 침전물을 여과한 후, 물 500 mL로 5 회 세척하고, 건조시켰다. 1-2(15.71g, 82 %)을 획득하였다. LC-MS 측정치:455.87 (이론적값:456.02)Reactant 2-0 (20.50g, 42mmol) and hydrazine monohydrate (224 mmol) were put in diethylene glycol (2000mL) in a reaction vessel, stirred at 80 °C for 1 hour, and then refluxed for 1 hour. The resulting mixture was treated with KOH (12 g ) solution and refluxed for 2 hours. The resulting mixture was poured into 1000 mL of water, and the precipitate was filtered, washed 5 times with 500 mL of water and dried. 1-2 (15.71 g, 82%) was obtained. LC-MS measurement: 455.87 (theoretical value: 456.02)
* 중간체 1,6-dibromo5,10-benzo[lmn][2,7]phenanthroline (1-3)의 제조* Preparation of intermediate 1,6-dibromo5,10-benzo[lmn][2,7]phenanthroline (1-3)
반응 용기에 1-1(14.30g,70mmol), 메탄올(20mL), 에틸에테르(20mL), 과산화수소(2.40g,1eq), 브롬화수소(26.52g, 1.2eq)을 넣고 상온에서 12시간 반응시켰다. 반응이 종료후 탄산수소나트륨용액으로 반응물질을 중화시키고, 클로로메탄용액으로 유기물질을 추출 후 1-3물질(24.07,95%)획득하였다. LC-MS 측정치:359.89 (이론적값:362.02)1-1 (14.30 g, 70 mmol), methanol (20 mL), ethyl ether (20 mL), hydrogen peroxide (2.40 g, 1 eq), and hydrogen bromide (26.52 g, 1.2 eq) were placed in a reaction vessel and reacted at room temperature for 12 hours. After the reaction was completed, the reaction material was neutralized with sodium hydrogen carbonate solution, and organic material was extracted with chloromethane solution, and then 1-3 materials (24.07,95%) were obtained. LC-MS measurement:359.89 (theoretical value:362.02)
* 중간체 7-iodo-N,N-diphenylpyrido[2,3,4,5-lmn]phenanthridin-2-amine (A-1)의 제조* Preparation of intermediate 7-iodo-N,N-diphenylpyrido[2,3,4,5-lmn]phenanthridin-2-amine (A-1)
반응 용기에 3-0 물질(200.2g, 75mmol), 나트륨테트라부톡시드 （21.62g，225mmol）, 툴루렌（500mL）, 다이아민（12.69g，75mmol）, Pd2(dba)3(2.06g, 2.25mmol) 및 트리테트라부틸 포스핀 （0.36mL，15mmol）을 넣고 110 ℃에서 1시간 반응하였다. 반응 용액을 냉각시키고, 물로 씻은 후, 실리카 필터로 팔라듐 촉매를 제거한 다음 증발 건조시킨 후, 메틸렌 클로라이드 / 석유 에테르로 재결정하여 A-1 (14.92g, 40 %)얻었다. LC-MS 측정치:497.05 (이론적 값:497.33)3-0 substance (200.2 g, 75 mmol), sodium tetrabutoxide (21.62 g, 225 mmol), toluene (500 mL), diamine (12.69 g, 75 mmol), Pd2 (dba) 3 (2.06 g, 2.25) in a reaction vessel mmol) and tritetrabutyl phosphine (0.36 mL, 15 mmol) were added and reacted at 110 °C for 1 hour. The reaction solution was cooled, washed with water, the palladium catalyst was removed with a silica filter, evaporated to dryness, and recrystallized from methylene chloride / petroleum ether to obtain A-1 (14.92 g, 40%). LC-MS measured:497.05 (theoretical value:497.33)
* 중간체 A-2 내지 A-80의 제조* Preparation of intermediates A-2 to A-80
상기 중간체 A-1의 제조 방법으로 하기 [표 1]의 화합물을 얻었다.The compound of Table 1 below was obtained by the preparation method of Intermediate A-1.
* 중간체 4-(7-bromopyren-2-yl)-N,N-diphenylaniline (A-81)의 제조* Preparation of intermediate 4-(7-bromopyren-2-yl)-N,N-diphenylaniline (A-81)
반응용기에 2,7-diiodopyrido[2,3,4,5-lmn]phenanthridine 물질(205.21g, 450 mmol), N- (4- 브로 모 페닐) -N- 페닐 아닐린 (183.00 g, 450 mmol), 테트라 키스 (트리 페닐 포스 핀) 팔라듐 (0) (26 g, 22.5 mmol) 5ℓ들이 3 구 플라스크에 탄산 칼륨 (2.2M, 640mL, 1405mmol), 톨루엔 (2200mL), 에탄올 (500mL) 및 물 (500mL)을 넣고 15 시간 동안 가열하였다. 혼합물을 냉각시키고, 여과하고, 분리하고, 톨루엔 층을 건조시켜 황색 오일을 수득 하였다. 소량의 디클로로 메탄을 가하여 용해시키고, 적절한 양의 석유 에테르를 첨가하여 고체 A-81을 침전시켰다 (수율: 167.92 g, 65 %). 생성된 화합물을 LC-MS로 분석하였다. 실험값 m/z: 573.44 (이론 값574.07)In a reaction vessel, 2,7-diiodopyrido [2,3,4,5-lmn] phenanthridine substance (205.21 g, 450 mmol), N- (4-bromophenyl) -N-phenylaniline (183.00 g, 450 mmol) , tetrakis (triphenylphosphine) palladium (0) (26 g, 22.5 mmol) potassium carbonate (2.2M, 640mL, 1405mmol), toluene (2200mL), ethanol (500mL) and water (500mL) in a 5-liter 3-neck flask ) and heated for 15 hours. The mixture was cooled, filtered, separated and the toluene layer dried to give a yellow oil. A small amount of dichloromethane was added to dissolve, and an appropriate amount of petroleum ether was added to precipitate solid A-81 (yield: 167.92 g, 65%). The resulting compound was analyzed by LC-MS. Experimental value m/z: 573.44 (theoretical value 574.07)
* 중간체 A-82 내지 A-91의 제조* Preparation of intermediates A-82 to A-91
상기 중간체 A-81의 제조 방법으로 하기 [표 2]의 화합물을 얻었다.The compound shown in Table 2 below was obtained by the preparation method of Intermediate A-81.
* 실시예 4,4'-((7-(diphenylamino)pyrido[2,3,4,5-lmn]phenanthridin-2-yl)azanediyl)dibenzonitrile (B-1)의 제조* Preparation of Example 4,4'-((7-(diphenylamino)pyrido[2,3,4,5-lmn]phenanthridin-2-yl)azanediyl)dibenzonitrile (B-1)
상기 중간체 A-1의 방법으로 실시예 B-1을 제조하였다.Example B-1 was prepared by the method of Intermediate A-1.
* 실시예 B-13 내지 B-107의 제조* Preparation of Examples B-13 to B-107
상기 중간체 A-1의 제조 방법으로 하기 [표 3]의 화합물을 얻었다.The compound of Table 3 below was obtained by the preparation method of Intermediate A-1.
* 실시예 C-13 내지 C-87의 제조* Preparation of Examples C-13 to C-87
상기 중간체 A-1의 제조 방법으로 하기 [표 4]의 화합물을 얻었다.The compound of Table 4 below was obtained by the preparation method of Intermediate A-1.
ITO가 1500Å의 두께로 박막 코팅된 유리 기판을 피셔사의 세제를 녹인 2차 증류수에 넣고 초음파로 30분간 세척하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척하고 건조시킨 후, 플라즈마 세정기로 이송시켜, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 이송시켰다.A glass substrate coated with a thin film of ITO to a thickness of 1500 Å was placed in distilled water in which Fisher's detergent was dissolved and washed with ultrasonic waves for 30 minutes. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After cleaning with distilled water, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol was used, dried, transferred to a plasma cleaner, and the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine)를 500Å 진공증착 후, 정공전달층으로 a-NPD (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) 300Å 진공 증착한 후, AND (9,10-Di(2-naphthyl)anthracene)과 도판트 DPAP-DPPA (6-(4-(diphenylamino)phenyl)-N,N-diphenylpyren-1-amine) 또는 표 3과 4에 기재된 대로 실시예의 물질을 5% 도핑하여 300Å의 두께로 진공 증착하였으며, 정공저지층 및 정공전달층으로 TPBi (1,3,5-tris(N-phenylbenzimidizol-2-yl)benzene) 물질을 400Å의 두께로 진공증착 하였으며, 순차적으로 LiF 5Å과 Al(알루미늄) 2000Å 증착하여 음극을 형성하였다. 상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였고, LiF는 0.2 Å/sec, 알루미늄은 3~7Å/sec의 증착속도를 유지하였다.After vacuum deposition of 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a hole injection layer on the prepared ITO transparent electrode 500Å, a-NPD (N, N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) 300Å vacuum deposition, AND (9,10-Di(2-naphthyl) ) anthracene) and dopant DPAP-DPPA (6-(4-(diphenylamino)phenyl)-N,N-diphenylpyren-1-amine) or the materials of Examples as described in Tables 3 and 4 were doped with 5% to a thickness of 300 Å TPBi (1,3,5-tris(N-phenylbenzimidizol-2-yl)benzene) material was vacuum-deposited to a thickness of 400 Å as a hole blocking layer and a hole transport layer, and LiF 5 Å and Al ( Aluminum) was deposited at 2000 Å to form a cathode, and in the above process, the deposition rate of organic material was maintained at 1 Å/sec, LiF at 0.2 Å/sec, and aluminum at 3-7 Å/sec.
상기에서 제조된 유기 발광 소자에 대한 전기적 발광특성을 하기 [표 5]에 나타내었다.The electroluminescence characteristics of the organic light emitting device prepared above are shown in [Table 5] below.
상기 표 5의 결과로부터, 본 발명에 따른 유기전자소자용 화합물은 청색의 역할에서 발광 효율 및 수명 특성이 향상됨을 확인할 수 있었다. From the results of Table 5, it was confirmed that the compound for an organic electronic device according to the present invention improved luminous efficiency and lifespan characteristics in the role of blue.
이상에서와 같이, 본 기재에 의하면, 비대칭형 구조의 구조를 제공하여 성능이 우수한 유기전자소자용 화합물, 이를 포함하는 유기전자소자 및 유기전자소자를 포함하는 표시장치를 제공할 수 있다. As described above, according to the present description, it is possible to provide a compound for an organic electronic device excellent in performance by providing an asymmetric structure, an organic electronic device including the same, and a display device including the organic electronic device.
앞에서, 본 발명의 특정한 실시예가 설명되고 도시되었지만 본 발명은 기재된 실시예에 한정되는 것이 아니고, 본 발명의 사상 및 범위를 벗어나지 않고 다양하게 수정 및 변형할 수 있음은 이 기술의 분야에서 통상의 지식을 가진 자에게 자명한 일이다. 따라서, 그러한 수정예 또는 변형예들은 본 발명의 기술적 사상이나 관점으로부터 개별적으로 이해되어서는 안되며, 변형된 실시예들은 본 발명의 특허청구범위에 속한다 하여야 할 것이다.In the foregoing, specific embodiments of the present invention have been described and illustrated, but it is common knowledge in the art that the present invention is not limited to the described embodiments, and that various modifications and variations can be made without departing from the spirit and scope of the present invention. It is self-evident to those who have Accordingly, such modifications or variations should not be individually understood from the technical spirit or point of view of the present invention, and the modified embodiments should belong to the claims of the present invention.
Claims (7)
- 하기의 화학식 2-1 내지 2-12, 화학식 2-15 내지 2-18, 화학식 3-11 및 화학식 3-23으로 이루어진 군에서 선택된 어느 하나인 비대칭 구조를 갖는 화합물:A compound having an asymmetric structure selected from the group consisting of Formulas 2-1 to 2-12, Formulas 2-15 to 2-18, Formulas 3-11, and Formula 3-23:[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
[화학식 2-3][Formula 2-3]
[화학식 2-4][Formula 2-4]
[화학식 2-5][Formula 2-5]
[화학식 2-6][Formula 2-6]
[화학식 2-7][Formula 2-7]
[화학식 2-8][Formula 2-8]
[화학식 2-9][Formula 2-9]
[화학식 2-10][Formula 2-10]
[화학식 2-11][Formula 2-11]
[화학식 2-12][Formula 2-12]
[화학식 2-15][Formula 2-15]
[화학식 2-16][Formula 2-16]
[화학식 2-17][Formula 2-17]
[화학식 2-18][Formula 2-18]
[화학식 3-11][Formula 3-11]
[화학식 3-23][Formula 3-23]
상기 R7 내지 R16는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되고,wherein R 7 to R 16 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 selected from an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group,상기 Y3내지 Y7은 각각 서로 독립적으로 N 또는 C-R13이며,The Y 3 to Y 7 are each independently N or CR 13 ,상기 Y8와 Y9는 각각 서로 독립적으로 N 또는 C-H이며, 어느 하나는 N 이고,The Y 8 and Y 9 are each independently N or CH, any one is N,상기 Z3과 Z4는 각각 서로 독립적으로 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되고, 상기 Z3과 Z4는 임의로 융합 또는 연결되어 고리를 형성하며,wherein Z 3 and Z 4 are each independently hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 an alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group, wherein Z 3 and Z 4 are optionally fused or linked to form a ring;상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택될 수 있다.Wherein X is a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group It may be selected from there is. - 제1항에 있어서, According to claim 1,상기 화학식 2-1 내지 2-12, 화학식 2-15 내지 2-18은 하기 화학식 3-1 내지 3-10, 화학식 3-12 내지 3-22 및 화학식 3-24 중 어느 하나로 표시되며, 비대칭 구조를 갖는 화합물:Formulas 2-1 to 2-12 and Formulas 2-15 to 2-18 are represented by any one of Formulas 3-1 to 3-10, Formulas 3-12 to 3-22, and Formula 3-24, and an asymmetric structure A compound having:[화학식 3-1][Formula 3-1]
[화학식 3-2][Formula 3-2]
[화학식 3-3][Formula 3-3]
[화학식 3-4][Formula 3-4]
[화학식 3-5][Formula 3-5]
[화학식 3-6][Formula 3-6]
[화학식 3-7][Formula 3-7]
[화학식 3-8][Formula 3-8]
[화학식 3-9][Formula 3-9]
[화학식 3-10][Formula 3-10]
[화학식 3-12][Formula 3-12]
[화학식 3-13][Formula 3-13]
[화학식 3-14][Formula 3-14]
[화학식 3-15][Formula 3-15]
[화학식 3-16][Formula 3-16]
[화학식 3-17][Formula 3-17]
[화학식 3-18][Formula 3-18]
[화학식 3-19][Formula 3-19]
[화학식 3-20][Formula 3-20]
[화학식 3-21][Formula 3-21]
[화학식 3-22][Formula 3-22]
[화학식 3-24][Formula 3-24]
상기 R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되고,Wherein R 13 is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, substituted or unsubstituted selected from a C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group,상기 Y1 내지 Y2는 각각 서로 독립적으로 N 및 C-R13이며, R13은 수소, 불소(F), 시안(CN), 트리플로오로메틸(CF3), 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택되며,The Y 1 To Y 2 are each independently N and CR 13 , R 13 Is hydrogen, fluorine (F), cyan (CN), trifluoromethyl (CF 3 ), a substituted or unsubstituted C1 to C60 alkyl group , a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, a substituted or unsubstituted C5 to C60 heteroaryl group,상기 X는 치환 또는 비치환된 C1 내지 C60 알킬기, 치환 또는 비치환된 C1 내지 C60 알콕시기, 치환 또는 비치환된 C6 내지 C40 아릴기, 치환 또는 비치환된 C5 내지 C60 헤테로아릴기 중에서 선택된다.Wherein X is selected from a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C40 aryl group, and a substituted or unsubstituted C5 to C60 heteroaryl group. - 제2항에 있어서,3. The method of claim 2,상기 유기전자소자용 화합물은 하기 화학식으로 이루어진 군에서 선택된 어느 하나로 표시되는, 유기전자소자용 화합물. The compound for an organic electronic device is represented by any one selected from the group consisting of the following formula, the compound for an organic electronic device.
- 제1 전극, 제2 전극 및 상기 제1 전극과 상기 제2 전극 사이에 개재되는 하나 이상의 유기물층을 포함하는 유기전자소자에 있어서,An organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer interposed between the first electrode and the second electrode,상기 유기물층은 상기 제1항 내지 제3항 중 어느 한 항에 따른 유기전자소자용 화합물을 하나 이상 포함하는, 유기전자소자.The organic material layer comprises at least one compound for an organic electronic device according to any one of claims 1 to 3, an organic electronic device.
- 제4항에 있어서, 5. The method of claim 4,상기 유기물층은 발광층, 정공수송층, 정공주입층, 전자수송층, 전자주입층, 정공저지층 및 이들의 조합으로 이루어진 군에서 선택된 어느 하나인, 유기전자소자. The organic material layer is any one selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and combinations thereof, an organic electronic device.
- 제4항에 있어서, 5. The method of claim 4,상기 유기전자소자는, The organic electronic device,유기광전소자, 유기발광소자, 유기태양전지, 유기트랜지스터, 유기 감광체, 전자종이 및 유기메모리소자로 이루어진 군에서 선택되는 어느 하나인, 유기전자소자. An organic electronic device, which is any one selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor, an electronic paper, and an organic memory device.
- 제4항에 따른 유기전자소자를 포함하는 표시장치.A display device comprising the organic electronic device according to claim 4 .
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| KR20160076303A (en) * | 2014-12-22 | 2016-06-30 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting diode comprising the same |
| CN110256428A (en) * | 2019-06-28 | 2019-09-20 | 上海天马有机发光显示技术有限公司 | A kind of compound, OLED display panel, display device |
| KR20200050675A (en) * | 2018-11-02 | 2020-05-12 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
| CN111662258A (en) * | 2019-03-08 | 2020-09-15 | 江苏三月光电科技有限公司 | Organic compound containing pyrene and application thereof in OLED |
| KR102201028B1 (en) * | 2020-10-23 | 2021-01-11 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
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| KR20160076303A (en) * | 2014-12-22 | 2016-06-30 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting diode comprising the same |
| KR20200050675A (en) * | 2018-11-02 | 2020-05-12 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
| CN111662258A (en) * | 2019-03-08 | 2020-09-15 | 江苏三月光电科技有限公司 | Organic compound containing pyrene and application thereof in OLED |
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| KR102201028B1 (en) * | 2020-10-23 | 2021-01-11 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
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