KR20230013803A - Polycyclic compound and organic light emitting device using the same - Google Patents
Polycyclic compound and organic light emitting device using the same Download PDFInfo
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- KR20230013803A KR20230013803A KR1020210094717A KR20210094717A KR20230013803A KR 20230013803 A KR20230013803 A KR 20230013803A KR 1020210094717 A KR1020210094717 A KR 1020210094717A KR 20210094717 A KR20210094717 A KR 20210094717A KR 20230013803 A KR20230013803 A KR 20230013803A
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- carbon atoms
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- -1 Polycyclic compound Chemical class 0.000 title claims abstract description 74
- 239000012044 organic layer Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 75
- 239000010410 layer Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000003367 polycyclic group Chemical group 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 3
- 230000003190 augmentative effect Effects 0.000 claims 1
- 238000005137 deposition process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000005264 aryl amine group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 6
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 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 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BVRDQVRQVGRNHG-UHFFFAOYSA-N 2-morpholin-4-ylpyrimido[2,1-a]isoquinolin-4-one Chemical compound N1=C2C3=CC=CC=C3C=CN2C(=O)C=C1N1CCOCC1 BVRDQVRQVGRNHG-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KESRRRLHHXXBRW-UHFFFAOYSA-N C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 Chemical compound C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 KESRRRLHHXXBRW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H01L51/008—
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- H01L51/5024—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 다환 고리 화합물 및 이를 이용하여 발광 효율이 현저하게 향상된 고효율 유기발광소자에 관한 것이다.The present invention relates to a polycyclic compound and a high-efficiency organic light-emitting device having remarkably improved luminous efficiency using the same.
유기발광소자는 전자 주입 전극 (캐소드 전극)으로부터 주입된 전자 (electron)와 정공 주입 전극 (애노드 전극)으로부터 주입된 정공 (hole)이 발광층에서 결합하여 엑시톤 (exiton)을 형성하고 그 엑시톤이 에너지를 방출하면서 발광하는 자체 발광형 소자이며, 이와 같은 유기발광소자는 낮은 구동 전압, 높은 휘도, 넓은 시야각 및 빠른 응답속도를 가지며 풀-컬러 평판 발광 디스플레이에 적용 가능하다는 이점 때문에 차세대 광원으로서 각광을 받고 있다.In the organic light emitting device, electrons injected from the electron injection electrode (cathode electrode) and holes injected from the hole injection electrode (anode electrode) are combined in the light emitting layer to form excitons, and the excitons generate energy. It is a self-luminous device that emits light while emitting, and such an organic light emitting device has a low driving voltage, high luminance, wide viewing angle, and fast response speed, and is in the limelight as a next-generation light source due to the advantages of being applicable to full-color flat light emitting displays. .
이러한 유기발광소자가 상기와 같은 특징을 발휘하기 위해서는 소자 내 유기층의 구조를 최적화하고, 각 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광물질, 전자수송 물질, 전자주입 물질, 전자저지 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 여전히 안정하고 효율적인 유기발광소자용 유기층의 구조 및 각 재료의 개발이 계속하여 필요한 실정이다.In order for such an organic light emitting device to exhibit the above characteristics, the structure of the organic layer in the device is optimized, and materials constituting each organic layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and an electron blocking material Although it should be preceded that the etc. be supported by stable and efficient materials, there is still a need to develop a stable and efficient structure of an organic layer for an organic light emitting device and each material.
이와 같이 유기발광소자의 발광 특성을 개선할 수 있는 소자의 구조와 이를 뒷받침하는 새로운 재료에 대한 개발이 계속 요구되고 있는 실정이다.In this way, there is a continuing demand for the development of a device structure capable of improving the light emitting characteristics of an organic light emitting device and a new material supporting it.
따라서, 본 발명은 유기층에 채용되어 고효율 및 저전압 구동 특성을 갖는 소자를 구현할 수 있는 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Accordingly, an object of the present invention is to provide a compound capable of implementing a device having high efficiency and low voltage driving characteristics by being employed in an organic layer, and an organic light emitting device including the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 A] 또는 [화학식 B]로 표시되는 다환 고리 화합물을 제공한다.In order to solve the above problems, the present invention provides a polycyclic compound represented by the following [Formula A] or [Formula B].
[화학식 A] [화학식 B][Formula A] [Formula B]
상기 [화학식 A] 또는 [화학식 B]의 구조 및 이에 따라 구현되는 구체적인 화합물과, Q1 내지 Q2 고리, X1 내지 X3, Y 및 R1 내지 R6의 정의에 대해서는 후술하기로 한다.The structure of [Formula A] or [Formula B] and the specific compound implemented accordingly, and definitions of Q 1 to Q 2 rings, X 1 to X 3 , Y and R 1 to R 6 will be described later.
또한, 본 발명은 제1 전극, 상기 제1 전극에 대향된 제2 전극 및 상기 제1 전극과 제2 전극 사이에 개재된 유기층을 포함하고, 상기 유기층이 상기 [화학식 A] 또는 [화학식 B]로 구현되는 구체적인 다환 고리 화합물을 1 종 이상 포함하는 유기발광소자를 제공한다.In addition, the present invention includes a first electrode, a second electrode opposed to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is the [Formula A] or [Formula B] It provides an organic light emitting device comprising at least one kind of specific polycyclic ring compound implemented as.
본 발명에 따른 다환 고리 화합물을 소자 내 유기층에 채용하여 저전압 구동 특성과 발광 효율이 현저히 향상된 고효율의 유기발광소자를 구현할 수 있다.By employing the polycyclic compound according to the present invention in an organic layer in a device, a high-efficiency organic light-emitting device with significantly improved low-voltage driving characteristics and luminous efficiency can be realized.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 하기 [화학식 A] 또는 [화학식 B]로 표시되는 다환 고리 화합물에 관한 것이며, 이를 통하여 저전압 구동 특성과 발광 효율이 현저히 향상된 고효율의 유기발광소자를 구현할 수 있다.The present invention relates to a polycyclic compound represented by the following [Formula A] or [Formula B], and through this, a high-efficiency organic light emitting device with significantly improved low-voltage driving characteristics and luminous efficiency can be implemented.
[화학식 A] [화학식 B][Formula A] [Formula B]
상기 [화학식 A] 또는 [화학식 B]에서,In [Formula A] or [Formula B],
Y는 B, P=O, P=S 또는 Al이다.Y is B, P = O, P = S or Al.
X1 내지 X3는 각각 독립적으로 NR7, O, S, CR8R9 또는 SiR10R11이다.X 1 to X 3 are each independently NR 7 , O, S, CR 8 R 9 or SiR 10 R 11 .
Q1 및 Q2는 각각 독립적으로 치환 또는 비치환된 탄소수 5 내지 50의 방향족 탄화수소 고리, 치환 또는 비치환된 탄소수 2 내지 50의 방향족 헤테로고리, 치환 또는 비치환된 탄소수 3 내지 30의 지방족 고리 및 치환 또는 비치환된 탄소수 3 내지 30의 지방족 방향족 혼합 고리 중 선택된다.Q 1 and Q 2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and It is selected from substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms.
상기 R1 내지 R11은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택된다.R 1 to R 11 are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom. Cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted It is selected from an unsubstituted silyl group, a substituted or unsubstituted C3-C20 aliphatic aromatic mixed ring group, a nitro group, a cyano group, and a halogen group.
상기 R1 및 R2는 인접한 치환기와 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있고, 상기 R7 내지 R11은 Q1 또는 Q2와 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있으며, 상기 R3와 R4 및 R5와 R6는 각각 서로 연결되어 치환 또는 비치환된 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있다.The R 1 and R 2 may be linked to adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring, and R 7 to R 11 may be linked to Q 1 or Q 2 to form an alicyclic or aromatic ring. A monocyclic or polycyclic ring may be further formed, and R 3 and R 4 and R 5 and R 6 may be connected to each other to further form a substituted or unsubstituted alicyclic or aromatic monocyclic or polycyclic ring. can
본 발명의 일 실시예에 의하면, 상기 [화학식 A]는 하기 [화학식 A-1]으로 표시되는 다환 고리 화합물일 수 있다.According to one embodiment of the present invention, [Formula A] may be a polycyclic compound represented by the following [Formula A-1].
[화학식 A-1][Formula A-1]
상기 [화학식 A-1]에서,In the above [Formula A-1],
R은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택되며, X1, X3, Q1, Q2 및 R1의 정의는 상기 [화학식 A]에서 정의한 바와 동일하다.R are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted It is selected from an aliphatic aromatic mixed ring group having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group, and the definitions of X 1 , X 3 , Q 1 , Q 2 and R 1 are the same as defined in [Formula A] above. .
본 발명의 일 실시예에 의하면, 상기 [화학식 B]는 하기 [화학식 B-1] 또는 [화학식 B-2]로 표시되는 다환 고리 화합물일 수 있다.According to one embodiment of the present invention, [Formula B] may be a polycyclic compound represented by the following [Formula B-1] or [Formula B-2].
[화학식 B-1] [화학식 B-2][Formula B-1] [Formula B-2]
상기 [화학식 B-1] 및 [화학식 B-2]에서, In [Formula B-1] and [Formula B-2],
R은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택되며, X1 및 X2, R1 내지 R4 및 Q2의 정의는 상기 [화학식 B]에서 정의한 바와 동일하다.R are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted It is selected from an aliphatic aromatic mixed ring group having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group, and the definitions of X 1 and X 2 , R 1 to R 4 and Q 2 are the same as defined in [Formula B] .
본 발명의 일 실시예에 의하면, 상기 [화학식 A] 또는 [화학식 B]에서 Y는 B이고, R1 및 R2는 각각 치환 또는 비치환된 탄소수 6 내지 30의 아릴기인 것을 특징으로 한다.According to one embodiment of the present invention, in [Formula A] or [Formula B], Y is B, and R 1 and R 2 are each a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
한편, 본 발명에서 '치환 또는 비치환된'이라는 용어는 Q1, Q2, R 및 R1 내지 R11 등이 각각 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 아미노기, 알킬기, 사이클로알킬기, 할로겐화된 알킬기, 알케닐기, 알키닐기, 헤테로알킬기, 헤테로사이클로알킬기, 아릴기, 아릴알킬기, 헤테로아릴기, 헤테로아릴알킬기, 알콕시기, 알킬아민기, 아릴아민기, 헤테로아릴아민기, 알킬실릴기, 아릴실릴기, 아릴옥시기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.Meanwhile, in the present invention, the term 'substituted or unsubstituted' means that Q 1 , Q 2 , R and R 1 to R 11 are deuterium, cyano group, halogen group, hydroxyl group, nitro group, amino group, alkyl group, cycloalkyl group, respectively. , Halogenated alkyl group, alkenyl group, alkynyl group, heteroalkyl group, heterocycloalkyl group, aryl group, arylalkyl group, heteroaryl group, heteroarylalkyl group, alkoxy group, alkylamine group, arylamine group, heteroarylamine group, alkylsilyl It means that it is substituted with one or two or more substituents selected from the group consisting of a group, an arylsilyl group, and an aryloxy group, is substituted with a substituent in which two or more substituents are connected, or does not have any substituent.
또한, 상기 '치환 또는 비치환된 탄소수 1 내지 30의 알킬기', '치환 또는 비치환된 탄소수 6 내지 50의 아릴기' 등에서의 상기 알킬기 또는 아릴기의 탄소수 범위는 상기 치환기가 치환된 부분을 고려하지 않고 비치환된 것으로 보았을 때의 알킬 부분 또는 아릴 부분을 구성하는 전체 탄소수를 의미하는 것이다. 예컨대, 파라위치에 부틸기가 치환된 페닐기는 탄소수 4의 부틸기로 치환된 탄소수 6의 아릴기에 해당하는 것을 의미한다.In addition, the carbon number range of the alkyl or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 50 carbon atoms', etc., considers the part where the substituent is substituted It means the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted without being unsubstituted. For example, a phenyl group in which a butyl group is substituted at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
또한, 본 발명에 있어서 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지환족, 방향족 고리를 형성할 수 있는 것을 의미하며, '인접하는 치환기'는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체 구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘 (ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 '인접하는 치환기'로 해석될 수 있다.In addition, in the present invention, the meaning of forming a ring by combining with adjacent groups means that a substituted or unsubstituted alicyclic or aromatic ring can be formed by combining with adjacent groups, and 'adjacent substituents' refer to the corresponding It may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as 'adjacent substituents'.
본 발명에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be a straight chain or branched chain, and specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1- Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group , cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1 -Ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited to these.
본 발명에 있어서, 알케닐기는 직쇄 또는 분지쇄를 포함하며, 다른 치환기에 의하여 추가로 치환될 수 있고, 구체적으로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present invention, the alkenyl group includes a straight chain or branched chain, and may be further substituted by other substituents, specifically, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, and a 2-butene group. Nyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group , 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl -1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto.
본 발명에 있어서, 알키닐기 역시 직쇄 또는 분지쇄를 포함하며, 다른 치환기에 의하여 추가로 치환될 수 있고, 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, the alkynyl group also includes a straight chain or branched chain, and may be further substituted by other substituents, and may include ethynyl, 2-propynyl, etc., but is limited thereto It doesn't work.
본 발명에 있어서, 방향족 탄화수소 고리 또는 아릴기는 단환식 또는 다환식일 수 있고, 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오란텐기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of the polycyclic aryl group include a naphthyl group , Anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacennyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention It is not limited to only these examples.
본 발명에 있어서, 방향족 헤테로고리 또는 헤테로아릴기는 헤테로원자 중 1개 이상을 포함하는 방향족 고리로서, 그 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one of hetero atoms, examples of which include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, and an oxadia group. sol group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group , pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group , Dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc. However, it is not limited to these.
본 발명에 있어서, 지방족 탄화수소 고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미하고, 그 예로서 단환 또는 다환을 포함하며, 다른 치환기에 의하여 추가로 치환될 수 있고, 다환이란 다른 고리기와 직접 연결되거나 축합된 기를 의미하는 것으로서, 다른 고리기란 지방족 탄화수소 고리일 수도 있으나, 다른 종류의 고리기, 예컨대 지방족 헤테로고리, 아릴기, 헤테로아릴기 등일 수도 있다. 구체적으로, 시클로프로필기, 시클로부틸기, 시클로펜틸기, 아다만틸기, 3-메틸시클로펜틸기, 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등의 시클로알킬, 그리고 시클로헥세인, 시클로펜테인 등의 시클로알케인, 그리고 시클로헥센, 시클로뷰텐 등의 시클로시클로알켄을 포함하며, 이에 한정되는 것은 아니다.In the present invention, an aliphatic hydrocarbon ring is a non-aromatic ring and means a ring composed of only carbon and hydrogen atoms, and includes monocyclic or polycyclic as an example, and may be further substituted by other substituents, and polycyclic means other This means a group directly connected to or condensed with a ring group, and other ring groups may be aliphatic hydrocarbon rings, but may also be other types of ring groups, such as aliphatic heterocycles, aryl groups, and heteroaryl groups. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, adamantyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclo Cycloalkyl such as hexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and cyclohexane, cyclohexyl group cycloalkanes such as pentane, and cyclocycloalkenes such as cyclohexene and cyclobutene, but are not limited thereto.
본 발명에 있어서 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족고리를 의미하고, O, S, Se, N 또는 Si 등의 이종원자를 포함하는 것으로서, 역시 단환 또는 다환을 포함하며, 다른 치환기에 의하여 추가로 치환될 수 있고, 다환이란 헤테로시클로알킬, 헤테로시클알케인, 헤테로시클로알겐기 등이 다른 고리기와 직접 연결되거나 축합된 기를 의미하는 것으로서, 다른 고리기란 지방족헤테로고리일 수도 있으나, 다른 종류의 고리기, 예컨대 지방족 탄화수소 고리, 아릴기, 헤테로아릴기 등일 수도 있다.In the present invention, an aliphatic heterocycle means an aliphatic ring containing at least one of heteroatoms, and includes a heteroatom such as O, S, Se, N, or Si, and also includes a monocyclic or polycyclic ring, and other substituents It may be further substituted by, and polycyclic refers to a group in which a heterocycloalkyl, heterocycloalkane, heterocycloalgen group, etc. is directly connected or condensed with another ring group, and the other ring group may be an aliphatic heterocyclic ring, Other types of ring groups such as aliphatic hydrocarbon rings, aryl groups, heteroaryl groups, and the like may also be used.
본 발명에 있어서, 지방족 방향족 혼합고리는 2 이상의 고리가 서로 축합되어 있고, 분자 전체가 비방향족성 (non-aromacity)를 갖는 고리를 의미하며, 또한 다환의 비방향족 축합 헤테로고리는 축합 비방향족 탄화수소고리에서 C 외에 N, O, P 및 S 중에서 선택된 헤테로 원자를 포함하는 것을 의미한다.In the present invention, the aliphatic aromatic mixed ring means a ring in which two or more rings are condensed with each other and the entire molecule has non-aromaticity, and the polycyclic non-aromatic condensed heterocycle is a condensed non-aromatic hydrocarbon. In addition to C, a heteroatom selected from N, O, P and S is included in the ring.
본 발명에 있어서, 알콕시기는 구체적으로 메톡시, 에톡시, 프로폭시, 이소부틸옥시, sec-부틸옥시, 펜틸옥시, iso-아밀옥시, 헥실옥시 등일 수 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited thereto.
본 발명에 있어서, 실릴기는 -SiH3, 알킬실릴기, 아릴실릴기, 알킬아릴실릴기, 아릴헤테로아릴실릴기 등일 수 있고, 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있다.In the present invention, the silyl group may be -SiH 3 , an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, and the like, and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, Trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc. are mentioned.
본 발명에 있어서, 아민기는 -NH2, 알킬아민기, 아릴아민기, 아릴헤테로아릴아민기 등일 수 있고, 아릴아민기는 아릴로 치환된 아민을 의미하고, 알킬아민기는 알킬로 치환된 아민을 의미하는 것이며, 아릴헤테로아릴아민기는 아릴 및 헤테로아릴기로 치환된 아민을 의미하는 것으로서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있고, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기 및 헤테로아릴기는 단환식 아릴기, 단환식 헤테로아릴기일 수 있고, 다환식 아릴기, 다환식 헤테로아릴기일 수 있으며, 상기 아릴기, 헤테로아릴기를 2 이상을 포함하는 아릴아민기, 아릴헤테로아릴아민기는 단환식 아릴기(헤테로아릴기), 다환식 아릴기(헤테로아릴기), 또는 단환식 아릴기(헤테로아릴기)와 다환식 아릴기(헤테로아릴기)를 동시에 포함할 수 있다. 또한, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기, 헤테로아릴기는 전술한 아릴기, 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present invention, the amine group may be -NH 2 , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., the arylamine group refers to an amine substituted with an aryl, and the alkylamine group refers to an amine substituted with an alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted diarylamine group. There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a monocyclic heteroaryl group, or may be a polycyclic aryl group or a polycyclic heteroaryl group. In addition, the aryl group and heteroaryl group including two or more arylamine groups and arylheteroarylamine groups are monocyclic aryl groups (heteroaryl groups), polycyclic aryl groups (heteroaryl groups), or monocyclic aryl groups (heteroaryl groups). aryl group) and polycyclic aryl group (heteroaryl group) may be included at the same time. In addition, the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the aryl group and heteroaryl group described above.
본 발명에 있어서, 아릴옥시기, 아릴티옥시기 중의 아릴기는 전술한 아릴기의 예시와 같으며, 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, p-tert-부틸페녹시기, 3-바이페닐옥시기, 4-바이페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으나, 이에 한정되는 것은 아니다.In the present invention, the aryl group in the aryloxy group and arylthioxy group is the same as the above-mentioned aryl group, and specifically, the aryloxy group includes a phenoxy group, p-toryloxy group, m-toryloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenane There is a triloxy group, 9-phenanthryloxy group, and the like, and arylthioxy groups include, but are not limited to, phenylthioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group, and the like.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.
보다 구체적으로 본 발명에 따른 [화학식 A] 또는 [화학식 B]로 표시되는 다환 고리 화합물은 하기 화합물 중에서 선택되는 어느 하나일 수 있으며, 이를 통하여 [화학식 A] 또는 [화학식 B]의 구조 및 구체적인 치환기를 명확하게 확인할 수 있으며, 다만, 이에 의해서 본 발명에 따른 [화학식 A] 또는 [화학식 B]의 범위가 한정되는 것은 아니다.More specifically, the polycyclic compound represented by [Formula A] or [Formula B] according to the present invention may be any one selected from the following compounds, through which the structure and specific substituents of [Formula A] or [Formula B] Can be clearly identified, however, this does not limit the scope of [Formula A] or [Formula B] according to the present invention.
상기 구체적인 화합물에서 확인할 수 있는 바와 같이, 본 발명에 따르면 보론(B) 등을 포함하면서 특징적 구조의 다환 고리를 형성하고, 여기에 특징적 치환기를 도입하여 그 치환기의 고유 특성을 갖는 유기발광소자용 재료를 합성하여 각 유기층에서 요구하는 조건들을 충족시키는 물질, 바람직하게는 발광층에 채용되는 물질을 제조할 수 있으며, 이를 통하여 고효율의 유기발광소자를 구현할 수 있다.As can be seen in the above specific compounds, according to the present invention, a polycyclic ring having a characteristic structure is formed while containing boron (B), etc., and a characteristic substituent is introduced therein, thereby providing a material for an organic light emitting device having inherent characteristics of the substituent. It is possible to manufacture a material that satisfies the conditions required by each organic layer, preferably a material used in the light emitting layer, through which a highly efficient organic light emitting device can be implemented.
본 발명의 다른 일 측면은 제1 전극, 제2 전극 및 상기 제1 전극 및 제2 전극 사이에 개재되는 1층 이상의 유기층으로 이루어진 유기발광소자에 관한 것으로서, 상기 유기층에 상기 [화학식 A] 또는 [화학식 B]로 표시되는 본 발명에 따른 다환 고리 화합물을 최소한 1 개 이상 포함할 수 있다.Another aspect of the present invention relates to an organic light emitting device composed of a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the [Formula A] or [Formula A] or [ Formula B] may include at least one polycyclic compound according to the present invention.
즉, 본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 [화학식 A] 또는 [화학식 B]의 다환 고리 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자의 제조 방법 및 재료를 사용하여 제조될 수 있다.That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween, [Formula A] or [Formula B] according to the present invention It can be manufactured using conventional device manufacturing methods and materials, except that the polycyclic ring compound of is used in the organic layer of the device.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공주입층, 정공수송층, 정공저지층, 발광층, 전자저지층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기층을 포함할 수도 있으며, 본 발명에 따른 바람직한 유기발광소자의 유기층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like. However, it is not limited thereto and may include a smaller or larger number of organic layers, and an organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in the embodiments to be described later.
본 발명에 따른 유기발광소자는 애노드, 정공수송층, 발광층, 전자수송층 및 캐소드을 포함하며, 필요에 따라서는 애노드와 정공수송층 사이에 정공주입층을 더 포함할 수 있고, 또한 전자수송층과 캐소드 사이에 전자주입층을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.The organic light emitting device according to the present invention includes an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, and may further include a hole injection layer between the anode and the hole transport layer, if necessary, and electron transport layer between the electron transport layer and the cathode. An injection layer may be further included, and in addition to that, it is possible to further form one or two intermediate layers, and a hole blocking layer or an electron blocking layer may be further formed.
본 발명의 바람직한 일 실시예로서, 본 발명은 상기 제1 전극과 제2 전극 사이에 개재된 유기층이 발광층을 포함하며, 상기 발광층은 호스트와 도판트로 이루어지고, 본 발명에 따른 상기 [화학식 A] 또는 [화학식 B]로 표시되는 다환 고리 화합물을 발광층 내 도판트로 포함할 수 있다.As a preferred embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is made of a host and a dopant, and the [Formula A] according to the present invention Alternatively, a polycyclic compound represented by [Formula B] may be included as a dopant in the light emitting layer.
한편, 본 발명의 일 실시예에 따른 유기발광소자의 구체적인 구조, 그 제조방법 및 각 유기층 재료에 대하여 살펴보면 다음과 같다.Meanwhile, a detailed structure of an organic light emitting device according to an embodiment of the present invention, a manufacturing method thereof, and materials for each organic layer are as follows.
먼저 기판 상부에 애노드 전극용 물질을 코팅하여 애노드를 형성한다. 여기에서 기판으로는 통상적인 유기발광소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급 용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석 (ITO), 산화인듐아연 (IZO), 산화주석 (SnO2), 산화아연 (ZnO) 등을 사용한다.First, an anode is formed by coating a material for an anode electrode on a substrate. Here, as the substrate, a substrate used in a conventional organic light emitting device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance is preferable. In addition, as materials for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.
상기 애노드 전극 상부에 정공주입층 물질을 진공 열증착 또는 스핀 코팅하여 정공주입층을 형성하고, 그 다음으로 상기 정공주입층의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층을 형성한다.A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on top of the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on top of the hole injection layer. .
상기 정공주입층 재료는 당업계에서 통상적으로 사용되는 것이라면, 특별히 제한되지 않고 사용할 수 있으며, 구체적인 예시로서, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine] HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] 등을 사용할 수 있다.As long as the hole injection layer material is commonly used in the art, it may be used without particular limitation, and as a specific example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] and the like can be used.
또한, 상기 정공수송층 재료 역시 당업계에 통상적으로 사용되는 것이라면, 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민 (TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐벤지딘 (α-NPD) 등을 사용할 수 있다.In addition, the hole transport layer material is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1- Biphenyl] -4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) or the like can be used.
이어서, 상기 정공수송층의 상부에 정공보조층 및 발광층을 이어서 적층하고 상기 발광층의 상부에 선택적으로 정공저지층을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.Subsequently, a hole auxiliary layer and a light emitting layer may be sequentially stacked on top of the hole transport layer, and a hole blocking layer may be selectively formed on top of the light emitting layer by a vacuum deposition method or a spin coating method. The hole-blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the organic light emitting layer and flow into the cathode. . At this time, the hole-blocking material used is not particularly limited, but should have electron transport ability and higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, and the like may be used.
상기 정공저지층에 사용되는 물질로서, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq 및 [화학식 501] 내지 [화학식 507] 중에서 선택되는 어느 하나가 사용될 수 있으나, 이에 한정되는 것은 아니다.As a material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq, and [Formula 501] to [Formula 507] may be used, but is limited thereto it is not going to be
BAlq BCP BphenBAlq BCP Bphen
TPBI NTAZ BeBq2 TPBI NTAZ BeBq 2
OXD-7 LiqOXD-7 Liq
[화학식 501] [화학식 502] [화학식 503][Formula 501] [Formula 502] [Formula 503]
[화학식 504] [화학식 505] [화학식 506][Formula 504] [Formula 505] [Formula 506]
[화학식 507][Formula 507]
이러한 정공저지층 위에 전자수송층을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층을 형성하고 상기 전자주입층의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드 전극을 형성함으로써 본 발명의 일 실시예에 따른 유기발광소자가 완성된다.The present invention by forming an electron injection layer after depositing an electron transport layer on the hole blocking layer through a vacuum deposition method or a spin coating method, and vacuum thermally depositing a metal for forming a cathode on top of the electron injection layer to form a cathode electrode. An organic light emitting device according to an embodiment of is completed.
여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.Here, the metal for forming the cathode is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.
상기 전자수송층 재료로는 캐소드로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서, 공지의 전자 수송 물질을 이용할 수 있다. 공지의 전자 수송 물질의 예로는, 퀴놀린 유도체, 특히 트리스(8-퀴놀리노레이트)알루미늄(Alq3), TAZ, BAlq, 베릴륨 비스(벤조퀴놀리-10-노에이트)(beryllium bis(benzoquinolin-10-olate: Bebq2), [화학식 401], [화학식 402], 옥사디아졸 유도체인 PBD, BMD, BND 등과 같은 재료를 사용할 수도 있다.As the material for the electron transport layer, a known electron transport material may be used to stably transport electrons injected from the cathode. Examples of known electron transport materials are quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10- olate: Bebq2), [Formula 401], [Formula 402], oxadiazole derivatives such as PBD, BMD, and BND may be used.
TAZ BAlqTAZ BAlq
[화합물 401] [화합물 402] BCP[Compound 401] [Compound 402] BCP
또한, 상기 유기층 각각은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 여기서 상기 증착 방식은 상기 각각의 층을 형성하기 위한 재료로 사용되는 물질을 진공 또는 저압상태에서 가열 등을 통해 증발시켜 박막을 형성하는 방법을 의미하고, 상기 용액공정은 상기 각각의 층을 형성하기 위한 재료로 사용되는 물질을 용매와 혼합하고 이를 잉크젯 인쇄, 롤투롤 코팅, 스크린 인쇄, 스프레이 코팅, 딥 코팅, 스핀 코팅 등과 같은 방법을 통하여 박막을 형성하는 방법을 의미한다.In addition, each of the organic layers may be formed by a single molecule deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process mixes a material used as a material for forming each layer with a solvent, and inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating. It means a method of forming a thin film through the same method.
또한, 본 발명에 따른 유기발광소자는 평판 디스플레이 장치, 플렉시블 디스플레이 장치, 단색 또는 백색의 평판 조명용 장치 및 단색 또는 백색의 플렉시블 조명용 장치에서 선택되는 장치에 사용될 수 있다.In addition, the organic light emitting diode according to the present invention may be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.
합성예synthesis example 1 : [ One : [ 1]의1] 합성 synthesis
합성예synthesis example 1-1 : 중간체 A-1의 합성 1-1: Synthesis of Intermediate A-1
<A-1a> <A-1b> <A-1><A-1a> <A-1b> <A-1>
반응기에 <A-1a> 100.0 g, <중간체 A-1b> 76.6 g, 테트라키스팔라듐(0) 12.1 g, 포타슘카보네이트 144.7 g, 톨루엔 500 mL, 에탄올 300 mL, 물 300 mL를 넣고 18시간 동안 환류 교반하였다. 상온으로 냉각한 다음, 아세테이트산에틸과 물을 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 A-1>을 얻었다. (72.3 g, 73.4%)100.0 g of <A-1a>, 76.6 g of <Intermediate A-1b>, 12.1 g of tetrakispalladium (0), 144.7 g of potassium carbonate, 500 mL of toluene, 300 mL of ethanol, and 300 mL of water were added to the reactor and refluxed for 18 hours. Stir. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate A-1>. (72.3 g, 73.4%)
합성예synthesis example 1-2 : 중간체 A-2의 합성 1-2: Synthesis of Intermediate A-2
<A-1> <A-2a> <A-2><A-1> <A-2a> <A-2>
반응기에 <A-1> 70.0 g, <A-2a> 192.1 g, 에탄올 616 mL 넣고 교반한다. 반응온도를 -10 ℃로 냉각 후 소듐에톡사이드 101.2 g (20 wt% in ethanol)를 적가한다. 적가 후 상온에서 4시간 동안 교반하였다. 암모늄클로라이드 포화용액을 넣고 아세테이트산에틸 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 A-2>를 얻었다. (52.1 g, 51.6%)Add 70.0 g of <A-1>, 192.1 g of <A-2a>, and 616 mL of ethanol to the reactor and stir. After cooling the reaction temperature to -10 ℃, sodium ethoxide 101.2 g (20 wt% in ethanol) was added dropwise. After dropwise addition, the mixture was stirred at room temperature for 4 hours. After adding saturated ammonium chloride solution and adding ethyl acetate, the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate A-2>. (52.1 g, 51.6%)
합성예synthesis example 1-3 : 중간체 A-3의 합성 1-3: Synthesis of Intermediate A-3
<A-2> <A-3><A-2> <A-3>
반응기에 <중간체 A-2> 52.1 g, 에탄올 313 mL 투입 후 교반한다. 포타슘하이드록사이드 28 g으로 만든 수용액 540 mL를 반응기에 넣고 60 ℃로 승온 후 10시간 동안 환류교반하였다. 상온으로 냉각 후 반응액을 얼음물 2 L에 넣고 여과한 다음 물로 세척하였다. 여과액에 산성 상태(pH 4)가 될 때까지 2 노르말 염산을 적가한다. 생성된 고체를 여과하고 얼음물로 세척하여 <중간체 A-3>를 얻었다. (39.6 g, 84.8%)52.1 g of <Intermediate A-2> and 313 mL of ethanol were added to the reactor, followed by stirring. 540 mL of an aqueous solution made of 28 g of potassium hydroxide was put into a reactor, heated to 60 ° C, and stirred under reflux for 10 hours. After cooling to room temperature, the reaction solution was poured into 2 L of ice water, filtered, and then washed with water. 2 Normal hydrochloric acid is added dropwise to the filtrate until it becomes acidic (pH 4). The resulting solid was filtered and washed with ice water to obtain <Intermediate A-3>. (39.6 g, 84.8%)
합성예synthesis example 1-4 : 중간체 A-4의 합성 1-4: Synthesis of Intermediate A-4
<A-3> <A-4><A-3> <A-4>
반응기에 <중간체 A-3> 39.6 g, 포타슘하이드록사이드 17.4 g, 에틸렌글라이콜 131 mL을 넣고 반응 온도를 160 ℃로 승온 후 4시간 동안 교반하였다. 상온으로 냉각한 다음, 메틸렌클로라이드와 물을 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 A-4>를 얻었다. (21.4 g, 65.8%)39.6 g of <Intermediate A-3>, 17.4 g of potassium hydroxide, and 131 mL of ethylene glycol were added to the reactor, and the reaction temperature was raised to 160° C., followed by stirring for 4 hours. After cooling to room temperature, methylene chloride and water were added, and the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate A-4>. (21.4 g, 65.8%)
합성예synthesis example 1-5 : 중간체 A-5의 합성 1-5: Synthesis of Intermediate A-5
<A-4> <A-4a> <A-5><A-4> <A-4a> <A-5>
반응기에 <중간체 A-4> 24.0 g, <중간체 A-4a> 21.2 g, 비스(트리-터셔리-부틸포스핀)팔라듐(0) 1.1 g, 소듐 터셔리 부톡사이드 20.4 g, 톨루엔 240 mL을 투입 후, 16시간 동안 환류교반하였다. 상온으로 냉각한 다음, 아세테이트산에틸과 물을 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 A-5>를 얻었다. (24.0 g, 65.6%)24.0 g of <Intermediate A-4>, 21.2 g of <Intermediate A-4a>, 1.1 g of bis(tri-tert-butylphosphine)palladium(0), 20.4 g of sodium tertiary butoxide, and 240 mL of toluene were added to the reactor. After addition, the mixture was stirred under reflux for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate A-5>. (24.0 g, 65.6%)
합성예synthesis example 1-6 : 중간체 A-6의 합성 1-6: synthesis of intermediate A-6
<A-5> <A-5a> <A-6><A-5> <A-5a> <A-6>
반응기에 <중간체 A-5> 24.0 g, <중간체 A-5a> 19.6 g, 비스(트리-터셔리-부틸포스핀)팔라듐(0) 0.7 g, 소듐 터셔리 부톡사이드 13.4 g, 톨루엔 240 mL을 투입 후, 16시간 동안 환류교반하였다. 상온으로 냉각한 다음, 아세테이트산에틸과 물을 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 A-6>를 얻었다. (27.5 g, 66.9%)24.0 g of <Intermediate A-5>, 19.6 g of <Intermediate A-5a>, 0.7 g of bis(tri-tert-butylphosphine)palladium(0), 13.4 g of sodium tertiary butoxide, and 240 mL of toluene were added to the reactor. After addition, the mixture was stirred under reflux for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate A-6>. (27.5 g, 66.9%)
합성예synthesis example 1-7 : [ 1-7: [ 1]의1] 합성 synthesis
<A-6> [1]<A-6> [One]
반응기에 <중간체 A-6> 27.5 g와 터셔리 부틸벤젠 330 mL를 투입 후, -78 ℃에서 1.7 M 터셔리 부틸리튬 펜탄 용액 82 mL를 적가하였다. 60 ℃로 승온 후, 2시간 교반한다음, 60 ℃에서 질소를 불어 펜탄을 완전히 제거하였다. -78 ℃로 냉각 후, 보론 트리브로마이드 9 mL를 적가하였다. 상온으로 승온 후, 2시간 교반한 다음, 0 ℃로 냉각 후, N,N-디아이소프로필에틸아민 16 mL를 적가하였다. 120 ℃로 승온 후, 16시간 동안 교반하였다. 상온으로 냉각 후, 10% 소듐 아세테이트 수용액과 아세테이트산에틸을 투입한 다음, 유기층을 분리하고 감압농축하였다. 실리카겔크로마토그래피로 정제하여, 화합물 [1]을 얻었다. (2.1 g, 8%)After introducing 27.5 g of <Intermediate A-6> and 330 mL of tert-butylbenzene into the reactor, 82 mL of 1.7 M tert-butyllithium pentane solution was added dropwise at -78 °C. After raising the temperature to 60 ° C., stirring for 2 hours, pentane was completely removed by blowing nitrogen at 60 ° C. After cooling to -78 °C, 9 mL of boron tribromide was added dropwise. After raising the temperature to room temperature, stirring for 2 hours, and then cooling to 0° C., 16 mL of N,N-diisopropylethylamine was added dropwise. After raising the temperature to 120 °C, the mixture was stirred for 16 hours. After cooling to room temperature, a 10% sodium acetate aqueous solution and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. Purification was performed by silica gel chromatography to obtain compound [1]. (2.1 g, 8%)
MS (MALDI-TOF) : m/z 562.26 [M+]MS (MALDI-TOF): m/z 562.26 [M + ]
합성예synthesis example 2 : [ 2 : [ 14]의14] 합성 synthesis
합성예synthesis example 2-1 : 중간체 B-1의 합성 2-1: Synthesis of Intermediate B-1
<A-5> <A-4> <B-1><A-5> <A-4> <B-1>
반응기에 <중간체 A-5> 23.0 g, <중간체 A-4> 13.3 g, 비스(트리-터셔리-부틸포스핀)팔라듐(0) 0.68 g, 소듐 터셔리 부톡사이드 12.84 g, 톨루엔 230 mL을 투입 후, 16시간 동안 환류교반하였다. 상온으로 냉각한 다음, 아세테이트산에틸과 물을 투입 후, 유기층을 분리하였다. 실리카겔크로마토그래피로 정제하여, <중간체 B-1>를 얻었다. (21.0 g, 61.9%)23.0 g of <Intermediate A-5>, 13.3 g of <Intermediate A-4>, 0.68 g of bis(tri-tert-butylphosphine)palladium(0), 12.84 g of sodium tertiary butoxide, and 230 mL of toluene were added to the reactor. After addition, the mixture was stirred under reflux for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. It was purified by silica gel chromatography to obtain <Intermediate B-1>. (21.0 g, 61.9%)
합성예synthesis example 2-2 : [ 2-2: [ 14]의14] 합성 synthesis
<B-1> [14]<B-1> [14]
반응기에 <중간체 B-1> 21.0 g와 터셔리 부틸벤젠 252 mL를 투입 후, -78 ℃에서 1.7 M 터셔리 부틸리튬 펜탄 용액 73 mL를 적가하였다. 60 ℃로 승온 후, 2시간 교반한다음, 60 ℃에서 질소를 불어 펜탄을 완전히 제거하였다. -78 ℃로 냉각 후, 보론 트리브로마이드 8 mL를 적가하였다. 상온으로 승온 후, 2시간 교반한 다음, 0 ℃로 냉각 후, N,N-디아이소프로필에틸아민 14 mL를 적가하였다. 120 ℃로 승온 후, 16시간 동안 교반하였다. 상온으로 냉각 후, 10% 소듐 아세테이트 수용액과 아세테이트산에틸을 투입한 다음, 유기층을 분리하고 감압농축하였다. 실리카겔크로마토그래피로 정제하여, [14]를 얻었다. (1.65g, 8.3%)After putting 21.0 g of <Intermediate B-1> and 252 mL of tert-butylbenzene into the reactor, 73 mL of 1.7 M tertiary butyllithium pentane solution was added dropwise at -78 °C. After raising the temperature to 60 ° C., stirring for 2 hours, pentane was completely removed by blowing nitrogen at 60 ° C. After cooling to -78 °C, 8 mL of boron tribromide was added dropwise. After the temperature was raised to room temperature, the mixture was stirred for 2 hours, cooled to 0° C., and 14 mL of N,N-diisopropylethylamine was added dropwise. After raising the temperature to 120 °C, the mixture was stirred for 16 hours. After cooling to room temperature, a 10% sodium acetate aqueous solution and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. Purification by silica gel chromatography gave [14]. (1.65g, 8.3%)
MS (MALDI-TOF) : m/z 480.09 [M+]MS (MALDI-TOF): m/z 480.09 [M + ]
합성예synthesis example 1 내지 4 : 유기발광소자의 제조 1 to 4: Manufacture of organic light emitting device
ITO 글래스의 발광 면적이 2 mm ⅹ 2 mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1 ⅹ 10-7 torr가 되도록 한 후 상기 ITO 위에 DNTPD (700 Å), [화학식 H] (250 Å) 순으로 성막하였다. 발광층은 하기에 기재된 호스트 [BH1]과 본 발명의 화합물 (3 wt%)을 혼합하여 성막 (250 Å)한 다음, 이후에 전자수송층으로 [화학식 E-1]과 [화학식 E-2]을 1:1의 비로 300 Å, 전자주입층으로 [화학식 E-1]을 5 Å, Al (1000 Å)의순서로 성막하여 유기발광 소자를 제조하였다. 상기 유기발광소자의 발광특성은 0.4 mA에서 측정하였다.The ITO glass was patterned so that the light emitting area had a size of 2 mm x 2 mm, and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 ⅹ 10 −7 torr, and then a film of DNTPD (700 Å) and [Formula H] (250 Å) was formed on the ITO in this order. The light emitting layer is formed by mixing the host [BH1] described below and the compound (3 wt%) of the present invention to form a film (250 Å), and then [Formula E-1] and [Formula E-2] are formed as 1 An organic light emitting device was manufactured by forming a film of 300 Å at a ratio of: 1, [Formula E-1] as an electron injection layer in the order of 5 Å, and Al (1000 Å). The emission characteristics of the organic light emitting device were measured at 0.4 mA.
[DNTPD] [화학식 H][DNTPD] [Formula H]
[화학식 E-1] [화학식 E-2] [BH1][Formula E-1] [Formula E-2] [BH1]
비교예comparative example 1 내지 2 1 to 2
상기 실시예에서 사용된 본 발명에 따른 도판트 화합물 대신 하기 [BD-1] 및 [BD-2]를 사용한 것 이외에는 동일하게 유기발광소자를 제작하였으며, 상기 유기발광소자의 발광특성은 0.4 mA에서 측정하였다. 상기 [BD-1] 및 [BD-2]의 구조는 다음과 같다.An organic light emitting device was manufactured in the same manner except for using the following [BD-1] and [BD-2] instead of the dopant compound according to the present invention used in the above example, and the light emitting characteristic of the organic light emitting device was 0.4 mA measured. The structures of [BD-1] and [BD-2] are as follows.
[BD-1] [BD-2][BD-1] [BD-2]
(mA/cm2)current density
(mA/cm 2 )
(V)Voltage
(V)
(EQE, %)efficiency
(EQE, %)
상기 [표 1]에서 보는 바와 같이, 본 발명에 따른 화합물을 소자 내 발광층 도판트 화합물로 채용한 유기발광소자는 종래 유기발광소자에 널리 사용된 도판트 화합물을 채용한 소자 (비교예 1 내지 2) 대비 향상된 저전압 구동 특성과 우수한 외부양자효율을 가져서 고효율의 유기발광소자를 구현할 수 있다.As shown in [Table 1], the organic light emitting device employing the compound according to the present invention as a dopant compound for the light emitting layer in the device is a device employing a dopant compound widely used in conventional organic light emitting devices (Comparative Examples 1 to 2). ), a high-efficiency organic light-emitting device can be realized by having improved low-voltage driving characteristics and excellent external quantum efficiency compared to the present invention.
Claims (10)
[화학식 A] [화학식 B]
상기 [화학식 A] 또는 [화학식 B]에서,
Y는 B, P=O, P=S 또는 Al이고,
X1 내지 X3는 각각 독립적으로 NR7, O, S, CR8R9 또는 SiR10R11이며,
Q1 및 Q2는 각각 독립적으로 치환 또는 비치환된 탄소수 5 내지 50의 방향족 탄화수소 고리, 치환 또는 비치환된 탄소수 2 내지 50의 방향족 헤테로고리, 치환 또는 비치환된 탄소수 3 내지 30의 지방족 고리 및 치환 또는 비치환된 탄소수 3 내지 30의 지방족 방향족 혼합 고리 중 선택되는 어느 하나이며,
상기 R1 내지 R11은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택되는 어느 하나이며,
상기 R1 및 R2는 인접한 치환기와 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있고,
상기 R7 내지 R11은 Q1 또는 Q2와 연결되어 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있으며,
상기 R3와 R4 및 R5와 R6는 각각 서로 연결되어 치환 또는 비치환된 지환족 또는 방향족의 단일환 또는 다환의 고리를 추가 형성할 수 있다.A polycyclic compound represented by the following [Formula A] or [Formula B]:
[Formula A] [Formula B]
In [Formula A] or [Formula B],
Y is B, P = O, P = S or Al,
X 1 to X 3 are each independently NR 7 , O, S, CR 8 R 9 or SiR 10 R 11 ;
Q 1 and Q 2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and Any one selected from substituted or unsubstituted aliphatic aromatic mixed rings having 3 to 30 carbon atoms,
R 1 to R 11 are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted carbon atom. Cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted Any one selected from an unsubstituted silyl group, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group,
The R 1 and R 2 may be linked to adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The R 7 to R 11 may be connected to Q 1 or Q 2 to further form an alicyclic or aromatic monocyclic or polycyclic ring,
The R 3 and R 4 and R 5 and R 6 may be connected to each other to further form a substituted or unsubstituted alicyclic or aromatic monocyclic or polycyclic ring.
상기 [화학식 A]는 하기 [화학식 A-1]으로 표시되는 다환 고리 화합물:
[화학식 A-1]
상기 [화학식 A-1]에서,
R은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택되는 어느 하나이며,
X1, X3, Q1, Q2 및 R1의 정의는 상기 [화학식 A]에서 정의한 바와 동일하다.According to claim 1,
[Formula A] is a polycyclic compound represented by the following [Formula A-1]:
[Formula A-1]
In the above [Formula A-1],
R are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Any one selected from an aliphatic aromatic mixed ring group having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group,
Definitions of X 1 , X 3 , Q 1 , Q 2 and R 1 are the same as defined in [Formula A].
상기 [화학식 B]는 하기 [화학식 B-1] 또는 [화학식 B-2]로 표시되는 다환 고리 화합물:
[화학식 B-1] [화학식 B-2]
상기 [화학식 B-1] 및 [화학식 B-2]에서,
R은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 6 내지 50 아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 탄소수 3 내지 20의 지방족 방향족 혼합 고리기, 니트로기, 시아노기 및 할로겐기 중에서 선택되는 어느 하나이며,
X1 및 X2, R1 내지 R4 및 Q2의 정의는 상기 [화학식 B]에서 정의한 바와 동일하다.According to claim 1,
[Formula B] is a polycyclic compound represented by the following [Formula B-1] or [Formula B-2]:
[Formula B-1] [Formula B-2]
In [Formula B-1] and [Formula B-2],
R are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted Heterocycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Any one selected from an aliphatic aromatic mixed ring group having 3 to 20 carbon atoms, a nitro group, a cyano group, and a halogen group,
The definitions of X 1 and X 2 , R 1 to R 4 and Q 2 are the same as defined in [Formula B] above.
상기 Y는 B이고, 상기 R1 및 R2는 각각 치환 또는 비치환된 탄소수 6 내지 30의 아릴기인 것을 특징으로 하는 다환 고리 화합물.According to claim 1,
Wherein Y is B, wherein R 1 and R 2 are each a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
상기 [화학식 A] 또는 [화학식 B]로 표시되는 화합물은 하기 [1] 내지 [48] 중에서 선택되는 어느 하나의 다환고리 화합물:
The compound represented by [Formula A] or [Formula B] is any one polycyclic compound selected from the following [1] to [48]:
상기 유기층이 제1항에 따른 [화학식 1]로 표시되는 다환 고리 화합물을 1 종 이상 포함하는 유기발광소자.A first electrode, a second electrode opposite the first electrode, and an organic layer interposed between the first electrode and the second electrode,
An organic light emitting device in which the organic layer includes at least one polycyclic compound represented by [Chemical Formula 1] according to claim 1.
상기 유기층은 전자주입층, 전자수송층, 정공주입층, 정공수송층, 전자저지층, 정공저지층 및 발광층 중 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 1]로 표시되는 다환 고리 화합물을 포함하는 것을 특징으로 하는 유기발광소자.According to claim 6,
The organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
An organic light emitting device characterized in that at least one layer among the layers includes a polycyclic ring compound represented by the above [Chemical Formula 1].
상기 발광층은 호스트와 도판트로 이루어지고, 상기 [화학식 1]로 표시되는 다환 고리 화합물이 발광층 내 도판트인 것을 특징으로 하는 유기발광소자.According to claim 7,
The light emitting layer is composed of a host and a dopant, and the organic light emitting device, characterized in that the polycyclic compound represented by the [Chemical Formula 1] is a dopant in the light emitting layer.
상기 각각의 층중에서 선택된 하나 이상의 층은 증착공정 또는 용액공정에 의해 형성되는 것을 특징으로 하는 유기발광소자.According to claim 7,
At least one layer selected from the respective layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process.
상기 유기발광소자는 평판 디스플레이 장치; 플렉시블 디스플레이 장치; 단색 또는 백색의 평판 조명용 장치; 및 단색 또는 백색의 플렉시블 조명용 장치; 차량용 디스플레이 장치; 및 가상 또는 증강 현실용 디스플레이 장치;에서 선택되는 어느 하나의 장치에 사용되는 것을 특징으로 하는 유기발광소자.According to claim 6,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; and monochromatic or white flexible lighting devices; vehicle display devices; And a display device for virtual or augmented reality; organic light emitting device characterized in that used in any one device selected from.
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