KR20150058084A - Novel electroluminescent compound and organic electroluminescent device comprising same - Google Patents
Novel electroluminescent compound and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- KR20150058084A KR20150058084A KR1020140162365A KR20140162365A KR20150058084A KR 20150058084 A KR20150058084 A KR 20150058084A KR 1020140162365 A KR1020140162365 A KR 1020140162365A KR 20140162365 A KR20140162365 A KR 20140162365A KR 20150058084 A KR20150058084 A KR 20150058084A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- halogen
- unsubstituted
- nitrile
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 84
- 125000003277 amino group Chemical group 0.000 claims description 71
- 125000002560 nitrile group Chemical group 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 19
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052714 tellurium Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000012546 transfer Methods 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 74
- 239000000543 intermediate Substances 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 39
- 239000000463 material Substances 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 22
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001771 vacuum deposition Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000000151 deposition Methods 0.000 description 7
- 230000008021 deposition Effects 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- -1 phthalocyanine compound Chemical class 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- 0 CCCC[C@]1C(N=CC(C)=CCC)=C(C)CCC1*C Chemical compound CCCC[C@]1C(N=CC(C)=CCC)=C(C)CCC1*C 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- PKRRNTJIHGOMRC-UHFFFAOYSA-N 1-benzofuran-2-ylboronic acid Chemical compound C1=CC=C2OC(B(O)O)=CC2=C1 PKRRNTJIHGOMRC-UHFFFAOYSA-N 0.000 description 1
- DFUGYZQSDFQVPU-UHFFFAOYSA-N 1-benzofuran-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=COC2=C1 DFUGYZQSDFQVPU-UHFFFAOYSA-N 0.000 description 1
- QVANIYYVZZLQJP-UHFFFAOYSA-N 1-benzothiophen-3-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CSC2=C1 QVANIYYVZZLQJP-UHFFFAOYSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- AOUGDAYMVXBDDZ-UHFFFAOYSA-N CCC1=CCC(C)=C1 Chemical compound CCC1=CCC(C)=C1 AOUGDAYMVXBDDZ-UHFFFAOYSA-N 0.000 description 1
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- HHJFMHZFDXRKPM-UHFFFAOYSA-N OB(O)C1=CC2=CC=CC=C2N1C1=CC=CC=C1 Chemical compound OB(O)C1=CC2=CC=CC=C2N1C1=CC=CC=C1 HHJFMHZFDXRKPM-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- YNCYPMUJDDXIRH-UHFFFAOYSA-N benzo[b]thiophene-2-boronic acid Chemical compound C1=CC=C2SC(B(O)O)=CC2=C1 YNCYPMUJDDXIRH-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical class C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
- 150000003852 triazoles Chemical class 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
Images
Classifications
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 신규한 발광 화합물 및 이를 포함하는 유기발광소자에 관한 것이다.
The present invention relates to a novel light emitting compound and an organic light emitting device including the same.
최근, 자체 발광형으로 저전압 구동이 가능한 유기발광소자는, 평판 표시소자의 주류인 액정디스플레이(LCD, liquid crystal display)에 비해, 시야각, 대조비 등이 우수하고 백라이트가 불필요하여 경량 및 박형이 가능하며 소비전력 측면에서도 유리하고 색 재현 범위가 넓어, 차세대 표시소자로서 주목을 받고 있다.In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.
유기발광소자에서 유기물 층으로 사용되는 재료는 크게 기능에 따라, 발광 재료, 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자과 저분자로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있으며, 발광 재료는 발광 색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트와 호스트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excitation state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism, Can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on the emission color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.
현재까지 이러한 유기발광소자에 사용되는 물질로서 다양한 화합물들이 알려져 있으나, 이제까지 알려진 물질을 이용한 유기발광소자의 경우 높은 구동전압, 낮은 효율 및 짧은 수명으로 인해 실용화하는 데에 많은 어려움이 있었다. 따라서, 우수한 특성을 갖는 물질을 이용하여 저전압 구동, 고휘도 및 장수명을 갖는 유기발광소자를 개발하려는 노력이 지속되어 왔다.
Various compounds have been known as materials used in such organic light emitting devices. However, organic light emitting devices using known materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.
상기와 같은 문제점을 해결하기 위해, 본 발명은 전하전달 특성이 우수하고, 동시에 높은 삼중항 에너지 및 높은 Tg를 가져, 유기발광소자에 적용시 낮은 구동전압, 고효율, 저소비전력, 장수명을 가지게 할 수 있는 신규한 발광 화합물을 제공하는 것을 목적으로 한다.
In order to solve the above-mentioned problems, the present invention has an excellent charge-transporting property, a high triplet energy and a high Tg, and can provide low driving voltage, high efficiency, low power consumption and long life And to provide a novel luminescent compound having such a structure.
본 발명은 또한 상기 화합물을 포함하여 낮은 구동전압, 고효율, 저소비전력, 장수명 구현이 가능한 유기발광소자를 제공하는 것을 목적으로 한다.
It is another object of the present invention to provide an organic light emitting device including the above compound capable of realizing low driving voltage, high efficiency, low power consumption, and long life.
상기 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 발광 화합물을 제공한다:In order to accomplish the above object, the present invention provides a luminescent compound represented by the following Formula 1:
[화학식 1][Chemical Formula 1]
A-L-BA-L-B
상기 식에서,In this formula,
A는 하기 A1 내지 A30으로 표시되는 구조 중 하나이며, 여기서 A에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있으며,A is one of the structures represented by the following formulas A1 to A30, wherein each of the hydrogen atoms contained in A may independently be substituted or unsubstituted with a deuterium, a halogen, an amino group, a nitrile group, a nitro group,
L은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,L is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, C 1-30, C 6-30 An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group unsubstituted or substituted with a C 2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1-30 alkyl group, a C 2-30 alkenyl group, an alkoxy group an alkynyl group, a C 1-30 of C 2-30, aryl of C 6-30 An aryl group of C 6-30 , or a C 2-50 heteroaryl group which is unsubstituted or substituted with a C 2-30 heteroaryl group,
B는 하기 B1 내지 B10으로 표시되는 구조 중 하나이며, 여기서 B에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있다.B is one of the structures represented by the following formulas B1 to B10, wherein each of the hydrogen atoms contained in B may independently be substituted or unsubstituted with deuterium, halogen, amino, nitrile or nitro.
상기 구조들에서, -*는 결합부위이고, Ar1 및 Ar2는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이다.
In the above structures, - is a bonding site, Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile or nitro.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 발광물질로서 유기물층에 포함하는 유기발광소자를 제공한다.
Also, the present invention provides an organic light emitting device including the compound represented by Formula 1 as an organic material layer as a light emitting material.
본 발명의 발광 화합물은 전하전달 특성이 우수하고, 동시에 높은 삼중항 에너지 및 높은 Tg를 가져, 유기발광소자에 적용시 낮은 구동전압, 고효율, 저소비전력, 장수명을 가지게 할 수 있다.
The luminescent compound of the present invention is excellent in charge transfer characteristics, has high triplet energy and high Tg, and can have low driving voltage, high efficiency, low power consumption, and long life when applied to an organic light emitting device.
도 1은 본 발명의 일 실시예에 따른 OLED의 단면을 개략적으로 도시한 것이다.
도면의 부호
10 : 기판
11 : 양극
12 : 정공주입층
13 : 정공전달층
14 : 발광층
15 : 전자전달층
16: 음극1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
The sign
10: substrate
11: anode
12: Hole injection layer
13: hole transport layer
14:
15: electron transport layer
16: cathode
본 발명의 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.The compound of the present invention is characterized by being represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
A-L-BA-L-B
상기 식에서,In this formula,
A는 하기 A1 내지 A30으로 표시되는 구조 중 하나이며, 여기서 A에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있으며,A is one of the structures represented by the following formulas A1 to A30, wherein each of the hydrogen atoms contained in A may independently be substituted or unsubstituted with a deuterium, a halogen, an amino group, a nitrile group, a nitro group,
L은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고, 바람직하기로 L은 하기 구조들 중 하나이며,L is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, C 1-30, C 6-30 An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group unsubstituted or substituted with a C 2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1-30 alkyl group, a C 2-30 alkenyl group, an alkoxy group an alkynyl group, a C 1-30 of C 2-30, aryl of C 6-30 An aryl group of C 6-30 , or a C 2-50 heteroaryl group optionally substituted by a C 2-30 heteroaryl group, preferably L is one of the following structures,
B는 하기 B1 내지 B10으로 표시되는 구조 중 하나이며, 여기서 B에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있다.B is one of the structures represented by the following formulas B1 to B10, wherein each of the hydrogen atoms contained in B may independently be substituted or unsubstituted with deuterium, halogen, amino, nitrile or nitro.
상기 구조들에서, -*는 결합부위이고, In the above structures, - is a binding site,
Ar1 및 Ar2는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이다. 바람직하기로 상기 Ar1 및 Ar2는 각각 독립적으로 하기 구조들 중 하나이다.Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile or nitro. Preferably, Ar 1 and Ar 2 are each independently one of the following structures.
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물은 바람직하기로 하기 표시되는 구조들 중 하나인 것이 좋다. In the present invention, the compound represented by Formula 1 is preferably one of the structures shown below.
상기에서 X1 및 X2는 각각 독립적으로 S, O, Se, Te 또는 N-Ar3이며, 여기서 Ar3은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이며,Wherein X 1 and X 2 are each independently S, O, Se, Te or N-Ar 3 wherein Ar 3 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 헤테로아릴기이다.
Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, C 1-30, C 6-30 of An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group unsubstituted or substituted with a C 2-30 heteroaryl group ; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1-30 alkyl group, a C 2-30 alkenyl group, an alkoxy group an alkynyl group, a C 1-30 of C 2-30, aryl of C 6-30 An aryl group of C 6-30 , or a C 6-50 heteroaryl group which is unsubstituted or substituted with a C 2-30 heteroaryl group.
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물은 더욱 바람직하기로 하기 표시되는 구조들 중 하나인 것이 좋다. In the present invention, the compound represented by Formula 1 is more preferably one of the structures shown below.
상기에서 X1 및 X2는 각각 독립적으로 S, O, Se, Te 또는 N-Ar4이며, 여기서 Ar4는 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이며,Wherein X 1 and X 2 are each independently S, O, Se, Te or N-Ar 4 , wherein Ar 4 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group,
Y는 CR1 또는 N이며 여기서 R1은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이다.
Y is CR 1 or N, where R 1 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile or nitro.
본 발명에 있어서, 상기 화학식 1로 표시되는 화합물의 바람직한 예는 다음과 같다.In the present invention, preferred examples of the compound represented by the formula (1) are as follows.
본 발명에 따른 화학식 1의 화합물은 전하전달 특성이 우수하고, 동시에 높은 삼중항 에너지 및 높은 Tg를 가져, 유기발광소자에 적용시 낮은 구동전압, 고효율, 저소비전력, 장수명을 가지게 할 수 있다.
The compound of formula (I) according to the present invention has excellent charge transfer characteristics, and has high triplet energy and high Tg. Thus, when applied to an organic light emitting device, it can have low driving voltage, high efficiency, low power consumption and long life.
또한 본 발명의 화합물은 하기 반응식 1과 같은 과정을 제조될 수 있다. The compounds of the present invention can also be prepared according to the following reaction scheme (1).
[반응식 1][Reaction Scheme 1]
구체적인 예로 반응식 1-1이 적용될 수 있다.Reaction Scheme 1-1 may be applied as a specific example.
[반응식 1-1][Reaction Scheme 1-1]
상기 반응식 1 및 반응식 1-1에서 A, L, B, X1, X2는 상기 화학식 1에서 정의한 바와 같다.
Wherein A, L, B, X 1 and X 2 are as defined in the above formula (1).
또한, 본 발명은 발광물질로서 상기 화학식 1로 표시되는 화합물을 유기물층에 포함하는 유기발광소자를 제공한다. 이때, 본 발명의 화합물은 단독으로 사용되거나 공지의 유기발광 화합물과 함께 사용될 수 있다.In addition, the present invention provides an organic light emitting device including a compound represented by Formula 1 as a light emitting material in an organic material layer. At this time, the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
또한 본 발명의 유기발광소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층을 포함하는 바, 상기 유기발광소자의 제조방법을 설명하면 다음과 같다.In addition, the organic light emitting device of the present invention includes one or more organic layers including the compound represented by Formula 1, and the method of manufacturing the organic light emitting device will now be described.
상기 유기발광소자는 애노드(anode)와 캐소드(cathod) 사이에 정공주입층(HIL), 정공수송층(HTL), 발광층(EML), 전자수송층(ETL), 전자주입층(EIL) 등의 유기물층을 1 개 이상 포함할 수 있다.The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more can be included.
먼저, 기판 상부에 높은 일함수를 갖는 애노드 전극용 물질을 증착시켜 애노드를 형성한다. 이때, 상기 기판은 통상의 유기발광소자에서 사용되는 기판을 사용할 수 있으며, 특히 기계적 강도, 열적 안정성, 투명성, 표면평활성, 취급용이성, 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판을 사용하는 것이 좋다. 또한, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용할 수 있다. 상기 애노드 전극용 물질은 통상의 애노드 형성방법에 의해 증착할 수 있으며, 구체적으로 증착법 또는 스퍼터링법에 의해 증착할 수 있다.First, an anode electrode material having a high work function is deposited on the substrate to form an anode. At this time, the substrate can be a substrate used in conventional organic light emitting devices, and it is particularly preferable to use a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.
그 다음, 상기 애노드 전극 상부에 정공주입층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB(Langmuir-Blodgett)법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 또한 핀정공이 발생하기 어렵다는 등의 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공주입층을 형성하는 경우 그 증착조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 정공주입층의 구조 및 열적특성 등에 따라 다르지만, 일반적으로 50-500 ℃의 증착온도, 10-8 내지 10-3 torr의 진공도, 0.01 내지 100 Å/sec의 증착속도, 10 Å 내지 5 ㎛의 층 두께 범위에서 적절히 선택하는 것이 바람직하다.Next, a hole injection layer material may be formed on the anode electrode by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB (Langmuir-Blodgett) method, but it is easy to obtain a uniform film quality, It is preferable to form it by a vacuum evaporation method. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. In general, the deposition temperature is 50-500 [ A vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 탆.
상기 정공주입층 물질은 특별히 제한되지 않으며, 미국특허 제4,356,429호에 개시된 구리 프탈로시아닌 등의 프탈로시아닌 화합물 또는 스타버스트형 아민 유도체류인 TCTA(4,4',4"-트리(N-카바졸릴)트리페닐아민), m-MTDATA(4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민), m-MTDAPB(4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠), HI-406(N1,N1'-(비페닐-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민) 등을 정공주입층 물질로 사용할 수 있다.The hole injection layer material is not particularly limited and may be a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl) tri (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB ), HI-406 (N 1 , N 1 '- ( biphenyl-4,4'-diyl) bis (N 1 - (naphthalen-1-yl) -N 4, N 4 - benzene-1,4-diphenyl -Diamine) can be used as a hole injection layer material.
다음으로 상기 정공주입층 상부에 정공수송층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 정공수송층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.Next, a hole transporting layer material may be formed on the hole injecting layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, since a uniform film quality can be easily obtained, It is preferably formed by a vapor deposition method. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer.
또한, 상기 정공수송층 물질은 특별히 제한되지는 않으며, 정공수송층에 사용되고 있는 통상의 공지 물질 중에서 임의로 선택하여 사용할 수 있다. 구체적으로, 상기 정공수송층 물질은 N-페닐카바졸, 폴리비닐카바졸 등의 카바졸 유도체, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD), N.N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등의 방향족 축합환을 가지는 통상의 아민 유도체 등이 사용될 수 있다.In addition, the hole transport layer material is not particularly limited, and may be selected from any conventionally known materials used in the hole transport layer. Specifically, the hole transport layer material may be a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a carbazole derivative such as N, N'-bis (3-methylphenyl) -N, N'- Phenyl) -4,4'-diamine (TPD), and N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine Derivatives and the like can be used.
그 후, 상기 정공수송층 상부에 발광층 물질을 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법에 의해 형성할 수 있지만, 균일한 막질을 얻기 쉽고, 핀정공이 발생하기 어렵다는 점에서 진공증착법에 의해 형성하는 것이 바람직하다. 상기 진공증착법에 의해 발광층을 형성하는 경우 그 증착조건은 사용하는 화합물에 따라 다르지만 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다. 또한, 상기 발광층 재료는 본 발명의 화학식 1로 표시되는 화합물을 호스트 또는 도펀트로 사용할 수 있다.Then, the light emitting layer material may be formed on the hole transporting layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, from the viewpoint of obtaining a uniform film quality and difficulty in producing pin holes, As shown in Fig. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may use the compound represented by the formula (1) of the present invention as a host or a dopant.
상기 화학식 1로 표시되는 화합물을 발광 호스트로 사용하는 경우, 인광 또는 형광 도펀트를 함께 사용하여 발광층을 형성할 수 있다. 이때, 형광 도펀트로는 이데미츠사(Idemitsu사)에서 구입 가능한 IDE102 또는 IDE105, 또는 BD142(N6,N12-비스(3,4-디메틸페닐)-N6,N12-디메시틸크리센-6,12-디아민)를 사용할 수 있으며, 인광 도펀트로는 녹색 인광 도펀트 Ir(ppy)3(트리스(2-페닐피리딘) 이리듐), 청색 인광 도펀트인 F2Irpic(이리듐(Ⅲ) 비스[4,6-다이플루오로페닐)-피리디나토-N,C2'] 피콜린산염), UDC사의 적색 인광 도펀트 RD61 등이 공동 진공증착(도핑)될 수 있다. 도펀트의 도핑농도는 특별히 제한되지 않으나, 호스트 100 중량부 대비 도펀트가 0.01 내지 15 중량부로 도핑되는 것이 바람직하다. 만약 도펀트의 함량이 0.01 중량부 미만일 경우에는 도펀트량이 충분치 못하여 발색이 제대로 이루어지지 않는다는 문제점이 있으며, 15 중량부를 초과할 경우에는 농도 소광 현상으로 인해 효율이 급격히 감소된다는 문제점이 있다.When the compound represented by Formula 1 is used as a light emitting host, a phosphorescent or fluorescent dopant may be used together to form a light emitting layer. At this time, the fluorescent dopant to the possible purchase from Idemitsu Co. (Idemitsu Corporation) IDE102 or IDE105, or BD142 (N 6, N 12-bis (3,4-dimethylphenyl) -N 6, N 12 - D-mesityl chrysene - as may be used to 6,12- diamine), the phosphorescent dopant is a green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), a blue phosphorescent dopant F2Irpic (iridium (ⅲ) bis [4,6- Pyridino-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61, and the like can be vacuum vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but is preferably doped with 0.01 to 15 parts by weight of the dopant relative to 100 parts by weight of the host. If the content of the dopant is less than 0.01 part by weight, the amount of the dopant is not sufficient and color development is not properly performed. If the amount is more than 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.
또한, 발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여 정공억제재료(HBL)를 추가로 진공증착법 또는 스핀코팅법에 의해 적층시키는 것이 바람직하다. 이때 사용할 수 있는 정공억제물질은 특별히 제한되지는 않으나, 정공억제재료로 사용되고 있는 공지의 것에서 임의의 것을 선택해서 이용할 수 있다. 예를 들면, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 또는 일본특개평 11-329734(A1)에 기재되어 있는 정공억제재료 등을 들 수 있으며, 대표적으로 Balq(비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄 비페녹사이드), 페난트롤린(phenanthrolines)계 화합물(예: UDC사 BCP(바쏘쿠프로인)) 등을 사용할 수 있다.When the phosphorescent dopant is used together with the phosphorescent dopant, it is preferable to further laminate the hole blocking material (HBL) by a vacuum evaporation method or a spin coating method in order to prevent the triplet exciton or hole from diffusing into the electron transporting layer. The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.
상기와 같이 형성된 발광층 상부에는 전자수송층이 형성되는데, 이때 상기 전자수송층은 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.An electron transport layer is formed on the light emitting layer formed as described above. The electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
상기 전자수송층 재료는 전자주입전극으로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 그 종류가 특별히 제한되지는 않으며, 예를 들어 퀴놀린 유도체, 특히 트리스(8-퀴놀리놀라토)알루미늄(Alq3), 또는 ET4(6,6'-(3,4-디메시틸-1,1-디메틸-1H-실올-2,5-디일)디-2,2'-비피리딘)을 사용할 수 있다. 또한, 전자수송층 상부에 캐소드로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며, 전자주입층 물질로는 LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.The electron transport layer material serves to stably transport electrons injected from the electron injection electrode. The material is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), Or ET4 (6,6 '- (3,4-dimemethyl-1,1-dimethyl-1H-silanol-2,5-diyl) di-2,2'-bipyridine). In addition, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transport layer. Examples of the electron injection layer material include LiF, NaCl, CsF, Li 2 O, BaO Can be used.
또한, 상기 전자수송층의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건 범위에서 선택하는 것이 좋다.The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.
그 뒤, 상기 전자수송층 상부에 전자주입층 물질을 형성할 수 있으며, 이때 상기 전자수송층은 통상의 전자주입층 물질을 진공증착법, 스핀코팅법, 캐스트법 등의 방법으로 형성되며, 특히 진공증착법에 의해 형성하는 것이 바람직하다.Thereafter, an electron injection layer material may be formed on the electron transport layer, and the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like, .
마지막으로 전자주입층 상부에 캐소드 형성용 금속을 진공증착법이나 스퍼터링법 등의 방법에 의해 형성하고 캐소드로 사용한다. 여기서 캐소드 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물, 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 있다. 또한, 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Finally, a metal for forming a cathode is formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.
본 발명의 유기발광소자는 애노드, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 캐소드 구조의 유기발광소자 뿐만 아니라, 다양한 구조의 유기발광소자의 구조가 가능하며, 필요에 따라 1층 또는 2층의 중간층을 더 형성하는 것도 가능하다.The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.
상기와 같이 본 발명에 따라 형성되는 각 유기물층의 두께는 요구되는 정도에 따라 조절할 수 있으며, 바람직하게는 10 내지 1,000 ㎚이며, 더욱 바람직하게는 20 내지 150 ㎚인 것이 좋다.As described above, the thickness of each organic material layer formed according to the present invention can be controlled according to the required degree, preferably 10 to 1,000 nm, and more preferably 20 to 150 nm.
또한 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 유기물층의 두께를 분자 단위로 조절할 수 있기 때문에 표면이 균일하며, 형태안정성이 뛰어난 장점이 있다.
In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.
본 발명의 유기발광소자는 전하전달 특성이 우수하고, 동시에 높은 삼중항 에너지 및 높은 Tg를 가지는 화학식 1로 표시되는 화합물을 포함하여 낮은 구동전압, 고효율, 저소비전력, 장수명을 구현할 수 있다.
The organic light emitting device of the present invention can realize a low driving voltage, high efficiency, low power consumption and long life by including a compound represented by Chemical Formula 1 having excellent charge transfer characteristics and high triplet energy and high Tg.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
[중간체 A1의 합성][Synthesis of intermediate A1]
[A1-1의 합성] [Synthesis of A1-1]
둥근바닥플라스크에 dibenzo[b,d]furan-4-ylboronic acid 102.2 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1500 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 A1-1 98.7 g (수율 85%)를 얻었다.To a round bottom flask dibenzo [b, d] furan- 4-ylboronic acid 102.2 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, 1500 ml K 2 CO 3 (2M ) 600 ml , and Pd (PPh 3) 4 13.9 g, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 98.7 g (yield: 85%) of Intermediate A1-1.
[A1의 합성] [Synthesis of A1]
상기 A1-1 98 g을 1,2-dichlorobenzene 500 ml에 녹인 후 P(OEt)3 330 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 A1 52.3 g (수율 60%)를 얻었다.98 g of the above A1-1 was dissolved in 500 ml of 1,2-dichlorobenzene, 330 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 52.3 g (yield: 60%) of Intermediate A1.
[중간체 A2의 합성][Synthesis of intermediate A2]
[A2-1의 합성] [Synthesis of A2-1]
둥근바닥플라스크에 dibenzo[b,d]thiophen-4-ylboronic acid 109.9 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1500 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 A2-1 99.3 g (수율 81%)를 얻었다.To a round bottom flask dibenzo [b, d] thiophen- 4-ylboronic acid 109.9 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, 1500 ml K 2 CO 3 (2M ) 600 ml , and Pd (PPh 3) 4 13.9 g, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 99.3 g (81% yield) of intermediate A2-1.
[A2의 합성] [Synthesis of A2]
상기 A2-1 99 g을 1,2-dichlorobenzene 490 ml에 녹인 후 P(OEt)3 320 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 A2 54.0 g (수율 61%)를 얻었다.99 g of the above A2-1 was dissolved in 490 ml of 1,2-dichlorobenzene, 320 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 54.0 g (yield: 61%) of intermediate A2.
[중간체 A3의 합성][Synthesis of intermediate A3]
[A3-1의 합성] [Synthesis of A3-1]
둥근바닥플라스크에 (9-phenyl-9H-carbazol-1-yl)boronic acid 124.53 g, 1-iodo-2-nitrobenzene 90 g을 톨루엔 1500 ml에 녹이고 K2CO3(2M) 540 ml와 Pd(PPh3)4 12.5 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 A3-1 105.4 g (수율 80%)를 얻었다.124.53 g of 9-phenyl-9H-carbazol-1-yl) boronic acid and 90 g of 1-iodo-2-nitrobenzene were dissolved in 1500 ml of toluene, to which 540 ml of K 2 CO 3 (2M) 3 ) 4 12.5 g were added and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 105.4 g (yield: 80%) of intermediate A3-1.
[A3의 합성] [Synthesis of A3]
상기 A3-1 105 g을 1,2-dichlorobenzene 530 ml에 녹인 후 P(OEt)3 290 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 A3 39.2 g (수율 41%)를 얻었다.105 g of A3-1 was dissolved in 530 ml of 1,2-dichlorobenzene, 290 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 39.2 g (41%) of intermediate A3.
[중간체 B1의 합성] [Synthesis of intermediate B1]
[B1-1의 합성] [Synthesis of B1-1]
둥근바닥플라스크에 benzofuran-3-ylboronic acid 78.5 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B1-1 78.7 g (수율 82%)를 얻었다.Reflux, insert the benzofuran-3-ylboronic acid 78.5 g , 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, 1000 ml K 2 CO 3 (2M ) 600 ml , and Pd (PPh 3) 4 13.9 g round bottom flask Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 78.7 g (yield 82%) of intermediate B1-1.
[B1의 합성] [Synthesis of B1]
상기 B1-1 78 g을 1,2-dichlorobenzene 400 ml에 녹인 후 P(OEt)3 260 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 B1 36.4 g (수율 54%)를 얻었다.78 g of the above B1-1 was dissolved in 400 ml of 1,2-dichlorobenzene, 260 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 36.4 g (yield: 54%) of Intermediate B1.
[중간체 B2의 합성][Synthesis of intermediate B2]
[B2-1의 합성] [Synthesis of B2-1]
둥근바닥플라스크에 benzo[b]thiophen-3-ylboronic acid 87.7 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B2-1 82 g (수율 80%)를 얻었다.To a round bottom flask was added benzo [b] thiophen-3- ylboronic acid 87.7 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, 1000 ml K 2 CO 3 (2M ) 600 ml , and Pd (PPh 3) 4 13.9 g And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 82 g (yield 80%) of intermediate B2-1.
[B2의 합성] [Synthesis of B2]
상기 B2-1 80 g을 1,2-dichlorobenzene 400 ml에 녹인 후 P(OEt)3 310 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 B2 39.8 g (수율 57%)를 얻었다.80 g of B2-1 was dissolved in 400 ml of 1,2-dichlorobenzene, 310 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 39.8 g (yield: 57%) of Intermediate B2.
[중간체 B3의 합성][Synthesis of intermediate B3]
[B3-1의 합성] [Synthesis of B3-1]
둥근바닥플라스크에 (1-phenyl-1H-indol-3-yl)boronic acid 102.8 g, 1-iodo-2-nitrobenzene 90 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 540 ml와 Pd(PPh3)4 12.5 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B3-1 93.1 g (수율 82%)를 얻었다.102.8 g of 1-phenyl-1H-indol-3-yl) boronic acid and 90 g of 1-iodo-2-nitrobenzene were dissolved in 1000 ml of toluene, and 540 ml of K 2 CO 3 (2M) and Pd 3 ) 4 12.5 g were added and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 93.1 g (yield 82%) of intermediate B3-1.
[B3의 합성] [Synthesis of B3]
상기 B3-1 93 g을 1,2-dichlorobenzene 460 ml에 녹인 후 P(OEt)3 290 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 B3 40.9 g (수율 49%)를 얻었다.93 g of B3-1 was dissolved in 460 ml of 1,2-dichlorobenzene, 290 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 40.9 g (yield 49%) of intermediate B3.
[중간체 B6의 합성][Synthesis of intermediate B6]
[B6-1의 합성] [Synthesis of B6-1]
둥근바닥플라스크에 benzofuran-2-ylboronic acid 78.5 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B6-1 81.6 g (수율 85%)를 얻었다.Reflux, insert the benzofuran-2-ylboronic acid 78.5 g , 1-iodo-2-nitrobenzene 100 g of K 2 CO 3 (2M) 600 ml , and Pd (PPh 3) 4 13.9 g is dissolved in toluene, 1000 ml round bottom flask Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 81.6 g (yield 85%) of intermediate B6-1.
[B6의 합성] [Synthesis of B6]
상기 B6-1 78 g을 1,2-dichlorobenzene 410 ml에 녹인 후 P(OEt)3 330 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 42.1 g (수율 60%)를 얻었다.78 g of B6-1 was dissolved in 410 ml of 1,2-dichlorobenzene, 330 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 42.1 g (yield: 60%) of the intermediate.
[중간체 B7의 합성][Synthesis of intermediate B7]
[B7-1의 합성] [Synthesis of B7-1]
둥근바닥플라스크에 benzo[b]thiophen-2-ylboronic acid 85.7 g, 1-iodo-2-nitrobenzene 100 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 600 ml와 Pd(PPh3)4 13.9 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B7-1 80.9 g (수율 79%)를 얻었다.To a round bottom flask was added benzo [b] thiophen-2- ylboronic acid 85.7 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, 1000 ml K 2 CO 3 (2M ) 600 ml , and Pd (PPh 3) 4 13.9 g And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 80.9 g (yield: 79%) of Intermediate B7-1.
[B7의 합성] [Synthesis of B7]
상기 B7-1 80 g을 1,2-dichlorobenzene 400 ml에 녹인 후 P(OEt)3 310 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 B7 38.5 g (수율 55%)를 얻었다.80 g of B7-1 was dissolved in 400 ml of 1,2-dichlorobenzene, 310 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 38.5 g (yield: 55%) of Intermediate B7.
[중간체 B8의 합성][Synthesis of intermediate B8]
[B8-1의 합성] [Synthesis of B8-1]
둥근바닥플라스크에 (1-phenyl-1H-indol-2-yl)boronic acid 102.8 g, 1-iodo-2-nitrobenzene 90 g을 톨루엔 1000 ml에 녹이고 K2CO3(2M) 540 ml와 Pd(PPh3)4 12.5 g을 넣은 후 환류 교반하였다. TLC로 반응을 확인하고 물을 첨가 후 반응을 종결시켰다. 유기층을 EA로 추출하고 감압여과한 후 컬럼정제하여 중간체 B8-1 87.5 g (수율 77%)를 얻었다.In a round bottom flask, 102.8 g of 1-phenyl-1H-indol-2-yl boronic acid and 90 g of 1-iodo-2-nitrobenzene were dissolved in 1000 ml of toluene, and 540 ml of K 2 CO 3 (2M) 3 ) 4 12.5 g were added thereto, followed by reflux stirring. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 87.5 g (yield 77%) of intermediate B8-1.
[B8의 합성] [Synthesis of B8]
상기 B8-1 87 g을 1,2-dichlorobenzene 430 ml에 녹인 후 P(OEt)3 270 ml를 첨가하여 환류 교반하였다. 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 B8 25.7g (수율 33%)를 얻었다.87 g of the above B8-1 was dissolved in 430 ml of 1,2-dichlorobenzene, 270 ml of P (OEt) 3 was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 25.7 g (yield 33%) of Intermediate B8.
상기 중간체 합성법을 이용하여 출발물질을 달리하여 하기 중간체들을 합성한다. The following intermediates are synthesized by different starting materials using the above intermediate synthesis method.
실시예 1: 화합물 1의 합성Example 1: Synthesis of Compound 1
상기 중간체 A3 4.0 g, 1-bromo-3-iodobenzene 4.1 g, t-BuONa 1.7 g, Pd2(dba)3 0.45 g, (t-Bu)3P 0.6 ml를 톨루엔 60 ml에 녹인 후 환류 교반하였다. TLC로 반응 종결을 확인한 후 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 중간체 1-1 2.05 g (수율 35%)를 얻었다.4.0 g of the intermediate A3, 4.1 g of 1-bromo-3-iodobenzene, 1.7 g of t-BuONa, 0.45 g of Pd 2 (dba) 3 and 0.6 ml of (t-Bu) 3 P were dissolved in 60 ml of toluene, . After completion of the reaction was confirmed by TLC, the organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 2.05 g (yield: 35%) of Intermediate 1-1.
상기 중간체 1-1 2.05 g, 중간체B1 2.05 g, t-BuONa 0.61 g, Pd2(dba)3 0.15 g, (t-Bu)3P 0.2 ml를 톨루엔 30 ml에 녹인 후 환류 교반하였다. TLC로 반응 종결을 확인한 후 유기층을 MC로 추출하고 감압여과한 후 컬럼정제하여 화합물 1 1.34 g (수율 52%)를 얻었다.2.05 g of Intermediate 1-1, 2.05 g of Intermediate B1, 0.61 g of t-BuONa, 0.15 g of Pd 2 (dba) 3 and 0.2 ml of (t-Bu) 3 P were dissolved in 30 ml of toluene and the mixture was stirred under reflux. After completion of the reaction was confirmed by TLC, the organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain Compound 1 (1.34 g, yield 52%).
m/z: 613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%), 614.21 (1.1%)m / z: 613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%), 614.21
실시예 2: 화합물 2의 합성Example 2: Synthesis of Compound 2
중간체 A3 대신 중간체 A1을 이용한 것을 제외하고는 화합물 1과 같은 방법으로 화합물 2를 합성하였다. Compound 2 was synthesized in the same manner as Compound 1 except that Intermediate A1 was used instead of Intermediate A3.
m/z: 538.17 (100.0%), 539.17 (42.2%), 540.17 (8.9%), 541.18 (1.3%)m / z: 538.17 (100.0%), 539.17 (42.2%), 540.17 (8.9%), 541.18
실시예 3: 화합물 3의 합성Example 3: Synthesis of Compound 3
중간체 A3 대신 중간체 A2, 중간체 B1 대신 B2를 이용한 것을 제외하고는 화합물1과 같은 방법으로 화합물 3을 합성하였다. Compound 3 was synthesized in the same manner as Compound 1, except that Intermediate A2 was used instead of Intermediate A3, and B2 was used instead of Intermediate B1.
m/z: 570.12 (100.0%), 571.13 (41.4%), 572.12 (9.4%), 572.13 (9.0%), 573.12 (3.9%), 571.12 (2.3%), 573.13 (1.3%)m / z: 570.12 (100.0%), 571.13 (41.4%), 572.12 (9.4%), 572.13 (9.0%), 573.12 (3.9%
실시예 4: 화합물 4의 합성Example 4: Synthesis of Compound 4
중간체 B1 대신 B8을 이용한 것을 제외하고는 화합물 1과 같은 방법으로 화합물 4를 합성하였다. Compound 4 was synthesized in the same manner as Compound 1, except that B8 was used instead of Intermediate B1.
m/z: 688.26 (100.0%), 689.27 (54.4%), 690.27 (14.5%), 691.27 (2.7%), 689.26 (1.5%)m / z: 688.26 (100.0%), 689.27 (54.4%), 690.27 (14.5%), 691.27 (2.7%), 689.26
실시예 5: 화합물 5의 합성Example 5: Synthesis of Compound 5
중간체 B1 대신 B6를 이용한 것을 제외하고는 화합물 1과 같은 방법으로 화합물5를 합성하였다. Compound 5 was synthesized in the same manner as Compound 1 except that B6 was used instead of Intermediate B1.
m/z: 613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%), 614.21 (1.1%)m / z: 613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%), 614.21
실시예 6: 화합물 6의 합성Example 6: Synthesis of Compound 6
중간체 B1 대신 B7을 이용한 것을 제외하고는 화합물 1과 같은 방법으로 화합물6을 합성하였다. Compound 6 was synthesized in the same manner as Compound 1 except that B7 was used instead of Intermediate B1.
m/z: 629.19 (100.0%), 630.20 (47.9%), 631.20 (11.6%), 631.19 (5.1%), 632.19 (2.2%), 630.19 (1.9%), 632.20 (1.9%)m / z 629.19 (100.0%), 630.20 (47.9%) 631.20 11.6% 631.19 5.1% 632.19 2.2% 630.19 1.9% 632.20 1.9%
실시예 7: 화합물 7의 합성Example 7: Synthesis of Compound 7
상기 중간체 A3 4.0 g, NaH 0.35 g을 DMF 40 ml에 넣고 교반하였다. 여기에 2,4-dichloro-6-phenyl-1,3,5-triazine 3.26 g을 DMF 35 ml에 녹인 후 천천히 적가하였다. 상온에서 교반 후 TLC로 반응 종결을 확인하고 실리카 필터 후 재결정하여 중간체 7-1 2.70 g (수율 43%)를 얻었다. 4.0 g of the intermediate A3 and 0.35 g of NaH were added to 40 ml of DMF and stirred. 3.26 g of 2,4-dichloro-6-phenyl-1,3,5-triazine was dissolved in 35 ml of DMF and then slowly added dropwise. After stirring at room temperature, the reaction was terminated by TLC, and the reaction mixture was recrystallized after silica filtration to obtain 2.70 g (yield: 43%) of Intermediate 7-1.
상기 중간체 B1 0.90 g, NaH 0.13 g을 DMF 10 ml에 넣고 교반하였다. 여기에 중간체 7-1 2.72g 을 DMF 30 ml에 녹인 후 천천히 적가하였다. 상온에서 교반 후 TLC로 반응 종결을 확인하고 실리카 필터 후 재결정하여 화합물 7 1.56 g (수율 52%)를 얻었다. 0.90 g of Intermediate B1 and 0.13 g of NaH were added to 10 ml of DMF and stirred. 2.72 g of Intermediate 7-1 was dissolved in 30 ml of DMF, and then slowly added dropwise. After stirring at room temperature, the reaction was terminated by TLC, and the reaction mixture was filtered through silica and recrystallized to obtain 1.56 g (yield: 52%) of Compound 7.
m/z: 692.23 (100.0%), 693.24 (51.2%), 694.24 (13.0%), 695.24 (2.4%), 693.23 (2.2%), 694.23 (1.1%)m / z 692.23 (100.0%) 693.24 (51.2%) 694.24 13.0% 695.24 2.4% 693.23 2.2% 694.23 1.1%
실시예 8: 화합물 8의 합성Example 8: Synthesis of Compound 8
중간체 B1 대신 B2를 이용한 것을 제외하고는 화합물 7과 같은 방법으로 화합물 8을 합성하였다. Compound 8 was synthesized in the same manner as Compound 7, except that B2 was used instead of Intermediate B1.
m/z: 708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%), 711.21 (2.6%), 711.22 (2.2%)m / z: 708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%), 711.21
실시예 9: 화합물 9의 합성Example 9: Synthesis of Compound 9
중간체 A3 대신 A1을 이용한 것을 제외하고는 화합물 7과 같은 방법으로 화합물9를 합성하였다. Compound 9 was synthesized in the same manner as Compound 7 except that Al was used instead of Intermediate A3.
m/z: 617.19 (100.0%), 618.19 (44.7%), 619.19 (11.0%), 618.18 (1.8%), 620.20 (1.4%)m / z: 617.19 (100.0%), 618.19 (44.7%), 619.19 (11.0%), 618.18 (1.8%
실시예 10: 화합물 10의 합성Example 10: Synthesis of
중간체 A3 대신 중간체 A2, 중간체 B1 대신 B2를 이용한 것을 제외하고는 화합물7과 같은 방법으로 화합물10을 합성하였다.
m/z: 649.14 (100.0%), 650.14 (47.8%), 651.14 (10.6%), 651.15 (9.7%), 652.14 (4.2%), 652.15 (1.5%)m / z: 649.14 (100.0%), 650.14 (47.8%), 651.14 (10.6%), 651.15 (9.7%), 652.14 (4.2%
실시예 11: 화합물 11의 합성Example 11: Synthesis of
중간체 A3 대신 중간체 A18을 이용한 것을 제외하고는 화합물 7과 같은 방법으로 화합물 11을 합성하였다.
m/z: 692.23 (100.0%), 693.24 (51.2%), 694.24 (13.0%), 695.24 (2.4%), 693.23 (2.2%), 694.23 (1.1%)m / z 692.23 (100.0%) 693.24 (51.2%) 694.24 13.0% 695.24 2.4% 693.23 2.2% 694.23 1.1%
실시예 12: 화합물 12의 합성Example 12: Synthesis of
중간체 A3 대신 중간체 A18, 중간체 B1 대신 B2를 이용한 것을 제외하고는 화합물 7과 같은 방법으로 화합물 12를 합성하였다.
m/z: 708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%), 711.21 (2.6%), 711.22 (2.2%)m / z: 708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%), 711.21
유기발광소자의 제조Manufacture of organic light emitting device
도 1에 기재된 구조에 따라 유기발광소자를 제조하였다. 유기발광소자는 아래로부터 양극(정공주입전극(11))/정공주입층(12)/정공수송층(13)/발광층(14)/전자전달층(15)/음극(전자주입전극(16)) 순으로 적층시켰다.
An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device includes an anode (hole injecting electrode 11) / a
실시예 및 비교예의 정공주입층(12), 정공전달층(13), 발광층(14), 전자전달층(15)는 아래과 같은 물질을 사용하였다.
The following materials were used for the
실시예 13Example 13
인듐틴옥사이드(ITO)가 1500Å 두께가 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 ITO 기판 상부에 열 진공 증착기(thermal evaporator)를 이용하여 정공주입층 HT01 600Å, 정공수송층으로 NPB 250 Å를 제막하였다. 다음으로 발광층으로 상기 화합물 1 : Ir(ppy)3 10%로 도핑하여 250 Å 제막하였다. 다음으로 전자전달층으로 ET01:Liq(1:1) 300 Å 제막한 후 LiF 10 Å, 알루미늄(Al) 1000 Å 제막하고, 이 소자를 글로브박스에서 밀봉(Encapsulation)함으로써 녹색 유기발광소자를 제작하였다.A thin glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form a hole injection layer HT01 600 Å and a hole transport layer NPB 250 Å. Next, the compound 1 was doped with 10% of Ir (ppy) 3 as a light emitting layer to form a 250 Å film. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer,
실시예 14 내지 실시예 24Examples 14 to 24
실시예 13과 같은 방법으로 발광층 호스트로 각각 화합물 2 내지 12을 사용하여 제막한 녹색 유기발광소자를 제작하였다. A green organic luminescent device was fabricated in the same manner as in Example 13 by using the compounds 2 to 12 as a luminescent layer host.
비교예 1 Comparative Example 1
상기 실시예 1의 발광층 호스트로 화합물 1을 대신하여 CBP로 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다. A green organic light emitting device was fabricated in the same manner as in Example 1 except that CBP was used instead of Compound 1 as the light emitting layer host.
비교예 2 Comparative Example 2
상기 실시예 1의 발광층 호스트로 화합물 1을 대신하여 비교화합물 1로 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다. A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1 was used instead of Compound 1 as the light emitting layer host.
비교예 3Comparative Example 3
상기 실시예 1의 발광층 호스트로 화합물 1을 대신하여 비교화합물 2를 사용한 것을 제외하고는 동일한 방법으로 녹색 유기발광소자를 제작하였다. A green organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 1 was replaced with the compound 2 as the light emitting layer host.
유기발광소자의 성능평가Evaluation of performance of organic light emitting device
키슬리 2400 소스 메져먼트 유닛(Kiethley 2400 source measurement unit) 으로 전압을 인가하여 전자 및 정공을 주입하고 코니카 미놀타(Konica Minolta) 분광복사계(CS-2000)를 이용하여 빛이 방출될 때의 휘도를 측정함으로써, 실시예 및 비교예의 유기발광소자의 성능을 인가전압에 대한 전류 밀도 및 휘도를 대기압 조건하에 측정하여 평가하였으며, 그 결과를 표 1에 나타내었다. A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.
1000nitlife span@
1000nit
상기 표 1에 나타나는 바와 같이 본 발명의 실시예는 비교예 1 내지 3에 비하여 모든 면에서 유기발광소자 물성이 우수함을 확인할 수 있다. As shown in Table 1, it can be confirmed that the embodiments of the present invention are superior to the organic EL devices in all aspects in comparison with Comparative Examples 1 to 3.
Claims (8)
[화학식 1]
A-L-B
상기 식에서,
A는 하기 A1 내지 A30으로 표시되는 구조 중 하나이며, 여기서 A에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있으며,
L은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C2-50의 헤테로아릴기이고,
B는 하기 B1 내지 B10으로 표시되는 구조 중 하나이며, 여기서 B에 포함된 수소는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않을 수 있다.
상기 구조들에서, -*는 결합부위이고, Ar1 및 Ar2는 각각 독립적으로 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이다.A luminescent compound represented by the following formula (1):
[Chemical Formula 1]
ALB
In this formula,
A is one of the structures represented by the following formulas A1 to A30, wherein each of the hydrogen atoms contained in A may independently be substituted or unsubstituted with a deuterium, a halogen, an amino group, a nitrile group, a nitro group,
L is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, C 1-30, C 6-30 An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group unsubstituted or substituted with a C 2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1-30 alkyl group, a C 2-30 alkenyl group, an alkoxy group an alkynyl group, a C 1-30 of C 2-30, aryl of C 6-30 An aryl group of C 6-30 , or a C 2-50 heteroaryl group which is unsubstituted or substituted with a C 2-30 heteroaryl group,
B is one of the structures represented by the following formulas B1 to B10, wherein each of the hydrogen atoms contained in B may independently be substituted or unsubstituted with deuterium, halogen, amino, nitrile or nitro.
In the above structures, - is a bonding site, Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile or nitro.
하기 화학식들 중 어느 하나로 표시되는 것을 특징으로 하는 발광 화합물:
상기에서 X1 및 X2는 각각 독립적으로 S, O, Se, Te 또는 N-Ar3이며, 여기서 Ar3은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이며,
Ar은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, C6-30의 아릴기, 또는 C2-30의 헤테로아릴기로 치환되거나 치환되지 않은 C6-50의 헤테로아릴기이다.The method according to claim 1,
A luminescent compound represented by any one of the following formulas:
Wherein X 1 and X 2 are each independently S, O, Se, Te or N-Ar 3 wherein Ar 3 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group,
Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, C 1-30, C 6-30 of An aryloxy group, a C 6-30 aryl group, or a C 6-50 aryl group unsubstituted or substituted with a C 2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1-30 alkyl group, a C 2-30 alkenyl group, an alkoxy group an alkynyl group, a C 1-30 of C 2-30, aryl of C 6-30 An aryl group of C 6-30 , or a C 6-50 heteroaryl group which is unsubstituted or substituted with a C 2-30 heteroaryl group.
하기 화학식들 중 어느 하나로 표시되는 것을 특징으로 하는 발광 화합물:
상기에서 X1 및 X2는 각각 독립적으로 S, O, Se, Te 또는 N-Ar4이며, 여기서 Ar4는 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이며,
Y는 CR1 또는 N이며 여기서 R1은 수소; 중수소; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알킬기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알케닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 알키닐기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C1-30의 알콕시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴옥시기; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C6-30의 아릴기; 또는 중수소, 할로겐, 아미노기, 니트릴기, 니트로기로 치환되거나 치환되지 않은 C2-30의 헤테로아릴기이다. The method according to claim 1,
A luminescent compound represented by any one of the following formulas:
Wherein X 1 and X 2 are each independently S, O, Se, Te or N-Ar 4 , wherein Ar 4 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group,
Y is CR 1 or N, where R 1 is hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C 1-30 alkyl group unsubstituted or substituted with a nitro group; A C 2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C 6-30 aryloxy group optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C 6-30 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C 2-30 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile or nitro.
상기 L은 하기 구조들 중 어느 하나로 표시되는 것을 특징으로 하는 발광 화합물:
Wherein L is represented by any one of the following structures:
하기 화학식들 중 어느 하나로 표시되는 것을 특징으로 하는 발광 화합물:
A luminescent compound represented by any one of the following formulas:
[반응식 1]
상기 반응식 1에서 A, L, B는 화학식 1에서 정의한 바와 같다.1. A process for preparing a compound represented by the formula (1), which comprises the steps of:
[Reaction Scheme 1]
In the above Reaction Scheme 1, A, L, and B are as defined in Chemical Formula (1).
상기 유기물층이 제1항의 화합물을 발광 호스트 또는 도펀트로서 함유하는 것을 특징으로 하는 유기발광소자.8. The method of claim 7,
Wherein the organic material layer contains the compound of claim 1 as a light emitting host or a dopant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2014/011225 WO2015076599A1 (en) | 2013-11-20 | 2014-11-20 | Novel light emission compound and organic light emitting device comprising same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130141068 | 2013-11-20 | ||
| KR20130141068 | 2013-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150058084A true KR20150058084A (en) | 2015-05-28 |
| KR102388406B1 KR102388406B1 (en) | 2022-04-20 |
Family
ID=53392725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140162365A KR102388406B1 (en) | 2013-11-20 | 2014-11-20 | Novel electroluminescent compound and organic electroluminescent device comprising same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102388406B1 (en) |
| CN (1) | CN105765030B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018056536A (en) * | 2016-09-23 | 2018-04-05 | 日本放送協会 | Organic electroluminescent element |
| KR20200099965A (en) | 2019-02-15 | 2020-08-25 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012050003A1 (en) * | 2010-10-13 | 2012-04-19 | 新日鐵化学株式会社 | Organic electroluminescent element |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101212670B1 (en) * | 2009-11-03 | 2012-12-14 | 제일모직주식회사 | Composition for organic photoelectric device, organic photoelectric device using the same and display device comprising the same |
| DE102010033548A1 (en) * | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materials for electronic devices |
| EP2628743B1 (en) * | 2010-10-13 | 2016-02-24 | Nippon Steel & Sumikin Chemical Co., Ltd. | Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device |
| JP5887771B2 (en) * | 2011-09-07 | 2016-03-16 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR PRODUCING ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE, LIGHTING DEVICE, AND COMPOUND |
-
2014
- 2014-11-20 CN CN201480063382.0A patent/CN105765030B/en active Active
- 2014-11-20 KR KR1020140162365A patent/KR102388406B1/en active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012050003A1 (en) * | 2010-10-13 | 2012-04-19 | 新日鐵化学株式会社 | Organic electroluminescent element |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018056536A (en) * | 2016-09-23 | 2018-04-05 | 日本放送協会 | Organic electroluminescent element |
| KR20200099965A (en) | 2019-02-15 | 2020-08-25 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105765030B (en) | 2018-07-17 |
| KR102388406B1 (en) | 2022-04-20 |
| CN105765030A (en) | 2016-07-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20240149861A (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20230164634A (en) | Novel compound and organic electroluminescent device comprising same | |
| KR102585105B1 (en) | Novel compound and organic electroluminescent device comprising same | |
| WO2011105161A1 (en) | Organic electroluminescent element | |
| KR102671576B1 (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20160132344A (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20140020208A (en) | Organic electroluminescent compound comprising acridine derivative and organic electroluminescent device comprising same | |
| KR102402220B1 (en) | Novel blue fluorescent host compound and organic electroluminescent device comprising same | |
| KR20140015202A (en) | Organic electroluminescent compound comprising acridine derivative and organic electroluminescent device comprising same | |
| KR102659372B1 (en) | Novel compound and organic electroluminescent device comprising the same | |
| KR102387855B1 (en) | Novel electroluminescent compound and organic electroluminescent device comprising same | |
| KR102448875B1 (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20150058082A (en) | Novel electroluminescent compound and organic electroluminescent device comprising same | |
| KR20180020577A (en) | Novel compound and organic electroluminescent device comprising the same | |
| KR102394380B1 (en) | Novel electroluminescent compound and organic electroluminescent device comprising same | |
| KR102447718B1 (en) | Novel electroluminescent compound and organic electroluminescent device comprising same | |
| KR102423699B1 (en) | Novel compound and organic electroluminescent device comprising same | |
| CN105745301B (en) | Novel light-emitting compound and organic light-emitting element comprising same | |
| KR20140086880A (en) | Novel organic compound and organic electroluminescent device comprising same | |
| KR102429520B1 (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20180041477A (en) | Novel compound and organic electroluminescent device comprising the same | |
| KR20150132020A (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20180020578A (en) | Novel compound and organic electroluminescent device comprising the same | |
| KR20170052777A (en) | Novel compound and organic electroluminescent device comprising same | |
| KR20160045019A (en) | Novel compound and organic electroluminescent device comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right |