WO2014157933A1 - 신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자 - Google Patents
신규한 벤조펜안트렌 유도체 화합물 및 이를 이용한 유기발광소자 Download PDFInfo
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- WO2014157933A1 WO2014157933A1 PCT/KR2014/002538 KR2014002538W WO2014157933A1 WO 2014157933 A1 WO2014157933 A1 WO 2014157933A1 KR 2014002538 W KR2014002538 W KR 2014002538W WO 2014157933 A1 WO2014157933 A1 WO 2014157933A1
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- -1 benzophenanthrene derivative compound Chemical class 0.000 title abstract description 50
- 238000002347 injection Methods 0.000 claims description 35
- 239000007924 injection Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 238000001771 vacuum deposition Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 description 107
- 238000003786 synthesis reaction Methods 0.000 description 105
- 239000010410 layer Substances 0.000 description 95
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 34
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 27
- 0 CC(CCC1C23)CC1C(CCC1)=C1C2C3C(CC1CC2)=C(CCC=*3)C3=C1c1*2cc(C(C)(C)C)cc1 Chemical compound CC(CCC1C23)CC1C(CCC1)=C1C2C3C(CC1CC2)=C(CCC=*3)C3=C1c1*2cc(C(C)(C)C)cc1 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000151 deposition Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- CAVFZRHGFPBZSK-UHFFFAOYSA-N 5-bromo-7,8-dihydrobenzo[c]phenanthrene Chemical compound BrC=1C=2C=CC=CC2C=2C3=C(CCC2C1)C=CC=C3 CAVFZRHGFPBZSK-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KKSMABQPCZBZJR-UHFFFAOYSA-N 7,8-dihydrobenzo[c]phenanthrene Chemical compound C1=CC=C2CCC3=CC=C(C=CC=C4)C4=C3C2=C1 KKSMABQPCZBZJR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- XCDJOJRRJCCSAN-UHFFFAOYSA-N 3,8-dibromo-5,6-dihydrobenzo[c]phenanthrene Chemical compound BrC=1C=CC2=C(CCC=3C=C(C=4C=CC=CC4C23)Br)C1 XCDJOJRRJCCSAN-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QNAZPKJWQFOAGG-UHFFFAOYSA-N 3-ethynyl-4-phenyl-1,2-dihydronaphthalene Chemical compound C12=CC=CC=C2CCC(C#C)=C1C1=CC=CC=C1 QNAZPKJWQFOAGG-UHFFFAOYSA-N 0.000 description 3
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- SZERENLAQLJWNZ-UHFFFAOYSA-N 7,8-dihydrobenzo[c]phenanthren-6-ylboronic acid Chemical compound C1=CC=CC=2C=C(C=3CCC=4C=CC=CC4C3C21)B(O)O SZERENLAQLJWNZ-UHFFFAOYSA-N 0.000 description 2
- JSWABOAPTFWBKK-UHFFFAOYSA-N 7,8-dihydrobenzo[g]phenanthren-3-ylboronic acid Chemical compound C1=CC(=CC=2C=CC=3CCC=4C=CC=CC4C3C21)B(O)O JSWABOAPTFWBKK-UHFFFAOYSA-N 0.000 description 2
- SUTDZHOCNHPNDS-UHFFFAOYSA-N 9-phenyl-3-[3-(9-phenylcarbazol-3-yl)-5,6-dihydrobenzo[c]phenanthren-8-yl]carbazole Chemical compound C1=CC(=CC=2CCC=3C=C(C=4C=CC=CC4C3C21)C=2C=CC=1N(C3=CC=CC=C3C1C2)C2=CC=CC=C2)C=2C=CC=1N(C3=CC=CC=C3C1C2)C2=CC=CC=C2 SUTDZHOCNHPNDS-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 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 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water 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
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 2
- YGVDBZMVEURVOW-UHFFFAOYSA-N (10-naphthalen-2-ylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 YGVDBZMVEURVOW-UHFFFAOYSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- UPFTWKGGLHJPJX-UHFFFAOYSA-N 1-N,2,4-triphenylbenzene-1,3-diamine Chemical group C1(=CC=CC=C1)NC1=C(C(=C(C=C1)C1=CC=CC=C1)N)C1=CC=CC=C1 UPFTWKGGLHJPJX-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- NTYDMFCZXBCEJY-UHFFFAOYSA-N 1-methyl-2-phenylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC=CC=C1C1=CC=CC=C1 NTYDMFCZXBCEJY-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
- FYKJPLLUCCMVTQ-UHFFFAOYSA-N 1-n-naphthalen-1-yl-4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 FYKJPLLUCCMVTQ-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- YOZHUJDVYMRYDM-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-naphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C(=CC(NC=3C=CC=CC=3)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 YOZHUJDVYMRYDM-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-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
- JATHOYVVNVXTAV-UHFFFAOYSA-N 4-chloro-5,6-dihydrobenzo[c]phenanthrene Chemical compound ClC1=CC=CC2=C1CCC=1C=CC=3C=CC=CC=3C2=1 JATHOYVVNVXTAV-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a novel benzophenanthrene derivative compound and an organic light emitting device using the same, and more particularly, to a benzophenanthrene derivative compound capable of manufacturing an organic light emitting device having excellent characteristics such as driving voltage, luminous efficiency and color purity. It relates to an organic light emitting device using the same.
- the organic light emitting device capable of low-voltage driving by self-emission type has excellent viewing angle, contrast ratio, and the like, and requires no backlight, and is light and thin, and consumed, compared to the liquid crystal display (LCD) which is the mainstream of flat panel display devices. It is also attracting attention as a next-generation display device because it is advantageous in terms of power and has a wide range of color reproduction.
- LCD liquid crystal display
- the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode) and an organic layer between the two electrodes.
- the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML). It may include an electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the light emission characteristics of the light emitting layer.
- a light emitting layer may be doped into the light emitting layer (host).
- the present invention to solve the problems of the prior art as described above is an organic light emitting device comprising a benzophenanthrene derivative compound and the benzophenanthrene derivative compound which can improve the characteristics such as driving voltage, luminous efficiency, color purity of the organic light emitting device
- the purpose is to provide.
- the present invention provides a benzophenanthrene derivative compound represented by the following formula (1):
- R 1 to R 14 are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 40 aryl groups, substituted or unsubstituted hetero aryl groups having 3 to 40 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C3-C20 cycloalkylamino group, substituted or unsubstituted C3-C20 heterocycloalkylamino group, substituted or unsubstituted C6-C30
- the present invention provides an organic light emitting device comprising the benzophenanthrene derivative compound.
- the organic light emitting device using the novel benzophenanthrene derivative compound of the present invention has excellent effects such as driving voltage, luminous efficiency and color purity.
- FIG. 1 is a cross-sectional view showing the structure of an organic light emitting device according to an embodiment of the present invention.
- the present invention provides a benzophenanthrene derivative compound represented by Formula 1 below:
- R 1 to R 14 are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 40 aryl groups, substituted or unsubstituted hetero aryl groups having 3 to 40 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C3-C20 cycloalkylamino group, substituted or unsubstituted C3-C20 heterocycloalkylamino group, substituted or unsubstituted C6-C30
- alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl groups ", substituted or unsubstituted amino groups (-NH2, -NH (R), -N (R ') (R”), wherein R, R' and R "are each independently from 1 to 24 alkyl group (in this case referred to as
- aryl group which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group
- an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl
- alkenyl group which is a substituent used in the compound of the present invention, include an alkenyl group in which an aryl group such as a stybenyl group and a styrenyl group are connected, and specific examples of the cycloalkyl group include a cichloropentyl group and a cyclohexyl group. It is not limited.
- the arylamine group which is a substituent used in the compound of the present invention is a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a dianthracenylamine Group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine group, 9-methyl- anthracenylamine group, ditolyl amine group, phenyl tolyl amine group, triphenylamino A phenylamine group, a phenyl biphenylamino phenyl amine group, a naphthyl phenylaminophenyl biphenylamine group, etc. are mentioned, but it is not limited to this.
- substituted or unsubstituted refers to a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an alkylamino group, an arylamino group, a heteroaryl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of aralkylamino group, alkylsilyl group, arylsilyl group, aryloxy group, aryl group, heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium. .
- benzophenanthrene derivative compound of the present invention is preferably selected from the group represented by the following formula, but is not limited thereto.
- the benzophenanthrene derivative compound can be prepared through the production method of the following schematic diagram.
- the present invention provides an organic light emitting device comprising the benzophenanthrene derivative compound.
- the organic light emitting device of the present invention comprises at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode,
- the phenanthrene derivative compound is characterized in being included in at least one of the layers.
- the benzophenanthrene derivative compound according to the present invention is preferably included in the light emitting layer between the anode and the cathode.
- the layer between the anode and the cathode may be formed by a deposition method or a solution process.
- the present invention can be used in various ways, such as a display device, a display device and a monochromatic or white lighting device including the organic light emitting device.
- a hole injection layer HIL
- HTL hole transport layer
- EML emission layer
- ETL electron transport layer
- EIL electron injection layer
- an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
- the substrate may be a substrate used in a conventional organic light emitting device, in particular, it is preferable to use an organic substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
- the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
- the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
- HIL hole injection layer
- LB Langmuir-Blodgett
- 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 generally, a deposition temperature of 50-500 ° C., It is preferable to select suitably from the vacuum degree of 10 -8 -10 -3 torr, the deposition rate of 0.01-100 kPa / sec, and the film thickness of 10 kPa-5micrometer.
- the hole injection layer material may be a known material, for example TCTA (4,4 ', 4 "-tree (N), which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Patent No. 4,356,429.
- TCTA 4,4 ', 4 "-tree (N)
- N a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Patent No. 4,356,429.
- HI-406 N1, N1 '-(biphenyl-4,4'-diyl) bis (N1- (naphthalen-1-yl) -N4 , N4-diphenylbenzene-1,4-diamine) may be used as the hole injection layer material.
- a hole transport layer (HTL) material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality, and pin holes are generated. It is preferable to form by the vacuum evaporation method from the point which is difficult.
- the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in a range equivalent to that of the hole injection layer.
- the hole transport layer material is not particularly limited, but may be used by using a compound represented by the formula (1) according to the present invention, or arbitrarily selected from conventional known materials used in the hole transport layer.
- the hole transport material is a carbazole derivative such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N, in addition to the compound represented by Formula 1 according to the present invention '-Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD Ordinary amine derivative etc. which have aromatic condensed ring, such as), etc. can be used.
- the light emitting layer (EML) material may be formed on the hole transport layer by a method such as a vacuum deposition method, a spin coating method, a cast method, an LB method, etc., but it is easy to obtain a uniform film quality and difficult to generate pin holes. It is preferable to form by the vacuum deposition method.
- the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
- the light emitting layer material may be used alone or as a host to the compound represented by the formula (1) of the present invention.
- a phosphorescent or fluorescent dopant and a host may be used together to form a light emitting layer.
- a phosphorescent or fluorescent dopant and a host may be used together to form a light emitting layer.
- the fluorescent dopant IDE102 or IDE105 or BD142, which can be purchased from Idemitsu, may be used.
- green phosphorescent dopant Ir (ppy) 3 (fac-tris (2-phenylpyridine) iridium), FIrpic (iridium (III) bis [(4,6-difluorophenyl) -pyridinato-N, C2 ′] picolinate), a blue phosphorescent dopant, and a red phosphorescent dopant RD61 from UDC, may be commonly vacuum deposited (doped).
- the doping concentration of the dopant is not particularly limited, but the concentration of the dopant with respect to 100 parts by weight relative to the host is preferably 0.01-15 parts by weight.
- the hole-inhibiting material that can be used is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
- an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1), and the like, and typical Balq and phenanthrolines ) -Based compound may be used.
- An electron transport layer (ETL) material is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, or a casting method, and particularly preferably by a vacuum deposition method.
- the electron transport layer material has a function of stably transporting electrons injected from an electron injection electrode (Cathode) is not particularly limited in kind, for example, quinoline derivatives, especially tris (8-quinolinorate) aluminum ( Alq3) can be used.
- an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
- the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
- an electron injection layer (EIL) material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by the vacuum deposition method.
- EIL electron injection layer
- the cathode forming metal is formed on the electron injection layer by a vacuum deposition method or a sputtering method and used as a cathode.
- the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
- a transmissive cathode using ITO and IZO may be used to obtain a top emitting device.
- the organic light emitting device of the present invention has an organic structure of an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), a cathode (cathode) structure
- HIL hole injection layer
- HTL hole transport layer
- EML electron transport layer
- EIL electron injection layer
- cathode cathode
- the thickness of the organic thin film layer formed according to the present invention as described above can be adjusted according to the required degree, preferably 10-1,000 nm, more preferably 20-150 nm.
- reaction solution was poured into 200 ml of cold sodium carbonate (Na 2 CO 3 ) aqueous solution, and 200 ml of additional methylene chloride was added thereto. Stir until gas evolution ceased. After extraction, the aqueous layer was extracted again with 250 ml of methylene chloride. The organic layer was dried over magnesium sulfate (MgSO 4 ), filtered and concentrated to give 10.5 g of red liquid 1-chloro-3,4-dihydro-2-carbaldehyde (1-chloro-3,4-dihydro-2-carbaldehyde). (54.7 mmol, 91.3%) was obtained.
- MgSO 4 magnesium sulfate
- Synthesis was carried out in the same manner as in Synthesis Example 1-6, except that 4-chloro-5,6-dihydrobenzo [c] phenanthrene was used instead of 8-bromo-5,6-dihydrobenzo [c] phenanthrene.
- ADN ADN: 9,10-di (2-naphthyl)-anthracene
- BD142 was used as a dopant material of the light emitting layer.
- An organic light emitting diode was manufactured according to a conventional method using a compound of (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethycrylicene-6,12-diamine). It was.
- a 650 ⁇ hole injection layer (hole injection layer material: HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) on a 1500 ⁇ thick ITO layer (anode) formed on a glass substrate.
- hole injection layer material HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) on a 1500 ⁇ thick ITO layer (anode) formed on a glass substrate.
- the luminescence properties of the organic light emitting diodes were measured and shown in Table 1 below.
- Examples 1 to 15 are similar in voltage to Comparative Example 1, but it can be seen that the current efficiency and luminance are improved up to 1.5 times, and the color coordinates are relatively excellent.
- the compound obtained in Synthesis Examples 18 to 23 was used as the light emitting dopant material of the light emitting layer, and the compound of BD142 was used as the comparative dopant material, and ADN (ADN: 9,10-di (2-naphthyl) ) It was prepared in the same manner as in Example except that ananthracene) was used.
- Examples 18 to 23 are superior in driving voltage to Comparative Examples.
- the current efficiency shows similar or low characteristics, but this is a result of moving to the short wavelength region as can be seen from the CIEy value check in the color coordinates, and it shows the characteristics up to 1.6 times when considering conversion efficiency.
- an organic light emitting device having excellent characteristics such as driving voltage, luminous efficiency and color coordinates may be manufactured using the novel benzophenanthrene compound of the present invention.
- the organic light emitting device using the novel benzophenanthrene derivative compound of the present invention has excellent effects such as driving voltage, luminous efficiency and color purity.
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Abstract
Description
분류 | 호스트 | 전압(V) | 전류효율(cd/A) | 휘도(cd/m2) | CIEx | CIEy |
실시예1 | 합성예1 | 5.44 | 9.44 | 944 | 0.135 | 0.175 |
실시예2 | 합성예2 | 5.59 | 9.62 | 962 | 0.146 | 0.177 |
실시예3 | 합성예3 | 5.51 | 9.55 | 955 | 0.139 | 0.178 |
실시예4 | 합성예4 | 5.65 | 9.43 | 943 | 0.140 | 0.173 |
실시예5 | 합성예5 | 5.66 | 8.89 | 889 | 0.140 | 0.169 |
실시예6 | 합성예6 | 5.61 | 8.86 | 886 | 0.146 | 0.168 |
실시예7 | 합성예7 | 5.62 | 8.53 | 853 | 0.141 | 0.167 |
실시예8 | 합성예8 | 5.55 | 7.95 | 795 | 0.140 | 0.160 |
실시예9 | 합성예9 | 5.70 | 9.30 | 930 | 0.143 | 0.172 |
실시예10 | 합성예10 | 5.65 | 8.98 | 898 | 0.142 | 0.167 |
실시예11 | 합성예11 | 5.65 | 9.11 | 911 | 0.140 | 0.171 |
실시예12 | 합성예12 | 5.73 | 9.21 | 921 | 0.141 | 0.169 |
실시예13 | 합성예13 | 5.52 | 8.88 | 888 | 0.140 | 0.165 |
실시예14 | 합성예14 | 5.50 | 8.73 | 873 | 0.140 | 0.160 |
실시예15 | 합성예15 | 5.63 | 9.20 | 920 | 0.145 | 0.188 |
비교예 | ADN | 5.75 | 6.30 | 630 | 0.141 | 0.169 |
분류 | 도펀트 | 전압(V) | 전류효율(cd/A) | 휘도(cd/m2) | CIEx | CIEy |
실시예18 | 화합물18 | 4.64 | 5.41 | 541 | 0.143 | 0.111 |
실시예19 | 화합물19 | 4.34 | 5.78 | 578 | 0.146 | 0.111 |
실시예20 | 화합물20 | 4.55 | 5.94 | 594 | 0.139 | 0.122 |
실시예21 | 화합물21 | 4.88 | 6.43 | 643 | 0.140 | 0.124 |
실시예22 | 화합물22 | 4.72 | 5.79 | 579 | 0.140 | 0.123 |
실시예23 | 화합물23 | 4.11 | 5.86 | 586 | 0.146 | 0.101 |
비교예 | BD142 | 5.75 | 6.30 | 630 | 0.141 | 0.169 |
Claims (8)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에서,R1 내지 R14는 각각 독립적으로 치환 또는 비치환의 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로 아릴기, 치환 또는 비치환의 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 시클로알킬아미노기, 치환 또는 비치환의 탄소수 3 내지 20 헤테로시클로알킬아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 헤테로아릴아미노기, 치환 또는 비치환의 탄소수 6 내지 30의 아르알킬아미노기, 치환 또는 비치환의 탄소수 1 내지 30의 알킬실릴기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환의 알케닐기, 치환 또는 비치환의 알키닐기, 시아노기, 할로겐기, 중수소 및 수소로 이루어진 군에서 선택된다.
- 제1항 기재의 화학식 1의 화합물을 포함하는 것을 특징으로 하는 유기발광소자.
- 제4항에 있어서,제1항의 화합물을 상기 애노드와 캐소드 사이의 정공주입층(HIL)또는 정공수송층(HTL) 또는 발광층(EML)에 포함하는 것을 특징으로 하는 유기발광소자.
- 제5항에 있어서,상기 애노드와 캐소드 사이에 발광층, 정공주입층, 정공수송층, 전자저지층, 전자수송층, 전자주입층, 정공저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기발광소자.
- 제4항에 있어서,상기 애노드와 캐소드 사이의 발광층, 정공주입층, 정공수송층, 전자저지층, 전자수송층, 전자주입층, 정공저지층으로부터 선택된 하나 이상의 층은 진공증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기발광소자.
- 제4항에 있어서,상기 유기발광소자는 표시소자, 디스플레이 소자, 조명소자용인 것을 특징으로 하는 유기발광소자.
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