KR101216006B1 - Aromatic compound and organic electroluminescent device using the same - Google Patents
Aromatic compound and organic electroluminescent device using the same Download PDFInfo
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- KR101216006B1 KR101216006B1 KR1020090098697A KR20090098697A KR101216006B1 KR 101216006 B1 KR101216006 B1 KR 101216006B1 KR 1020090098697 A KR1020090098697 A KR 1020090098697A KR 20090098697 A KR20090098697 A KR 20090098697A KR 101216006 B1 KR101216006 B1 KR 101216006B1
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- South Korea
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- carbon atoms
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- light emitting
- substituted
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- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 230000000903 blocking effect Effects 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052805 deuterium Chemical group 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 84
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- -1 sec-butyloxy group Chemical group 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 2
- 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 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- QXRWZCZNVUIAIF-UHFFFAOYSA-N BrC1=CC=C2C=CC3=C(C=CC4=CC=C1C2=C34)C1=CC=C(C=C1)Br Chemical compound BrC1=CC=C2C=CC3=C(C=CC4=CC=C1C2=C34)C1=CC=C(C=C1)Br QXRWZCZNVUIAIF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 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
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 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
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-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
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-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
- 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
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-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
- 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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical class COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 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 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 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
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
본 발명은 하기 화학식 (1)로 표현되는 방향족 화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로서, 본 발명에 따른 방향족 화합물을 포함하는 유기전계발광소자는 휘도 및 색순도 특성이 우수한 효과가 있다.The present invention relates to an aromatic compound represented by the following formula (1) and an organic electroluminescent device comprising the same, the organic electroluminescent device comprising an aromatic compound according to the present invention has an excellent brightness and color purity characteristics.
(1)(One)
(상기 식에서, L, A1 내지 A4는 발명의 상세한 설명 또는 청구범위에 정의된 바와 같다)Wherein L, A 1 to A 4 are as defined in the description or claims of the invention.
Description
본 발명은 방향족 화합물 및 이를 이용한 유기전계발광소자에 관한 것으로서, 보다 상세하게는, 휘도 및 색순도가 우수한 피렌계 청색발광화합물 및 이를 이용한 유기전계발광소자에 관한 것이다.The present invention relates to an aromatic compound and an organic light emitting device using the same, and more particularly, to a pyrene-based blue light emitting compound having excellent brightness and color purity, and an organic light emitting device using the same.
최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자 (organic light emitting diode:OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color) 디스플레이 또는 조명으로의 응용이 기대되고 있다. 이를 위하여 고휘도, 고효율 및 고색순도의 청색발광물질에 대한 필요성이 증가하고 있다.Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT, but has a limited viewing angle. It has disadvantages such as the need for back light. In contrast, the organic light emitting diode (OLED), which is a new flat panel display device, is a display using a self-luminous phenomenon, and has a large viewing angle, can be thinner and shorter than a liquid crystal display, and has a fast response speed. In recent years, the application to full-color display or lighting is expected. To this end, the need for a blue light emitting material of high brightness, high efficiency and high color purity is increasing.
청색발광물질로서 미국 등록특허 제US 7053255 에는 중심부는 디페닐안트라센 구조 를 가지며, 아릴기가 말단에 치환된 청색 발광 화합물 및 이를 이용한 유기전계발광소자가 개시되어 있지만 발광효율 및 휘도가 충분하지 않다는 문제점이 있었다.As a blue light emitting material, US Patent No. 7053255 discloses a blue light emitting compound having a diphenyl anthracene structure and an aryl group substituted at its center, and an organic light emitting device using the same, but the light emitting efficiency and luminance are not sufficient. there was.
한편, 미국등록특허공보 제US 7233019호, 대한민국공개특허공보 제2006-0006760호에는 치환된 피렌계 화합물을 이용한 유기전계발광소자가 개시되어 있으나, 청색의 색순도가 낮아서 진한 청색(deep blue)의 구현이 어렵기 때문에 천연색의 풀컬러 디스플레이를 구현하는데 문제점이 있다.On the other hand, US Patent Publication No. US 7233019, Korean Patent Publication No. 2006-0006760 discloses an organic light emitting device using a substituted pyrene-based compound, but the implementation of deep blue due to the low color purity of blue Because of this difficulty, there is a problem in implementing a full-color display of natural colors.
본 발명이 이루고자 하는 기술적 과제는 청색의 휘도 및 색순도가 우수한 방향족 화합물을 제공하는 것이다.The technical problem to be achieved by the present invention is to provide an aromatic compound having excellent blue luminance and color purity.
본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 방향족 화합물을 이용한 유기전계발광소자를 제공하는 것이다.The second technical problem to be achieved by the present invention is to provide an organic light emitting device using the aromatic compound.
상기 첫 번째 기술적 과제를 달성하기 위해서, 본 발명은 하기 화학식 (1)로 표시되는 방향족 화합물을 제공한다.In order to achieve the first technical problem, the present invention provides an aromatic compound represented by the following formula (1).
(1)(One)
(상기 식에서, (Wherein,
L은 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로 아릴기이며, L is each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
A1 내지 A4는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 20의 헤테로 아릴기이다)A 1 to A 4 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted hetero aryl group having 3 to 20 carbon atoms )
본 발명의 일실시예에 의하면, 상기 L은 치환 또는 비치환된 페닐기인 것이 바람직하다.According to one embodiment of the present invention, L is preferably a substituted or unsubstituted phenyl group.
본 발명의 다른 일실시예에 의하면, 상기 식에서, 상기 A1 내지 A4 및 치환기는 인접한 작용기와 고리를 형성하여 포화 또는 불포화 고리를 형성할 수 있다. According to another embodiment of the present invention, wherein A 1 to A 4 and the substituent may form a ring with an adjacent functional group to form a saturated or unsaturated ring.
본 발명의 다른 일실시예에 의하면, 상기 L, A1 내지 A4의 치환기는 치환 또는 비치환된 탄소수 1 내지 24의 알킬기, 치환 또는 비치환된 탄소수 3 내지 24의 시클로알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 알콕시기, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 6 내지 24의 아릴기, 치환 또는 비치환된 탄소수 6 내지 24의 아릴옥시기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴아미노기, 치환 또는 비치환된 탄소수 2 내지 40의 알킬아미노기, 게르마늄기, 보론기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬실릴기, 치환 또는 비치환의 탄소수 6-40의 아릴실릴기 및 중수소로 이루어진 군에서 선택된 어느 하나인 것이 바람직하며, 이때 시아노기, 할로겐기 또는 중수소 중에서 선택되는 것이 더욱 바람직하다. According to another embodiment of the present invention, the substituents of L, A 1 to A 4 are substituted or unsubstituted C1-C24 alkyl groups, substituted or unsubstituted C3-C24 cycloalkyl groups, substituted or unsubstituted Substituted alkoxy group, cyano group, halogen group, substituted or unsubstituted aryl group having 6 to 24 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, substituted or unsubstituted carbon atoms 2 to 24 A heteroaryl group having 24, a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 40 carbon atoms, a germanium group, a boron group, a substituted or unsubstituted alkylsilyl having 1 to 24 carbon atoms Group, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms and deuterium, preferably any one selected from cyano group, halogen group or deuterium. Very good.
또한 본 발명의 일실시에 따른 화합물은 유기전계발광소자에 사용될 뿐만 아니라, 유기박막트랜지스터(OTFT), RFID(Radio-Frequency Identification) 등에도 사용될 수 있다.In addition, the compound according to an embodiment of the present invention can be used not only in organic light emitting diodes, but also in organic thin film transistors (OTFTs) and radio-frequency identification (RFID).
또한 본 발명은 상기 두 번째 기술적 과제를 해결하기 위하여, 애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 상기 화학식 (1)에 따른 방향족 화합물이 함유된 층을 포함하는 유기전계발광소자를 제공한다.The present invention also provides an anode, in order to solve the second technical problem; Cathode; And it provides an organic electroluminescent device comprising a layer containing an aromatic compound according to the formula (1) between the anode and the cathode.
본 발명의 일실시예에 의하면, 본 발명에 따른 방향족 화합물은 상기 애노드 및 캐소드 사이의 발광층에 포함되는 것이 바람직하다. According to one embodiment of the invention, the aromatic compound according to the invention is preferably included in the light emitting layer between the anode and the cathode.
또한 본 발명의 다른 일실시예에 의하면, 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 정공저지층, 전자수송층, 전자주입층 및 전자저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있으며, 상기 정공주입층, 정공수송층, 정공저지층, 발광층, 전자수송층, 전자주입층 및 전자저지층 중 적어도 한층 이상은 용액공정에 의하여 형성되는 것이 바람직하다. In addition, according to another embodiment of the present invention, the anode and the cathode between the hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer further comprises one or more layers selected from the group At least one or more of the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron transport layer, the electron injection layer, and the electron blocking layer may be formed by a solution process.
또한 본 발명의 또 다른 일실시예에 의하면, 상기 발광층은 하기 실시예에 기재된 화학식 BH1 내지 BH39의 화합물 중 어느 하나 이상의 화합물을 더 포함할 수 있다. In addition, according to another embodiment of the present invention, the light emitting layer may further include any one or more compounds of the compounds of formula BH1 to BH39 described in the following examples.
또한 본 발명의 또 다른 일실시예에 의하면, 상기 발광층은 상기 화학식 (1)로 표시되는 화합물을 1종 이상 더 포함하거나 또는 1931 CIE(x,y)의 x와 y의 합이 0.3이상인 1종 이상의 화합물을 더 포함할 수 있다. In addition, according to another embodiment of the present invention, the light emitting layer may further include at least one compound represented by Formula (1), or at least one sum of x and y of 1931 CIE (x, y) of 0.3 or more. It may further comprise a compound.
또한 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 유용하게 사용될 수 있다. In addition, the organic light emitting display device according to the present invention may be usefully used for display devices, display devices, and monochrome or white lighting devices.
본 발명에 따른 화학식 (1)의 화합물을 애노드와 캐소드 사이의 박막층에 포함하는 유기전계발광소자는 청색의 휘도, 색순도, 수명특성이 우수하기 때문에 디스플레이 및 조명 등에 유용하게 사용될 수 있다.The organic light emitting device including the compound of formula (1) according to the present invention in the thin film layer between the anode and the cathode may be usefully used for display and lighting because of its excellent brightness, color purity, and lifespan.
본 발명에 따른 방향족 화합물은 하기 화학식 (1)로 표시되는 것이 특징이다.The aromatic compound according to the present invention is characterized by being represented by the following general formula (1).
(1)(One)
(상기 식에서, (Wherein,
L은 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로 아릴기이며, L is each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
A1 내지 A4는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 20의 헤테로 아릴기이다)A 1 to A 4 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted hetero aryl group having 3 to 20 carbon atoms )
본 발명의 일구현예에 의하면, 상기 L은 치환 또는 비치환된 페닐기인 것이 바람직하다.According to one embodiment of the present invention, L is preferably a substituted or unsubstituted phenyl group.
본 발명의 다른 일구현예에 의하면, 상기 식에서, 상기 A1 내지 A4 및 치환기는 인접한 작용기와 고리를 형성하여 포화 또는 불포화 고리를 형성할 수 있다. According to another embodiment of the present invention, wherein A 1 to A 4 and the substituent may form a ring with an adjacent functional group to form a saturated or unsaturated ring.
본 발명의 다른 일구현예에 의하면, 상기 L, A1 내지 A4의 치환기는 치환 또는 비치환된 탄소수 1 내지 24의 알킬기, 치환 또는 비치환된 탄소수 3 내지 24의 시클로알킬기, 치환 또는 비치환된 탄소수 1 내지 24의 알콕시기, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 6 내지 24의 아릴기, 치환 또는 비치환된 탄소수 6 내지 24의 아릴옥시기, 치환 또는 비치환된 탄소수 2 내지 24의 헤테로아릴기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴아미노기, 치환 또는 비치환된 탄소수 2 내지 40의 알킬아미노기, 게르마늄기, 보론기, 치환 또는 비치환된 탄소수 1 내지 24의 알킬실릴기, 치환 또는 비치환의 탄소수 6-40의 아릴실릴기 및 중수소로 이루어진 군에서 선택된 어느 하나인 것이 바람직하며, 이때 시아노기, 할로겐기 또는 중수소 중에서 선택되는 것이 더욱 바람직하다. According to another embodiment of the present invention, the substituents of L, A 1 to A 4 are substituted or unsubstituted C1-C24 alkyl group, substituted or unsubstituted C3-C24 cycloalkyl group, substituted or unsubstituted Substituted alkoxy group, cyano group, halogen group, substituted or unsubstituted aryl group having 6 to 24 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, substituted or unsubstituted carbon atoms 2 to 24 A heteroaryl group having 24, a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 40 carbon atoms, a germanium group, a boron group, a substituted or unsubstituted alkylsilyl having 1 to 24 carbon atoms Group, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms and deuterium, preferably any one selected from cyano group, halogen group or deuterium. Very good.
본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 펜틸기, iso-아밀기, 헥실기, 헵틸기, 옥틸기, 스테아릴기, 트리클로로메틸기, 트리플루오르메틸기 등을 들 수 있으며, 상기 알킬기 중 하나 이상의 수소 원자는 중수소원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 트리플루오로메틸기, 실릴기 (이 경우 "알킬실릴기"라 함), 치환 또는 비치환된 아미노기 (-NH2, -NH(R), -N(R')(R''), R'과 R"은 서로 독립적으로 탄소수 1 내지 20의 알킬기이며, 이 경우 "알킬아미노기"라 함), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 20의 알킬기, 탄소수 1 내지 20의 할로겐화된 알킬기, 탄소수 1 내지 20의 알케닐기, 탄소수 1 내지 20의 알키닐기, 탄소수 1 내지 20의 헤테로알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 6 내지 60의 아릴알킬기, 탄소수 4 내지 40의 헤테로아릴기 또는 탄소수 4 내지 40의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the 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, a silyl group (in this case, Alkylsilyl group "), substituted or unsubstituted amino group (-NH2, -NH (R), -N (R ') (R"), R' and R "are independently of each other having 1 to 20 carbon atoms Alkyl group, in this case " alkylamino group "), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C20 alkyl group, C1-C20 halogenated alkyl group, C1-C20 Alkenyl group, C1-C20 alkynyl group, C1-C20 Heterocyclic group, which may be substituted with a heteroaryl group containing 6 to 30 carbon atoms of the aryl group, having 6 to 60 carbon atoms in the arylalkyl group, having 4 to 40 carbon atoms or a heteroaryl group of from 4 to 40.
본 발명의 화합물에서 사용되는 치환기인 시클로알킬기의 구체적인 예로는, 시클로 프로필기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기, 아다만틸기 등을 들 수 있으며 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the cycloalkyl group which is a substituent used in the compound of the present invention include a cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, and the like. It can be substituted with a substituent of.
본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. These can be mentioned and can substitute by the same substituent as the case of the said alkyl group.
본 발명의 화합물에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br)등을 들 수 있다.Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.
본 발명의 화합물에서 사용되는 치환기인 아릴기의 구체적인 예로는 페닐기, 2-메틸페닐기, 3-메틸페닐기, 4-메틸페닐기, 4-에틸페닐기, o-비페닐기, m-비페닐기, p-비페닐기, 4-메틸비페닐기, 4-에틸비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 1-나프틸기, 2-나프틸기, 1-메틸나프틸기, 2-메틸나프틸기, 안트릴기, 페난트릴기, 피레닐기, 플루오레닐기, 테트라히드로나프틸기 등과 같은 방향족 그룹을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다. Specific examples of the 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 And 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 group.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기의 구체적인 예로는 피리디닐기, 피리미디닐기, 트리아지닐기, 인돌리닐기, 퀴놀린닐기, 피롤리디닐기, 피페 리디닐기, 모폴리디닐기, 피페라디닐기, 카바졸릴기, 옥사졸릴기, 옥사디아졸릴기, 벤조옥사졸릴기, 치아졸릴기, 치아디아졸릴기, 벤조치아졸릴기, 트리아졸릴기, 이미다졸릴기 또는 벤조이미다졸기 등이 있으며, 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.Specific examples of the heteroaryl group which is a substituent used in the compound of the present invention include pyridinyl group, pyrimidinyl group, triazinyl group, indolinyl group, quinolinyl group, pyrrolidinyl group, piperidinyl group, morpholidinyl group, pipepe Radiinyl, carbazolyl, oxazolyl, oxdiazolyl, benzooxazolyl, chiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, imidazolyl or benzoimidazole At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.
본 발명의 일구현예에 따른 방향족 화합물은 예를 들어, 하기 화학식 (BD2) 내지 (BD73)로 표시되는 군으로부터 선택된 어느 하나의 화합물일 수 있으나, 이들 예시 화합물에 한정되는 것은 아니다.The aromatic compound according to one embodiment of the present invention may be, for example, any one compound selected from the group represented by the following formulas (BD2) to (BD73), but is not limited to these exemplary compounds.
(BD2) (BD3) (BD4)(BD2) (BD3) (BD4)
(BD5) (BD6) (BD7)(BD5) (BD6) (BD7)
(BD8) (BD9) (BD10)(BD8) (BD9) (BD10)
(BD11) (BD12) (BD13)(BD11) (BD12) (BD13)
(BD14) (BD15) (BD16)(BD14) (BD15) (BD16)
(BD17) (BD18) (BD19)(BD17) (BD18) (BD19)
(BD 20) (BD 21) (BD 22)(BD 20) (BD 21) (BD 22)
(BD 23) (BD 24) (BD 25)(BD 23) (BD 24) (BD 25)
(BD 26) (BD 27) (BD 28)(BD 26) (BD 27) (BD 28)
(BD 29) (BD 30) (BD 31)(BD 29) (BD 30) (BD 31)
(BD 32) (BD 33) (BD 34)(BD 32) (BD 33) (BD 34)
(BD 35) (BD 36) (BD 37)(BD 35) (BD 36) (BD 37)
(BD 38) (BD 39) (BD 40)(BD 38) (BD 39) (BD 40)
(BD 41) (BD 42) (BD 43)(BD 41) (BD 42) (BD 43)
(BD 44) (BD 45) (BD 46)(BD 44) (BD 45) (BD 46)
(BD 47) (BD 48) (BD 49)(BD 47) (BD 48) (BD 49)
(BD 50) (BD 51) (BD 52)(BD 50) (BD 51) (BD 52)
(BD 53) (BD 54) (BD 55)(BD 53) (BD 54) (BD 55)
(BD 56) (BD 57) (BD 58)(BD 56) (BD 57) (BD 58)
(BD 59) (BD 60) (BD 61)(BD 59) (BD 60) (BD 61)
(BD 62) (BD 63) (BD 64) (BD 62) (BD 63) (BD 64)
(BD 65) (BD 66) (BD 67) (BD 65) (BD 66) (BD 67)
(BD 68) (BD 69) (BD 70)(BD 68) (BD 69) (BD 70)
(BD 71) (BD 72) (BD 73)(BD 71) (BD 72) (BD 73)
한편 본 발명에 따른 유기전계발광소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 상기 화학식 (1)에 따른 방향족 화합물이 함유된 층을 포함하는 것이 특징이다. 이때, 본 발명의 일구현예에 따른 피렌계 화합물은 상기 애노드 및 캐소드 사이의 발광층에 포함되는 것이 바람직하며, 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 정공저지층, 발광층, 전자수송층, 전자주입층 및 전자저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.The organic electroluminescent device according to the present invention includes an anode; Cathode; And a layer containing an aromatic compound according to the formula (1) between the anode and the cathode. In this case, the pyrene-based compound according to an embodiment of the present invention is preferably included in the light emitting layer between the anode and the cathode, a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, between the anode and the cathode It may further include one or more layers selected from the group consisting of an electron injection layer and an electron blocking layer.
또한 본 발명의 다른 일실시예에 의하면, 상기 정공주입층, 정공수송층, 정공저지층, 발광층, 전자수송층, 전자주입층 및 전자저지층 중 적어도 한층 이상이 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자를 제공한다.According to another embodiment of the present invention, at least one or more of the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron transport layer, the electron injection layer and the electron blocking layer is formed by a solution process, characterized in that An organic electroluminescent device is provided.
또한 본 발명의 또 다른 실시예에 의하면, 상기 발광층은 하기 화학식 BH01 내지 BH39의 화합물 중 어느 하나 이상의 화합물을 더 포함할 수 있으며, 이에 따라 성능이 향상될 수 있다.In addition, according to another embodiment of the present invention, the light emitting layer may further include any one or more compounds of the compounds of Formulas BH01 to BH39, thereby improving performance.
BH01 BH02 BH03 BH04BH01 BH02 BH03 BH04
BH05 BH06 BH07 BH08BH05 BH06 BH07 BH08
BH09 BH10 BH11 BH12BH09 BH10 BH11 BH12
BH13 BH14 BH15 BH16BH13 BH14 BH15 BH16
BH17 BH18 BH19 BH20BH17 BH18 BH19 BH20
BH21 BH22 BH23 BH24BH21 BH22 BH23 BH24
BH25 BH26 BH27 BH28BH25 BH26 BH27 BH28
BH29 BH30 BH31 BH32BH29 BH30 BH31 BH32
BH33 BH34 BH35 BH36BH33 BH34 BH35 BH36
BH37 BH38 BH39BH37 BH38 BH39
또한 본 발명이 또 다른 일실시예에 의하면, 상기 발광층은 상기 화학식 (1)로 표시되는 화합물을 1종 이상 더 포함하거나 또는 1931 CIE(x, y)의 x와 y의 합이 0.3 이상인 1종 이상의 화합물을 추가로 포함할 수 있다. According to another embodiment of the present invention, the light emitting layer may further include at least one compound represented by Chemical Formula (1) or at least one sum of x and y of 1931 CIE (x, y) of 0.3 or more. The above compound may be further included.
또한 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용하는 것이 바람직하다.In addition, the organic light emitting display device according to the present invention is preferably used for a display device, a display device, and a monochrome or white illumination device.
구체적인 예로서, 정공수송층(HTL: Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL: Electron Transport Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다. As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.
본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐 -[1,1-비페닐]-4,4'- 디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(a-NPD) 등을 사용할 수 있다.The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl-[1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (a-NPD) and the like can be used.
상기 정공수송층의 하부에는 정공주입층(HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 하기 화학식으로 열거되어 있는 CuPc 또는 스타버스트(Starburst)형 아민류인 TCTA, m-MTDATA 등을 사용할 수 있다.A hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines such as TCTA, m-MTDATA, etc., which are listed in the following formulae, can be used.
또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 상기 전자수송층 재료로는 당업계에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어, 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq3 등을 사용할 수 있다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material for the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq 3 can be used.
한편 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당업계에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.On the other hand, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li 2 O, and BaO can be used.
또한 본 발명의 일실시예에 의하면, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용하는 것이 바람직하다. 또한 본 발명에 따른 화합물은 유기전계발광소자에 사용될 뿐만 아니라, 유기박막트랜지스터(OTFT), RFID(Radio-Frequency Identification) 등에 사용될 수 있다.In addition, according to an embodiment of the present invention, the organic light emitting display device according to the present invention is preferably used for a display device, a display device and a single color or white illumination device. In addition, the compound according to the present invention can be used not only for organic light emitting devices, but also for organic thin film transistors (OTFT), RFID (Radio-Frequency Identification), and the like.
도 1은 본 발명의 유기전계발광 소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기발광 다이오드는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting diode according to the present invention includes an
도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조 방법에 대하여 살펴보면, 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다. Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, the
상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다. 이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이때 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI등이 사용될 수 있다. The
이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다. After the
이하, 본 발명을 하기 실시예를 통하여 본 발명을 보다 상세하게 설명하고자 하나, 하기의 실시예는 단지 설명의 목적을 위한 것으로 본 발명을 제한하기 위한 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.
합성예 1: 화합물 BD3의 합성Synthesis Example 1 Synthesis of Compound BD3
합성예 1-(1) : 4-브로모벤젠-1-보론산의 합성Synthesis Example 1- (1): Synthesis of 4-bromobenzene-1-boronic acid
500 mL 둥근 바닥 플라스크에 1,4-디브로모벤젠 50.0 g(212 mmol)을 가한다. 무수 THF를 250 mL 가한 뒤 질소분위기 하에서 영하 78도까지 냉각한다. 위 용액에 n-BuLi 1.6M 용액 140 mL(223 mmol)을 적가한다. 위 용액을 상기 온도에서 약 1시간 교반한 뒤 트리메틸보레이트(B(OMe)3) 28 mL(223 mmol)을 적가한다. 반응용액의 온도를 상온으로 올린 뒤 2N 염산용액으로 산성이 될 때까지 조금씩 가한다. THF를 감압하여 제거하고, 생긴 고체를 여과한 뒤 과량의 물로 씻어, 32g(수율 75%)의 백색의 고체를 얻었다. To a 500 mL round bottom flask is added 50.0 g (212 mmol) of 1,4-dibromobenzene. 250 mL of dry THF is added and cooled to minus 78 degrees under nitrogen atmosphere. Add 140 mL (223 mmol) of n-BuLi 1.6M solution to the above solution. After stirring the above solution at this temperature for about 1 hour, 28 mL (223 mmol) of trimethylborate (B (OMe) 3 ) was added dropwise. Raise the temperature of the reaction solution to room temperature and add little by little until it becomes acidic with 2N hydrochloric acid solution. THF was removed under reduced pressure, and the resulting solid was filtered and washed with excess water to give 32 g (yield 75%) of white solid.
합성예 1-(2) : 1-(4-브로모페닐)-6-브로모피렌의 합성Synthesis Example 1- (2): Synthesis of 1- (4-bromophenyl) -6-bromopyrene
500 mL 둥근 바닥 플라스크에 1,6-디브로모피렌 20.0 g(55 mmol), 4-브로모벤젠-1-보론산 11.7g (58 mmol), 테트라키스트리페닐포스핀팔라듐 (Pd(PPh3)4) 3.21 g(3 mmol), 탄산칼륨 15.3 g(111 mmol)과 THF 100 mL, 디옥산(dioxane) 100 mL, 물 50 mL을 간한 뒤 12시간 환류시킨다. 반응이 종료되면 상온으로 냉각 한 뒤 생긴 고체를 여과한다. 여과된 고체를 과량의 물과 메탄올로 씻어준다. 헥산과 에틸아세테이트(1:3)을 전개용매로 사용하여 칼럼크로마토그래피로 분리하여 건조한 결과, 8.7 g(수율 35%)의 흰색 고체를 얻었다.In a 500 mL round bottom flask, 20.0 g (55 mmol) of 1,6-dibromopyrene, 11.7 g (58 mmol) of 4-bromobenzene-1-boronic acid, tetrakistriphenylphosphinepalladium (Pd (PPh 3 4 ) 3.21 g (3 mmol), 15.3 g (111 mmol) of potassium carbonate, 100 mL of THF, 100 mL of dioxane and 50 mL of water were refluxed for 12 hours. After the reaction is completed, the resulting solid is filtered after cooling to room temperature. The filtered solid is washed with excess water and methanol. Hexane and ethyl acetate (1: 3) were used as a developing solvent, and the residue was separated by column chromatography and dried to yield 8.7 g (yield 35%) of white solid.
합성예 1-(3) : BD3의 합성Synthesis Example 1- (3): Synthesis of BD3
250 mL 둥근바닥 플라스크에 1-(4-브로모페닐)-6-브로모피렌 4.0 g(9 mmol), 디페닐아민 3.9 g(23 mmol),BINAP 0.11g(0.17 mmol), NaOtBu 2.2 g(20 mmol), 팔라듐아세테이트 (Pd(OAc)2) 0.1 g(0.44 mmol), 톨루엔 100ml 를 투입하고 24시간 동안 환 류시켰다. 반응이 종결되면, 유기용매를 감압증류하고, 에틸아세테이트와 물로 추출한다. 유기층을 분리하여 용매를 제거 한 뒤, 생긴 고체를 메탄올로 씻어준다. 헥산과 에틸아세테이트(1:3)을 전개용매로 사용하여 칼럼크로마토그래피로 분리하여 건조한 결과, 3.5 g(수율 62.3 %)의 흰색 고체를 얻었다. In a 250 mL round bottom flask, 4.0 g (9 mmol) of 1- (4-bromophenyl) -6-bromopyrene, 3.9 g (23 mmol) of diphenylamine, 0.11 g (0.17 mmol) of BINAP, NaO t Bu 2.2 g (20 mmol), palladium acetate (Pd (OAc) 2 ) 0.1 g (0.44 mmol) and 100 ml of toluene were added and refluxed for 24 hours. After the reaction is completed, the organic solvent is distilled under reduced pressure and extracted with ethyl acetate and water. The organic layer is separated, the solvent is removed, and the resulting solid is washed with methanol. Hexane and ethyl acetate (1: 3) were used as a developing solvent, and the residue was separated by column chromatography and dried to yield 3.5 g (yield 62.3%) of white solid.
MS(MALDI-TOF): m/z 1217 [M]+ MS (MALDI-TOF): m / z 1217 [M] +
합성예 2: 화합물 BD8의 합성Synthesis Example 2 Synthesis of Compound BD8
합성예 2-(1) : 디(4-시아노페닐)아민의 합성Synthesis Example 2- (1): Synthesis of Di (4-cyanophenyl) amine
250 mL 둥근바닥 플라스크에 1-브로모-4-시아노벤젠 20.0 g(110 mmol), 4-시아노아닐린 14.3 g(121 mmol),BINAP 1.37g(2.2 mmol), NaOtBu 13.7 g(140 mmol), 팔라듐아세테이트 (Pd(OAc)2) 0.49 g(2.1 mmol), 톨루엔 100ml 를 투입하고 24시간 동안 환류시켰다. 반응이 종결되면, 유기용매를 감압증류하고, 에틸아세테이트와 물로 추출한다. 유기층을 분리하여 용매를 제거 한 뒤, 생긴 고체를 메탄올로 씻어준다. 헥산과 에틸아세테이트(1:3)을 전개용매로 사용하여 칼럼크로마토그래피로 분리하여 건조한 결과, 18.6 g(수율 77 %)의 흰색 고체를 얻었다. 250 mL round bottom flask was charged 1-bromo-4-cyano-benzene 20.0 g (110 mmol), 4- cyano-aniline 14.3 g (121 mmol), BINAP 1.37g (2.2 mmol), NaO t Bu 13.7 g (140 mmol), palladium acetate (Pd (OAc) 2 ) 0.49 g (2.1 mmol), and 100 ml of toluene were added and refluxed for 24 hours. After the reaction is completed, the organic solvent is distilled under reduced pressure and extracted with ethyl acetate and water. The organic layer is separated, the solvent is removed, and the resulting solid is washed with methanol. Hexane and ethyl acetate (1: 3) were used as a developing solvent, and the residue was separated by column chromatography and dried to yield 18.6 g (yield 77%) of white solid.
합성예 2-(2) : BD08의 합성Synthesis Example 2- (2): Synthesis of BD08
합성예 1-(3)에서 디페닐아민 대신 디(4-시아노페닐)아민을 사용한 것을 제외하고는, 동일한 방법으로 합성하여 BD08 4.2g (수율 57.4%)의 흰색 고체를 얻었다.Synthesis was carried out in the same manner, except that di (4-cyanophenyl) amine was used instead of diphenylamine in Synthesis Example 1- (3) to obtain 4.2 g of a BD08 (yield 57.4%) of a white solid.
MS(MALDI-TOF): m/z 712[M]+ MS (MALDI-TOF): m / z 712 [M] +
합성예 3: 화합물 BD10의 합성Synthesis Example 3 Synthesis of Compound BD10
합성예 1-(3)에서 디페닐아민 대신 디(4-트리메틸실릴페닐)아민을 사용한 것을 제외하고는, 동일한 방법으로 합성하여 BD10 2.1g (수율 54.1%)의 흰색 고체를 얻었다.Synthesis was conducted in the same manner as in Synthesis Example 1- (3), except that di (4-trimethylsilylphenyl) amine was used instead of diphenylamine to obtain 2.1 g of BD10 (yield 54.1%) of a white solid.
MS(MALDI-TOF): m/z 900[M]+ MS (MALDI-TOF): m / z 900 [M] +
합성예 4: 화합물 BD19의 합성Synthesis Example 4 Synthesis of Compound BD19
합성예 1-(3)에서 디페닐아민 대신 디(2-나프틸)아민을 사용한 것을 제외하고는, 동일한 방법으로 합성하여 BD19 3.9g (수율 43.6%)의 흰색 고체를 얻었다.Synthesis was conducted in the same manner as in Synthesis Example 1- (3), except that di (2-naphthyl) amine was used instead of diphenylamine to obtain 3.9 g of BD19 (yield 43.6%) of a white solid.
MS(MALDI-TOF): m/z 812[M]+ MS (MALDI-TOF): m / z 812 [M] +
합성예 5: 화합물 BD34의 합성Synthesis Example 5 Synthesis of Compound BD34
합성예 1-(3)에서 디페닐아민 대신 디(9-페난트릴)아민을 사용한 것을 제외하고는, 동일한 방법으로 합성하여 BD34 4.1g (수율 44.7%)의 흰색 고체를 얻었다.Synthesis was carried out in the same manner, except that di (9-phenanthryl) amine was used instead of diphenylamine in Synthesis Example 1- (3) to obtain 4.1 g of a BD34 (yield 44.7%) of a white solid.
MS(MALDI-TOF): m/z 1012[M]+ MS (MALDI-TOF): m / z 1012 [M] +
실시예 1~ 5 : 유기전계발광소자의 제조Examples 1 to 5: fabrication of an organic light emitting device
ITO 글래스의 발광면적이 2mm×2mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1×10-7torr가 되도록 한 후 상기 ITO 위에 CuPc(800 Å), α-NPD(300 Å) 순으로 성막한 후 합성예 1-(3)에서 제 조된 BH1 + BD3 화합물 3%를 혼합하여 성막(250Å)한 다음 Alq3(350 Å), LiF (5 Å), Al (500 Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. 상기 유기전계발광소자의 발광특성은 0.4mA에서 측정하였다. The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 × 10 −7 torr, and then formed on Cu in the order of CuPc (800 kPa) and α-NPD (300 kPa) on the ITO. Was formed by mixing 3% of BH1 + BD3 compound prepared in Next, Alq 3 (350 Å), LiF (5 Å), and Al (500 Å) were sequentially deposited to form an organic electroluminescent device. The light emission characteristics of the organic light emitting diode were measured at 0.4 mA.
상기 실험과정에서, BD3 대신 하기 [표 1]에 기재된 것을 이용한 것 이외에는 동일하게 유기전계발광소자를 제작하였으며, 상기 유기전계발광소자의 발광특성은 0.4mA에서 측정하였다. In the course of the experiment, an organic light emitting device was manufactured in the same manner as in the following Table 1 instead of BD3, and the light emission characteristics of the organic light emitting device were measured at 0.4 mA.
비교예 1 Comparative Example 1
상기 실험예에 사용된 화합물을 BD3 대신 BD74을 사용한 것 이외에는 동일하게 유기전계발광소자를 제작하였으며, 상기 유기전계발광소자의 발광특성은 0.4 mA에서 측정하였다. BD74의 구조는 다음과 같다.Used in the above experimental example An organic light emitting diode was manufactured in the same manner as that of the compound except for using BD74 instead of BD3, and the emission characteristics of the organic light emitting diode were measured at 0.4 mA. The structure of BD74 is as follows.
BD74 BD74
하기 표 1에는 실시예 1～5과 비교예 1에 따라 제조된 유기전계발광소자에 대하여, 전압, 전류, 휘도, 색 좌표 및 수명을 측정하고 그 결과를 나타내었다. Table 1 below shows the results of measuring the voltage, current, luminance, color coordinates, and lifespan of the organic light emitting diodes manufactured according to Examples 1 to 5 and Comparative Example 1.
(BD3)Example 1
(BD3)
(BD8)Example 2
(BD8)
(BD10)Example 3
(BD10)
(BD19)Example 4
(BD19)
(BD34)Example 5
(BD34)
(BD74)Comparative Example 1
(BD74)
상기 표 1의 결과에서 알 수 있는 바와 같이, 본 발명에 따른 유기전계발광소자는 휘도 및 색순도가 종래의 청색발광화합물을 사용한 경우보다 우수한 특성을 나타낸다.As can be seen from the results of Table 1, the organic light emitting display device according to the present invention exhibits superior characteristics than those of conventional blue light emitting compounds.
실시예 6 ~ 8Examples 6-8
하기 표 2에는 BD3을 다양한 호스트에 대하여 소자를 제작하고, 전압, 전류, 휘도, 색 좌표 및 수명을 측정하고 그 결과를 나타내었다.In Table 2, BD3 was fabricated for various hosts, and voltage, current, brightness, color coordinates, and lifetime were measured and the results are shown.
(BH01+BD3)Example 1
(BH01 + BD3)
(BH05+BD3)Example 6
(BH05 + BD3)
(BH08+BD3)Example 7
(BH08 + BD3)
(BH12+BD3)Example 8
(BH12 + BD3)
실시예 9Example 9
실시예 1에서 발광층을 BH1 + 합성예 1에서 제조된 화합물 BD3 3% 및 화합물 YD1 2%를 혼합하여 성막한 것을 제외하고 동일하게 제작하였으며, 상기 유기전계발광소자의 발광특성은 0.4mA에서 측정하였다. 화합물 YD1를 실시예 1의 조건으로 측정하였을 때 측정된 CIE(x,y)는 (0.56, 0.43)이며, 화합물 YD1의 구조는 다음과 같다.A light emitting layer was manufactured in the same manner as in Example 1 except that the film was formed by mixing BH1 + 3% compound BD3 prepared in Synthesis Example 1 and 2% compound YD1, and the emission characteristics of the organic light emitting diode were measured at 0.4 mA. . When the compound YD1 was measured under the conditions of Example 1, the measured CIE (x, y) was (0.56, 0.43), and the structure of the compound YD1 was as follows.
YD1 YD1
상기 실시예 9의 결과를 하기 표 4에 나타내었다.The results of Example 9 are shown in Table 4 below.
(mA/cm2)(mA / cm2)
(BH1+BD3+YD1)Example 9
(BH1 + BD3 + YD1)
실시예 10 ~ 15Examples 10-15
화학식 1에 의한 화합물에 대하여 전하이동도를 측정하여 하기 표 4에 정리하였으며, 전하이동도는 타임 오브 플라이트 메스 스펙트로메터(Time of Flight Mass Spectrometer)를 이용하여 측정하였다.The charge mobility of the compound according to Formula 1 was measured and summarized in Table 4 below, and the charge mobility was measured using a time of flight mass spectrometer.
(화합물)(compound)
(BD3)Example 10
(BD3)
(BD8)Example 11
(BD8)
(BD10)Example 12
(BD10)
(BD19)Example 13
(BD19)
(BD34)Example 14
(BD34)
(BD74)Example 15
(BD74)
(cm2/Vs)Charge mobility
(cm 2 / Vs)
상기 표 1 내지 표 4의 결과에서 알 수 있는 바와 같이, 본 발명에 따른 방향족화합물은 휘도 및 색순도가 종래의 유기발광화합물을 사용한 경우보다 우수하면서도 장수명의 특성을 나타낼 뿐만 아니라, 조명, 유기박막트랜지스터, RFID 등의 전자재료에 유용하게 쓰일 수 있다.As can be seen from the results of Table 1 to Table 4, the aromatic compound according to the present invention is excellent in the brightness and color purity than the case of using a conventional organic light emitting compound, but also exhibits long life characteristics, lighting, organic thin film transistor It can be usefully used for electronic materials such as RFID and RFID.
도 1은 본 발명의 일 실시예에 따른 유기전계발광소자의 개략도이다.1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
<도면의 주요부분에 대한 부호의 설명><Description of the symbols for the main parts of the drawings>
10: 기판 20: 애노드10: substrate 20: anode
30: 정공주입층 40: 정공수송층30: hole injection layer 40: hole transport layer
50: 유기발광층 60: 전자수송층50: organic light emitting layer 60: electron transport layer
70: 전자주입층 80: 캐소드70: electron injection layer 80: cathode
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| KR102126087B1 (en) * | 2011-10-11 | 2020-06-23 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Light-emitting element, light-emitting device, electronic device, lighting device, and pyrene-based compound |
| US9385324B2 (en) | 2012-05-07 | 2016-07-05 | Samsung Electronics Co., Ltd. | Electronic system with augmented reality mechanism and method of operation thereof |
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