WO2020149656A1 - Novel compound and organic light-emitting diode using same - Google Patents
Novel compound and organic light-emitting diode using same Download PDFInfo
- Publication number
- WO2020149656A1 WO2020149656A1 PCT/KR2020/000781 KR2020000781W WO2020149656A1 WO 2020149656 A1 WO2020149656 A1 WO 2020149656A1 KR 2020000781 W KR2020000781 W KR 2020000781W WO 2020149656 A1 WO2020149656 A1 WO 2020149656A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- light emitting
- layer
- formula
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- -1 Biphenylyl Chemical group 0.000 claims description 69
- 239000011368 organic material Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 129
- 238000002347 injection Methods 0.000 description 38
- 239000007924 injection Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 26
- 230000032258 transport Effects 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000010406 cathode material Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 0 CC(N(C)*=O)=O Chemical compound CC(N(C)*=O)=O 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- MHYZYLQHHQNSPV-UHFFFAOYSA-N 4-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1C1=CC=CC=C1N2 MHYZYLQHHQNSPV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 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 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- IJNAHWROJYGEGL-UHFFFAOYSA-N 1-bromodibenzofuran-2-ol Chemical compound C1=CC=C2C3=C(Br)C(O)=CC=C3OC2=C1 IJNAHWROJYGEGL-UHFFFAOYSA-N 0.000 description 3
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- IMLDYQBWZHPGJA-UHFFFAOYSA-N 2-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3NC2=C1 IMLDYQBWZHPGJA-UHFFFAOYSA-N 0.000 description 3
- WOGNRTCMYWOAIA-UHFFFAOYSA-N 3-bromo-2-fluorodibenzofuran Chemical compound BrC=1C(=CC2=C(OC3=C2C=CC=C3)C=1)F WOGNRTCMYWOAIA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- UAWQARATCDVZAH-UHFFFAOYSA-N 3-chloro-4-fluorodibenzofuran Chemical compound ClC=1C=CC2=C(OC3=C2C=CC=C3)C1F UAWQARATCDVZAH-UHFFFAOYSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- QODXILVBZCCCGD-UHFFFAOYSA-N 4-bromodibenzothiophen-3-ol Chemical compound OC1=CC=C2C(SC3=C2C=CC=C3)=C1Br QODXILVBZCCCGD-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- IAWRFMPNMXEJCK-UHFFFAOYSA-N 3-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 IAWRFMPNMXEJCK-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- GXCUJMFCKXOLSH-UHFFFAOYSA-N 4-(9,9-dimethylfluoren-2-yl)-9H-carbazole Chemical compound CC1(C)c2ccccc2-c2ccc(cc12)-c1cccc2[nH]c3ccccc3c12 GXCUJMFCKXOLSH-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BYPCJJONRMPERB-UHFFFAOYSA-N C1(=CC(=CC=C1)C1=NC(=NC(=N1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC(=CC=C1)C1=NC(=NC(=N1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 BYPCJJONRMPERB-UHFFFAOYSA-N 0.000 description 1
- QOUMHNQIGPHNPC-UHFFFAOYSA-N C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=C2C3=CC=CC=C3NC2=C1 Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=C2C3=CC=CC=C3NC2=C1 QOUMHNQIGPHNPC-UHFFFAOYSA-N 0.000 description 1
- QDPFAYZVPYCGHS-UHFFFAOYSA-N CC(C)(c1ccccc1-c1ccc2)c1c2-c1cccc2c1c1ccccc1[n]2-c(cc1[o]c2ccccc2c1c1)c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound CC(C)(c1ccccc1-c1ccc2)c1c2-c1cccc2c1c1ccccc1[n]2-c(cc1[o]c2ccccc2c1c1)c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 QDPFAYZVPYCGHS-UHFFFAOYSA-N 0.000 description 1
- AOCNEMVIIUCJET-UHFFFAOYSA-N CC(N(C)C(c1ccccc1)=O)=O Chemical compound CC(N(C)C(c1ccccc1)=O)=O AOCNEMVIIUCJET-UHFFFAOYSA-N 0.000 description 1
- ZSBDPRIWBYHIAF-UHFFFAOYSA-N CC(NC(C)=O)=O Chemical compound CC(NC(C)=O)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 1
- OGMUQXNMLQVEMA-UHFFFAOYSA-N CC1(C)c2cc(-c(cc3)cc(c4ccccc44)c3[n]4-c(c(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c3)cc4c3c3ccccc3[o]4)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(-c(cc3)cc(c4ccccc44)c3[n]4-c(c(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c3)cc4c3c3ccccc3[o]4)ccc2-c2ccccc12 OGMUQXNMLQVEMA-UHFFFAOYSA-N 0.000 description 1
- DKMBKZHSHKKOJD-UHFFFAOYSA-N CC1(C)c2cc(-c3cccc4c3c(cccc3)c3[n]4-c3ccc4[o]c5ccccc5c4c3-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2-c2c1cccc2 Chemical compound CC1(C)c2cc(-c3cccc4c3c(cccc3)c3[n]4-c3ccc4[o]c5ccccc5c4c3-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2-c2c1cccc2 DKMBKZHSHKKOJD-UHFFFAOYSA-N 0.000 description 1
- LUWKDUNLHIZGLO-UHFFFAOYSA-N CC1(C)c2cccc(-c3cccc(c4c5cccc4)c3[n]5-c(c(-c3nc(-c4ccccc4)nc(-c4ccc(CC5(C)c(ccc(-c(cc6)cc7c6c6ccccc6[n]7-c(c(-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)c6)cc7c6c6ccccc6[o]7)c6)c6-c6ccccc56)cc4)n3)c3)cc4c3c3ccccc3[o]4)c2-c2c1cccc2 Chemical compound CC1(C)c2cccc(-c3cccc(c4c5cccc4)c3[n]5-c(c(-c3nc(-c4ccccc4)nc(-c4ccc(CC5(C)c(ccc(-c(cc6)cc7c6c6ccccc6[n]7-c(c(-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)c6)cc7c6c6ccccc6[o]7)c6)c6-c6ccccc56)cc4)n3)c3)cc4c3c3ccccc3[o]4)c2-c2c1cccc2 LUWKDUNLHIZGLO-UHFFFAOYSA-N 0.000 description 1
- GCCHEFAXUVFOKS-UHFFFAOYSA-N CCC(N(CC)C(C)=O)=O Chemical compound CCC(N(CC)C(C)=O)=O GCCHEFAXUVFOKS-UHFFFAOYSA-N 0.000 description 1
- KCXNKXQSRWZAKG-UHFFFAOYSA-N CN(C=O)C(C1CCCC1)=O Chemical compound CN(C=O)C(C1CCCC1)=O KCXNKXQSRWZAKG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 239000004305 biphenyl Substances 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
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001638 boron Chemical class 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ATDRUPMQBXZJNT-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)c1)cc2c1c1ccccc1[o]2 Chemical compound c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)c1)cc2c1c1ccccc1[o]2 ATDRUPMQBXZJNT-UHFFFAOYSA-N 0.000 description 1
- GNSVQNKZYBBMSZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 GNSVQNKZYBBMSZ-UHFFFAOYSA-N 0.000 description 1
- ZSSLSDSYJWCOTI-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c(c(-c1ccccc1)ccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c(c(-c1ccccc1)ccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 ZSSLSDSYJWCOTI-UHFFFAOYSA-N 0.000 description 1
- SIFWQIMEOUMQAE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 SIFWQIMEOUMQAE-UHFFFAOYSA-N 0.000 description 1
- BQYWUFRAZSITCF-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c1ccccc1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c1ccccc1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 BQYWUFRAZSITCF-UHFFFAOYSA-N 0.000 description 1
- ZUFTVWXKNKJNNW-UHFFFAOYSA-N c(cc1)ccc1-c(cc1c2c3ccc(-c4ccccc4)c2)ccc1[n]3-c(ccc1c2c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1c2c3ccc(-c4ccccc4)c2)ccc1[n]3-c(ccc1c2c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 ZUFTVWXKNKJNNW-UHFFFAOYSA-N 0.000 description 1
- UBCJQUIPFPRDML-UHFFFAOYSA-N c(cc1)ccc1-c(cc1c2c3cccc2)cc(-c2ccccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1c2c3cccc2)cc(-c2ccccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 UBCJQUIPFPRDML-UHFFFAOYSA-N 0.000 description 1
- OKPPICPBGBMNQG-UHFFFAOYSA-N c(cc1)ccc1-c(cccc1c2c3cccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cccc1c2c3cccc2)c1[n]3-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 OKPPICPBGBMNQG-UHFFFAOYSA-N 0.000 description 1
- WXIVHIVDOPDCHA-UHFFFAOYSA-N c(cc1)ccc1-c1cc([n](c2c3cccc2)-c(c2c(cc4)c5ccccc5[o]2)c4-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)c3c(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1cc([n](c2c3cccc2)-c(c2c(cc4)c5ccccc5[o]2)c4-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)c3c(-c2ccccc2)c1 WXIVHIVDOPDCHA-UHFFFAOYSA-N 0.000 description 1
- SJOCTNQZRSABKP-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c(c(-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc3c2c2ccccc2[n]3-c(cc2[o]c3ccccc3c2c2)c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)n1)c1)cc2c1c1ccccc1[o]2 Chemical compound c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c(c(-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc3c2c2ccccc2[n]3-c(cc2[o]c3ccccc3c2c2)c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)n1)c1)cc2c1c1ccccc1[o]2 SJOCTNQZRSABKP-UHFFFAOYSA-N 0.000 description 1
- AAKQZSIBEBDXED-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 AAKQZSIBEBDXED-UHFFFAOYSA-N 0.000 description 1
- WJHHYHQVRAFTAV-UHFFFAOYSA-N c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c(c1c(cc2)c3ccccc3[o]1)c2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 WJHHYHQVRAFTAV-UHFFFAOYSA-N 0.000 description 1
- BMAXCKJSLRRJRL-UHFFFAOYSA-N c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c(cc1[o]c2ccccc2c1c1)c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c(cc1[o]c2ccccc2c1c1)c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 BMAXCKJSLRRJRL-UHFFFAOYSA-N 0.000 description 1
- JNFLIXQUXXYNKN-UHFFFAOYSA-N c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1cccc2c1c(cccc1)c1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 JNFLIXQUXXYNKN-UHFFFAOYSA-N 0.000 description 1
- LZZUYNWEPDFHTD-UHFFFAOYSA-N c(cc1)ccc1-c1ccccc1-c1cccc(c2ccccc22)c1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1ccccc1-c1cccc(c2ccccc22)c1[n]2-c1ccc2[o]c3ccccc3c2c1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 LZZUYNWEPDFHTD-UHFFFAOYSA-N 0.000 description 1
- ULNODSANHPXUHB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(ccc2c3[o]c4ccccc24)c3-[n]2c(ccc(-c3c(cccc4)c4ccc3)c3)c3c3c2cccc3)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c(ccc2c3[o]c4ccccc24)c3-[n]2c(ccc(-c3c(cccc4)c4ccc3)c3)c3c3c2cccc3)nc(-c2ccccc2)n1 ULNODSANHPXUHB-UHFFFAOYSA-N 0.000 description 1
- VNBINNJSHPLXCX-UHFFFAOYSA-N c1ccc(C(c2ccccc2)(c2ccc(c(ccc(-c3ccccc3)c3)c3[n]3-c4ccc5[o]c6ccccc6c5c4-4)c3c2)c2nc(-c3ccccc3)nc-4n2)cc1 Chemical compound c1ccc(C(c2ccccc2)(c2ccc(c(ccc(-c3ccccc3)c3)c3[n]3-c4ccc5[o]c6ccccc6c5c4-4)c3c2)c2nc(-c3ccccc3)nc-4n2)cc1 VNBINNJSHPLXCX-UHFFFAOYSA-N 0.000 description 1
- KNMGCQSZXFYDLQ-UHFFFAOYSA-N c1ccc(C2N=C(c3ccccc3)N=C(c3c(c4ccccc4[o]4)c4ccc3-[n]3c(ccc(-c4ccccc4)c4)c4c4ccccc34)N2)cc1 Chemical compound c1ccc(C2N=C(c3ccccc3)N=C(c3c(c4ccccc4[o]4)c4ccc3-[n]3c(ccc(-c4ccccc4)c4)c4c4ccccc34)N2)cc1 KNMGCQSZXFYDLQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold 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
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 239000005416 organic matter Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010345 tape casting Methods 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
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
- the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
- the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
- the organic material layer is often formed of a multi-layer structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
- Patent Document 0001 Korean Patent Publication No. 10-2013-073537
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the present invention provides a compound represented by Formula 1:
- X is O or S
- Y 1 , Y 2 and Y 3 are each independently CH; Or N, provided that at least two of Y 1 , Y 2 and Y 3 are N,
- Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
- the two * are 1 and 2, respectively; 2 and 3; Or 3 and 4,
- R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
- R 2 is substituted or unsubstituted C 6-60 aryl
- n is an integer from 0 to 6
- n is an integer from 1 to 8.
- the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device comprising the compound of the present invention described above.
- the compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device.
- the compound represented by Chemical Formula 1 may be used as a light emitting layer material.
- FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 It is done.
- substituted or unsubstituted in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents
- the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
- the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
- the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
- the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
- the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.
- the fluorenyl group When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
- the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
- the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazo
- an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the example of the aryl group described above.
- the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group.
- heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
- the alkenyl group among the alkenyl groups is the same as the exemplified alkenyl group.
- the description of the aryl group described above may be applied, except that the arylene is a divalent group.
- the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group.
- the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding.
- the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
- the compound represented by Formula 1 may be any one selected from compounds represented by Formulas 2 to 7 below:
- X, Y 1 , Y 2 , Y 3 , Ar 1 , Ar 2 , R 1 , R 2 , n and m are as defined above.
- Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Dibenzofuranyl or dibenzothiophenyl.
- Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Or dibenzofuranyl.
- R 1 is hydrogen; Or deuterium.
- R 2 is phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Or dimethylfluorenyl.
- n 1 or 2.
- the compound represented by the formula (1) according to the present invention has a structure in which the electron acceptor unit nitrogen-containing heterocycle centered around dibenzofuran or dibenzothiophene and the carbazole group, the electron donor unit, are bonded to the ortho position. Interaction with each other face-to-face generates an intra-charge transfer (ICT) state, resulting in a smaller bandgap and light emission at longer wavelengths, resulting in easy energy transfer to the dopant of the yellow-green light-emitting device.
- ICT intra-charge transfer
- the aryl group substituted with carbazole increases the electron donation ability of carbazole to help the ICT to be generated more effectively, and at the same time compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment, high efficiency, It may have a low driving voltage, high luminance, and long life.
- the compound represented by Chemical Formula 1 may be prepared by a manufacturing method according to Reaction Scheme 1 below.
- the manufacturing method may be more specific in the manufacturing examples to be described later.
- X 1 , X 2 and X 3 are each independently halogen, preferably bromo or chloro, and the description of the remaining substituents is as defined above.
- the first and second reactions are preferably performed in the presence of a palladium catalyst and a base as a Suzuki coupling reaction.
- the third reaction is an amination reaction.
- Reactants and catalysts for the reaction can be modified as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.
- the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
- the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.
- the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer.
- the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.
- the organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport may be represented by Formula 1 It includes the compound displayed.
- the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
- the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.
- the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron injection and electron transport includes the compound represented by Chemical Formula 1.
- the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability.
- an n-type dopant used in the art may be mixed and used.
- the organic material layer includes a light emitting layer and an electron transport layer
- the electron transport layer may include a compound represented by Chemical Formula 1.
- the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
- FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- the compound represented by Chemical Formula 1 may be included in the light emitting layer.
- FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.
- the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
- the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, and preferably, the light emitting layer may further include a compound represented by Chemical Formula 8:
- Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
- R 3 and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
- a and b are each independently an integer from 0 to 7.
- Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
- R 3 and R 4 are hydrogen.
- the compound represented by Formula 8 is any one specifically selected from the group consisting of:
- the organic light emitting device by using a combination of the compound represented by the formula (1) and the compound represented by the formula (8) in the light emitting layer, these synergistic effects can significantly improve the characteristics of low voltage, high efficiency, long life.
- the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. Further, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
- the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
- PVD physical vapor deposition
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon.
- an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
- the compound represented by Chemical Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890).
- the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode
- the second electrode is an anode
- the positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth.
- the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SNO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
- the cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
- a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- the hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer.
- a compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- HOMO highest occupied molecular orbital
- the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
- the light-emitting material is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
- Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
- the light emitting layer may include a host material and a dopant material.
- the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
- condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
- heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
- the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound.
- a compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
- a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
- styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
- metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.
- the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used according to the prior art.
- suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
- the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
- the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
- the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
- ITO Indium Tin Oxide
- distilled water filtered secondarily by a filter of Millipore Co.
- ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
- ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner.
- the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
- HAT-CN hexanitrile hexaazatriphenylene
- ET-A was thermally vacuum-deposited to a thickness of 200 MPa as an electron transport layer, and then ET-B and lithium were vacuum-deposited to a thickness of 100 MPa at a weight ratio of 98:2.
- magnesium and silver were sequentially deposited at a thickness of 220 ⁇ at a ratio of 10:1, and aluminum was deposited at a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting device.
- the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec, and the deposition rate of silver and magnesium was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 2 ⁇ 10 -7 ⁇ 5 ⁇ 10 -6 torr. By maintaining the, an organic light emitting device was produced.
- An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.
- the organic light emitting device manufactured in the above Experimental Example and Comparative Experimental Example was stored in a 110° C. oven for 30 minutes and heat treated, and then applied with a current to measure voltage, efficiency, and lifetime (T95) and the results are shown in Table 1 below. . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 50 mA/cm 2 .
- the compound represented by Chemical Formula 1 has a structure in which a nitrogen-containing hetero ring, which is an electron acceptor unit, and a carbazole group, which is an electron donor unit, are bonded to an ortho position centering on dibenzofuran or dibenzothiophene.
- the electron donor unit and the electron acceptor unit are combined with an ortho, the two substituents face each other and interact with each other to generate an intra-charge transfer (ICT) state.
- ICT intra-charge transfer
- the dopant of the light emitting device is advantageous for energy transfer.
- the aryl group substituted with carbazole increases the electron donating ability of carbazole to make ICT more prominent, and at the same time, compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment. It can be seen through comparison with the example and the comparative example 3.
- substrate 2 anode
Abstract
The present invention provides a novel compound and an organic light-emitting diode using same.
Description
관련 출원(들)과의 상호 인용Cross-citation with relevant application(s)
본 출원은 2019년 1월 18일자 한국 특허 출원 제10-2019-0007096호 및 2020년 1월 15일자 한국 특허 출원 제10-2020-0005489호에 기초한 우선권의 이익을 주장하며, 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다.This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0007096 filed on January 18, 2019 and Korean Patent Application No. 10-2020-0005489 filed on January 15, 2020. All content disclosed in the literature is incorporated as part of this specification.
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layer structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.
선행기술문헌Prior art literature
특허문헌Patent literature
(특허문헌 0001) 한국특허 공개번호 제10-2013-073537호(Patent Document 0001) Korean Patent Publication No. 10-2013-073537
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
X는 O 또는 S이고,X is O or S,
Y
1, Y
2 및 Y
3는 각각 독립적으로, CH; 또는 N이고, 단, Y
1, Y
2 및 Y
3 중 2개 이상이 N이고,Y 1 , Y 2 and Y 3 are each independently CH; Or N, provided that at least two of Y 1 , Y 2 and Y 3 are N,
Ar
1 및 Ar
2는 각각 독립적으로, 치환 또는 비치환된 C
6-60 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 하나 이상의 헤테로 원자를 포함하는 치환 또는 비치환된 C
5-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,
상기 두 개의 *는 각각 1 및 2; 2 및 3; 또는 3 및 4와 연결되고,The two * are 1 and 2, respectively; 2 and 3; Or 3 and 4,
R
1은 수소; 중수소; 치환 또는 비치환된 C
1-60 알킬; 또는 치환 또는 비치환된 C
6-60 아릴이고,R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
R
2는 치환 또는 비치환된 C
6-60 아릴이고,R 2 is substituted or unsubstituted C 6-60 aryl,
m은 0 내지 6의 정수이고,m is an integer from 0 to 6,
n은 1 내지 8의 정수이다.n is an integer from 1 to 8.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 전술한 본 발명의 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device comprising the compound of the present invention described above.
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 발광층 재료로 사용될 수 있다.The compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device. In particular, the compound represented by Chemical Formula 1 may be used as a light emitting layer material.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 It is done.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail in order to help the understanding of the present invention.
본 명세서에서,
는 다른 치환기에 연결되는 결합을 의미한다. In this specification, Means a linkage to another substituent.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우,
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl Groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups, and dibenzofuranyl groups, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group among the alkenyl groups is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
바람직하게는, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 7로 표시되는 화합물 중에서 선택되는 어느 하나일 수 있다:Preferably, the compound represented by Formula 1 may be any one selected from compounds represented by Formulas 2 to 7 below:
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 2 내지 7에서,In the above formula 2 to 7,
X, Y
1, Y
2, Y
3, Ar
1,
Ar
2,
R
1,
R
2, n 및 m은 앞서 정의한 바와 같다.X, Y 1 , Y 2 , Y 3 , Ar 1 , Ar 2 , R 1 , R 2 , n and m are as defined above.
바람직하게는, Ar
1 및
Ar
2은 각각 독립적으로, 페닐; 비페닐릴; 터페닐릴; 나프틸; 안트라세닐; 페난쓰레닐; 트리페닐레닐; 디메틸플루오레닐; 디벤조퓨라닐 또는 디벤조티오페닐이다.Preferably, Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Dibenzofuranyl or dibenzothiophenyl.
더욱 바람직하게는, Ar
1 및
Ar
2은 각각 독립적으로, 페닐; 비페닐릴; 또는 디벤조퓨라닐이다.More preferably, Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Or dibenzofuranyl.
바람직하게는, R
1은 수소; 또는 중수소이다.Preferably, R 1 is hydrogen; Or deuterium.
바람직하게는 R
2는 페닐; 비페닐릴; 터페닐릴; 나프틸; 안트라세닐; 페난쓰레닐; 트리페닐레닐; 또는 디메틸플루오레닐이다.Preferably R 2 is phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Or dimethylfluorenyl.
바람직하게는, n은 1 또는 2이다.Preferably, n is 1 or 2.
바람직하게는, 상기 화학식 1로 표시되는 화합물의 구체예로는, 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, as a specific example of the compound represented by Formula 1, it is any one selected from the group consisting of:
본 발명에 따른 화학식 1로 표시되는 화합물은 디벤조퓨란 혹은 디벤조티오펜을 중심으로 전자 받개 유닛인 함질소헤테로고리와 전자 주개 유닛인 카바졸기가 오쏘 위치로 결합하고 있는 구조를 가져 두 치환기가 마주보며 상호작용하여 intra-charge transfer(ICT) 상태를 발생시켜 밴드갭이 작아지고 보다 긴 파장에서 발광을 하여 황녹색 발광소자의 도펀트로 에너지 전달이 쉽게 발생한다. 또한 카바졸에 치환된 아릴기가 카바졸의 전자 주개 능력을 높여주어 ICT가 더 잘 생기도록 도와주고 동시에 오쏘 위치로 인해 나타날 수 있는 유리전이온도 저하를 상쇄하여 열처리 후에도 소자의 높은 안정성을 나타내 고효율, 저 구동 전압, 고휘도 및 장수명 등을 가질 수 있다. The compound represented by the formula (1) according to the present invention has a structure in which the electron acceptor unit nitrogen-containing heterocycle centered around dibenzofuran or dibenzothiophene and the carbazole group, the electron donor unit, are bonded to the ortho position. Interaction with each other face-to-face generates an intra-charge transfer (ICT) state, resulting in a smaller bandgap and light emission at longer wavelengths, resulting in easy energy transfer to the dopant of the yellow-green light-emitting device. In addition, the aryl group substituted with carbazole increases the electron donation ability of carbazole to help the ICT to be generated more effectively, and at the same time compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment, high efficiency, It may have a low driving voltage, high luminance, and long life.
상기 화학식 1로 표시되는 화합물은 하기 반응식 1에 따른 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The compound represented by Chemical Formula 1 may be prepared by a manufacturing method according to Reaction Scheme 1 below. The manufacturing method may be more specific in the manufacturing examples to be described later.
[반응식 1][Scheme 1]
상기 반응식 1에서, X
1, X
2 및 X
3는 각각 독립적으로 할로겐이고, 바람직하게는, 브로모 또는 클로로이고, 나머지 치환기에 대한 설명은 앞서 정의한 바와 같다.In Reaction Scheme 1, X 1 , X 2 and X 3 are each independently halogen, preferably bromo or chloro, and the description of the remaining substituents is as defined above.
상기 반응식 1에서 첫 번째 및 두 번째 반응은 Suzuki coupling 반응으로 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하다. 상기 반응식 1에서, 세 번째 반응은 아미네이션 반응이다. 상기 반응을 위한 반응물 및 촉매 등은 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. In Reaction Scheme 1, the first and second reactions are preferably performed in the presence of a palladium catalyst and a base as a Suzuki coupling reaction. In Reaction Scheme 1, the third reaction is an amination reaction. Reactants and catalysts for the reaction can be modified as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.
또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport may be represented by Formula 1 It includes the compound displayed.
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. In addition, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
또한, 상기 유기물 층은 전자수송층, 또는 전자주입층을 포함할 수 있고, 상기 전자수송층, 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함한다. Further, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.
또한, 상기 전자수송층, 전자주입층, 또는 전자 주입 및 전자 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 특히, 본 발명에 따른 화학식 1로 표시되는 화합물은 열적 안정성이 우수하고, 6.0 eV 이상의 깊은 HOMO 준위, 높은 삼중함 에너지(ET), 및 정공 안정성을 가지고 있다. 또한, 상기 화학식 1로 표시되는 화합물을 전자 주입 및 전자 수송을 동시에 할 수 있는 유기물 층에 사용할 경우, 당업계에서 사용하는 n-형 도펀트를 혼합하여 사용할 수 있다. In addition, the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron injection and electron transport includes the compound represented by Chemical Formula 1. In particular, the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability. In addition, when the compound represented by Chemical Formula 1 is used in an organic material layer capable of electron injection and electron transport at the same time, an n-type dopant used in the art may be mixed and used.
또한, 상기 유기물 층은 발광층 및 전자수송층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
본 발명에 따른 유기 발광 소자는, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층이 발광층일 수 있으며, 바람직하게는, 상기 발광층은 하기 화학식 8로 표시되는 화합물을 더 포함할 수 있다:In the organic light emitting device according to the present invention, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, and preferably, the light emitting layer may further include a compound represented by Chemical Formula 8:
[화학식 8][Formula 8]
상기 화학식 8에서,In Chemical Formula 8,
Ar
3 및 Ar
4는 각각 독립적으로, 치환 또는 비치환된 C
6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-60 헤테로아릴이고,Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
R
3 및 R
4는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C
1-60 알킬; 치환 또는 비치환된 C
3-60 사이클로알킬; 치환 또는 비치환된 C
2-60 알케닐; 치환 또는 비치환된 C
6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-60 헤테로아릴이고,R 3 and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
a 및 b는 각각 독립적으로, 0 내지 7의 정수이다.a and b are each independently an integer from 0 to 7.
바람직하게는, Ar
3 및 Ar
4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 디벤조티오페닐, 또는 디메틸플루오레닐이다.Preferably, Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
바람직하게는, R
3 및 R
4는 수소이다.Preferably, R 3 and R 4 are hydrogen.
바람직하게는, 상기 화학식 8로 표시되는 화합물은, 구체적으로 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, the compound represented by Formula 8 is any one specifically selected from the group consisting of:
본 발명에 따른 유기 발광 소자는, 발광층에 상기 화학식 1로 표시되는 화합물과 화학식 8로 표시되는 화합물을 조합하여 사용함으로써, 이들의 시너지 효과로 저전압, 고효율, 장수명의 특성을 현저히 향상시킬 수 있다.The organic light emitting device according to the present invention, by using a combination of the compound represented by the formula (1) and the compound represented by the formula (8) in the light emitting layer, these synergistic effects can significantly improve the characteristics of low voltage, high efficiency, long life.
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. Further, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by Chemical Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO
2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SNO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO
2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq
3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light-emitting material is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq
3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조를 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The preparation of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.
[합성예][Synthesis example]
합성예 1: 화합물 1의 합성Synthesis Example 1: Synthesis of Compound 1
단계 1) 화합물 1-1의 합성Step 1) Synthesis of Compound 1-1
질소 분위기에서 3-bromo-2-fluorodibenzo[b,d]furan (15.0g, 56.6mmol)와 bis(pinacolato)diboron (15.8g, 62.2mmol)를 1,4-dioxane 300ml에 환류시키며 교반하였다. 이 후 potassium acetate (8.3g, 84.9mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0) (1.0g, 1.7mmol) 및 tricyclohexylphosphine (1.0g, 3.4mmol)을 투입하였다. 8시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1을 13.2g 제조하였다. (수율 75%, MS: [M+H]+= 313)In a nitrogen atmosphere, 3-bromo-2-fluorodibenzo[b,d]furan (15.0g, 56.6mmol) and bis(pinacolato)diboron (15.8g, 62.2mmol) were refluxed and stirred at 300ml of 1,4-dioxane. After this, potassium acetate (8.3g, 84.9mmol) was added and stirred sufficiently, followed by bis(dibenzylideneacetone)palladium(0) (1.0g, 1.7mmol) and tricyclohexylphosphine (1.0g, 3.4mmol). After 8 hours of reaction and cooling to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of Compound 1-1. (Yield 75%, MS: [M+H] + = 313)
단계 2) 화합물 1-2의 합성Step 2) Synthesis of Compound 1-2
질소 분위기에서 화합물 1-1 (15.0g, 48.1mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2g, 52.9mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate (26.6g, 192.2mmol)를 물 80ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0) (1.7g, 1.4mmol)을 투입하였다. 9시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-2를 14.6g 제조하였다. (수율 73%, MS: [M+H]+= 418)Compound 1-1 (15.0g, 48.1mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2g, 52.9mmol) were added to 300 ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (26.6g, 192.2mmol) was dissolved in 80ml of water, stirred thoroughly, and then tetrakis(triphenylphosphine)palladium(0) (1.7g, 1.4mmol) was added. After the reaction for 9 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6 g of Compound 1-2. (Yield 73%, MS: [M+H] + = 418)
단계 3) 화합물 1의 합성Step 3) Synthesis of Compound 1
질소 분위기에서 화합물 1-2 (20.0g, 47.9mmol)와 4-phenyl-9H-carbazole (12.8g, 52.7mmol)를 DMF 400ml에 넣고 환류시키며 교반하였다. 이 후 cesium carbonate (46.8g, 143.7mmol)를 투입하고 교반하였다. 6시간 반응 후 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화 정제를 통해 화합물 1를 15.0g 제조하였다. (수율 49%, MS: [M+H]+= 642)In a nitrogen atmosphere, compound 1-2 (20.0g, 47.9mmol) and 4-phenyl-9H-carbazole (12.8g, 52.7mmol) were added to 400 ml of DMF and stirred under reflux. After that, cesium carbonate (46.8 g, 143.7 mmol) was added and stirred. After the reaction for 6 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 15.0 g of Compound 1 was prepared through sublimation purification. (Yield 49%, MS: [M+H] + = 642)
합성예 2: 화합물 2의 합성Synthesis Example 2: Synthesis of Compound 2
합성예 1의 단계 3에서, 4-phenyl-9H-carbazole을 2,4-diphenyl-9H-carbazole로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2를 제조하였다. (MS[M+H]
+= 718)In step 3 of Synthesis Example 1, compound 2 was prepared in the same manner as in compound 1, except that 4-phenyl-9H-carbazole was changed to 2,4-diphenyl-9H-carbazole. (MS[M+H] + = 718)
합성예 3: 화합물 3의 합성Synthesis Example 3: Synthesis of Compound 3
합성예 1에서, 3-bromo-2-fluorodibenzo[b,d]furan을 3-chloro-4-fluorodibenzo[b,d]furan로, 4-phenyl-9H-carbazole을 3-phenyl-9H-carbazole로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3을 제조하였다. (MS[M+H]
+= 642)In Synthesis Example 1, 3-bromo-2-fluorodibenzo[b,d]furan is 3-chloro-4-fluorodibenzo[b,d]furan, 4-phenyl-9H-carbazole is 3-phenyl-9H-carbazole Compound 3 was manufactured by the same method as the method of preparing compound 1, except that the mixture was used. (MS[M+H] + = 642)
합성예 4: 화합물 4의 합성Synthesis Example 4: Synthesis of Compound 4
합성예 1에서, 3-bromo-2-fluorodibenzo[b,d]furan을 3-chloro-4-fluorodibenzo[b,d]furan로, 2-chloro-4,6-diphenyl-1,3,5-triazine을 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine로, 4-phenyl-9H-carbazole을 2-phenyl-9H-carbazole로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4를 제조하였다. (MS[M+H]
+= 718)In Synthesis Example 1, 3-bromo-2-fluorodibenzo[b,d]furan is 3-chloro-4-fluorodibenzo[b,d]furan, 2-chloro-4,6-diphenyl-1,3,5- triazine to 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine, 4-phenyl-9H-carbazole to 2-phenyl-9H- Compound 4 was manufactured by the same method as the method of preparing compound 1, except that it was changed to carbazole and used. (MS[M+H] + = 718)
합성예 5: 화합물 5의 합성Synthesis Example 5: Synthesis of Compound 5
단계 1) 화합물 5-1의 합성Step 1) Synthesis of Compound 5-1
질소 분위기에서 1-bromodibenzo[b,d]furan-2-ol (15.0g, 57.0mmol)와 bis(pinacolato)diboron (15.9g, 62.7mmol)를 1,4-dioxane 300ml에 환류시키며 교반하였다. 이 후 potassium acetate (8.4g, 85.5mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0) (1.0g, 1.7mmol) 및 tricyclohexylphosphine (1.0g, 3.4mmol)을 투입하였다. 5시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 5-1을 10.6g 제조하였다. (수율 60%, MS: [M+H]+= 311)In a nitrogen atmosphere, 1-bromodibenzo[b,d]furan-2-ol (15.0g, 57.0mmol) and bis(pinacolato)diboron (15.9g, 62.7mmol) were refluxed and stirred at 300ml of 1,4-dioxane. After this, potassium acetate (8.4g, 85.5mmol) was added and stirred sufficiently, followed by bis(dibenzylideneacetone)palladium(0) (1.0g, 1.7mmol) and tricyclohexylphosphine (1.0g, 3.4mmol). After reacting for 5 hours, cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.6 g of compound 5-1. (Yield 60%, MS: [M+H] + = 311)
단계 2) 화합물 5-2의 합성Step 2) Synthesis of Compound 5-2
질소 분위기에서 화합물 5-1 (15.0g, 48.4mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2g, 53.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate (26.7g, 193.4mmol)를 물 80ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0) (1.7g, 1.5mmol)을 투입하였다. 10시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 5-2를 15.7g 제조하였다. (수율 78%, MS: [M+H]+= 418)Compound 5-1 (15.0 g, 48.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2 g, 53.2 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (26.7g, 193.4mmol) was dissolved in 80ml of water, stirred thoroughly, and then tetrakis(triphenylphosphine)palladium(0) (1.7g, 1.5mmol) was added. After the reaction for 10 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.7 g of compound 5-2. (Yield 78%, MS: [M+H] + = 418)
단계 3) 화합물 5-3의 합성Step 3) Synthesis of Compound 5-3
질소 분위기에서 화합물 5-2 (15.0g, 35.9mmol), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (23.9g, 79.1mmol), potassium carbonate (9.9g, 71.9mmol)를 DMF 225ml에 넣고 교반 및 환류하였다. 5시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 5-3을 18.8g 제조하였다. (수율 75%, MS: [M+H]+= 699)Compound 5-2 in nitrogen atmosphere (15.0g, 35.9mmol), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (23.9g, 79.1mmol), potassium carbonate ( 9.9 g, 71.9 mmol) was added to 225 ml of DMF, stirred and refluxed. After reacting for 5 hours, cooled to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.8 g of compound 5-3. (Yield 75%, MS: [M+H] + = 699)
단계 4) 화합물 5의 합성Step 4) Synthesis of Compound 5
질소 분위기에서 화합물 5-3 (15.0g, 21.5mmol)와 2-phenyl-9H-carbazole (5.8g, 23.7mmol)를 toluene 300ml에 넣고 교반 및 환류하였다. 이 후 sodium tert-butoxide (3.1g, 32.3mmol), bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol)을 투입하였다. 11시간 반응 후 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 5를 6.3g 제조하였다. (수율 46%, MS: [M+H]+= 642)Compound 5-3 (15.0 g, 21.5 mmol) and 2-phenyl-9H-carbazole (5.8 g, 23.7 mmol) were added to 300 ml of toluene in a nitrogen atmosphere, and stirred and refluxed. After this, sodium tert-butoxide (3.1 g, 32.3 mmol) and bis (tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) were added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved again in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 6.3 g of compound 5 was prepared through sublimation purification. (Yield 46%, MS: [M+H] + = 642)
합성예 6: 화합물 6의 합성Synthesis Example 6: Synthesis of Compound 6
합성예 5의 단계 4에서, 2-phenyl-9H-carbazole을 4-(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazole로 변경하여 사용한 것을 제외하고는, 화합물 5의 제조 방법과 동일한 제조 방법으로 화합물 6을 제조하였다. (MS[M+H]
+= 758)In step 4 of Synthesis Example 5, except that 2-phenyl-9H-carbazole was changed to 4-(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazole, the preparation of compound 5 Compound 6 was manufactured by the same method as the method. (MS[M+H] + =758)
합성예 7: 화합물 7의 합성Synthesis Example 7: Synthesis of Compound 7
합성예 5에서, 1-bromodibenzo[b,d]furan-2-ol을 4-bromodibenzo[b,d]thiophen-3-ol로 변경하여 사용한 것을 제외하고는, 화합물 5의 제조 방법과 동일한 제조 방법으로 화합물 7을 제조하였다. (MS[M+H]
+= 658)In Synthesis Example 5, except for using 1-bromodibenzo[b,d]furan-2-ol is changed to 4-bromodibenzo[b,d]thiophen-3-ol, the same production method as in Compound 5 Compound 7 was prepared. (MS[M+H] + = 658)
합성예 8: 화합물 8의 합성Synthesis Example 8: Synthesis of Compound 8
합성예 5에서, 1-bromodibenzo[b,d]furan-2-ol을 4-bromodibenzo[b,d]thiophen-3-ol로, 2-phenyl-9H-carbazole을 1-([1,1'-biphenyl]-4-yl)-9H-carbazole로 변경하여 사용한 것을 제외하고는, 화합물 5의 제조 방법과 동일한 제조 방법으로 화합물 8을 제조하였다. (MS[M+H]
+= 734)In Synthesis Example 5, 1-bromodibenzo[b,d]furan-2-ol is 4-bromodibenzo[b,d]thiophen-3-ol, 2-phenyl-9H-carbazole is 1-([1,1' Compound 8 was prepared by the same method as the method for preparing compound 5, except that -biphenyl]-4-yl)-9H-carbazole was used. (MS[M+H] + = 734)
[실험예][Experimental Example]
실험예 1Experimental Example 1
ITO(Indium Tin Oxide)가 1,300Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.ITO (Indium Tin Oxide) was coated with a thin film coated with a thickness of 1,300 에 in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT-CN)를 50Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공수송층으로 하기 NPB를 150Å 두께로 진공 증착한 후 전자저지층으로 하기 HT-A를 50Å의 두께로 열 진공 증착하였다. 이어서 앞서 제조한 화합물 1와 하기 YGD 화합물을 85:15의 중량비로 200 Å의 두께로 진공 증착하여 발광층을 형성하였다. 이어서, 전자 수송층으로 하기 ET-A 를 200Å의 두께로 열 진공 증착하고 이어서 ET-B와 리튬을 98:2의 중량비로 100Å의 두께로 진공 증착하였다. 상기 전자주입층 위에 순차적으로 마그네슘과 은을 10:1의 비율로 220Å의 두께로, 알루미늄을 1000Å 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.The following hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum-deposited to a thickness of 50 위에 on the prepared ITO transparent electrode to form a hole injection layer. Then, the following NPB was vacuum-deposited to a thickness of 150 MPa as a hole transport layer, and then HT-A, as an electron blocking layer, was thermally vacuum-deposited to a thickness of 50 MPa. Subsequently, the compound 1 and the following YGD compound were vacuum-deposited to a thickness of 200 MPa at a weight ratio of 85:15 to form a light emitting layer. Subsequently, the following ET-A was thermally vacuum-deposited to a thickness of 200 MPa as an electron transport layer, and then ET-B and lithium were vacuum-deposited to a thickness of 100 MPa at a weight ratio of 98:2. On the electron injection layer, magnesium and silver were sequentially deposited at a thickness of 220 로 at a ratio of 10:1, and aluminum was deposited at a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light emitting device.
상기의 과정에서 유기물의 증착속도는 0.4~0.7Å/sec를 유지하였고, 은과 마그네슘은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10
-7 ~ 5×10
-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, and the deposition rate of silver and magnesium was maintained at 2Å/sec, and the vacuum degree during deposition was 2×10 -7 ~ 5×10 -6 torr. By maintaining the, an organic light emitting device was produced.
실험예 2 내지 실험예 8Experimental Example 2 to Experimental Example 8
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.
비교실험예 1 내지 5Comparative Experimental Examples 1 to 5
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서, 화합물 YGH-A, YGH-B, YGH-C, YGH-D 및 YGH-E는 각각 하기와 같다.An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 below was used instead of Compound 1. In Table 1 below, the compounds YGH-A, YGH-B, YGH-C, YGH-D and YGH-E are as follows.
상기 실험예 및 비교 실험예에서 제조한 유기 발광 소자를 110℃ 오븐에서 30분간 보관하여 열처리한 후, 전류를 인가하여 전압, 효율, 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 전압 및 효율은 10 mA/cm
2의 전류 밀도를 인가하여 측정하였다. 또한, 하기 표 1의 T95은 전류 밀도 50 mA/cm
2에서 초기 휘도가 95%로 저하할 때까지 측정한 시간을 의미한다.The organic light emitting device manufactured in the above Experimental Example and Comparative Experimental Example was stored in a 110° C. oven for 30 minutes and heat treated, and then applied with a current to measure voltage, efficiency, and lifetime (T95) and the results are shown in Table 1 below. . At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 50 mA/cm 2 .
| 발광층(호스트)Light emitting layer (host) | 전압(V)Voltage (V) | 효율(cd/A)Efficiency (cd/A) | 수명(T95, hr)Life (T95, hr) | |
| 실험예 1Experimental Example 1 |
화합물 1 |
2.912.91 | 62.162.1 | 3030 |
| 실험예 2Experimental Example 2 |
화합물 2 |
2.902.90 | 62.562.5 | 3232 |
| 실험예 3Experimental Example 3 |
화합물 3 |
3.123.12 | 62.362.3 | 3333 |
| 실험예 4Experimental Example 4 |
화합물 4 |
3.143.14 | 61.561.5 | 3030 |
| 실험예 5Experimental Example 5 |
화합물 5 |
2.952.95 | 59.459.4 | 3737 |
| 실험예 6Experimental Example 6 |
화합물 6 |
2.932.93 | 59.759.7 | 3939 |
| 실험예 7Experimental Example 7 |
화합물 7 |
3.033.03 | 60.960.9 | 4545 |
| 실험예 8Experimental Example 8 |
화합물 8 |
3.063.06 | 61.261.2 | 4343 |
| 비교 실험예 1Comparative Experimental Example 1 | YGH-AYGH-A | 3.813.81 | 43.043.0 | 2121 |
| 비교 실험예 2Comparative Experimental Example 2 | YGH-BYGH-B | 3.853.85 | 41.141.1 | 2727 |
| 비교 실험예 3Comparative Experimental Example 3 | YGH-CYGH-C | 4.254.25 | 26.626.6 | 55 |
| 비교 실험예 4Comparative Experimental Example 4 | YGH-DYGH-D | 4.024.02 | 11.311.3 | 1212 |
| 비교 실험예 5Comparative Experimental Example 5 | YGH-EYGH-E | 4.384.38 | 12.312.3 | 55 |
화학식 1로 표시되는 화합물은 디벤조퓨란 혹은 디벤조티오펜을 중심으로 전자 받개 유닛인 함질소 헤테로 고리와 전자 주개 유닛인 카바졸기가 오쏘 위치로 결합하고 있는 구조를 가지고 있다. 전자 주개 유닛과 전자 받개 유닛이 오쏘로 결합하고 있는 경우 두 치환기가 마주보며 상호작 용하여 intra-charge transfer(ICT) 상태가 발생하며 이 영향으로 밴드갭이 작아지고 보다 긴 파장에서 발광을 하여 황녹색 발광소자의 도펀트로 에너지 전달에 유리해진다. 비교 실험예 1 및 2를 통해 YGH-A와 YGH-B와 같이 두 치환기가 메타 위치나 파라 위치로 치환된 구조들은 화학식 1의 구조에 비해 효율이 저하됨을 확인할 수 있었다.The compound represented by Chemical Formula 1 has a structure in which a nitrogen-containing hetero ring, which is an electron acceptor unit, and a carbazole group, which is an electron donor unit, are bonded to an ortho position centering on dibenzofuran or dibenzothiophene. When the electron donor unit and the electron acceptor unit are combined with an ortho, the two substituents face each other and interact with each other to generate an intra-charge transfer (ICT) state. As a result, the band gap is reduced and light emission occurs at a longer wavelength. The dopant of the light emitting device is advantageous for energy transfer. Through Comparative Experimental Examples 1 and 2, structures in which two substituents, such as YGH-A and YGH-B, were substituted with meta-positions or para-positions, were found to have lower efficiency compared to the structure of Formula 1.
또한, 카바졸에 치환된 아릴기는 카바졸의 전자 주개 능력을 높여주어 ICT가 더 잘 생기도록 하며 동시에 오쏘 위치로 인해 나타날 수 있는 유리전이온도저하를 상쇄하여 열처리 후에도 소자의 높은 안정성을 나타내는데 이는 실험예와 비교 실험예 3과의 비교를 통해 알 수 있다. In addition, the aryl group substituted with carbazole increases the electron donating ability of carbazole to make ICT more prominent, and at the same time, compensates for the glass transition temperature drop that may occur due to the ortho position, thereby showing high stability of the device even after heat treatment. It can be seen through comparison with the example and the comparative example 3.
두 치환기와 디벤조퓨란 혹은 디벤조티오펜이 직접 결합하지 않은 경우 두 치환기가 바로 마주보지 않게 되어 ICT의 형성이 낮아져 전반적인 소자 특성이 저하됨을 확인할 수 있었다.When the two substituents and dibenzofuran or dibenzothiophene were not directly bonded, it was confirmed that the formation of the ICT was lowered and the overall device characteristics were deteriorated because the two substituents were not directly facing each other.
따라서, 표1의 결과로부터 화학식 1로 표시되는 화합물을 유기발광소자의 황녹색 발광층 호스트로 적용 시 비교 실험예에 적용된 화합물과 비교해 보다 우수한 특성을 나타냄을 확인할 수 있다. Accordingly, it can be seen from the results of Table 1 that when the compound represented by Chemical Formula 1 is applied as a yellow-green light emitting layer host of the organic light emitting device, it can be seen that it exhibits superior properties compared to the compound applied in the comparative experimental example.
부호의 설명Explanation of code
1: 기판 2: 양극1: substrate 2: anode
3: 발광층 4: 음극3: light emitting layer 4: cathode
5: 정공주입층 6: 정공수송층5: hole injection layer 6: hole transport layer
7: 발광층 8: 전자수송층7: light emitting layer 8: electron transport layer
Claims (14)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,X는 O 또는 S이고,X is O or S,Y 1, Y 2 및 Y 3는 각각 독립적으로, CH; 또는 N이고, 단, Y 1, Y 2 및 Y 3 중 2개 이상이 N이고,Y 1 , Y 2 and Y 3 are each independently CH; Or N, provided that at least two of Y 1 , Y 2 and Y 3 are N,Ar 1 및 Ar 2는 각각 독립적으로, 치환 또는 비치환된 C 6-60 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 하나 이상의 헤테로 원자를 포함하는 치환 또는 비치환된 C 5-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 5-60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O and S,상기 두 개의 *는 각각 1 및 2; 2 및 3; 또는 3 및 4와 연결되고,The two * are 1 and 2, respectively; 2 and 3; Or 3 and 4,R 1은 수소; 중수소; 치환 또는 비치환된 C 1-60 알킬; 또는 치환 또는 비치환된 C 6-60 아릴이고,R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,R 2는 치환 또는 비치환된 C 6-60 아릴이고,R 2 is substituted or unsubstituted C 6-60 aryl,m은 0 내지 6의 정수이고,m is an integer from 0 to 6,n은 1 내지 8의 정수임.n is an integer from 1 to 8. - 제 1항에 있어서, According to claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 7로 표시되는 화합물 중에서 선택되는 어느 하나인, 화합물:The compound represented by Formula 1 is any one selected from compounds represented by Formulas 2 to 7 below:[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 2 내지 7에서,In the above formula 2 to 7,X, Y 1, Y 2, Y 3, Ar 1, Ar 2, R 1, R 2, n 및 m은 청구항 1에서 정의한 바와 같음.X, Y 1 , Y 2 , Y 3 , Ar 1 , Ar 2 , R 1 , R 2 , n and m are as defined in claim 1. - 제 1항에 있어서, According to claim 1,Ar 1 및 Ar 2은 각각 독립적으로, 페닐; 비페닐릴; 터페닐릴; 나프틸; 안트라세닐; 페난쓰레닐; 트리페닐레닐; 디메틸플루오레닐; 디벤조퓨라닐 또는 디벤조티오페닐인, 화합물.Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Dibenzofuranyl or dibenzothiophenyl.
- 제 1항에 있어서, According to claim 1,Ar 1 및 Ar 2은 각각 독립적으로, 페닐; 비페닐릴; 또는 디벤조퓨라닐인, 화합물.Ar 1 and Ar 2 are each independently phenyl; Biphenylyl; Or dibenzofuranyl.
- 제 1항에 있어서, According to claim 1,R 1은 수소; 또는 중수소인, 화합물.R 1 is hydrogen; Or deuterium.
- 제 1항에 있어서, According to claim 1,R 2는 페닐; 비페닐릴; 터페닐릴; 나프틸; 안트라세닐; 페난쓰레닐; 트리페닐레닐; 또는 디메틸플루오레닐인, 화합물.R 2 is phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Or dimethylfluorenyl.
- 제 1항에 있어서, According to claim 1,n은 1 또는 2인, 화합물.n is 1 or 2, a compound.
- 제 1항에 있어서, According to claim 1,상기 화학식 1로 표시되는 화합물은, 하기로 구성되는 군으로부터 선택되는 어느 하나인, 화합물: The compound represented by Formula 1 is any one selected from the group consisting of:
.
. - 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 제 1항 내지 제 8항 중 어느 하나의 항에 따른 화합물을 포함하는 것인, 유기 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. That is, an organic light emitting device.
- 제9항에 있어서,The method of claim 9,상기 유기물층은 발광층인, 유기 발광 소자.The organic material layer is an organic light emitting device, a light emitting layer.
- 제10항에 있어서,The method of claim 10,상기 발광층은 하기 화학식 8로 표시되는 화합물을 추가로 포함하는, 유기 발광 소자:The light emitting layer further comprises a compound represented by the formula (8), an organic light emitting device:[화학식 8][Formula 8]
상기 화학식 8에서,In Chemical Formula 8,Ar 3 및 Ar 4는 각각 독립적으로, 치환 또는 비치환된 C 6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C 2-60 헤테로아릴이고,Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,R 3 및 R 4는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C 1-60 알킬; 치환 또는 비치환된 C 3-60 사이클로알킬; 치환 또는 비치환된 C 2-60 알케닐; 치환 또는 비치환된 C 6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C 2-60 헤테로아릴이고,R 3 and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,a 및 b는 각각 독립적으로, 0 내지 7의 정수임.a and b are each independently an integer from 0 to 7. - 제11항에 있어서,The method of claim 11,Ar 3 및 Ar 4는 각각 독립적으로, 페닐; 비페닐릴; 터페닐릴; 나프틸; 디벤조퓨라닐; 디벤조티오페닐; 또는 디메틸플루오레닐인, 유기 발광 소자.Ar 3 and Ar 4 are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Dibenzofuranyl; Dibenzothiophenyl; Or dimethyl fluorenyl, an organic light emitting device.
- 제11항에 있어서,The method of claim 11,R 3 및 R 4는 수소인, 유기 발광 소자.R 3 and R 4 are hydrogen, the organic light emitting device.
- 제11항에 있어서,The method of claim 11,상기 화학식 8로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인, 유기 발광 소자:The compound represented by Chemical Formula 8 is any one selected from the group consisting of:
.
.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202080005477.2A CN112789275A (en) | 2019-01-18 | 2020-01-16 | Novel compound and organic light emitting device comprising same |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20190007096 | 2019-01-18 | ||
| KR10-2019-0007096 | 2019-01-18 | ||
| KR10-2020-0005489 | 2020-01-15 | ||
| KR1020200005489A KR102354501B1 (en) | 2019-01-18 | 2020-01-15 | Novel compound and organic light emitting device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2020149656A1 true WO2020149656A1 (en) | 2020-07-23 |
Family
ID=71613833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2020/000781 WO2020149656A1 (en) | 2019-01-18 | 2020-01-16 | Novel compound and organic light-emitting diode using same |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2020149656A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4335846A1 (en) | 2022-06-30 | 2024-03-13 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150134248A (en) * | 2014-05-21 | 2015-12-01 | 삼성전자주식회사 | Carbazole-based compound and organic light emitting device including the same |
| KR20170102000A (en) * | 2015-02-13 | 2017-09-06 | 코니카 미놀타 가부시키가이샤 | Aromatic heterocyclic derivatives, organic electroluminescent devices using the same, lighting devices and display devices |
| KR20180068869A (en) * | 2016-12-14 | 2018-06-22 | 주식회사 엘지화학 | Organic light emitting device |
| KR20180071621A (en) * | 2016-12-20 | 2018-06-28 | 희성소재 (주) | Organic light emitting device and composition for organic layer of organic light emitting device |
| KR20180096444A (en) * | 2017-02-21 | 2018-08-29 | 희성소재 (주) | Organic light emitting device |
-
2020
- 2020-01-16 WO PCT/KR2020/000781 patent/WO2020149656A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150134248A (en) * | 2014-05-21 | 2015-12-01 | 삼성전자주식회사 | Carbazole-based compound and organic light emitting device including the same |
| KR20170102000A (en) * | 2015-02-13 | 2017-09-06 | 코니카 미놀타 가부시키가이샤 | Aromatic heterocyclic derivatives, organic electroluminescent devices using the same, lighting devices and display devices |
| KR20180068869A (en) * | 2016-12-14 | 2018-06-22 | 주식회사 엘지화학 | Organic light emitting device |
| KR20180071621A (en) * | 2016-12-20 | 2018-06-28 | 희성소재 (주) | Organic light emitting device and composition for organic layer of organic light emitting device |
| KR20180096444A (en) * | 2017-02-21 | 2018-08-29 | 희성소재 (주) | Organic light emitting device |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4335846A1 (en) | 2022-06-30 | 2024-03-13 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2017179911A1 (en) | Compound, and organic electronic element comprising same | |
| WO2015152650A1 (en) | Heterocyclic compound and organic light-emitting element comprising same | |
| WO2021080368A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2020111733A1 (en) | Organic light emitting device | |
| WO2020171532A1 (en) | Compound and organic light-emitting element comprising same | |
| WO2019160315A1 (en) | Heterocyclic compound and organic light emitting device comprising same | |
| WO2020149596A1 (en) | Novel compound and organic light emitting diode using same | |
| WO2021091173A1 (en) | Novel compound and organic light emitting device using same | |
| WO2021125648A1 (en) | Novel compound, and organic light-emitting element using same | |
| WO2021066351A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2021080254A1 (en) | Novel compound and organic light emitting device comprising same | |
| WO2020149609A1 (en) | Organic light emitting diode | |
| WO2020111585A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2022031028A1 (en) | Novel compound and organic light emitting device using same | |
| WO2020149656A1 (en) | Novel compound and organic light-emitting diode using same | |
| WO2022059923A1 (en) | Novel compound and organic light-emitting device comprising same | |
| WO2022031013A1 (en) | Novel compound and organic light-emitting device comprising same | |
| WO2022031016A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2021210774A1 (en) | Novel compound and organic light-emitting element comprising same | |
| WO2021066350A1 (en) | Novel compound and organic light emitting device using same | |
| WO2021033980A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2021040467A1 (en) | Novel heterocyclic compound and organic light-emitting device using same | |
| WO2021162227A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2021029715A1 (en) | Novel compound and organic light emitting device comprising same | |
| WO2020185054A9 (en) | Novel compound and organic light emitting device using same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20740912 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 20740912 Country of ref document: EP Kind code of ref document: A1 |