WO2020130509A1 - Organic compound and organic electroluminescent element comprising same - Google Patents
Organic compound and organic electroluminescent element comprising same Download PDFInfo
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- WO2020130509A1 WO2020130509A1 PCT/KR2019/017699 KR2019017699W WO2020130509A1 WO 2020130509 A1 WO2020130509 A1 WO 2020130509A1 KR 2019017699 W KR2019017699 W KR 2019017699W WO 2020130509 A1 WO2020130509 A1 WO 2020130509A1
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- group
- alkyl
- aryl
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- 150000002894 organic compounds Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 239000011368 organic material Substances 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004429 atom Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 16
- 125000005264 aryl amine group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- -1 alkyl boron Chemical compound 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 106
- 238000003786 synthesis reaction Methods 0.000 description 106
- 239000010410 layer Substances 0.000 description 99
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000005259 measurement Methods 0.000 description 48
- 239000000463 material Substances 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 29
- 239000012044 organic layer Substances 0.000 description 28
- MPIJGSAWPMMKMU-UHFFFAOYSA-N 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C=1C=CC2=C(OC3=C2C=CC=C3)C=1)C1=CC=CC=C1 MPIJGSAWPMMKMU-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000000605 extraction Methods 0.000 description 16
- 0 CC*(C([C@](*)N)=*C(*C(C)**)=*)=C(C)CC*N Chemical compound CC*(C([C@](*)N)=*C(*C(C)**)=*)=C(C)CC*N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 8
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 8
- 101150003085 Pdcl gene Proteins 0.000 description 8
- 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 8
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- VAKXVDUJGANVGE-UHFFFAOYSA-N 4-bromo-6-chlorodibenzofuran Chemical compound C12=CC=CC(Br)=C2OC2=C1C=CC=C2Cl VAKXVDUJGANVGE-UHFFFAOYSA-N 0.000 description 3
- VKXPQEXVMLWOMU-UHFFFAOYSA-N 6-chloro-1-dibenzothiophen-1-yldibenzothiophene Chemical compound C1=CC=C2C(=C1)C3=C(C=CC=C3S2)C4=C5C6=C(C(=CC=C6)Cl)SC5=CC=C4 VKXPQEXVMLWOMU-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 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 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 2
- MTQVNVJTIGCAFZ-UHFFFAOYSA-N 2-dibenzothiophen-3-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C3=CC=CC=C3SC2=C1 MTQVNVJTIGCAFZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- SMXOYOITROKZCI-UHFFFAOYSA-N 4-chloro-6-dibenzothiophen-3-yldibenzofuran Chemical compound ClC1=CC=CC2=C1OC1=C2C=CC=C1C=1C=CC2=C(SC3=C2C=CC=C3)C1 SMXOYOITROKZCI-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 2
- STZOSVMLVHJZJV-UHFFFAOYSA-N 6-chloro-1-dibenzofuran-1-yldibenzofuran Chemical compound C1=CC=C2C(=C1)C3=C(C=CC=C3O2)C4=C5C6=C(C(=CC=C6)Cl)OC5=CC=C4 STZOSVMLVHJZJV-UHFFFAOYSA-N 0.000 description 2
- RZSRPJWLSGUIGG-UHFFFAOYSA-N CC1(C)OB(c(cc2)cc3c2c(cccc2-c(cc4)cc5c4c(cccc4)c4[o]5)c2[o]3)OC1(C)C Chemical compound CC1(C)OB(c(cc2)cc3c2c(cccc2-c(cc4)cc5c4c(cccc4)c4[o]5)c2[o]3)OC1(C)C RZSRPJWLSGUIGG-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
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- 239000011787 zinc oxide Substances 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- WDLIHZYHOAAWHL-UHFFFAOYSA-N 1-(7-chlorodibenzothiophen-4-yl)dibenzofuran Chemical compound ClC1=CC2=C(C3=C(S2)C(=CC=C3)C3=CC=CC=2OC4=C(C23)C=CC=C4)C=C1 WDLIHZYHOAAWHL-UHFFFAOYSA-N 0.000 description 1
- NSBVZIPOYWJVJJ-UHFFFAOYSA-N 1-bromo-6-chlorodibenzothiophene Chemical compound S1C2=CC=CC(Br)=C2C2=C1C(Cl)=CC=C2 NSBVZIPOYWJVJJ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- PZLAHPLHCCHMOX-UHFFFAOYSA-N 2-bromo-6-chlorodibenzothiophene Chemical compound C12=CC(Br)=CC=C2SC2=C1C=CC=C2Cl PZLAHPLHCCHMOX-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- VJDXNNHLTDFBRI-UHFFFAOYSA-N 2-dibenzothiophen-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC2=C1C1=CC=CC=C1S2 VJDXNNHLTDFBRI-UHFFFAOYSA-N 0.000 description 1
- CALTYNDKBHMXQA-UHFFFAOYSA-N 2-dibenzothiophen-2-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=2C3=CC=CC=2)C3=C1 CALTYNDKBHMXQA-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- BIHIGIKUKSSVCZ-UHFFFAOYSA-N 3-bromo-6-chlorodibenzofuran Chemical compound BrC=1C=CC2=C(OC3=C2C=CC=C3Cl)C=1 BIHIGIKUKSSVCZ-UHFFFAOYSA-N 0.000 description 1
- CYQWUOLZRKUHNU-UHFFFAOYSA-N 4-bromo-6-chlorodibenzothiophene Chemical compound C12=CC=CC(Br)=C2SC2=C1C=CC=C2Cl CYQWUOLZRKUHNU-UHFFFAOYSA-N 0.000 description 1
- GVTFGZISLQBJBK-UHFFFAOYSA-N 6-bromo-3-chlorodibenzofuran Chemical compound BrC1=CC=CC=2C3=C(OC=21)C=C(C=C3)Cl GVTFGZISLQBJBK-UHFFFAOYSA-N 0.000 description 1
- UQQPNDWVZHRPCW-UHFFFAOYSA-N 6-bromo-3-chlorodibenzothiophene Chemical compound C1=CC=C2C3=CC=C(Cl)C=C3SC2=C1Br UQQPNDWVZHRPCW-UHFFFAOYSA-N 0.000 description 1
- GYELORJYENLFND-UHFFFAOYSA-N 7-chloro-1-dibenzofuran-1-yldibenzofuran Chemical compound ClC1=CC2=C(C=C1)C1=C(O2)C=CC=C1C1=CC=CC2=C1C1=C(O2)C=CC=C1 GYELORJYENLFND-UHFFFAOYSA-N 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- BCIXRGMSNJDCMA-UHFFFAOYSA-N CC1(C)OB(c2c3[o]c(cc(cc4)-c(cc5)cc6c5c(cccc5)c5[o]6)c4c3ccc2)OC1(C)C Chemical compound CC1(C)OB(c2c3[o]c(cc(cc4)-c(cc5)cc6c5c(cccc5)c5[o]6)c4c3ccc2)OC1(C)C BCIXRGMSNJDCMA-UHFFFAOYSA-N 0.000 description 1
- KGPDRHHSRKCQGL-UHFFFAOYSA-N CC1(C)OB(c2cccc(c3ccc4)c2[s]c3c4-c2c3[s]c4ccccc4c3ccc2)OC1(C)C Chemical compound CC1(C)OB(c2cccc(c3ccc4)c2[s]c3c4-c2c3[s]c4ccccc4c3ccc2)OC1(C)C KGPDRHHSRKCQGL-UHFFFAOYSA-N 0.000 description 1
- CKQXGVLPVWNAIS-UHFFFAOYSA-N CC1(OB(OC1(C)C)C1=CC=CC=2OC3=C(C=21)C=CC=C3)C Chemical compound CC1(OB(OC1(C)C)C1=CC=CC=2OC3=C(C=21)C=CC=C3)C CKQXGVLPVWNAIS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VJUDVBGAPXOIMA-UHFFFAOYSA-N Cc1cccc(c2ccc3)c1[s]c2c3-c1c2[s]c(cccc3)c3c2ccc1 Chemical compound Cc1cccc(c2ccc3)c1[s]c2c3-c1c2[s]c(cccc3)c3c2ccc1 VJUDVBGAPXOIMA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- JIHNZNBRECXPJB-UHFFFAOYSA-N Clc1nc(-c2ccccc2)nc(-[n]2c3ccccc3c3c2cccc3)n1 Chemical compound Clc1nc(-c2ccccc2)nc(-[n]2c3ccccc3c3c2cccc3)n1 JIHNZNBRECXPJB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- JIGLWRORIBYWHJ-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-c(cc2)cc3c2c(cccc2-c4ccc(c5ccccc5[o]5)c5c4)c2[o]3)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-c(cc2)cc3c2c(cccc2-c4ccc(c5ccccc5[o]5)c5c4)c2[o]3)n1 JIGLWRORIBYWHJ-UHFFFAOYSA-N 0.000 description 1
- QVCOLSILHXRRJW-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)cc3c2c2cccc(-c(cc4)cc5c4c4ccccc4[o]5)c2[o]3)nc(-[n]2c(cccc3)c3c3c2cccc3)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)cc3c2c2cccc(-c(cc4)cc5c4c4ccccc4[o]5)c2[o]3)nc(-[n]2c(cccc3)c3c3c2cccc3)n1 QVCOLSILHXRRJW-UHFFFAOYSA-N 0.000 description 1
- PPNPPDBYUYQISG-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2cccc3c2[o]c2cc(-c(cc4)cc5c4c4ccccc4[o]5)ccc32)nc(-c2ccc(c3ccccc3[o]3)c3c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2cccc3c2[o]c2cc(-c(cc4)cc5c4c4ccccc4[o]5)ccc32)nc(-c2ccc(c3ccccc3[o]3)c3c2)n1 PPNPPDBYUYQISG-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 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
- 230000005283 ground state Effects 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
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 230000006872 improvement Effects 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
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- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 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
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- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 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
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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 organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.
- the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
- the luminescent material may be divided into blue, green, and red luminescent materials, and yellow and orange luminescent materials for realizing a better natural color according to the luminous color.
- a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB, BCP, and Alq 3 are widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer material, and anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
- the present invention can be applied to an organic electroluminescent device, and has an object to provide a novel organic compound having excellent holes, electron injection and transport ability, and luminescence ability.
- Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
- X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
- L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
- Ar 1 is a substituent represented by the following formula (2),
- Ar 2 is a substituent represented by the following formula (3),
- Ar 3 is a C 6 ⁇ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms
- Y 1 and Y 2 are each independently O or S,
- Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
- a and b are each independently an integer from 0 to 4
- R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group selected from the group consisting of, or
- the arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryl of C 60 Oxy group, C 1 ⁇ C 40 alkyloxy group, C 6
- the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers of the one or more layers comprises the compound of Formula 1 .
- Alkyl in the present invention is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but is not limited thereto.
- Alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
- Alkynyl in the present invention is a monovalent substituent derived from a straight chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, for example, ethynyl , 2-propynyl, and the like, but is not limited thereto.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings.
- two or more rings are condensed with each other, and contain only carbon as a ring forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule is monovalent with non-aromacity.
- Substituents may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, and fluorenyl, but are not limited thereto.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and as ring-forming atoms, hetero atoms selected from among N, O, P, S, and Se other than carbon are included, and the whole molecule is non-aromatic (non-aromatic). It is interpreted as including a monovalent group having aromacity).
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
- Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
- Alkyloxy in the present invention is a monovalent substituent represented by R O-, wherein R means 1 to 40 alkyl, and includes a linear, branched or cyclic structure. It is interpreted as. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, It is substituted with a hetero atom such as S or Se.
- heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
- Alkylsilyl in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound of the present invention is excellent in thermal stability, carrier transport ability, luminescence ability, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
- FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
- FIG. 2 is a sectional view showing an organic electroluminescent device according to an embodiment of the present invention.
- the novel compound of the present invention has a form in which bis-dibenzomoiety and an azine-based compound are combined as a basic skeleton, and is specifically characterized by being represented by the following Chemical Formula 1.
- X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
- L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
- Ar 1 is a substituent represented by the following formula (2),
- Ar 2 is a substituent represented by the following formula (3),
- Ar 3 is a C 6 ⁇ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms
- Y 1 and Y 2 are each independently O or S,
- Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
- a and b are each independently an integer from 0 to 4
- R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group selected from the group consisting of, or
- the arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryl of C 60 Oxy group, C 1 ⁇ C 40 alkyloxy group, C 6
- Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.).
- EWG electron withdrawing group
- a nitrogen-containing heterocycle eg, pyridine group, pyrimidine group, triazine group, etc.
- the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (green or red phosphorescent host material), an electron transport layer/injection layer material, a light emitting layer material, an electron transport auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material.
- the performance of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
- Ar 1 may be a substituent represented by any one of the following A-1 to A-10.
- Y1 and Y2 are as defined in Chemical Formula 1.
- Ar 2 may be a substituent represented by any one of the following B-1 to B-9.
- Ring A is a 5-6 membered cycloalkyl, phenyl or a 5-6 membered heteroaryl,
- R 2 to R 4 are as defined in Formula 1 of claim 1,
- Y 3 and Y 4 are each independently O or S.
- Ar 3 may be a substituent represented by any one of the following C-1 to C-6.
- Y 5 and Y 6 are each independently selected from the group consisting of a single bond, N(R 10 ), C(R 11 )(R 12 ), O and S, but both Y 5 and Y 6 are not single bonds,
- R 8 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group is selected from the group consisting of
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R 8 to R 12 Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C Alkynyl group of 2 ⁇ C 40 , aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ⁇ C 60 , alkyloxy group of C 1 ⁇ C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalky
- the compound of the present invention may be specifically represented by compounds having the structure illustrated below, but is not limited thereto.
- the compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ) Etc.). The detailed synthesis process for the compounds of the present invention will be described in detail in the synthesis examples described later.
- organic electroluminescent device comprising the compound represented by Chemical Formula 1 according to the present invention.
- the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by the formula (1). At this time, the compound may be used alone or in combination of two or more.
- the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic material layer includes a compound represented by Formula 1 Can.
- the structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, the positive electrode 10 and the negative electrode 20 facing each other, and the positive electrode 10 and the negative electrode ( 20) includes an organic layer 30 located between.
- the organic layer 30 may include a hole transport layer 31, a light emitting layer 32 and an electron transport layer 34.
- a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
- an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
- the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode Between 20, the electron injection layer 36 may be further included.
- the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 improves the interfacial properties between ITO used as the anode and the organic material used as the hole transport layer 31.
- it is a layer that functions to make the surface of ITO smooth by being applied to the top of ITO where the surface is not flat, and can be used without particular limitation as long as it is commonly used in the art, for example, an amine compound can be used. It is not limited to this.
- the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate electron injection from the cathode to ultimately improve power efficiency, and is commonly used in the art. If it can be used can be used without particular limitation, for example, LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
- a hole transport auxiliary layer 33 may be further included between the hole transport layer 31 and the light emitting layer 32.
- the hole transport auxiliary layer 33 may serve to transport holes to the light emitting layer 32 while adjusting the thickness of the organic layer 30.
- the hole transport auxiliary layer 33 may include a hole transport material, and may be made of the same material as the hole transport layer 31.
- an electron transport auxiliary layer 35 may be further included between the electron transport layer 34 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the electron transport auxiliary layer 35 and do not diffuse or move to the electron transport layer 34, resulting in holes. It functions to limit the light emitting layer 32. The function of limiting holes to the light-emitting layer 32 prevents holes from being diffused into the electron transport layer 34 that transfers electrons by reduction, thereby suppressing a decrease in lifespan through irreversible decomposition reaction due to oxidation, and organic light emission. It can contribute to improving the life of the device.
- Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.).
- EWG electron withdrawing group
- a nitrogen-containing heterocycle eg, pyridine group, pyrimidine group, triazine group, etc.
- the compound represented by Chemical Formula 1 which is the representative claim structure of the present invention, has excellent light emission properties
- the hole injection layer 37, the hole transport layer 31, the light emitting layer 32, and the electron as the organic material layer of the organic electroluminescent device It can be used as a material of any one of the transport layer 34 and the electron injection layer 36.
- it can be used as the material for the electron transport layer 34 and the electron auxiliary transport layer 35.
- the organic electroluminescent device may include an anode, one or more organic material layers, and a cathode sequentially stacked as described above, and may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.
- the organic electroluminescent device of the present invention is a material and method known in the art, except that at least one (eg, electron transport auxiliary layer) of the organic material layer is formed to contain the compound represented by the formula (1) It may be manufactured by forming another organic material layer and an electrode.
- at least one (eg, electron transport auxiliary layer) of the organic material layer is formed to contain the compound represented by the formula (1) It may be manufactured by forming another organic material layer and an electrode.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
- the substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet may be used.
- the positive electrode material may be made of a conductor having a high work function to facilitate hole injection, for example, a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy 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 polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
- a conductor having a high work function to facilitate hole injection for example, a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide
- the negative electrode material may be made of a conductor having a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- a green organic electroluminescent device was prepared as follows.
- the glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone or methanol
- UV ozone cleaner Power sonic 405, Hwashin Tech
- Example B-1 When forming the green light emitting layer in Example B-1, an organic EL device was manufactured in the same manner as Compound A-10 used as a green light emitting material.
- a green organic electroluminescent device was manufactured in the same manner as in Example A-1, except that Compound A-10 was not used in Example A-1.
- the green organic electroluminescent devices green organic electroluminescent devices manufactured in Examples A-1 to A-32, respectively using the compound according to the present invention as a luminescent material, only CBP of the conventional light emitting layer It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the green organic electroluminescent element used as a material (the organic electroluminescent element of Comparative Example 1).
- the glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone or methanol
- UV ozone cleaner Power sonic 405, Hwashin Tech
- Example B-1 When forming the electron transport layer in Example B-1, an organic EL device was manufactured by performing the same procedure instead of Compound A-10 used as the electron transport layer material.
- An organic EL device was manufactured in the same manner as in Example B-1, except that Alq3 was used as the electron transporting layer material instead of Compound A-10 used as the electron transporting layer material when forming the electron transporting layer in Example B-1.
- DS-205 and DS-405 used for device fabrication are products of Doosan Electronics BG Co., Ltd., and the structures of NPB, ADN and Alq3 are as follows.
- the organic EL devices using the compound according to the present invention as an electron transport layer are organic EL devices using conventional Alq (comparison) It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the organic EL device of Example 2).
- the present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent element comprising same. The compound according to the present invention is used for an organic material layer of an organic electroluminescent element, preferably for a light emitting layer, so as to improve the luminous efficiency, driving voltage, lifespan, etc., of the organic electroluminescent element.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.
1950년대 베르나노스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.From the observation of organic thin film emission of Bernanose in the 1950s, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 continued, followed by Tang in 1987 The organic electroluminescent device having a layered structure divided by a functional layer of a hole layer and a light emitting layer was proposed. Since then, in order to make a high-efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The luminescent material may be divided into blue, green, and red luminescent materials, and yellow and orange luminescent materials for realizing a better natural color according to the luminous color. In addition, a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times that of the fluorescence, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.
현재까지 정공 주입층, 정공 수송층, 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.To date, NPB, BCP, and Alq 3 are widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer material, and anthracene derivatives have been reported as the light emitting layer material. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layers have an advantage in terms of luminescence properties, but are not satisfactory in terms of lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is very poor. Therefore, development of an organic material layer material having excellent performance is required.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 정공, 전자 주입 및 수송능, 발광능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다.The present invention can be applied to an organic electroluminescent device, and has an object to provide a novel organic compound having excellent holes, electron injection and transport ability, and luminescence ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by Formula 1:
[화학식 1][Formula 1]
상기 화학식 1 에서,In Chemical Formula 1,
X1, 내지 X3은 각각 독립적으로 N 또는 C(R1)이나, 적어도 하나 이상은 N이고,X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
L1 내지 L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 C6~C40의 아릴렌기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
Ar1은 하기 화학식 2로 표시되는 치환기이고,Ar 1 is a substituent represented by the following formula (2),
Ar2는 하기 화학식 3으로 표시되는 치환기이며,Ar 2 is a substituent represented by the following formula (3),
Ar3은 C6~C18의 아릴기 또는 핵원자수 5 내지 18개의 헤테로아릴기이고,Ar 3 is a C 6 ~ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms,
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 내지 3에서,In Chemical Formulas 2 to 3,
*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,
Y1 및 Y2는 각각 독립적으로 O 또는 S이며,Y 1 and Y 2 are each independently O or S,
Z1 및 Z2는 각각 독립적으로 단일결합, N(R2), C(R3)(R4), O, S, P(R5) 및 Si(R6)(R7)로 구성된 군에서 선택되나, Z1 및 Z2가 모두 단일결합은 아니고,Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
a 및 b는 각각 독립적으로 0 내지 4의 정수이며a and b are each independently an integer from 0 to 4
R1 내지 R7은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며,R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl Boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups condensed ring To form,
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ alkyl group of C 40, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryl of C 60 Oxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 1 ~ C 40 alkyl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 When substituted with one or more substituents selected from the group consisting of -C 60 arylsilyl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers of the one or more layers comprises the compound of Formula 1 .
본 발명에서의 "알킬" 은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but is not limited thereto.
본 발명에서의 "알케닐(alkenyl)" 은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
본 발명에서의 "알키닐(alkynyl)" 은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다.“Alkynyl” in the present invention is a monovalent substituent derived from a straight chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, for example, ethynyl , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 "아릴" 은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. In addition, two or more rings are condensed with each other, and contain only carbon as a ring forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule is monovalent with non-aromacity. Substituents may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, and fluorenyl, but are not limited thereto.
본 발명에서의 "헤테로아릴" 은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다.“Heteroaryl” in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and as ring-forming atoms, hetero atoms selected from among N, O, P, S, and Se other than carbon are included, and the whole molecule is non-aromatic (non-aromatic). It is interpreted as including a monovalent group having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
본 발명에서의 "아릴옥시" 는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다."Aryloxy" in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
본 발명에서의 "알킬옥시" 는 R O-로 표시되는 1가의 치환기로, 상기 R 는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다."Alkyloxy" in the present invention is a monovalent substituent represented by R O-, wherein R means 1 to 40 alkyl, and includes a linear, branched or cyclic structure. It is interpreted as. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서의 "아릴아민" 은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬" 은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.“Cycloalkyl” in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 "헤테로시클로알킬" 은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, It is substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
본 발명에서의 "알킬실릴" 은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴" 은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다."Alkylsilyl" in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 "축합 고리" 는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명의 화합물은 열적 안정성, 캐리어 수송능, 발광능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability, carrier transport ability, luminescence ability, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
도 1은 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
도 2는 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.2 is a sectional view showing an organic electroluminescent device according to an embodiment of the present invention.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New organic compounds
본 발명의 신규 화합물은 비스디벤조모이어티(Bis-Dibenzomoiety)와 아진계 화합물이 결합된 형태를 기본 골격으로 하며, 구체적으로는 하기 화학식 1로 표시되는 것을 특징으로 한다.The novel compound of the present invention has a form in which bis-dibenzomoiety and an azine-based compound are combined as a basic skeleton, and is specifically characterized by being represented by the following Chemical Formula 1.
[화학식 1][Formula 1]
상기 화학식 1 에서,In Chemical Formula 1,
X1, 내지 X3은 각각 독립적으로 N 또는 C(R1)이나, 적어도 하나 이상은 N이고,X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
L1 내지 L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 C6~C40의 아릴렌기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
Ar1은 하기 화학식 2로 표시되는 치환기이고,Ar 1 is a substituent represented by the following formula (2),
Ar2는 하기 화학식 3으로 표시되는 치환기이며,Ar 2 is a substituent represented by the following formula (3),
Ar3은 C6~C18의 아릴기 또는 핵원자수 5 내지 18개의 헤테로아릴기이고,Ar 3 is a C 6 ~ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms,
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 내지 3에서,In Chemical Formulas 2 to 3,
*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,
Y1 및 Y2는 각각 독립적으로 O 또는 S이며,Y 1 and Y 2 are each independently O or S,
Z1 및 Z2는 각각 독립적으로 단일결합, N(R2), C(R3)(R4), O, S, P(R5) 및 Si(R6)(R7)로 구성된 군에서 선택되나, Z1 및 Z2가 모두 단일결합은 아니고,Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
a 및 b는 각각 독립적으로 0 내지 4의 정수이며a and b are each independently an integer from 0 to 4
R1 내지 R7은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며,R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl Boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups condensed ring To form,
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ alkyl group of C 40, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryl of C 60 Oxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 1 ~ C 40 alkyl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 When substituted with one or more substituents selected from the group consisting of -C 60 arylsilyl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 화합물은 비스디벤조모이어티(Bis-Dibenzomoiety)가 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)와 결합되어, 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있고 녹색인광호스트 및 전자 수송층에 적용 시 저전압, 고효율, 장수명의 특성을 나타낼 수 있다.In the compound of the present invention, Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.). , Since the whole molecule has a bipolar characteristic, it can increase the bonding force between holes and electrons, and when applied to a green phosphorescent host and an electron transport layer, it can exhibit characteristics of low voltage, high efficiency, and long life.
따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(녹색 또는 적색의 인광 호스트 재료), 전자 수송층/주입층 재료 발광층 재료, 전자 수송 보조층 재료, 더욱 바람직하게는 발광층 재료, 전자 수송층 재료, 전자 수송 보조층 재료로 사용될 수 있다. 또한, 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (green or red phosphorescent host material), an electron transport layer/injection layer material, a light emitting layer material, an electron transport auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material. In addition, the performance of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 A-1 내지 A-10 중 어느 하나로 표시되는 치환기인 것일 수 있다.According to a preferred embodiment of the present invention, Ar 1 may be a substituent represented by any one of the following A-1 to A-10.
상기 A-1 내지 A-10에서, Y1 및 Y2는 상기 화학식 1에서 정의된 바와 같다.In A-1 to A-10, Y1 and Y2 are as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar2는 하기 B-1 내지 B-9 중 어느 하나로 표시되는 치환기일 수 있다.According to a preferred embodiment of the present invention, Ar 2 may be a substituent represented by any one of the following B-1 to B-9.
상기 B-1 내지 B-9에서,In B-1 to B-9,
*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,
고리 A는 5 내지 6원의 사이클로알킬, 페닐 또는 5 내지 6원의 헤테로아릴이며,Ring A is a 5-6 membered cycloalkyl, phenyl or a 5-6 membered heteroaryl,
R2 내지 R4는 제1항의 화학식 1에서 정의된 바와 같고,R 2 to R 4 are as defined in Formula 1 of claim 1,
Y3 및 Y4는 각각 독립적으로 O 또는 S이다.Y 3 and Y 4 are each independently O or S.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar3은 하기 C-1 내지 C-6 중 어느 하나로 표시되는 치환기일 수 있다.According to a preferred embodiment of the present invention, Ar 3 may be a substituent represented by any one of the following C-1 to C-6.
상기 C-1 내지 C-6에서,In the above C-1 to C-6,
*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,
Y5 및 Y6은 각각 독립적으로 단일결합, N(R10), C(R11)(R12), O 및 S로 구성된 군에서 선택되나, Y5 및 Y6이 모두 단일결합은 아니고,Y 5 and Y 6 are each independently selected from the group consisting of a single bond, N(R 10 ), C(R 11 )(R 12 ), O and S, but both Y 5 and Y 6 are not single bonds,
R8 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 8 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl Boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylamine group is selected from the group consisting of,
상기 R8 내지 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R 8 to R 12 Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C Alkynyl group of 2 ~ C 40 , aryl group of C 6 ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ~ C 60 , alkyloxy group of C 1 ~ C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group consisting of one or more substituents Or unsubstituted, and when substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 화합물은 구체적으로 하기 예시된 구조의 화합물들로 나타낼 수 있으나, 이에 한정되는 것은 아니다.The compound of the present invention may be specifically represented by compounds having the structure illustrated below, but is not limited thereto.
1.예시 구조1.Example structure
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ) Etc.). The detailed synthesis process for the compounds of the present invention will be described in detail in the synthesis examples described later.
2. 유기 전계 발광 소자2. Organic electroluminescent device
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Chemical Formula 1 according to the present invention.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by the formula (1). At this time, the compound may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic material layer includes a compound represented by Formula 1 Can.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 일 예시로 도 1을 참고하면, 예컨대 서로 마주하는 양극(10)과 음극(20), 그리고 상기 양극(10)과 음극(20) 사이에 위치하는 유기층(30)을 포함한다. 여기서, 상기 유기층(30)은 정공 수송층(31), 발광층(32) 및 전자 수송층(34)을 포함할 수 있다. 또한, 상기 정공 수송층(31)과 발광층(32) 사이에는 정공 수송 보조층(33)을 포함할 수 있으며, 상기 전자 수송층(34)과 발광층(32) 사이에는 전자 수송 보조층(35)을 포함할 수 있다.The structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, the positive electrode 10 and the negative electrode 20 facing each other, and the positive electrode 10 and the negative electrode ( 20) includes an organic layer 30 located between. Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32 and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
본 발명의 다른 예시로 도 2를 참고하면, 상기 유기층(30)은 정공 수송층(31)과 양극(10)사이에 정공 주입층(37)을 더 포함할 수 있으며, 전자 수송층(34)과 음극(20)사이에는 전자 주입층(36)을 추가로 더 포함할 수 있다.Referring to Figure 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode Between 20, the electron injection layer 36 may be further included.
본 발명에서 상기 정공 수송층(31)과 양극(10) 사이에 적층되는 정공 주입층(37)은 양극으로 사용되는 ITO와, 정공 수송층(31)으로 사용되는 유기물질 사이의 계면 특성을 개선할 뿐만 아니라 그 표면이 평탄하지 않은 ITO의 상부에 도포되어 ITO의 표면을 부드럽게 만들어주는 기능을 하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, 아민 화합물을 사용할 수 있으나 이에 한정되는 것은 아니다.In the present invention, the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 improves the interfacial properties between ITO used as the anode and the organic material used as the hole transport layer 31. In addition, it is a layer that functions to make the surface of ITO smooth by being applied to the top of ITO where the surface is not flat, and can be used without particular limitation as long as it is commonly used in the art, for example, an amine compound can be used. It is not limited to this.
또한, 상기 전자 주입층(36)은 전자 수송층(34)의 상부에 적층되어 음극으로부터의 전자 주입을 용이하게 해주어 궁극적으로 전력효율을 개선시키는 기능을 수행하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, LiF, Liq, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.In addition, the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate electron injection from the cathode to ultimately improve power efficiency, and is commonly used in the art. If it can be used can be used without particular limitation, for example, LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
또한, 상기 정공 수송층(31)과 발광층(32) 사이에 정공 수송 보조층(33)을 더 포함할 수 있다. 상기 정공 수송 보조층(33)은 발광층(32)에 정공을 수송하는 역할을 하면서 유기층(30)의 두께를 조정하는 역할을 할 수 있다. 상기 정공 수송 보조층(33)은 정공 수송 물질을 포함할 수 있고, 정공 수송층(31)과 동일한 물질로 만들어질 수 있다.In addition, a hole transport auxiliary layer 33 may be further included between the hole transport layer 31 and the light emitting layer 32. The hole transport auxiliary layer 33 may serve to transport holes to the light emitting layer 32 while adjusting the thickness of the organic layer 30. The hole transport auxiliary layer 33 may include a hole transport material, and may be made of the same material as the hole transport layer 31.
또한, 상기 전자 수송층 (34)과 발광층(32) 사이에 전자 수송 보조층(35)을 더 포함할 수 있다. 상기 발광층(32)으로 유기 발광 소자 내에서 이온화 포텐셜 레벨을 타고 이동하는 정공이 전자 수송 보조층(35)의 높은 에너지 장벽에 막혀 전자 수송층(34)으로 확산, 또는 이동하지 못해, 결과적으로 정공을 발광층(32)에 제한시키는 기능을 한다. 이렇게 정공을 발광층(32)에 제한시키는 기능은 환원에 의해 전자를 이동시키는 전자 수송층(34)으로 정공이 확산되는 것을 막아, 산화에 의한 비가역적 분해반응을 통한 수명저하 현상을 억제하여, 유기 발광 소자의 수명 개선에 기여할 수 있다.In addition, an electron transport auxiliary layer 35 may be further included between the electron transport layer 34 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the electron transport auxiliary layer 35 and do not diffuse or move to the electron transport layer 34, resulting in holes. It functions to limit the light emitting layer 32. The function of limiting holes to the light-emitting layer 32 prevents holes from being diffused into the electron transport layer 34 that transfers electrons by reduction, thereby suppressing a decrease in lifespan through irreversible decomposition reaction due to oxidation, and organic light emission. It can contribute to improving the life of the device.
본 발명의 화합물은 비스디벤조모이어티(Bis-Dibenzomoiety)가 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)와 결합되어, 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있고 녹색인광호스트 및 전자수송층에 적용 시 저전압, 고효율, 장수명의 특성을 나타낼 수 있다.In the compound of the present invention, Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.). , Since the entire molecule has a bipolar characteristic, it can increase the bonding force between holes and electrons, and exhibit low voltage, high efficiency, and long life characteristics when applied to a green phosphorescent host and an electron transport layer.
이로 인해, 본 발명의 대표 청구 구조인 화학식 1로 표시되는 화합물은 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 유기물층인 정공 주입층(37), 정공 수송층(31), 발광층(32), 전자 수송층(34) 및 전자 주입층(36) 중 어느 하나의 재료로 사용될 수 있다. 바람직하게는 전자 수송층(34) 및 전자 보조 수송층(35) 재료로 사용될 수 있다.For this reason, since the compound represented by Chemical Formula 1, which is the representative claim structure of the present invention, has excellent light emission properties, the hole injection layer 37, the hole transport layer 31, the light emitting layer 32, and the electron as the organic material layer of the organic electroluminescent device It can be used as a material of any one of the transport layer 34 and the electron injection layer 36. Preferably, it can be used as the material for the electron transport layer 34 and the electron auxiliary transport layer 35.
또한, 본 발명에서 상기 유기 전계 발광 소자는 상기한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층을 추가로 포함할 수 있다.In addition, in the present invention, the organic electroluminescent device may include an anode, one or more organic material layers, and a cathode sequentially stacked as described above, and may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 전자 수송 보조층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention is a material and method known in the art, except that at least one (eg, electron transport auxiliary layer) of the organic material layer is formed to contain the compound represented by the formula (1) It may be manufactured by forming another organic material layer and an electrode.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet may be used.
또, 양극 물질로는 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있으나, 이에 한정되지는 않는다.In addition, the positive electrode material may be made of a conductor having a high work function to facilitate hole injection, for example, a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy 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 polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
또, 음극 물질로는 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되지는 않는다.Further, the negative electrode material may be made of a conductor having a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, the present invention is not limited by the following examples.
[준비예 1-1][Preparation Example 1-1]
6-chloro-4,4'-bidibenzo[b,d]furan의 합성Synthesis of 6-chloro-4,4'-bidibenzo[b,d]furan
질소 기류 하에서 4-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh3)4 (1.23 g, 1.07 mmol), K2CO3 (14.73 g, 106.56 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 85 %)을 획득하였다.4-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl- under nitrogen stream 1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), K 2 CO 3 (14.73 g, 106.56 mmol) and 1,4-dioxane 200 ml and H 2 O 50 ml was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 368.82 g/mol, 측정치: 368 g/mol)GC-Mass (Theoretical value: 368.82 g/mol, Measurement value: 368 g/mol)
[준비예 1-2][Preparation Example 1-2]
Core-1의 합성Synthesis of Core-1
상기 <준비예 1-1>에서 얻은 화합물 (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl2(dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 90 %)을 획득하였다.The compound obtained in <Preparation Example 1-1> (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl 2 (dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 11 g (yield: 90%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 460.34 g/mol, 측정치: 460 g/mol)GC-Mass (Theoretical value: 460.34 g/mol, Measurement value: 460 g/mol)
[준비예 2-1][Preparation Example 2-1]
7'-chloro-3,4'-bidibenzo[b,d]furan의 합성Synthesis of 7'-chloro-3,4'-bidibenzo[b,d]furan
질소 기류 하에서 6-bromo-3-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh3)4 (1.23 g, 1.07 mmol), K2CO3 (14.73 g, 106.56 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 85 %)을 획득하였다.6-bromo-3-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl- under nitrogen stream 1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), K 2 CO 3 (14.73 g, 106.56 mmol) and 1,4-dioxane 200 ml and H 2 O 50 ml was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 368.82 g/mol, 측정치: 368 g/mol)GC-Mass (Theoretical value: 368.82 g/mol, Measurement value: 368 g/mol)
[준비예 2-2][Preparation Example 2-2]
Core-2의 합성Synthesis of Core-2
상기 <준비예 2-1>에서 얻은 화합물 (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl2(dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 90 %)을 획득하였다.Compound prepared in <Preparation Example 2-1> (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl 2 (dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 11 g (yield: 90%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 460.34 g/mol, 측정치: 460 g/mol)GC-Mass (Theoretical value: 460.34 g/mol, Measurement value: 460 g/mol)
[준비예 3-1][Preparation Example 3-1]
6-chloro-3,3'-bidibenzo[b,d]furan의 합성Synthesis of 6-chloro-3,3'-bidibenzo[b,d]furan
질소 기류 하에서 3-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh3)4 (1.23 g, 1.07 mmol), K2CO3 (14.73 g, 106.56 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 85 %)을 획득하였다.3-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl- under nitrogen stream 1,3,2-dioxaborolane (10.45 g, 35.52 mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), K 2 CO 3 (14.73 g, 106.56 mmol) and 1,4-dioxane 200 ml and H 2 O 50 ml was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 368.82 g/mol, 측정치: 368 g/mol)GC-Mass (Theoretical value: 368.82 g/mol, Measurement value: 368 g/mol)
[준비예 3-2][Preparation Example 3-2]
Core-3의 합성Synthesis of Core-3
상기 <준비예 3-1>에서 얻은 화합물 (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl2(dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 90 %)을 획득하였다.The compound obtained in <Preparation Example 3-1> (10.0 g, 27.11 mmol), bis(pinacolato)diboron (8.26 g, 32.54 mmol), PdCl 2 (dppf) (0.66 g, 0.81 mmol), KOAc (5.32 g, 54.23 mmol), X-Phos (1.29 g, 2.71 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 11 g (yield: 90%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 460.34 g/mol, 측정치: 460 g/mol)GC-Mass (Theoretical value: 460.34 g/mol, Measurement value: 460 g/mol)
[준비예 4-1][Preparation Example 4-1]
6-chloro-4,4'-bidibenzo[b,d]thiophene의 합성Synthesis of 6-chloro-4,4'-bidibenzo[b,d]thiophene
질소 기류 하에서 4-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh3)4 (1.16 g, 1.01 mmol), K2CO3 (13.93 g, 100.81 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 80 %)을 획득하였다.4-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl- under nitrogen stream 1,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh 3 ) 4 (1.16 g, 1.01 mmol), K 2 CO 3 (13.93 g, 100.81 mmol) and 1,4-dioxane 200 ml and H 2 O 50 ml was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 10 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 400.94 g/mol, 측정치: 400 g/mol)GC-Mass (Theoretical value: 400.94 g/mol, Measurement value: 400 g/mol)
[준비예 4-2][Preparation Example 4-2]
Core-4의 합성Synthesis of Core-4
상기 <준비예 4-1>에서 얻은 화합물 (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl2(dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 85 %)을 획득하였다.Compound prepared in <Preparation Example 4-1> (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl 2 (dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 10 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 492.46 g/mol, 측정치: 492 g/mol)GC-Mass (Theoretical value: 492.46 g/mol, Measurement value: 492 g/mol)
[준비예 5-1][Preparation Example 5-1]
6-chloro-1,1'-bidibenzo[b,d]thiophene의 합성Synthesis of 6-chloro-1,1'-bidibenzo[b,d]thiophene
질소 기류 1-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh3)4 (1.16 g, 1.01 mmol), K2CO3 (13.93 g, 100.81 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 80 %)을 획득하였다.Nitrogen stream 1-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-1-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh 3 ) 4 (1.16 g, 1.01 mmol), K 2 CO 3 (13.93 g, 100.81 mmol) and 1,4-dioxane 200 ml and H 2 50 ml of O was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 10 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 400.94 g/mol, 측정치: 400 g/mol)GC-Mass (Theoretical value: 400.94 g/mol, Measurement value: 400 g/mol)
[준비예 5-2][Preparation Example 5-2]
Core-5의 합성Synthesis of Core-5
상기 <준비예 5-1>에서 얻은 화합물 (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl2(dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 85 %)을 획득하였다.Compound prepared in <Preparation Example 5-1> (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl 2 (dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 10 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 492.46 g/mol, 측정치: 492 g/mol)GC-Mass (Theoretical value: 492.46 g/mol, Measurement value: 492 g/mol)
[준비예 6-1][Preparation Example 6-1]
6-chloro-2,2'-bidibenzo[b,d]thiophene의 합성Synthesis of 6-chloro-2,2'-bidibenzo[b,d]thiophene
질소 기류 2-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh3)4 (1.16 g, 1.01 mmol), K2CO3 (13.93 g, 100.81 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 80 %)을 획득하였다.Nitrogen flow 2-bromo-6-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (10.42 g, 33.60 mmol), Pd(PPh 3 ) 4 (1.16 g, 1.01 mmol), K 2 CO 3 (13.93 g, 100.81 mmol) and 1,4-dioxane 200 ml and H 2 50 ml of O was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 10 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 400.94 g/mol, 측정치: 400 g/mol)GC-Mass (Theoretical value: 400.94 g/mol, Measurement value: 400 g/mol)
[준비예 6-2][Preparation Example 6-2]
Core-6의 합성Synthesis of Core-6
상기 <준비예 6-1>에서 얻은 화합물 (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl2(dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 85 %)을 획득하였다.Compound prepared in <Preparation Example 6-1> (10.0 g, 24.94 mmol), bis(pinacolato)diboron (7.60 g, 29.93 mmol), PdCl 2 (dppf) (0.61 g, 0.75 mmol), KOAc (4.90 g, 49.88 mmol), X-Phos (1.19 g, 2.49 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 10 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 492.46 g/mol, 측정치: 492 g/mol)GC-Mass (Theoretical value: 492.46 g/mol, Measurement value: 492 g/mol)
[준비예 7-1][Preparation Example 7-1]
4-chloro-6-(dibenzo[b,d]thiophen-3-yl)dibenzo[b,d]furan의 합성Synthesis of 4-chloro-6-(dibenzo[b,d]thiophen-3-yl)dibenzo[b,d]furan
질소 기류 4-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.02 g, 35.52 mmol), Pd(PPh3)4 (1.23 g, 1.07 mmol), K2CO3 (14.73 g, 106.56 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 80 %)을 획득하였다.Nitrogen flow 4-bromo-6-chlorodibenzo[b,d]furan (10.0 g, 35.52 mmol), 2-(dibenzo[b,d]thiophen-3-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (11.02 g, 35.52 mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), K 2 CO 3 (14.73 g, 106.56 mmol) and 1,4-dioxane 200 ml and H 2 50 ml of O was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 10 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 384.88 g/mol, 측정치: 384 g/mol)GC-Mass (Theoretical value: 384.88 g/mol, Measurement value: 384 g/mol)
[준비예 7-2][Preparation Example 7-2]
Core-7의 합성Synthesis of Core-7
상기 <준비예 7-1>에서 얻은 화합물 (10.0 g, 25.98 mmol), bis(pinacolato)diboron (7.92 g, 31.18 mmol), PdCl2(dppf) (0.64 g, 0.78 mmol), KOAc (5.10 g, 51.96 mmol), X-Phos (1.24 g, 2.60 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 85 %)을 획득하였다.The compound obtained in <Preparation Example 7-1> (10.0 g, 25.98 mmol), bis(pinacolato)diboron (7.92 g, 31.18 mmol), PdCl 2 (dppf) (0.64 g, 0.78 mmol), KOAc (5.10 g, 51.96 mmol), X-Phos (1.24 g, 2.60 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 10 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 476.40 g/mol, 측정치: 476 g/mol)GC-Mass (Theoretical value: 476.40 g/mol, Measurement value: 476 g/mol)
[준비예 8-1][Preparation Example 8-1]
1-(7-chlorodibenzo[b,d]thiophen-4-yl)dibenzo[b,d]furan의 합성Synthesis of 1-(7-chlorodibenzo[b,d]thiophen-4-yl)dibenzo[b,d]furan
질소 기류 6-bromo-3-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.88 g, 33.60 mmol), Pd(PPh3)4 (1.16 g, 1.01 mmol), K2CO3 (13.93 g, 100.81 mmol)와 1,4-dioxane 200 ml 및 H2O 50 ml를 혼합하고 110℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 80 %)을 획득하였다.Nitrogen flow 6-bromo-3-chlorodibenzo[b,d]thiophene (10.0 g, 33.60 mmol), 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (9.88 g, 33.60 mmol), Pd(PPh 3 ) 4 (1.16 g, 1.01 mmol), K 2 CO 3 (13.93 g, 100.81 mmol) and 1,4-dioxane 200 ml and H 2 50 ml of O was mixed and stirred at 110° C. for 4 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 10 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 384.88 g/mol, 측정치: 384 g/mol)GC-Mass (Theoretical value: 384.88 g/mol, Measurement value: 384 g/mol)
[준비예 8-2][Preparation Example 8-2]
Core-8의 합성Synthesis of Core-8
상기 <준비예 8-1>에서 얻은 화합물 (10.0 g, 25.98 mmol), bis(pinacolato)diboron (7.92 g, 31.18 mmol), PdCl2(dppf) (0.64 g, 0.78 mmol), KOAc (5.10 g, 51.96 mmol), X-Phos (1.24 g, 2.60 mmol) 및 1,4-dioxane 200 ml를 혼합하고 110℃에서 8시간 동안 교반하였다. 반응 종결 후 실리카겔 및 셀라이트로 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10 g (yield: 85 %)을 획득하였다.The compound obtained in <Preparation Example 8-1> (10.0 g, 25.98 mmol), bis(pinacolato)diboron (7.92 g, 31.18 mmol), PdCl 2 (dppf) (0.64 g, 0.78 mmol), KOAc (5.10 g, 51.96 mmol), X-Phos (1.24 g, 2.60 mmol) and 1,4-dioxane 200 ml were mixed and stirred at 110° C. for 8 hours. After completion of the reaction, it was filtered with silica gel and celite. After removing the solvent of the filtered organic layer, 10 g (yield: 85%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 476.40 g/mol, 측정치: 476 g/mol)GC-Mass (Theoretical value: 476.40 g/mol, Measurement value: 476 g/mol)
[합성예 1][Synthesis Example 1]
A-10의 합성Synthesis of A-10
질소 기류 하에서 Core-1 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh3)4 (0.75 g, 0.65 mmol), K2CO3 (9.01 g, 65.17 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-1 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh 3 ) 4 (0.75 g, 0.65 mmol), K 2 CO 3 (9.01 g, 65.17 mmol) and 100 ml of 1,4-dioxane and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 655.71 g/mol, 측정치: 655 g/mol)GC-Mass (Theoretical value: 655.71 g/mol, Measurement value: 655 g/mol)
[합성예 2][Synthesis Example 2]
A-22의 합성Synthesis of A-22
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 1 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 671.77 g/mol, 측정치: 671 g/mol)GC-Mass (Theoretical value: 671.77 g/mol, Measurement value: 671 g/mol)
[합성예 3][Synthesis Example 3]
A-4의 합성Synthesis of A-4
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 1, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 654.73 g/mol, 측정치: 654 g/mol)GC-Mass (Theoretical value: 654.73 g/mol, Measurement value: 654 g/mol)
[합성예 4][Synthesis Example 4]
A-41의 합성Synthesis of A-41
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4-,6-bis(dibenzo[b,d]furan- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was performed except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 745.79 g/mol, 측정치: 745 g/mol)GC-Mass (Theoretical value: 745.79 g/mol, Measurement value: 745 g/mol)
[합성예 5][Synthesis Example 5]
A-225의 합성Synthesis of A-225
질소 기류 하에서 Core-2 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh3)4 (0.75 g, 0.65 mmol), K2CO3 (9.01 g, 65.17 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-2 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh 3 ) 4 (0.75 g, 0.65 mmol), K 2 CO 3 (9.01 g, 65.17 mmol) and 100 ml of 1,4-dioxane and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 655.71 g/mol, 측정치: 655 g/mol)GC-Mass (Theoretical value: 655.71 g/mol, Measurement value: 655 g/mol)
[합성예 6][Synthesis Example 6]
A-237의 합성Synthesis of A-237
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 5 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 671.77 g/mol, 측정치: 671 g/mol)GC-Mass (Theoretical value: 671.77 g/mol, Measurement value: 671 g/mol)
[합성예 7][Synthesis Example 7]
A-219의 합성Synthesis of A-219
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 6, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 654.73 g/mol, 측정치: 654 g/mol)GC-Mass (Theoretical value: 654.73 g/mol, Measurement value: 654 g/mol)
[합성예 8][Synthesis Example 8]
A-256의 합성Synthesis of A-256
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4-,6-bis(dibenzo[b,d]furan- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 7 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 745.79 g/mol, 측정치: 745 g/mol)GC-Mass (Theoretical value: 745.79 g/mol, Measurement value: 745 g/mol)
[합성예 9][Synthesis Example 9]
A-612의 합성Synthesis of A-612
질소 기류 하에서 Core-3 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh3)4 (0.75 g, 0.65 mmol), K2CO3 (9.01 g, 65.17 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-3 (10.0 g, 21.72 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.77 g, 21.72 mmol), Pd(PPh 3 ) 4 (0.75 g, 0.65 mmol), K 2 CO 3 (9.01 g, 65.17 mmol) and 100 ml of 1,4-dioxane and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 655.71 g/mol, 측정치: 655 g/mol)GC-Mass (Theoretical value: 655.71 g/mol, Measurement value: 655 g/mol)
[합성예 10][Synthesis Example 10]
A-624의 합성Synthesis of A-624
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 9 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 671.77 g/mol, 측정치: 671 g/mol)GC-Mass (Theoretical value: 671.77 g/mol, Measurement value: 671 g/mol)
[합성예 11][Synthesis Example 11]
A-606의 합성Synthesis of A-606
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 9, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 654.73 g/mol, 측정치: 654 g/mol)GC-Mass (Theoretical value: 654.73 g/mol, Measurement value: 654 g/mol)
[합성예 12][Synthesis Example 12]
A-643의 합성Synthesis of A-643
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 9와 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4-,6-bis(dibenzo[b,d]furan- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 9 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 745.79 g/mol, 측정치: 745 g/mol)GC-Mass (Theoretical value: 745.79 g/mol, Measurement value: 745 g/mol)
[합성예 13][Synthesis Example 13]
B-10의 합성Synthesis of B-10
질소 기류 하에서 Core-4 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh3)4 (0.70 g, 0.61 mmol), K2CO3 (8.42 g, 60.92 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-4 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh 3 ) 4 (0.70 g, 0.61 mmol), K 2 CO 3 (8.42 g, 60.92 mmol) and 1,4-dioxane 100 ml and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 687.84 g/mol, 측정치: 687 g/mol)GC-Mass (Theoretical value: 687.84 g/mol, Measurement value: 687 g/mol)
[합성예 14][Synthesis Example 14]
B-22의 합성Synthesis of B-22
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 13과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 13 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 703.90 g/mol, 측정치: 703 g/mol)GC-Mass (Theoretical value: 703.90 g/mol, Measurement value: 703 g/mol)
[합성예 15][Synthesis Example 15]
B-4의 합성Synthesis of B-4
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 13과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 13, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 686.85 g/mol, 측정치: 686 g/mol)GC-Mass (Theoretical value: 686.85 g/mol, Measurement value: 686 g/mol)
[합성예 16][Synthesis Example 16]
B-41의 합성Synthesis of B-41
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 13과 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4-,6-bis(dibenzo[b,d]furan- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 13 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 777.92 g/mol, 측정치: 777 g/mol)GC-Mass (Theoretical value: 777.92 g/mol, Measurement value: 777 g/mol)
[합성예 17][Synthesis Example 17]
B-268의 합성Synthesis of B-268
질소 기류 하에서 Core-5 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh3)4 (0.70 g, 0.61 mmol), K2CO3 (8.42 g, 60.92 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-5 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh 3 ) 4 (0.70 g, 0.61 mmol), K 2 CO 3 (8.42 g, 60.92 mmol) and 1,4-dioxane 100 ml and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 687.84 g/mol, 측정치: 687 g/mol)GC-Mass (Theoretical value: 687.84 g/mol, Measurement value: 687 g/mol)
[합성예 18][Synthesis Example 18]
B-280의 합성Synthesis of B-280
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 17과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 17 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 703.90 g/mol, 측정치: 703 g/mol)GC-Mass (Theoretical value: 703.90 g/mol, Measurement value: 703 g/mol)
[합성예 19][Synthesis Example 19]
B-262의 합성Synthesis of B-262
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 17과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 17, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 686.85 g/mol, 측정치: 686 g/mol)GC-Mass (Theoretical value: 686.85 g/mol, Measurement value: 686 g/mol)
[합성예 20][Synthesis Example 20]
B-301의 합성Synthesis of B-301
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 17과 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4,6-bis(dibenzo[b,d]thiophen- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 17 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 810.04 g/mol, 측정치: 810 g/mol)GC-Mass (Theoretical value: 810.04 g/mol, Measurement value: 810 g/mol)
[합성예 21][Synthesis Example 21]
B-179의 합성Synthesis of B-179
질소 기류 하에서 Core-6 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh3)4 (0.70 g, 0.61 mmol), K2CO3 (8.42 g, 60.92 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-6 (10.0 g, 20.31 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.27 g, 20.31 mmol), Pd(PPh 3 ) 4 (0.70 g, 0.61 mmol), K 2 CO 3 (8.42 g, 60.92 mmol) and 1,4-dioxane 100 ml and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 687.84 g/mol, 측정치: 687 g/mol)GC-Mass (Theoretical value: 687.84 g/mol, Measurement value: 687 g/mol)
[합성예 22][Synthesis Example 22]
B-194의 합성Synthesis of B-194
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 21과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine, except for using the same procedure as in Synthesis Example 21 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 703.90 g/mol, 측정치: 703 g/mol)GC-Mass (Theoretical value: 703.90 g/mol, Measurement value: 703 g/mol)
[합성예 23][Synthesis Example 23]
B-176의 합성Synthesis of B-176
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 21과 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 21, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 686.85 g/mol, 측정치: 686 g/mol)GC-Mass (Theoretical value: 686.85 g/mol, Measurement value: 686 g/mol)
[합성예 24][Synthesis Example 24]
B-215의 합성Synthesis of B-215
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 21과 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4,6-bis(dibenzo[b,d]thiophen- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 21 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 810.04 g/mol, 측정치: 810 g/mol)GC-Mass (Theoretical value: 810.04 g/mol, Measurement value: 810 g/mol)
[합성예 25][Synthesis Example 25]
C-53의 합성Synthesis of C-53
질소 기류 하에서 Core-7 (10.0 g, 20.99 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.85 g, 20.99 mmol), Pd(PPh3)4 (0.73 g, 0.63mmol), K2CO3 (8.70 g, 62.97 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Under nitrogen stream Core-7 (10.0 g, 20.99 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.85 g, 20.99 mmol), Pd(PPh 3 ) 4 (0.73 g, 0.63 mmol), K 2 CO 3 (8.70 g, 62.97 mmol) and 1,4-dioxane 100 ml and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 671.77 g/mol, 측정치: 671 g/mol)GC-Mass (Theoretical value: 671.77 g/mol, Measurement value: 671 g/mol)
[합성예 26][Synthesis Example 26]
C-65의 합성Synthesis of C-65
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 25와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine except for using the same procedure as in Synthesis Example 25 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 687.84 g/mol, 측정치: 687 g/mol)GC-Mass (Theoretical value: 687.84 g/mol, Measurement value: 687 g/mol)
[합성예 27][Synthesis Example 27]
C-47의 합성Synthesis of C-47
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 25와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 25, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 670.79 g/mol, 측정치: 670 g/mol)GC-Mass (Theoretical value: 670.79 g/mol, Measurement value: 670 g/mol)
[합성예 28][Synthesis Example 28]
C-84의 합성Synthesis of C-84
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 25와 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4,6-bis(dibenzo[b,d]thiophen- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 25 was performed, except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 761.86 g/mol, 측정치: 761 g/mol)GC-Mass (Theoretical value: 761.86 g/mol, Measurement value: 761 g/mol)
[합성예 29][Synthesis Example 29]
D-139의 합성Synthesis of D-139
질소 기류 하에서 Core-8 (10.0 g, 20.99 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.85 g, 20.99 mmol), Pd(PPh3)4 (0.73 g, 0.63mmol), K2CO3 (8.70 g, 62.97 mmol)와 1,4-dioxane 100 ml 및 H2O 25 ml를 혼합하고 100℃에서 4시간 동안 교반하였다. 반응 종결 후 다이클로로메탄 으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.Core-8 (10.0 g, 20.99 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.85 g, 20.99) under nitrogen stream mmol), Pd(PPh 3 ) 4 (0.73 g, 0.63 mmol), K 2 CO 3 (8.70 g, 62.97 mmol) and 1,4-dioxane 100 ml and 25 ml of H 2 O are mixed and 4 hours at 100° C. Stir for a while. After completion of the reaction, extraction was performed with dichloromethane, MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer, 11 g (yield: 80%) of the target compound was obtained using column chromatography.
GC-Mass (이론치: 671.77 g/mol, 측정치: 671 g/mol)GC-Mass (Theoretical value: 671.77 g/mol, Measurement value: 671 g/mol)
[합성예 30][Synthesis Example 30]
D-151의 합성Synthesis of D-151
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine를 사용하는 것을 제외하고는 합성예 29와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.2-chloro-4-(dibenzo[b,d]thiophen-3-yl instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine )-6-phenyl-1,3,5-triazine, except for using the same procedure as in Synthesis Example 29 to obtain the target compound 11 g (yield: 80%).
GC-Mass (이론치: 687.84 g/mol, 측정치: 687 g/mol)GC-Mass (Theoretical value: 687.84 g/mol, Measurement value: 687 g/mol)
[합성예 31][Synthesis Example 31]
D-133의 합성Synthesis of D-133
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole 를 사용하는 것을 제외하고는 합성예 29와 동일한 과정을 수행하여 목적 화합물 11 g (yield: 80 %)을 획득하였다.9-(4-chloro-6-phenyl-1,3,5-triazin instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 11 g (yield: 80%) of the target compound was obtained by performing the same procedure as in Synthesis Example 29, except that -2-yl)-9H-carbazole was used.
GC-Mass (이론치: 670.79 g/mol, 측정치: 670 g/mol)GC-Mass (Theoretical value: 670.79 g/mol, Measurement value: 670 g/mol)
[합성예 32][Synthesis Example 32]
D-170의 합성Synthesis of D-170
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4,6-bis(dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine 를 사용하는 것을 제외하고는 합성예 29와 동일한 과정을 수행하여 목적 화합물 12 g (yield: 80 %)을 획득하였다.2-chloro-4,6-bis(dibenzo[b,d]thiophen- instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine The same procedure as in Synthesis Example 29 was performed except that 3-yl)-1,3,5-triazine was used to obtain 12 g (yield: 80%) of the target compound.
GC-Mass (이론치: 761.86 g/mol, 측정치: 761 g/mol)GC-Mass (Theoretical value: 761.86 g/mol, Measurement value: 761 g/mol)
[실시예][Example]
[실시예 A-1] 녹색 유기 전계 발광 소자의 제조[Example A-1] Preparation of green organic electroluminescent device
합성된 화합물 A-10을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.After the high purity sublimation purification of the synthesized compound A-10 by a commonly known method, a green organic electroluminescent device was prepared as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.The glass substrate coated with ITO (Indium tin oxide) with a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and then the substrate is used for 5 minutes using UV. The substrate was cleaned and transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm)/TCTA (80 nm)/A-10(40nm) + 10 % Ir(ppy)3/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the ITO transparent electrode prepared as above, m-MTDATA (60 nm)/TCTA (80 nm)/A-10 (40 nm) + 10% Ir(ppy)3/BCP (10 nm)/Alq3 (30 nm)/ An organic electroluminescent device was manufactured by stacking in order of LiF (1 nm)/Al (200 nm).
사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP used are as follows.
[실시예 A-2 ~ A-32] 녹색 유기 전계 발광 소자의 제조[Examples A-2 to A-32] Preparation of green organic electroluminescent device
실시예 B-1에서 녹색 발광층 형성시 녹색 발광 물질로 사용된 화합물 A-10 대신 동일하게 수행하여 유기 EL 소자를 제조하였다.When forming the green light emitting layer in Example B-1, an organic EL device was manufactured in the same manner as Compound A-10 used as a green light emitting material.
[비교예 1] 녹색 유기 전계 발광 소자의 제조[Comparative Example 1] Preparation of green organic electroluminescent device
실시예 A-1에서 화합물A-10을 사용하지 않은 것을 제외하고는, 실시예 A-1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was manufactured in the same manner as in Example A-1, except that Compound A-10 was not used in Example A-1.
[평가예 1][Evaluation Example 1]
실시예 A-1 내지 A-32 및 비교예 1에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the organic electroluminescent devices prepared in Examples A-1 to A-32 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. It is shown in.
상기 표1 에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광 재료로 사용한 녹색 유기 전계 발광 소자(실시예 A-1 내지 A-32 에서 각각 제조된 녹색 유기 전계 발광 소자)는, 종래 CBP만을 발광층의 재료로 사용한 녹색 유기 전계 발광 소자(비교예 1의 유기 전계 발광 소자)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1, the green organic electroluminescent devices (green organic electroluminescent devices manufactured in Examples A-1 to A-32, respectively) using the compound according to the present invention as a luminescent material, only CBP of the conventional light emitting layer It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the green organic electroluminescent element used as a material (the organic electroluminescent element of Comparative Example 1).
[실시예 B-1] 유기 EL 소자의 제조[Example B-1] Preparation of organic EL device
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.The glass substrate coated with ITO (Indium tin oxide) with a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning is performed with a solvent such as isopropyl alcohol, acetone or methanol, dried, transferred to a UV ozone cleaner (Power sonic 405, Hwashin Tech), and the substrate is washed for 5 minutes using UV. Then, the substrate was transferred to a vacuum layerer.
상기와 같이 준비된 ITO 투명 전극 위에 DS-205(80 nm)/ NPB(15nm)/ ADN + 5% DS-405(30nm)/ A-10(80nm)/ LiF(1nm)/Al(200nm) 순서로 유기 EL 소자를 제조하였다.DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (30 nm) / A-10 (80 nm) / LiF (1 nm) / Al (200 nm) in the order of ITO transparent electrode prepared as above An organic EL device was produced.
[실시예 B-2 ~ B-32] 유기 EL 소자의 제조[Examples B-2 to B-32] Preparation of organic EL device
실시예 B-1에서 전자 수송층 형성시 전자 수송층 물질로 사용된 화합물 A-10 대신 동일하게 수행하여 유기 EL 소자를 제조하였다.When forming the electron transport layer in Example B-1, an organic EL device was manufactured by performing the same procedure instead of Compound A-10 used as the electron transport layer material.
[비교예 2] 유기 EL 소자의 제작[Comparative Example 2] Fabrication of organic EL device
실시예 B-1에서 전자 수송층 형성시 전자 수송층 물질로 사용된 화합물 A-10 대신 Alq3를 전자수송층 물질로 사용한 것을 제외하고는, 상기 실시예 B-1과 동일한 방법으로 유기 EL 소자를 제조하였다.An organic EL device was manufactured in the same manner as in Example B-1, except that Alq3 was used as the electron transporting layer material instead of Compound A-10 used as the electron transporting layer material when forming the electron transporting layer in Example B-1.
소자 제작에 사용된 DS-205 및 DS-405는 (주)두산 전자 BG의 제품이며, NPB, ADN 및 Alq3의 구조는 하기와 같다.DS-205 and DS-405 used for device fabrication are products of Doosan Electronics BG Co., Ltd., and the structures of NPB, ADN and Alq3 are as follows.
[평가예 2][Evaluation Example 2]
실시예 B-1 내지 B-32 및 비교예 2에서 각각 제조된 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율를 측정하였고, 그 결과를 하기 표 2에 나타내었다.The driving voltage and current efficiency at the current density of 10 mA/cm 2 were measured for the organic EL devices manufactured in Examples B-1 to B-32 and Comparative Example 2, respectively, and the results are shown in Table 2 below.
상기 표2에 나타낸 바와 같이, 본 발명에 따른 화합물을 전자수송층으로 사용한 유기 EL 소자(실시예 B-1 내지 B-32에서 각각 제조된 유기 EL 소자)는, 종래 Alq를 사용한 유기 EL 소자(비교예2의 유기 EL 소자)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2 above, the organic EL devices using the compound according to the present invention as an electron transport layer (organic EL devices manufactured in Examples B-1 to B-32, respectively) are organic EL devices using conventional Alq (comparison) It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the organic EL device of Example 2).
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.
Claims (6)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the formula (1):[화학식 1][Formula 1]
상기 화학식 1 에서,In Chemical Formula 1,X1, 내지 X3은 각각 독립적으로 N 또는 C(R1)이나, 적어도 하나 이상은 N이고,X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,L1 내지 L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 C6~C40의 아릴렌기, 및 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;Ar1은 하기 화학식 2로 표시되는 치환기이고,Ar 1 is a substituent represented by the following formula (2),Ar2는 하기 화학식 3으로 표시되는 치환기이며,Ar 2 is a substituent represented by the following formula (3),Ar3은 C6~C18의 아릴기 또는 핵원자수 5 내지 18개의 헤테로아릴기이고,Ar 3 is a C 6 ~ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms,[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 내지 3에서,In Chemical Formulas 2 to 3,*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,Y1 및 Y2는 각각 독립적으로 O 또는 S이며,Y 1 and Y 2 are each independently O or S,Z1 및 Z2는 각각 독립적으로 단일결합, N(R2), C(R3)(R4), O, S, P(R5) 및 Si(R6)(R7)로 구성된 군에서 선택되나, Z1 및 Z2가 모두 단일결합은 아니고,Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,a 및 b는 각각 독립적으로 0 내지 4의 정수이며a and b are each independently an integer from 0 to 4R1 내지 R7은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며,R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl Boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups condensed ring To form,상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ alkyl group of C 40, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryl of C 60 Oxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 1 ~ C 40 alkyl Silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 When substituted with one or more substituents selected from the group consisting of -C 60 arylsilyl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. - 제1항에 있어서,According to claim 1,상기 Ar1은 하기 A-1 내지 A-10 중 어느 하나로 표시되는 치환기인 것을 특징으로 하는 화합물:Ar 1 is a compound characterized in that it is a substituent represented by any one of the following A-1 to A-10:
상기 A-1 내지 A-10에서, Y1 및 Y2는 제1항의 화학식 1에서 정의된 바와 같다.In A-1 to A-10, Y 1 and Y 2 are as defined in Formula 1 of claim 1. - 제1항에 있어서,According to claim 1,상기 Ar2는 하기 B-1 내지 B-9 중 어느 하나로 표시되는 치환기인 것을 특징으로 하는 화합물:The Ar 2 is a compound characterized in that it is a substituent represented by any one of the following B-1 to B-9:
상기 B-1 내지 B-9에서,In B-1 to B-9,*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,고리 A는 5 내지 6원의 사이클로알킬, 페닐 또는 5 내지 6원의 헤테로아릴이고,Ring A is a 5-6 membered cycloalkyl, phenyl or a 5-6 membered heteroaryl,R2 내지 R4는 제1항의 화학식 1에서 정의된 바와 같고,R 2 to R 4 are as defined in Formula 1 of claim 1,Y3 및 Y4는 각각 독립적으로 O 또는 S이다.Y 3 and Y 4 are each independently O or S. - 제1항에 있어서,According to claim 1,상기 Ar3은 하기 C-1 내지 C-6 중 어느 하나로 표시되는 치환기인 것을 특징으로 하는 화합물:The Ar 3 is a compound characterized in that it is a substituent represented by any one of the following C-1 to C-6:
상기 C-1 내지 C-6에서,In the above C-1 to C-6,*는 결합이 이루어지는 부분이고,* Is the part where the bond is made,Y5 및 Y6은 각각 독립적으로 단일결합, N(R10), C(R11)(R12), O 및 S로 구성된 군에서 선택되나, Y5 및 Y6이 모두 단일결합은 아니고,Y 5 and Y 6 are each independently selected from the group consisting of a single bond, N(R 10 ), C(R 11 )(R 12 ), O and S, but both Y 5 and Y 6 are not single bonds,R8 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며,R 8 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl Boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylamine group is selected from the group consisting of,상기 R8 내지 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R 8 to R 12 Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C Alkynyl group of 2 ~ C 40 , aryl group of C 6 ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ~ C 60 , alkyloxy group of C 1 ~ C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 mono or diarylphosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group consisting of one or more substituents Or unsubstituted, and when substituted with a plurality of substituents, they are the same or different from each other. - (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the organic material layer of the one or more layers comprises a compound represented by the formula (1) of claim 1.
- 제5항에 있어서,The method of claim 5,상기 유기물층은 정공 주입층, 정공 수송층, 정공 수송 보조층, 전자 수송층, 전자 수송 보조층 및 발광층으로 이루어진 군에서 선택되는 하나 이상의 층을 포함하는, 유기 전계 발광 소자.The organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.
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| KR20160028524A (en) * | 2014-05-05 | 2016-03-11 | 메르크 파텐트 게엠베하 | Materials for organic light emitting devices |
| KR20180061074A (en) * | 2016-11-29 | 2018-06-07 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN108191842A (en) * | 2017-12-11 | 2018-06-22 | 中节能万润股份有限公司 | A kind of triazines OLED material, and its preparation method and application |
| KR20180111558A (en) * | 2017-03-30 | 2018-10-11 | 주식회사 엘지화학 | Organic light emitting device |
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| KR20160028524A (en) * | 2014-05-05 | 2016-03-11 | 메르크 파텐트 게엠베하 | Materials for organic light emitting devices |
| KR20180061074A (en) * | 2016-11-29 | 2018-06-07 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| KR20180111558A (en) * | 2017-03-30 | 2018-10-11 | 주식회사 엘지화학 | Organic light emitting device |
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