WO2017069443A1 - Organic compound and organic electroluminescent element comprising same - Google Patents
Organic compound and organic electroluminescent element comprising same Download PDFInfo
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- WO2017069443A1 WO2017069443A1 PCT/KR2016/011335 KR2016011335W WO2017069443A1 WO 2017069443 A1 WO2017069443 A1 WO 2017069443A1 KR 2016011335 W KR2016011335 W KR 2016011335W WO 2017069443 A1 WO2017069443 A1 WO 2017069443A1
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- Prior art keywords
- group
- aryl
- compound
- alkyl
- organic
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 239000012044 organic layer Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 88
- 239000010410 layer Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- -1 alkyl boron Chemical compound 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 82
- 238000003786 synthesis reaction Methods 0.000 description 82
- 238000002360 preparation method Methods 0.000 description 44
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 37
- 239000000463 material Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- MMAIMCOMSPMTKJ-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2C=C(C=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MMAIMCOMSPMTKJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- 235000010290 biphenyl Nutrition 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- CTAHMZVXASKGMT-UHFFFAOYSA-N 18-chloro-21,21-dimethylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound ClC1=CC=2C(C3=C(C4=CC=CC=C4C=4C=CC=CC3=4)C=2C=C1)(C)C CTAHMZVXASKGMT-UHFFFAOYSA-N 0.000 description 3
- CRJXXAZXBFZRRV-UHFFFAOYSA-N 2-(5-chloro-2-phenanthren-9-ylphenyl)propan-2-ol Chemical compound ClC=1C=CC(=C(C=1)C(C)(C)O)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1 CRJXXAZXBFZRRV-UHFFFAOYSA-N 0.000 description 3
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- PZALSSAZMCAIIY-UHFFFAOYSA-N 21,21-dimethyl-18-(2-nitrophenyl)pentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound CC1(C=2C=C(C=CC=2C=2C3=CC=CC=C3C=3C=CC=CC=3C=21)C1=C(C=CC=C1)[N+](=O)[O-])C PZALSSAZMCAIIY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
- BAPXNJHZBPEAMA-UHFFFAOYSA-N (5-chloro-2-phenanthren-9-ylphenyl)-diphenylmethanol Chemical compound ClC=1C=CC(=C(C=1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1)C=1C2=CC=CC=C2C=2C=CC=CC=2C=1 BAPXNJHZBPEAMA-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- CZRMKGYSAXYEDF-UHFFFAOYSA-N 18-chloro-21,21-diphenylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound ClC1=CC=2C(C3=C(C4=CC=CC=C4C=4C=CC=CC3=4)C=2C=C1)(C1=CC=CC=C1)C1=CC=CC=C1 CZRMKGYSAXYEDF-UHFFFAOYSA-N 0.000 description 2
- OJTHNYLBXCFYAM-UHFFFAOYSA-N 2-(21,21-dimethyl-18-pentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C(C=3C(=CC=CC=3)C=3C4=CC=CC=3)=C4C(C)(C)C2=C1 OJTHNYLBXCFYAM-UHFFFAOYSA-N 0.000 description 2
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- JTIQNZDSVVBWHR-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)phenyl]-2,6-diphenylpyrimidine Chemical compound ClC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 JTIQNZDSVVBWHR-UHFFFAOYSA-N 0.000 description 2
- MINMDCMSHDBHKG-UHFFFAOYSA-N 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(=C(S1)C)N=C1N1CCOCC1 MINMDCMSHDBHKG-UHFFFAOYSA-N 0.000 description 2
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 2
- 229940127007 Compound 39 Drugs 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
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- 235000019270 ammonium chloride Nutrition 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
- 238000000576 coating method Methods 0.000 description 2
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 230000008022 sublimation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- 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 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-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
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- VERXEWMTFFQXCY-UHFFFAOYSA-N 18-(2-nitrophenyl)-21,21-diphenylpentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15(20),16,18-decaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=2C(C3=C(C4=CC=CC=C4C=4C=CC=CC3=4)C=2C=C1)(C1=CC=CC=C1)C1=CC=CC=C1 VERXEWMTFFQXCY-UHFFFAOYSA-N 0.000 description 1
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- XOJXLAMKKYFLAH-UHFFFAOYSA-N 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound BrC1=NN2C(C(=CC(=C2)C2=CC=CC=C2)C2=CC=CC=C2)=N1 XOJXLAMKKYFLAH-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- 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
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- 229910052727 yttrium Inorganic materials 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Definitions
- the present invention relates to a novel organic compound 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, they shine.
- the material included in 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, and the like according to its function.
- the light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
- a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and 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.
- anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
- a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
- an object of the present invention is to provide an organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
- Another object of the present invention is to provide an organic electroluminescent device including the organic compound and improved driving voltage and luminous efficiency.
- the present invention provides a compound represented by the following formula (1) or (2).
- Ar 1 is a C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy 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 , is selected from the group consisting of C 6 ⁇ C 60 aryl group of boron, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ C 60 aryl group of an amine of,
- R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ group C 60 aryl silyl group, C 1 ⁇ alkyl boron C 40 of, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C of It is selected from the group consisting of 6 ⁇ C 60 arylamine group,
- R 4 and R 5 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ group C 60 aryl silyl group, C 1 ⁇ alkyl boron C 40 of, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C of 6 to C 60 arylamine group, or combine with each other to form a condensed ring,
- the arylphosphine group, the arylphosphine oxide group, and the arylamine group are each independently deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocyclo Alkyl group, C 6 ⁇ C 60 Aryl group, Nuclear 5 to 60 heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C aryl silyl group of 60, C 1
- a to c are each an integer of 1 to 4.
- the present invention also provides an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by Formula 1 or 2 above.
- an organic electroluminescent device comprising any one of compounds, or both.
- Compound represented by the formula (1) of the present invention is a compound having a p-character enhanced phenanthro indenocarbazole core, when applied to the host material of the light emitting layer included in the organic material layer of the organic electroluminescent device, electrons and holes
- the luminous efficiency of the organic EL device can be increased by improving the luminous efficiency, and the lifespan of the organic EL device can be improved.
- the organic compound of the present invention is a compound having various substituents introduced into a phenanthroindenocarbazole core, and is represented by Chemical Formula 1 or 2.
- the compound represented by Formula 1 or 2 of the present invention is an aryl group unsubstituted or substituted with nitrogen (N) of a phenanthroindenocarbazole core, or a substituted or unsubstituted heteroaryl group (eg
- an electron withdrawal group (EWG) having high electron absorption such as a triazine group, a pyridine group, a trizolopyridine group, etc. is introduced, and the whole molecule has a bipolar characteristic, so that it is applied to the organic layer of the organic EL device. When applied, the binding force between holes and electrons can be increased.
- the compound represented by the formula (1) or (2) of the present invention is an alkyl group (for example, dimethyl), or an aryl group (for example, diphenyl) in the carbon (C) of the phenanthroindenocarbazole core Has a high triplet energy because is introduced to enhance steric hindrance. Therefore, when the compound represented by Chemical Formula 1 or 2 of the present invention is applied to the organic material layer of the organic EL device, the exciton generated in the organic material layer (specifically, the light emitting layer) is diffused into another adjacent organic material layer (specifically, the electron transport layer or the hole transport layer). Can be prevented.
- the compound represented by the formula (1) or (2) of the present invention has a glass transition temperature (Tg) and a decomposition temperature TM It has high thermal stability and has uniform morphology. Therefore, when the compound represented by Formula 1 or 2 of the present invention is applied to the organic material layer of the organic EL device, low voltage driving is possible, thereby improving the life of the organic EL device.
- Tg glass transition temperature
- TM decomposition temperature
- Ar 1 is selected from the group consisting of C 6 ⁇ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms, wherein, C 6 ⁇ C 60
- the aryl group and the heteroaryl group having 5 to 60 nuclear atoms are each independently substituted with at least one substituent selected from the group consisting of a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms. .
- Ar 1 in the compound represented by Formula 1 or 2 of the present invention is preferably selected from the group consisting of substituents represented by S1 to S48.
- R 1 to R 3 are hydrogen.
- R 4 and R 5 are each independently hydrogen, an alkyl group of C 1 to C 40 (specifically, a methyl group) and an aryl group of C 6 to C 60 ( Specifically, it is preferably selected from the group consisting of phenyl group).
- Such compounds represented by Formula 1 or 2 of the present invention may be embodied by the following Compounds 1 to 116, but is not limited thereto.
- the method for synthesizing the core of the compound represented by the general formula (1) or (2) of the present invention is not particularly limited, but, for example, can be synthesized by the following scheme (I) or (II).
- alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
- Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
- Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples thereof 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, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 6 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 present invention provides an organic electroluminescent device comprising the compound represented by Formula 1 or 2.
- the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1) or (2). In this case, the compound may be included alone or in a mixture 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 auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 or 2 above. It may include a compound. Specifically, the organic material layer including the compound represented by Chemical Formula 1 or 2 is preferably a light emitting layer.
- the light emitting layer may include a host, wherein the host includes a compound represented by Formula 1 or 2 alone or another compound together with a compound represented by Formula 1 or 2 as a host.
- the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer, and a cathode are sequentially stacked.
- an electron injection layer may be further stacked on the electron transport layer.
- an insulating layer or an adhesive layer may be further stacked on an interface between the electrode (cathode or anode) and the organic material layer.
- the organic electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 or 2.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.
- the anode material is not particularly limited, but may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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 and the like can be used.
- a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb
- Conductive polymers such as polythiophene, poly (3-methylthi
- the negative electrode material is not particularly limited, but may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
- reaction mixture was cooled to room temperature, and 300 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure and purified by silica gel column chromatography to obtain 25.9 g (yield 70%) of the title compound.
- reaction mixture was cooled to room temperature and 300 mL of an ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with EA 500 mL and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 2.5 g (yield 38%) of the title compound.
- a target compound 4.2 g (yield 45%) was obtained in the same manner as in Synthesis Example 6, except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
- Preparation Example 2 Instead of Core 1 and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine obtained in Preparation Example 1
- the same procedure as in [Synthesis Example 7] was carried out except that Core 2 and 4- (4'-chloro- [1,1'-biphenyl] -3-yl) -2,6-diphenylpyrimidine obtained in 4.9 g (53% yield) of compound were obtained.
- a target compound 3.3 g (yield 45%) was obtained in the same manner as in [Synthesis Example 9], except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
- a target compound of 4.2 g (yield 38%) was obtained in the same manner as in Synthesis Example 4, except that Core 4 obtained in Preparation Example 4 was used instead of Core 1 obtained in Preparation Example 1.
- a target compound 3.0 g (yield 46%) was obtained in the same manner as in [Synthesis Example 5], except that Core 4 obtained in [Preparation Example 4] was used instead of Core 1 obtained in [Preparation Example 1].
- ITO Indium tin oxide
- distilled water glass substrate coated with a thin film of 1500 ⁇ thickness After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), washed with UV for 5 minutes and coated with a vacuum evaporator The substrate was transferred.
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / 90% of compound 1, 5, 9, 13, 27, 31, 39, 43, 57, 59, 74, on the prepared ITO transparent glass substrate (electrode) Green organic by stacking in order of 80, 85, 94, 98 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) An electroluminescent device was produced.
- a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a light-emitting host material.
- Example 1 Compound 1 4.3 458 55.0
- Example 2 Compound 5 3.9 459 52.5
- Example 3 Compound 9 4.8 458 58.5
- Example 4 Compound 13 3.8 459 57.3
- Example 5 Compound 27 4.2 459 56.8
- Example 6 Compound 31 4.2 457 51.0
- Example 7 Compound 39 3.9 458 59.1
- Example 8 Compound 43 4.5 459 60.2
- Example 9 Compound 57 4.2 458 55.4
- Example 10 Compound 59 3.9 457 57.5
- Example 11 Compound 74 3.8 459 58.0
- Example 12 Compound 80 4.2 458 59.0
- Example 13 Compound 85 4.5 458 52.7
- Example 14 Compound 94 4.0 459 58.3
- Example 15 Compound 98 3.8 458 57.2 Comparative Example 1 CBP 5.2 459 44.2
- ITO Indium tin oxide
- distilled water glass substrate coated with a thin film of 1500 ⁇ thickness After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed with UV for 5 minutes and vacuum evaporator The glass substrate coated with was transferred.
- a solvent such as isopropyl alcohol, acetone, methanol
- M-MTDATA 60 nm) / TCTA (80 nm) / 90% of compound 5, 7, 9, 20, 49, 55, 94, 100, 109, 110, 112 + on the prepared ITO transparent glass substrate (electrode) 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate a red organic electroluminescent device. It was.
- the structures of m-MTDATA, TCTA and BCP used are as described above, and the structure of (piq) 2 Ir (acac) is as follows.
- a red organic electroluminescent device was manufactured in the same manner as in Example 16, except that CBP was used instead of Compound 5 as a light emitting host material when forming the emission layer.
- the structure of CBP used is as above.
- Example 16 Compound 5 4.5 519 18.5
- Example 17 Compound 7 4.2 519 17.9
- Example 18 Compound 9 4.0 518 18.8
- Example 19 Compound 20 3.8 519 19.2
- Example 20 Compound 49 4.1 518 20.0
- Example 21 Compound 55 4.5 520 18.0
- Example 22 Compound 94 4.0 518 17.2
- Example 23 Compound 100 3.8 519 19.2
- Example 24 Compound 109 3.9 520 18.5
- Example 25 Compound 110 3.9 519 18.2
- Example 26 Compound 112 4.3 518 19.4 Comparative Example 2 CBP 5.4 520 14.5
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Abstract
The present invention relates to an organic compound and an organic electroluminescent element comprising same. The organic compound according to the present invention can increase the luminous efficiency, driving voltage, lifespan, and the like of an organic electroluminescent element when used in an organic layer of the organic electroluminescent element.
Description
본 발명은 신규한 유기 화합물 및 이를 포함한 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 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. 상기 유기물층에 포함되는 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, they shine. The material included in 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, and the like according to its function.
상기 발광 물질은 발광색에 따라 청색, 녹색, 적색의 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색의 발광 물질로 구분될 수 있다. 또한 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여 발광 물질로서 호스트/도판트 계를 사용할 수 있다.The light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color. In addition, a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때 인광 도판트는 이론적으로 형광 도판트에 비해 최대 4배의 발광 효율을 향상시킬 수 있기 때문에 인광 도판트뿐만 아니라 인광 호스트에 대한 연구가 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. In this case, since phosphorescent dopants can theoretically improve luminous efficiency up to 4 times compared to fluorescent dopants, studies on phosphorescent dopants as well as phosphorescent hosts are being conducted.
현재 발광층에 사용되는 형광 도판트/호스트 물질로는 안트라센 유도체들이 알려져 있다. 또한 발광층에 사용되는 인광 도판트 물질로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등의 Ir을 포함하는 금속 착체 화합물이 알려져 있고, 인광 호스트 물질로는 4,4-dicarbazolybiphenyl(CBP)가 알려져 있다.At present, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. In addition, as a phosphorescent dopant material used in the light emitting layer, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
그러나 기존의 재료들은 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있으며, 발광 특성 측면에서도 여전히 개선이 필요하다.However, existing materials have low glass transition temperature and poor thermal stability, and thus are not satisfactory in terms of lifespan in an organic EL device, and still need improvement in terms of light emission characteristics.
[선행기술문헌][Preceding technical literature]
[특허문헌][Patent Documents]
대한민국 공개특허공보 제2008-0038957호Republic of Korea Patent Application Publication No. 2008-0038957
상기한 문제점을 해결하기 위해 본 발명은 유리전이온도가 높고, 열적 안정성이 우수하며, 정공과 전자의 결합력을 향상시킬 수 있는 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide an organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
또 본 발명은 상기 유기 화합물을 포함하여 구동전압 및 발광효율이 향상된 유기 전계 발광 소자를 제공하는 것도 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the organic compound and improved driving voltage and luminous efficiency.
상기한 목적을 달성하기 위해 본 발명은, 하기 화학식 1 또는 2로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1) or (2).
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 또는 2에서,In Chemical Formula 1 or 2,
Ar1은 C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 is a C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group , C 1 ~ C 40 Alkyloxy 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 , is selected from the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,
R1 내지 R3은 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ group C 60 aryl silyl group, C 1 ~ alkyl boron C 40 of, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C of It is selected from the group consisting of 6 ~ C 60 arylamine group,
R4 및 R5는 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 이들이 서로 결합하여 축합 고리를 형성하며,R 4 and R 5 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ group C 60 aryl silyl group, C 1 ~ alkyl boron C 40 of, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C of 6 to C 60 arylamine group, or combine with each other to form a condensed ring,
상기 Ar1 및 R1 내지 R5의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며,An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group of Ar 1 and R 1 to R 5 , The arylphosphine group, the arylphosphine oxide group, and the arylamine group are each independently deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocyclo Alkyl group, C 6 ~ C 60 Aryl group, Nuclear 5 to 60 heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine of C 60 Is substituted or unsubstituted with one or more substituents selected from the group consisting of a pin oxide group and a C 6 ~ C 60 arylamine group,
a 내지 c는 각각 1 내지 4의 정수이다.a to c are each an integer of 1 to 4;
또한 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나가 상기 화학식 1 또는 2로 표시되는 화합물 중 어느 하나의 화합물, 또는 이들 모두를 포함하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by Formula 1 or 2 above. Provided are an organic electroluminescent device comprising any one of compounds, or both.
본 발명의 화학식 1로 표시되는 화합물은 p-character가 강화된 페난트로 인데노카바졸 코어를 가지는 화합물로서, 이를 유기 전계 발광 소자의 유기물층에 포함되는 발광층의 호스트 재료로 적용할 경우, 전자와 정공의 전달이 원활해져 유기 전계 발광 소자의 발광효율이 증대되며, 저전압 구동이 가능하여 유기 전계 발광 소자의 수명도 향상시킬 수 있다.Compound represented by the formula (1) of the present invention is a compound having a p-character enhanced phenanthro indenocarbazole core, when applied to the host material of the light emitting layer included in the organic material layer of the organic electroluminescent device, electrons and holes In this case, the luminous efficiency of the organic EL device can be increased by improving the luminous efficiency, and the lifespan of the organic EL device can be improved.
이하 본 발명을 설명한다.Hereinafter, the present invention will be described.
본 발명의 유기 화합물은 페난트로 인데노카바졸(phenanthroindenocarbazole) 코어에 다양한 치환기가 도입된 화합물로, 상기 화학식 1 또는 2로 표시된다.The organic compound of the present invention is a compound having various substituents introduced into a phenanthroindenocarbazole core, and is represented by Chemical Formula 1 or 2.
구체적으로, 본 발명의 화학식 1 또는 2로 표시되는 화합물은 페난트로 인데노카바졸(phenanthroindenocarbazole) 코어의 질소(N)에 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기(예를 들어, 트리아진기, 피리딘기, 트라이졸로피리딘기 등)와 같은 전자 흡수성이 큰 전자 끌개기(EWG)가 도입되어 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 이를 유기 전계 발광 소자의 유기물층에 적용할 경우 정공과 전자의 결합력을 높일 수 있다.Specifically, the compound represented by Formula 1 or 2 of the present invention is an aryl group unsubstituted or substituted with nitrogen (N) of a phenanthroindenocarbazole core, or a substituted or unsubstituted heteroaryl group (eg For example, an electron withdrawal group (EWG) having high electron absorption such as a triazine group, a pyridine group, a trizolopyridine group, etc. is introduced, and the whole molecule has a bipolar characteristic, so that it is applied to the organic layer of the organic EL device. When applied, the binding force between holes and electrons can be increased.
또한, 본 발명의 화학식 1 또는 2로 표시되는 화합물은 페난트로 인데노카바졸(phenanthroindenocarbazole) 코어의 탄소(C)에 알킬기(예를 들어, 디메틸), 또는 아릴기(예를 들어, 디페닐)가 도입되어 steric hindrance가 강화되기 때문에 높은 삼중항 에너지를 갖는다. 따라서 본 발명의 화학식 1 또는 2로 표시되는 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우 유기물층(구체적으로, 발광층)에서 생성된 엑시톤이 인접한 다른 유기물층(구체적으로, 전자수송층 또는 정공수송층)으로 확산되는 것을 방지할 수 있다.In addition, the compound represented by the formula (1) or (2) of the present invention is an alkyl group (for example, dimethyl), or an aryl group (for example, diphenyl) in the carbon (C) of the phenanthroindenocarbazole core Has a high triplet energy because is introduced to enhance steric hindrance. Therefore, when the compound represented by Chemical Formula 1 or 2 of the present invention is applied to the organic material layer of the organic EL device, the exciton generated in the organic material layer (specifically, the light emitting layer) is diffused into another adjacent organic material layer (specifically, the electron transport layer or the hole transport layer). Can be prevented.
또, 본 발명의 화학식 1 또는 2로 표시되는 화합물은 유리전이 온도(Tg) 및 분해 온도TM가 높아 열적 안정성이 우수하며, 균일한 morphology를 가진다. 따라서 본 발명의 화학식 1 또는 2로 표시되는 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우 저전압 구동이 가능하며, 이로 인해 유기 전계 발광 소자의 수명을 향상시킬 수 있다.In addition, the compound represented by the formula (1) or (2) of the present invention has a glass transition temperature (Tg) and a decomposition temperature TM It has high thermal stability and has uniform morphology. Therefore, when the compound represented by Formula 1 or 2 of the present invention is applied to the organic material layer of the organic EL device, low voltage driving is possible, thereby improving the life of the organic EL device.
이러한 본 발명의 화학식 1 또는 2로 표시되는 화합물은, Ar1이 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고, 이때, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기는 각각 독립적으로, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되는 것이 바람직하다.Such a compound represented by the formula (1) or (2) of the present invention, Ar 1 is selected from the group consisting of C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms, wherein, C 6 ~ C 60 The aryl group and the heteroaryl group having 5 to 60 nuclear atoms are each independently substituted with at least one substituent selected from the group consisting of a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms. .
구체적으로, 본 발명의 화학식 1 또는 2로 표시되는 화합물에서 Ar1은 하기 S1 내지 S48로 표시되는 치환체로 이루어진 군에서 선택되는 것이 바람직하다.Specifically, Ar 1 in the compound represented by Formula 1 or 2 of the present invention is preferably selected from the group consisting of substituents represented by S1 to S48.
또한, 본 발명의 화학식 1 또는 2로 표시되는 화합물은, R1 내지 R3가 모두 수소인 것이 바람직하다.In addition, in the compound represented by the general formula (1) or (2) of the present invention, it is preferable that all of R 1 to R 3 are hydrogen.
또, 본 발명의 화학식 1 또는 2로 표시되는 화합물은, R4 및 R5가 각각 독립적으로, 수소, C1~C40의 알킬기(구체적으로, 메틸기) 및 C6~C60의 아릴기(구체적으로, 페닐기)로 이루어진 군에서 선택되는 것이 바람직하다.In addition, in the compound represented by the formula (1) or (2) of the present invention, R 4 and R 5 are each independently hydrogen, an alkyl group of C 1 to C 40 (specifically, a methyl group) and an aryl group of C 6 to C 60 ( Specifically, it is preferably selected from the group consisting of phenyl group).
이러한 본 발명의 화학식 1 또는 2로 표시되는 화합물은 하기 화합물 1 내지 116로 구체화될 수 있으나, 이들로 한정되는 것은 아니다.Such compounds represented by Formula 1 or 2 of the present invention may be embodied by the following Compounds 1 to 116, but is not limited thereto.
본 발명의 화학식 1 또는 2로 표시되는 화합물의 코어(Core)를 합성하는 방법은 특별히 한정되지 않으나, 일례로, 다음의 반응식 I 또는 II에 의해 합성할 수 있다.The method for synthesizing the core of the compound represented by the general formula (1) or (2) of the present invention is not particularly limited, but, for example, can be synthesized by the following scheme (I) or (II).
[Core 합성 반응식 I] Core Synthesis Scheme I
[Core 합성 반응식 II] Core Synthesis Scheme II
한편, 본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 아릴은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 헤테로아릴은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이의 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; 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples thereof include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40의 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. 이의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 축합 고리는 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.
유기 abandonment
전계Electric field
발광 소자 Light emitting element
본 발명은 상기 화학식 1 또는 2로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising the compound represented by Formula 1 or 2.
구체적으로, 본 발명의 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1 또는 2로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 포함되거나, 또는 2 이상이 혼합된 상태로 포함될 수 있다.Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1) or (2). In this case, the compound may be included alone or in a mixture of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1 또는 2로 표시되는 화합물을 포함할 수 있다. 구체적으로 상기 화학식 1 또는 2로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.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 auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 or 2 above. It may include a compound. Specifically, the organic material layer including the compound represented by Chemical Formula 1 or 2 is preferably a light emitting layer.
구체적으로, 상기 발광층은 호스트를 포함할 수 있는데, 이때 호스트로서 상기 화학식 1 또는 2로 표시되는 화합물을 단독으로 포함하거나 상기 화학식 1 또는 2로 표시되는 화합물과 함께 다른 화합물을 호스트로 포함하는 것이다.Specifically, the light emitting layer may include a host, wherein the host includes a compound represented by Formula 1 or 2 alone or another compound together with a compound represented by Formula 1 or 2 as a host.
본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한 상기 전극(음극, 또는 양극)과 유기물층의 계면에 절연층 또는 접착층이 더 적층될 수 있다.The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer, and a cathode are sequentially stacked. In this case, an electron injection layer may be further stacked on the electron transport layer. In addition, an insulating layer or an adhesive layer may be further stacked on an interface between the electrode (cathode or anode) and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1 또는 2로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 제조할 수 있다.The organic electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 or 2.
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 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.
또한, 양극 물질은 특별히 한정되지 않으나, 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 등을 사용할 수 있다.In addition, the anode material is not particularly limited, but may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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 and the like can be used.
또, 음극 물질은 특별히 한정되지 않으나, 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 등을 사용할 수 있다.The negative electrode material is not particularly limited, but may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
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 with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[준비예 1] Core 1의 합성Preparation Example 1 Synthesis of Core 1
<단계 1> methyl 5-chloro-2-(phenanthren-9-yl)benzoate의 합성<Step 1> Synthesis of methyl 5-chloro-2- (phenanthren-9-yl) benzoate
Methyl 2-bromo-5-chlorobenzoate 50 g (0.20 mol)과 phenanthren-9-ylboronic acid 44.5 g (0.20 mol)에 dioxane 1.0 L와 H2O 300 mL를 가하였다. 다음, Pd(PPh3)4 11.6 g (0.01 mol)와 K2CO3 83.1 g (0.60 mol)을 첨가한 후 120 ℃에서 3시간 동안 가열환류하였다. 그 다음, 상온으로 온도를 냉각하고 반응액에 정제수 300 mL를 투입하여 반응을 종결시킨 후 E.A 1.5 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 62.6 g (수율 90%)을 얻었다.To 50 g (0.20 mol) of methyl 2-bromo-5-chlorobenzoate and 44.5 g (0.20 mol) of phenanthren-9-ylboronic acid were added 1.0 L of dioxane and 300 mL of H 2 O. Next, 11.6 g (0.01 mol) of Pd (PPh 3 ) 4 and 83.1 g (0.60 mol) of K 2 CO 3 were added thereto, and the mixture was heated and refluxed at 120 ° C. for 3 hours. Then, the temperature was cooled to room temperature, 300 mL of purified water was added to the reaction solution to terminate the reaction, extracted with EA 1.5 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure and purified by silica gel column chromatography to obtain 62.6 g (yield 90%) of the title compound.
1H-NMR (in CDCl3) : δ 8.77 (d, 1H), 8.72 (d, 1H), 8.05 (d, 1H), 7.88 (m, 1H), 7.66 (m, 4H), 7.56 (s, 1H), 7.49 (m, 2H), 7.40 (d, 1H), 3.36 (s, 3H) 1 H-NMR (in CDCl 3 ): δ 8.77 (d, 1H), 8.72 (d, 1H), 8.05 (d, 1H), 7.88 (m, 1H), 7.66 (m, 4H), 7.56 (s, 1H), 7.49 (m, 2H), 7.40 (d, 1H), 3.36 (s, 3H)
[LCMS] : 346[LCMS]: 346
<단계 2> 2-(5-chloro-2-(phenanthren-9-yl)phenyl)propan-2-ol의 합성<Step 2> Synthesis of 2- (5-chloro-2- (phenanthren-9-yl) phenyl) propan-2-ol
상기 <단계 1>에서 합성된 methyl 5-chloro-2-(phenanthren-9-yl)benzoate 62 g (0.18 mol)에 THF 1.0 L를 가하였다. 다음, 반응액의 온도를 -78 ℃로 낮추고 methylmagnesium bromide 3M in THF solution 149 mL (0.45 mol)를 천천히 첨가한 후 동일 온도에서 1시간 동안 교반하고, 상온에서 24시간 동안 추가로 교반하였다. 그 다음, 반응액에 정제수 500 mL를 투입하여 반응을 종결시킨 후 E.A 1.5 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 52.7 g (수율 85%)을 얻었다.To 62 g (0.18 mol) of methyl 5-chloro-2- (phenanthren-9-yl) benzoate synthesized in <Step 1> was added 1.0 L of THF. Next, the temperature of the reaction solution was lowered to −78 ° C., and 149 mL (0.45 mol) of methylmagnesium bromide 3M in THF solution was slowly added thereto, and then stirred at the same temperature for 1 hour, and further stirred at room temperature for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, extracted with EA 1.5 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 52.7 g (yield 85%) of the title compound.
1H-NMR (in CDCl3) : δ 8.73 (t, 2H), 7.86 (d, 1H), 7.81 (d, 1H), 7.71 (m, 1H), 7.65 (d, 1H), 7.61 (s, 1H), 7.49 (t, 1H), 7.42 (d, 1H), 7.30 (dd, 1H), 7.08 (d, 1H),1.26 (s, 6H) 1 H-NMR (in CDCl 3 ): δ 8.73 (t, 2H), 7.86 (d, 1H), 7.81 (d, 1H), 7.71 (m, 1H), 7.65 (d, 1H), 7.61 (s, 1H), 7.49 (t, 1H), 7.42 (d, 1H), 7.30 (dd, 1H), 7.08 (d, 1H), 1.26 (s, 6H)
[LCMS] : 346[LCMS]: 346
<단계 3> 11-chloro-13,13-dimethyl-13H-indeno[1,2-l]phenanthrene의 합성<Step 3> Synthesis of 11-chloro-13,13-dimethyl-13H-indeno [1,2-l] phenanthrene
상기 <단계 2>에서 합성된 2-(5-chloro-2-(phenanthren-9-yl)phenyl)propan-2-ol 52 g (0.15 mol)에 conc. HCl 5.2 mL와 AcOH 780 mL를 첨가한 후, 100 ℃에서 2시간 동안 가열환류하였다. 다음, 반응액에 정제수 500 mL를 투입하여 반응을 종결한 후, E.A 1.5 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후, 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 29.6 g (수율 60%)을 얻었다.To 52 g (0.15 mol) of 2- (5-chloro-2- (phenanthren-9-yl) phenyl) propan-2-ol synthesized in <Step 2>, conc. After adding 5.2 mL of HCl and 780 mL of AcOH, the mixture was heated to reflux at 100 ° C. for 2 hours. Next, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with EA 1.5 L and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 29.6 g (yield 60%) of the title compound.
1H-NMR (in CDCl3) : δ 8.84 (d, 3H), 8.34 (m, 2H), 7.74 (m, 4H), 7.57 (s, 1H), 7.45 (d, 1H), 1.79 (s, 6H) 1 H-NMR (in CDCl 3 ): δ 8.84 (d, 3H), 8.34 (m, 2H), 7.74 (m, 4H), 7.57 (s, 1H), 7.45 (d, 1H), 1.79 (s, 6H)
[LCMS] : 328[LCMS]: 328
<단계 4> 2-(13,13-dimethyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane의 합성Step 4 Synthesis of 2- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-11-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
상기 <단계 3>에서 합성된 11-chloro-13,13-dimethyl-13H-indeno[1,2-l]phenanthrene 29.0 g (0.09 mol)과 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 26.9 g (0.11 mol)에 dioxane 600 mL를 가하였다. 다음, Pd(dppf)Cl2 3.6 g (4.4 mmol)와 KOAc 26.0 g (0.26 mol)을 첨가한 후 130 ℃에서 12시간 동안 가열환류하였다. 그 다음, 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 300 mL를 투입하여 반응을 종결시키고, E.A 1.0 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 25.9 g (수율 70%)을 얻었다.29.0 g (0.09 mol) of 11-chloro-13,13-dimethyl-13H-indeno [1,2-l] phenanthrene synthesized in <Step 3> and 4,4,4 ', 4', 5,5, 600 mL of dioxane was added to 26.9 g (0.11 mol) of 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane). Next, 3.6 g (4.4 mmol) of Pd (dppf) Cl 2 and 26.0 g (0.26 mol) of KOAc were added thereto, followed by heating to reflux at 130 ° C. for 12 hours. Then, the reaction mixture was cooled to room temperature, and 300 mL of an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure and purified by silica gel column chromatography to obtain 25.9 g (yield 70%) of the title compound.
1H-NMR (in CDCl3) : δ 8.96 (d, 1H), 8.82 (m, 2H), 8.06 (s, 1H), 7.96 (dd, 1H), 7.70 (m, 4H), 1.81 (s, 6H), 1.41 (s, 12H) 1 H-NMR (in CDCl 3 ): δ 8.96 (d, 1H), 8.82 (m, 2H), 8.06 (s, 1H), 7.96 (dd, 1H), 7.70 (m, 4H), 1.81 (s, 6H), 1.41 (s, 12H)
[LCMS] : 420[LCMS]: 420
<단계 5> 13,13-dimethyl-11-(2-nitrophenyl)-13H-indeno[1,2-l]phenanthrene의 합성Step 5 Synthesis of 13,13-dimethyl-11- (2-nitrophenyl) -13H-indeno [1,2-l] phenanthrene
Methyl 2-bromo-5-chlorobenzoate와 phenanthren-9-ylboronic acid 대신 상기 <단계 4>에서 합성된 2-(13,13-dimethyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane과 1-bromo-2-nitrobenzene을 사용한 것을 제외하고는 [준비예 1]의 <단계 1>과 동일한 과정을 수행하여 목적 화합물 21.0 g (수율 82%)을 얻었다.2- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-11-yl)-synthesized in <Step 4> instead of methyl 2-bromo-5-chlorobenzoate and phenanthren-9-ylboronic acid Except for using 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 1-bromo-2-nitrobenzene, the same procedure as in <Step 1> of [Preparation Example 1] was performed, to obtain the title compound 21.0. g (yield 82%) was obtained.
1H-NMR (in CDCl3) : δ 8.93 (d, 1H), 8.83 (m, 2H), 8.47 (d, 1H), 8.35 (m, 1H), 7.87 (d, 1H), 7.70 (m, 4H), 7.66 (d, 1H), 7.60 (d, 1H), 7.55 (s, 1H), 7.49 (t, 1H), 7.44 (dd, 1H), 1.81 (s, 6H) 1 H-NMR (in CDCl 3 ): δ 8.93 (d, 1H), 8.83 (m, 2H), 8.47 (d, 1H), 8.35 (m, 1H), 7.87 (d, 1H), 7.70 (m, 4H), 7.66 (d, 1H), 7.60 (d, 1H), 7.55 (s, 1H), 7.49 (t, 1H), 7.44 (dd, 1H), 1.81 (s, 6H)
[LCMS] : 415[LCMS]: 415
<단계 6> Core 1의 합성<Step 6> Synthesis of Core 1
상기 <단계 5>에서 합성된 13,13-dimethyl-11-(2-nitrophenyl)-13H-indeno[1,2-l]phenanthrene 21.0 g (0.05 mol)과 P(Ph)3 39.8 g (0.15 mol)에 DCB 300 mL를 가하고, 200 ℃에서 12시간 동안 가열환류하였다. 다음, 반응액에 정제수 500 mL를 투입하여 반응을 종결시킨 후, E.A 1.0 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 7.8 g (수율 40%)을 얻었다.21.0 g (0.05 mol) of 13,13-dimethyl-11- (2-nitrophenyl) -13H-indeno [1,2-l] phenanthrene synthesized in <Step 5> and P (Ph) 3 39.8 g (0.15 mol) ) Was added 300 mL of DCB, and heated to reflux at 200 ° C for 12 hours. Next, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 1.0 L of EA and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 7.8 g (yield 40%) of the title compound.
1H-NMR (in CDCl3) : δ 11.7 (s, 1H), 8.90 (d, 1H), 8.78 (m, 3H), 8.35 (m, 1H), 7.87 (d, 1H), 7.70 (m, 4H), 7.60 (d, 1H), 7.55 (d, 1H), 7.49 (t, 1H), 7.44 (dd, 1H), 1.82 (s, 6H) 1 H-NMR (in CDCl 3 ): δ 11.7 (s, 1H), 8.90 (d, 1H), 8.78 (m, 3H), 8.35 (m, 1H), 7.87 (d, 1H), 7.70 (m, 4H), 7.60 (d, 1H), 7.55 (d, 1H), 7.49 (t, 1H), 7.44 (dd, 1H), 1.82 (s, 6H)
[LCMS] : 383[LCMS]: 383
[준비예 2] Core 2의 합성Preparation Example 2 Synthesis of Core 2
상기 [준비예 1]과 동일한 과정을 수행하여 Core 1의 구조이성질체에 해당하는 목적 화합물 5.4 g (수율 28%)을 얻었다.5.4 g (yield 28%) of the title compound corresponding to the structural isomers of Core 1 was obtained by the same procedure as in [Preparation Example 1].
[LCMS] : 383[LCMS]: 383
[[
준비예Preparation
3] Core 3의 합성 3] Synthesis of Core 3
<단계 1> methyl 5-chloro-2-(phenanthren-9-yl)benzoate의 합성<Step 1> Synthesis of methyl 5-chloro-2- (phenanthren-9-yl) benzoate
상기 [준비예 1]의 <단계 1>과 동일한 과정을 수행하여 목적 화합물 62.6 g (수율 90%)을 얻었다.The same procedure as in <Step 1> of [Preparation Example 1] was performed, to obtain 62.6 g (yield 90%) of the title compound.
[LCMS] : 346[LCMS]: 346
<단계 2> (5-chloro-2-(phenanthren-9-yl)phenyl)diphenylmethanol의 합성<Step 2> Synthesis of (5-chloro-2- (phenanthren-9-yl) phenyl) diphenylmethanol
Meyhlmagnesium bromide 대신 phenylmagnesium bromide를 사용한 것을 제외하고는 상기 [준비예 1]의 <단계 2>와 동일한 과정을 수행하여 목적 화합물 63.6 g (수율 78%)을 얻었다.Except that phenylmagnesium bromide was used instead of meyhlmagnesium bromide, the same procedure as in <Step 2> of [Preparation Example 1] was performed, to obtain 63.6 g (yield 78%) of the title compound.
[LCMS] : 471[LCMS]: 471
<단계 3> 11-chloro-13,13-diphenyl-13H-indeno[1,2-l]phenanthrene의 합성<Step 3> Synthesis of 11-chloro-13,13-diphenyl-13H-indeno [1,2-l] phenanthrene
2-(5-chloro-2-(phenanthren-9-yl)phenyl)propan-2-ol 대신 (5-chloro-2-(phenanthren-9-yl)phenyl)diphenylmethanol을 사용한 것을 제외하고는 상기 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 목적 화합물 49.7 g (수율 82%)을 얻었다.[Preparation of the above except that (5-chloro-2- (phenanthren-9-yl) phenyl) diphenylmethanol was used instead of 2- (5-chloro-2- (phenanthren-9-yl) phenyl) propan-2-ol 49.7 g (yield 82%) of the title compound were obtained in the same manner as <Step 3> of Example 1].
[LCMS] : 452[LCMS]: 452
<단계 4> 2-(13,13-diphenyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane의 합성Step 4 Synthesis of 2- (13,13-diphenyl-13H-indeno [1,2-l] phenanthren-11-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
11-chloro-13,13-dimethyl-13H-indeno[1,2-l]phenanthrene 대신 11-chloro-13,13-diphenyl-13H-indeno[1,2-l]phenanthrene을 사용한 것을 제외하고는 상기 [준비예 1]의 <단계 4>와 동일한 과정을 수행하여 목적 화합물 36.5 g (수율 62%)을 얻었다.Except for using 11-chloro-13,13-diphenyl-13H-indeno [1,2-l] phenanthrene instead of 11-chloro-13,13-dimethyl-13H-indeno [1,2-l] phenanthrene 36.5 g (yield 62%) of the title compound was obtained in the same manner as in <Step 4> of [Preparation Example 1].
[LCMS] : 544[LCMS]: 544
<단계 5> 11-(2-nitrophenyl)-13,13-diphenyl-13H-indeno[1,2-l]phenanthrene의 합성Step 5 Synthesis of 11- (2-nitrophenyl) -13,13-diphenyl-13H-indeno [1,2-l] phenanthrene
2-(13,13-dimethyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 대신 2-(13,13-diphenyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane을 사용한 것을 제외하고는 상기 [준비예 1]의 <단계 5>와 동일한 과정을 수행하여 목적 화합물 32.8 g (수율 92%)을 얻었다.2- (13,13 instead of 2- (13,13-dimethyl-13H-indeno [1,2-l] phenanthren-11-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane [Preparation Example 1] except that the use of -diphenyl-13H-indeno [1,2-l] phenanthren-11-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 32.8 g (yield 92%) of the title compound was obtained in the same manner as in <Step 5>.
[LCMS] : 539[LCMS]: 539
<단계 6> Core 3의 합성<Step 6> Synthesis of Core 3
13,13-dimethyl-11-(2-nitrophenyl)-13H-indeno[1,2-l]phenanthrene 대신 11-(2-nitrophenyl)-13,13-diphenyl-13H-indeno[1,2-l]phenanthrene을 사용한 것을 제외하고는 상기 [준비예 1]의 <단계 6>과 동일한 과정을 수행하여 목적 화합물 13.2 g (수율 44%)을 얻었다.11- (2-nitrophenyl) -13,13-diphenyl-13H-indeno [1,2-l] instead of 13,13-dimethyl-11- (2-nitrophenyl) -13H-indeno [1,2-l] phenanthrene Aside from using phenanthrene, 13.2 g (yield 44%) of the title compound was obtained by the same process as <Step 6> of [Preparation Example 1].
[LCMS] : 507[LCMS]: 507
[준비예 4] Core 4의 합성Preparation Example 4 Synthesis of Core 4
상기 [준비예 3]과 동일한 과정을 수행하여 Core 3의 구조이성질체에 해당하는 목적 화합물 9.8 g (수율 33%)을 얻었다.9.8 g (yield 33%) of the title compound corresponding to the structural isomers of Core 3 was obtained by the same procedure as in [Preparation Example 3].
[LCMS] : 507[LCMS]: 507
[합성예 1] 화합물 1의 합성Synthesis Example 1 Synthesis of Compound 1
[준비예 1]에서 얻어진 Core 1 5.0 g (13.0 mmol)과 2-chloro-4,6-diphenyl-1,3,5-triazine 5.2 g (19.6 mmol)에 DMF 100 mL를 가하였다. 다음, 60% NaH 1.0g (26.1 mmol)을 첨가하고, 상온에서 12시간 동안 교반하였다. 그 다음, 반응액에 정제수 100 mL를 투입하여 반응을 종결시킨 후 E.A 300 mL로 추출하고 증류수로 2회 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 5.0 g (수율 62%)을 얻었다.100 mL of DMF was added to 5.0 g (13.0 mmol) of Core 1 obtained in [Preparation Example 1] and 5.2 g (19.6 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine. Next, 1.0 g (26.1 mmol) of 60% NaH was added, and the mixture was stirred at room temperature for 12 hours. Then, 100 mL of purified water was added to the reaction solution to terminate the reaction, extracted with EA 300 mL, and washed twice with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 5.0 g (yield 62%) of the title compound.
[LCMS] : 614[LCMS]: 614
[합성예 2] 화합물 5의 합성Synthesis Example 2 Synthesis of Compound 5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 3.8 g (수율 54%)을 얻었다.Except for using 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine 3.8 g (yield 54%) of the title compound was obtained in the same manner as in Synthesis Example 1.
[LCMS] : 652[LCMS]: 652
[합성예 3] 화합물 7의 합성Synthesis Example 3 Synthesis of Compound 7
[준비예 1]에서 얻어진 Core 1 6.0 g (15.6 mmol)과 2-chloro-4-phenylquinazoline 4.5 g (18.8 mmol)에 dioxane 100 mL를 가하였다. 다음, Pd(OAc)2 0.18 g (0.78 mmol), P(t-Bu)3 0.63 g (1.6 mmol) 및 K2CO3 6.5 g (46.9 mmol)을 첨가하고, 120 ℃에서 12시간 동안 가열환류하였다. 그 다음, 상온으로 온도를 냉각하고 반응액에 정제수 300 mL를 투입하여 반응을 종결시킨 후 E.A 500 mL로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 5.3 g (수율 55%)을 얻었다.100 mL of dioxane was added to 6.0 g (15.6 mmol) of Core 1 obtained in [Preparation Example 1] and 4.5 g (18.8 mmol) of 2-chloro-4-phenylquinazoline. Next, 0.18 g (0.78 mmol) of Pd (OAc) 2 , 0.63 g (1.6 mmol) of P (t-Bu) 3 and 6.5 g (46.9 mmol) of K 2 CO 3 were added and heated to reflux at 120 ° C. for 12 hours. It was. Then, the temperature was cooled to room temperature, 300 mL of purified water was added to the reaction solution to terminate the reaction, and extracted with EA 500 mL and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 5.3 g (yield 55%) of the title compound.
[LCMS] : 587[LCMS]: 587
[합성예 4] 화합물 9의 합성Synthesis Example 4 Synthesis of Compound 9
2-chloro-4-phenylquinazoline 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.7 g (수율 44%)을 얻었다.4.7 g of the target compound was carried out in the same manner as in [Synthesis Example 3], except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4-phenylquinazoline. (Yield 44%) was obtained.
[LCMS] : 690[LCMS]: 690
[합성예 5] 화합물 13의 합성Synthesis Example 5 Synthesis of Compound 13
2-chloro-4-phenylquinazoline 대신 2-(3-chlorophenyl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 2.9 g (수율 51%)을 얻었다.[Synthesis example 3] except that 2- (3-chlorophenyl) -6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine was used instead of 2-chloro-4-phenylquinazoline The same procedure was followed to obtain 2.9 g (51% yield) of the title compound.
[LCMS] : 728[LCMS]: 728
[합성예 6] 화합물 20의 합성Synthesis Example 6 Synthesis of Compound 20
[준비예 1]에서 얻어진 Core 1 4.5 g (11.7 mmol)과 4-([1,1'-biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine 6.5 g (14.1 mmol)에 dioxane 100 mL를 가하였다. 다음, Pd2(dba)3 0.54 g (0.59 mmol), BINAP 0.73 g (1.2 mmol) 및 Cs2CO3 7.6 g (23.5 mmol)을 첨가한 후 120 ℃에서 12시간 가열환류하였다. 그 다음, 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 300 mL를 투입하여 반응을 종결시킨 후 E.A 500 mL로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 2.5 g (수율 38%)을 얻었다.4.5 g (11.7 mmol) of Core 1 obtained in Preparation Example 1 and 6.5 g (14.1 mmol) of 4-([1,1'-biphenyl] -4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine 100 mL of dioxane was added thereto. Next, 0.54 g (0.59 mmol) of Pd 2 (dba) 3 , 0.73 g (1.2 mmol) of BINAP, and 7.6 g (23.5 mmol) of Cs 2 CO 3 were added thereto, and the mixture was heated and refluxed at 120 ° C. for 12 hours. Then, the reaction mixture was cooled to room temperature and 300 mL of an ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with EA 500 mL and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 2.5 g (yield 38%) of the title compound.
[LCMS] : 765[LCMS]: 765
[합성예 7] 화합물 27의 합성Synthesis Example 7 Synthesis of Compound 27
[준비예 1]에서 얻어진 Core 1 4.0 g (10.4 mmol)과 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine에 dioxane 100 mL를 가하였다. 다음, Pd(OAc)2 0.12 g (0.52 mmol), XPhos 0.50 g (1.0 mmol) 및 Cs2CO3 6.8 g (20.9 mmol)을 첨가하고 120 ℃에서 12시간 동안 가열환류하였다. 그 다음, 상온으로 온도를 냉각하고 반응액에 정제수 300 mL를 투입하여 반응을 종결시킨 후 E.A 500 mL로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 3.1 g (수율 45%)을 얻었다.4.0 g (10.4 mmol) of Core 1 obtained in Preparation Example 1 and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- 100 mL of dioxane was added to triazine. Next, 0.12 g (0.52 mmol) of Pd (OAc) 2 , 0.50 g (1.0 mmol) of XPhos and 6.8 g (20.9 mmol) of Cs 2 CO 3 were added and heated to reflux at 120 ° C. for 12 hours. Then, the temperature was cooled to room temperature, 300 mL of purified water was added to the reaction solution to terminate the reaction, and extracted with EA 500 mL and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 3.1 g (yield 45%) of the title compound.
[LCMS] : 766[LCMS]: 766
[합성예 8] 화합물 31의 합성Synthesis Example 8 Synthesis of Compound 31
2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.6 g (수율 40%)을 얻었다.2- (3'-chloro- [1,1'- instead of 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine Except for using biphenyl] -3-yl) -4,6-diphenylpyrimidine was carried out the same procedure as in Synthesis Example 7 to obtain 4.6 g (yield 40%) of the title compound.
[LCMS] : 765[LCMS]: 765
[합성예 9] 화합물 39의 합성Synthesis Example 9 Synthesis of Compound 39
2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 2.7 g (수율 55%)을 얻었다.4-([1,1'-biphenyl] -4- instead of 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine Except for using yl) -6- (3'-chloro- [1,1'-biphenyl] -3-yl) -2-phenylpyrimidine, the same procedure as in [Synthesis Example 7] was carried out to obtain 2.7 g ( Yield 55%).
[LCMS] : 842[LCMS]: 842
[합성예 10] 화합물 43의 합성Synthesis Example 10 Synthesis of Compound 43
2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.2 g (수율 64%)을 얻었다.2- (3'-chloro- [1,1'- instead of 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine Except for using biphenyl] -3-yl) -6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine, the same procedure as in [Synthesis Example 7] was performed. g (yield 64%) was obtained.
[LCMS] : 805[LCMS]: 805
[합성예 11] 화합물 49의 합성Synthesis Example 11 Synthesis of Compound 49
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 65%)을 얻었다.4.5 g (yield 65%) of the title compound was obtained in the same manner as in [Synthesis Example 1], except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 614[LCMS]: 614
[합성예 12] 화합물 55의 합성Synthesis Example 12 Synthesis of Compound 55
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 3.5 g (수율 56%)을 얻었다.3.5 g (yield 56%) of the title compound was obtained in the same manner as in Synthesis Example 3, except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 587[LCMS]: 587
[합성예 13] 화합물 57의 합성Synthesis Example 13 Synthesis of Compound 57
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 4]와 동일한 과정을 수행하여 목적 화합물 2.9 g (수율 52%)을 얻었다.2.9 g (yield 52%) of the title compound was obtained in the same manner as in [Synthesis Example 4], except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 690[LCMS]: 690
[합성예 14] 화합물 59의 합성Synthesis Example 14 Synthesis of Compound 59
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 4.2 g (수율 45%)을 얻었다.A target compound 4.2 g (yield 45%) was obtained in the same manner as in Synthesis Example 6, except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 765[LCMS]: 765
[합성예 15] 화합물 74의 합성Synthesis Example 15 Synthesis of Compound 74
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.3 g (수율 55%)을 얻었다.6.3 g (yield 55%) of the title compound was obtained in the same manner as in [Synthesis Example 7], except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 766[LCMS]: 766
[합성예 16] 화합물 80의 합성Synthesis Example 16 Synthesis of Compound 80
[준비예 1]에서 얻어진 Core 1과 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 대신 [준비예 2에서 얻어진 Core 2와 4-(4'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine를 사용하는 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.9 g (수율 53%)을 얻었다.Preparation Example 2 Instead of Core 1 and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine obtained in Preparation Example 1 The same procedure as in [Synthesis Example 7] was carried out except that Core 2 and 4- (4'-chloro- [1,1'-biphenyl] -3-yl) -2,6-diphenylpyrimidine obtained in 4.9 g (53% yield) of compound were obtained.
[LCMS] : 765[LCMS]: 765
[합성예 17] 화합물 85의 합성Synthesis Example 17 Synthesis of Compound 85
[준비예 1]에서 얻어진 Core 1 대신 [준비예 2]에서 얻어진 Core 2를 사용한 것을 제외하고는 [합성예 9]와 동일한 과정을 수행하여 목적 화합물 3.3 g (수율 45%)을 얻었다.A target compound 3.3 g (yield 45%) was obtained in the same manner as in [Synthesis Example 9], except that Core 2 obtained in [Preparation Example 2] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 842[LCMS]: 842
[합성예 18] 화합물 94의 합성Synthesis Example 18 Synthesis of Compound 94
[준비예 1]에서 얻어진 Core 1 대신 [준비예 3]에서 얻어진 Core 3을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.0 g (수율 42%)을 얻었다.5.0 g (yield 42%) of the title compound was obtained in the same manner as in [Synthesis Example 1], except that Core 3 obtained in [Preparation Example 3] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 738[LCMS]: 738
[합성예 19] 화합물 98의 합성Synthesis Example 19 Synthesis of Compound 98
[준비예 1]에서 얻어진 Core 1 대신 [준비예 3]에서 얻어진 Core 3을 사용한 것을 제외하고는 [합성예 4]와 동일한 과정을 수행하여 목적 화합물 3.7 g (수율 54%)을 얻었다.3.7 g (yield 54%) of the title compound was obtained in the same manner as in [Synthesis Example 4], except that Core 3 obtained in [Preparation Example 3] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 814[LCMS]: 814
[합성예 20] 화합물 100의 합성Synthesis Example 20 Synthesis of Compound 100
[준비예 1]에서 얻어진 Core 1 대신 [준비예 3]에서 얻어진 Core 3을 사용한 것을 제외하고는 [합성예 5]와 동일한 과정을 수행하여 목적 화합물 4.0 g (수율 38%)을 얻었다.4.0 g (yield 38%) of the title compound was obtained in the same manner as in [Synthesis Example 5], except that Core 3 obtained in [Preparation Example 3] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 853[LCMS]: 853
[합성예 21] 화합물 109의 합성Synthesis Example 21 Synthesis of Compound 109
[준비예 1]에서 얻어진 Core 1 대신 [준비예 4]에서 얻어진 Core 4를 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.3 g (수율 46%)을 얻었다.5.3 g (yield 46%) of the title compound was obtained in the same manner as in [Synthesis Example 3], except that Core 4 obtained in [Preparation Example 4] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 711[LCMS]: 711
[합성예 22] 화합물 110의 합성Synthesis Example 22 Synthesis of Compound 110
[준비예 1]에서 얻어진 Core 1 대신 [준비예 4]에서 얻어진 Core 4를 사용한 것을 제외하고는 [합성예 4]와 동일한 과정을 수행하여 목적 화합물 4.2 g (수율 38%)을 얻었다.A target compound of 4.2 g (yield 38%) was obtained in the same manner as in Synthesis Example 4, except that Core 4 obtained in Preparation Example 4 was used instead of Core 1 obtained in Preparation Example 1.
[LCMS] : 814[LCMS]: 814
[합성예 23] 화합물 112의 합성Synthesis Example 23 Synthesis of Compound 112
[준비예 1]에서 얻어진 Core 1 대신 [준비예 4]에서 얻어진 Core 4를 사용한 것을 제외하고는 [합성예 5]와 동일한 과정을 수행하여 목적 화합물 3.0 g (수율 46%)을 얻었다.A target compound 3.0 g (yield 46%) was obtained in the same manner as in [Synthesis Example 5], except that Core 4 obtained in [Preparation Example 4] was used instead of Core 1 obtained in [Preparation Example 1].
[LCMS] : 853[LCMS]: 853
[실시예 1 내지 15] 녹색 유기 전계 발광 소자의 제작Examples 1 to 15 Fabrication of Green Organic Electroluminescent Devices
합성예에서 합성한 화합물 1, 5, 9, 13, 27, 31, 39, 43, 57, 59, 74, 80, 85, 94, 98를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compound 1, 5, 9, 13, 27, 31, 39, 43, 57, 59, 74, 80, 85, 94, 98 synthesized in Synthesis Example after high purity sublimation purification by a commonly known method According to the present invention, a green organic EL device was manufactured.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 5분간 세정하고 진공 증착기로 코팅된 유리 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically washed with distilled water glass substrate coated with a thin film of 1500 증류 thickness. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), washed with UV for 5 minutes and coated with a vacuum evaporator The substrate was transferred.
이렇게 준비된 ITO 투명 유리 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90 %의 화합물 1, 5, 9, 13, 27, 31, 39, 43, 57, 59, 74, 80, 85, 94, 98 + 10 %의 Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / 90% of compound 1, 5, 9, 13, 27, 31, 39, 43, 57, 59, 74, on the prepared ITO transparent glass substrate (electrode) Green organic by stacking in order of 80, 85, 94, 98 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) An electroluminescent device was produced.
[비교예 1] 녹색 유기 전계 발광 소자의 제작Comparative Example 1 Fabrication of Green Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 화합물 1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a light-emitting host material.
실시예 1 내지 15 및 비교예 1에서 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 in Examples 1 to 15 and Comparative Example 1 are as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 15 및 비교예 1에서 제작한 각각의 녹색 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 green organic electroluminescent devices fabricated in Examples 1 to 15 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. .
| 샘플Sample | 호스트Host | 구동전압(V)Driving voltage (V) | 발광 피크(nm)Emission Peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | 화합물 1Compound 1 | 4.34.3 | 458458 | 55.055.0 |
| 실시예 2Example 2 | 화합물 5Compound 5 | 3.93.9 | 459459 | 52.552.5 |
| 실시예 3Example 3 | 화합물 9Compound 9 | 4.84.8 | 458458 | 58.558.5 |
| 실시예 4Example 4 | 화합물 13Compound 13 | 3.83.8 | 459459 | 57.357.3 |
| 실시예 5Example 5 | 화합물 27Compound 27 | 4.24.2 | 459459 | 56.856.8 |
| 실시예 6Example 6 | 화합물 31Compound 31 | 4.24.2 | 457457 | 51.051.0 |
| 실시예 7Example 7 | 화합물 39Compound 39 | 3.93.9 | 458458 | 59.159.1 |
| 실시예 8Example 8 | 화합물 43Compound 43 | 4.54.5 | 459459 | 60.260.2 |
| 실시예 9Example 9 | 화합물 57Compound 57 | 4.24.2 | 458458 | 55.455.4 |
| 실시예 10Example 10 | 화합물 59Compound 59 | 3.93.9 | 457457 | 57.557.5 |
| 실시예 11Example 11 | 화합물 74Compound 74 | 3.83.8 | 459459 | 58.058.0 |
| 실시예 12Example 12 | 화합물 80Compound 80 | 4.24.2 | 458458 | 59.059.0 |
| 실시예 13Example 13 | 화합물 85Compound 85 | 4.54.5 | 458458 | 52.752.7 |
| 실시예 14Example 14 | 화합물 94Compound 94 | 4.04.0 | 459459 | 58.358.3 |
| 실시예 15Example 15 | 화합물 98Compound 98 | 3.83.8 | 458458 | 57.257.2 |
| 비교예 1Comparative Example 1 | CBPCBP | 5.25.2 | 459459 | 44.244.2 |
상기 표 1에 나타낸 바와 같이, 녹색 유기 전계 발광 소자의 유기물층에 포함된 발광층의 재료로 본 발명의 화합물을 적용한 경우(실시예 1 내지 15)가 종래의 CBP를 적용한 경우(비교예 1)보다 전류효율 및 구동전압이 우수한 것을 알 수 있다.As shown in Table 1, when the compound of the present invention is applied to the light emitting layer material included in the organic material layer of the green organic electroluminescent device (Examples 1 to 15), the current is higher than when the conventional CBP is applied (Comparative Example 1). It can be seen that the efficiency and driving voltage are excellent.
[실시예 16 내지 26] 적색 유기 전계 발광 소자의 제조[Examples 16 to 26] Preparation of Red Organic Electroluminescent Device
합성예에서 합성된 화합물 5, 7, 9, 20, 49, 55, 94, 100, 109, 110, 112을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.Compounds 5, 7, 9, 20, 49, 55, 94, 100, 109, 110, and 112 synthesized in the synthesis example were subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was prepared according to the following procedure. Produced.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 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 5분간 세정하고 진공 증착기로 코팅된 유리 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically washed with distilled water glass substrate coated with a thin film of 1500 증류 thickness. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed with UV for 5 minutes and vacuum evaporator The glass substrate coated with was transferred.
이렇게 준비된 ITO 투명 유리 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm) / 90 %의 화합물 5, 7, 9, 20, 49, 55, 94, 100, 109, 110, 112 + 10 %의 (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 적색 유기 전계 발광 소자를 제작하였다. 사용된 m-MTDATA, TCTA 및 BCP의 구조는 상기와 같고, (piq)2Ir(acac)의 구조는 하기와 같다.M-MTDATA (60 nm) / TCTA (80 nm) / 90% of compound 5, 7, 9, 20, 49, 55, 94, 100, 109, 110, 112 + on the prepared ITO transparent glass substrate (electrode) 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate a red organic electroluminescent device. It was. The structures of m-MTDATA, TCTA and BCP used are as described above, and the structure of (piq) 2 Ir (acac) is as follows.
[[
비교예Comparative example
2] 2]
발광층 형성시 발광 호스트 물질로서 화합물 5 대신 CBP를 사용하는 것을 제외하고는 실시예 16과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다. 사용된 CBP의 구조는 상기와 같다.A red organic electroluminescent device was manufactured in the same manner as in Example 16, except that CBP was used instead of Compound 5 as a light emitting host material when forming the emission layer. The structure of CBP used is as above.
[평가예 2][Evaluation Example 2]
실시예 16 내지 26 및 비교예 2에서 각각 제조된 적색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 2에 나타내었다.For red organic electroluminescent devices prepared in Examples 16 to 26 and Comparative Example 2, 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 2 below. .
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | 발광 피크(nm)Emission Peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 16Example 16 | 화합물 5Compound 5 | 4.54.5 | 519519 | 18.518.5 |
| 실시예 17Example 17 | 화합물 7Compound 7 | 4.24.2 | 519519 | 17.917.9 |
| 실시예 18Example 18 | 화합물 9Compound 9 | 4.04.0 | 518518 | 18.818.8 |
| 실시예 19Example 19 | 화합물 20Compound 20 | 3.83.8 | 519519 | 19.219.2 |
| 실시예 20Example 20 | 화합물 49Compound 49 | 4.14.1 | 518518 | 20.020.0 |
| 실시예 21Example 21 | 화합물 55Compound 55 | 4.54.5 | 520520 | 18.018.0 |
| 실시예 22Example 22 | 화합물 94 Compound 94 | 4.04.0 | 518518 | 17.217.2 |
| 실시예 23Example 23 | 화합물 100Compound 100 | 3.83.8 | 519519 | 19.219.2 |
| 실시예 24Example 24 | 화합물 109Compound 109 | 3.93.9 | 520520 | 18.518.5 |
| 실시예 25Example 25 | 화합물 110Compound 110 | 3.93.9 | 519519 | 18.218.2 |
| 실시예 26Example 26 | 화합물 112Compound 112 | 4.34.3 | 518518 | 19.419.4 |
| 비교예 2Comparative Example 2 | CBPCBP | 5.45.4 | 520520 | 14.514.5 |
상기 표 2에 나타낸 바와 같이, 적색 유기 전계 발광 소자의 유기물층에 포함된 발광층의 재료로 본 발명의 화합물을 적용한 경우(실시예 16 내지 26)가 종래 의 CBP를 적용한 경우(비교예 2)보다 전류효율 및 구동전압이 우수한 것을 알 수 있다.As shown in Table 2, the case of applying the compound of the present invention (Examples 16 to 26) as the material of the light emitting layer included in the organic material layer of the red organic electroluminescent device (comparative example 2) compared to the case of applying the conventional CBP (Comparative Example 2) It can be seen that the efficiency and the driving voltage are excellent.
Claims (7)
- 하기 화학식 1 또는 2로 표시되는 화합물:Compound represented by the following formula (1) or (2):[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 또는 2에서,In Chemical Formula 1 or 2,Ar1은 C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 is a C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group , C 1 ~ C 40 Alkyloxy 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 , is selected from the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,R1 내지 R3은 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ group C 60 aryl silyl group, C 1 ~ alkyl boron C 40 of, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C of It is selected from the group consisting of 6 ~ C 60 arylamine group,R4 내지 R5는 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 이들이 서로 결합하여 축합 고리를 형성하며,R 4 to R 5 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 6- C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ group C 60 aryl silyl group, C 1 ~ alkyl boron C 40 of, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C of 6 to C 60 arylamine group, or combine with each other to form a condensed ring,상기 Ar1 및 R1 내지 R5의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상으로 치환 또는 비치환되며,An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group of Ar 1 and R 1 to R 5 , The arylphosphine group, the arylphosphine oxide group, and the arylamine group are each independently deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocyclo Alkyl group, C 6 ~ C 60 Aryl group, Nuclear 5 to 60 heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine of C 60 Substituted or unsubstituted with one or more selected from the group consisting of a pin oxide group and an arylamine group of C 6 ~ C 60 ,a 내지 c는 각각 1 내지 4의 정수이다.a to c are each an integer of 1 to 4; - 제1항에 있어서,The method of claim 1,상기 Ar1은 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,Ar 1 is selected from the group consisting of C 6 ~ C 60 aryl group and heteroaryl group of 5 to 60 nuclear atoms,상기 Ar1의 아릴기 및 헤테로아릴기는 각각 독립적으로, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상으로 치환되는 화합물.The aryl group and heteroaryl group of Ar 1 are each independently substituted with at least one member selected from the group consisting of C 6 ~ C 60 aryl group and 5 to 60 nuclear atoms.
- 제1항에 있어서,The method of claim 1,상기 Ar1은 하기 S1 내지 S48로 표시되는 치환체로 이루어진 군에서 선택되는 화합물.Ar 1 is a compound selected from the group consisting of substituents represented by S1 to S48.
- 제1항에 있어서,The method of claim 1,상기 R1 내지 R3는 모두 수소인 화합물.R 1 to R 3 are all hydrogen.
- 제1항에 있어서,The method of claim 1,상기 R4 및 R5는 각각 독립적으로, 수소, C1~C40의 알킬기 및 C6~C60의 아릴기로 이루어진 군에서 선택되는 화합물.R 4 and R 5 are each independently selected from the group consisting of hydrogen, an alkyl group of C 1 ~ C 40 and an aryl group of C 6 ~ C 60 .
- 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode.상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제5항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 5.
- 제6항에 있어서,The method of claim 6,상기 화합물을 포함하는 유기물층은 발광층인 유기 전계 발광 소자.The organic material layer containing the compound is an organic electroluminescent device is a light emitting layer.
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| KR20110050588A (en) * | 2008-07-29 | 2011-05-16 | 메르크 파텐트 게엠베하 | Organic electroluminescent device |
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