WO2020262861A1 - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
- Publication number
- WO2020262861A1 WO2020262861A1 PCT/KR2020/007634 KR2020007634W WO2020262861A1 WO 2020262861 A1 WO2020262861 A1 WO 2020262861A1 KR 2020007634 W KR2020007634 W KR 2020007634W WO 2020262861 A1 WO2020262861 A1 WO 2020262861A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- group
- layer
- phenyl
- preparation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 134
- -1 dibenzofuranyl Chemical group 0.000 claims description 66
- 239000011368 organic material Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 152
- 238000002360 preparation method Methods 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 34
- 239000012044 organic layer Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 230000032258 transport Effects 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- 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 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 8
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 8
- MHYZYLQHHQNSPV-UHFFFAOYSA-N 4-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1C1=CC=CC=C1N2 MHYZYLQHHQNSPV-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229940126142 compound 16 Drugs 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- IMLDYQBWZHPGJA-UHFFFAOYSA-N 2-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3NC2=C1 IMLDYQBWZHPGJA-UHFFFAOYSA-N 0.000 description 7
- IAWRFMPNMXEJCK-UHFFFAOYSA-N 3-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 IAWRFMPNMXEJCK-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 5
- DDGPPAMADXTGTN-DYVTXVBDSA-N 2-chloro-4-(2,3,4,5,6-pentadeuteriophenyl)-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C(=C(C(=C1[2H])[2H])[2H])[2H])[2H] DDGPPAMADXTGTN-DYVTXVBDSA-N 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 4
- 0 Cc1nc(I)nc(*)n1 Chemical compound Cc1nc(I)nc(*)n1 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229940125758 compound 15 Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- 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 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- GKOXRVXZEAXITE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1c2c3cccc2)ccc1[n]3-c1c(-c2ccccc2)c(-c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)ccc1 Chemical compound c(cc1)ccc1-c(cc1c2c3cccc2)ccc1[n]3-c1c(-c2ccccc2)c(-c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)ccc1 GKOXRVXZEAXITE-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 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 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- MHYZYLQHHQNSPV-RCQSQLKUSA-N 4-(2,3,4,5,6-pentadeuteriophenyl)-9H-carbazole Chemical compound C1(=C(C(=C(C(=C1[2H])[2H])[2H])[2H])[2H])C1=CC=CC=2NC3=CC=CC=C3C12 MHYZYLQHHQNSPV-RCQSQLKUSA-N 0.000 description 2
- VUBLUROKZNABLO-UHFFFAOYSA-N 4-dibenzofuran-2-yl-9H-carbazole Chemical compound C1=C(C=CC=2OC3=C(C=21)C=CC=C3)C1=CC=CC=2NC3=CC=CC=C3C1=2 VUBLUROKZNABLO-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- KBZBTHMEJVZVBU-NSWZMOPOSA-N C/C(/C(N1)=C)=C/C=C\CC/C=C\C=C/C1=C Chemical compound C/C(/C(N1)=C)=C/C=C\CC/C=C\C=C/C1=C KBZBTHMEJVZVBU-NSWZMOPOSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HXITXNWTGFUOAU-RALIUCGRSA-N (2,3,4,5,6-pentadeuteriophenyl)boronic acid Chemical compound [2H]C1=C([2H])C([2H])=C(B(O)O)C([2H])=C1[2H] HXITXNWTGFUOAU-RALIUCGRSA-N 0.000 description 1
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- FPNVMCMDWZNTEU-UHFFFAOYSA-N 1-bromo-4-chloro-2-fluorobenzene Chemical compound FC1=CC(Cl)=CC=C1Br FPNVMCMDWZNTEU-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- NTEIZPBYXABJKN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NTEIZPBYXABJKN-UHFFFAOYSA-N 0.000 description 1
- GBESIUPWXGQOFP-UHFFFAOYSA-N 2-bromo-1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1Br GBESIUPWXGQOFP-UHFFFAOYSA-N 0.000 description 1
- YFFUYGSLQXVHMB-UHFFFAOYSA-N 2-bromo-4-chloro-1-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1Br YFFUYGSLQXVHMB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- PCMKGEAHIZDRFL-UHFFFAOYSA-N 3,6-diphenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 PCMKGEAHIZDRFL-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- JIHNZNBRECXPJB-UHFFFAOYSA-N 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)carbazole Chemical compound N=1C(N2C3=CC=CC=C3C3=CC=CC=C32)=NC(Cl)=NC=1C1=CC=CC=C1 JIHNZNBRECXPJB-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YFNLNQCSPQBGAT-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C=CC=C3N2)C4=NC5=CC=CC=C5S4 Chemical compound C1=CC=C2C(=C1)C3=C(C=CC=C3N2)C4=NC5=CC=CC=C5S4 YFNLNQCSPQBGAT-UHFFFAOYSA-N 0.000 description 1
- KXBVVZRZYGAHSW-UHFFFAOYSA-N CC1(C)OB(c(cc2)cc(-c3ccccc3)c2F)OC1(C)C Chemical compound CC1(C)OB(c(cc2)cc(-c3ccccc3)c2F)OC1(C)C KXBVVZRZYGAHSW-UHFFFAOYSA-N 0.000 description 1
- REJVUHHBPJIXFB-UHFFFAOYSA-N CC1(C)OB(c2cccc(F)c2-c2ccccc2)OC1(C)C Chemical compound CC1(C)OB(c2cccc(F)c2-c2ccccc2)OC1(C)C REJVUHHBPJIXFB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CWYPDLOPQFNIFA-UHFFFAOYSA-N Fc(ccc(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)c1)c1-c1ccccc1 Chemical compound Fc(ccc(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)c1)c1-c1ccccc1 CWYPDLOPQFNIFA-UHFFFAOYSA-N 0.000 description 1
- IOZMFDZVCMMIFB-UHFFFAOYSA-N Fc1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1-c1ccccc1 Chemical compound Fc1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1-c1ccccc1 IOZMFDZVCMMIFB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HKTIUFTYFBJMSJ-UHFFFAOYSA-N c(cc1)ccc1-c([s]c1c2)nc1ccc2-c1nc(-c2cccc(-[n](c(cccc3)c3c3ccc4)c3c4-c3ccccc3)c2-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c([s]c1c2)nc1ccc2-c1nc(-c2cccc(-[n](c(cccc3)c3c3ccc4)c3c4-c3ccccc3)c2-c2ccccc2)nc(-c2ccccc2)n1 HKTIUFTYFBJMSJ-UHFFFAOYSA-N 0.000 description 1
- VYAHGICCOUKART-UHFFFAOYSA-N c(cc1)ccc1-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)ccc1)c1-[n]1c(ccc(-c2nc3ccccc3[o]2)c2)c2c2ccccc12 Chemical compound c(cc1)ccc1-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)ccc1)c1-[n]1c(ccc(-c2nc3ccccc3[o]2)c2)c2c2ccccc12 VYAHGICCOUKART-UHFFFAOYSA-N 0.000 description 1
- VIQZITDCGUMLDZ-UHFFFAOYSA-N c(cc1)ccc1-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)ccc1)c1-[n]1c2cccc(-c3nc(cccc4)c4[s]3)c2c2ccccc12 Chemical compound c(cc1)ccc1-c(c(-c1nc(-c2ccccc2)nc(-c2ccccc2)n1)ccc1)c1-[n]1c2cccc(-c3nc(cccc4)c4[s]3)c2c2ccccc12 VIQZITDCGUMLDZ-UHFFFAOYSA-N 0.000 description 1
- GCJOSKMUXFPOLP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1c(-c2ccccc2)c(-c2nc(-c3c4[o]c(cccc5)c5c4ccc3)nc(-c3c4[s]c5ccccc5c4ccc3)n2)ccc1 Chemical compound c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1c(-c2ccccc2)c(-c2nc(-c3c4[o]c(cccc5)c5c4ccc3)nc(-c3c4[s]c5ccccc5c4ccc3)n2)ccc1 GCJOSKMUXFPOLP-UHFFFAOYSA-N 0.000 description 1
- GYBOGTDQXDLEKT-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c1c(-c2ccccc2)c(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c1c(-c2ccccc2)c(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 GYBOGTDQXDLEKT-UHFFFAOYSA-N 0.000 description 1
- IEEBMSBBCBJKAD-UHFFFAOYSA-N c(cc1)ccc1-c(cc1c2ccccc22)ccc1[n]2-c1c(-c2ccccc2)c(-c(cc2)c(cccc3)c3c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound c(cc1)ccc1-c(cc1c2ccccc22)ccc1[n]2-c1c(-c2ccccc2)c(-c(cc2)c(cccc3)c3c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 IEEBMSBBCBJKAD-UHFFFAOYSA-N 0.000 description 1
- BOJKMHHXUBAGBL-UHFFFAOYSA-N c(cc1)ccc1-c1ccc(c(cccc2)c2[n]2-c3c(-c4ccccc4)c(-c4nc(-c5ccccc5)nc(-c5nc(cc(cc6)-c7ccccc7)c6[s]5)n4)ccc3)c2c1 Chemical compound c(cc1)ccc1-c1ccc(c(cccc2)c2[n]2-c3c(-c4ccccc4)c(-c4nc(-c5ccccc5)nc(-c5nc(cc(cc6)-c7ccccc7)c6[s]5)n4)ccc3)c2c1 BOJKMHHXUBAGBL-UHFFFAOYSA-N 0.000 description 1
- WOUVRQOIVFURAT-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c1c(-c2ccccc2)c(-c(cccc2)c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound c(cc1)ccc1-c1cccc(c2c3cccc2)c1[n]3-c1c(-c2ccccc2)c(-c(cccc2)c2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 WOUVRQOIVFURAT-UHFFFAOYSA-N 0.000 description 1
- OAFANJAPNOSPGW-UHFFFAOYSA-N c(cc1)ccc1-c1nc(cc(cc2)-c3c(c(cccc4)c4[n]4-c5c(-c6ccccc6)c(-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)ccc5)c4ccc3)c2[s]1 Chemical compound c(cc1)ccc1-c1nc(cc(cc2)-c3c(c(cccc4)c4[n]4-c5c(-c6ccccc6)c(-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)ccc5)c4ccc3)c2[s]1 OAFANJAPNOSPGW-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
- An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
- the organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
- the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.
- a voltage when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
- Patent Document 1 Korean Patent Publication No. 10-2000-0051826
- the present invention relates to a novel organic light emitting material and an organic light emitting device including the same.
- the present invention provides a compound represented by the following formula 1:
- L is connected to carbon 1, carbon 2, or carbon 3,
- L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
- Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
- Each R 1 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
- R 2 is each independently substituted or unsubstituted C 6-60 aryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or phenyl benzothiophenyl,
- p is an integer from 0 to 5
- q is an integer from 1 to 8.
- the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .
- the compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
- the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
- FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9).
- An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown.
- the present invention provides a compound represented by Chemical Formula 1.
- substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two
- a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
- the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
- it may be a compound of the following structural formula, but is not limited thereto.
- the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
- the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
- the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
- the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
- the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
- the aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto.
- the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
- Etc When the fluorenyl group is substituted, Etc.
- Etc it is not limited thereto.
- the heteroaryl group is a heteroaryl group including one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms.
- heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthro
- the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
- the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
- the above description of the heteroaryl group may be applied.
- the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
- the description of the aryl group described above may be applied except that the arylene is a divalent group.
- the description of the aforementioned heteroaryl group may be applied except that the heteroarylene is a divalent group.
- the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
- the heteroaryl is not a monovalent group, and the description of the heteroaryl group described above may be applied, except that two substituents are bonded to each other.
- Formula 1 may be represented by the following Formulas 1-1 to 1-3:
- L is a single bond; Or it may be a substituted or unsubstituted C 6-20 arylene,
- L may be a single bond, phenylene, or naphthylene.
- Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted N, O and S may be a C 2-20 heteroaryl including any one or more selected from the group consisting of,
- Ar 1 and Ar 2 are each independently phenyl, biphenylyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with 5 deuteriums, carbazolyl phenyl, or May be phenyl benzothiophenyl,
- Ar 1 and Ar 2 may each independently be any one selected from the group consisting of:
- each R 1 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted N, O and S may be a C 2-20 heteroaryl including any one or more selected from the group consisting of,
- R 1 may each independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.
- R 2 may each independently be a substituted or unsubstituted C 6-20 aryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or phenyl benzothiophenyl,
- R 2 may each independently be any one selected from the group consisting of:
- q may be 1 or 2.
- the compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below, for example, and other compounds may be prepared similarly.
- L, Ar 1 , Ar 2 , R 1 , R 2 , p and q are the same as defined in Formula 1, and X 1 and X 2 are each independently halogen, preferably X 1 and X 2 is fluoro, chloro or bromo.
- Step 1 of Scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction may be changed as known in the art.
- step 2 of Scheme 1 is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be changed as known in the art.
- the manufacturing method may be more specific in the manufacturing examples to be described later.
- the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1.
- the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
- the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
- the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above.
- the compound according to the present invention can be used as a host of a light emitting layer.
- the organic material layer may include a hole transport layer, a hole injection layer, or a layer for simultaneously transporting and injecting holes, and the layer for simultaneously transporting and injecting holes is the above formula It may contain a compound represented by 1.
- the electron transport layer, the electron injection layer, or a layer that simultaneously transports electrons and injects electrons may include the compound represented by Formula 1 above.
- the organic material layer may include an emission layer and a hole transport layer, and the emission layer or the hole transport layer may include a compound represented by Formula 1 above.
- the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIGS. 1 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
- FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- the compound represented by Formula 1 may be included in the emission layer.
- FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9).
- An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown.
- the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
- the organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1.
- the organic material layers may be formed of the same material or different materials.
- the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
- the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
- an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
- an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
- the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode
- the second electrode is an anode
- the cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
- the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
- the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
- the hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material.
- a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable.
- the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
- a hole transport material a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable.
- Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
- the electron blocking layer is a layer interposed between the hole transport layer and the light emitting layer in order to prevent electrons injected from the cathode from passing over to the hole transport layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer.
- the electron blocking layer is preferably a material having less electron affinity than the electron transport layer.
- the light-emitting material a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable.
- the emission layer may include a host material and a dopant material.
- Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
- condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives and the like, but are not limited thereto.
- the compound represented by Formula 1 may be included as a host material.
- Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
- the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
- the styrylamine compound is substituted or unsubstituted
- the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
- the styrylamine compound is substituted or unsubstituted
- at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting
- the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
- the hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppressing layer.
- a material having high ionization energy is preferable for the hole blocking layer.
- the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
- an electron transport material a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used according to the prior art.
- suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.
- the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
- the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
- the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
- the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
- compound 1-b 50 g, 167.7 mmol
- 2-chloro-4,6-diphenyl-1,3,5-triazine 44.9 g, 167.7 mmol
- potassium carbonate 69.5 g, 503.1 mmol
- tetrakis (triphenylphosphine) palladium 5.8 g, 5 mmol
- compound 11-a (30 g, 145.2 mmol) and bis (pinacolato) diboron (36.9 g, 145.2 mmol) were added to 600 ml of Diox and stirred and refluxed. After that, potassium acetate (92.5 g, 435.5 mmol) was added, and sufficiently stirred Pd(dba) 2 (2.5 g, 4.4 mmol) and tricyclohexylphosphine (2.4 g, 8.7 mmol) were added. After reacting for 6 hours, cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled.
- compound 16-a (30 g, 145.2 mmol) and bis (pinacolato) diboron (36.9 g, 145.2 mmol) were added to 600 ml of Diox and stirred and refluxed. Thereafter, potassium acetate (92.5 g, 435.5 mmol) was added, stirred sufficiently, and then Pd(dba) 2 (2.5 g, 4.4 mmol) and tricyclohexylphosphine (2.4 g, 8.7 mmol) were added. After reacting for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled.
- compound 16-b 50 g, 167.7 mmol
- 2-chloro-4,6-diphenyl-1,3,5-triazine 44.9 g, 167.7 mmol
- potassium carbonate 69.5 g, 503.1 mmol
- tetrakis (triphenylphosphine) palladium 5.8 g, 5 mmol
- a glass substrate coated with a thin film of 1400 ⁇ of ITO Indium Tin Oxide
- ITO Indium Tin Oxide
- Fischer Co. product was used as a detergent
- distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
- ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
- the substrate was transported to a vacuum evaporator.
- the following compound HT-A and the following compound PD were thermally vacuum deposited to a thickness of 100 ⁇ at a weight ratio of 95:5, and then only the following compound HT-A was deposited to a thickness of 1150 ⁇ to form a hole transport layer. Formed.
- the following compound HT-B was thermally vacuum deposited to a thickness of 450 ⁇ to form an electron blocking layer.
- a light emitting layer was formed by vacuum deposition of Compound 1 prepared above and Compound GD below to a thickness of 400 ⁇ at a weight ratio of 85:15.
- the following compound ET-A was vacuum deposited to a thickness of 50 ⁇ to form a hole blocking layer.
- the following compound ET-B and the following compound Liq were thermally vacuum deposited to a thickness of 250 ⁇ at a weight ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 ⁇ at a weight ratio of 1:1.
- an electron transport and injection layer was formed.
- magnesium and silver were deposited to a thickness of 160 ⁇ in a weight ratio of 1:4 to form a cathode, thereby manufacturing an organic light emitting device.
- the deposition rate of organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 ⁇ /sec, and the deposition rate of silver and magnesium was 2 ⁇ /sec. Maintaining *10 -7 ⁇ 5 *10 -6 torr, an organic light emitting device was manufactured.
- An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in Example 1.
- Examples 21 to 25 and Comparative Examples 9 to 11 an organic light-emitting device was manufactured by using the compound shown in Table 1 below in a weight ratio of 1:1 instead of Compound 1.
- Example 21 instead of Compound 1 in Example 1, Compound 2 and Compound H-2 were used in a weight ratio of 1:1.
- compounds H-2 and C1 to C8 are as follows, respectively.
- Voltage, efficiency, and lifetime were measured by applying a current to the organic light-emitting devices manufactured in the above Examples and Comparative Examples, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
- Examples 1 to 20 and Comparative Examples 1 to 8 are examples of organic light emitting devices using a single host for the emission layer, and Examples 21 to 25 and Comparative Examples 9 to 11 use two types of hosts for the emission layer. This is an example of a device.
- the organic light-emitting device of the Example using the compound of the present invention has higher efficiency and higher driving voltage than the organic light-emitting device of Comparative Example. It was confirmed that it was low, and in particular, the life characteristics were greatly improved.
- substrate 2 anode
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention provides a novel compound and an organic light emitting device comprising same.
Description
관련 출원(들)과의 상호 인용Cross-reference with related application(s)
본 출원은 2019년 6월 27일자 한국 특허 출원 제10-2019-0077351호 및 2020년 6월 9일자 한국 특허 출원 제10-2020-0069692호에 기초한 우선권의 이익을 주장하며, 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다.This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0077351 filed June 27, 2019 and Korean Patent Application No. 10-2020-0069692 filed June 9, 2020. All contents disclosed in the literature are included as part of this specification.
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. The organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.
선행기술문헌Prior art literature
특허문헌Patent Literature
(특허문헌 1) 한국특허 공개번호 제10-2000-0051826호(Patent Document 1) Korean Patent Publication No. 10-2000-0051826
본 발명은 신규한 유기발광 재료 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting material and an organic light emitting device including the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by the following formula 1:
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
L은 1번 탄소, 2번 탄소, 또는 3번 탄소에 연결되고,L is connected to carbon 1, carbon 2, or carbon 3,
L은 단일결합; 또는 치환 또는 비치환된 C
6-60 아릴렌이고,L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
Ar
1 및 Ar
2는 각각 독립적으로, 치환 또는 비치환된 C
6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R
1은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C
6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-60 헤테로아릴이고,Each R 1 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R
2는 각각 독립적으로 치환 또는 비치환된 C
6-60 아릴, 벤조퓨라닐, 벤조티오페닐, 디벤조퓨라닐, 또는 페닐 벤조티오페닐이고,R 2 is each independently substituted or unsubstituted C 6-60 aryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or phenyl benzothiophenyl,
p는 0 내지 5인 정수이고,p is an integer from 0 to 5,
q는 1 내지 8인 정수이다.q is an integer from 1 to 8.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송, 정공주입 및 수송, 발광, 전자수송, 또는 전자주입 재료로 사용될 수 있다.The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 전자차단층(7), 발광층(3), 정공저지층(8), 전자수송층(9), 전자주입층(10) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9). , An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail to aid in understanding the present invention.
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by Chemical Formula 1.
본 명세서에서,
또는
는 다른 치환기에 연결되는 결합을 의미한다. In this specification, or Means a bond connected to another substituent.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우,
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, Etc. However, it is not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로아릴기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 헤테로아릴기의 탄소수는 6 내지 20이다. 헤테로아릴기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group is a heteroaryl group including one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiiadia There may be a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴은 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the above description of the heteroaryl group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heteroaryl group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heteroaryl is not a monovalent group, and the description of the heteroaryl group described above may be applied, except that two substituents are bonded to each other.
바람직하게는, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-3으로 표시될 수 있다:Preferably, Formula 1 may be represented by the following Formulas 1-1 to 1-3:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
상기 화학식 1-1 내지 화학식 1-3에서,In Formulas 1-1 to 1-3,
L, Ar
1, Ar
2, R
1, R
2, p 및 q에 대한 설명은 상기 화학식 1에서 정의한 바와 같다.Description of L, Ar 1 , Ar 2 , R 1 , R 2 , p and q are as defined in Chemical Formula 1.
바람직하게는, L은 단일결합; 또는 치환 또는 비치환된 C
6-20 아릴렌일 수 있고,Preferably, L is a single bond; Or it may be a substituted or unsubstituted C 6-20 arylene,
보다 바람직하게는, L은 단일결합, 페닐렌, 또는 나프틸렌일 수 있다.More preferably, L may be a single bond, phenylene, or naphthylene.
바람직하게는, Ar
1 및 Ar
2는 각각 독립적으로, 치환 또는 비치환된 C
6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-20 헤테로아릴일 수 있고,Preferably, Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted N, O and S may be a C 2-20 heteroaryl including any one or more selected from the group consisting of,
보다 바람직하게는, Ar
1 및 Ar
2는 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 카바졸릴, 디벤조퓨라닐, 디벤조티오페닐, 5개의 중수소로 치환된 페닐, 카바졸릴 페닐, 또는 페닐 벤조티오페닐일 수 있고,More preferably, Ar 1 and Ar 2 are each independently phenyl, biphenylyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with 5 deuteriums, carbazolyl phenyl, or May be phenyl benzothiophenyl,
가장 바람직하게는, Ar
1 및 Ar
2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:Most preferably, Ar 1 and Ar 2 may each independently be any one selected from the group consisting of:
바람직하게는, R
1은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C
6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C
2-20 헤테로아릴일 수 있고,Preferably, each R 1 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or substituted or unsubstituted N, O and S may be a C 2-20 heteroaryl including any one or more selected from the group consisting of,
보다 바람직하게는, R
1은 각각 독립적으로 수소, 중수소, 페닐, 카바졸릴, 디벤조퓨라닐, 또는 디벤조티오페닐일 수 있다.More preferably, R 1 may each independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.
바람직하게는, R
2는 각각 독립적으로 치환 또는 비치환된 C
6-20 아릴, 벤조퓨라닐, 벤조티오페닐, 디벤조퓨라닐, 또는 페닐 벤조티오페닐일 수 있고,Preferably, R 2 may each independently be a substituted or unsubstituted C 6-20 aryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or phenyl benzothiophenyl,
보다 바람직하게는, R
2는 각각 독립적으로, 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:More preferably, R 2 may each independently be any one selected from the group consisting of:
바람직하게는, q는 1 또는 2일 수 있다.Preferably, q may be 1 or 2.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of the compound represented by Formula 1 are as follows:
상기 화학식 1로 표시되는 화합물은, 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.The compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below, for example, and other compounds may be prepared similarly.
[반응식 1][Scheme 1]
상기 반응식 1에서, L, Ar
1, Ar
2, R
1, R
2, p 및 q는 상기 화학식 1에서 정의한 바와 같으며, X
1 및 X
2는 각각 독립적으로 할로겐이고, 바람직하게는 X
1 및 X
2는 플루오로, 클로로 또는 브로모이다.In Reaction Scheme 1, L, Ar 1 , Ar 2 , R 1 , R 2 , p and q are the same as defined in Formula 1, and X 1 and X 2 are each independently halogen, preferably X 1 and X 2 is fluoro, chloro or bromo.
상기 반응식 1의 단계 1은 스즈키 커플링 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 또한, 상기 반응식 1의 단계 2는 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. Step 1 of Scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction may be changed as known in the art. In addition, step 2 of Scheme 1 is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. In addition, the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 전자차단층,발광층, 정공저지층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 특히, 본 발명에 따른 화합물은 발광층의 호스트로 사용할 수 있다. In addition, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above. In particular, the compound according to the present invention can be used as a host of a light emitting layer.
또한, 상기 유기물 층은 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층을 포함할 수 있고, 상기 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer for simultaneously transporting and injecting holes, and the layer for simultaneously transporting and injecting holes is the above formula It may contain a compound represented by 1.
또한, 상기 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the electron transport layer, the electron injection layer, or a layer that simultaneously transports electrons and injects electrons may include the compound represented by Formula 1 above.
또한, 상기 유기물 층은 발광층 및 정공수송층을 포함하고, 상기 발광층 또는 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer may include an emission layer and a hole transport layer, and the emission layer or the hole transport layer may include a compound represented by Formula 1 above.
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Formula 1 may be included in the emission layer.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 전자차단층(7), 발광층(3), 정공저지층(8), 전자수송층(9), 전자주입층(10) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport layer (9). , An example of an organic light-emitting device comprising an electron injection layer 10 and a cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층 및 전자수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO
2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO
2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.As a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
상기 전자차단층은 음극에서 주입된 전자가 발광층에서 재결합되지 않고 정공수송층으로 넘어가는 것을 방지하기 위해 정공수송층과 발광층의 사이에 두는 층으로는 층으로, 전자저지층으로 불리기도 한다. 전자차단층에는 전자수송층보다 전자 친화력이 작은 물질이 바람직하다.The electron blocking layer is a layer interposed between the hole transport layer and the light emitting layer in order to prevent electrons injected from the cathode from passing over to the hole transport layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer. The electron blocking layer is preferably a material having less electron affinity than the electron transport layer.
상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq
3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. As the light-emitting material, a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 바람직하게는, 상기 화학식 1로 표시되는 화합물을 호스트 재료로 포함할 수 있다.The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives and the like, but are not limited thereto. Preferably, the compound represented by Formula 1 may be included as a host material.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
상기 정공저지층은 양극에서 주입된 정공이 발광층에서 재결합되지 않고 전자수송층으로 넘어가는 것을 방지하기 위해 전자수송층과 발광층의 사이에 두는 층으로, 정공억제층으로 불리기도 한다. 정공저지층에는 이온화에너지가 큰 물질이 바람직하다.The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppressing layer. A material having high ionization energy is preferable for the hole blocking layer.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq
3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.Preparation of the compound represented by Formula 1 and an organic light emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
제조예 1: 화합물 1의 제조Preparation Example 1: Preparation of Compound 1
단계 1) 화합물 1-a의 제조Step 1) Preparation of compound 1-a
질소 분위기에서 2-브로모-4-클로로-1-플루오로벤젠(50 g, 238.7 mmol)와 페닐 보론산(29.1 g, 238.7 mmol)를 테트라하이드로 퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(99 g, 716.2 mmol)를 물 99 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(8.3 g, 7.2 mmol)을 투입하였다. 2 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 987 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올재결정을 통해 흰색의 고체 화합물 1-a(34.5 g, 70 %, MS: [M+H]+ = 207.6)를 제조하였다.In a nitrogen atmosphere, 2-bromo-4-chloro-1-fluorobenzene (50 g, 238.7 mmol) and phenyl boronic acid (29.1 g, 238.7 mmol) were added to 1000 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (99 g, 716.2 mmol) was dissolved in 99 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3 g, 7.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 987 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl alcohol to prepare a white solid compound 1-a (34.5 g, 70%, MS: [M+H]+ = 207.6).
단계2) 화합물 1-b의 제조Step 2) Preparation of compound 1-b
질소 분위기에서 화합물 1-a(30 g, 145.2 mmol)와 비스(피나콜라토)디보론(36.9 g, 145.2 mmol)를 Diox 600 ml에 넣고 교반 및 환류하였다. 이 후 칼륨아세테이트(92.5 g, 435.5 mmol)를 투입하고 충분히 교반한 후 Pd(dba)
2(2.5 g, 4.4 mmol) 및 트리시클로헥실포스핀(2.4 g, 8.7 mmol) 을 투입하였다. 3시간 반응 후 상온으로 식힌 후 유기층을 필터처리하여 염을 제거 한 후 걸러진 유기층을 증류하였다. 이를 다시 클로로포름 10 배 433 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에탄올 재결정을 통해 흰색의 고체 화합물 1-b(34.2 g, 79 %, MS: [M+H]+ = 299.2)을 제조하였다.Compound 1-a (30 g, 145.2 mmol) and bis (pinacolato) diboron (36.9 g, 145.2 mmol) were added to 600 ml of Diox, and stirred and refluxed in a nitrogen atmosphere. Thereafter, potassium acetate (92.5 g, 435.5 mmol) was added, stirred sufficiently, and then Pd(dba) 2 (2.5 g, 4.4 mmol) and tricyclohexylphosphine (2.4 g, 8.7 mmol) were added. After reacting for 3 hours, cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 10 times 433 ml of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethanol to prepare a white solid compound 1-b (34.2 g, 79%, MS: [M+H]+ = 299.2).
단계3) 화합물 1-c의 제조Step 3) Preparation of compound 1-c
질소 분위기에서 화합물 1-b(50 g, 167.7 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진(44.9 g, 167.7 mmol)를 테트라하이드로퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(69.5 g, 503.1 mmol)를 물 70 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(5.8 g, 5 mmol)을 투입하였다. 3 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 1353 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올재결정을 통해 흰색의 고체 화합물 1-c(47.4 g, 70 %, MS: [M+H]+ = 404.5)을 제조하였다.In a nitrogen atmosphere, compound 1-b (50 g, 167.7 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (44.9 g, 167.7 mmol) were added to 1000 ml of tetrahydrofuran and stirred. And refluxed. Thereafter, potassium carbonate (69.5 g, 503.1 mmol) was dissolved in 70 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8 g, 5 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 1353 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl alcohol to prepare a white solid compound 1-c (47.4 g, 70%, MS: [M+H]+ = 404.5).
단계4) 화합물 1의 제조Step 4) Preparation of compound 1
질소 분위기에서 화합물 1-c(20 g, 43.4 mmol)와 3-페닐-9H-카바졸(10.6 g, 43.4 mmol)을 다이메틸포름아마이드 400 ml에 넣고 교반 및 환류하였다. 이 후 세슘카보네이트(42.4 g, 130.3 mmol)를 투입하고 가온 및 교반하였다. 3시간 반응 후 상온으로 식힌 후 생성된 고체를 여과하였다. 고체를 클로로포름 30 배 817 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸아세테이트를 이용하여 실리카 컬럼을 통해 정제하여 노랑의 고체 화합물 1(20.1 g, 74 %, MS: [M+H]+ = 627.8)을 제조하였다.In a nitrogen atmosphere, compound 1-c (20 g, 43.4 mmol) and 3-phenyl-9H-carbazole (10.6 g, 43.4 mmol) were added to 400 ml of dimethylformamide, followed by stirring and refluxing. After this, cesium carbonate (42.4 g, 130.3 mmol) was added, followed by heating and stirring. After reacting for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 817 ml of 30 times chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 1 (20.1 g, 74%, MS: [M+H]+ = 627.8).
제조예 2: 화합물 2의 제조Preparation Example 2: Preparation of Compound 2
제조예 1에서, 페닐 보론산 대신 (페닐-d5)보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2를 제조하였다. (MS: [M+H]+ = 632.3)In Preparation Example 1, except that (phenyl-d5) boronic acid was used instead of phenyl boronic acid, compound 2 was prepared in the same manner as in the preparation method of compound 1. (MS: [M+H]+ = 632.3)
제조예 3: 화합물 3의 제조Preparation Example 3: Preparation of compound 3
제조예 1에서, 3-페닐-9H-카바졸 대신 4-(페닐-d5)-9H-카바졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3를 제조하였다. (MS[M+H]
+= 632)In Preparation Example 1, compound 3 was prepared in the same manner as in the preparation method of Compound 1, except that 4-(phenyl-d5)-9H-carbazole was used instead of 3-phenyl-9H-carbazole. (MS[M+H] + = 632)
제조예 4: 화합물 4의 제조Preparation Example 4: Preparation of compound 4
제조예 1에서, 3-페닐-9H-카바졸 대신 4-(디벤조[b,d]퓨란-2-일)-9H-카바졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4를 제조하였다. (MS[M+H]
+= 717)In Preparation Example 1, except that 4-(dibenzo[b,d]furan-2-yl)-9H-carbazole was used instead of 3-phenyl-9H-carbazole, the same preparation as the preparation method of compound 1 Compound 4 was prepared by the method. (MS[M+H] + = 717)
제조예 5: 화합물 5의 제조Preparation Example 5: Preparation of compound 5
제조예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 3-페닐-9H-카바졸 대신 9-(4-클로로-6-페닐-1,3,5-트리아진-2-일)-9H-카바졸 및 2-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 5를 제조하였다. (MS[M+H]
+= 716)In Preparation Example 1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3-phenyl-9H-carbazole, 9-(4-chloro-6-phenyl-1,3,5 -Triazin-2-yl)-9H-carbazole and 2-phenyl-9H-carbazole, except for using the compound 5 was prepared in the same manner as in the preparation method of compound 1. (MS[M+H] + = 716)
제조예 6: 화합물 6의 제조Preparation Example 6: Preparation of compound 6
제조예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 3-페닐-9H-카바졸 대신 2-클로로-4-(디벤조[b,d]티오펜-4-일)-6-페닐-1,3,5-트리아진 및 4-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 6를 제조하였다. (MS[M+H]
+= 733)In Preparation Example 1, 2-chloro-4-(dibenzo[b,d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3-phenyl-9H-carbazole Compound 6 was prepared in the same manner as in the preparation method of Compound 1, except that -4-yl)-6-phenyl-1,3,5-triazine and 4-phenyl-9H-carbazole were used. (MS[M+H] + = 733)
제조예 7: 화합물 7의 제조Preparation Example 7: Preparation of compound 7
제조예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 대신 2-클로로-4-(디벤조[b,d]퓨란-4-일)-6-(디벤조[b,d]티오펜-4-일)-1,3,5-트리아진을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 7를 제조하였다. (MS[M+H]
+= 823)In Preparation Example 1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-(di Except that benzo[b,d]thiophen-4-yl)-1,3,5-triazine was used, compound 7 was prepared in the same manner as in the preparation method of compound 1. (MS[M+H] + = 823)
제조예 8: 화합물 8의 제조Preparation Example 8: Preparation of compound 8
제조예 1에서, 페닐 보론산 대신 (3-(9H-카바졸-9-일)페닐)보론산을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 8를 제조하였다. (MS[M+H]
+= 792)In Preparation Example 1, except that (3-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of phenyl boronic acid, compound 8 was prepared in the same manner as in the preparation method of compound 1. (MS[M+H] + = 792)
제조예 9: 화합물 9의 제조Preparation Example 9: Preparation of compound 9
제조예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 3-페닐-9H-카바졸 대신 2-(3-클로로페닐)-4,6-디페닐-1,3,5-트리아진 및 4-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 9를 제조하였다. (MS[M+H]
+= 703)In Preparation Example 1, 2-(3-chlorophenyl)-4,6-diphenyl- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3-phenyl-9H-carbazole Except for using 1,3,5-triazine and 4-phenyl-9H-carbazole, compound 9 was prepared in the same manner as in the preparation method of compound 1. (MS[M+H] + = 703)
제조예 10: 화합물 10의 제조Preparation Example 10: Preparation of Compound 10
제조예 1에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 3-페닐-9H-카바졸 대신 2-(3-클로로페닐)-4,6-디페닐-1,3,5-트리아진 및 2-(9H-카바졸-4-일)벤조[d]싸이아졸을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 10를 제조하였다. (MS[M+H]
+= 760)In Preparation Example 1, 2-(3-chlorophenyl)-4,6-diphenyl- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3-phenyl-9H-carbazole Except for using 1,3,5-triazine and 2-(9H-carbazol-4-yl)benzo[d]thiazole, Compound 10 was prepared in the same manner as in the preparation method of Compound 1. (MS[M+H] + = 760)
제조예 11: 화합물 11의 제조Preparation Example 11: Preparation of compound 11
단계 1) 화합물 11-a의 제조Step 1) Preparation of compound 11-a
질소 분위기에서 1-브로모-4-클로로-2-플루오로벤젠(50 g, 238.7 mmol)과 페닐 보론산(29.1 g, 238.7 mmol)를 테트라하이드로 퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(99 g, 716.2 mmol)를 물 99 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(8.3 g, 7.2 mmol)을 투입하였다. 1 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 987 ml에 투입하여 녹이고, 물로 2 회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올재결정을 통해 흰색의 고체 화합물 11-a(30.1 g, 61 %, MS: [M+H]+ = 207.6)을 제조하였다.In a nitrogen atmosphere, 1-bromo-4-chloro-2-fluorobenzene (50 g, 238.7 mmol) and phenyl boronic acid (29.1 g, 238.7 mmol) were added to 1000 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (99 g, 716.2 mmol) was dissolved in 99 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3 g, 7.2 mmol) was added. After the reaction for 1 hour, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 987 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl alcohol to prepare white solid compound 11-a (30.1 g, 61%, MS: [M+H]+ = 207.6).
단계2) 화합물 11-b의 제조Step 2) Preparation of compound 11-b
질소 분위기에서 화합물 11-a(30 g, 145.2 mmol)와 비스(피나콜라토)디보론(36.9 g, 145.2 mmol)를 Diox 600 ml에 넣고 교반 및 환류하였다. 이 후 칼륨아세테이트(92.5 g, 435.5 mmol)을 투입하고 충분히 교반한 Pd(dba)
2(2.5 g, 4.4 mmol) 및 트리시클로헥실포스핀(2.4 g, 8.7 mmol) 을 투입하였다. 6시간 반응 후 상온으로 식힌 후 유기층을 필터처리하여 염을 제거 한 후 걸러진 유기층을 증류하였다. 이를 다시 클로로포름 10 배 433 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에탄올 재결정을 통해 흰색의 고체 화합물 11-b(32 g, 74 %, MS: [M+H]+ = 299.2)을 제조하였다.In a nitrogen atmosphere, compound 11-a (30 g, 145.2 mmol) and bis (pinacolato) diboron (36.9 g, 145.2 mmol) were added to 600 ml of Diox and stirred and refluxed. After that, potassium acetate (92.5 g, 435.5 mmol) was added, and sufficiently stirred Pd(dba) 2 (2.5 g, 4.4 mmol) and tricyclohexylphosphine (2.4 g, 8.7 mmol) were added. After reacting for 6 hours, cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 10 times 433 ml of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethanol to prepare a white solid compound 11-b (32 g, 74%, MS: [M+H]+ = 299.2).
단계3) 화합물 1-c의 제조Step 3) Preparation of compound 1-c
질소 분위기에서 11-b(50 g, 167.7 mmol)와 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진(45.7 g, 167.7 mmol)를 테트라하이드로 퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(69.5 g, 503.1 mmol)를 물70 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(5.8 g, 5 mmol)을 투입하였다. 1 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 1370 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올 재결정을 통해 흰색의 고체 화합물 11-c(48.6 g, 71 %, MS: [M+H]+ = 409.5)을 제조하였다.In a nitrogen atmosphere, 11-b (50 g, 167.7 mmol) and 2-chloro-4-phenyl-6- (phenyl-d5)-1,3,5-triazine (45.7 g, 167.7 mmol) were added to tetrahydrofuran 1000 ml and stirred and refluxed. Thereafter, potassium carbonate (69.5 g, 503.1 mmol) was dissolved in 70 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8 g, 5 mmol) was added. After the reaction for 1 hour, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 1370 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl alcohol to prepare a white solid compound 11-c (48.6 g, 71%, MS: [M+H]+ = 409.5).
단계4) 화합물 11의 제조Step 4) Preparation of compound 11
질소 분위기에서 화합물 11-c(20 g, 49 mmol)와 4-페닐-9H-카바졸(11.9 g, 49 mmol)을 다이메틸포름아마이드 400 ml에 넣고 교반 및 환류하였다. 이 후 세슘카보네이트(47.9 g, 146.9 mmol)를 투입하고 가온 및 교반하였다. 3시간 반응 후 상온으로 식힌 후 생성된 고체를 여과하였다. 고체를 클로로포름 30 배 928 ml에 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸아세테이트를 이용하여 실리카 컬럼을 통해 정제하여 노란색의 고체 화합물 11(21.7g, 70%, MS: [M+H]+ = 632.8)을 제조하였다. In a nitrogen atmosphere, compound 11-c (20 g, 49 mmol) and 4-phenyl-9H-carbazole (11.9 g, 49 mmol) were added to 400 ml of dimethylformamide, followed by stirring and refluxing. After this, cesium carbonate (47.9 g, 146.9 mmol) was added, followed by heating and stirring. After reacting for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 30 times 928 ml of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 11 (21.7g, 70%, MS: [M+H]+ = 632.8).
제조예 12: 화합물 12의 제조Preparation Example 12: Preparation of compound 12
제조예 11에서, 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진 및 4-페닐-9H-카바졸 대신 9-(4-클로로-6-페닐-1,3,5-트리아진-2-일)-9H-카바졸 및 2-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 11의 제조 방법과 동일한 제조 방법으로 화합물 12를 제조하였다. (MS[M+H]
+= 760)In Preparation Example 11, 9-(4-chloro-6-phenyl- instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine and 4-phenyl-9H-carbazole- Compound 12 was prepared in the same manner as in the preparation method of Compound 11, except that 1,3,5-triazine-2-yl)-9H-carbazole and 2-phenyl-9H-carbazole were used. (MS[M+H] + = 760)
제조예 13: 화합물 13의 제조Preparation Example 13: Preparation of compound 13
제조예 11에서, 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진 및 4-페닐-9H-카바졸 대신 2-클로로-4,6-디페닐-1,3,5-트리아진 및 4-(디벤조[b,d]퓨란-2-일)-9H-카바졸을 사용한 것을 제외하고는, 화합물 11의 제조 방법과 동일한 제조 방법으로 화합물 13을 제조하였다. (MS[M+H]
+= 717)In Preparation Example 11, 2-chloro-4,6-diphenyl- instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine and 4-phenyl-9H-carbazole Except for using 1,3,5-triazine and 4-(dibenzo[b,d]furan-2-yl)-9H-carbazole, compound 13 was prepared in the same manner as in compound 11 Was prepared. (MS[M+H] + = 717)
제조예 14: 화합물 14의 제조Preparation Example 14: Preparation of compound 14
제조예 11에서, 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진 대신 2-(3-클로로페닐)-4-(디벤조[b,d]티오펜-4-일)-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는, 화합물 11의 제조 방법과 동일한 제조 방법으로 화합물 14를 제조하였다. (MS[M+H]
+= 809)In Preparation Example 11, 2-(3-chlorophenyl)-4-(dibenzo[b,d]ti instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine Compound 14 was prepared in the same manner as in the preparation method of Compound 11, except that ofen-4-yl)-6-phenyl-1,3,5-triazine was used. (MS[M+H] + = 809)
제조예 15: 화합물 15의 제조Preparation Example 15: Preparation of compound 15
제조예 11에서, 2-클로로-4-페닐-6-(페닐-d5)-1,3,5-트리아진 및 4-페닐-9H-카바졸 대신 2-클로로-4,6-디페닐-1,3,5-트리아진 및 3,6-디페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 11의 제조 방법과 동일한 제조 방법으로 화합물 15를 제조하였다. (MS[M+H]
+= 703)In Preparation Example 11, 2-chloro-4,6-diphenyl- instead of 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine and 4-phenyl-9H-carbazole Except for using 1,3,5-triazine and 3,6-diphenyl-9H-carbazole, compound 15 was prepared in the same manner as in the preparation method of compound 11. (MS[M+H] + = 703)
제조예 16: 화합물 16의 제조Preparation Example 16: Preparation of compound 16
단계 1) 화합물 16-a의 제조Step 1) Preparation of compound 16-a
질소 분위기에서 2-브로모-1-클로로-3-플루오로벤젠(50 g, 238.7 mmol)과 페닐 보론산(29.1 g, 238.7 mmol)을 테트라하이드로 퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(99 g, 716.2 mmol)를 물 99 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(8.3 g, 7.2 mmol)을 투입하였다. 3 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 987 ml에 투입하여 녹이고, 물로 2 회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올 재결정을 통해 흰색의 고체 화합물 16-a(29.6g, 60%, MS: [M+H]+ = 207.6)을 제조하였다.In a nitrogen atmosphere, 2-bromo-1-chloro-3-fluorobenzene (50 g, 238.7 mmol) and phenyl boronic acid (29.1 g, 238.7 mmol) were added to 1000 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (99 g, 716.2 mmol) was dissolved in 99 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (8.3 g, 7.2 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 987 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethyl alcohol to prepare a white solid compound 16-a (29.6g, 60%, MS: [M+H]+ = 207.6).
단계2) 화합물 16-b의 제조Step 2) Preparation of compound 16-b
질소 분위기에서 화합물 16-a(30 g, 145.2 mmol)와 비스(피나콜라토)디보론(36.9 g, 145.2 mmol)를 Diox 600 ml에 넣고 교반 및 환류하였다. 이 후 칼륨아세테이트(92.5 g, 435.5 mmol)을 투입하고 충분히 교반한 후 Pd(dba)
2(2.5 g, 4.4 mmol) 및 트리시클로헥실포스핀(2.4 g, 8.7 mmol) 을 투입하였다. 7 시간 반응 후 상온으로 식힌 후 유기층을 필터처리하여 염을 제거 한 후 걸러진 유기층을 증류하였다. 이를 다시 클로로포름 10 배 433 ml에 투입하여 녹이고, 물로 2 회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에탄올 재결정을 통해 흰색의 고체 화합물 16-b(33.3 g, 77 %, MS: [M+H]+ = 299.2)을 제조하였다.In a nitrogen atmosphere, compound 16-a (30 g, 145.2 mmol) and bis (pinacolato) diboron (36.9 g, 145.2 mmol) were added to 600 ml of Diox and stirred and refluxed. Thereafter, potassium acetate (92.5 g, 435.5 mmol) was added, stirred sufficiently, and then Pd(dba) 2 (2.5 g, 4.4 mmol) and tricyclohexylphosphine (2.4 g, 8.7 mmol) were added. After reacting for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 433 ml of 10 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare a white solid compound 16-b (33.3 g, 77%, MS: [M+H]+ = 299.2).
단계3) 화합물 1-c의 제조Step 3) Preparation of compound 1-c
질소 분위기에서 화합물 16-b(50 g, 167.7 mmol)와 2-클로로-4,6-디페닐-1,3,5-트리아진(44.9 g, 167.7 mmol)을 테트라하이드로 퓨란 1000 ml에 넣고 교반 및 환류하였다. 이 후 포타슘카보네이트(69.5 g, 503.1 mmol)를 물 70 ml에 녹여 투입하고 충분히 교반한 후 테트라키스(트리페닐포스핀)팔라듐(5.8 g, 5 mmol)을 투입하였다. 2 시간 반응 후 상온으로 식힌 후 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름 20 배 1353 ml에 투입하여 녹이고, 물로 2 회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸알코올 재결정을 통해 흰색의 고체 화합물 16-c(52.1 g, 77 %, MS: [M+H]+ = 404.5)을 제조하였다.In a nitrogen atmosphere, compound 16-b (50 g, 167.7 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (44.9 g, 167.7 mmol) were added to 1000 ml of tetrahydrofuran and stirred. And refluxed. Thereafter, potassium carbonate (69.5 g, 503.1 mmol) was dissolved in 70 ml of water, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (5.8 g, 5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again added to 1353 ml of 20 times chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized in chloroform and ethyl alcohol to prepare a white solid compound 16-c (52.1 g, 77%, MS: [M+H]+ = 404.5).
단계4) 화합물 16의 제조Step 4) Preparation of compound 16
질소 분위기에서 화합물 16-c(20 g, 49.6 mmol)와 2-페닐-9H-카바졸(12.1 g, 49.6 mmol)을 다이메틸포름아마이드 400 ml에 넣고 교반 및 환류하였다. 이 후 세슘카보네이트(48.5 g, 148.7 mmol)를 투입하고 가온 및 교반하였다. 3시간 반응 후 상온으로 식힌 후 생성된 고체를 여과하였다. 고체를 클로로포름 30 배 932 ml에 투입하여 녹이고, 물로 2 회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 클로로포름과 에틸아세테이트를 이용하여 실리카 컬럼을 통해 정제하여 노란색의 고체 화합물 16(23 g, 74 %, MS: [M+H]+ = 627.8)을 제조하였다.In a nitrogen atmosphere, compound 16-c (20 g, 49.6 mmol) and 2-phenyl-9H-carbazole (12.1 g, 49.6 mmol) were added to 400 ml of dimethylformamide, followed by stirring and refluxing. After this, cesium carbonate (48.5 g, 148.7 mmol) was added, followed by heating and stirring. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature. The solid was added to 30 times 932 ml of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a yellow solid compound 16 (23 g, 74%, MS: [M+H]+ = 627.8).
제조예 17: 화합물 17의 제조Preparation Example 17: Preparation of compound 17
제조예 16에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 2-페닐-9H-카바졸 대신 2-클로로-4-(디벤조[b,d]티오펜-4-일)-6-페닐-1,3,5-트리아진 및 4-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 16의 제조 방법과 동일한 제조 방법으로 화합물 17를 제조하였다. (MS[M+H]
+= 733)In Preparation Example 16, 2-chloro-4-(dibenzo[b,d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 2-phenyl-9H-carbazole Compound 17 was prepared in the same manner as in the preparation method of compound 16, except that -4-yl)-6-phenyl-1,3,5-triazine and 4-phenyl-9H-carbazole were used. (MS[M+H] + = 733)
제조예 18: 화합물 18의 제조Preparation Example 18: Preparation of compound 18
제조예 16에서, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 2-페닐-9H-카바졸 대신 2-(3-클로로페닐)-4,6-디페닐-1,3,5-트리아진 및 3-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 16의 제조 방법과 동일한 제조 방법으로 화합물 18를 제조하였다. (MS[M+H]
+= 703)In Preparation Example 16, 2-(3-chlorophenyl)-4,6-diphenyl- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and 2-phenyl-9H-carbazole Compound 18 was prepared in the same manner as in the preparation method of Compound 16, except that 1,3,5-triazine and 3-phenyl-9H-carbazole were used. (MS[M+H] + = 703)
제조예 19: 화합물 19의 제조Preparation Example 19: Preparation of compound 19
제조예 16에서, 2-페닐-9H-카바졸 대신 4-(페닐-d5)-9H-카바졸을 사용한 것을 제외하고는, 화합물 16의 제조 방법과 동일한 제조 방법으로 화합물 19를 제조하였다. (MS[M+H]
+= 632)In Preparation Example 16, compound 19 was prepared in the same manner as in the preparation method of Compound 16, except that 4-(phenyl-d5)-9H-carbazole was used instead of 2-phenyl-9H-carbazole. (MS[M+H] + = 632)
제조예 20: 화합물 20의 제조Preparation Example 20: Preparation of compound 20
제조예 16에서, 페닐 보론산, 2-클로로-4,6-디페닐-1,3,5-트리아진 및 2-페닐-9H-카바졸 대신 (4-(디벤조[b,d]티오펜-4-일)페닐)보론산, 2-(4-클로로페닐)-4,6-디페닐-1,3,5-트리아진 및 4-페닐-9H-카바졸을 사용한 것을 제외하고는, 화합물 16의 제조 방법과 동일한 제조 방법으로 화합물 20를 제조하였다. (MS[M+H]
+= 885)In Preparation Example 16, instead of phenyl boronic acid, 2-chloro-4,6-diphenyl-1,3,5-triazine and 2-phenyl-9H-carbazole, (4-(dibenzo[b,d]ti Except for the use of ofen-4-yl)phenyl)boronic acid, 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 4-phenyl-9H-carbazole , Compound 20 was prepared in the same manner as in the preparation method of compound 16. (MS[M+H] + = 885)
실시예 1Example 1
ITO(Indium Tin Oxide)가 1400 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of 1400 Å of ITO (Indium Tin Oxide) was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에, 하기 화합물 HT-A와 하기 화합물 PD를 95:5의 중량비로 100 Å의 두께로 열 진공 증착하고, 이어서 하기 화합물 HT-A만 1150 Å의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에, 하기 화합물 HT-B를 450 Å의 두께로 열 진공 증착하여 전자차단층을 형성하였다. 상기 전자차단층 위에, 앞서 제조한 화합물 1과 하기 화합물 GD를 85:15의 중량비로 400 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 위에, 하기 화합물 ET-A를 50 Å의 두께로 진공 증착하여 정공저지층을 형성하였다. 상기 정공저지층 위에, 하기 화합물 ET-B와 하기 화합물 Liq를 2:1의 중량비로 250 Å의 두께로 열 진공 증착하고, 이어서 LiF와 마그네슘을 1:1의 중량비로 30 Å의 두께로 진공 증착하여 전자 수송 및 주입층을 형성하였다. 상기 전자주입층 위에, 마그네슘과 은을 1:4의 중량비로 160 Å의 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.On the thus prepared ITO transparent electrode, the following compound HT-A and the following compound PD were thermally vacuum deposited to a thickness of 100 Å at a weight ratio of 95:5, and then only the following compound HT-A was deposited to a thickness of 1150 Å to form a hole transport layer. Formed. On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 450 Å to form an electron blocking layer. On the electron blocking layer, a light emitting layer was formed by vacuum deposition of Compound 1 prepared above and Compound GD below to a thickness of 400 Å at a weight ratio of 85:15. On the light emitting layer, the following compound ET-A was vacuum deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound Liq were thermally vacuum deposited to a thickness of 250 Å at a weight ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 Å at a weight ratio of 1:1. Thus, an electron transport and injection layer was formed. On the electron injection layer, magnesium and silver were deposited to a thickness of 160 Å in a weight ratio of 1:4 to form a cathode, thereby manufacturing an organic light emitting device.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 은과 마그네슘은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2*10
-7 ~ 5*10
-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 Å/sec, and the deposition rate of silver and magnesium was 2 Å/sec. Maintaining *10 -7 ~ 5 *10 -6 torr, an organic light emitting device was manufactured.
실시예 2 내지 25 및 비교예 1 내지 11Examples 2 to 25 and Comparative Examples 1 to 11
상기 실시예 1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in Example 1.
참고로, 실시예 21 내지 25 및 비교예 9 내지 11에서는 화합물 1 대신 하기 표 1에 기재된 화합물을 1:1의 중량비로 사용하여 유기 발광 소자를 제작하였다. 실시예 21을 예로 들면, 실시예 1에서 화합물 1 대신 화합물 2 및 화합물 H-2를 1:1의 중량비로 사용한 것이다. 하기 표 1에서, 화합물 H-2, C1 내지 C8은 각각 아래와 같다.For reference, in Examples 21 to 25 and Comparative Examples 9 to 11, an organic light-emitting device was manufactured by using the compound shown in Table 1 below in a weight ratio of 1:1 instead of Compound 1. Taking Example 21 as an example, instead of Compound 1 in Example 1, Compound 2 and Compound H-2 were used in a weight ratio of 1:1. In Table 1 below, compounds H-2 and C1 to C8 are as follows, respectively.
실험예 Experimental example
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하여 전압, 효율, 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 전압 및 효율은 10 mA/cm
2의 전류 밀도를 인가하여 측정하였다. 또한, 하기 표 1의 T95는 전류 밀도 20 mA/cm
2에서 초기 휘도가 95%로 저하할 때까지 측정한 시간을 의미한다.Voltage, efficiency, and lifetime (T95) were measured by applying a current to the organic light-emitting devices manufactured in the above Examples and Comparative Examples, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
구분division | 발광층 화합물Emission layer compound | 전압(V)(@10mA/cm 2)Voltage(V)(@10mA/cm 2 ) | 효율(cd/A)(@10mA/cm 2)Efficiency (cd/A)(@10mA/cm 2 ) | 발광색Luminous color | T95(hr)(@20mA/cm 2)T95(hr)(@20mA/cm 2 ) |
실시예 1Example 1 | 화합물 1Compound 1 | 3.013.01 | 65.965.9 | 녹 색green | 7777 |
실시예 2Example 2 | 화합물 2Compound 2 | 3.003.00 | 65.865.8 | 녹 색green | 8787 |
실시예 3Example 3 | 화합물 3Compound 3 | 3.063.06 | 66.166.1 | 녹 색green | 8585 |
실시예 4Example 4 | 화합물 4Compound 4 | 2.972.97 | 67.267.2 | 녹 색green | 7272 |
실시예 5Example 5 | 화합물 5Compound 5 | 3.003.00 | 66.366.3 | 녹 색green | 8080 |
실시예 6Example 6 | 화합물 6Compound 6 | 3.063.06 | 66.166.1 | 녹 색green | 8080 |
실시예 7Example 7 | 화합물 7Compound 7 | 3.023.02 | 66.866.8 | 녹 색green | 7070 |
실시예 8Example 8 | 화합물 8Compound 8 | 2.982.98 | 66.366.3 | 녹 색green | 7575 |
실시예 9Example 9 | 화합물 9Compound 9 | 3.013.01 | 67.067.0 | 녹 색green | 7272 |
실시예 10Example 10 | 화합물 10Compound 10 | 3.033.03 | 65.565.5 | 녹 색green | 7878 |
실시예 11Example 11 | 화합물 11Compound 11 | 3.023.02 | 65.265.2 | 녹 색green | 7171 |
실시예 12Example 12 | 화합물 12Compound 12 | 3.003.00 | 62.062.0 | 녹 색green | 7979 |
실시예 13Example 13 | 화합물 13Compound 13 | 2.982.98 | 67.067.0 | 녹 색green | 7474 |
실시예 14Example 14 | 화합물 14Compound 14 | 3.053.05 | 67.167.1 | 녹 색green | 7575 |
실시예 15Example 15 | 화합물 15Compound 15 | 3.093.09 | 66.066.0 | 녹 색green | 7878 |
실시예 16Example 16 | 화합물 16Compound 16 | 3.103.10 | 65.065.0 | 녹 색green | 7272 |
실시예 17Example 17 | 화합물 17Compound 17 | 3.123.12 | 65.765.7 | 녹 색green | 7373 |
실시예 18Example 18 | 화합물 18Compound 18 | 3.153.15 | 64.864.8 | 녹 색green | 7171 |
실시예 19Example 19 | 화합물 19Compound 19 | 3.113.11 | 65.365.3 | 녹 색green | 8282 |
실시예 20Example 20 | 화합물 20Compound 20 | 3.203.20 | 64.064.0 | 녹 색green | 7575 |
실시예 21Example 21 | 화합물 2, 화합물 H-2Compound 2, Compound H-2 | 3.113.11 | 70.070.0 | 녹 색green | 8585 |
실시예 22Example 22 | 화합물 4, 화합물 H-2Compound 4, Compound H-2 | 3.173.17 | 68.368.3 | 녹 색green | 9595 |
실시예 23Example 23 | 화합물 8, 화합물 H-2Compound 8, Compound H-2 | 3.123.12 | 69.169.1 | 녹 색green | 8282 |
실시예 24Example 24 | 화합물 15, 화합물 H-2Compound 15, Compound H-2 | 3.183.18 | 68.268.2 | 녹 색green | 8888 |
실시예 25Example 25 | 화합물 17 화합물 H-2Compound 17 Compound H-2 | 3.253.25 | 69.069.0 | 녹 색green | 8686 |
비교예 1Comparative Example 1 | 화합물 C1Compound C1 | 3.013.01 | 65.565.5 | 녹 색green | 6565 |
비교예 2Comparative Example 2 | 화합물 C2Compound C2 | 3.123.12 | 64.064.0 | 녹 색green | 7070 |
비교예 3Comparative Example 3 | 화합물 C3Compound C3 | 3.123.12 | 65.165.1 | 녹 색green | 6666 |
비교예 4Comparative Example 4 | 화합물 C4Compound C4 | 3.253.25 | 66.066.0 | 녹 색green | 7171 |
비교예 5Comparative Example 5 | 화합물 C5Compound C5 | 3.213.21 | 67.067.0 | 녹 색green | 5858 |
비교예 6Comparative Example 6 | 화합물 C6Compound C6 | 3.193.19 | 59.159.1 | 녹 색green | 5555 |
비교예 7Comparative Example 7 | 화합물 C7Compound C7 | 3.223.22 | 45.245.2 | 녹 색green | 5151 |
비교예 8Comparative Example 8 | 화합물 C8Compound C8 | 3.153.15 | 57.257.2 | 녹 색green | 6060 |
비교예 9Comparative Example 9 | 화합물 C1, 화합물 H-2Compound C1, Compound H-2 | 3.123.12 | 67.567.5 | 녹 색green | 7676 |
비교예 10Comparative Example 10 | 화합물 C3, 화합물 H-2Compound C3, Compound H-2 | 3.203.20 | 68.268.2 | 녹 색green | 7272 |
비교예 11Comparative Example 11 | 화합물 C6, 화합물 H-2Compound C6, Compound H-2 | 3.253.25 | 61.861.8 | 녹 색green | 6060 |
본 발명에 따른 화합물은 카바졸의 오쏘 위치에 아릴기가 치환되어 구조적 뒤틀림이 발생하고, 이로 인해 charge transfer가 잘 이루어질 수 있다. 이로 인해 분자의 안정성이 높고, 정공과 전자 수송에 모두 유리할 것으로 추측된다. 또한, 본 발명 화학식 1의 모체에 다양한 아릴기 및 헤테로아릴이 추가로 치환되어 전자 수송 특성을 다양하게 조절할 수 있어 공통층의 변경에 따른 전하 균형을 맞추는데 유리할 것으로 예상된다.In the compound according to the present invention, structural distortion occurs due to substitution of an aryl group at the ortho position of carbazole, and thus charge transfer can be performed well. For this reason, the stability of the molecule is high, and it is presumed to be advantageous for both hole and electron transport. In addition, since various aryl groups and heteroaryls are additionally substituted in the parent body of the present invention, the electron transport properties can be variously adjusted, and thus it is expected to be advantageous in balancing charge according to the change of the common layer.
상기 표 1에서, 실시예 1 내지 20과 비교예 1 내지 8은 발광층에 단독 호스트를 사용한 유기 발광 소자의 예이고, 실시예 21 내지 25와 비교예 9 내지 11은 발광층에 2종의 호스트를 사용한 소자예이다. 발광층에 1 종의 호스트를 사용하는 경우뿐만 아니라, 2 종의 호스트를 사용하는 경우에도, 본 발명의 화합물을 사용한 실시예의 유기 발광 소자가 비교예의 유기 발광 소자에 비하여 효율이 보다 높고, 구동 전압이 낮으며, 특히 수명 특성이 크게 향상되는 것을 확인할 수 있었다.In Table 1, Examples 1 to 20 and Comparative Examples 1 to 8 are examples of organic light emitting devices using a single host for the emission layer, and Examples 21 to 25 and Comparative Examples 9 to 11 use two types of hosts for the emission layer. This is an example of a device. In the case of using one type of host for the emission layer, as well as when using two types of hosts, the organic light-emitting device of the Example using the compound of the present invention has higher efficiency and higher driving voltage than the organic light-emitting device of Comparative Example. It was confirmed that it was low, and in particular, the life characteristics were greatly improved.
따라서 상기 표 1에 나타난 바와 같이, 화학식 1의 화합물을 유기발광소자의 호스트로서 사용할 경우, 저전압, 고효율, 장수명의 특성이 나타남을 확인할 수 있었다. Therefore, as shown in Table 1, when the compound of Formula 1 was used as a host of an organic light emitting device, it was confirmed that the characteristics of low voltage, high efficiency, and long life were exhibited.
부호의 설명Explanation of sign
1: 기판 2: 양극1: substrate 2: anode
3: 발광층 4: 음극3: light emitting layer 4: cathode
5: 정공주입층 6: 정공수송층5: hole injection layer 6: hole transport layer
7: 전자차단층 8: 정공저지층7: electron blocking layer 8: hole blocking layer
9: 전자수송층 10: 전자주입층9: electron transport layer 10: electron injection layer
Claims (9)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]상기 화학식 1에서,In Formula 1,L은 1번 탄소, 2번 탄소, 또는 3번 탄소에 연결되고,L is connected to carbon 1, carbon 2, or carbon 3,L은 단일결합; 또는 치환 또는 비치환된 C 6-60 아릴렌이고,L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,Ar 1 및 Ar 2는 각각 독립적으로, 치환 또는 비치환된 C 6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C 2-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,R 1은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C 6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C 2-60 헤테로아릴이고,Each R 1 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,R 2는 각각 독립적으로 치환 또는 비치환된 C 6-60 아릴, 벤조퓨라닐, 벤조티오페닐, 디벤조퓨라닐, 또는 페닐 벤조티오페닐이고,R 2 is each independently substituted or unsubstituted C 6-60 aryl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or phenyl benzothiophenyl,p는 0 내지 5인 정수이고,p is an integer from 0 to 5,q는 1 내지 8인 정수이다.q is an integer from 1 to 8.
- 제1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-3으로 표시되는,Formula 1 is represented by the following Formulas 1-1 to 1-3,화합물:compound:[화학식 1-1][Formula 1-1][화학식 1-2][Formula 1-2][화학식 1-3][Formula 1-3]상기 화학식 1-1 내지 화학식 1-3에서,In Formulas 1-1 to 1-3,L, Ar 1, Ar 2, R 1, R 2, p 및 q에 대한 설명은 제1항에서 정의한 바와 같다.The description of L, Ar 1 , Ar 2 , R 1 , R 2 , p and q is as defined in claim 1.
- 제1항에 있어서,The method of claim 1,L은 단일결합, 페닐렌, 또는 나프틸렌인,L is a single bond, phenylene, or naphthylene,화합물.compound.
- 제1항에 있어서,The method of claim 1,Ar 1 및 Ar 2는 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 카바졸릴, 디벤조퓨라닐, 디벤조티오페닐, 5개의 중수소로 치환된 페닐, 카바졸릴 페닐, 또는 페닐 벤조티오페닐인,Ar 1 and Ar 2 are each independently phenyl, biphenylyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenyl substituted with five deuteriums, carbazolyl phenyl, or phenyl benzothiophenyl. ,화합물.compound.
- 제1항에 있어서,The method of claim 1,R 1은 수소, 중수소, 페닐, 카바졸릴, 디벤조퓨라닐, 또는 디벤조티오페닐인,R 1 is hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,화합물.compound.
- 제1항에 있어서,The method of claim 1,q는 1 또는 2인,q is 1 or 2,화합물.compound.
- 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 제1항 내지 제8항 중 어느 하나의 항에 따른 화합물을 포함하는, A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 8. doing,유기 발광 소자.Organic light emitting device.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202080006172.3A CN113039183B (en) | 2019-06-27 | 2020-06-12 | Novel compound and organic light emitting device comprising the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2019-0077351 | 2019-06-27 | ||
KR20190077351 | 2019-06-27 | ||
KR10-2020-0069692 | 2020-06-09 | ||
KR1020200069692A KR102447007B1 (en) | 2019-06-27 | 2020-06-09 | Novel compound and organic light emitting device comprising the same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2020262861A1 true WO2020262861A1 (en) | 2020-12-30 |
Family
ID=74061761
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2020/007634 WO2020262861A1 (en) | 2019-06-27 | 2020-06-12 | Novel compound and organic light emitting device comprising same |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2020262861A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022177404A1 (en) * | 2021-02-22 | 2022-08-25 | 주식회사 엘지화학 | Novel compound, and organic light-emitting device using same |
EP4335846A1 (en) | 2022-06-30 | 2024-03-13 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
WO2024101869A1 (en) * | 2022-11-09 | 2024-05-16 | 주식회사 엘지화학 | Novel compound and organic light-emitting device comprising same |
GB2625904A (en) * | 2022-12-22 | 2024-07-03 | Lg Display Co Ltd | Organic compound, organic light emitting diode and organic light emitting device having the compound |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130130236A (en) * | 2011-05-03 | 2013-12-02 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
KR20170049291A (en) * | 2015-10-28 | 2017-05-10 | 희성소재 (주) | Hetero-cyclic compound and organic light emitting device using the same |
KR20180098809A (en) * | 2017-02-27 | 2018-09-05 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device comprising the same |
KR20190028591A (en) * | 2017-09-08 | 2019-03-19 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
WO2019101594A1 (en) * | 2017-11-21 | 2019-05-31 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
-
2020
- 2020-06-12 WO PCT/KR2020/007634 patent/WO2020262861A1/en active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130130236A (en) * | 2011-05-03 | 2013-12-02 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
KR20170049291A (en) * | 2015-10-28 | 2017-05-10 | 희성소재 (주) | Hetero-cyclic compound and organic light emitting device using the same |
KR20180098809A (en) * | 2017-02-27 | 2018-09-05 | 삼성전자주식회사 | Condensed cyclic compound and organic light emitting device comprising the same |
KR20190028591A (en) * | 2017-09-08 | 2019-03-19 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
WO2019101594A1 (en) * | 2017-11-21 | 2019-05-31 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022177404A1 (en) * | 2021-02-22 | 2022-08-25 | 주식회사 엘지화학 | Novel compound, and organic light-emitting device using same |
EP4335846A1 (en) | 2022-06-30 | 2024-03-13 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device thereof |
WO2024101869A1 (en) * | 2022-11-09 | 2024-05-16 | 주식회사 엘지화학 | Novel compound and organic light-emitting device comprising same |
GB2625904A (en) * | 2022-12-22 | 2024-07-03 | Lg Display Co Ltd | Organic compound, organic light emitting diode and organic light emitting device having the compound |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2017204594A1 (en) | Organic light emitting element | |
WO2020262861A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2021125648A1 (en) | Novel compound, and organic light-emitting element using same | |
WO2022102992A1 (en) | Novel compound and organic light-emitting device using same | |
WO2021080253A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2020231242A1 (en) | Organic light-emitting element | |
WO2023096405A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2022235101A1 (en) | Organic light emitting device | |
WO2022059923A1 (en) | Novel compound and organic light-emitting device comprising same | |
WO2022031020A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2022031013A1 (en) | Novel compound and organic light-emitting device comprising same | |
WO2022031016A1 (en) | Novel compound and organic light-emitting device using same | |
WO2021034156A1 (en) | Novel compound and organic light emitting device using same | |
WO2021040467A1 (en) | Novel heterocyclic compound and organic light-emitting device using same | |
WO2021149954A1 (en) | Organic light emitting device | |
WO2020246835A1 (en) | Novel compound and organic light-emitting device using same | |
WO2020246837A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2020231021A1 (en) | Organic light emitting device | |
WO2020185038A1 (en) | Novel compound and organic light emitting device using same | |
WO2020197170A1 (en) | Novel compound and organic light emitting device comprising the same | |
WO2020235955A1 (en) | Novel compound and organic light-emitting device using same | |
WO2020242161A1 (en) | Novel compound and organic light emitting device using same | |
WO2024101869A1 (en) | Novel compound and organic light-emitting device comprising same | |
WO2022191681A1 (en) | Novel compound and organic light emitting device comprising same | |
WO2022014857A1 (en) | Novel compound and organic light-emitting element comprising same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20833410 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 20833410 Country of ref document: EP Kind code of ref document: A1 |