CN117279918A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN117279918A CN117279918A CN202280032230.9A CN202280032230A CN117279918A CN 117279918 A CN117279918 A CN 117279918A CN 202280032230 A CN202280032230 A CN 202280032230A CN 117279918 A CN117279918 A CN 117279918A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 150
- 239000010410 layer Substances 0.000 claims description 146
- 239000012044 organic layer Substances 0.000 claims description 108
- -1 phenylnaphthyl Chemical group 0.000 claims description 66
- 239000000126 substance Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 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 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 229920001225 polyester resin Polymers 0.000 claims 2
- 239000004645 polyester resin Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 82
- 239000000203 mixture Substances 0.000 description 68
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 66
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 64
- 238000003756 stirring Methods 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 41
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 239000000706 filtrate Substances 0.000 description 38
- 238000002347 injection Methods 0.000 description 38
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- 238000010898 silica gel chromatography Methods 0.000 description 38
- 238000001914 filtration Methods 0.000 description 34
- 229910000027 potassium carbonate Inorganic materials 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- 230000032258 transport Effects 0.000 description 25
- 230000000903 blocking effect Effects 0.000 description 23
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- 125000004432 carbon atom Chemical group C* 0.000 description 20
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- 238000000034 method Methods 0.000 description 13
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- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 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 4
- 239000010406 cathode material Substances 0.000 description 4
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- 239000012153 distilled water Substances 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- XYIVDCIQMQLOGI-UHFFFAOYSA-N (4-methoxyquinolin-3-yl)boronic acid Chemical compound COC1=C(C=NC2=CC=CC=C12)B(O)O XYIVDCIQMQLOGI-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 230000000694 effects 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
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- JHHMLFBYFNAPDZ-UHFFFAOYSA-N 2-bromo-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1Br JHHMLFBYFNAPDZ-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CNOIGNSHTUNNGC-UHFFFAOYSA-N 3-bromo-4-chloropyridin-2-amine Chemical compound NC1=NC=CC(Cl)=C1Br CNOIGNSHTUNNGC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
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- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- 238000013508 migration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- 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 1
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- 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 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
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
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- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-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
- 239000011368 organic material Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-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
- 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 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
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 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 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 230000007704 transition Effects 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YGUPAQDKOAPZHC-UHFFFAOYSA-N tricyclohexylphosphane Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 YGUPAQDKOAPZHC-UHFFFAOYSA-N 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
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides novel compounds and organic light emitting devices comprising the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2021-0155894 at 11.12 of 2021 and korean patent application No. 10-2022-0148521 at 11.9 of 2022, the entire contents of the disclosures of which are incorporated herein as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 to X 9 Each independently is N or CR 1 And X is 1 To X 9 At least one of which is N,
R 1 is hydrogen; deuterium; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
l are each independently a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by 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 injection and transport layer 9, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in the heterocyclic group containing 1 or more of S atoms is substituted or unsubstituted, or a substituent bonded by 2 or more substituents in the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the substituent may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may be a substituent of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the substituent may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are 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 the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of a heterocyclic group can be applied thereto.
(Compound)
The present invention provides a compound represented by the above chemical formula 1.
Preferably X 1 To X 9 One of which is N.
Preferably, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-9:
in the above chemical formulas 1-1 to 1-9,
X 1 to X 9 、R 1 、L、Ar 1 And Ar is a group 2 As in the case of the definition set forth above,
n is an integer from 1 to 8.
Preferably, R 1 Hydrogen or deuterium.
Preferably, L is a single bond, phenylene or naphthylene, which are unsubstituted or substituted with one or more deuterium.
Preferably, L is a single bond or any one selected from the following groups:
preferably Ar 1 And Ar is a group 2 Each independently is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, carbazol-9-yl, benzophenanthryl orRadical, ar as described above 1 And Ar is a group 2 Unsubstituted or substituted with one or more deuterium.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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the present invention also provides a method for producing a compound represented by the above chemical formula 1, which is represented by the following chemical formula 1.
[ reaction type 1]
In the above reaction formula 1, Y is halogen, preferably bromine or chlorine, as defined above except Y.
The above reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the above reaction may be modified according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
(organic light-emitting device)
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic 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 layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1. In particular, the compounds according to the invention can be used as dopants for light-emitting layers.
The organic layer may include an electron transport layer, an electron injection layer, or a layer that performs electron transport and electron injection at the same time, and the electron transport layer, the electron injection layer, or the layer that performs electron transport and electron injection at the same time may include the compound represented by chemical formula 1.
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, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by 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 injection and transport layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, and lithiumMetals such as gadolinium, aluminum, silver, tin and lead or alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The electron blocking layer refers to the following layers: the hole transport layer is preferably formed so as to be in contact with the light-emitting layer, and the hole mobility is adjusted to prevent excessive migration of electrons, thereby increasing the probability of hole-electron bonding and improving the efficiency of the organic light-emitting device. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, an arylamine-based organic material or the like can be used, but the electron blocking material is not limited thereto.
The light-emitting material is capable of receiving holes and electrons from the hole transport layer and the electron transport layer, respectivelyThe substance that emits light in the visible light region by combining electrons is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto. />
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. Furthermore, as a means of The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The hole blocking layer refers to the following layer: the organic light-emitting layer is preferably formed on the light-emitting layer so as to be in contact with the light-emitting layer, and the electron mobility is adjusted to prevent excessive migration of holes and to increase the probability of hole-electron bonding, thereby improving the efficiency of the organic light-emitting layer device. The hole blocking layer contains a hole blocking substance, and as an example of such a hole blocking substance, triazine derivatives, triazole derivatives, triazine derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from an electrode and transports the received electrons to a light emitting layer and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high electron mobility. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) with (c), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->The compounds are used together with a derivative thereof, a metal complex, a nitrogen-containing five-membered ring derivative, or the like, but are not limited thereto.
The electron injection and transport layer may also beFormed as separate layers such as an electron injection layer and an electron transport layer. In this case, an electron transporting layer is formed over the light emitting layer or the hole blocking layer, and as an electron transporting substance contained in the electron transporting layer, the above-described electron injecting and transporting substance can be used. Further, an electron injection layer is formed on the electron transport layer, and LiF, naCl, csF, li can be used as an electron injection substance contained in the electron injection layer 2 O, baO fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-hydroxyquinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-hydroxyquinoline) (1-naphthol), gallium bis (2-methyl-8-hydroxyquinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound according to the present invention may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Examples (example)
Production example 1
3-bromo-4-chloropyridin-2-amine (3-bromo4-chloropyridin-2-amine) (15 g,72.3 mmol) and (1-methoxynaphthalen-2-yl) boronic acid ((1-methoxynaphthalen-2-yl) acrylic acid) (15.3 g,75.9 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (potassium carbonate) (30 g,216.9 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-tert-butylphosphine) palladium (0) (bis (tris-tert-butylphosphine) palladium (0)) (0.4 g,0.7 mmol) was poured. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 12.7g of compound A-1_P1 was produced. (yield 62%, MS: [ M+H) ] + ＝285)
Compound A-1_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of Acetonitrile (Acetonitile) and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 9 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After dissolving in chloroform and washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the filtrate was filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8g of compound A-1_P2 was produced. (yield 60%, MS: [ M+H)] + ＝254)
Compound A-1_P2 (15 g,59.1 mmol) and bis (pinacolato) diboron (bis (pinacolato) diboron) (16.5 g,65 mmol) were combined in 300ml of 1,4-diThe mixture was refluxed and stirred in alkane (1, 4-dioxane). Then, potassium acetate (potassium acetate) (8.7 g,88.7 mm)Mol), bis (dibenzylideneacetone) palladium (0) (bis (dibenzylideneacetone) palladium (0)) (1 g,1.8 mmol) and tricyclohexylphosphine (tricyclohexylphosphine) (1 g,3.5 mmol) were charged after stirring thoroughly. After the reaction was carried out for 6 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water by chloroform and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.1g of compound A-1 was produced. (yield 79%, MS: [ M+H) ] + ＝346)
Production example 2
Compound a-2 was produced by the same method as in production example 1, except that 4-bromo-5-chloropyridin-3-amine (4-bromo5-chloropyrindin-3-amine) was used instead of 3-bromo-4-chloropyridin-2-amine.
Production example 3
Compound a-3 was produced by the same method as in production example 1, except that 3-bromo-2-chloropyridin-4-amine (3-bromo2-chloropyrindin-4-amine) was used instead of 3-bromo-4-chloropyridin-2-amine.
Production example 4
2-bromo-3-chloroaniline (2-bromoo-3-chloroaniline) (15 g,72.6 mmol) and (4-methoxyquinolin-3-yl) boronic acid ((4-methoxyquinolin-3-yl) acrylic acid) (15.5 g,76.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (30.1 g,217.9 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.7 mmol) was added thereto. After 4 hours of reaction, cool to normalAfter separating the organic layer and the aqueous layer, the organic layer was distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14g of compound B-1_P1 was produced. (yield 68%, MS: [ M+H) ] + ＝285)
Compound B-1_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After the reaction for 8 hours, the temperature was raised to room temperature, and 300ml of water was added thereto for dilution. After dissolving in chloroform and washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the filtrate was filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 6.8g of compound B-1_P2 was produced. (yield 51%, MS: [ M+H ]] + ＝254)
Compound B-1_P2 (15 g,59.1 mmol) and bis (pinacolato) diboron (16.5 g,65 mmol) were combined in 300ml of 1, 4-bisReflux and stirring the mixture in the alkane. Then, potassium acetate (8.7 g,88.7 mmol) was charged, and after stirring thoroughly, bis (dibenzylideneacetone) palladium (0) (1 g,1.8 mmol) and tricyclohexylphosphine (1 g,3.5 mmol) were charged. The reaction was carried out for 5 hours, cooled to room temperature, and the organic layer was separated from the water using chloroform and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.9g of compound B-1 was produced. (yield 68%, MS: [ M+H) ] + ＝346)
Production example 5
Compound B-2 was produced by the same method as in production example 4, except that (4-methoxyisoquinolin-3-yl) boronic acid (4-methoxyisoquinolin-3-yl) was used instead of (4-methoxyquinolin-3-yl) boronic acid.
Production example 6
Compound B-3 was produced in the same manner as in production example 4, except that (5-methoxyquinolin-6-yl) boric acid ((5-methoxyquinolin-6-yl) boric acid) was used instead of (4-methoxyquinolin-3-yl) boric acid.
PREPARATION EXAMPLE 7
Compound B-4 was produced by the same method as in production example 4, except that (5-methoxyisoquinolin-6-yl) boronic acid (5-methoxyisoquinolin-6-yl) was used instead of (4-methoxyquinolin-3-yl) boronic acid.
Production example 8
Compound B-5 was produced by the same method as in production example 4, except that (8-methoxyisoquinolin-7-yl) boronic acid (8-methoxyisoquinolin-7-yl) was used instead of (4-methoxyquinolin-3-yl) boronic acid.
Production example 9
2-bromo-3-chloroaniline (2-bromoo-3-chloroaniline) (15 g,72.6 mmol) and (8-methoxyquinolin-7-yl) boronic acid ((8-methoxyquinolin-7-yl) were added to 300ml of THF (15.5 g,76.3 mmol), stirred and refluxed. Then, potassium carbonate (30.1 g,217.9 mmol) was dissolved in 100ml of water and added thereto, followed by stirring thoroughly After that, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.7 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.1g of compound B-6_P1 was produced. (yield 73%, MS: [ M+H)] + ＝285)
Compound B-6_P1 (15 g,52.7 mmol) and HBF 4 (9.3 g,105.4 mmol) was added to 150ml of acetonitrile and stirred. Then, naNO is added 2 (14.6 g,105.4 mmol) was dissolved in 30ml of water and added slowly at 0 ℃. After 9 hours of reaction, the temperature was raised to room temperature, and 300ml of water was added to dilute the mixture. After dissolving in chloroform and washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, the filtrate was filtered and distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.9g of compound B-6_P2 was produced. (yield 59%, MS: [ M+H)] + ＝254)
Compound B-6_P2 (15 g,59.1 mmol) and bis (pinacolato) diboron (16.5 g,65 mmol) were combined in 300ml of 1, 4-diReflux and stirring the mixture in the alkane. Then, potassium acetate (8.7 g,88.7 mmol) was charged, and after stirring thoroughly, bis (dibenzylideneacetone) palladium (0) (1 g,1.8 mmol) and tricyclohexylphosphine (1 g,3.5 mmol) were charged. The reaction was carried out for 5 hours, cooled to room temperature, and the organic layer was separated from the water using chloroform and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 12.4g of compound B-6 was produced. (yield 61%, MS: [ M+H) ] + ＝346)
Synthesis example 1
Trz1 (15 g,40.8 mmol) and Compound A-1 (14.8 g,42.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (16.9 g,122.3 mmol) was dissolved in 100ml of water and the mixture was poured into the flask, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was poured into the flask. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 17.9g of compound 1 was produced. (yield 80%, MS: [ M+H)] + ＝551)
Synthesis example 2
Trz2 (15 g,38.1 mmol) and Compound A-1 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.6g of compound 2 was produced. (yield 71%, MS: [ M+H) ] + ＝577)
Synthesis example 3
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Trz3 (15 g,34.6 mmol) and compound A-1 (12.5 g,36.3 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.3 g,103.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer and the aqueous layer were separatedAfter that, the organic layer was distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.3g of compound 3 was produced. (yield 67%, MS: [ M+H)] + ＝617)
Synthesis example 4
Trz4 (15 g,35.9 mmol) and Compound A-2 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.9g of compound 4 was produced. (yield 69%, MS: [ M+H) ] + ＝601)
Synthesis example 5
Trz5 (15 g,38.1 mmol) and Compound A-2 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 17.6g of compound 5 was produced. (yield 80%, MS: [ M+H)] + ＝577)
Synthesis example 6
Trz6 (15 g,35.9 mmol) and Compound A-2 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.2g of compound 6 was produced. (yield 66%, MS: [ M+H) ] + ＝601)
Synthesis example 7
Trz7 (15 g,38.1 mmol) and Compound A-2 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.9g of compound 7 was produced. (yield 77%, MS: [ M+H)] + ＝577)
Synthesis example 8
Trz8 (15 g,36.8 mmol) and Compound A-3 (13.3 g,386 mmol) was added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.2 g,110.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13g of compound 8 was produced. (yield 60%, MS: [ M+H) ] + ＝591)
Synthesis example 9
Trz9 (15 g,33.8 mmol) and Compound A-3 (12.2 g,35.5 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (14 g,101.4 mmol) was dissolved in 100ml of water and added thereto, and after stirring sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 12.9g of compound 9 was produced. (yield 61%, MS: [ M+H)] + ＝627)
Synthesis example 10
Trz10 (15 g,33.3 mmol) and Compound A-3 (12.1 g,35 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (13.8 g,100 mmol) was dissolved in 100ml of water and the mixture was poured, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was poured. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved again in chloroform and then dissolved in water,after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 12.9g of compound 10 was produced. (yield 61%, MS: [ M+H) ] + ＝633)
Synthesis example 11
Trz11 (15 g,35.9 mmol) and Compound A-3 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.8g of compound 11 was produced. (yield 64%, MS: [ M+H)] + ＝601)
Synthesis example 12
Trz12 (15 g,35.7 mmol) and compound B-2 (12.9 g,37.5 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.8 g,107.2 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.3g of compound 12 was produced. (yield 62%, MS: [ M+H) ] + ＝603)
Synthesis example 13
Trz13 (15 g,38.1 mmol) and Compound B-2 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.1g of compound 13 was produced. (yield 69%, MS: [ M+H)] + ＝577)
Synthesis example 14
Trz14 (15 g,35.9 mmol) and Compound B-2 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14g of compound 14 was produced. (yield 65%, MS: [ M+H ] ] + ＝601)
Synthesis example 15
Trz15 (15 g,36.8 mmol) and Compound B-1 (13.3 g,38.6 mmol) were added to 300ml THF, stirred andand (5) refluxing. Then, potassium carbonate (15.2 g,110.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.2g of compound 15 was produced. (yield 61%, MS: [ M+H)] + ＝591)
Synthesis example 16
Trz16 (15 g,40.8 mmol) and compound B-1 (14.8 g,42.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (16.9 g,122.3 mmol) was dissolved in 100ml of water and the mixture was poured into the flask, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was poured into the flask. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 17.5g of compound 16 was produced. (yield 78%, MS: [ M+H) ] + ＝551)
Synthesis example 17
Trz17 (15 g,38.1 mmol) and Compound B-1 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. Dissolving in chloroform again, washing with water for 2 times, separatingThe organic layer was added with anhydrous magnesium sulfate, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.7g of compound 17 was produced. (yield 67%, MS: [ M+H)] + ＝577)
Synthesis example 18
Trz18 (15 g,35.9 mmol) and Compound B-3 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.8g of compound 18 was produced. (yield 78%, MS: [ M+H) ] + ＝601)
Synthesis example 19
Trz19 (15 g,43.6 mmol) and Compound B-3 (15.8 g,45.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (18.1 g,130.9 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 17.9g of compound 19 was produced. (yield 78%, MS: [ M+H)] + ＝527)
Synthesis example 20
Trz20 (15 g,38.1 mmol) and Compound B-3 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.7g of compound 20 was produced. (yield 76%, MS: [ M+H) ] + ＝577)
Synthesis example 21
Trz21 (15 g,35.9 mmol) and Compound B-4 (13 g,37.7 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (14.9 g,107.7 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.2g of compound 21 was produced. (yield 66%, MS: [ M+H)] + ＝601)
Synthesis example 22
Trz22 (15 g,34.6 mmol) and Compound B-4 (12.6 g,36.4 mmol) were added to 300ml of THF, stirred and refluxed. Then, the potassium carbonate is(14.4 g,103.9 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16g of compound 22 was produced. (yield 75%, MS: [ M+H) ] + ＝616)
Synthesis example 23
Trz23 (15 g,38.1 mmol) and Compound B-4 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.7g of compound 23 was produced. (yield 67%, MS: [ M+H)] + ＝577)
Synthesis example 24
Trz24 (15 g,33.8 mmol) and Compound B-5 (12.2 g,35.5 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (14 g,101.4 mmol) was dissolved in 100ml of water and added thereto, and after stirring sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. Dissolving in chloroform again, washing with water for 2 times, separating organic layer, adding anhydrous magnesium sulfate, After stirring, filtration was carried out, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.7g of compound 24 was produced. (yield 79%, MS: [ M+H)] + ＝627)
Synthesis example 25
Trz25 (15 g,33.8 mmol) and Compound B-5 (12.2 g,35.5 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (14 g,101.4 mmol) was dissolved in 100ml of water and added thereto, and after stirring sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 15.2g of compound 25 was produced. (yield 72%, MS: [ M+H)] + ＝627)
Synthesis example 26
Trz26 (15 g,33.8 mmol) and Compound B-5 (12.2 g,35.5 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (14 g,101.4 mmol) was dissolved in 100ml of water and added thereto, and after stirring sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was added thereto. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 12.7g of compound 26 was produced. (yield 60%, MS: [ M+H) ] + ＝627)
Synthesis example 27
Trz27 (15 g,40.8 mmol) and Compound B-6 (14.8 g,42.8 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (16.9 g,122.3 mmol) was dissolved in 100ml of water and the mixture was poured into the flask, and after stirring the mixture sufficiently, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was poured into the flask. After 4 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.2g of compound 27 was produced. (yield 72%, MS: [ M+H)] + ＝551)
Synthesis example 28
Trz28 (15 g,36.8 mmol) and Compound B-6 (13.3 g,38.6 mmol) were added to 300ml THF, stirred and refluxed. Then, potassium carbonate (15.2 g,110.3 mmol) was dissolved in 100ml of water and the mixture was stirred well, and bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added thereto. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 16.3g of compound 28 was produced. (yield 75%, MS: [ M+H) ] + ＝591)
Synthesis example 29
Trz29 (15 g,38.1 mmol) and Compound B-6 (13.8 g,40 mmol) were added to 300ml of THF, stirred and refluxed. Then, potassium carbonate (15.8 g,114.3 mmol) was dissolved in 100The mixture was poured with mlml of water, and after stirring thoroughly, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 13.6g of compound 29 was produced. (yield 62%, MS: [ M+H)] + ＝577)
Example 1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was usedAnd the following a-1 compound was p-doped (p-dopping) at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was subjected to vacuum evaporation to form a film thickness +.>Is provided. Next, on the hole transport layer, the film thickness is +.>An electron blocking layer was formed by vacuum evaporation of the EB-1 compound described below. Next, on the EB-1 vapor deposited film, a host compound 1 and a dopant Dp-7 compound were vacuum deposited at a weight ratio of 98:2 to form +.>A red light emitting layer of thickness. On the above-mentioned light-emitting layer, the film thickness is +.>The hole blocking layer was formed by vacuum evaporation of the HB-1 compound described below. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1, thereby giving>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintained Lithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support, thereby manufacturing the organic light emitting device.
Examples 2 to 29
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compounds described in table 1 below were used in the organic light-emitting device of example 1.
Comparative examples 1 to 10
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compounds described in table 1 below were used in the organic light-emitting device of example 1. Compounds B-1 to B-10 in Table 1 below are shown below.
When electric current was applied to the organic light emitting devices manufactured in the above examples 1 to 29 and comparative examples 1 to 10, voltage, efficiency (15 mA/cm 2 Benchmark), the results are shown in table 1 below. Lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
/>
The results of table 1 above were obtained when current was applied to the organic light emitting devices fabricated according to examples 1 to 29 and comparative examples 1 to 10. The red organic light-emitting device of example 1 described above uses a conventionally widely used material, and has a structure in which compound EB-1 is used as an electron blocking layer and Dp-7 is used as a red dopant.
When the compound of the present invention was used in the red light-emitting layer, the drive voltage was reduced and the efficiency and lifetime were increased as compared with those of the comparative example, and it was found that when the compound of the present invention was used as a host, energy transfer to the red dopant in the red light-emitting layer was improved as compared with that of the comparative example. It can be determined that this is because electrons and holes combine to form excitons by more stable equilibrium in the light-emitting layer than the compound of the comparative example.
From the above, it was confirmed that the use of the compound of the present invention as a host for a red light-emitting layer can improve the driving voltage, light-emitting efficiency and lifetime characteristics of an organic light-emitting device.
[ description of the symbols ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: hole blocking layer
9: electron injection and transport layers.
Claims (10)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
X 1 to X 9 Each independently is N or CR 1 And X is 1 To X 9 At least one of which is N,
R 1 is hydrogen; deuterium; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
l are each independently a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups.
2. The compound of claim 1, wherein X 1 To X 9 One of which is N.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-9:
in the chemical formulas 1-1 to 1-9,
X 1 to X 9 、R 1 、L、Ar 1 And Ar is a group 2 As defined in claim 1,
n is an integer from 1 to 8.
4. The compound of claim 1, wherein R 1 Hydrogen or deuterium.
5. The compound according to claim 1, wherein L is a single bond, phenylene or naphthylene,
wherein the phenylene and naphthylene groups are unsubstituted or substituted with one or more deuterium.
6. The compound of claim 1, wherein L is a single bond or any one selected from the group consisting of:
7. according to claimThe compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, 9-phenyl-carbazolyl, carbazol-9-yl, benzophenanthryl or The base group of the modified polyester resin is a modified polyester resin,
the Ar is as follows 1 And Ar is a group 2 Unsubstituted or substituted with one or more deuterium.
8. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
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9. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 8.
10. The organic light-emitting device according to claim 9, wherein the organic layer containing the compound is a light-emitting layer.
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| KR1020220148521A KR20230069842A (en) | 2021-11-12 | 2022-11-09 | Novel compound and organic light emitting device comprising the same |
| KR10-2022-0148521 | 2022-11-09 | ||
| PCT/KR2022/017709 WO2023085834A1 (en) | 2021-11-12 | 2022-11-11 | Novel compound and organic light-emitting device comprising same |
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