CN112867719B - Heterocyclic compound and organic light-emitting device comprising same - Google Patents
Heterocyclic compound and organic light-emitting device comprising same Download PDFInfo
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- CN112867719B CN112867719B CN202080005738.0A CN202080005738A CN112867719B CN 112867719 B CN112867719 B CN 112867719B CN 202080005738 A CN202080005738 A CN 202080005738A CN 112867719 B CN112867719 B CN 112867719B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 8
- 239000000126 substance Substances 0.000 claims abstract description 178
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 239000010410 layer Substances 0.000 claims description 172
- 125000004432 carbon atom Chemical group C* 0.000 claims description 129
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 238000002347 injection Methods 0.000 claims description 41
- 239000007924 injection Substances 0.000 claims description 41
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 40
- 229910052805 deuterium Inorganic materials 0.000 claims description 40
- 239000012044 organic layer Substances 0.000 claims description 35
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- -1 1-methylpentyl Chemical group 0.000 description 68
- 230000015572 biosynthetic process Effects 0.000 description 60
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- 125000000623 heterocyclic group Chemical group 0.000 description 28
- 238000000034 method Methods 0.000 description 22
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- 238000004949 mass spectrometry Methods 0.000 description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000005264 aryl amine group Chemical group 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000002560 nitrile group Chemical group 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000005304 joining Methods 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002219 fluoranthenes Chemical class 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 150000001454 anthracenes Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000001492 aromatic hydrocarbon derivatives Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000003943 azolyl group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000002720 diazolyl group Chemical group 0.000 description 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000002964 pentacenes Chemical class 0.000 description 2
- 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 2
- 150000002987 phenanthrenes Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
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- 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 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
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- DKAARCAIXKXVOU-UHFFFAOYSA-N 2-(2-aminophenyl)ethene-1,1,2-triamine Chemical class C(=C(C=1C(=CC=CC=1)N)N)(N)N DKAARCAIXKXVOU-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000070928 Calligonum comosum Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 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 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
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- 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
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 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
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification relates to heterocyclic compounds and organic light-emitting devices including the same.
The present application claims priority from korean patent application No. 10-2019-0004686, filed in the korean patent office on 14 th month 2019, the entire contents of which are included in the present specification.
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 generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides heterocyclic compounds and organic light-emitting devices comprising the same.
Solution to the problem
The present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
ar1 to Ar4 are the same or different from each other and are each independently a substituent formed by joining one substituent or more than 2 substituents selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or substituents adjacent to each other are combined to form a substituted or unsubstituted ring,
r1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
m is 0 or 1, n is 0 or 1,
the value of m + n is 1,
r1 is an integer of 0 to 5, r2 is an integer of 0 to 3, r3 is an integer of 0 to 2,
when R1 is 2 or more, R1 are the same or different from each other,
When R2 is 2 or more, R2 are the same or different from each other,
when R3 is 2, R3 are the same or different from each other.
In addition, the present specification provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer 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 according to an embodiment of the present specification is used for an organic light emitting device, so that a driving voltage of the organic light emitting device can be reduced, and light efficiency can be improved. In addition, the life characteristics of the device can be improved by utilizing the thermal stability of the compound.
The compounds according to an embodiment of the present description are organic materials suitable for use in vapor deposition devices.
Drawings
Fig. 1 to 3 illustrate examples of an organic light emitting device according to an embodiment of the present specification.
FIG. 4 illustrates TGA analysis of compound A-2 according to an embodiment of the present disclosure.
FIG. 5 illustrates TGA analysis of comparative compound X-7.
[ description of the symbols ]
101: substrate board
102: anode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light-emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: cathode electrode
Detailed Description
The present specification will be described in more detail below.
The compound represented by the above chemical formula 1 has a core structure in which benzofuran is condensed in naphthobenzofuran. 2 arylamino groups are connected in the core structure, thereby having characteristics of long lifetime and high efficiency when used as a dopant of a light emitting layer of an organic light emitting device.
In the present specification, examples of substituents are described below, but are not limited thereto.
In the present description of the invention,indicating the location of the connection.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; an alkyl group; cycloalkyl; an amine group; a silyl group; a phosphine oxide group; an aryl group; and a substituent group containing 1 or 2 or more of the heteroaryl groups of 1 or more of N, O, S and Si atoms, or a substituent group formed by connecting 2 or more of the above-exemplified substituent groups, or no substituent group.
In the present specification, the connection of 2 or more substituents means that hydrogen of any substituent is connected to other substituents. For example, isopropyl group may be linked to phenyl group to formIs a substituent of (a).
In this specification, 3 substituent linkages include not only (substituent 1) to (substituent 2) to (substituent 3) linked in succession, but also (substituent 2) and (substituent 3) linked in (substituent 1). For example, 2 phenyl groups and isopropyl groups are linked, thereby making it possible toIs a substituent of (a). The same description applies to the case where 4 or more substituents are linked.
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 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 30 carbon atoms, 3 to 20 carbon atoms, 3 to 10 carbon atoms, or 3 to 6 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, or the like, but is not limited thereto.
In the present specification, a silyl group is a substituent containing Si and having the above Si atom directly bonded as a radical, and is represented by-SiR 201 R 202 R 203 R represents 201 To R 203 Each of which may be the same or different from the other, may be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of silyl groups includeTrimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, methyldiphenylsilyl, t-butyldiphenylsilyl, phenylsilyl, and the like, but are not limited thereto.
In the present specification, aryl means a 1-valent group of an aromatic hydrocarbon or an aromatic hydrocarbon derivative having 1-valent. In the present specification, an aromatic hydrocarbon means a compound including a planar ring in which pi electrons are completely conjugated, and a group derived from an aromatic hydrocarbon means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed in an aromatic hydrocarbon. In the present specification, an aryl group includes a 1-valent group formed by connecting 2 or more aromatic hydrocarbons or aromatic hydrocarbon derivatives. The aryl group is not particularly limited, but is preferably an aryl group having 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Specifically, examples of the polycyclic aryl group include naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, the above fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
In this specification, when it is indicated that a fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which substituents of five-membered rings of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The above-mentioned substituted fluorenyl group includes, but is not limited to, 9 '-spirobifluorene, spiro [ cyclopentane-1, 9' -fluorene ], spiro [ benzo [ c ] fluorene-7, 9-fluorene ], and the like.
In this specification, a heterocyclic group contains 1 or more non-carbon atoms, i.e., hetero atoms, and specifically, the hetero atoms may contain 1 or more atoms selected from O, N, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 50, 2 to 30,2 to 20, 2 to 18, or 2 to 13. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), thiazolyl, and iso ∈>Azolyl, (-) -and (II) radicals>Diazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, dihydrophenothiazinyl, dihydrobenzisoquinolinyl, benzopyranyl, and the like, but is not limited thereto.
In the present specification, the heterocyclic group may be a single ring or multiple rings, may be an aromatic, aliphatic, or an aromatic and aliphatic condensed ring, and may be selected from the examples of the heterocyclic groups described above.
In the present specification, heteroaryl means a 1-valent aromatic heterocycle. Here, the aromatic heterocycle is a 1-valent group of an aromatic ring or a derivative of an aromatic ring, and is a group containing 1 or more heteroatoms of N, O and S in the ring. The above-mentioned aromatic ring derivatives include all structures in which an aromatic ring or an aliphatic ring is condensed in an aromatic ring. In this specification, a heteroaryl group includes a 1-valent group in which 2 or more aromatic rings having a heteroatom or derivatives of aromatic rings having a heteroatom are bonded to each other. The number of carbon atoms of the above heteroaryl group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13.
In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.
In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.
In the present specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. They may be suitable for the description of heteroaryl groups described above, except that each is a 2-valent group.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on the atom substituted by the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups, except for the 1-valent groups.
In the present specification, the aromatic ring may be a single ring or multiple rings, and may be selected from the above examples of aryl groups, except for 1.
The following describes in detail the compound represented by the above chemical formula 1.
In one embodiment of the present description, m is 0 or 1.
In one embodiment of the present description, n is 0 or 1.
In one embodiment of the present description, the value of m+n is 1.
In the present specification, when m or n is 0, it means that no-O-bond exists between two benzene rings, and the two benzene rings are not connected.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently a substituent formed by joining one substituent or more than 2 substituents selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or substituents adjacent to each other are combined to form a substituted or unsubstituted ring.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted substituent in which one substituent or more substituents of a heterocyclic group having 2 to 30 carbon atoms are bonded, or substituents adjacent to each other are bonded to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, each independently selected from the group consisting of deuterium substituted or unsubstituted alkyl groups; cycloalkyl; silyl groups substituted or unsubstituted with alkyl or aryl groups; aryl substituted or unsubstituted with deuterium, halogen group, alkyl or haloalkyl; and a substituent formed by connecting one substituent or more than 2 substituents in the heterocyclic group substituted or unsubstituted by an alkyl group, or substituents adjacent to each other are combined to form a ring substituted or unsubstituted by an alkyl group.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, each independently is deuterium, a halogen group, an alkyl group substituted with deuterium, a cycloalkyl group, a silyl group substituted with alkyl or aryl, an arylamine group substituted with alkyl or unsubstituted, or a heterocyclic group containing O or S substituted or unsubstituted aryl; or a heterocyclic group substituted or unsubstituted with an alkyl group, or adjacent substituents are combined to form a carbazole ring substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a substituent group formed by joining 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group, an amine group, and a heterocyclic group having 2 to 20 carbon atoms containing O or S; or an O-or S-containing heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms,
Or Ar1 and Ar2 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, and Ar3 and Ar4 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group which is substituted with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, a silyl group, an amine group, and a heterocyclic group containing O or S.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a silyl group, an amine group, a heterocyclic group having 2 to 30 carbon atoms and containing O or S, or a substituent formed by joining 1 or more substituents having 2 or more substituents.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a substituent group formed by joining 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group, an amine group, and a heterocyclic group having 2 to 20 carbon atoms containing O or S.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, an alkyl group substituted or unsubstituted with deuterium or a halogen group, a cycloalkyl group, a silyl group substituted or unsubstituted with an alkyl group or an aryl group, an arylamine group substituted or unsubstituted with an alkyl group, a heterocyclic group containing O or S.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group having 3 to 60 carbon atoms, which is substituted or unsubstituted by 1 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted by deuterium or a halogen group, a cycloalkyl group having 3 to 60 carbon atoms, an silyl group having 3 to 60 carbon atoms substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms or an aryl group having 3 to 60 carbon atoms, an arylamine group having 6 to 90 carbon atoms substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 60 carbon atoms containing O or S.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and are each independently a substituent of 1 or more of a substituent of 6 to 60 carbon atoms substituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 3 to 30 carbon atoms, an aryl group of 3 to 30 carbon atoms substituted with 1 or more of a substituent of 1 to 30 carbon atoms, an aryl group of 2 to 30 carbon atoms, or a heterocyclic group containing O or S.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and are each independently a substituent of 1 or more of a substituent of a heterocyclic group containing O or S of 2 to 30 carbon atoms, which is selected from deuterium, a halogen group, an alkyl group of 1 to 6 carbon atoms substituted or unsubstituted by deuterium or a halogen group, a cycloalkyl group of 3 to 20 carbon atoms, a silyl group of 3 to 20 carbon atoms substituted or unsubstituted by an alkyl group of 1 to 6 carbon atoms or an aryl group of 3 to 20 carbon atoms, an arylamine group of 6 to 40 carbon atoms substituted or unsubstituted by an alkyl group of 1 to 6 carbon atoms, or an aryl group of 3 to 20 carbon atoms substituted or unsubstituted by 1 or more of a heterocyclic group containing O or S.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group having 3 to 30 carbon atoms substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium or a halogen group, a cycloalkyl group having 3 to 30 carbon atoms, an silyl group having 3 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 3 to 30 carbon atoms, and an arylamine group having 6 to 60 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.
In an embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an aryl group having 3 to 20 carbon atoms substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium or a halogen group, a cycloalkyl group having 3 to 20 carbon atoms, and a silyl group having 1 to 6 carbon atoms substituted or unsubstituted with an alkyl group.
In an embodiment of the present specification, ar1 to Ar4 are the same as or different from each other, and each is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, methyl, isopropyl, tert-butyl, cyclohexyl, trimethylsilyl, triethylsilyl, triphenylsilyl, tert-butyldiphenylsilyl, tert-butyldimethylsilyl, methyldiphenylsilyl, ditolylamino, and benzothienyl.
In one embodiment of the present specification Ar1 to Ar4 are the same or different from each other and are each independently phenyl, biphenyl, naphthyl or phenanthryl, the phenyl, biphenyl, naphthyl or phenanthryl being substituted with deuterium, halogen, methyl, CD 3 、CF 3 Isopropyl, tert-butyl, cyclohexyl, trimethylsilyl, triethylsilyl,More than 1 substituent group in triphenylsilyl, t-butyldiphenylsilyl, t-butyldimethylsilyl, methyldiphenylsilyl, and ditolylamino group is substituted or unsubstituted.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.
In one embodiment of the present specification, ar1 to Ar4 are the same or different from each other, and each is independently an O-or S-containing heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.
In an embodiment of the present specification, ar1 to Ar4 are the same as or different from each other, and each is independently dibenzofuranyl, dibenzothienyl, or naphthobenzofuranyl substituted with methyl or tert-butyl.
In one embodiment of the present specification, ar1 to Ar4 are the same as or different from each other, and each is independently a dibenzofuranyl group substituted or unsubstituted with a methyl group or a tert-butyl group.
In one embodiment of the present description, ar1 and Ar2 are combined with each other to form a substituted or unsubstituted ring.
In one embodiment of the present description, ar3 and Ar4 are combined with each other to form a substituted or unsubstituted ring.
In one embodiment of the present specification, ar1 and Ar2 are phenyl groups substituted or unsubstituted with an alkyl group, and are combined with each other to form a carbazole ring substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar3 and Ar4 are phenyl groups substituted or unsubstituted with an alkyl group, and are combined with each other to form a carbazole ring substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, ar1 and Ar2 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.
In one embodiment of the present specification, ar3 and Ar4 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are phenyl groups substituted or unsubstituted with methyl or t-butyl groups, which are combined with each other to form a carbazole ring substituted or unsubstituted with methyl or t-butyl groups.
In one embodiment of the present specification, ar3 and Ar4 are phenyl groups substituted or unsubstituted with methyl or t-butyl groups, which are combined with each other to form a carbazole ring substituted or unsubstituted with methyl or t-butyl groups.
In one embodiment of the present description, ar1 and Ar3 are the same or different from each other.
In one embodiment of the present description, ar2 and Ar4 are the same or different from each other.
In one embodiment of the present description, ar1 and Ar3 are the same.
In one embodiment of the present description, ar2 and Ar4 are the same.
In one embodiment of the present specification, R1 to R3 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In an embodiment of the present specification, R1 to R3 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, an amino group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted, an aryl group having 6 to 30 carbon atoms substituted or unsubstituted, or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted.
In an embodiment of the present specification, R1 to R3 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, an amino group substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted, an aryl group having 6 to 20 carbon atoms substituted or unsubstituted, or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted.
In one embodiment of the present specification, R1 to R3 are the same or different from each other, and each is independently hydrogen or deuterium.
In one embodiment of the present description, R1 to R3 are hydrogen.
In one embodiment of the present specification, R1 is an integer of 0 to 5, R2 is an integer of 0 to 3, R3 is an integer of 0 to 2, R1 is the same or different from each other when R1 is 2 or more, R2 is the same or different from each other when R2 is 2 or more, and R3 is the same or different from each other when R3 is 2.
In one embodiment of the present description, r1 is 0.
In one embodiment of the present disclosure, r2 is 0.
In one embodiment of the present disclosure, r3 is 0.
In one embodiment of the present specification, -N (Ar 1) (Ar 2) and-N (Ar 3) (Ar 4) of the above chemical formula 1 are the same or different from each other.
In one embodiment of the present specification, -N (Ar 1) (Ar 2) and-N (Ar 3) (Ar 4) of chemical formula 1 are the same.
In one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 2-1 or 2-2.
[ chemical formula 2-1]
[ chemical formula 2-2]
In the above chemical formulas 2-1 and 2-2,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
In one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 4-1 or 4-2.
[ chemical formula 4-1]
[ chemical formula 4-2]
In the above chemical formulas 4-1 and 4-2,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
In one embodiment of the present specification, the chemical formula 2-1 is represented by the chemical formula 4-1.
In one embodiment of the present specification, the chemical formula 2-2 is represented by the chemical formula 4-2.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-8.
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formula 3-3]
[ chemical formulas 3-4]
[ chemical formulas 3-5]
[ chemical formulas 3-6]
[ chemical formulas 3-7]
[ chemical formulas 3-8]
In the above chemical formulas 3-1 to 3-8,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
In one embodiment of the present specification, the above chemical formula 2-1 is represented by any one of the above chemical formulas 3-1 to 3-4.
In one embodiment of the present specification, the above chemical formula 2-2 is represented by any one of the above chemical formulas 3-5 to 3-8.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 5-1 to 5-8.
[ chemical formula 5-1]
[ chemical formula 5-2]
[ chemical formulas 5-3]
[ chemistry 5-4]
[ chemical formulas 5-5]
[ chemical formulas 5-6]
[ chemical formulas 5-7]
[ chemistry 5-8]
In the above chemical formulas 5-1 to 5-8,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
In one embodiment of the present specification, the above chemical formula 2-1 is represented by any one of the above chemical formulas 5-1 to 5-4.
In one embodiment of the present specification, the above chemical formula 2-2 is represented by any one of the above chemical formulas 5-5 to 5-8.
In one embodiment of the present specification, the above chemical formula 4-1 is represented by any one of the above chemical formulas 5-1 to 5-4.
In one embodiment of the present specification, the above chemical formula 4-2 is represented by any one of the above chemical formulas 5-5 to 5-8.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.
The compound according to an embodiment of the present specification can be produced by a production method described below. Substituents may be added or removed as necessary, and the positions of the substituents may be changed. The starting materials, the reaction conditions, and the like may be modified based on techniques known in the art.
For example, the compound represented by the above chemical formula 1 can produce a core structure as in the following reaction formula 1. Substituents may be combined by methods known in the art, and the kind, position or number of substituents may be changed according to techniques known in the art. The substituent may be bonded as in the following formula 1, but is not limited thereto.
[ general formula 1]
In the above general formula 1, ar1 to Ar4 are defined as in the above chemical formula 1. In the above general formula 1, although R1 to R3 are not shown, a reactant substituted with R1 to R3 is used, or R1 to R3 are substituted in the above produced compound using a known method, whereby a desired compound can be obtained.
The present specification provides an organic light emitting device comprising the above-mentioned compound.
The present specification provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer 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.
According to an embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the maximum light emission peak of the light emitting layer including the compound represented by the above chemical formula 1 is 400nm to 500nm. That is, the light emitting layer including the compound represented by the above chemical formula 1 emits blue light.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In the present specification, the term "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target region. The size of the "layers" is not limited, and the respective "layers" may be the same or different in size. In one embodiment, the size of the "layer" may be equal to the entire device, may correspond to the size of a particular functional area, or may be as small as a single sub-pixel (sub-pixel).
In the present specification, the meaning that a specific a substance is contained in a B layer includes all of i) a case where 1 or more a substances are contained in a B layer of one layer, and ii) a case where a B layer is composed of 1 or more layers and a substance is contained in 1 or more layers of a multi-layer B layer.
In the present specification, the meaning of a specific substance a contained in the C layer or D layer means all of the following cases: i) 1 or more of the C layers of 1 or more, or ii) 1 or more of the D layers of 1 or more, or iii) C layers of 1 or more and D layers of 1 or more, respectively.
The organic light emitting device according to the present specification may include an additional organic layer in addition to the above-described light emitting layer.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like may be provided. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula H.
[ chemical formula H ]
In the above-mentioned chemical formula H,
l21 and L22 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
r21 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms containing N, O or S.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently being a direct bond; arylene having 6 to 20 carbon atoms; or a heteroarylene group having 2 to 20 carbon atoms which contains N, O or S. The above arylene or heteroarylene group is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. In another embodiment, the above "substituted or unsubstituted" means substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms, or does not have any substituent.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted thienyl group of 2 valency.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, and are each independently a direct bond, phenylene, naphthylene, or a 2-valent thienyl group.
In one embodiment of the present specification, L21 and L22 are the same or different from each other, each independently is a direct bond, phenylene, or naphthylene.
In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with Y1, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with Y1.
In an embodiment of the present specification, ar21 and Ar22 are the same or different from each other, each independently is a monocyclic to tetracyclic aryl group substituted or unsubstituted by Y1, or a monocyclic to tetracyclic heteroaryl group substituted or unsubstituted by Y1.
In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted by Y1, a biphenyl group substituted or unsubstituted by Y1, a benzocarbazolyl group substituted or unsubstituted by Y1, a dibenzofuranyl group substituted or unsubstituted by Y1, an anthracenyl group substituted or unsubstituted by Y1, a phenanthrenyl group substituted or unsubstituted by Y1, a fluorenyl group substituted or unsubstituted by Y1, a benzofluorenyl group substituted or unsubstituted by Y1, a furanyl group substituted or unsubstituted by Y1, a thienyl group substituted or unsubstituted by Y1, a carbazolyl group substituted or unsubstituted by Y1, a dibenzofuranyl group substituted or unsubstituted by Y1, a naphthobenzofuranyl group substituted or unsubstituted by Y1, a dibenzofuranyl group substituted or unsubstituted by Y1, a dibenzothiophenyl group substituted or unsubstituted by Y1, a naphthothiophenyl group substituted or unsubstituted by Y1, a pyridine substituted or unsubstituted by Y1, a pyrimidine substituted or unsubstituted by Y1, a quinoline substituted or unsubstituted by Y1, a 1-substituted or a quinoline substituted or unsubstituted by a 1, a 1.
In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted by Y1, a biphenyl group substituted or unsubstituted by Y1, a naphthyl group substituted or unsubstituted by Y1, an anthryl group, a phenanthryl group, a phenacyl group, a thienyl group substituted or unsubstituted by Y1, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, a pyridyl group, an isoquinolyl group, or an indolo [3,2,1-jk ] carbazolyl group.
In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and each is independently an aryl group having 6 to 20 carbon atoms or an O-containing heteroaryl group having 2 to 20 carbon atoms.
In one embodiment of the present specification, ar21 and Ar22 are the same or different from each other, and are each independently phenyl, biphenyl, 1-naphthyl, 2-naphthyl, dibenzofuranyl or naphthobenzofuranyl.
In one embodiment of the present specification, Y1 is deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, Y1 is deuterium, a halogen group, a nitrile group, a methyl group, a cyclohexyl group, a trimethylsilyl group, or a phenyl group.
In one embodiment of the present specification, Y1 is deuterium, fluoro, nitrile, methyl, cyclohexyl or trimethylsilyl.
In one embodiment of the present specification, R21 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R21 to R28 are the same or different from each other, and are each independently hydrogen or deuterium.
In one embodiment of the present specification, 4 or more of R21 to R28 are deuterium, and the rest are hydrogen.
In one embodiment of the present disclosure, R21 to R28 are deuterium.
In one embodiment of the present description, R21 to R28 are hydrogen.
In one embodiment of the present disclosure, formula H above comprises at least one or more deuterium.
In one embodiment of the present specification, the compound represented by the above formula H is any one selected from the following compounds.
An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including a compound represented by the above chemical formula 1 as a dopant of the light emitting layer and a compound represented by the above chemical formula H as a host of the light emitting layer.
In one embodiment of the present specification, the content of the compound represented by the above chemical formula 1 is 0.01 to 30 parts by weight, 0.1 to 20 parts by weight, or 0.5 to 10 parts by weight based on 100 parts by weight of the compound represented by the above chemical formula H.
In one embodiment of the present specification, the light emitting layer may further include a host substance in addition to the compound represented by the chemical formula H. In this case, the host material (mixed host compound) further contained includes an aromatic condensed ring derivative, a heterocyclic compound or 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 dibenzofuran derivatives and trapezoidal furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
The mixing ratio of the compound represented by the above chemical formula H and the above mixed host compound is 95:5 to 5:95.
In one embodiment of the present specification, the light emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H is blue.
An organic light emitting device according to an embodiment of the present specification includes 2 or more light emitting layers, and at least one of the 2 or more light emitting layers includes a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula H. The light emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H is blue, and the light emitting layer not including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H may include a blue, red, or green light emitting compound known in the art.
In an embodiment of the present disclosure, the organic layer includes a hole injection layer or a hole transport layer. The hole injection layer or the hole transport layer contains a compound represented by the above chemical formula 1.
In an embodiment of the present disclosure, the organic layer includes an electron injection layer or an electron transport layer. The electron injection layer or the electron transport layer contains a compound represented by the above chemical formula 1.
In an embodiment of the present disclosure, the organic layer includes an electron blocking layer.
In an embodiment of the present disclosure, the organic layer includes a hole blocking layer.
In an embodiment of the present specification, the organic light emitting device further includes 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
In an embodiment of the present specification, the organic light emitting device includes: a first electrode; a second electrode provided opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and an organic layer having 2 or more layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.
In one embodiment of the present invention, the 2 or more organic layers may be selected from a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that performs hole transport and hole injection simultaneously, and an electron blocking layer, and may be 2 or more.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In one embodiment of the present disclosure, the first electrode is a cathode, and the second electrode is an anode.
In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light emitting device may have 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 specification is illustrated in fig. 1 to 3. The above-described fig. 1 to 3 illustrate the organic light emitting device, but are not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. The compound represented by the above chemical formula 1 is contained in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. According to an embodiment of the present specification, the compound represented by chemical formula 1 described above is included in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer. According to another embodiment, the compound represented by chemical formula 1 above is contained in a hole injection layer or a hole transport layer.
Fig. 3 illustrates a structure of an organic light-emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110 are sequentially stacked on a substrate 101. According to an embodiment of the present specification, the compound represented by chemical formula 1 described above is included in the light emitting layer. According to an embodiment of the present specification, the compound represented by the above chemical formula H may be further included in the light emitting layer. According to another embodiment, the compound represented by the above chemical formula 1 is contained in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.
The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that the light emitting layer includes the above compound, i.e., the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula H.
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 of the present specification may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it 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 or the compound represented by the above chemical formula H may be used not only in the vacuum vapor deposition method but also in the solution coating method to form the organic layer in the production of the 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 may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.
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. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or 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]Conductivity of (PEDOT), polypyrrole, polyaniline and the likePolymers, etc., but is 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. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The organic light emitting device according to the present specification may include an additional light emitting layer other than the light emitting layer including the compound represented by the above chemical formula 1 or the compound represented by the above chemical formula H. The further light emitting layer may comprise 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 dibenzofuran derivatives and trapezoidal furan compounds Pyrimidine 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 arylamine group, and includes pyrene, anthracene having an arylamine group,Bisindenopyrene, and the like. Further, the 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 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styrylenediamine, and styryl Triamines, styrenetetramines, and the like, but are not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The hole injection layer is a layer that receives holes from the electrode. The hole injection substance is preferably the following: a substance having a hole transporting ability, an effect of receiving holes from the anode, and an excellent hole injecting effect for the light emitting layer or the light emitting material. Further, a substance having an excellent ability to prevent migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital ) of the hole injecting substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; hexanitrile hexaazatriphenylene organic compounds; quinacridone (quinacridone) is an organic substance; perylene (perylene) based organic compounds; anthraquinone, polyaniline, polythiophene-based conductive polymer, and the like, but is not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring them to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples thereof include an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and unconjugated portions, but are not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting 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 mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 The complex of (a) is not limited to, but is an organic radical compound, a hydroxyflavone-metal complex, and the like. The electron transport layer can be as in the prior artAs used with any desired cathode material. In particular, suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and an aluminum layer or a silver layer is included in each case.
The electron injection layer is a layer that receives electrons from the electrode. The electron injecting substance is preferably the following: a substance having an excellent electron-transporting ability, an effect of receiving electrons from the second electrode, and an excellent electron-injecting effect to the light-emitting layer or the light-emitting material. Further, a substance which prevents migration of excitons generated in the light-emitting layer to the hole injection layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole (S),Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
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-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The electron blocking layer is a layer that improves the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. The known material can be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs hole injection and hole transport at the same time.
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as the electron injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
In the following, examples, comparative examples, and the like are described in detail for the purpose of specifically describing the present specification. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification should not be construed as being limited to the examples and comparative examples described in detail below. Examples and comparative examples of the present description are provided to more fully illustrate the present description to those skilled in the art.
Synthesis example
Synthesis example 1 Synthesis of intermediate S-3
60g of compound S-1, 62.8g of compound S-2, 43.5g of potassium carbonate (potassium carbonate) and 600mL of two are added under nitrogen atmosphereAfter alkane and 150mL of water, 2.1g of tetrakis (triphenylphosphine) palladium (0) (Pd (PPh) 3 ) 4 ) After that, heating and stirring were carried out at 120℃for 8 hours. After the reaction, the reaction mixture was cooled to room temperature, water and ethyl acetate were added, and after separation, mgSO was performed 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethyl acetate/hexane) to obtain 63.5g of an intermediateS-3. Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=379.
Synthesis example 2 Synthesis of intermediate S-5
61g of Compound S-3 and 55.6g of potassium carbonate were added to 550mL of N-dimethylformamide (N-dimethylformamide) under nitrogen atmosphere, and stirred at 160℃for 2 hours, thereby synthesizing intermediate S-4. After the completion of the reaction, the reaction solution was cooled to room temperature, 63g of perfluorobutylsulfonyl fluoride (perfluorobutanesulfonyl floride) was immediately added thereto, and the mixture was stirred for 1 hour. After the reaction, water and ethyl acetate were added, and after separation, mgSO was performed 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (toluene/hexane), whereby 52g of intermediate S-5 was obtained.
Synthesis example 3 Synthesis of intermediate S-7
By using 20g of S-1 in the same manner as in Synthesis example 1. Intermediate S-3, intermediate S-7 (20.3 g) was obtained. Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=379.
Synthesis example 4 Synthesis of intermediate S-10
By using 18g of S-7 in the same manner as in Synthesis example 2. Intermediate S-5, intermediate S-10 (15.5 g) was obtained.
Synthesis example 5 Synthesis of Compound A-2
3g of Compound S-5, 2.8g of N-1 and 3.5g of potassium phosphate (potassium phosphate) were added to 20mL of xylene under a nitrogen atmosphere, and 0.09g of bis (dibenzylideneacetone) palladium (0) (Bis (dibenzylideneacetone) paladium (0)) and 0.13g of 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (Xphos) were dissolved in xylene and slowly added dropwise to the reaction solution. The reaction solution was heated at 140℃and stirred for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, water and NaCl solution were added, and MgSO was performed after separation 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (toluene/hexane), whereby Compound A-2 (2.6 g) was obtained. Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=867.
Synthesis example 6 Synthesis of Compound A-3
Compound A-3 (2.7 g) was obtained by the same method as that of Compound A-2 of Synthesis example 5. Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=935.
Synthesis example 7 Synthesis of Compound A-4
Compound A-4 (2.4 g) was obtained in the same manner as in Synthesis example 5. Compound A-2. Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peak was confirmed at=1011.
Synthesis example 8 Synthesis of Compound A-5
By passing throughCompound A-5 (1.9 g) was obtained in the same manner as in Synthesis example 5. Compound A-2. Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=1043.
Synthesis example 9 Synthesis of Compound A-6
Compound A-6 (2.8 g) was obtained in the same manner as in Synthesis example 5. Compound A-2. Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=991.
Synthesis example 10 Synthesis of Compound A-7
Compound A-7 (3.0 g) was obtained by the same method as that of Compound A-2 of Synthesis example 5. Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=970.
Synthesis example 11 Synthesis of Compound C-1
By the same method as that of Synthesis example 5. Compound A-2, 4g of intermediate S-10 was used, thereby obtaining Compound C-1 (3.5 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=1048.
Synthesis example 12 Synthesis of intermediate S-14
Intermediate S-14 (34 g) was obtained by using 40g of S-1 in the same manner as in Synthesis example 1. Intermediate S-3 and Synthesis example 2. Intermediate S-5.
Synthesis example 13 Synthesis of intermediate S-17
20g of S-1 was used in the same manner as in Synthesis example 1. Intermediate S-3 and Synthesis example 2. Intermediate S-5, thereby obtaining intermediate S-17 (8 g).
Synthesis example 14 Synthesis of Compound B-2
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-2 (2.7 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=947.
Synthesis example 15 Synthesis of Compound B-3
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-3 (2.4 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks are confirmed at=811.
Synthesis example 16 Synthesis of Compound B-4
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-4 (3.1 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=1193.
Synthesis example 17 Synthesis of Compound B-5
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-5 (2.6 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=1019.
Synthesis example 18 Synthesis of Compound B-6
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-6 (2.5 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]Peaks were confirmed at=1061.
Synthesis example 19 Synthesis of Compound B-7
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-14 was used, thereby obtaining Compound B-7 (2.2 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at=863.
Synthesis example 20 Synthesis of Compound D-1
By the same method as that of Synthesis example 5. Compound A-2, 3g of intermediate S-17 was used, thereby obtaining Compound D-1 (1.7 g). Mass spectrometry of the obtained solid was found in [ M+H ] + ]The peak was confirmed at= 726.32.
Experimental example 1
Examples 1 to 2.
For the above compounds, HOMO, LUMO and singlet (S) were calculated in the absorption (adsorption) state of the molecule by TD-DFT (B3 LYP) method/6-31G group method 1 ) The energy level of (a) and the singlet oscillator strength (oscillator strength) (the probability of radiation transition, f). The calculation results are shown in table 1 below.
TABLE 1
The emission wavelength of a compound is a value obtained by shifting Stokes shift (Stokes shift) from the absorption wavelength, and the degree of the emission wavelength can be predicted from the absorption wavelength.
The radiation transition probability (f) is calculated as a scale showing fluorescence quantum efficiency by the following formula. The larger the radiation transition probability (f) value, the higher the luminous efficiency.
Vibrator strength
V is in S -1 Frequency of (2)
ε (v) is the unit M -1 cm - Molar extinction coefficient of 1
The probability of radiative transitions (f) for comparative examples 1-2 gave very small values compared to compounds A-1, B-1 of examples 1-2, and it was predicted that the efficiency of devices comprising compounds X-1 to X-2 was very low. In addition, the emission wavelength can be predicted by the singlet energy value of the compound X-1, and since it is a very short wavelength compared to the compound of the example, it is expected that the efficiency of the device is very low when used as a blue emission dopant of the light layer, and thus cannot be said to be a suitable blue emission dopant.
Therefore, the compounds A-1 and B-1 have higher luminous efficiency and the blue light emitting device has higher efficiency than the compounds X-1 and X-2.
Experimental example 2: device example
Example 3.
A glass substrate coated with ITO (indium tin oxide) at a thickness of 150nm into a thin film was put into distilled water in which a detergent was 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, a hole injection layer was formed by thermal vacuum evaporation of the following compound HAT at a thickness of 5 nm. On the hole injection layer, a first hole transport layer having a thickness of 100nm was formed by vacuum evaporation of the following compound HT-A, and then a second hole transport layer having a thickness of 10nm was formed by vacuum evaporation of the following compound HT-B. On the second hole transport layer, a host compound BH-A and a dopant compound A-2 were vacuum-evaporated at a weight ratio of 96:4, thereby forming a light-emitting layer having a thickness of 20 nm.
Then, the following compound ET-a and compound Liq were evaporated at a weight ratio of 1:1, thereby forming an electron injection and transport layer of 30 nm. On the electron injection and transport layer, silver (Ag) and magnesium (Mg) were vapor-deposited at a weight ratio of 9:1 and a thickness of 15nm, and aluminum was vapor-deposited at a thickness of 100nm to form a cathode, thereby manufacturing an organic light-emitting device.
In the above-mentioned process, the vapor deposition rate of the organic material was maintained at 0.1nm/sec, that of LiF was maintained at 0.02nm/sec, and that of aluminum was maintained at 0.3nm/sec to 0.7 nm/sec.
Examples 4 to 14 and comparative examples 3 to 6.
An organic light-emitting device was fabricated in the same manner as in example 3, except that the substances of table 2 below were used as the dopant and the host compound of the light-emitting layer in example 3 above.
Will be at 20mA/cm 2 The results of experiments conducted on organic light emitting devices manufactured using each compound as a host and a dopant substance at current densities of (a) are shown in table 2 below. In terms of lifetime, the time when the luminance became 97% of the initial luminance was measured (T97).
TABLE 2
As shown in table 2 above, the devices of examples 3 to 14 using the compound having the structure of chemical formula 1 have characteristics of blue high efficiency and long lifetime as compared with the devices of comparative examples 3 to 6.
Experimental example 3: maximum luminescence wavelength determination and TGA analysis
Example 15 and comparative examples 7 to 9
The maximum emission wavelength of the following compounds was measured and is shown in Table 3 below, and the measurement device used for measuring them was a JASCO FP-8600 fluorescence spectrophotometer.
The maximum emission wavelength of the compound can be obtained as follows. The compound to be measured was dissolved to a concentration of 1 μm (micro M) using toluene as a solvent, thereby preparing a sample for measurement. The sample solution was put into a quartz cuvette, and nitrogen (N 2 ) Degassing (degaussing) is carried out, so as to remove oxygen from the solution,then, the fluorescence spectrum was measured at room temperature (300K) by a measuring device. In this case, the wavelength value (nm) of the maximum luminescence peak can be obtained.
TABLE 3
TGA (thermos gravimetric analyzer, thermogravimetric analyzer) is a device that heats a sample and measures a change in mass of the sample as a function of time or temperature. The loss of mass of the material occurs by evaporation or chemical reaction that produces gaseous products. Using Q-500, less than 5mg of the sample was charged into a platinum pan (Pt pan), and heated from room temperature to 700℃at a rate of 20℃per minute. At this time, the temperature of 1% mass reduction with respect to the total weight of the compound (= Td-1% loss (loss)) and the amount (percentage) of the residue left in the pan (pan) after heating to 700 ℃ were measured. The TGA graph of compound A-2 of example 15 is shown in FIG. 4 and the TGA graph of compound X-7 of comparative example 9 is shown in FIG. 5.
Although the compounds X-3, X-6, A-2 of comparative examples 7, 8 and example 15 all have the same molecular weight, the maximum emission wavelength is different. The compound a-2 satisfying the above chemical formula 1 has the most appropriate emission wavelength when used as a blue emission dopant. The maximum luminescence wavelength of the compound X-6 is a very short wavelength.
Compound X-7 (comparative example 9) having a maximum emission wavelength similar to that of Compound A-2 (example 15) was found to have a thermal gravimetric analysis experiment result Td-1% loss value of 490 ℃. Is a very high value when compared with the Td-1% loss value (395 ℃) of the compound a-2 (example 15) satisfying chemical formula 1 of the present invention. In addition, compound X-7 of comparative example 9 remained 62% of the compound in the pot after TGA analysis, but compound a-2 of the example of the present invention remained 2.8% of the compound in the pot after TGA analysis.
Through this experiment, the compound satisfying the above chemical formula 1 has a suitable maximum emission wavelength as a blue fluorescent dopant, and also has a low Td-1% loss value, compared with similar molecular weights, and thus is confirmed to be an organic material suitable for vapor deposition devices.
Claims (9)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
ar1 to Ar4 are the same as or different from each other and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted by 1 or more substituents selected from deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted by deuterium or a halogen group, a cycloalkyl group having 3 to 20 carbon atoms, an silyl group having 6 to 20 carbon atoms substituted or unsubstituted by an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 40 carbon atoms substituted or unsubstituted by an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an heteroaryl group having 2 to 30 carbon atoms and having O or S, or an heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted by an alkyl group having 1 to 6 carbon atoms,
or Ar1 and Ar2 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, ar3 and Ar4 are phenyl groups substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms and are bonded to each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms,
R1 to R3 are hydrogen or deuterium,
m is 0 or 1, and n is 0 or 1,
the value of m + n is 1,
r1 is 5, r2 is 3, and r3 is 2.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2-1 or 2-2:
chemical formula 2-1
Chemical formula 2-2
In the chemical formulas 2-1 and 2-2,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4-1 or 4-2:
chemical formula 4-1
Chemical formula 4-2
In the chemical formulas 4-1 and 4-2,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
4. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-8:
chemical formula 3-1
Chemical formula 3-2
Chemical formula 3-3
Chemical formulas 3-4
Chemical formulas 3-5
Chemical formulas 3-6
Chemical formulas 3-7
Chemical formulas 3-8
In the chemical formulas 3-1 to 3-8,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
5. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 5-1 to 5-8:
Chemical formula 5-1
Chemical formula 5-2
Chemical formula 5-3
Chemical formula 5-4
Chemical formula 5-5
Chemical formulas 5-6
Chemical formulas 5-7
Chemical formulas 5-8
In the chemical formulas 5-1 to 5-8,
ar1 to Ar4, R1 to R3 and R1 to R3 are as defined in chemical formula 1.
6. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
7. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode in 1 or more layers, wherein the organic layer includes a light-emitting layer containing a dopant substance, and the dopant substance contains the compound according to any one of claims 1 to 7.
8. The organic light-emitting device according to claim 7, wherein the light-emitting layer further comprises a compound represented by the following chemical formula H:
chemical formula H
In the chemical formula H described above, the amino acid sequence,
l21 and L22 are the same or different from each other and are each independently a directly bonded or unsubstituted arylene group having 6 to 20 carbon atoms,
r21 to R28 are hydrogen or deuterium, and
Ar21 and Ar22 are the same as or different from each other, and are each independently an unsubstituted aryl group having 6 to 30 carbon atoms or an unsubstituted heteroaryl group having 2 to 30 carbon atoms.
9. The organic light-emitting device according to claim 7, wherein the organic layer further comprises 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
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