CN113227082B - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- CN113227082B CN113227082B CN202080007199.4A CN202080007199A CN113227082B CN 113227082 B CN113227082 B CN 113227082B CN 202080007199 A CN202080007199 A CN 202080007199A CN 113227082 B CN113227082 B CN 113227082B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 104
- 239000000126 substance Substances 0.000 claims description 95
- -1 dibenzofuranyl Chemical group 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 239000012044 organic layer Substances 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000003003 spiro group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 125
- 238000002347 injection Methods 0.000 description 34
- 239000007924 injection Substances 0.000 description 34
- 238000004519 manufacturing process Methods 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000032258 transport Effects 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006069 Suzuki reaction reaction Methods 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006757 chemical reactions by type Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 6
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 150000003918 triazines Chemical class 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 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
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-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
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
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- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
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- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 229940121889 Endothelin A receptor antagonist Drugs 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 150000001241 acetals Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 125000003277 amino 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
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000003062 endothelin A receptor antagonist Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
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Abstract
The present invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2019-0017984, 2 nd month 15 of 2019, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exciton) are formed, and light is emitted when the excitons re-transition to the ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
[ Prior Art literature ]
[ Patent literature ]
(Patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 to L 3 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene group; or a substituted or unsubstituted C 2-60 heteroarylene group containing any one or more heteroatoms selected from N, O and S,
A is a substituent represented by the following chemical formula 2,
[ Chemical formula 2]
In the above-mentioned chemical formula 2,
T 1 to T 4 are each independently a C 6-60 aromatic ring; or a C 2-60 aromatic heterocycle comprising any one or more heteroatoms selected from N, O and S,
W 1 is O, S, NR 5 or CR 6R7,
W 2 is a single bond, O, S, NR 8 or CR 9R10,
One of R 1 to R 10 is combined with L 1, and the others are each independently hydrogen; deuterium; tri (C 1-60 alkyl) silyl; a tri (C 6-60 aryl) silyl group; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising any one or more heteroatoms selected from N, O and S; or may combine with adjacent substituents to form a C 6-60 spiro ring, a C 6-60 aromatic ring, or a C 2-60 aromatic heterocycle containing any one or more heteroatoms selected from N, O and S,
N1 to n4 are each an integer of 1 to 4,
B is a substituent represented by the following chemical formula 3,
Ar is a substituent represented by the following chemical formula 3; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
[ Chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
X is O or S, and the X is O or S,
One of Z 1 to Z 3 is combined with L 2 or L 3, the remainder each independently being hydrogen; deuterium; tri (C 1-60 alkyl) silyl; a tri (C 6-60 aryl) silyl group; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
M is an integer of 1 to 4,
When n1 to n4 and m are 2 or more, the structures in brackets are the same or different from each other.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode; a second electrode disposed 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 represented by the above chemical formula 1 can be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjustment layer 8, a light-emitting layer 4, an electron adjustment layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
Definition of terms
In the present description of the invention,AndRepresents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]Alkyl thioxy) of the formula (i); arylthio- Aryl thioxy); alkylsulfonyl [ ]Alkyl sulfoxy); arylsulfonyl radical [ ]Aryl sulfoxy) of the formula (i); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom, or a substituent linked with 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may be
Etc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,An azolyl group,Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isozylOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In this specification, alkenyl groups in aralkenyl groups are the same as those exemplified for the alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied thereto. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
Compounds of formula (I)
In another aspect, the present invention provides an amine compound represented by the above chemical formula 1.
The amine compound represented by the above chemical formula 1 contains both a substituent having a spiro structure and any one of a benzofuranyl group and a benzothienyl group, whereby high efficiency, low driving voltage, long life and the like of an organic light emitting device using the same can be achieved.
In the above chemical formula 1, preferably, each of L 1 to L 3 is independently a single bond, phenylene, biphenyldiyl, naphthylene, or 9, 9-dimethyl-9H-fluorenylene.
More preferably, each of L 1 to L 3 is independently a single bond, or any one selected from the following groups:
Preferably, in the above chemical formula 2, W 2 is a single bond.
More preferably, A is represented by the following chemical formula 2-1:
[ chemical formula 2-1]
In the above chemical formula 2-1,
T 1 to T 4 are each independently a benzene ring, a naphthalene ring, a phenanthrene ring or a dibenzofuran ring,
W 1 is O, S, NR 5 or CR 6R7,
One of R 1 to R 5 is combined with L 1, the rest is hydrogen, deuterium, tri (C 1-4 alkyl) silyl, C 1-10 alkyl or C 6-20 aryl, or R 5 can be combined with an adjacent substituent R 1 to form an indole ring,
R 6 and R 7 are each independently C 1-10 alkyl or C 6-20 aryl, or can be combined with each other to form a fluorene spiro ring.
In this case, the formation of the screw structure means a structure in which one carbon is used as a contact point for connection.
Most preferably, A is represented by the following chemical formula 2-2:
[ chemical formula 2-2]
In the above chemical formula 2-2,
T 1 to T 4 are each independently selected from any one of the following formulae T1 to T7,
In the above formulas t1 to t7,
* And each carbon atom is fused to each of the carbon atoms of formulas 2-2 above to form a ring.
W 1 is O, S, NR 5 or CR 6R7,
One of R 1 to R 5 is bonded to L 1, R 1 to R 4 in the rest are each independently hydrogen, phenyl, biphenyl or trimethylsilyl, R 5 is phenyl, naphthyl or biphenyl, or may be bonded to an adjacent substituent R 1 to form an indole ring,
R 6 and R 7 are each independently methyl, ethyl, hexyl or phenyl, or can combine with each other to form a fluorene spiro ring.
For example, a may be represented by any one of the following chemical formulas a1 to a 16:
In the above chemical formulas a1 to a16,
W 3 is O or S, and the total number of the components is equal to the total number of the components,
W 4 is O, S, N (phenyl) or C (methyl) 2,
One of R is combined with L 1, the rest is hydrogen,
R 3 is hydrogen, phenyl, biphenyl or trimethylsilyl,
R 5 is phenyl, naphthyl or biphenyl,
R 6 and R 7 are each independently methyl, ethyl, hexyl or phenyl.
Preferably, the substituent represented by the above chemical formula 3 is represented by any one of the following chemical formulas b1 to b 3:
in the above formulas b1 to b3,
X is O or S, and the X is O or S,
Z 1 and Z 2 are each independently hydrogen, C 1-10 alkyl, C 6-20 aryl, or C 2-20 heteroaryl comprising O or S,
Z 3 is hydrogen, deuterium, tri (C 1-4 alkyl) silyl, C 1-10 alkyl, C 6-20 aryl, or C 2-20 heteroaryl containing O or S,
M is 1,2, 3 or 4.
More preferably, in the above chemical formulas b1 to b3,
Z 1 and Z 2 are each independently hydrogen, methyl, ethyl, isopropyl, phenyl, biphenyl, naphthyl or dibenzofuranyl,
Z 3 is hydrogen, deuterium, trimethylsilyl, methyl, isopropyl, phenyl, naphthyl or dibenzofuranyl.
Most preferably, in the above formulas b1 to b3, Z 1 is hydrogen, methyl, ethyl, isopropyl, phenyl, biphenyl, naphthyl or dibenzofuranyl, and Z 2 is hydrogen, methyl, ethyl, phenyl or biphenyl.
Preferably, ar is a substituent represented by the above chemical formula 3; any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spiro [ cyclopentane-1, 9 '-fluorenyl ] group and spiro [ cyclohexane-1, 9' -fluorenyl ] group; or any heteroaryl group selected from dibenzofuranyl, dibenzothiophenyl and carbazolyl,
Wherein the above aryl and heteroaryl groups are each independently unsubstituted or substituted with 1 to 5 substituents each independently selected from deuterium, trimethylsilyl, triphenylsilyl, C 1-10 alkyl, and C 6-20 aryl.
More preferably, ar is a substituent represented by the above chemical formula 3, or is any one selected from the following groups:
of the above-mentioned groups, the group,
Y is O, S, N (phenyl), C (methyl) (ethyl) or C (methyl) 2,
Q is hydrogen or phenyl, and the hydrogen is hydrogen,
Q' is methyl or phenyl.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
on the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1. The above-described production method can be more specifically described in the production example described later.
[ Reaction type 1]
In the above reaction formula 1, each X' is independently halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description.
Step 1-1 is a step of producing an intermediate compound X (int.x) by introducing an SM2 radical into a primary amine of a starting material SM1, and step 1-2 is a step of producing a compound represented by the above chemical formula 1 as a tertiary amine compound by introducing an int.y radical into a secondary amine of the intermediate compound X (int.x). The above steps 1-1 and 1-2 are all carried out using a Buchwald-Hartmay (Buchwald-Hartwig) reaction, which are preferably carried out in the presence of a palladium catalyst. Such a manufacturing method can be more concretely described in a manufacturing example described later.
Organic light emitting device
In another aspect, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode; a second electrode disposed 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.
The organic layer of the organic light-emitting device of the present invention 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, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. The structure of the organic light emitting device is not limited thereto and may include a smaller or larger number of organic layers.
The organic light-emitting device according to the present invention may have a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on a substrate. The organic light-emitting device according to the present invention may have a reverse structure (inverted type (INVERTED TYPE)) in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjustment layer 8, a light-emitting layer 4, an electron adjustment layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole transporting layer, the hole adjusting layer, or may be contained in both the above hole transporting layer and the hole adjusting layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; a multilayer structure such as LiF/Al or LiO 2/Al, but not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. As the hole transporting substance, the compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, or the like may be used, but the present invention is not limited thereto.
The hole regulating layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and the hole transport layer is preferably provided so as to be in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility and preventing excessive migration of electrons to increase the probability of hole-electron bonding. The hole-regulating layer contains a hole-regulating substance, and as an example of such a hole-regulating substance, a compound represented by the above chemical formula 1, an arylamine-based organic substance, or the like can be used, but is not limited thereto.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material as described above. The host material may further contain 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 carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,And bisindenopyrene, etc., wherein 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 arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The above-mentioned electronic regulating layer means the following layer: the organic light-emitting device is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and has an effect of improving the efficiency of the organic light-emitting device by adjusting electron mobility and preventing excessive migration of holes to increase the probability of hole-electron bonding. The electron mediator layer contains an electron mediator, and as examples of such electron mediator, triazine derivatives, triazole derivatives, triazine derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from the electrode and transports the received electrons to the light emitting layer and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the electron modulation layer. Such an electron injection and transport substance is a substance that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a substance having a large mobility of electrons. Examples of the specific electron injection and transport substance include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole (S),The compounds are used together with diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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 organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Synthesis example 1: production of substituent represented by chemical formula 3
In order to introduce the substituent represented by the above chemical formula 3 into the compound represented by the above chemical formula 1, intermediate compounds int.(b 1), int.(b 2) and int.(b 3) are produced by the following reaction formulae 2-1, 2-2 and 2-3, respectively.
[ Reaction type 2-1]
In the above reaction formula 2-1, X' is halogen, and the description of the remaining substituents is the same as that described above. The step 2-1a is a step of introducing a bromo group into the starting material SM1 (b 1), and the step 2-1b is a step of introducing a linking group by a suzuki coupling reaction, thereby producing the intermediate compound int. (b 1). However, when L 2 is a single bond, step 2-1b may be omitted. The specific manufacturing method is as follows.
1) Step 2-1a: production of intermediate compound SM2 (b 1)
After SM1 (b 1) (1 equivalent) was dissolved in THF (excess), the temperature was lowered to-78℃and 2.5M N-BuLi (1 equivalent) was added dropwise thereto, followed by stirring for 3 hours and then N-bromosuccinimide (1 equivalent) was added thereto. Then, the reaction mixture was heated to room temperature and stirred for 10 hours, and 1N HCl (excess) was added to terminate the reaction. After the completion of the reaction, layer separation was performed, and after the solvent was removed, the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the title compound was produced.
2) Step 2-1b: production of intermediate compound int. (b 1)
After adding SM2 (b 1) (1 equivalent) and SM3 (1.02 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate (30 vol% based on THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed to conduct layer separation. After the solvent was removed, vacuum distillation was performed, and recrystallization was performed with ethyl acetate and hexane, thereby obtaining the title compound.
[ Reaction type 2-2]
In the above reaction formula 2-2, X' is halogen, and the description of the remaining substituents is the same as that described above. The above step 2-2a is a step of introducing a bromo group into the starting material SM1 (b 2), and the above step 2-2b is a step of introducing a linking group by a suzuki coupling reaction, thereby producing the intermediate compound int. (b 2). However, when L 2 is a single bond, step 2-2b may be omitted. The specific manufacturing method is as follows:
1) Step 2-2a: production of intermediate compound SM2 (b 2)
After SM1 (b 2) (1 equivalent) was dissolved in DMF (excess), the temperature was lowered to 0℃and after stabilization, N-bromosuccinimide (1 equivalent) was added. Then, the reaction mixture was heated to room temperature, stirred for 1 hour, and then 1N HCl (excess) was added to terminate the reaction. After the completion of the reaction, layer separation was performed, and after the solvent was removed, the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the title compound was obtained.
2) Step 2-2b: production of intermediate compound int. (b 2)
The title compound was obtained in the same manner as in the above-described step 2-1b except that SM2 (b 2) was used as the starting material in place of SM2 (b 1) in the above-described step 2-1 b.
[ Reaction type 2-3]
In the above reaction formulae 2 to 3, X' is halogen, and the description of the remaining substituents is the same as that described above. The above step 2-3 is a step of introducing a linking group by a suzuki coupling reaction to produce the intermediate compound int. (b 3). In this case, starting material SM1 (b 3) can be produced by a known method in journals "Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists(Journal of Medicinal Chemistry,1997,vol.40,#3,p.322-330)" and "Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals(Tetrahedron,2015,vol.71,#29,p.4835-4841)", etc., and when L 2 is a single bond, step 2-3 can be omitted. The specific manufacturing method is as follows.
1) Step 2-3: production of intermediate compound int. (b 3)
The title compound was obtained in the same manner as in the above-described step 2-1b except that SM1 (b 3) was used as the starting material instead of SM2 (b 1) in the above-described step 2-1 b.
Using the methods of the above reaction formulae 2-1 to 2-3, intermediate compounds of the following Table 1 were obtained, and the respective yields and MS data are shown below.
TABLE 1
Synthesis example 2: production of Compounds 1 to 37 represented by chemical formula 1
The compound represented by the above chemical formula 1 is produced by the following reaction formula 3.
[ Reaction type 3]
In the above reaction formula 3, X' is each independently halogen, T is a reactive group for suzuki coupling reaction, preferably, -B (OH) 2, and the description of the remaining substituents is the same as the description above. The above step 1-1-1 is a step of introducing a substituent L 2 -B into a primary amine by a bloch-wald reaction to produce an intermediate compound int.x, the above step 1-1-2 is a step of introducing a substituent B by a suzuki coupling reaction to produce an intermediate compound int.x, and the above step 1-1-3 is a step of producing an intermediate compound int.x by a suzuki coupling reaction with the same substituent B and substituent Ar. Then, step 1-2 is a step of introducing substituent-L 1 -a into intermediate compound int.x to produce the final compound represented by chemical formula 1.
In this case, a compound INT.Y for introducing the substituent-L 1 -A was produced by the following reaction scheme 4. However, when L 1 is a single bond, step 3 in reaction scheme 4 is omitted.
[ Reaction type 4]
In the above reaction formula 4, X' is each independently halogen, T is a reactive group for suzuki coupling reaction, preferably, -B (OH) 2, and the description of the remaining substituents is the same as the description above.
Next, a specific manufacturing method of each step will be described.
1) Step 1-1-1: production of intermediate compounds INT.X (X1 to X33)
SM1-1 (1 equivalent) and SM2-1 (1.02 equivalent), sodium t-butoxide (1.4 equivalent) were added to xylene, and after heating and stirring, the mixture was refluxed, and [ bis (tri-t-butylphosphine) ] palladium (1 mol%) was added. Then, the temperature was lowered to normal temperature, and after completion of the reaction, the intermediate compounds X1 to X33 were obtained by recrystallization using tetrahydrofuran and ethyl acetate, and the respective yields, MS data, and structures of the produced intermediate compounds X1 to X33 are shown in table 2 below.
2) Step 1-1-2: production of intermediate compound INT.X (X34 and X35)
In the above step 2-1b, intermediate compounds X34 and X35 were obtained in the same manner as in the above step 2-1b except that compounds SM1-2 and SM2-2 were used as starting materials in place of compounds SM2 (b 1) and SM3, respectively, and the respective yields, MS data, and structures of the intermediate compounds X34 and X35 produced were shown in Table 2 below.
3) Step 1-1-3: production of intermediate compound INT.X (36)
In the above step 2-1b, an intermediate compound X36 was obtained in the same manner as in the above step 2-1b except that the compounds SM1-3 and SM2-2 were used as starting materials in place of the compounds SM2 (b 1) and SM3, respectively, and the respective yields, MS data and structures of the intermediate compound X36 produced were shown in Table 2 below.
TABLE 2
4) Step 3: production of intermediate compounds INT.Y (Y1 to Y8)
In the above step 2-1b, except that compounds SM4 and SM5 were used as starting materials in place of compounds SM2 (b 1) and SM3, respectively, compound int.y was obtained by the same method as in the above step 2-1b, and the respective yields, MS data, and structures of the intermediate compounds Y1 to Y8 produced are shown in table 3 below.
TABLE 3
5) Step 1-2: production of final Compounds 1 to 37
Intermediate compounds int.x (1 equivalent) and int.y (1.02 equivalent), sodium t-butoxide (1.4 equivalent) were added to xylene, heated under stirring, refluxed, and palladium [ bis (tri-t-butylphosphine) ] added (1 mol%). Then, the temperature was lowered to room temperature, and after completion of the reaction, recrystallization was performed using tetrahydrofuran and ethyl acetate, whereby the following final compounds 1 to 37 were obtained, and the respective yields and MS data are shown in table 4.
TABLE 4
Example 1: OLED fabrication
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazabenzophenanthrene, hexanitrile hexaazatriphenylene) was depositedAnd performing thermal vacuum evaporation to form a hole injection layer. Compound 2 synthesized in synthesis example 2 above as a hole-transporting substance on the hole-injecting layerAfter vacuum evaporation, HT2 is deposited as a film thickness on the hole transport layerVacuum deposition is performed to form a hole adjusting layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were mixed to form a light-emitting layerVacuum evaporation was performed on the thickness of (c).
Then, E1 compoundEvaporating to form an electronic control layer, evaporating E2 compound and Liq at a ratio of 1:1 (wt%)Thereby sequentially performing thermal vacuum evaporation to form an electron injection and transport layer. Sequentially evaporating on the electron injection and transport layerThickness of lithium fluoride (LiF) andAluminum is formed in a thickness to form a cathode, thereby manufacturing an organic light emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedPer second, lithium fluoride maintenanceVapor deposition rate per second, aluminum maintenanceVapor deposition rate per second.
Examples 2 to 10 and comparative examples 1 to 4
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 5 below was used instead of the compound 2 used in the hole transport layer and the compound HT2 used in the hole adjustment layer.
The compounds used in the above examples and comparative examples are shown below.
Experimental example 1
When current was applied to the organic light emitting devices manufactured in the above examples 1 to 10 and comparative examples 1 to 4, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 5 below. At this time, T95 means a time required for the luminance to decrease from the initial luminance to 95%.
TABLE 5
As shown in table 5 above, it was confirmed that the organic light-emitting device using the compound of the present invention as a hole transport layer substance smoothly injected into the light-emitting layer through holes and the balance of holes and electrons of the organic light-emitting device according to the chemical structure, thereby exhibiting excellent characteristics in terms of driving voltage, efficiency and lifetime as compared with the organic light-emitting device using the compound of the comparative example as a hole transport layer substance.
Example 11: OLED fabrication
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of feiher company, and distilled water was filtered 2 times by a filter manufactured by milbo company. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazabenzophenanthrene, hexanitrile hexaazatriphenylene) was depositedAnd performing thermal vacuum evaporation to form a hole injection layer. HT1 as a hole transporting substance on the hole injection layerAfter vacuum deposition, compound 1 synthesized in synthesis example 2 was deposited as a film thickness on the hole transport layerVacuum deposition is performed to form a hole adjusting layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were mixed to form a light-emitting layerVacuum evaporation was performed on the thickness of (c).
Then, E1 compoundAfter vapor deposition to form an electronic control layer, an E2 compound and Liq were vapor deposited at a ratio (wt%) of 1:1Thereby sequentially performing thermal vacuum evaporation to form an electron injection and transport layer. Sequentially evaporating on the electron injection and transport layerThickness of lithium fluoride (LiF) andAluminum is formed in a thickness to form a cathode, thereby manufacturing an organic light emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedPer second, lithium fluoride maintenanceVapor deposition rate per second, aluminum maintenanceVapor deposition rate per second.
Examples 12 to 43 and comparative examples 5 to 9
An organic light-emitting device was manufactured in the same manner as in example 11 above, except that the compound described in table 6 below was used instead of the compound HT1 used in the hole transport layer and the compound 1 used in the hole adjustment layer.
Experimental example 2
When electric current was applied to the organic light emitting devices manufactured in examples 11 to 43 and comparative examples 5 to 9 described above, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 6 below. At this time, T95 means a time required for the luminance to decrease from the initial luminance to 95%.
TABLE 6
As shown in table 6 above, it was confirmed that the organic light emitting device using the compound of the present invention as a hole adjusting layer substance or as both a hole adjusting layer substance and a hole transporting layer substance successfully injected into the light emitting layer by holes and the balance of holes and electrons of the organic light emitting device according to the chemical structure, thereby exhibiting excellent characteristics in terms of driving voltage, efficiency and lifetime as compared to the organic light emitting device using the compound of the comparative example.
[ Description of the symbols ]
1: Substrate 2: anode
3: Hole transport layer 4: light-emitting layer
5: Electron injection and transport layer 6: cathode electrode
7: Hole injection layer 8: hole regulating layer
9: An electronically modulating layer.
Claims (7)
1. A compound represented by the following chemical formula 1:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 to L 3 are each independently a single bond; or C 6-20 arylene substituted or unsubstituted with deuterium or C 1-10 alkyl,
A is a substituent represented by the following chemical formula 2-1,
Chemical formula 2-1
In the chemical formula 2-1 described above,
T 1 to T 4 are each independently a benzene ring, a naphthalene ring, a phenanthrene ring or a dibenzofuran ring,
W 1 is O, S, NR 5 or CR 6R7,
One of R 1 to R 5 is combined with L 1, the remainder are each independently hydrogen, deuterium, tri (C 1-4 alkyl) silyl, C 1-10 alkyl or C 6-20 aryl, or R 5 is combined with an adjacent substituent R 1 to form an indole ring,
R 6 and R 7 are each independently C 1-10 alkyl or C 6-20 aryl, or are combined with one another to form a fluorene spiro ring,
B is a substituent represented by any one of the following chemical formulas B1 to B3,
Ar is a substituent represented by any one of the following chemical formulas b1 to b 3; any aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spiro [ cyclopentane-1, 9 '-fluorenyl ] group and spiro [ cyclohexane-1, 9' -fluorenyl ] group; or any heteroaryl group selected from dibenzofuranyl, dibenzothienyl and carbazolyl, wherein the aryl and heteroaryl groups are each independently optionally substituted with 1 to 5 substituents each independently selected from deuterium, trimethylsilyl, triphenylsilyl, C 1-10 alkyl and C 6-20 aryl,
In the chemical formulas b1 to b3,
X is O or S, and the X is O or S,
Z 1 and Z 2 are each independently hydrogen, C 1-10 alkyl, C 6-20 aryl, or C 2-20 heteroaryl comprising O or S,
Z 3 is hydrogen, deuterium, tri (C 1-4 alkyl) silyl, C 1-10 alkyl, C 6-20 aryl, or C 2-20 heteroaryl containing O or S,
M is 1,2, 3 or 4.
2. The compound of claim 1, wherein each of L 1 to L 3 is independently a single bond, phenylene, biphenyldiyl, naphthylene, or 9, 9-dimethyl-9H-fluorenylene.
3. The compound according to claim 1, wherein a is represented by any one of the following chemical formulas a1 to a 16:
In the chemical formulas a1 to a16,
W 3 is O or S, and the total number of the components is equal to the total number of the components,
W 4 is O, S, N (phenyl) or C (methyl) 2,
One of R is combined with L 1, the rest is hydrogen,
R 3 is hydrogen, phenyl, biphenyl or trimethylsilyl,
R 5 is phenyl, naphthyl or biphenyl,
R 6 and R 7 are each independently methyl, ethyl, hexyl or phenyl.
4. The compound of claim 1, wherein Z 1 and Z 2 are each independently hydrogen, methyl, ethyl, isopropyl, phenyl, biphenyl, naphthyl or dibenzofuranyl,
Z 3 is hydrogen, deuterium, trimethylsilyl, methyl, isopropyl, phenyl, naphthyl or dibenzofuranyl.
5. The compound according to claim 1, wherein Ar is a substituent represented by any one of the chemical formulas b1 to b3, or any one selected from the following groups:
Among the groups of the radicals in which the radicals are formed,
Y is O, S, N (phenyl), C (methyl) (ethyl) or C (methyl) 2,
At the position ofWherein Q is hydrogen or phenyl, inWherein Q is phenyl,
Q' is methyl or phenyl.
6. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
7. an organic light emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 6.
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| KR101781739B1 (en) * | 2015-10-07 | 2017-09-25 | 주식회사 엘지화학 | New compound and organic light emitting device comprising the same |
| KR101985650B1 (en) * | 2015-10-07 | 2019-09-03 | 주식회사 엘지화학 | Double spiro structured compound and organic light emitting device comprising the same |
| KR102620119B1 (en) * | 2016-02-15 | 2024-01-03 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| KR102120516B1 (en) * | 2016-04-12 | 2020-06-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device using the same |
| KR101910498B1 (en) * | 2016-06-08 | 2018-10-22 | (주)씨엠디엘 | The novel organic electroluminescent compounds and organic electroluminescent device including the same |
| KR102103620B1 (en) * | 2016-09-06 | 2020-04-22 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| JP2020097525A (en) * | 2017-03-10 | 2020-06-25 | 出光興産株式会社 | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic apparatus |
| KR102080288B1 (en) * | 2017-05-22 | 2020-02-21 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR102220220B1 (en) * | 2017-06-14 | 2021-02-24 | 솔루스첨단소재 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
-
2019
- 2019-02-15 KR KR1020190017984A patent/KR102475856B1/en active IP Right Grant
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2020
- 2020-02-05 WO PCT/KR2020/001675 patent/WO2020166875A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170031614A (en) * | 2015-09-10 | 2017-03-21 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102475856B1 (en) | 2022-12-08 |
| CN113227082A (en) | 2021-08-06 |
| WO2020166875A1 (en) | 2020-08-20 |
| KR20200100241A (en) | 2020-08-26 |
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