CN110800122A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN110800122A CN110800122A CN201880042379.9A CN201880042379A CN110800122A CN 110800122 A CN110800122 A CN 110800122A CN 201880042379 A CN201880042379 A CN 201880042379A CN 110800122 A CN110800122 A CN 110800122A
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- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000003118 aryl group Chemical group 0.000 claims description 89
- 239000000126 substance Substances 0.000 claims description 75
- -1 dibenzofuranyl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 18
- 125000002560 nitrile group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 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 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000010410 layer Substances 0.000 description 68
- 239000007787 solid Substances 0.000 description 44
- 125000004432 carbon atom Chemical group C* 0.000 description 38
- 238000004519 manufacturing process Methods 0.000 description 36
- 238000004949 mass spectrometry Methods 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 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 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 235000010290 biphenyl Nutrition 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 238000001914 filtration Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- MJDDVTZXYXHTRY-UHFFFAOYSA-N 4-chloro-2,6-diphenylpyrimidine Chemical compound N=1C(Cl)=CC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MJDDVTZXYXHTRY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052702 rhenium Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- UBDNTMGXEDBQJN-UHFFFAOYSA-N 2-[4-bromo-3-(2-chlorophenyl)phenyl]triphenylene Chemical group BrC1=CC=C(C=C1C1=C(C=CC=C1)Cl)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C2C=C1 UBDNTMGXEDBQJN-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JYPNATRORXQZLM-UHFFFAOYSA-N 4-bromo-2-(2-chlorophenyl)aniline Chemical compound NC1=CC=C(Br)C=C1C1=CC=CC=C1Cl JYPNATRORXQZLM-UHFFFAOYSA-N 0.000 description 1
- HHTYEQWCHQEJNV-UHFFFAOYSA-N 4-bromo-2-iodoaniline Chemical compound NC1=CC=C(Br)C=C1I HHTYEQWCHQEJNV-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- YTPFHXMKVQXVII-UHFFFAOYSA-N C1=2C=CC=CC1=C1C(=C3C=CC=CC=23)C=C(C2=CC=C(N)C(C3=CC=CC=C3Cl)=C2)C=C1 Chemical compound C1=2C=CC=CC1=C1C(=C3C=CC=CC=23)C=C(C2=CC=C(N)C(C3=CC=CC=C3Cl)=C2)C=C1 YTPFHXMKVQXVII-UHFFFAOYSA-N 0.000 description 1
- QKWDJBMXMFMKDD-UHFFFAOYSA-N C1=C(N2C3=C(C4=CC=CC=C24)C=C(C2=CC=C(Br)C(C4=CC=CC=C4Cl)=C2)C=C3)C=CC=C1 Chemical compound C1=C(N2C3=C(C4=CC=CC=C24)C=C(C2=CC=C(Br)C(C4=CC=CC=C4Cl)=C2)C=C3)C=CC=C1 QKWDJBMXMFMKDD-UHFFFAOYSA-N 0.000 description 1
- XOHDZVRXUBDGLE-UHFFFAOYSA-N C1=CC=2N(C3=C(C=2C=C1)C=CC=C3)C1=CC(=C(C=C1)N)C1=C(C=CC=C1)Cl Chemical compound C1=CC=2N(C3=C(C=2C=C1)C=CC=C3)C1=CC(=C(C=C1)N)C1=C(C=CC=C1)Cl XOHDZVRXUBDGLE-UHFFFAOYSA-N 0.000 description 1
- JALXBQRVLQQENB-UHFFFAOYSA-N C1=CC=C2C(=C1)N(C1=C2C=CC=C1)C1=CC(=C(C=C1)Br)C1=C(C=CC=C1)Cl Chemical compound C1=CC=C2C(=C1)N(C1=C2C=CC=C1)C1=CC(=C(C=C1)Br)C1=C(C=CC=C1)Cl JALXBQRVLQQENB-UHFFFAOYSA-N 0.000 description 1
- BYXTWQJPBGTCEB-UHFFFAOYSA-N C1=CC=CC=C1N1C2=C(C3=CC=CC=C13)C=C(C1=CC=C(N)C(C3=CC=CC=C3Cl)=C1)C=C2 Chemical compound C1=CC=CC=C1N1C2=C(C3=CC=CC=C13)C=C(C1=CC=C(N)C(C3=CC=CC=C3Cl)=C1)C=C2 BYXTWQJPBGTCEB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 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
- 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
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 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
- 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 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
- 230000000903 blocking effect Effects 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005240 diheteroarylamino group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-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
- 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
- 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
- 230000003287 optical effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 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
- 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
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 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
- 229910052711 selenium Inorganic materials 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 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
- 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
- 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract
The present specification relates to an organic electroluminescent device.
Description
Technical Field
The present invention claims priority based on korean patent application No. 10-2017-.
The present description relates to organic light emitting devices.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.
There is a continuing demand for the development of new materials for organic electroluminescent devices as described above.
Disclosure of Invention
Technical subject
The present specification provides an organic electroluminescent device.
Means for solving the problems
There is provided an organic electroluminescent device comprising: the light-emitting device includes an anode, a cathode provided to face the anode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a first host represented by chemical formula 1 and a second host represented by chemical formula 2.
[ chemical formula 1]
In the chemical formula 1 described above,
r3 is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituent of the following chemical formula 3,
[ chemical formula 2]
[ chemical formula 3]
In the above-mentioned chemical formulas 1 to 3,
r1, R2 and R4 to R7, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
x1 to X7, which are the same or different from each other, are each independently CRa or N,
y1 and Y2, which are identical to or different from one another, are each independently CRbRc, NRd, O or S,
y3 is CReRf, NRg, O or S,
l is a direct bond, or a substituted or unsubstituted arylene group,
ra is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted aryl, heteroaryl, arylthio
Or an aryloxy group, or a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with R4,
rb to Rg, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted aryl group, or a heteroaryl group,
a is an integer of 0 to 8,
b. e and f are each an integer of 0 to 7,
c is an integer of 0 or 1,
d is an integer of 0 to 2,
g is an integer of 0 to 5,
b + c is an integer of 0 to 7,
a. and b, d, e, f and g are plural, R1, R2 and R4 to R7 are the same or different from each other and each is independent.
Effects of the invention
The organic electroluminescent device according to an embodiment of the present specification may use the compounds of chemical formulas 1 and 2 as materials of an organic layer, and by using the compounds of chemical formulas 1 and 2, an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics may be achieved in the organic electroluminescent device.
In detail, when the compound represented by the above chemical formula 1 is used as a single host in a light emitting layer, a difference in HOMO level from an adjacent hole transport layer is large, a barrier (barrier) to holes is generated, and hole transfer to the light emitting layer is not easily achieved, and a light emitting region is formed adjacent to the hole transport layer. For this reason, holes are not balanced with electrons and efficiency and lifetime are reduced. Therefore, by using the second host compound represented by the above chemical formula 2 of a hole transport type together, efficiency and lifetime of the organic light emitting device can be improved.
Drawings
Fig. 1 illustrates an organic electroluminescent device according to an embodiment of the present specification.
FIG. 2 shows the results of liquid chromatography analysis of Compound 1A.
FIG. 3 is the result of mass spectrometry of Compound 1A.
[ description of symbols ]
1: substrate
2: anode
3: organic material layer
4: cathode electrode
Detailed Description
The present specification will be described in more detail below.
The present specification provides an organic electroluminescent device comprising: the light-emitting device includes an anode, a cathode provided to face the anode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a first host represented by chemical formula 1 and a second host represented by chemical formula 2.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.
In the present specification, examples of the substituent are described below, but not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
The term "substituted or unsubstituted" in the present specification means that the substituent is substituted with 1 or 2 or more substituents selected from deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are bonded" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a perylene group,
and a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted, it may be 
And the like. But is not limited thereto.
In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.
In the present specification, the aryl group in the N-arylalkylamino group and the N-arylheteroarylamino group is the same as the above-mentioned aryl group.
In the present specification, the heteroaryl group includes one or more heteroatoms other than carbon atoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzeneAnd furyl, phenanthrolinyl, isofuranyl, phenanthrolinyl
Examples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. Heteroarylamine groups comprising more than 2 of the above-described heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or may comprise both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the above-mentioned heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
In the present specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those exemplified above for the heteroaryl group.
In the present specification, the aryl group can be applied to the above description except that the arylene group is a 2-valent group.
In this specification, the description above for heteroaryl may be applied to heteroarylene groups, except that heteroarylene groups are 2-valent groups.
According to an embodiment of the present disclosure, the chemical formula 1 is any one of the following chemical formulas 4 to 6.
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
In the above-mentioned chemical formulas 4 to 6,
ar is a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylene group,
x6 and X7, which are the same or different from each other, are each independently CRh or N,
y4 is NRi or O,
r8 is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
rh and Ri, equal to or different from each other, are each independently hydrogen, or a substituted or unsubstituted aryl group,
h is an integer of from 0 to 4,
g1 is an integer from 0 to 3,
r1 to R4, R7, X1 to X4, a to d, g, and Ra to Rd are defined as the above chemical formulae 1 and 3.
According to an embodiment of the present disclosure, R1 and R2 are the same or different from each other and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, R1 and R2 are the same or different from each other and each independently hydrogen, deuterium, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group.
According to an embodiment of the present disclosure, R1 and R2 are hydrogen.
According to an embodiment of the present disclosure, R3 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, R3 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R3 is an aryl group substituted or unsubstituted with an alkyl group.
According to one embodiment of the present specification, R3 represents a phenyl group substituted or unsubstituted with an alkyl group, a biphenyl group substituted or unsubstituted with an alkyl group, a terphenyl group substituted or unsubstituted with an alkyl group, a phenanthryl group substituted or unsubstituted with an alkyl group, a triphenylene group substituted or unsubstituted with an alkyl group, or a fluorenyl group substituted or unsubstituted with an alkyl group.
According to an embodiment of the present specification, R3 is a phenyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a triphenylene group, or a dimethylfluorenyl group.
According to an embodiment of the present disclosure, R3 is substituted or unsubstituted heteroaryl.
According to an embodiment of the present disclosure, R3 is a substituted or unsubstituted heteroaryl group containing N, O, or S.
According to an embodiment of the present disclosure, R3 is a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.
According to an embodiment of the present specification, R3 is a substituted or unsubstituted carbazolyl group.
According to an embodiment of the present disclosure, R3 is a carbazolyl group substituted or unsubstituted with an aryl group substituted or unsubstituted with deuterium, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group.
According to an embodiment of the present specification, R3 is a carbazolyl group substituted or unsubstituted with a phenyl group substituted or unsubstituted with a deuterium group or a nitrile group.
According to an embodiment of the present specification, R3 is a carbazolyl group substituted or unsubstituted with a phenyl group, a tert-butyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
According to an embodiment of the present specification, R3 is a carbazolyl group substituted with or unsubstituted with a naphthyl group.
According to an embodiment of the present specification, R3 is a carbazolyl group substituted or unsubstituted with a dibenzofuranyl group or a dibenzothiophenyl group.
According to an embodiment of the present disclosure, R3 may be selected from the following substituents, and the selected substituents may be substituted with a phenyl group or unsubstituted.
According to an embodiment of the present specification, R4 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present disclosure, R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, R4 is an aryl group substituted or unsubstituted with an aryl group, or a heteroaryl group substituted or unsubstituted with an aryl group.
According to an embodiment of the present specification, R4 is an aryl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or a heteroaryl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R4 represents an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R4 represents an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a phenyl group or a heteroaryl group having 6 to 20 carbon atoms substituted or unsubstituted with a phenyl group.
According to an embodiment of the present specification, R4 is a phenyl group substituted or unsubstituted by a phenyl group, a biphenyl group, a pyridyl group, a dibenzofuranyl group substituted or unsubstituted by a phenyl group, or a dibenzothiophenyl group substituted or unsubstituted by a phenyl group.
According to an embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present disclosure, R5 and R6 are the same or different from each other and each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, R5 and R6 are the same or different from each other and each independently hydrogen, deuterium, a silyl group substituted or unsubstituted with an aryl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently represents hydrogen, deuterium, a silyl group substituted with an aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R5 and R6 are the same as or different from each other, and each independently represents hydrogen, deuterium, a silyl group substituted or unsubstituted with a phenyl group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present disclosure, R5 and R6 are the same or different and each independently hydrogen, deuterium, triphenylsilyl, phenyl, biphenyl, terphenyl, or naphthyl.
According to an embodiment of the present specification, R7 is hydrogen, or is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present specification, R7 represents hydrogen or forms a heterocyclic ring substituted with or unsubstituted by an aryl group in combination with an adjacent group.
According to an embodiment of the present specification, R7 represents hydrogen, or is bonded to an adjacent group to form a heterocyclic ring which is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R7 represents hydrogen or forms a heterocyclic ring substituted or unsubstituted with a phenyl group by bonding to an adjacent group.
According to an embodiment of the present specification, R7 is hydrogen or is bonded to an adjacent group to form an N-containing heterocyclic ring substituted or unsubstituted with a phenyl group.
According to an embodiment of the present disclosure, the X1 to X7 are the same or different and each is independently CRa or N.
According to an embodiment of the present disclosure, at least one of X1 to X3 is N.
According to an embodiment of the present disclosure, all of X1 to X3 are CRa.
According to an embodiment of the present disclosure, Ra is hydrogen.
According to an embodiment of the present disclosure, Ra is an arylthio group or an aryloxy group.
According to an embodiment of the present specification, Ra and R4 adjacent thereto are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present specification, Ra and R4 adjacent thereto are bonded to each other to form Ra
The dotted line represents a site bonded to the benzene ring of the nucleus.
According to an embodiment of the present disclosure, Y1 and Y2 are the same or different and each independently CRbRc, NRd, or O.
According to an embodiment of the present disclosure, Y1 and Y2 are the same or different and each independently NRd.
According to one embodiment of the present disclosure, Y3 is CReRf, NRg, O, or S.
According to an embodiment of the present disclosure, Y4 is NRi or O.
According to an embodiment of the present disclosure, Rb and Rc are hydrogen.
According to an embodiment of the present disclosure, Rd is hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
According to an embodiment of the present disclosure, Rd is hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted silyl group.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a halogen group, an alkyl group, a substituted or unsubstituted aryl group, or a silyl group which is substituted or unsubstituted with an aryl group.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with F, Cl, Br, I, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a silyl group which is substituted or unsubstituted with a phenyl group.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with a triphenylsilyl group.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; aryl of 6 to 20 carbon atoms substituted or unsubstituted with F, Cl, Br, I, methyl, phenyl, biphenyl, naphthyl, or triphenylsilyl.
According to an embodiment of the present disclosure, Rd is hydrogen; deuterium; phenyl unsubstituted or substituted by F, methyl, phenyl, biphenyl, naphthyl, or by triphenylsilyl; biphenyl substituted or unsubstituted with F, methyl, phenyl, biphenyl, naphthyl, or triphenylsilyl; terphenyl optionally substituted with F, methyl, phenyl, biphenyl, naphthyl, or triphenylsilyl; fluorenyl substituted or unsubstituted with F, methyl, phenyl, biphenyl, naphthyl, or triphenylsilyl.
According to an embodiment of the present disclosure, Rd is hydrogen.
According to an embodiment of the present disclosure, Rd is phenyl substituted or unsubstituted with F, phenyl, biphenyl, naphthyl, or triphenylsilyl.
According to an embodiment of the present disclosure, Rd is terphenyl.
According to an embodiment of the present disclosure, Rd is phenyl or naphthyl substituted or unsubstituted with triphenylsilyl.
According to an embodiment of the present disclosure, Rd is dimethylfluorenyl.
According to an embodiment of the present specification, the Re and Rf are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, Re and Rf are the same or different from each other and each independently hydrogen, deuterium, or an alkyl group.
According to an embodiment of the present specification, Re and Rf are the same or different from each other and each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, Re and Rf are the same or different from each other, and each independently hydrogen, deuterium, or methyl.
According to an embodiment of the present disclosure, Rg is hydrogen or a substituted or unsubstituted aryl.
According to an embodiment of the present specification, the Rg is hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, the Rg is hydrogen or a substituted or unsubstituted phenyl group.
According to an embodiment of the present disclosure, the Rg is a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, the Rg is a phenyl group substituted or unsubstituted with deuterium, a nitrile group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group, or a heteroaryl group containing O or S.
According to an embodiment of the present disclosure, the Rg is a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a tert-butyl group, a phenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
According to an embodiment of the present disclosure, Rh and Ri are the same or different from each other, and each is independently hydrogen or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, Rh is hydrogen.
According to an embodiment of the present disclosure, Ri is an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present disclosure, Ri is a phenyl group.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L is a direct bond.
According to an embodiment of the present disclosure, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
According to an embodiment of the present specification, L is a phenylene group substituted or unsubstituted with a substituted or unsubstituted silyl group or a substituted or unsubstituted alkyl group; a biphenylene group substituted or unsubstituted with a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group; or a naphthylene group substituted or unsubstituted with a substituted or unsubstituted silyl group or a substituted or unsubstituted alkyl group.
According to an embodiment of the present specification, L is a phenylene group substituted or unsubstituted with a silyl group substituted or unsubstituted with a phenyl group, or an alkyl group having 1 to 10 carbon atoms; a biphenylene group substituted or unsubstituted with a silyl group substituted or unsubstituted with a phenyl group or an alkyl group having 1 to 10 carbon atoms; or a silyl group substituted or unsubstituted with a phenyl group or a naphthylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, L is a phenylene group which is substituted or unsubstituted with a triphenylsilyl group or a methyl group; a biphenylene group; or a naphthylene group.
According to an embodiment of the present disclosure, the chemical formula 1 may be selected from the following compounds.
According to an embodiment of the present disclosure, the chemical formula 2 may be selected from the following compounds.
According to one embodiment of the present disclosure, the compounds of chemical formulas 1 and 2 may be produced according to the following reaction formulae, but are not limited thereto. In the following reaction scheme, the kind and number of substituents may be determined by appropriately selecting known starting materials by those skilled in the art. The kind of reaction and the reaction conditions may be those known in the art.
The compound represented by the above chemical formula 1 may be synthesized by the following method.
X1 to X3 are the same as defined in the above chemical formula 1,
rv to Rx, equal to or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
The compound represented by the above chemical formula 2 may be synthesized by the following method.
Ry and Rz, equal to or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In addition, an organic electroluminescent device according to the present invention is characterized by comprising: the light-emitting device includes an anode, a cathode provided to face the anode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a first host represented by chemical formula 1 and a second host represented by chemical formula 2.
The organic light-emitting device of the present invention can be produced by a method and a material for producing a general organic light-emitting device, in addition to the formation of one or more organic layers using the above-described compound.
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 two 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 a smaller number of organic layers may be included. In addition, the organic layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection, and one or more layers of the layers may include the compound.
The organic layer containing the compound of chemical formula 1 may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, but is not limited thereto and may have a single layer structure. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method using various polymer materials.
For example, the structure of the organic light emitting device of the present invention may have the same structure as that shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a second organic layer 3 including the compound of chemical formula 1 and the compound of chemical formula 2, and a cathode 4 are sequentially stacked on a substrate 1.
In one embodiment of the present invention, the organic layer including the first host and the second host may include at least one of a light emitting layer, an electron injection layer, an electron transport layer, and a layer for simultaneously injecting and transporting electrons, and the light emitting layer of the layers may include the first host and the second host.
In one embodiment of the present invention, the light emitting layer has a thickness of 1: 3 to 3: a weight ratio of 1 comprises a first body and a second body.
In one embodiment of the present invention, the light emitting layer has a thickness of 1: 2 to 2: a weight ratio of 1 comprises a first body and a second body.
In one embodiment of the present invention, the light emitting layer is formed by a combination of 95: 5 to 70: 30 comprises a first body and a second body: a dopant.
In one embodiment of the present invention, the light emitting layer is formed by a combination of 90: 10 to 80: a volume ratio of 20 comprises a first body and a second body: a dopant.
For example, the organic light emitting device according to the present invention may be manufactured as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) to form an anode, and then forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer and an organic layer including a compound of the above chemical formula 1 or the above chemical formula 2 on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO: al or SnO2: a combination of a metal such as Sb and an oxide; of poly (3-methyl compounds), poly [3,4- (ethylene-1, 2-dioxy) compounds]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject 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; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole-injecting substance is a substance that can receive injected holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole-injecting substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and conductive polymers of polymeric compounds.
The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene and redAnd a fluorescent group, but not limited thereto.
The method of manufacturing the compound of chemical formula 1 and the manufacturing of the organic light emitting device using the same are specifically described in the following examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.
In the present invention, an iridium-based phosphorescent dopant may be used as the dopant.
In the present invention, the iridium complex used as a dopant of the light-emitting layer is as follows.
In one embodiment of the present invention, the dopant is contained in a weight ratio of 1 to 20%.
In one embodiment of the present invention, the dopant is contained in a weight ratio of 5 to 15%.
Modes for carrying out the invention
< Synthesis example >
Production of Compound P1
4-bromo-2-iodoaniline (100g, 335.6mmol), 2-chloro-6-fluorophenyl) boronic acid (58.5g, 335.6mmol) were dissolved in 800ml of Tetrahydrofuran (THF). Adding sodium carbonate (Na) thereto2CO3)2M solution (500mL), tetrakis (triphenylphosphine) palladium (0) [ Pd (PPh)3)4](7.7g, 6.7mmol) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to normal temperature, and the resultant mixture was extracted with water and toluene 3 times. After the toluene layer was separated, the filtrate dried over magnesium sulfate (magnesium sulfate) and filtered was distilled under reduced pressure. The concentrated compound was diluted with 10: 1 n-hexane: the ethyl acetate solution was subjected to column chromatography to give 120.0 g. By mass spectrometry of the resulting solid inThe peak was confirmed at 283M/Z.
Production of Compound P2
Reacting 5-bromo-2 '-chloro- [1,1' -biphenyl]-2-amine (100g, 353.9mmol), [1,1' -biphenyl]-4-Ylboronic acid (70.1g, 353.9mmol) was dissolved in 800ml of Tetrahydrofuran (THF). Adding sodium carbonate (Na) thereto2CO3)2M solution (520mL), tetrakis (triphenylphosphine) palladium (0) [ Pd (PPh)3)4](7.7g, 6.7mmol) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to normal temperature, and the resultant mixture was extracted with water and toluene 3 times. After the toluene layer was separated, the filtrate dried over magnesium sulfate (magnesium sulfate) and filtered was distilled under reduced pressure. Then, the mixture was recrystallized from ethanol to obtain 100.8g of Compound P2. A peak was confirmed at M/Z356 by mass spectrometry of the obtained solid.
Production of Compound P3
Then, 47.0g (132mmol) of 2-chloro- [1,1':3',1 ": 4", 1' "-tetrabiphenyl group was added thereto]480mL of glacial acetic acid, 120mL of sulfuric acid, and 120mL of distilled water were added to the-6' -amine, and the mixture was heated. Then, when the solution became a clear solution, the solution was cooled to 3 to 4 ℃ and 120mL of a 1.64M aqueous solution of sodium nitrite was added and stirred for 30 minutes. The above solution was slowly added dropwise at 3 to 4 ℃ to a solution of 32.6g (146mmol) of copper bromide (CuBr)2)96mL of hydrochloric acid (HCl). Then, it was heated to 45 ℃ and stirred for 30 minutes, and heated to 80 ℃ and stirred for 30 minutes. After cooling to room temperature, the organic layer was extracted 3 times with 75mL of chloroform. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water, and the resulting organic layer was washed with anhydrous sodium sulfate (MgSO)4) And (5) drying. Then, after separation by filtration, the solvent was distilled off under reduced pressure and recrystallized from ethanol to obtain 41.0g of compound P3. A peak was confirmed at M/Z420 by mass spectrometry of the obtained solid.
Production of Compound P4
42g (100mmol) of the above 6 '-bromo-2-chloro-1, 1':3',1 ": 4", 1' "-tetrabiphenyl were dissolved in 300ml of anhydrous tetrahydrofuran under nitrogen, and the ambient temperature of the reactor was maintained at-78 ℃. Then, 40ml of 2.5M-butyllithium were slowly added dropwise. After completion of the dropwise addition, stirring was carried out for 30 minutes, and then 22.8g of 9H-xanthen-9-one was dissolved in 200ml of purified tetrahydrofuran and slowly added dropwise. After the reaction solution was stirred for about 1 hour while maintaining the temperature at-78 ℃, the temperature was raised to room temperature and stirring was continued for 12 hours. After the reaction was completed by adding diluted hydrochloric acid to the reaction solution, liquid separation and extraction were performed with dichloromethane. The obtained organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. Subsequently, after adding to 400ml of acetic acid, a catalytic amount of hydrochloric acid was added dropwise, followed by stirring at reflux temperature for 12 hours. After completion of the reaction, the reaction mixture was cooled to obtain a solid, which was then filtered and subjected to column chromatography to obtain 38.2g of compound P4. Peaks were confirmed at M/Z519 by mass spectrometry of the resulting solid.
Production of Compound P5
15.9g (30mmol) of the compound represented by the above-mentioned P4, 8.38g (33mmol) of bis (pinacolato) diboron, 8.83g (90mol) of potassium acetate, and 200mL of 1, 4-bis
After alkylation, 0.86g (1.5mmol) of Pd (dba)2And 0.84g (3.0mmol) of PCy3Dissolved in 20mL of 1, 4-bis
Alkane was added dropwise. After stirring under reflux for 24 hours and cooling to room temperature, 200mL of distilled water was added and extracted 2 times with 200mL of dichloromethane. The organic layer was washed with sodium sulfate (MgSO)4) And (5) drying. Then, after separation by filtration, the solvent was distilled off under reduced pressure, and 10.0g of compound P5 was obtained by silica gel (silica gel) column chromatography. The peak was confirmed at M/Z611 by mass spectrometry of the obtained solid.
Production of Compound 1A
Compound P5(22.6g, 38mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.3g, 38mmol) were dispersed in tetrahydrofuran (150ml), and 2M aqueous potassium carbonate (aq. K) was added2CO3) (58ml, 115mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.45g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was washed with chloroform and ethyl acetateRecrystallization and filtration were carried out, followed by drying to produce 19.2g (70.1%) of compound 1A. A peak was confirmed at M/Z716 by mass spectrometry of the obtained solid.
FIG. 2 shows the results of liquid chromatography analysis of Compound 1A.
FIG. 3 is the result of mass spectrometry of Compound 1A.
Production of Compound 1B
18.8g (69.2%) of Compound 1B was prepared in the same manner as Compound 1A except that 4-chloro-2, 6-diphenylpyrimidine (10.1g, 38mmol) was used. A peak was confirmed at M/Z715 by mass spectrometry of the obtained solid.
Production of Compound P6
Prepared in the same manner as in the compound P2 except that (9-phenyl-9H-carbazol-3-yl) boronic acid (101.6g, 353.9mmol) was used, to obtain 110.4g of the compound P6. A peak was confirmed at M/Z445 by mass spectrometry of the obtained solid.
Production of Compound P7
Then, 42.6g of compound P7 was produced in the same manner as in the production of compound P3, except that 58.7g (132mmol) of 2 '-chloro-5- (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl ] -2-amine was used. A peak was confirmed at M/Z509 by mass spectrometry of the obtained solid.
Production of Compound P8
Then, the same procedure as for the preparation of compound P4 was repeated except for using 50.8g (100mmol) of 3- (6-bromo-2 '-chloro- [1,1' -biphenyl ] -3-yl) -9-phenyl-9H-carbazole, thereby obtaining 29.8g of compound P8. A peak was confirmed at M/Z608 by mass spectrometry of the obtained solid.
Production of Compound P9
Then, production was carried out in the same manner as for the compound P5 except that 18.2g (30mmol) of the compound represented by P8 was used, whereby 9.6g of the compound P9 was obtained. A peak was confirmed at M/Z700 by mass spectrometry of the obtained solid.
Production of Compound 1C
Compound P9(26.6g, 38mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.3g, 38mmol) were dispersed in tetrahydrofuran (150ml), and 2M aqueous potassium carbonate (aq. K) was added2CO3) (58ml, 115mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.45g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered, and then dried to produce 19.2g (49.7%) of compound 1C. A peak was confirmed at M/Z805 by mass spectrometry of the obtained solid.
Production of Compound 1D
14.0g (45.8%) of Compound 1D was prepared in the same manner as Compound 1C except that 4-chloro-2, 6-diphenylpyrimidine (10.1g, 38mmol) was used. A peak was confirmed at M/Z804 by mass spectrometry of the obtained solid.
Production of Compound P11
Compound P10(110.6g, 353.9mmol) was dissolved in 800ml of toluene (tolumen). To this was added sodium tert-butoxide (54.4g, 566.2mmol), bis (tri-tert-butylphosphine) palladium [ Pd (P-tBu)3)2](1.8g, 3.5mmol) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to normal temperature, and the resultant mixture was extracted with water and toluene 3 times. After the toluene layer was separated, it was dried over magnesium sulfate (magnesium sulfate), and the filtered filtrate was distilled under reduced pressure. Then, the mixture was dissolved in 1000ml of methanolAfter palladium/activated carbon was slowly added at room temperature and stirred, 100ml of hydrazine monohydrate was slowly dropped and stirred under reflux for 24 hours. The temperature was lowered to normal temperature, palladium was removed by filtration, and then the organic layer was extracted 3 times with 400mL of chloroform. The organic layer was washed with an aqueous sodium bicarbonate solution and water, and the resulting organic layer was washed with anhydrous sodium sulfate (MgSO)4) Drying is carried out. Then, after separation by filtration, the solvent was distilled off under reduced pressure and recrystallized from ethanol to obtain 36.0g of compound P11. A peak was confirmed at M/Z369 by mass spectrometry of the obtained solid.
Production of Compound P12
Then, 30.6g of compound P12 was obtained in the same manner as that for compound P7, except that 48.7g (132mmol) of 5- (9H-carbazol-9-yl) -2 '-chloro- [1,1' -biphenyl ] -2-amine was used. A peak was confirmed at M/Z433 by mass spectrometry of the obtained solid.
Production of Compound P13
Then, 22.4g of compound P13 was prepared in the same manner as in the case of compound P8, except that 43.3g (100mmol) of 9- (6-bromo-2 '-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole was used. A peak was confirmed at M/Z532 by mass spectrometry of the obtained solid.
Production of Compound P14
Then, production was carried out in the same manner as for the compound P9 except that 16.0g (30mmol) of the compound represented by P13 was used, whereby 8.2g of the compound P15 was obtained. A peak was confirmed at M/Z624 by mass spectrometry of the obtained solid.
Production of Compound 1E
Compound P14(23.7g, 38mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.3g, 38mmol) were dispersed in tetrahydrofuran (150ml), and 2M aqueous potassium carbonate (aq. K) was added2CO3) (58ml, 115mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.45g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered, and then driedThus, 16.8g (60.7%) of Compound 1E was produced. A peak was confirmed at M/Z729 by mass spectrometry of the obtained solid.
Production of Compound 1F
9.0g (31.3%) of Compound 1F was produced in the same manner as in Compound 1E except that 4-chloro-2, 6-diphenylpyrimidine (10.1g, 38mmol) was used. A peak was confirmed at M/Z728 by mass spectrometry of the obtained solid.
Production of Compound P15
The preparation was carried out in the same manner as in the preparation of the compound P2 except that (9-phenyl-9H-carbazol-3-yl) boronic acid (96.3g, 353.9mmol) was used, whereby 98.6g of the compound P15 was obtained. A peak was confirmed at M/Z430 by mass spectrometry of the obtained solid.
Production of Compound P16
Then, the preparation was carried out in the same manner as in the preparation of the compound P3 except for using 56.7g (132mmol) of 2 '-chloro-5- (triphenylen-2-yl) - [1,1' -biphenyl ] -2-amine, thereby preparing 34.2g of the compound P16. A peak was confirmed at M/Z494 by mass spectrometry of the obtained solid.
Production of Compound P17
Then, the same procedures as used for the compound P4 were repeated except for using 49.4g (100mmol) of 2- (6-bromo-2 '-chloro- [1,1' -biphenyl ] -3-yl) triphenylene, to thereby obtain 23.0g of a compound P17. A peak was confirmed at M/Z593 by mass spectrometry of the obtained solid.
Production of Compound P18
Then, production was carried out in the same manner as for the compound P5 except that 17.8g (30mmol) of the compound represented by the compound P17 was used, whereby 9.0g of the compound P18 was obtained. A peak was confirmed at M/Z685 by mass spectrometry of the obtained solid.
Production of Compound 1G
Compound P18(26.0g, 38mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.3g, 38mmol) were dispersed in tetrahydrofuran (150ml), and 2M aqueous potassium carbonate (aq. K) was added2CO3) (58ml, 115mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.45g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered, and then dried to produce 17.8G (59.3%) of compound 1G. A peak was confirmed at M/Z790 by mass spectrometry measurement of the obtained solid.
Production of Compound 1H
9.8G (31.3%) of Compound 1H was produced in the same manner as in Compound 1G except that 4-chloro-2, 6-diphenylpyrimidine (10.1G, 38mmol) was used. A peak was confirmed at M/Z789 by mass spectrometry of the obtained solid.
Production of Compound 2A
The compound 9- ([1,1' -biphenyl)]-3-yl) -3-bromo-9H-carbazole (10.8g, 27mmol) and the compound (9- ([1,1' -biphenyl)]After (9.8g, 27mmol) of (E) -3-yl) -9H-carbazol-3-yl) boronic acid was dispersed in tetrahydrofuran (80ml), 2M aqueous potassium carbonate solution (aq. K) was added2CO3) (40ml, 81mmol) then tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.3g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. Cooling to normal temperature, removing water layer, concentrating under reduced pressure, adding ethyl acetate, stirring under reflux for 1 hr, cooling to room temperature, and filtering to obtain solid. Chloroform was added to the obtained solid, and the mixture was dissolved under reflux, ethyl acetate was added thereto, and 11.2g (65.1%) of the solution was prepared by recrystallizationCompound 2A. A peak was confirmed at M/Z637 by mass spectrometry of the obtained solid.
Production of Compound 2B
The preparation was carried out in the same manner as in the preparation of the compound 2A except that (9-phenyl-9H-carbazol-3-yl) boronic acid (7.8g, 27mmol) was used, whereby 10.6g (70.0%) of the compound 2B was prepared. A peak was confirmed at M/Z561 by mass spectrometry of the obtained solid.
Production of Compound 2C
The compound 9- ([1,1' -biphenyl)]After (10.8g, 27mmol) of (4-yl) -3-bromo-9H-carbazole and (7.8g, 27mmol) of the compound (9-phenyl-9H-carbazol-3-yl) boronic acid were dispersed in tetrahydrofuran (80ml), 2M aqueous potassium carbonate solution (aq. K) was added2CO3) (40ml, 81mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added3)4](0.3g, 1 mol%) was added, stirred and refluxed for 8 hours. Cooling to normal temperature, removing water layer, concentrating under reduced pressure, adding ethyl acetate, stirring under reflux for 1 hr, cooling to room temperature, and filtering to obtain solid. Chloroform was added to the obtained solid, and the mixture was dissolved under reflux, and ethyl acetate was added thereto, thereby producing 9.8g (64.7%) of compound 2C by recrystallization. A peak was confirmed at M/Z561 by mass spectrometry of the obtained solid.
Production of Compound 2D
The compound 9- ([1,1' -biphenyl)]-4-yl) -3-bromo-9H-carbazole (10.8g, 27mmol) and the compound (9- ([1,1' -biphenyl)]After (9.8g, 27mmol) of (E) -3-yl) -9H-carbazol-3-yl) boronic acid was dispersed in tetrahydrofuran (80ml), 2M aqueous potassium carbonate solution (aq. K) was added2CO3) (40ml, 81mmol) and then add IV(triphenylphosphine) Palladium [ Pd (PPh)3)4](0.3g, 1 mol%) was added, stirred and refluxed for 8 hours. Cooling to normal temperature, removing water layer, concentrating under reduced pressure, adding ethyl acetate, stirring under reflux for 1 hr, cooling to room temperature, and filtering to obtain solid. Chloroform was added to the obtained solid, and the mixture was dissolved under reflux, and ethyl acetate was added thereto, thereby producing 7.2g (41.9%) of compound 2D by recrystallization. A peak was confirmed at M/Z637 by mass spectrometry of the obtained solid.
Examples 1 to 16
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the HI-1 compound described below was added
The thickness of (3) is thermally vacuum-evaporated to form a hole injection layer.
On the above hole injection layer, an HT-1 compound is added
The hole transport layer is formed by thermal vacuum evaporation of the thickness of (1), and an HT-2 compound is added to the deposited film
Thickness ofAnd forming an electron blocking layer by vacuum evaporation.
Then, on the HT-2 deposited film, the compound 1 (host) and the compound 2 (dopant) produced above were simultaneously evaporated at a specific volume ratio (ratio shown in table 1) to form a film
The thickness of (3) is determined by co-evaporation of a phosphorescent dopant GD-1 at a volume ratio of 6 to 15% to form a light emitting layer.
On the above-mentioned luminescent layer an ET-1 substance is added
Vacuum evaporation of (2) and further deposition of an ET-2 substance
The electron transport layer and the electron injection layer were formed by co-evaporation of 2 wt% of Li. On the electron injection layer, toAluminum is evaporated to a thickness to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-8And (4) supporting.
Comparative example
Organic light-emitting devices were produced in the same manner as in the above examples, except that the contents of the phosphorescent host material and the dopant were changed as shown in table 1 below when the light-emitting layer was formed. In this case, the host substances A and B used in the comparative examples were asShown below. The organic light emitting devices fabricated in the above examples to comparative examples 1 to 5 were applied with current, and voltage, efficiency, luminance, color coordinates and lifetime were measured, and the results thereof are shown in table 1 below. At this time, T95 indicates that the optical density is to be 20mA/cm2The initial luminance below is set as the time required for the luminance to decrease to 95% at 100%.
Comparative example 1
Reacting compound 1A with
An OLED device was fabricated in the same manner as in the above example, except that the phosphorescent dopant GD-1 was co-evaporated at a weight ratio of 10%.
Comparative example 2
Reacting compound A with
An OLED device was fabricated in the same manner as in the above example, except that the phosphorescent dopant GD-1 was co-evaporated at a weight ratio of 10%.
Comparative example 3
Compound B and compound PH-1 were mixed at a ratio of 1: 1 by simultaneous evaporation in the presence of a solvent
An OLED device was fabricated in the same manner as in the above example, except that the thickness was evaporated and the phosphorescent dopant GD-1 was co-evaporated at a weight ratio of 15%.
Comparative example 4
Mixing compound 1A and compound 1B in a ratio of 1: 1 by simultaneous evaporation in the presence of a solvent
An OLED device was fabricated in the same manner as in the above example, except that the thickness was evaporated and the phosphorescent dopant GD-1 was co-evaporated at a weight ratio of 12%.
Comparative example 5
Reacting a compound 2A withCompound 2B was prepared as a 1: 1 by simultaneous evaporation in the presence of a solvent
An OLED device was fabricated in the same manner as in the above example, except that the thickness was evaporated and the phosphorescent dopant GD-1 was co-evaporated at a weight ratio of 10%.
The organic light-emitting devices produced in example 1 and comparative examples 1 to 5 were measured for voltage, EGE, color coordinate, and lifetime, and the results are shown in table 1 below.
EGE is measured at a current density of 10mA/cm2The spectral radiance spectrum was measured by a spectral radiance meter CS-1000 (manufactured by Konica Minolta Co., Ltd.) when a voltage was applied to the device. Based on the obtained spectral radiance spectrum, it is assumed that lambertian radiation is applied, and the external quantum efficiency is calculated.
[ Table 1]
In table 1 above, in examples 1 to 16, the light-emitting layer was prepared by mixing compound 1A and compound 2A in the ratio of 1: 1
By volume ratio of
The dopant (GD) is used by doping at a ratio of 12% of the total volume of the host and the dopant. Comparative example 4 was conducted using compound 1A and compound 1B in place of compound 1A and compound 2A as the host, and comparative example 5 was conducted using compound 2A and compound 2B in place of compound 1A and compound 2A as the host. It is understood that examples 1 to 16 have about 40% lower voltage, about 64% higher EQE, and about 1170% higher lifetime, compared with comparative examples 4 and 5.
Claims (6)
1. An organic electroluminescent device comprising: an anode, a cathode provided so as to face the anode, and a light-emitting layer provided between the anode and the cathode, wherein the light-emitting layer includes a first host represented by the following chemical formula 1 and a second host represented by the following chemical formula 2:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
r3 is a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituent of the following chemical formula 3,
chemical formula 2
Chemical formula 3
In the chemical formulae 1 to 3,
in the chemical formulae 1 to 3,
r1, R2 and R4 to R7, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
x1 to X7, which are the same or different from each other, are each independently CRa or N,
y1 and Y2, which are identical to or different from one another, are each independently CRbRc, NRd, O or S,
y3 is CReRf, NRg, O or S,
l is a direct bond, or a substituted or unsubstituted arylene group,
ra is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted aryl, heteroaryl, arylthio, or aryloxy group, or combines with R4 to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
rb to Rg, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted aryl group, or a heteroaryl group,
a is an integer of 0 to 8,
b. e and f are each an integer of 0 to 7,
c is an integer of 0 or 1,
d is an integer of 0 to 2,
g is an integer of 0 to 5,
b + c is an integer of 0 to 7,
a. and b, d, e, f and g are plural, R1, R2 and R4 to R7 are the same or different from each other and each is independent.
2. The organic electroluminescent device according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 4 to 6:
chemical formula 4
Chemical formula 5
Chemical formula 6
In the chemical formulae 4 to 6,
ar is a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylene group,
x6 and X7, which are the same or different from each other, are each independently CRh or N,
y4 is NRi or O,
r8 is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
rh and Ri, equal to or different from each other, are each independently hydrogen, or a substituted or unsubstituted aryl group,
h is an integer of from 0 to 4,
g1 is an integer from 0 to 3,
r1 to R4, R7, X1 to X4, a to d, g, and Ra to Rd are defined the same as those of the chemical formulae 1 and 3.
3. The organic electroluminescent device according to claim 1, wherein R4 is a phenyl group, a biphenyl group, a pyridyl group, a dibenzofuranyl group substituted or unsubstituted with a phenyl group, or a dibenzothiophenyl group substituted or unsubstituted with a phenyl group, or forms a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with Ra or an adjacent group.
4. The organic electroluminescent device according to claim 1, wherein the first host represented by the chemical formula 1 is selected from the following compounds:
5. the organic electroluminescent device according to claim 1, wherein the second host represented by the chemical formula 2 is selected from the following compounds:
6. the organic light emitting device of claim 1, wherein the light emitting layer is doped at a ratio of 95: 5 to 70: 30 comprises a first body and a second body: a dopant.
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