CN111683947B - Heterocyclic compound and organic light-emitting device comprising same - Google Patents
Heterocyclic compound and organic light-emitting device comprising same Download PDFInfo
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- CN111683947B CN111683947B CN201980011994.8A CN201980011994A CN111683947B CN 111683947 B CN111683947 B CN 111683947B CN 201980011994 A CN201980011994 A CN 201980011994A CN 111683947 B CN111683947 B CN 111683947B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 28
- 239000010410 layer Substances 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- -1 dibenzofuranyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 239000012044 organic layer Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 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 19
- 125000005561 phenanthryl group Chemical group 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000006267 biphenyl group Chemical group 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 239000004305 biphenyl Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 24
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 10
- 229910052805 deuterium Inorganic materials 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 125000002560 nitrile group Chemical group 0.000 description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 230000005525 hole transport Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 6
- 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 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 125000001725 pyrenyl group Chemical group 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NYBYXXFMCVWVHH-UHFFFAOYSA-N phosphanyloxyphosphane Chemical group POP NYBYXXFMCVWVHH-UHFFFAOYSA-N 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- UCAKTFSAEMHJJE-UHFFFAOYSA-N (3-chloro-2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1O UCAKTFSAEMHJJE-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PAAYRJZYEDMGIR-UHFFFAOYSA-N ClC1=C(C=CC=C1F)OB(O)O Chemical compound ClC1=C(C=CC=C1F)OB(O)O PAAYRJZYEDMGIR-UHFFFAOYSA-N 0.000 description 1
- QORHAIJZPYYAGW-UHFFFAOYSA-N ClC1=CC(C(C2=CC=CC=C2)=CC=C2)=C2S1 Chemical compound ClC1=CC(C(C2=CC=CC=C2)=CC=C2)=C2S1 QORHAIJZPYYAGW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 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
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 238000010586 diagram Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000000203 mixture Substances 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 125000002098 pyridazinyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 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
- 239000002356 single layer Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- 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
-
- 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
Abstract
The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light-emitting device including the same.
Description
Technical Field
The present invention claims priority from korean patent application No. 10-2018-0061010, filed in the korean patent office on 5.29 of 2018, the entire contents of which are incorporated herein.
The present specification relates to heterocyclic compounds and organic light-emitting devices including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides heterocyclic compounds and organic light-emitting devices comprising the same.
Solution to the problem
According to an embodiment of the present specification, there is provided a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
x1 to X3 are identical to or different from each other and are each independently N or CH,
any one or more of X1 to X3 is N,
z is O or S, and the Z is O or S,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heteroaryl group,
ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
l is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
a is an integer of 0 to 5,
b is an integer of 0 to 4,
when a is plural, R1 are the same or different from each other,
when b is plural, R2 may be the same or different from each other.
In addition, the present specification provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or 2 or more layers of the organic layer contain the heterocyclic compound.
Effects of the invention
The heterocyclic compound according to an embodiment of the present specification may be used as a material of an organic layer of an organic light-emitting device, and by using the heterocyclic compound, an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics can be achieved in the organic light-emitting device.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron blocking layer
8: light-emitting layer
9: electron transport layer
10: electron injection layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a heterocyclic compound represented by the above chemical formula 1.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, examples of the substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents selected from the above exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be aryl substituted with aryl, aryl substituted with heteroaryl, heterocyclic group substituted with aryl, aryl substituted with alkyl, or the like.
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. More specifically, the number of carbon atoms is preferably 2 to 20. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the alkynyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. More specifically, the number of carbon atoms is preferably 2 to 20.
In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.
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 phenyl, biphenyl, terphenyl, 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 naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the present specification, the aryl group in the aryloxy group is the same as exemplified for the above aryl group.
In the present specification, the heteroaryl group contains 1 or more non-carbon atoms, i.e., hetero atoms, and specifically, the hetero atoms may contain 1 or more atoms selected from O, N, 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 heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the arylene group is as defined above for the aryl group, except that it is a valence 2.
In this specification, heteroaryl groups are as defined above for heteroaryl groups, except that they are 2-valent.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2 and 3.
[ chemical formula 2]
[ chemical formula 3]
In the above chemical formulas 2 and 3, the above X1 to X3, L, Y, ar1, ar2, R1, R2, a and b are as defined in the above chemical formula 1.
According to one embodiment of the present specification, X1 is N, and X2 and X3 are CH.
According to one embodiment of the present specification, X2 is N, and X1 and X3 are CH.
According to one embodiment of the present specification, X3 is N, and X1 and X2 are CH.
According to one embodiment of the present specification, X1 and X2 are N, and X3 is CH.
According to one embodiment of the present specification, X1 and X3 are N, and X2 is CH.
According to one embodiment of the present specification, X2 and X3 are N, and X2 is CH.
According to an embodiment of the present specification, X1 to X3 are N.
According to an embodiment of the present specification, R1 and R2 are hydrogen.
According to an embodiment of the present specification, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, containing any one or more of N, O and S.
According to one embodiment of the present specification, Y is aryl or heteroaryl,
the above aryl or heteroaryl group is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted phosphine oxide group.
According to one embodiment of the present specification, Y is an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms,
the above aryl group having 6 to 30 carbon atoms, or heteroaryl group having 3 to 30 carbon atoms is substituted or unsubstituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted phosphine oxide group.
According to one embodiment of the present specification, Y is phenyl, biphenyl, naphthyl, terphenyl, triphenylene, phenanthryl, fluoranthenyl, benzoOxazolyl, benzothiazolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, phosphino-oxide, pyridinyl, pyrimidinyl, triazinyl,
the phenyl, biphenyl, naphthyl, terphenyl, triphenylene, phenanthryl, fluoranthenyl, and benzoAn oxazolyl, benzothiazolyl, benzofuropyrimidinyl, benzothiophenopyrimidinyl, phosphino, pyridinyl, pyrimidinyl, triazinyl substituted or unsubstituted with deuterium, nitrile, halo, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted phosphino oxide.
According to an embodiment of the present specification, Y is a monocyclic aryl group having 6 to 30 carbon atoms, a polycyclic aryl group having 10 to 30 carbon atoms, a monocyclic heteroaryl group having 3 to 30 carbon atoms, or a polycyclic heteroaryl group having 3 to 30 carbon atoms,
the above monocyclic aryl group having 6 to 30 carbon atoms, polycyclic aryl group having 10 to 30 carbon atoms, monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms is substituted by deuterium; a nitrile group; a halogen group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with an aryl group; substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms containing any one or more of N, O or S; or substituted or unsubstituted phosphine oxide groups substituted or unsubstituted with alkyl or aryl groups.
According to an embodiment of the present specification, the above Y is phenyl substituted or unsubstituted with a nitrile group, a triphenylmethyl group, a naphthyl group, a phenylnaphthyl group, a triphenylsilyl group, or a trimethylsilyl group; a naphthyl group; a biphenyl group; phenanthryl; a terphenyl group; triphenylene; a fluoranthenyl group; benzo (E) benzo (EAn azole group; benzothiazolyl; benzofuropyrimidinyl substituted or unsubstituted with phenyl; benzothienopyrimidinyl substituted or unsubstituted with phenyl; a phosphine oxide group substituted with a phenyl group; pyridyl substituted or unsubstituted with phenyl; pyrimidinyl substituted or unsubstituted with phenyl; or triazinyl substituted or unsubstituted with phenyl.
According to an embodiment of the present specification, Y may be any one selected from the following substituents.
According to an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 are the same as each other and are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 mentioned above are the same as each other and are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 mentioned above are the same as each other and are a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 are each, independently, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, the above Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 described above are each independently a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted monocyclic heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 mentioned above are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzonaphthofuryl group, or a benzonaphthothienyl group,
the above phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorenyl group, spirobifluorenyl group, phenanthryl group, triphenylene group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, or benzonaphthothiophenyl group is substituted or unsubstituted by one or more substituents selected from deuterium, halogen group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms substituted or unsubstituted by alkyl group having 1 to 10 carbon atoms, or aryl group having 6 to 30 carbon atoms, and heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted by aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, ar1 and Ar2 mentioned above are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzonaphthofuryl group, or a benzonaphthothienyl group,
the phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorenyl group, spirobifluorenyl group, phenanthryl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group, dibenzothienyl group, benzonaphthofuranyl group, or benzonaphthothienyl group may be substituted with one or more substituents selected from deuterium, phenyl group, naphthyl group, and methyl group.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a carbazolyl group substituted or unsubstituted with a phenyl group, a dibenzofuranyl group, or a dibenzothienyl group.
According to an embodiment of the present specification, ar1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, carbazolyl substituted or unsubstituted with phenyl, dibenzofuranyl, or dibenzothiophenyl.
According to an embodiment of the present specification, ar2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, carbazolyl substituted or unsubstituted with phenyl, dibenzofuranyl, or dibenzothiophenyl.
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 directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, L is a monocyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted.
According to an embodiment of the present specification, L is a directly bonded or substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms.
According to an embodiment of the present specification, the above L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenyl group having a valence of 2, a substituted or unsubstituted terphenyl group having a valence of 2, a substituted or unsubstituted tetrabiphenyl group having a valence of 2, a substituted or unsubstituted fluorenyl group having a valence of 2, a substituted or unsubstituted anthryl group having a valence of 2, a substituted or unsubstituted pyrenyl group having a valence of 2, a substituted or unsubstituted triphenylene group having a valence of 2, or a substituted or unsubstituted phenanthryl group having a valence of 2.
According to an embodiment of the present specification, the above L is a phenylene group substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a naphthylene group substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a biphenyl group substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a terphenyl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a tetraphenyl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a fluorenyl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, an anthryl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a pyrenyl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, a triphenylenyl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms, or a phenanthryl group having 2 valences substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, L is a phenylene group, a naphthylene group, a 2-valent biphenyl group, a 2-valent terphenyl group, a 2-valent tetrabiphenyl group, a 2-valent fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a 2-valent anthryl group, a 2-valent pyrenyl group, a 2-valent triphenylenyl group, or a 2-valent phenanthryl group.
According to an embodiment of the present specification, the above L may be represented by the following substituent.
According to an embodiment of the present disclosure, L is a direct bond.
According to an embodiment of the present specification, L is phenylene.
According to one embodiment of the present specification, L is a 2-valent naphthyl group.
According to another embodiment of the present specification, the heterocyclic compound of the above chemical formula 1 may be represented by the following structural formula.
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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 includes a first electrode, a second electrode provided opposite to the first electrode, and an organic layer having 1 or 2 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer may contain the heterocyclic compound.
For example, the structure of the organic light emitting device of the present invention may have the structure shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
Fig. 2 illustrates a junction structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, an electron transport layer 9, an electron injection layer 10, and a second electrode 4 are sequentially stacked on a substrate 1. In particular, the compound of the present invention may be contained in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, preferably, a light emitting layer.
Fig. 1 and 2 are diagrams illustrating an organic light emitting device, and are not limited thereto.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.
The organic light emitting device of the present invention includes a light emitting layer including a host and a dopant in a mass ratio of 90:10 to 50:50.
The organic light emitting device of the present invention includes a light emitting layer including a host and a dopant in a mass ratio of 90:10 to 60:40.
The organic light emitting device of the present invention includes a light emitting layer including a host and a dopant in a mass ratio of 90:10 to 80:20.
In one embodiment of the present invention, the organic layer includes a light-emitting layer including the heterocyclic compound as a main body.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include an additional host.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include an organic compound as an additional host.
In one embodiment of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include a carbazole derivative as an additional host.
In one embodiment of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include a dicarbazole compound as an additional host.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include a compound of the following chemical formula X as an additional host.
[ chemical formula X ]
In the above-mentioned chemical formula X, the amino acid,
ax and Ay are the same or different from each other and are each independently a substituted or unsubstituted aryl group,
rx and Ry are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heteroaryl group,
x and y are each integers from 0 to 7,
when x and y are each plural, the substituents in brackets are the same or different from each other.
In one embodiment of the present invention, ax and Ay are the same or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present invention, ax and Ay are the same or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, an anthryl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, or a pyrenyl group.
In one embodiment of the present invention, ax and Ay are the same as or different from each other, and each is independently a phenyl group or a biphenyl group.
In one embodiment of the invention, rx and Ry are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.
In one embodiment of the invention, rx and Ry are hydrogen.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include an additional dopant.
In an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include a fluorescent dopant.
In an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include a phosphorescent dopant.
In an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include a metal complex as a dopant.
In an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include an iridium dopant.
In an embodiment of the present invention, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the heterocyclic compound.
In an embodiment of the present invention, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the heterocyclic compound.
In an embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
The method of manufacturing the heterocyclic compound of chemical formula 1 and the manufacture of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following production methods, all the compounds described in the present specification can be produced by changing the types and substitution positions of substituents.
Production example
Production example 1: production of Compounds 1A to 1G
1) Production of Compound 1A
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (50.0 g,187 mmol) and (2-chloro-3-fluorophenyl) boric acid (48.9 g,280 mmol) were added to 400ml tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (77.6 g, 560 mmol) was dissolved in 210ml of water and added thereto, and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (6.5 g,3 mol%) was added thereto. After reacting for 12 hours, the temperature was lowered to normal temperature, and after separating the organic layer and the aqueous layer, the organic layer was distilled under reduced pressure. After the distillate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, after drying the organic layer, it was recrystallized from ethyl acetate, whereby compound 1A (52.1 g, 77%) was produced.
MS:[M+H]+＝362
2) Production of Compound 1B
Compound 1A (52.1 g,144 mmol) and (3-chloro-2-hydroxyphenyl) boronic acid (37.6 g,216 mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (77.6 g, 560 mmol) was dissolved in 210ml of water and added thereto, and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (6.5 g,3 mol%) was added thereto. After reacting for 12 hours, the temperature was lowered to normal temperature, and after separating the organic layer and the aqueous layer, the organic layer was distilled under reduced pressure. After the distillate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, after drying the organic layer, compound 1B (32.0 g, 49%) was produced by column chromatography of hexane and ethyl acetate.
MS:[M+H]+＝454
3) Production of Compound 1C
Compound 1B (32.0 g,144 mmol) was dissolved in 300ml of chloroform under nitrogen atmosphere, and after stirring well at 0℃N-bromosuccinimide (11.8 g,71 mmol) was slowly added dropwise in portions. After slowly heating to room temperature, the reaction was carried out for 1 hour, and then water was added to terminate the reaction. Then, after extraction with water and sodium thiosulfate solution 2 times, respectively, the organic layer was distilled under reduced pressure. After the distillate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, after drying the organic layer, it was recrystallized from ethyl acetate, whereby compound 1C (31.9 g, 85%) was produced.
MS:[M+H]+＝532
4) Production of Compound 1D
Compound 1C (31.9 g,60 mmol) was added to 200ml of dimethylformamide under nitrogen and stirred. Then, potassium carbonate (16.6 g,120 mmol) was added thereto and the mixture was refluxed. After 2 hours, the temperature was lowered to room temperature and filtered. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, followed by recrystallization from ethyl acetate. The resultant solid was filtered and dried to produce compound 1D (21.8 g, 71%).
MS:[M+H]+＝512
5) Production of Compound 1E
Intermediate 1D (21.8 g,43 mmol), bis (pinacolato) diboron (11.9 g,47 mmol) and potassium acetate (17.7 g,128 mmol) were mixed under nitrogen and added to 300ml of diThe alkane was heated with stirring. Bis (dibenzylideneacetone) palladium (0.7 g,1.3 mmol) and tricyclohexylphosphine (0.7 g,2.6 mmol) were added under reflux, and heated and stirred for 3 hours. After the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured with water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed, whereby compound 1E (21.4 g, 80%) was produced.
MS:[M+H]+＝602
6) Production of Compound 1F
Compound 1E (21.4 g,38 mmol) and 2-chlorobenzo [ d ] thiazole (7.2 g,42 mmol) were added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (15.9 g,115 mmol) was dissolved in 50ml of water and charged, and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (1.3 g,3 mol%) was charged. After 4 hours of reaction, the temperature was lowered to room temperature, and after separating the organic layer and the aqueous layer, the organic layer was distilled under reduced pressure. After the distillate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was dried, and then recrystallized from ethyl acetate, whereby compound 1F (15.1 g, 70%) was produced.
MS:[M+H]+＝567
7) Production of Compound 1G
Intermediate 1F (15.1 g,27 mmol), bis (pinacolato) diboron (7.5 g,29 mmol) and potassium acetate (11.1 g,80 mmol) were mixed under nitrogen and added to 200ml of diThe alkane was heated with stirring. Bis (dibenzylideneacetone) palladium (0.5 g,0.8 mmol) and tricyclohexylphosphine (0.5 g,1.6 mmol) were added under reflux, and heated and stirred for 6 hours. After the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured with water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed, whereby compound 1G (16.0G, 91%) was produced.
MS:[M+H]+＝659
Production example 2: production of Compounds 1 to 9
1) Production of Compound 1
Compound 1G (15.0G, 23 mmol) and 2-bromobenzene (3.9G, 25 mmol) were added to 200ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (9.4 g,68 mmol) was dissolved in 20ml of water and added thereto, and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (0.8 g,3 mol%) was added thereto. After reacting for 12 hours, the temperature was lowered to normal temperature, and after separating the organic layer and the aqueous layer, the organic layer was distilled under reduced pressure. After the distillate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, after drying the organic layer, it was recrystallized from ethyl acetate, whereby compound 1 (8.7 g, 63%) was produced.
MS:[M+H]+＝608
2) Production of Compound 2
Compound 2 (10.6 g, 71%) was synthesized by the same method as the production of the above-mentioned compound 1 except that 1-bromonaphthalene was used instead of 2-bromobenzene.
MS:[M+H]+＝659
3) Production of Compound 3
Compound 3 (8.6 g, 55%) was synthesized by the same method as the production of the above-mentioned compound 1 except that 4-bromobiphenyl was used instead of 2-bromobenzene.
MS:[M+H]+＝685
4) Production of Compound 4
/>
Compound 4 (4.7 g, 30%) was synthesized by the same method as the production of the above-mentioned compound 1 except that 3-bromobiphenyl was used instead of 2-bromobenzene.
MS:[M+H]+＝685
5) Production of Compound 5
Compound 5 (10.2 g, 63%) was synthesized by the same method as the production of the above-mentioned compound 1 except that 9-bromophenanthrene was used instead of 2-bromobenzene.
MS:[M+H]+＝709
6) Production of Compound 6
Compound 6 (10.3 g, 59%) was synthesized by the same method as the production of the above-described compound 1 except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was used instead of 2-bromobenzene.
MS:[M+H]+＝765
7) Production of Compound 7
Compound 7 (12.3 g, 81%) was synthesized by the same method as the preparation of the above-mentioned compound 1 except that 2-chlorobenzo [ d ] thiazole was used instead of 2-bromobenzene.
MS:[M+H]+＝666
8) Production of Compound 8
Compound 8 (6.3 g, 44%) was synthesized by the same method as the production of the above-mentioned compound 1 except that 3-bromobenzonitrile was used instead of 2-bromobenzene.
MS:[M+H]+＝634
9) Production of Compound 9
Compound 9 (15.1 g, 84%) was synthesized by the same method as the preparation of the above-mentioned compound 1 except that 2-chloro-4-phenylbenzothiophene [3,2-d ] pyrimidine was used instead of 2-bromobenzene.
MS:[M+H]+＝793
Experimental example
Experimental example 1]
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-1 compound was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HT-1 compound was used as a catalyst>A hole transport layer is formed by thermal vacuum vapor deposition, and the HT-2 compound is added to the HT-1 vapor deposited film>And vacuum evaporation is performed to form an electron blocking layer. On the HT-2 vapor deposited film, the above-produced compound 1, YGH-1 compound described below, and phosphorescent dopant YGD-1 were vacuum deposited as light-emitting layers in a weight ratio of 44:44:12 to form +.>A light emitting layer of thickness. On the above luminescent layer, the following ET-1 compound was used as +.>An electron transport layer was formed by vacuum vapor deposition, and an ET-2 compound and Li described below were vacuum vapor deposited at a weight ratio of 98:2 on the electron transport layer to form +.>An electron injection layer of thickness. On the electron injection layer, by +.>Aluminum is deposited to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedAluminum maintenance->Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 ～5×10 -8 And (5) a bracket.
< Experimental examples 2 to 9>
An organic light-emitting device was manufactured in the same manner as in experimental example 1 above, except that the compound described in table 1 below was used instead of the compound 1 in experimental example 1 above.
Comparative Experimental examples 1 to 3]
An organic light-emitting device was manufactured in the same manner as in experimental example 1 above, except that the compound described in table 1 below was used instead of the compound 1 in experimental example 1 above. The compounds of CE1 to CE3 of table 1 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting device was used at 10mA/cm 2 Voltage and efficiency were measured at a current density of 50mA/cm 2 The lifetime was measured at the current density of (2), and the results are shown in table 1 below. In this case, LT95 means a time required for the initial luminance to be 95%.
TABLE 1
The compounds of the invention exhibit lower voltage, high efficiency and long life characteristics compared to CE1 not comprising a dibenzofuran nucleus,
when the N-containing monocyclic ring was bonded to the 2-position of dibenzofuran like CE2, the compound showed low efficiency and significantly shorter lifetime than those of examples 1 to 9 using the compound of the present invention, and when there was no substituent at the 6-position like CE3, the compound showed short lifetime as compared with examples 1 to 9.
When the compound of the present invention was used as a light-emitting layer material, it was confirmed that the compound exhibited excellent efficiency and lifetime characteristics as compared with comparative experimental examples. The reason for this is that the electron stability is increased by replacing hydrogen with aryl and heteroaryl in position 6 and benzothiazole in position 8 of the dibenzofuran substituent.
Claims (8)
1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
x1 to X3 are each independently N,
z is O or S, and the Z is O or S,
r1 and R2 are each independently hydrogen,
ar1 and Ar2 are the same or different from each other and each independently is an aryl group having 6 to 30 carbon atoms, a carbazolyl group substituted or unsubstituted by a phenyl group, a dibenzofuranyl group, or a dibenzothienyl group,
l is a direct bond, or an arylene group having 6 to 30 carbon atoms,
y is phenyl, biphenyl, naphthyl, terphenyl, triphenylene, phenanthryl, fluoranthenyl, benzoOxazolyl, benzothiazolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, or triazinyl, said phenyl, biphenyl, naphthyl, terphenyl, triphenylene, phenanthryl, fluoranthenyl, benzo->An oxazolyl, benzothiazolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, or triazinyl group substituted or unsubstituted with a nitrile, phenyl, or biphenyl group,
a is an integer of 0 to 5,
b is an integer from 0 to 4.
2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2 and 3:
chemical formula 2
Chemical formula 3
In the chemical formulas 2 and 3, the X1 to X3, L, Y, ar1, ar2, R1 and R2 are the same as defined in the chemical formula 1,
a and b are each 0.
3. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are the same or different from each other, and each is independently a monocyclic aryl group having 6 to 30 carbon atoms or a polycyclic aryl group having 6 to 30 carbon atoms.
4. The heterocyclic compound according to claim 1, wherein L is a direct bond, or a phenylene group.
5. The heterocyclic compound according to claim 1, wherein Y is phenyl, biphenyl, naphthyl, terphenyl, triphenylene, phenanthryl, or fluoranthenyl.
6. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is any one selected from the following compounds:
7. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the heterocyclic compound according to any one of claims 1 to 6.
8. The organic light-emitting device of claim 7, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound.
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| KR101385216B1 (en) * | 2012-11-07 | 2014-04-14 | 주식회사 엘엠에스 | Novel compound, light-emitting device including the compound and electronic device |
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| WO2016198144A1 (en) * | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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