CN113444098B - Novel heterocyclic compound and organic light-emitting element comprising same - Google Patents
Novel heterocyclic compound and organic light-emitting element comprising same Download PDFInfo
- Publication number
- CN113444098B CN113444098B CN202010218466.4A CN202010218466A CN113444098B CN 113444098 B CN113444098 B CN 113444098B CN 202010218466 A CN202010218466 A CN 202010218466A CN 113444098 B CN113444098 B CN 113444098B
- Authority
- CN
- China
- Prior art keywords
- compound
- group
- emitting element
- aryl
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 41
- 239000010410 layer Substances 0.000 claims description 55
- 239000000126 substance Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- -1 polycyclic compound Chemical class 0.000 abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 239000011368 organic material Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 description 90
- 239000000463 material Substances 0.000 description 63
- 238000004519 manufacturing process Methods 0.000 description 35
- 125000003118 aryl group Chemical group 0.000 description 33
- 125000001072 heteroaryl group Chemical group 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 21
- 229910052741 iridium Inorganic materials 0.000 description 17
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 16
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 11
- 150000002431 hydrogen Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 125000005549 heteroarylene group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[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.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 238000006069 Suzuki reaction reaction Methods 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 8
- 235000019345 sodium thiosulphate Nutrition 0.000 description 8
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920000767 polyaniline Polymers 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 6
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 description 6
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical group C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 229910052805 deuterium Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 229910052711 selenium Inorganic materials 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 4
- 239000000391 magnesium silicate Substances 0.000 description 4
- 229910052919 magnesium silicate Inorganic materials 0.000 description 4
- 235000019792 magnesium silicate Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 3
- 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 3
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 3
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 3
- SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 description 2
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 description 2
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 description 2
- DBDCPKPHHCECLZ-UHFFFAOYSA-N 1-chloro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Cl)=CC=C2 DBDCPKPHHCECLZ-UHFFFAOYSA-N 0.000 description 2
- HUOUJYMIUQWENN-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetrakis(4-methylphenyl)-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound C1=CC(C)=CC=C1N(C1(C=CC(=CC1)C=1C=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 HUOUJYMIUQWENN-UHFFFAOYSA-N 0.000 description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 2
- QWNCDHYYJATYOG-UHFFFAOYSA-N 2-phenylquinoxaline Chemical compound C1=CC=CC=C1C1=CN=C(C=CC=C2)C2=N1 QWNCDHYYJATYOG-UHFFFAOYSA-N 0.000 description 2
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003943 azolyl group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- WTEWXIOJLNVYBZ-UHFFFAOYSA-N n-[4-[4-(4-ethenyl-n-naphthalen-1-ylanilino)phenyl]phenyl]-n-(4-ethenylphenyl)naphthalen-1-amine Chemical compound C1=CC(C=C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC(C=C)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 WTEWXIOJLNVYBZ-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 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 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- TXBFHHYSJNVGBX-UHFFFAOYSA-N (4-diphenylphosphorylphenyl)-triphenylsilane Chemical compound C=1C=CC=CC=1P(C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 TXBFHHYSJNVGBX-UHFFFAOYSA-N 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- CKEGHWVVAIEDPU-UHFFFAOYSA-N 1-chloro-2-iodo-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C(I)=C1 CKEGHWVVAIEDPU-UHFFFAOYSA-N 0.000 description 1
- MPEOPBCQHNWNFB-UHFFFAOYSA-N 1-chloro-2-iodobenzene Chemical compound ClC1=CC=CC=C1I MPEOPBCQHNWNFB-UHFFFAOYSA-N 0.000 description 1
- ZWZXDJMNYGRYNP-UHFFFAOYSA-N 1-n,4-n-bis(3-methylphenyl)-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 ZWZXDJMNYGRYNP-UHFFFAOYSA-N 0.000 description 1
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000007303 Carboni reaction Methods 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 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
- 239000005909 Kieselgur Substances 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
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JJNATTOAHGMEHT-UHFFFAOYSA-M copper(1+);iodate Chemical compound [Cu+].[O-]I(=O)=O JJNATTOAHGMEHT-UHFFFAOYSA-M 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-N 0.000 description 1
- CBSFHSKFQDSSQB-UHFFFAOYSA-N n-[4-[3,5-bis[4-(3-methylanilino)phenyl]phenyl]phenyl]-3-methylaniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=C(C=C(C=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)=C1 CBSFHSKFQDSSQB-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 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
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
-
- 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
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same, and the heterocyclic compound according to the present invention is a polycyclic compound containing a nitrogen atom and can be used as an organic material for an organic light-emitting element.
Description
Technical Field
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same.
Background
The organic electroluminescent element is one of self-luminous display elements, and has advantages of wide viewing angle, excellent contrast, and fast response speed.
The organic light emitting element has a structure in which an organic thin film is arranged between 2 electrodes. When a voltage is applied to the light-emitting element having such a structure, electrons and holes injected from 2 electrodes are combined in the organic thin film, and quenched and emitted in pairs. The organic thin film may be formed of a single layer or a plurality of layers as required.
The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound which itself can constitute a light-emitting layer alone, or a compound which can function as a host or a dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material of the organic thin film, a compound that can function as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like can be used.
In order to improve the performance, lifetime, or efficiency of an organic light emitting element, development of an organic thin film material is required.
Prior art literature
Patent literature
(patent document 1) U.S. Pat. No. 4,356,429
Disclosure of Invention
The object of the present invention is to provide a heterocyclic compound of a novel structure which can be used as an organic material for an organic light-emitting element.
In addition, the present invention aims to provide an organic light-emitting element comprising the above heterocyclic compound as an organic layer material.
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same, and the heterocyclic compound according to the present invention is a polycyclic compound containing nitrogen atoms and can be used as an organic material layer of the organic light-emitting element.
The present invention provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
R 1 to R 15 At least one of them is-L-Ar, the remainder are each independently hydrogen, deuterium, cyano, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, -SiR a R b R c 、-P(＝O)R a R b or-NR a R b ；
R a 、R b And R is c Each independently is hydrogen, deuterium, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl or C2-C60 heteroaryl;
l is a single bond, C6-C60 arylene or C2-C60 heteroarylene;
ar is C6-C60 aryl or C2-C60 heteroaryl;
r is as described above 1 To R 15 Alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl, arylene and heteroarylene of L, aryl and heteroaryl of ArHeteroaryl groups may be selected from C1-C60 alkyl, halo, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C2-C60 heteroaryl, -SiR d R e R f 、-NR g R h More than one of nitro and hydroxy is further substituted;
R d 、R e and R is f Each independently is C1-C60 alkyl or C6-C60 aryl;
R g and R is h Each independently is hydrogen, C1-C60 alkyl or C6-C60 aryl;
the heteroarylene, heteroaryl and heterocycloalkyl groups described above contain one or more heteroatoms selected from N, O, S and Se.
In addition, the present invention provides an organic light emitting element, comprising: an anode, a cathode, and an organic layer having 1 or more layers between the anode and the cathode, wherein 1 or more layers of the organic layer contain the heterocyclic compound of chemical formula 1.
The heterocyclic compound according to the present invention is a novel nitrogen atom-containing polycyclic compound composed of a 1-phenyl-benzimidazole skeleton and a carbazole skeleton, wherein the No. 9 nitrogen of the carbazole skeleton is bonded to the No. 2 carbon of the 1-phenyl-benzimidazole skeleton, and the No. 1 carbon of the carbazole skeleton is bonded to the carbon ortho to the phenyl group substituted at the No. 1 position of the 1-phenyl-benzimidazole skeleton, and can be used as an organic material layer of an organic light-emitting element. The heterocyclic compound can play a role of a light-emitting material, a hole-injecting material, a hole-transporting material, a light-emitting material, an electron-transporting material, an electron-injecting material, and the like in an organic light-emitting element.
In the case where the heterocyclic compound according to the present invention is contained in a light-emitting layer of an organic light-emitting element as a host material, in particular, as a phosphorescent host material, light-emitting efficiency, electric power efficiency
Excellent quantum efficiency and element lifetime, and can display proper color coordinates.
The heterocyclic compound according to the present invention has excellent electron mobility, improves the current characteristics of the element, strengthens the driving voltage, and thus induces an increase in the power utilization coefficient, thereby enabling the manufacture of an organic light-emitting element having improved power consumption, and can prevent the phenomenon of red shift at PL wavelength due to spatial bit blocking on the structure, thereby enabling realization of suitable color reproducibility.
Detailed Description
The present invention will be described in detail below, and technical and scientific terms used herein have the meaning commonly understood by one of ordinary skill in the art to which the invention belongs unless otherwise defined, and descriptions of well-known functions and configurations that may unnecessarily obscure the gist of the present invention will be omitted from the following description.
In the present specification, the "alkyl", "alkoxy" and other substituents containing an "alkyl" moiety are all included in a straight-chain or branched form.
In the present specification, the alkyl group contains a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.
In the present specification, an alkenyl group contains a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkenyl group may have a carbon number of 2 to 60, specifically 2 to 40, more specifically 2 to 20.
In the present specification, an alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically may be 2 to 40, and more specifically may be 2 to 20.
In the present specification, cycloalkyl groups include a single ring or multiple rings having 3 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic refers to a group in which the cycloalkyl group is directly linked or fused to another cyclic group. The other cyclic group may be a cycloalkyl group, or may be other kinds of cyclic groups, such as a heterocycloalkyl group, an aryl group, a heterocycle, or the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
In this specification, the heterocycloalkyl group contains at least one selected from N, O, S and Se as a hetero atom, and contains a single ring or multiple rings of 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with other cyclic groups. The other cyclic group may be a heterocycloalkyl group, or may be another cyclic group such as a cycloalkyl group, an aryl group, a heterocycle, or the like. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.
In the present specification, an aryl group is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and includes a single ring or multiple rings of 6 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic refers to a group in which the aryl group is directly linked or fused to other cyclic groups. The other cyclic group may be an aryl group, or may be other kinds of cyclic groups such as cycloalkyl, heterocycloalkyl, heterocycle, and the like. The number of carbon atoms of the aryl group may be 6 to 60, specifically may be 6 to 40, and more specifically may be 6 to 25. Specific examples of the aryl group include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, and the like,
A group, phenanthryl group, perylene group, fluoranthenyl group, triphenylene group, phenanyl group, pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, fluorenyl group, etc. or condensed rings thereof, but is not limited thereto.
In the present specification, "arylene" means a 2-valent organic radical derived by removing one hydrogen in the above aryl group, following the definition of the above aryl group.
In this specification, the heterocyclic group contains at least one selected from N, O, S and Se as a hetero atom, and contains a single ring or multiple rings of 2 to 60 carbon atoms, and may be further substituted with other substituents. Heteroaryl groups are included within the scope of heterocyclyl groups and are heteroaromatic ring groups. Here, polycyclic means heteroAnd a group in which the cyclic group is directly connected or condensed with other cyclic groups. The other cyclic group may be a heterocyclic group, or may be other kinds of cyclic groups, such as cycloalkyl, heterocycloalkyl, aryl, and the like. The number of carbon atoms of the heterocyclic group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, and the like,
Azolyl, iso->
Oxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl,/-yl>
Diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl,/i>
Oxazinyl, thiazinyl, di +.>
Alkenyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthyridinyl, triazaindene, indolyl, indolizinyl, benzothiazolyl, benzo->
An oxazolyl group, a benzimidazolyl group, a benzothienyl group, a benzofuranyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzocarbazolyl group, a phenazinyl group, or the like, or a condensed ring thereof, but is not limited thereto.
In the present specification, "heteroaryl" means an aryl group containing at least one hetero atom selected from N, O, S and Se as an aromatic ring skeleton atom, and the remaining aromatic ring skeleton atoms are carbonIs a 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl fused to more than one benzene ring, which may be partially saturated. In addition, heteroaryl groups in the present invention also include more than one heteroaryl group in a singly-linked form. As specific examples, it contains furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, and isozyl
Azolyl, (-) -and (II) radicals>
Monocyclic heteroaryl groups such as oxazolyl, triazinyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, and benzisothiazolyl>
Azolyl, benzo->
Polycyclic heteroaryl groups such as an oxazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, and a benzocarbazolyl group, but the present invention is not limited thereto.
In the present specification, "heteroarylene" means a 2-valent organic radical derived by removing one hydrogen in the above heteroaryl group, following the definition of the above heteroaryl group.
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same, and more particularly, to a novel nitrogen atom-containing polycyclic compound having a novel structure in which a 1-phenyl-benzimidazole skeleton and a carbazole skeleton are combined, and a No. 9 nitrogen of the carbazole skeleton is bonded to a No. 2 carbon of the 1-phenyl-benzimidazole skeleton, and a No. 1 carbon of the carbazole skeleton is bonded to a carbon ortho to a phenyl group substituted at a No. 1 position of the 1-phenyl-benzimidazole skeleton, and an organic light-emitting device including the same.
The heterocyclic compound according to the present invention may be represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
R 1 to R 15 At least one of them is-L-Ar, the remainder are each independently hydrogen, deuterium, cyano, C1-C60 alkyl, C2-C60 alkenyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C2-C60 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, -SiR a R b R c 、-P(＝O)R a R b or-NR a R b ；
R a 、R b And R is c Each independently is hydrogen, deuterium, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl or C2-C60 heteroaryl;
l is a single bond, C6-C60 arylene or C2-C60 heteroarylene;
ar is C6-C60 aryl or C2-C60 heteroaryl;
r is as described above 1 To R 15 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl groups, arylene and heteroarylene groups of L, aryl and heteroaryl groups of Ar may be selected from C1-C60 alkyl, halo C1-C60 alkyl, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C2-C60 heteroaryl, -SiR d R e R f 、-NR g R h More than one of nitro and hydroxy is further substituted;
R d 、R e and R is f Each independently is C1-C60 alkyl or C6-C60 aryl;
R g and R is h Each independently is hydrogen, C1-C60 alkyl or C6-C60 aryl;
the heteroarylene, heteroaryl and heterocycloalkyl groups described above contain one or more heteroatoms selected from N, O, S and Se.
Specifically, the heterocyclic compound of the above chemical formula 1 is thermally stable due to the introduction of a specific substituent and a core structure having a morphology in which three nitrogen atoms are bonded with a carbon atom as a center, and can exhibit maximized electron mobility.
The heterocyclic compound of chemical formula 1 has an advantage that it can exhibit phosphorescence characteristics based on the structural characteristics, and can be used as an organic material layer material for an organic light-emitting element, and particularly when used as a light-emitting layer material, it can enhance the driving voltage by increasing the electron mobility and induce an increase in the power utilization coefficient, thereby producing an organic light-emitting element with improved power consumption. In addition, the heterocyclic compound of the above chemical formula 1 can prevent the red shift phenomenon at PL wavelength caused by steric hindrance in the structure, and thus can achieve suitable color reproducibility.
In one embodiment, the heterocyclic compound may be represented by the following chemical formula 2:
[ chemical formula 2]
In the above-mentioned chemical formula 2,
R 11 is-L 1 -Ar 1 ；R 12 is-L 2 -Ar 2 ；R 13 is-L 3 -Ar 3 ；R 14 is-L 4 -Ar 4 ；
L 1 、L 2 、L 3 And L 4 Each independently is a single bond, a C6-C60 arylene group, or a C2-C60 heteroarylene group;
Ar 1 、Ar 2 、Ar 3 and Ar is a group 4 Each independently is a C6-C60 aryl or C2-C60 heteroaryl group;
R 21 to R 24 Each independently is hydrogen, deuterium, a C6-C60 aryl or a C2-C60 heteroaryl;
a to d are each independently integers of 0 or 1, and satisfy 2.ltoreq.a+b+c+d.ltoreq.4;
r is as described above 21 To R 24 Aryl or heteroaryl, L 1 To L 4 Arylene and heteroarylene of (2), ar 1 To Ar 4 The aryl and heteroaryl groups of (a) may be further substituted with one or more selected from the group consisting of C1-C60 alkyl, C6-C60 aryl, C1-C60 alkyl, C6-C60 aryl and C2-C60 heteroaryl.
In the heterocyclic compound, the a+b+c+d may be 2 in terms of achieving excellent light-emitting efficiency and improved driving life.
As an example, a is 1, b is 0, c is 0, and d may be 1.
As an example, a is 1, b is 0, c is 1, and d may be 0.
As an example, a is 0, b is 1, c is 1, and d may be 0.
As an example, a is 0, b is 1, c is 0, and d may be 1.
In one embodiment, the heterocyclic compound may be represented by any one of the following chemical formulas 3 to 6:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
In the above-mentioned chemical formulas 3 to 6,
L 1 、L 2 、L 3 and L 4 Each independently is a single bond, a C6-C30 arylene group, or a C2-C30 heteroarylene group;
Ar 1 、Ar 2 、Ar 3 and Ar is a group 4 Each independently is a C6-C30 aryl or C2-C30 heteroaryl group;
R 21 to R 24 Each independently is hydrogen, deuterium, a C6-C30 aryl or a C2-C30 heteroaryl;
r is as described above 21 To R 24 Aryl or heteroaryl, L 1 To L 4 Arylene and heteroarylene of (2), ar 1 To Ar 4 The aryl and heteroaryl groups of (a) may be further substituted with one or more selected from the group consisting of C1-C30 alkyl, C6-C30 aryl, C1-C30 alkyl, C6-C30 aryl and C2-C30 heteroaryl.
In one embodiment, L is as described above 1 、L 2 、L 3 And L 4 Each independently is a single bond or a C6-C30 arylene group, L 1 To L 4 May be further substituted with one or more selected from the group consisting of C1-C30 alkyl, C6-C30 aryl, C1-C30 alkyl-C6-C30 aryl, and C2-C30 heteroaryl; ar (Ar) 1 、Ar 2 、Ar 3 And Ar is a group 4 Each independently may be selected from the following structures, but is not limited thereto:
in the above-mentioned,
X 1 is NR (NR) 31 O or S;
Y 1 is CR (CR) 32 R 33 O or S;
R 31 is a C6-C30 aryl or C2-C30 heteroaryl group;
R 32 and R is 33 Each independently is a C1-C30 alkyl, C6-C30 aryl, or C2-C30 heteroaryl group;
r ', R ' and R ' are each independently of the other hydrogen, C6-C30 aryl or C2-C30 heteroaryl;
the aryl groups of R ', R ' and R ' described above may be further substituted with C1-C30 alkyl groups.
In one embodiment, L is as described above 1 、L 2 、L 3 And L 4 Each independently isSingle bond or C6-C20 arylene group, above L 1 To L 4 The arylene group of (a) may be further substituted with one or more selected from the group consisting of C6-C20 aryl, C1-C20 alkyl C6-C20 aryl, and C2-C20 heteroaryl.
In one embodiment, L is as described above 1 、L 2 、L 3 And L 4 Each independently may be a single bond or selected from the following structures, but is not limited thereto:
in the above-mentioned,
R L1 、R L2 and R is L3 Each independently is hydrogen, C6-C30 aryl, C1-C30 alkyl C6-C30 aryl, and C2-C30 heteroaryl.
In one embodiment, the heterocyclic compound may be selected from the following structures, but is not limited thereto.
The heterocyclic compound according to an embodiment of the present invention may be used in an organic layer of an organic light-emitting element based on its structural specificity, and specifically, may be used as a host compound in a light-emitting layer in the above organic layer. More specifically, the heterocyclic compound according to an embodiment of the present invention may be used as a phosphorescent host compound in the light-emitting layer in the organic layer described above.
The above-mentioned compound can be produced based on the production examples described below. In the production examples described below, representative examples are described, but substituents may be added or removed as necessary, and the positions of the substituents may be changed. The starting materials, the reaction conditions, and the like may be changed based on techniques in this technical field. Regarding the kind or position of the substituents at the remaining positions, which are changed as needed, those skilled in the art can implement them by using techniques known in the art.
In addition, the present invention provides an organic light-emitting element comprising the heterocyclic compound of the above chemical formula 1.
Specifically, the organic light emitting element according to the present invention includes: an anode, a cathode, and an organic layer having 1 or more layers between the anode and the cathode, wherein 1 or more layers of the organic layer contain the heterocyclic compound of chemical formula 1.
However, the structure of an organic light emitting element known in the art can also be applied to the present invention. The scope of the present invention is not limited to such a laminated structure, and other layers other than the light-emitting layer may be omitted or other functional layers may be further added as needed.
The organic light emitting element according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers contains the heterocyclic compound of chemical formula 1 described above.
The heterocyclic compound of chemical formula 1 may constitute 1 or more layers among the organic layers of the organic light-emitting element alone. However, the organic layer may be formed by mixing other substances as needed.
The heterocyclic compound of chemical formula 1 can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, or the like in an organic light emitting element. The heterocyclic compound of chemical formula 1 can be used as a material for at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. As an example, the heterocyclic compound of the above chemical formula 1 may be used as an electron injection and transport layer material of an organic light emitting element. As another example, the heterocyclic compound of the above chemical formula 1 may be used as a light-emitting layer material of an organic light-emitting element. As another example, the heterocyclic compound of the above chemical formula 1 may be used as a host material of a phosphorescent light-emitting layer of an organic light-emitting element.
In the organic light-emitting element according to the present invention, materials other than the heterocyclic compound of the above chemical formula 1 are exemplified below, but these are only examples, and the scope of the present invention is not limited thereto, and materials known in the art may be substituted for them.
As the anode material, a material having a relatively large work function can be used, and as a specific example, metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof can be used; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), polypyrrole and polyaniline, etc., but not limited thereto. In addition, the anode layer may be formed of only one type of the above materials, or may be formed of a mixture of a plurality of materials, and a multilayer structure composed of a plurality of layers of the same composition or different compositions may be formed.
As the cathode material, a material having a relatively small work function can be used, and as a specific example, magnesium, calcium, sodium, potassium, titanium, indium, and the like can be used,Metals such as yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO 2 Multilayer structure such as Al.
As the hole injecting material, a known hole injecting material can be used, and for example, phthalocyanine compounds such as CuPc (copper phthalocyanine ) disclosed in U.S. Pat. No. 4,356,429, or star burst type amine derivatives described in document [ Advanced Material,6, p.677 (1994) ] such as TCTA (tris (4-carbazolyl-9-ylphenyl) amine, tris (4-carbazolyl-9-ylphenyl) amine), m-MTDATA (4, 4',4″ -tris (3-Methylphenylphenylamino) triphenylamine, 4',4″ -tris (3-methylphenyl amino) triphenylamine), m-mtmtb (1, 3,5-tris [4- (3-methylphenyl amino) phenyl ] benzenzenzenzene, 1,3,5-tris [4- (3-methylphenyl amino) phenyl ] benzene), and high-solubility as a polymer such as Polyaniline/Polyaniline, or polyether sulfonic acid (3, dapsa); PSS (Poly (3, 4-ethylenedioxythiophene) -Poly (styrnesulfonate), poly (3, 4-ethylenedioxythiophene) -Poly (styrenesulfonate)), pani/CSA (Polyaniline/Camphor sulfonic acid ) or PANI/PSS (Polyaniline/Poly (4-styrenesulfonate)), and the like.
As the hole transporting material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low-molecular or high-molecular materials can also be used. As specific examples, NPB (N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -benzodine, N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -benzidine), NPD (N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -2,2 '-dimethyllbenzidine, N, N' -Bis (naphthalen-1-yl) -N, N '-Bis (phenyl) -2,2' -dimethylbenzidine), mCP (1, 3-Bis (N-carbazolyl) benzene,1, 3-Bis (N-carbazolyl) benzene), TPD (N, N '-Bis (3-methylphenyl) -N, N' -diphenylbenzidine, N, N '-Bis (3-methylphenyl) -N, N' -diphenylbenzidine), TTB (N, N, N ', N' -tetrakis (4-methylphenyl) - (1, 1 '-biphenyl) -4,4-diamine, N, N, N', N '-tetrakis (4-methylphenyl) - (1, 1' -biphenyl) -4, 4-diamine), TTP (N1, N4-diphenyl-N1, N4-dim-tolylzene-1, 4-diamine, N1, N4-di-phenyl-N1, N4-di-m-tolylbenzene-1, 4-diamine), ETPD (N, N '-bis (4-methylphenyl) -N, N' -bis (4-ethylphenyl) - [1,1'- (3, 3' -dimethyl) biphenyl ]]-4,4' -diamine, N ' -bis (4-methylphenyl) -N, N ' -bis (4-ethylphenyl) - [1,1' - (3, 3' -dimethyl) biphenyl]-4,4' -diamine), VNPB (N4, N4' -di (naphthalen-1-yl) -N4, N4' -bis (4-vinylphenyl) biphen-4, 4' -diamine, N4, N4' -di (naphthalen-1-yl) -N4, N4' -bis (4-vinylphenyl) biphenyl-4,4' -diamine), ONPB (N4, N4' -bis (4- (6- ((3-ethyloxy-3-yl) method) phenyl) -N4, N4' -diphenylbiphenyl-4,4' -diamine, N4, low molecular hole transporting substances such as N4' -bis (4- (6- ((3-ethyloxetan-3-yl) methoxy) hexyl) phenyl) -N4, N4' -diphenyl biphenyl-4,4' -diamine), OTPD (N4, N4' -bis (4- (6- ((3-ethyloxetan-3-yl) methoxy) phenyl) -N4, N4' -diphenylbiphenyl-4,4' -diamine, N4' -bis (4- (6- ((3-ethyloxetan-3-yl) methoxy) hexyl) phenyl) -N4, N4' -diphenyl biphenyl-4,4' -diamine)), and the like; and PVK (poly-N-vinylcarbazoles), poly (N-vinylcarbazole), polyaniline, (phenylmethyl) polysilanes
And a polymer hole transporting substance.
As the electron transport material, use can be made of
The metal complex of the diazole derivative, anthraquinone dimethane and its derivative, benzoquinone and its derivative, naphthoquinone and its derivative, anthraquinone and its derivative, tetraquinone dimethane and its derivative, fluorenone derivative, diphenyldicyanoethylene and its derivative, diphenoquinone derivative, 8-hydroxyquinoline and its derivative, etc. may be used, and not only a low molecular substance but also a high molecular substance may be used. As a specific example, TSPO1 (diphenyl [4- (triphenylsilyl) phenyl) can be used]Phosphine oxide, diphenyl [4- (triphenylsilyl) phenyl ]]Phosphine oxide), TPBI (1, 3,5-tris (N-phenylbenzimidzol-2-yl) benzene,1,3, 5-tris (N-phenylbenzimidazol-2-yl) benzene); alq 3 (tris (8-hydroxyquinone) aluminum, tris (8-hydroxy)Quinoline) aluminum); BCP (2, 9-dimethyl-4,7-diphenyl-1, 10-phenanthrine, 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline); PBD (2- (4-biphenyl) -5- (4-tert-butyl-phenyl) -1,3, 4-oxadifole, 2- (4-biphenyl) -5- (4-tert-butyl-phenyl) -1,3, 4-/-for->
Diazoles), TAZ (3- (4-biphenyl) -4-phenyl-5- (4-tert-butyl-phenyl) -1,2,4-triazo le,3- (4-biphenyl) -4-phenyl-5- (4-tert-butyl-phenyl) -1,2, 4-triazole), OXD-7 (1, 3-bis [2- (4-tert-butyl-phenyl) -1,3, 4-oxazo-5-yl)]Benzene,1, 3-bis [2- (4-tert-butylphenyl) -1,3,4->
Diazol-5-yl]Benzene) and the like; tris (phenylquinoxaline) (tris (phenylquinoxaline), TPQ); tmPyPB (3, 3'- [5' - [3- (3-Pyridinyl) phenyl)][1,1’:3’,1”-terphenyl]-3,3”-diyl]bispyridine, 3'- [5' - [3- (3-pyridyl) phenyl ]][1,1':3',1 "-terphenyl group]-3, 3' -diyl]Bipyridine) and the like, but is not limited thereto.
As the electron injection material, LIF or Liq (lithium 8-hydroxyquinoline) is typically used in this field, for example, but not limited thereto.
As the light-emitting material, a red, green, or blue light-emitting material may be used, and if necessary, 2 or more kinds of light-emitting materials may be mixed and used. As the light-emitting material, a fluorescent material or a phosphorescent material may be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, may be used alone, but a material in which a host material and a dopant material participate in light emission at the same time may also be used.
When the heterocyclic compound of chemical formula 1 is used as a host material for a phosphorescent light-emitting layer of an organic light-emitting element, a phosphorescent dopant is used together, whereby a high-luminance color can be obtained with higher efficiency. In this case, the dopant to be used is not limited, and known dopants may be selected and used as needed. The phosphorescent dopant is a compound capable of emitting light from triplet excitons, and is not particularly limited as long as light is emitted from triplet excitons. As a specific example, a metal complex containing one or more metals selected from Ir, ru, pd, pt, os, re and the like may be used, and a porphyrin metal complex or an orthometalated metal complex may be used.
The porphyrin metal complex may specifically be a porphyrin platinum complex.
The orthometalated metal complex may be a compound containing 2-phenylpyridine (2-phenyl pyridine, ppy) derivative, 7, 8-benzoquinoline derivative, 2- (2-thienyl) pyridine (2- (2-thienyl) pyridine, tp) derivative, 2- (1-naphthyl) pyridine (2- (1-naphthyl) pyridine, npy) derivative, 2-phenylquinoline (2-phenyl quinoline, pq) derivative, or the like as a ligand. In this case, the derivatives thereof may have a substituent as required. As the auxiliary ligand, there may be further provided a ligand other than the above-mentioned ligand, such as acetylacetone (acac), picric acid (picric acid), and the like. Specific examples thereof include iridium bithiophene acetylacetonate (bisthienylpyridineacetylacetonate Iridium) and bis (2-benzo [ b ]]Thiophene-2-ylpyridine) (acetylacetonate) iridium (III) (bis (2-benzob)]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III),Ir(btp) 2 (acac)), bis (2-phenylbenzothiazole) (acetylacetonate) iridium (III), ir (bt) 2 (acac)), bis (1-phenylisoquinoline) (acetylacetonate) Iridium (III), iridium (bis (1-phenylisoquinoline) (acetoacetonato) Iridium (III), ir (piq) 2 (acac)), tris (1-phenylisoquinoline) iridium (III), ir (piq) 3 ) Tris (2-phenylpyridine) iridium (III), ir (ppy) 3 ) Tris (2-biphenylpyridine) iridium, tris (3-biphenylpyridine) iridium, tris (4-biphenylpyridine) iridium, and the like, but are not limited thereto.
The present invention will be described in more detail with reference to examples, which are merely illustrative of the present invention and do not limit the scope of the present invention.
Production example 1 production of Compound A1
Production of Compound a-1
To 420mL of DMF was added 10g (84.65 mmol) of benzimidazole, 22.2g (93.11 mmol) of 2-chloro-iodobenzene, 2.42g (12.70 mmol) of CuI (Copper iodide), 23.40g (169.30 mmol) of K 2 CO 3 (potassium carbonate ), 1.12g (4.23 mmol) of 18-crown-6 (18-crown-6-ether) were then refluxed at 150℃under a nitrogen atmosphere. When the reaction was completed, after filtration using celite (celite) and magnesium silicate carrier (florisil), washing with MC was performed. Column chromatography purification using MC and Hex gave 17.2g (89%) of the title compound a-1.
Production of Compound a-2
After dissolving 10g (43.73 mmol) of compound a-1 in 220mL of THF, the temperature was lowered to-78 ℃, 30mL (48.10 mmol) of n-butyllithium (in 1.6M hexane solution) was added, and stirred at the same temperature for 30 minutes. After slowly dropping an iodine (iodine) solution (12.21 g (48.10 mmol) of iodine was dissolved in 200mL of THF), the temperature was raised to room temperature with stirring, and stirred at room temperature for 24 hours. When the reaction was completed, the reaction was stopped with a sodium thiosulfate (sodium thiosulfate) solution, filtered, and washed with MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 11.6g (75%) of the target compound a-2.
Production of Compound a-3
5g (14.10 mmol) of compound a-2, 3.13g (15.51 mmol) of 1-chloro-9H-carbazole, 0.40g (2.12 mmol) of CuI (Copper (I) iodide) and 3.90g (28.20 mmol) of K are added to 420mL of DMF 2 CO 3 (potassium carbonate), 0.19g (0.71 mmol) of 18-crown-6 (18-crown-6-ether) and then refluxed at 150℃under a nitrogen atmosphere. When the reaction is completed, diatomaceous earth (cel) is usedite) and magnesium silicate support (florisil) were filtered and washed with MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 4.1g (68%) of the target compound a-3.
Production of Compound a-4
After dissolving 5g (11.67 mmol) of compound a-3 in 60mL of toluene, 3.85g (15.18 mmol) of bis (pinacolato) diboron (bis (pinacolato) diboron), 1.60g (1.75 mmol) Pd were added 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium (0)), 0.463g (35.02 mmol) of K 2 CO 3 (potassium carbonate), 0.24g (0.58 mmol) of S-Phos (2-Dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl), and refluxed at 130℃for 24 hours. When the reaction is complete, EA and H are used 2 After O extraction, the solvent was removed and purified by Hex and EA column chromatography to give 2.34g (56%) of the target compound a-4.
Production of Compound A1
5g (13.99 mmol) of Compound a-4, 2.99g (16.79 mmol) of N-bromosuccinimide, 3g (100 wt%) of SiO were added to 70mL of chloroform 2 After being wrapped with silver foil, the mixture was stirred at room temperature. When the reaction is completed, MC and H are used 2 After O extraction, the solvent was removed and purified by Hex and EA column chromatography to obtain 1.83g (30%) of the target compound A1.
EXAMPLES 1 to 29 production of Compounds 1-1 to 1-29
Production of Compound A1-1
Suzuki coupling with 3g (6.88 mmol) of Compound A1 was carried out as a conventional process using R 13 The target compound A1-1 having the structure shown in Table 1 below was obtained.
Production of Compounds A1-2
To 10mL of chloroform were added compound A1-1 (1 eq.) and Bromine (1 eq.) and the mixture was wrapped with silver foil and stirred at room temperature. When the reaction was completed, after extraction using a sodium thiosulfate solution (sodium thiosulfate solution) and MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A1-2.
Production of Compound 1
Using the compound A1-2, the objective compound 1 having the structure of table 1 below was obtained by suzuki coupling as a conventional method.
TABLE 1
Production example 2 production of Compound A2
To 70mL of methylene chloride was added 5g (13.99 mmol) of compound a-4, 2.99g (16.79 mmol) of N-bromosuccinimide, 3g (100 wt%) of SiO 2 After being wrapped with silver foil, the mixture was stirred at room temperature. When the reaction is completed, MC and H are used 2 After O extraction, the solvent was removed and purified by Hex and EA column chromatography to give 2.08g (34%) of the target compound A2.
EXAMPLES 30 to 58 preparation of Compounds 2-1 to 2-29
Production of Compound A2-1
Suzuki coupling reaction was carried out as a conventional method using 3g (6.88 mmol) of Compound A2 with R 10 The target compound A2-1 having the structure shown in Table 2 below was obtained.
Production of Compound A2-2
Compound A2-1 (1 eq.) and Bromine (1 eq.) were added to 10mL of chloroform, and the mixture was wrapped with silver foil and stirred at room temperature. When the reaction was completed, after extraction using a sodium thiosulfate solution (sodium thiosulfate solution) and MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A2-2.
Production of Compound 2
Using the compound A2-2, the objective compound 2 having the structure of table 2 below was obtained by suzuki coupling as a conventional method.
TABLE 2
Production example 3 production of Compound A3
Production of Compound a-5
To 420mL of DMF was added 10g (84.65 mmol) of benzimidazole, 25.0g (93.11 mmol) of 1-chloro-2-iodo-4-methoxybenzene, 2.42g (12.70 mmol) of CuI (Copper (I) iodate), 23.40g (169.30 mmol) of K 2 CO 3 (potassium carbonate), 1.12g (4.23 mmol) of 18-crown-6 (18-crown-6-ether) were then refluxed at 150℃under a nitrogen atmosphere. When the reaction was completed, after filtration using celite (celite) and magnesium silicate carrier (florisil), washing with MC was performed. Purification using MC and Hex column chromatography gave 18.4g (84%) of the title compound a-5.
Production of Compound a-6
After dissolving 10g (38.65 mmol) of compound a-5 in 190mL of THF, the temperature was reduced to-78deg.C, then 27mL (42.52 mmol) of n-butyllithium (in 1.6M hexane) was added and stirred at the same temperature for 30 minutes. After slowly dropping an iodine (iodine) solution (10.79 g (42.52 mmol) of iodine (iodine) was dissolved in 170mL of THF), the temperature was slowly raised to room temperature with stirring, and stirred at room temperature for 24 hours. When the reaction was completed, the reaction was stopped with a sodium thiosulfate (sodium thiosulfate) solution, filtered, and washed with MC. Purification using MC and Hex column chromatography gave 11.3g (76%) of the title compound a-6.
Production of Compound a-7
5g (13.0 mmol) of compound a-6, 2.70g (14.30 mmol) of 1-chloro-9H-carbazole, 0.37g (1.95 mmol) of CuI (Copper (I) iodide) and 3.59g (26.0 mmol) of K are added to 420mL of DMF 2 CO 3 (potassium carbonate), 0.18g (0.65 mmol) of 18-crown-6 (18-crown-6-ether) and then refluxed at 150℃under a nitrogen atmosphere. When the reaction was completed, after filtration using celite (celite) and magnesium silicate carrier (florisil), washing with MC was performed. Purification using MC and Hex column chromatography gave 4.2g (71%) of the title compound a-7.
Production of Compound a-8
After dissolving 5g (0.91 mmol) of compound a-7 in 60mL of toluene, 3.85g (15.18 mmol) of bis (pinacolato) diboron (bis (pinacolato) diboron), 1.60g (1.75 mmol) Pd were added 2 (dba) 3 (tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium (0)), 0.463g (35.02 mmol) of K 2 CO 3 (potassium carbonate), 0.24g (0.58 mmol) of S-Phos (2-Dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl), and refluxed at 130℃for 24 hours. When the reaction is complete, EA and H are used 2 After O extraction, the solvent was removed and purified by Hex and EA column chromatography to give 2.20g (52%) of the target compound a-8.
Production of Compound A3
5g (12.91 mmol) of compound a-8, 2.53g (14.20 mmol) of N-bromosuccinimide, 3g (100 wt%) of SiO are added to 70mL of methylene chloride 2 After being wrapped with silver foil, the mixture was stirred at room temperature. When the reaction is completed, MC and H are used 2 After O extraction, the solvent was removed and purified by Hex and EA column chromatography to give 2.47g (41%) of the target compound A3.
EXAMPLES 59 to 87 preparation of Compounds 3-1 to 3-29
Production of Compound A3-1
Suzuki coupling with 3g (6.43 mmol) of Compound A3 was carried out as a conventional process using R 10 The target compound A3-1 having the structure shown in Table 3 below was obtained.
Production of Compound A3-2
Compound A3-1 (1 eq.) and boron tribromide (1 eq.) were added to 10mL of methylene chloride, and stirred at room temperature. When the reaction was completed, after extraction with MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A3-2.
Production of Compound A3-3
To 10mL of THF were added compound A3-2 (1 eq.), triethylamine (1.2 eq.), 4-dimethylaminopyridine (4- (dimethyllamino) pyridine) (0.1 eq.), and trifluoromethanesulfonic anhydride (Triflic anhydride) (1.1 eq.) and the mixture was stirred at room temperature. When the reaction was completed, extraction was performed using MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A3-3.
Production of Compound 3
Using the compound A3-3, the objective compound 3 having the structure of table 3 below was obtained by suzuki coupling as a conventional method.
TABLE 3
PREPARATION EXAMPLE 4 preparation of Compound A4
5g (13.99 mmol) of compound a-8, 2.99g (16.79 mmol) of N-bromosuccinimide, 3g (100 wt%) of SiO are added to 70mL of chloroform 2 After being wrapped with silver foil, the mixture was stirred at room temperature. When the reaction is completed, MC and H are used 2 After O was extracted, the solvent was removed and purified by Hex and EA column chromatography to obtain 1.83g (30%) of the target compound A4.
EXAMPLES 88 to 100 preparation of Compounds 4-1 to 4-13
Production of Compound A4-1
Suzuki coupling with 3g (6.88 mmol) of Compound A4 was carried out as a prior art method using R 13 The target compound A4-1 having the structure shown in Table 4 below was obtained.
Production of Compound A4-2
Compound A4-1 (1 eq.) and boron tribromide (1 eq.) were added to 10mL of methylene chloride, and stirred at room temperature. When the reaction was completed, extraction was performed using MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A4-2.
Production of Compound A4-3
To 10mL of THF were added compound A4-2 (1 eq.), triethylamine (1.2 eq.), 4-dimethylaminopyridine (4- (dimethyllamino) pyridine) (0.1 eq.), and trifluoromethanesulfonic anhydride (Triflic anhydride) (1.1 eq.) and the mixture was stirred at room temperature. When the reaction was completed, extraction was performed using MC, the solvent was removed, and purification was performed by recrystallization from Hex and EA, thereby obtaining the objective compound A4-3.
Production of Compound 4
Using the compound A4-3, the objective compound 4 having the structure of table 4 below was obtained by suzuki coupling as a conventional method.
TABLE 4
The compounds to be produced in the above examples 1 The H NMR and MS values are shown in Table 5 below.
TABLE 5
Manufacture and evaluation of organic electronic components
Experimental examples 1-29 Red organic electroluminescent element (phosphorescent host)
An ITO substrate was placed on a substrate holder of a vacuum deposition apparatus, and a 2-TNATA (4, 4' -Tris [2-naphthyl (phenyl) amino ] triphenylamine, 4' -Tris [2-naphthyl (phenyl) amino ] triphenylamine) film was vacuum deposited on an ITO layer (anode) formed on the glass substrate to form a 60nm thick hole injection layer, and then an NPD (4, 4' -bis [ N- (1-napthyl) -Nphenamino ] biphen) film was vacuum deposited at a thickness of 60nm to form a hole transport layer.
Next, the compound of the present invention described in Table 6 as a host substance was added to one cell in the vacuum vapor deposition apparatus, and (piq) as a red light-emitting dopant substance was added to the other cell 2 Ir (acac) (bis- (1-phenylisoquinolyl) iridium (III) acetate, bis (1-phenylisoquinolyl) acetylacetonate iridium (III)) and then doped at a weight ratio of 95:5, a light-emitting layer was deposited on the hole transport layer at a thickness of 30 nm.
Next, as a hole blocking layer, BAlq (1, 1 '-biphen-4-olato) bis (2-methyl-8-quinolinolato) aluminum, (1, 1' -biphenyl-4-hydroxy) bis (2-methyl-8-hydroxyquinoline) aluminum) was vacuum-deposited at a thickness of 10nm, and as an electron transport layer, alq3 (tris- (8-hydroxyquinoline) aluminum) was vacuum-deposited at a thickness of 40 nm. Then, as an electron injection layer, liF as an alkali metal halide was vapor-deposited at a thickness of 0.2nm, and then Al was vapor-deposited at a thickness of 150nm to form a cathode, thereby producing an organic electroluminescent element.
Comparative examples 1 to 3
An organic light-emitting element was produced in the same manner as in experimental example 1 above, except that the following comparative compound a, comparative compound B, or comparative compound C was used instead of the compound of the present invention as the host material of the light-emitting layer.
The organic electroluminescent devices manufactured by the experimental examples 1 to 29 and comparative examples 1 to 3 of the present invention were applied with a forward bias direct current voltage, and the Electroluminescent (EL) characteristics were measured by PR-650 of the company Photoesearch, at 2500cd/m 2 The T90 lifetime was measured at the reference luminance by a lifetime measuring apparatus manufactured by McScience corporation, and the measurement results are shown in table 6 below. T90 represents the time taken until the luminance of the light-emitting element becomes 90% with respect to the initial luminance.
TABLE 6
As is clear from table 6, the compounds developed in the present invention have more excellent light emission characteristics than conventional light emitting materials as red light emitting materials, and can reduce driving voltage, induce an increase in power utilization coefficient, and improve power consumption. That is, the compound according to the present invention has an advantage that an OLED having good luminous efficiency and very good driving life of the element can be manufactured as a host material for a light emitting material compared to the existing host material.
Experimental examples 30-63 Green organic electroluminescent element (phosphorescent host)
Transparent electrode ITO film obtained from OLED glass (Sanxing-Kangning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water in this order, and then stored in isopropanol.
Secondly, arranging the substrate clamp of the vacuum evaporation equipmentAn ITO substrate, and 2-TNATA is added into a pool in a vacuum evaporation device. Then, exhausting is performed until the vacuum degree in the cavity reaches 10 -6 A support, then a current 2-TNATA is applied to the cell, and the ITO substrate is evaporated
A hole injection layer of thickness. NPB is added into another pool in the vacuum evaporation equipment, current is applied to the pool to evaporate the pool, and +.>
A hole transport layer of thickness.
After the hole injection layer and the hole transport layer were formed in this manner, the light-emitting layer was evaporated thereon as follows. As a main substance, the compounds of the present invention described in Table 7 were used as
Vacuum deposition was performed at the same time as the thickness of Ir (ppy) as a green-emitting dopant substance 3 (Tris (2-phenylpyridine) iridium (III), tris (2-phenylpyridine) iridium) was vacuum evaporated by 10% relative to the host material.
Subsequently, as a hole blocking layer, BCP (2, 9-dimethyl-4,7-diphenyl-1, 10-phenanthrine, 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline) was used as a hole blocking layer
Vapor deposition was performed to a thickness of Alq3 as an electron transport layer>
Is vapor deposited.
Then, as an electron injection layer, liF was used as
Is vapor deposited. Then, al is cathodic in +.>
Vapor deposition is performed to the thickness of (2) to produce an organic electroluminescent device.
Comparative examples 4 and 5
An organic light-emitting element was produced in the same manner as in experimental example 30 above, except that the following comparative compound a or comparative compound C was used as the host material of the light-emitting layer in place of the compound of the present invention.
The driving voltage, efficiency and life of the elements fabricated in examples 30 to 63 and comparative examples 4 to 5 of the present invention were 1000cd/m 2 And the results at 50% efficiency are shown in Table 7 below.
TABLE 7
From the above table 7, it was confirmed that the compounds developed in the present invention as green light emitting materials exhibited similar or superior light emitting characteristics as compared with the conventional light emitting materials. In particular, the driving voltage can be reduced, the induced power utilization coefficient can be increased, and the power consumption can be improved. That is, the compound according to the present invention has an advantage that an OLED having good luminous efficiency and very good driving life of the element can be manufactured as a host material for a light emitting material compared to the existing host material.
Claims (4)
1. A heterocyclic compound represented by any one of the following chemical formulas 3 to 6:
chemical formula 3
Chemical formula 4
Chemical formula 5
Chemical formula 6
In the chemical formulas 3 to 6, R 21 To R 24 Each independently is hydrogen;
*-L 1 -Ar 1 、*-L 2 -Ar 2 、*-L 3 -Ar 3 and-L 4 -Ar 4 Each independently selected from the following structures;
2. the heterocyclic compound of claim 1, wherein the heterocyclic compound is selected from the following structures:
3. an organic light emitting element, comprising: an anode, a cathode, and an organic layer comprising 1 or more layers between the anode and the cathode, wherein 1 or more layers of the organic layer contain the heterocyclic compound according to claim 1 or 2.
4. The organic light-emitting element according to claim 3, wherein the organic layer is at least one layer selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010218466.4A CN113444098B (en) | 2020-03-25 | 2020-03-25 | Novel heterocyclic compound and organic light-emitting element comprising same |
| KR1020200068863A KR102214260B1 (en) | 2020-03-25 | 2020-06-08 | Novel heterocyclic compound and organic light emitting device comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010218466.4A CN113444098B (en) | 2020-03-25 | 2020-03-25 | Novel heterocyclic compound and organic light-emitting element comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113444098A CN113444098A (en) | 2021-09-28 |
| CN113444098B true CN113444098B (en) | 2023-04-25 |
Family
ID=74561281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010218466.4A Active CN113444098B (en) | 2020-03-25 | 2020-03-25 | Novel heterocyclic compound and organic light-emitting element comprising same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102214260B1 (en) |
| CN (1) | CN113444098B (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356429A (en) * | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
| JP4356429B2 (en) | 2003-11-10 | 2009-11-04 | ブラザー工業株式会社 | ink cartridge |
| KR101616501B1 (en) * | 2013-09-11 | 2016-04-28 | 희성소재 (주) | Multicyclic compound including nitrogen and organic light emitting device using the same |
| TWI589673B (en) * | 2016-11-03 | 2017-07-01 | 元智大學 | Bipolar materials and organic light emitting diodes |
| US10910570B2 (en) * | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2020
- 2020-03-25 CN CN202010218466.4A patent/CN113444098B/en active Active
- 2020-06-08 KR KR1020200068863A patent/KR102214260B1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR102214260B1 (en) | 2021-02-10 |
| CN113444098A (en) | 2021-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7314364B2 (en) | Organic electroluminescent compound and organic electroluminescent device containing the same | |
| CN111052428B (en) | Organic light-emitting device using heterocyclic compound | |
| CN111094302B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN111655706B (en) | Compound and organic light emitting device comprising the same | |
| TWI469966B (en) | Compound having carbazole ring structure, and organic electroluminescent device | |
| CN113227082B (en) | Compound and organic light emitting device using the same | |
| CN110088110B (en) | Novel compound and organic light-emitting element comprising same | |
| CN111770919B (en) | Compound and organic light emitting device including the same | |
| KR20110015836A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20190101281A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| CN111377905A (en) | Organic electroluminescent material and device | |
| CN110800122A (en) | Organic electroluminescent device | |
| JP2021093526A (en) | Organic electro-luminescent compound and organic electro-luminescent device including the same | |
| KR20200068568A (en) | Novel compound and organic light emitting device comprising the same | |
| KR101616501B1 (en) | Multicyclic compound including nitrogen and organic light emitting device using the same | |
| KR102173481B1 (en) | New organic electroluminescent compound and organic electroluminescent device comprising the same | |
| CN111699178B (en) | Compound and organic light emitting device comprising the same | |
| CN113444098B (en) | Novel heterocyclic compound and organic light-emitting element comprising same | |
| CN111670192B (en) | Compound and organic light emitting device comprising the same | |
| KR20230108910A (en) | Benzosilolocarbazole compound and organic electroluminescence device comprising the same | |
| KR20140023283A (en) | Compound containing substituted o-terphenyl structure, and organic electroluminescent element | |
| CN110291077B (en) | Novel heterocyclic compound and organic light emitting device comprising the same | |
| KR102541384B1 (en) | Novel heterocyclic compound and organic light emitting device comprising the same | |
| CN111212829A (en) | Spiro compound and organic light-emitting device comprising same | |
| CN111051323A (en) | Compound and organic light emitting device including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |