CN115960113A - Novel organic compound and organic electroluminescent device comprising the same - Google Patents
Novel organic compound and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- CN115960113A CN115960113A CN202211230429.0A CN202211230429A CN115960113A CN 115960113 A CN115960113 A CN 115960113A CN 202211230429 A CN202211230429 A CN 202211230429A CN 115960113 A CN115960113 A CN 115960113A
- Authority
- CN
- China
- Prior art keywords
- group
- organic
- carbon atoms
- carbon number
- organic electroluminescent
- 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.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 bisphenyl Chemical group 0.000 claims description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 125000001725 pyrenyl group Chemical group 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 9
- 150000003573 thiols Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 150000003852 triazoles Chemical class 0.000 claims description 7
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- FRIPRWYKBIOZJU-UHFFFAOYSA-N fluorone Chemical compound C1=CC=C2OC3=CC(=O)C=CC3=CC2=C1 FRIPRWYKBIOZJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 103
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 21
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 11
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000002207 thermal evaporation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 230000005281 excited state Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 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 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 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 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- LDJKKLGZOYXYHE-UHFFFAOYSA-N 1,1'-biphenyl buta-1,3-diene Chemical compound C=CC=C.C1=CC=CC=C1C1=CC=CC=C1 LDJKKLGZOYXYHE-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- QKLPIYTUUFFRLV-UHFFFAOYSA-N 1,4-bis[2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=CC=C1C QKLPIYTUUFFRLV-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- KRQMWLQSKCQPTI-UHFFFAOYSA-N 2,5,8,11-tetrabutylperylene Chemical group CCCCC1=CC(C2=CC(CCCC)=CC=3C2=C2C=C(CCCC)C=3)=C3C2=CC(CCCC)=CC3=C1 KRQMWLQSKCQPTI-UHFFFAOYSA-N 0.000 description 1
- TWZYORZPYCRVAX-UHFFFAOYSA-N 2-(2h-thiopyran-1-ylidene)propanedinitrile Chemical compound N#CC(C#N)=S1CC=CC=C1 TWZYORZPYCRVAX-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-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
- VLDFXDUAENINOO-UHFFFAOYSA-N 4-methyl-2-[4-(4-methyl-5-phenyl-1,3-oxazol-2-yl)phenyl]-5-phenyl-1,3-oxazole Chemical compound CC=1N=C(C=2C=CC(=CC=2)C=2OC(=C(C)N=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 VLDFXDUAENINOO-UHFFFAOYSA-N 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
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 1
- 241000408947 Celotes Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- INQOMBQAUSQDDS-MICDWDOJSA-N deuterio(iodo)methane Chemical compound [2H]CI INQOMBQAUSQDDS-MICDWDOJSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N p-hydroxybiphenyl Natural products C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical class [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
- C07D495/06—Peri-condensed systems
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- 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
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present invention provides an organic compound represented by the following formula 1 and an organic electroluminescent device including the organic compound: general formula 1
Description
Technical Field
The invention relates to the field of display screens, in particular to an organic compound used in the manufacture of an organic electroluminescent device of a display screen and an organic electroluminescent device containing the compound.
Background
So far, most of the flat panel displays are liquid crystal displays, but there has been a continuous active effort to develop new flat panel displays which are more economical, have more superior performance, and are different from the liquid crystal displays all over the world. Recently, organic electroluminescent devices, which have attracted attention as next-generation flat panel displays, have advantages such as low driving voltage, high response speed, and wide viewing angle, as compared to liquid crystal displays.
According to the structure of the organic electroluminescent device, the organic electroluminescent device is composed of a substrate, an anode, a hole injection layer for receiving holes from the anode, a hole transport layer for transporting holes, an electron blocking layer for blocking electrons from entering the hole transport layer from the light emitting layer, a light emitting layer for emitting light by combining holes and electrons, a hole blocking layer for blocking holes from entering the electron transport layer from the light emitting layer, an electron transport layer for receiving electrons from the cathode and transporting the electrons to the light emitting layer, an electron injection layer for receiving electrons from the cathode, and a cathode. In the case of using a polymer, generally, one polymer may simultaneously perform the roles of the hole transport layer and the emission layer as well as the electron transport layer. The organic thin film layer between the two electrodes can be formed by a vacuum deposition method, a spin coating method, ink jet printing, laser hot stamping, or the like. In order to stabilize the interface between the electrode and the organic material, and in the case of using an organic material, since the difference in the moving speed between holes and electrons is large, the organic electroluminescent device is fabricated in a multi-layer thin film structure, and thus, the holes and the electrons are efficiently transferred to the light-emitting layer by using an appropriate hole transport layer and an appropriate electron transport layer, and the density of the holes and the electrons is equalized, thereby improving the light-emitting efficiency.
The driving principle of the organic electroluminescent device is as follows: when a voltage is applied between the anode and the cathode, holes injected from the anode are transferred to the light-emitting layer through the hole injection layer and the hole transport layer. At the same time, electrons are injected from the cathode into the light-emitting layer via the electron injection layer and the electron transport layer, and recombine with carriers in the light-emitting layer to form excitons. The excitons change to the ground state in this state, and thereby fluorescent molecules of the light-emitting layer emit light to form an image. At this time, the excited state returns to the ground state through the singlet excited state, and the emitted light is called "fluorescence"; the light emitted is called "phosphorescence" by returning to the ground state through the triplet excited state. The probability of returning to the base state by the singlet excited state is 25% (the probability of returning to the triplet excited state is 75%), and therefore, the light emission efficiency is limited. When phosphorescence is used, 75% of the triplet state and 25% of the singlet excited state can be used for light emission, and thus, theoretically, the internal quantum efficiency can reach 100%.
The biggest problems of such organic electroluminescent devices are lifetime and luminous efficiency, which must be solved as the display screen becomes larger in area.
In particular, blue color, although substances such as ADN and DPVBi can be used as host substances and substances such as aromatic amine compounds, phthalocyanine copper compounds, carbazole derivatives, perylene derivatives, coumarin derivatives, and pyrene derivatives can be used as dopants, it is difficult to obtain deep blue color and there is a problem that the lifetime becomes shorter as the wavelength becomes shorter.
Therefore, in the full color display that displays natural colors, development of a material that can emit deep blue light with a long service life and another organic material that is suitable for the energy level of such a blue material is strongly demanded.
Disclosure of Invention
Problems to be solved
The invention aims to solve the defects in the prior art.
The invention provides a blue fluorescent doping substance, thereby improving the luminous efficiency and the luminous life of an organic electroluminescent device.
In addition, the present invention aims to provide an organic electroluminescent device which reduces a driving voltage, improves luminous efficiency and extends a luminous life by including the blue dopant as described above.
In addition, the present invention aims to provide an organic electroluminescent device which further improves the driving voltage, the luminous efficiency of the device and the luminous life by combining a substance containing the above-mentioned blue dopant and a substance containing a specific hole transport layer.
Means for solving the problems
The present invention provides an organic compound represented by the following general formula 1:
general formula 1
In the above formula
R1, R2, R3, R4, R5, R6, R7 and R8 are respectively and independently selected from hydrogen, deuterium, oxygen, F, cl, br, I, CN, si (CH) 3 ) 3 、B(OH) 2 Straight or branched chain alkyl of carbon number 1 to 40, alkoxy of carbon number 1 to 40, thiol of carbon number 1 to 40, or cycloalkyl of carbon number 3 to 40.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 The aromatic hydrocarbon group with 6 to 80 carbon atoms comprises more than one of the group consisting of straight chain or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, mercaptan with 1 to 40 carbon atoms, cycloalkyl with 3 to 40 carbon atoms, phenyl, diphenyl, naphthyl, anthryl phenanthryl pyrenyl 9,9-difluorene carbazole dibenzofuran pyrrole triazole type aminobenzopyrazine pyrimidine quinoline substituted by phenyl.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 Straight chain or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thiol of 1 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, bisphenyl, naphthyl, anthryl substituted with phenyl, phenanthryl, pyrenyl, 9,9-dimethylfluorene, spirobi [ fluorone ]]Carbazole, dibenzofuran, pyrrole, triazole, aminobenzene, pyrazine, pyrimidine and quinolineOne or more substituted or unsubstituted heteroaromatic hydrocarbon groups having a carbon number of 5 to 90 and containing one or more elements selected from the group consisting of S, O, N and Si.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 One or more substituted or unsubstituted phenyl, bisphenyl, naphthyl, anthryl substituted with phenyl, phenanthryl, pyrenyl, 9,9-dimethylfluorene, carbazole, quinoline, dibenzofuran, pyrrole, triazoles, aminobenzene, pyrazine, pyrimidine and the like selected from the group consisting of straight-chain or branched chain alkyl groups having a carbon number of 1 to 40, alkoxy groups having a carbon number of 1 to 40, thiol having a carbon number of 1 to 40 and cycloalkyl groups having a carbon number of 3 to 40.
Z1 and Z2 are respectively independent single combination or double combination.
M1 and M2 are respectively and independently carbon or nitrogen or oxygen or sulfur.
In addition, the present invention provides an organic electroluminescent device in which one or more organic thin film layers including at least a light-emitting layer are stacked between a cathode and an anode.
The organic electroluminescent element is characterized in that the light-emitting layer contains one or more organic compounds of the present invention.
The organic thin film layer in the above organic electroluminescent device may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer,
the hole transport layer may contain one or more than two organic compounds of the following formula 2:
general formula 2
In the above-mentioned formula, the compound has the following formula,
r1, R2, R3 and R4 are each independently selected from hydrogen; a linear or branched alkyl group having a carbon number of 1 to 20; to be selected from
Or linear or branched alkyl or>
Alkoxy, halogen, CN, CF of 3 And Si (CH) 3 ) 3 An aromatic hydrocarbon group having 6 to 60 carbon atoms in the group consisting of one or more substituted or unsubstituted carbon atoms; or in a manner selected from the group consisting of>
Is straight-chain or branched alkyl and/or is branched alkyl>
Alkoxy of , CN, CF 3 And Si (CH) 3 ) 3 One or more substituted or unsubstituted heteroaromatic hydrocarbon groups having a carbon number of 5 to 60 and containing one or more elements selected from the group consisting of S, O, N and Si,
r1, R2, R3 and R4 are each independently bonded to a phenyl group of the basic structure to form an aromatic hydrocarbon group or a heteroaromatic hydrocarbon group.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention provides novel organic compounds useful as blue dopant species for improving the luminous efficiency and luminous lifetime of organic electroluminescent devices.
In addition, the present invention provides an organic electroluminescent device that improves driving voltage, luminous efficiency and luminous lifetime by including the blue dopant as described above.
In addition, the present invention provides an organic electroluminescent device which improves driving voltage, luminous efficiency and luminous lifetime by combining a material containing the above blue dopant and a specific hole transport layer.
Detailed Description
The present invention relates to a novel organic compound represented by the following formula 1:
general formula 1
In the above formula
R1, R2, R3, R4, R5, R6, R7 and R8 are respectively and independently selected from hydrogen, deuterium, oxygen, F, cl, br, I, CN and Si (CH) 3 ) 3 、B(OH) 2 Straight chain or branched chain alkyl with carbon number of 1 to 40, alkoxy with carbon number of 1 to 40, mercaptan with carbon number of 1 to 40, or cycloalkyl with carbon number of 3 to 40.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 Straight-chain or branched alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thiol with 1 to 40 carbon atoms, cycloalkyl with 3 to 40 carbon atoms, phenyl, diphenyl, naphthyl, anthryl substituted by phenyl, phenanthryl, pyrenyl, 9,9-difluorene, carbazole, dibenzofuran, pyrrole, triazole, aminobenzene, pyrazine, pyrimidine and quinoline, and one or more substituted or unsubstituted aromatic hydrocarbon groups with 6 to 80 carbon atoms.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 Straight chain or branched chain alkyl with carbon number of 1 to 40, alkoxy with carbon number of 1 to 40, mercaptan with carbon number of 1 to 40, cycloalkyl with carbon number of 3 to 40, phenyl, bisphenyl, naphthyl, anthryl substituted by phenyl, phenanthryl, pyrenyl, 9,9-difluorene, spirobi [ fluorolene]One or more substituted or unsubstituted heteroaromatic hydrocarbon groups having a carbon number of 5 to 90, and containing one or more elements selected from the group consisting of S, O, N and Si.
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 More than one substituted or non-substituted phenyl, diphenyl, naphthyl, anthryl, or phenyl substituted by phenyl, straight-chain or branched chain alkyl with 1 to 40 carbon atoms, alkoxyl with 1 to 40 carbon atoms, thiol with 1 to 40 carbon atoms, or cycloalkyl with 3 to 40 carbon atomsSubstituted anthracenyl, phenanthryl, pyrenyl, 9,9-difluorene, carbazole, quinoline, dibenzofuran, pyrrole, triazoles, aminobenzene, pyrazine, pyrimidine and the like.
Z1 and Z2 are respectively independent single combination or double combination.
M1 and M2 are respectively and independently carbon or nitrogen or oxygen or sulfur.
Specific examples of the organic compound include any of the following compounds 1 to 352.
In addition, the present invention
An organic electroluminescent device is provided, which has one or more organic thin film layers having at least a light-emitting layer laminated between a cathode and an anode.
The organic electroluminescent element is characterized in that the light-emitting layer contains one or two or more of the organic compounds.
The organic thin film layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
The hole transport layer may contain one or more than two organic compounds of the following formula 2:
general formula 2
In the above-mentioned formula, the compound of formula,
r1, R2, R3 and R4 are each independently selected from hydrogen; a linear or branched alkyl group having a carbon number of 1 to 20; to be selected from
Is straight-chain or branched alkyl and/or is branched alkyl>
Alkoxy, halogen, CN, CF of 3 And Si (CH) 3 ) 3 Aromatic hydrocarbon groups of 6 to 60 carbon numbers of one or more substituted or unsubstituted carbons in the group; or is selected from the group consisting of>
Is straight-chain or branched alkyl and/or is branched alkyl>
Alkoxy of , CN, CF 3 And Si (CH) 3 ) 3 One or more substituted or unsubstituted heteroaromatic hydrocarbon groups having a carbon number of 5 to 60 and containing one or more elements selected from the group consisting of S, O, N and Si,
r1, R2, R3 and R4 are each independently bonded to a phenyl group of the basic structure, and can form an aromatic hydrocarbon group or a heteroaromatic hydrocarbon group.
In the above formula, more preferred is
R1, R2, R3 and R4 are each independently phenyl, bisphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, carbazole or pyrenyl,
or the above R1, R2, R3 and R4 are each independently combined with a phenyl group of the basic structure to form naphthalene, anthracene or phenanthrene.
Specific examples of the organic compound include any of the following compounds 101 to 112.
The following will exemplify the organic electroluminescent device to which the present invention relates. However, the following descriptions do not limit the organic electroluminescent device according to the present invention.
The manufacturing method of the organic electroluminescent device comprises the following steps: first, an anode material is overmolded on the surface of a substrate by a conventional method to form an anode, and the substrate used is a glass substrate or a transparent plastic substrate having good transparency, surface smoothness, handleability, and water resistance. As the anode material, transparent Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) having excellent conductivity can be used 2 ) Zinc oxide (ZnO), and the like.
And then, carrying out vacuum thermal deposition or spin coating on the surface of the anode by using a hole injection layer material (HIL) by adopting a conventional method to form the hole injection layer. The hole injection layer material may be CuPc, m-MTDATA, m-MTDAPB, TCTA of the star amine type, 2-TNATA, or IDE406 commercially available from Idemitsu, japan.
And (3) carrying out vacuum thermal deposition or spin coating on the surface of the hole injection layer by using a conventional method to form the hole transport layer. The hole transport layer material may be alpha-NPD, NPB, or TPD. More preferably, the compound of formula 2 of the present invention is used.
And (3) carrying out vacuum thermal deposition or spin coating on the surface of the hole transport layer by using a conventional method to form the light-emitting layer. The luminescent material can be light-storing fluorescent material, fluorescent brightener, laser pigment, organic scintillator, fluorescence analysis reagent, etc. Specifically, there are carbazole compound, phosphine oxide compound, carbazole phosphine oxide compound, FCNIRpic, alq 3 Anthracene, phenanthrene, pyrene, celot, perylene, coronene, rubrene and polycyclic aromatic compounds like quinacridones, phenylene compounds like quaterphenyl1,4 bis (2-methylstyryl) benzene, 1,4 bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1,4 bis (5-phenyl 2_ sitting) phenyl, 2,5 bis (5_t _ butyl _2_ benzoxazole sitting) thiophene, 1,4_ biphenyl-1, 3 butadiene, 1,6_ biphenyl-1,3,5-hexatriene, scintillators for liquid scintillation like 1,1,4,4-tetraphenyl-1,3-butadiene, metal carriers for auxin derivatives, coumarin, dicyanomethylene pigments, dicyanomethylene thiopyran pigments, polymethine pigments, hydroxybenzophenone pigments, quinolone pigments, perylene pigments, stilbene compounds, oxadiazole derivatives, stilbene derivatives. In the case of a blue organic electroluminescent device in particular, it is more preferable to use the organic compound of the general formula 1 of the present invention as a dopant.
Optionally, an Electron Blocking Layer (EBL) may be added between the hole transport layer and the light emitting layer.
And (3) carrying out vacuum thermal deposition or spin coating on the surface of the light-emitting layer by adopting a conventional method to form the electron transport layer. The electron transport layer material is not particularly limited, and Alq is preferably used 3 。
Optionally, a Hole Blocking Layer (HBL) may be further added between the light emitting layer and the electron transporting layer, and a phosphorescent dopant is used together with the light emitting layer, so that an effect of preventing triplet excitons from being diffused to the electron transporting layer may be achieved.
And carrying out vacuum thermal deposition or spin coating on the surface of the light-emitting layer by adopting a conventional method to form the hole blocking layer. The hole blocking layer material is not particularly limited, and Liq, 2_ methyl-8-hydroxyquinoline p-hydroxybiphenyl aluminum (BCP), liF, and the like are preferable.
And (3) carrying out vacuum thermal deposition or spin coating on the surface of the electron transport layer by using an electron injection layer material (EIL) by using a conventional method to form the electron injection layer. The material of the electron injection layer can be LiF, liq and Li 2 O, baO, naCl, csF, etc.
And (3) carrying out vacuum thermal deposition or spin coating on the cathode material on the electron injection layer by adopting a conventional method to form the cathode.
The cathode material used at this time may be Li, al-Li, ca, mg-In, mg-Ag, or the like. In addition, the organic electroluminescent device may be made into a light-transmitting transparent cathode using Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO).
According to the above-mentioned coating composition, a coating layer (CPL) can be further formed on the surface of the cathode.
According to the above-described method for manufacturing an organic electroluminescent device, it can be manufactured in the order of anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode, and similarly, it can be manufactured in the order of cathode/electron injection layer/electron transport layer/light-emitting layer/hole transport layer/hole injection layer/anode.
The synthesis of compounds of formula 1 and formula 2 is illustrated below by way of example. However, the following methods are not intended to limit the synthesis method of the compound according to the present invention, and the compound according to the present invention can be produced by the following methods and methods known in the art.
Synthesis of Compounds of formula 1
Synthesis of intermediate-2
A5L three-necked round-bottomed flask was charged with intermediate-1.8g, copper 170.9g, and N, N-dimethylformamide 3L, and the mixture was refluxed for 12 hours. After completion of the reaction, the N, N-dimethylformamide was distilled, dissolved in 1L of ethyl acetate, and then filtered through celite. The reaction mixture was concentrated, filtered and dried after using 1L of methanol slurry for 30 minutes, to obtain 254.6g of intermediate-2 in 86% yield.
Intermediate-2 MS (FAB): 330 (M +)
Synthesis of intermediate-3
A5L three-neck round-bottom flask was charged with intermediate-2.254.6 g, dissolved with MC 3L. The mixture was placed in an ice bath, and boron tribromide was slowly added. After removing the ice bath, the temperature was raised to normal temperature, and after confirming that the reaction was completed, 1L of sodium carbonate was gradually added, and after extracting the organic layer, distillation was performed, and thus 172.6g of intermediate-3.6 g was obtained in 94% yield by n-Hexane/MC recrystallization.
Intermediate-3 MS (FAB): 238 (M +)
Synthesis of intermediate-4
Intermediate-3.7 g was added to a 2L three neck round bottom flask and fused in 1.5L of LTHF. The mixture was placed in an ice bath, and 42.5g of lithium aluminum hydride was finely divided and then added slowly. Removing ice bath, heating to normal temperature and stirring for 3 hours. After completion of the reaction, an ice bath was set up, and saturated ammonium chloride was slowly added for neutralization. The THF layer was extracted, then distilled and passed through a chromatography column to obtain intermediate-4.3g in 82% yield.
Intermediate-4 MS (FAB) 210 (M +)
Synthesis of intermediate-5
24.9g of intermediate-4 was charged into a 1L three-necked round-bottomed flask, and the mixture was dissolved in 500ml of N, N-dimethylformamide, and 23.2g of N-bromosuccinimide was added slowly while maintaining 0 ℃ after the ice bath was made. After removing the ice bath and raising the temperature to normal temperature, the reaction was completed by distilling N, N-dimethylformamide and passing through a chromatographic column to obtain intermediate-5 26g in 76% yield.
Intermediate-5 MS (FAB): 289 (M +)
Synthesis of intermediate-6
Intermediate-4.4 g was added to a 500ML three-necked round bottom flask and fused to MC 200 ML. After an ice bath was set, 45.4g of N-bromosuccinimide was slowly added, and the temperature was raised to normal temperature by removing the ice bath. After the completion of the reaction, 200ml of water was added to extract the organic layer, and the mixture was subjected to distillation and chromatography to obtain intermediate-6.2g in 93% yield.
Intermediate-6 MS (FAB): 368 (M +)
Synthesis of intermediate-7
Intermediate-3 119g was added to a 3L three-necked round bottom flask and 1L sulfuric acid was added. An ice bath was set up and then 95g of fuming nitric acid was slowly added. After removing the ice bath, the reaction mixture was stirred at room temperature for 1 hour, after confirming completion of the reaction, the reaction mixture was slowly added to ice water, and the resultant solid was washed with water and dried upon filtration to obtain intermediate-7.3g in a yield of 88%.
Intermediate-7 MS (FAB): 328 (M +)
Synthesis of intermediate-8
Intermediate-7.3g was charged to a 5L three-necked round bottom flask followed by 2L of acetic acid. 300ml of concentrated hydrochloric acid was added, and 245.5g of iron was added while stirring, and the mixture was refluxed for 3 hours, and then filtered through diatom ooze in a scalded state after completion of the reaction. Acetic acid was distilled and recrystallized from n-Hexane/MC to obtain intermediate-8.2g in 68% yield.
Intermediate-8 MS (FAB): 268 (M +)
Synthesis of intermediate-9
Intermediate-8.2g was added to a 2L three-necked round bottom flask and dissolved in MC 1L. After the ice bath was placed, 117.1g of N-bromosuccinimide was slowly added, and after completion of the reaction was confirmed by removing the ice bath at room temperature, 500ml of water was added and stirred for 30 minutes, N-Hexane 1L was added to the extraction MC layer, then MC was distilled, and the resulting solid was filtered to obtain 117.2g of an intermediate in 92% yield.
Intermediate-9 MS (FAB) 426 (M +)
Synthesis of intermediate-10
Intermediate-9.2g was added to a 5L three-necked round bottom flask, and 2L ethanol was added. After adding 200g of sulfuric acid, sodium nitrite was slowly added while stirring. After heating and refluxing for 3 hours, the reaction was confirmed to be completed and then cooled at room temperature. 1L of water was added and ethanol was distilled, and the resulting solid was washed with water, filtered and recrystallized from n-Hexane/MC to obtain intermediate-10.7 g in a yield of 53%.
Intermediate-10 MS (FAB): 395 (M +)
Synthesis of intermediate-11
A2L three-necked round bottom flask was charged with 57.7g of intermediate-dissolved in THF1.5L, and after setting an ice bath, 22.1g of lithium aluminum hydride was finely divided and slowly added. Removing ice bath, heating to normal temperature and stirring for 3 hours. After completion of the reaction, an ice bath was set up, saturated ammonium chloride was slowly added to neutralize the reaction solution, and after extraction of a THF layer, 38.6g of an intermediate was obtained by distillation and chromatography.
Intermediate-11 MS (FAB): 368 (M +)
Synthesis of intermediate-12
A1L three-necked round-bottomed flask was charged with 38.6g of the intermediate-11, and then charged with nitrogen. THF400ml was added and the temperature was maintained at-78 ℃ with an acetone/dry ice bath. 72ml of 1.6M n-butyllithium was added dropwise thereto, the mixture was stirred for 30 minutes, 50ml of methanol was added thereto, the mixture was heated to room temperature, 200ml of saturated ammonium chloride was added thereto, a THF layer was extracted, the solvent was distilled, and then the mixture was passed through a column chromatography to obtain 1226.4g, which is an intermediate, in 87% yield.
Intermediate-12 MS (FAB): 289 (M +)
Synthesis of intermediate-13
A3L three neck round bottom flask was charged with intermediate-8.7 g dissolved in acetonitrile 1.5L. 131g of cupric bromide was added thereto, and the mixture was stirred and heated to 60 ℃. After adding 45.4g of tert-butyl nitrite slowly, stirring was carried out for 1 hour to confirm that the reaction was completed and cooled at room temperature. 1N HCl 1.5L and EA 1.5L were added, the mixture was stirred for 30 minutes, the organic layer was extracted, the mixture was distilled, and the mixture was recrystallized from n-Hexane/MC to obtain intermediate-13 72g in a yield of 62%.
Intermediate-13 MS (FAB): 395 (M +)
Synthesis of intermediate-14
Intermediate-13 72g was added to a 3L three-necked round bottom flask dissolved in THF2L. An ice bath was set, 27.6g of lithium aluminum hydride was finely divided, and then the mixture was slowly added thereto, and the ice bath was removed, and the mixture was heated to room temperature and stirred for 3 hours. After completion of the reaction, an ice bath was set, and saturated ammonium chloride was slowly added for neutralization. The THF layer was extracted and distilled over a chromatographic column to give 14.5g of intermediate in 65% yield.
Intermediate-14 MS (FAB): 368 (M +)
Synthesis of intermediate-15
A1L three-necked round-bottomed flask was charged with intermediate-14.7 g, nitrogen gas was charged, THF300ml was added, an acetone/dry ice bath was maintained at a temperature of-78 ℃ and 38ml of 1.6M n-butyllithium was added dropwise thereto, the mixture was stirred for 30 minutes, then 50ml of methanol was added thereto, the temperature was raised to room temperature, 200ml of saturated ammonium chloride was added thereto, the THF layer was extracted, the solvent was distilled, and then intermediate-1516.3 g was obtained in 84% yield by chromatography.
Intermediate-15 MS (FAB): 289 (M +)
Synthesis of intermediate-19
After adding intermediate-6 g and intermediate-18.63g to a 250ML three-necked round-bottomed flask, 100ML of toluene and 10ML of ethanol were added, 28ML of 2M potassium carbonate and 4.08g of Pd (PPh 3) were further added, and the mixture was refluxed for 12 hours. After confirming the completion of the reaction, the organic layer was distilled off, and recrystallized after passing through a column, whereby 19.13g of intermediate was obtained in a yield of 45%.
Intermediate-19 MS (FAB): 491 (M +)
Synthesis of intermediate-20
A250 ML three-necked round-bottomed flask was charged with intermediate-6 10g, charged with nitrogen gas dissolved in 100ML of THF, and then charged with 19ML of 1.6M n-butyllithium while maintaining a dry-ice bath at-78 ℃. After 30 minutes, 4.7g of iodomethane-D is added, stirred for 10 minutes, removed from the ice bath and heated to normal temperature. After confirming the completion of the reaction, THF was distilled off, and after passing through a chromatography column, 207.2g of intermediate was obtained in 86% yield.
Intermediate-20 MS (FAB): 306 (M +)
Synthesis of intermediate-21
A250 ML three-necked round bottom flask was charged with intermediate-6, 10g, and filled with nitrogen gas dissolved in 100ML of THF. 19ml of 1.6M n-butyllithium was slowly dropped while maintaining a temperature of-78 ℃ in an acetone/dry ice bath. After 30 minutes, 4.6g of methyl iodide was added, followed by stirring for 10 minutes, ice bath was removed, the temperature was raised to normal temperature, THF was distilled after completion of the reaction was confirmed, and 216.8g of an intermediate was obtained in 83% yield after passing through a column.
Intermediate-21 MS (FAB): 303 (M +)
Synthesis of intermediate-22
1.69g (10 mmol) of [1,1' -ethylene ] -4-amine and 4-iodo-1,1 ':4,1' -ethylene 3.56g (10 mmol) were dissolved in 50ml of toluene under nitrogen protection, and then 0.18g (0.2 mmol) of Pd2dba3, 0.4ml (0.4 mmol) of 1M t-Bu3P and 2.88g (30 mmol) of t-BuONa were added thereto and refluxed for 8 hours, respectively.
After the reaction, the temperature of the reaction product was cooled to room temperature, and then extracted with 200ml of toluene and 200ml of water, a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, and after filtration under reduced pressure, the compound produced by concentrating the organic solvent was subjected to column chromatography using an eluent of Hex: EA =4:1 to obtain intermediate-22.02g (76%).
Intermediate-22 MS (FAB): 397 (M +)
Synthesis of intermediate-23
3.21g (10 mmol) of di ([ 1,1' -ethylene ] -4-yl) amine and 3.59g (10 mmol) of 4-bromo-4 ' -iodo-1,1 ' -ethylene were injected under nitrogen protection, dissolved in 60ml of toluene, and then placed 0.18g (0.2 mmol) of Pd2dba3, 0.4ml (0.4 mmol) of 1Mt-Bu3P0, 88g (30 mmol) of t-BuONa2.88g, respectively, followed by refluxing for 8 hours.
After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with 200ml of toluene and 200ml of water, and then a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, filtered under reduced pressure, and the resulting compound was concentrated in an organic solvent and then subjected to column chromatography using an eluent of Hex: EA =3:1 to obtain intermediate-23.98g (72%).
Intermediate-23 MS (FAB): 552 (M +)
Synthesis of intermediate-24
0.93g (10 mmol) of aniline and 3.56g (10 mmol) of 4-iodo-1,1 '4,1' -terphenyl were injected under nitrogen, dissolved in 50ml of toluene, and then Pd2dba3.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol), and t-BuONA2.88g (30 mmol) were added, followed by refluxing for 8 hours.
After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with 200ml of toluene and 200ml of water, and then a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, filtered under reduced pressure, and the resulting compound was concentrated in an organic solvent and passed through a column chromatography using an eluent of Hex: EA =5:1 to obtain intermediate-24.38g (74%).
Intermediate-24 MS (FAB): 321 (M +)
Synthesis of intermediate-25
0.93g (10 mmol) of aniline and 2.80g (10 mmol) of 4-iodo-1,1' -ethylene were injected under nitrogen protection, and after dissolving in 50ml of toluene, pd2dba3.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol), and t-BuONa2.88g (30 mmol) were added, respectively, followed by refluxing for 8 hours.
After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with 200ml of toluene and 200ml of water, and then a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, filtered under reduced pressure, and the resulting compound was concentrated in an organic solvent and then subjected to column chromatography using an eluent of Hex: EA =5:1 to obtain intermediate-25.99g (81%).
Intermediate-25 MS (FAB): 245 (M +)
Synthesis of intermediate-26
Intermediate-25.45g (10 mmol) and 4-bromo-4 '-iodo-1,1' -ethylene 3.59g (10 mmol) were injected under nitrogen protection, dissolved in toluene 60ml, and then Pd2dba3.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol) and t-BuONA2.88g (30 mmol) were added, followed by refluxing for 8 hours.
After completion of the reaction, the temperature of the reaction product was cooled to room temperature, and then extracted with 200ml of toluene and 200ml of water, a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, filtered under reduced pressure, and the resulting compound obtained by concentrating the organic solvent was subjected to column chromatography using an eluent of Hex: EA =4:1 to obtain intermediate-26.57g (75%).
Intermediate-26 MS (FAB): 476 (M +)
Synthesis of Compound-11
After intermediate-11 g and intermediate-17.9 g were placed in a 250ML three-necked round-bottomed flask, 100ML of toluene and 10ML of ethanol were added, and 47ML of 2M potassium carbonate and 1.08g of Pd (PPh 3) were added to the mixture, and the mixture was refluxed for 12 hours. After confirming that the reaction was completed, the organic layer was extracted, distilled, passed through a column and recrystallized to obtain 8.7g of compound-11.7 in 86% yield.
1H NMR(DMSO,300Hz):δ(ppm)＝8.02-7.91(d,4H),7.65-7.52(d,4H),7.50-7.10(m,6H),7.06-6.94(m,2H),6.75-6.65(d,2H),5.30-5.10(s,4H)
MS(FAB):542(M+)
Synthesis of Compound-25
After intermediate-6 g and intermediate-17.9g were placed in a 250ML three-necked round-bottomed flask, 100ML of toluene and 10ml of ethanol and 47ML of 2M potassium carbonate and 1.08g of Pd (PPh 3) were added thereto, and the mixture was refluxed for 12 hours under heating, it was confirmed that the reaction was completed, and then the organic layer was extracted and distilled, and the compound-25.5g was obtained in a yield of 84% by recrystallization from a column chromatography.
1H NMR(DMSO,300Hz):δ(ppm)＝8.08-7.93(d,4H),7.69-7.54(d,4H),7.52-7.12(m,6H),7.07-6.95(m,2H),6.78-6.66(d,2H),5.30-5.10(s,4H)
MS(FAB):542(M+)
Synthesis of Compound-44
Intermediate-14 g and intermediate-16.8g were added followed by toluene 150ML in a 250ML three-neck round-bottom flask. After refluxing 0.1g of palladium acetate, 0.2g of tri-t-butylphosphine (50% in toluene) and 3.6g of sodium t-butoxide with heating, after confirming that the reaction was completed for 3 hours, the reaction mixture was cooled at room temperature, 150ml of ethyl acetate and 150ml of water were added to extract an organic layer, and the organic layer was subjected to column chromatography and then recrystallized to obtain 44.2g of compound in 81% yield.
1H NMR(DMSO,300Hz):δ(ppm)＝8.09-7.93(d,2H),7.92-7.84(d,2H),7.78-7.54(m,10H),7.52-7.15(m,18H),7.11-6.95(m,2H),6.73-6.61(s,2H),5.30-5.10(s,4H),1.74-1.63(s,12H
MS(FAB):929(M+)
Synthesis of Compound-55
To a 250ML three-necked round-bottomed flask, intermediate-19 g and intermediate-16 g were added, 150mL of toluene was added, and 0.1g of palladium acetate and 0.2g of tri-tert-butylphosphine (50% in toluene) and 2.9g of sodium tert-butoxide were added and then the mixture was refluxed. After completion of the reaction was confirmed after 3 hours, the reaction mixture was cooled at room temperature, 150ml of ethyl acetate and 150ml of water were added to the mixture, and the organic layer was extracted, and the mixture was subjected to column chromatography and recrystallization to obtain 55.7 g of a compound with a yield of 85%.
1H NMR(DMSO,300Hz):δ(ppm)＝8.08-7.93(d,1H),7.91-7.84(m,3H),7.78-7.54(m,6H),7.52-7.12(m,17H),7.08-6.94(m,2H),6.79-6.65(d,2H),5.30-5.10(s,4H),1.73-1.63(s,6H)
MS(FAB):771(M+)
Synthesis of Compound-75
To a 250ML three-necked round-bottomed flask, intermediate-21 g and intermediate-16.6 g were added, and 150ML of toluene was added. 0.1g of palladium acetate and 0.3g of tri-t-butylphosphine (50% in toluene) and 4.7g of t-butanol were added thereto, followed by heating and refluxing. After completion of the reaction was confirmed for 3 hours, the reaction mixture was cooled at room temperature, 150ml of ethyl acetate and 150ml of water were added to the mixture, and the organic layer was extracted, and the mixture was recrystallized after passing through a chromatography column to obtain 75.3g of the compound in 86% yield.
1H NMR(DMSO,300Hz):δ(ppm)＝8.08-7.93(d,1H),7.91-7.84(d,1H),7.78-7.54(m,5H),7.52-7.12(m,9H),7.07-6.95(m,2H),6.78-6.66(d,2H),5.30-5.10(s,4H)2.29-2.18(s,3H),1.72-1.63(s,6H)
MS(FAB):583(M+)
Synthesis of Compound-80
After charging intermediate-20.5g and intermediate-16.5g into a 250ML three-necked round-bottomed flask, 150ML of toluene was charged, 0.1g of palladium acetate and 0.3g of tri-tert-butylphosphine (50% in toluene) were added, and 4.7g of sodium tert-butoxide was heated under reflux, and after 3 hours, it was confirmed that the reaction was completed, the reaction mixture was cooled at room temperature, 150ML of ethyl acetate and 150ML of water were added, and the organic layer was extracted, and the mixture was passed through a column and recrystallized to obtain 80.1g of a compound with a yield of 85%.
1H NMR(DMSO,300Hz):δ(ppm)＝8.08-7.93(d,1H),7.91-7.84(d,1H),7.78-7.54(m,5H),7.52-7.12(m,9H),7.08-6.94(m,2H),6.79-6.65(d,2H),5.30-5.10(s,4H),1.73-1.63(s,6H)
MS(FAB):586(M+)
Synthesis of Compound-265
After charging 6g of intermediate-6 and 13.88g of intermediate-18 into a 250ML three-necked round-bottomed flask, 100ML of toluene, 10ML of ethanol, 47ML of 2M potassium carbonate and 4.08g of Pd (PPh 3) were added thereto, and the mixture was refluxed for 12 hours. After completion of the reaction, the organic layer was distilled off, and the residue was purified by column chromatography and recrystallized to obtain 265.06g of a compound with a yield of 79%.
1H NMR(DMSO,300Hz):δ(ppm)＝7.91-7.84(m,4H),7.78-7.54(m,2H),7.52-7.12(m,16H),7.08-6.94(m,2H),6.79-6.65(d,2H),5.30-5.10(s,4H)
MS(FAB):614(M+)
Synthesis of Compound-286
After adding intermediate-13 g and intermediate-16.10g to a 250ML three-neck round-bottom flask, 150ML of toluene was added. 0.1g of palladium acetate, 0.2g of tri-tert-butylphosphine (50% in toluene), and 3.6g of sodium tert-butoxide were added thereto and the mixture was refluxed. After completion of the reaction was confirmed for 3 hours, the reaction mixture was cooled at room temperature, 150ml of ethyl acetate and 150ml of water were added to extract an organic layer, and the mixture was subjected to column chromatography and recrystallization to obtain 286.1 g of the compound with a yield of 75%.
1H NMR(DMSO,300Hz):δ(ppm)＝8.09-7.93(d,2H),7.92-7.84(d,2H),7.78-7.54(m,10H),7.52-7.15(m,18H),7.10-6.95(m,2H),6.75-6.61(s,2H),1.74-1.63(s,12H)
MS(FAB):957(M+)
Synthesis of Compounds of formula 2
Synthesis of Compound 2-1
Under nitrogen protection, intermediate-23.53g (10 mmol) and intermediate-22.98g (10 mmol) were injected, dissolved in 80ml of toluene, and then added with Pd2dba3 0.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol), t-BuONa2.88g (30 mmol), respectively, followed by refluxing for 8 hours.
After completion of the reaction, the temperature of the reaction product was cooled to room temperature, and after extraction with 250ml of toluene and 250ml of water, a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, and after filtration under reduced pressure, the resulting compound was concentrated in an organic solvent and then subjected to column chromatography using an eluent of Hex: EA =3:1 to obtain 2-1.69g (77%) of the compound.
Compound 2-1 MS (FAB): 869 (M +)
Synthesis of Compounds 2-3
Under nitrogen protection, intermediate-23.53g (10 mmol) and intermediate-24.21g (10 mmol) were injected, and after dissolving in toluene 70ml, pd2dba3 0.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol), and t-BuONa2.88g (30 mmol) were added, respectively, followed by refluxing for 8 hours.
After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with 250ml of toluene and 250ml of water, and then a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, filtered under reduced pressure, and the resulting compound was concentrated in an organic solvent and then subjected to column chromatography using an eluent of Hex: EA =3:1 to obtain 2-3.95g (75%).
Compound 2-3 MS (FAB): 793 (M +)
Synthesis of Compounds 2 to 12
Under the protection of nitrogen, intermediate-26.76g (10 mmol) and intermediate-24.21g (10 mmol) were injected and dissolved in toluene 60ml, and then Pd2dba3 0.18g (0.2 mmol), 1Mt-Bu3P0.4ml (0.4 mmol) and t-BuONa2.88g (30 mmol) were added thereto and refluxed for 8 hours.
After the reaction, the temperature of the reaction product was cooled to room temperature, and after extraction with 200ml of toluene and 200ml of water, a small amount of water in the organic layer was removed with anhydrous magnesium sulfate, and after filtration under reduced pressure, the resulting compound was concentrated in an organic solvent and then subjected to column chromatography using an eluent of Hex: EA =4:1 to obtain 2 to 12.59g (78%) of the compound.
Compound 2-12 MS (FAB) 716 (M +)
The compound of the above general formula 2 can be synthesized by a known method, which is described in the literature.
The present invention will be described in detail below by way of examples and comparative examples. The following examples and comparative examples are only intended to illustrate the present invention, and the scope of the present invention is not limited to the following examples and comparative examples.
Organic electroluminescent device fabrication
Example 1
Adopts ITO as a reflecting layerA polar substrate material, using N in combination 2 Plasma or UV-Ozone surface treatment. Above the anode substrate, HAT-CN was deposited to a thickness of 10nm to the HIL layer, followed by NPD to a thickness of 120nm to the HTL layer. Depositing 25nm AND on the above HTL layer to obtain blue EML; among them, blue EML was doped with 5% of compound 5 of the general formula 1 of the present invention. A 30nm thick ETL layer was deposited over the above anode to prepare a cathode, which layer was obtained by mixing ET-254 and LiQ in a mass ratio of 1:1, followed by continuing to deposit LiQ on the EIL in a thickness of 10 nm. Finally, a 15nm thick mixture of magnesium and silver mixed in a mass ratio of 9:1 was deposited onto the cathode, and further, a 65nm DNTPD was deposited onto the capping layer above the cathode treated by the above method. And bonding a capping cap (seal cap) containing a moisture absorbent with a UV curable adhesive over the capping layer to protect the organic electroluminescent device from oxygen or moisture in the atmosphere, thereby preparing an organic electroluminescent device.
Examples 2 to 51
Examples
The difference from example 1 is that compound 5 in the dock, which is blue EML in example 1, is replaced with compound 11, 19, 25, 31, 33, 35, 44, 55, 65, 75, 80, 82, 85, 95, 100, 105, 109, 111, 113, 115, 119, 120, 124, 134, 140, 145, 149, 151, 153, 156, 158, 160, 165, 180, 195, 199, 214, 234, 245, 265, 286, 297, 302, 308, 310, 315, 319, 344, 347, 352, respectively, and the method of manufacturing the organic electroluminescent device is the same as example 1.
Comparative example 1
The difference from example 1 is that compound 5 of formula 1 in dock as blue EML in example 1, and compound 5 of formula 1 is replaced with 2,5, 8, 11-Tetra-butyl-Perylene (t-Bu-Perylene) in this comparative example, and the method of manufacturing an organic electroluminescent device is identical to example 1.
The compounds used in examples 1 to 51 and comparative example 1 above are as follows.
Examples performance evaluation of the obtained organic electroluminescent device was prepared.
The above embodiments
And comparative example 1 the organic electroluminescent device prepared in this way was tested for its performance at a current density of 10mA/cm 2 The results are shown in Table 1.
TABLE 1
As can be seen from the experimental results shown in Table 1, examples of preparing a light emitting layer using the organic compound of formula 1 as a dopant in the present invention
The organic electroluminescent device obtained by the preparation had improved efficiency and decreased driving voltage as compared with the conventional organic electroluminescent device described in comparative example 1.
Further, as can be seen from the results of T95, the organic electroluminescent device of comparative example 1 had a lifetime of 100 hours or less, whereas the examples had
The lifetime of the organic electroluminescent device obtained by the preparation method is more than 200 hours, particularly, the lifetime of the organic electroluminescent devices of the embodiments 11, 12, 23, 30, 33, 34, 36 and 51 can reach more than 400 hours, so that the problem of limited lifetime of the existing blue material is overcome, and the application of the organic electroluminescent device is further expanded.
Further, examples of preparing a light emitting layer using the organic compound of formula 1 as a dopant in the present invention
The organic electroluminescent device obtained was prepared with a remarkably upward result in terms of efficiency and voltage characteristics as compared with the existing organic electroluminescent device described in comparative example 1.
It can thus be seen that the organic electroluminescent device comprising the organic compound of the present formula 1 as a dopant to prepare a light-emitting layer is excellent in the characteristics of efficiency, voltage and lifetime.
Claims (4)
1. An organic compound whose structure is represented by the following general formula (1):
general formula (1)
In the above formula
R1, R2, R3, R4, R5, R6, R7 and R8 are respectively and independently selected from hydrogen, deuterium, oxygen, F, cl, br, I, CN, si (CH) 3 ) 3 、B(OH) 2 Straight or branched chain alkyl of carbon number 1 to 40, alkoxy of carbon number 1 to 40, thiol of carbon number 1 to 40, or cycloalkyl of carbon number 3 to 40;
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 a linear or branched alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, a thiol having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a phenyl group, a bisphenyl group, a naphthyl group, an anthryl group substituted with a phenyl group, a phenanthryl group, a pyrenyl group, 9,9-dimethylfluorene, carbazole, dibenzofuran, pyrrole, triazole, aminobenzene, pyrazine, pyrimidine, quinoline, or one or more aromatic hydrocarbon groups having 6 to 80 carbon atoms substituted or unsubstituted;
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 straight chain or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thiol of 1 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, bisphenyl, naphthyl, anthryl substituted with phenyl, phenanthryl, pyrenyl, 9,9-dimethylfluorene, spirobi [ fluorone ]]One or more substituted or unsubstituted heteroaromatic hydrocarbon groups having a carbon number of 5 to 90, each of which is selected from the group consisting of carbazole, dibenzofuran, pyrrole, triazole, aminobenzene, pyrazine, pyrimidine and quinoline, and contains one or more elements selected from the group consisting of S, O, N and Si;
F、Cl、Br、I、CN、Si(CH 3 ) 3 、B(OH) 2 one or more substituted or unsubstituted phenyl, bisphenyl, naphthyl, anthryl substituted with phenyl, phenanthryl, pyrenyl, 9,9-dimethylfluorene, carbazole, quinoline, dibenzofuran, pyrrole, triazoles, aminobenzene, pyrazine, pyrimidine and the like selected from the group consisting of straight-chain or branched chain alkyl groups having a carbon number of 1 to 40, alkoxy groups having a carbon number of 1 to 40, thiol having a carbon number of 1 to 40 and cycloalkyl groups having a carbon number of 3 to 40;
z1 and Z2 are respectively independent single combination or double combination;
m1 and M2 are each independently carbon, nitrogen, oxygen or sulfur.
2. The organic compound according to claim 1, wherein,
characterized in that the organic compound is any one of the following compounds 1 to 352:
3. an organic electroluminescent element characterized in that one or more organic thin film layers having at least a light-emitting layer are laminated between a cathode and an anode,
the organic electroluminescent element is characterized in that the light-emitting layer contains one or more organic compounds according to claim 1.
4. An organic electroluminescent element comprising a cathode and an anode, one or more organic thin film layers containing at least a light-emitting layer laminated between the cathode and the anode,
the organic electroluminescent element is characterized in that the organic thin film layer excluding the light-emitting layer contains one or more organic compounds according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20210134530 | 2021-10-11 | ||
| KR10-2021-0134530 | 2021-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115960113A true CN115960113A (en) | 2023-04-14 |
Family
ID=85900106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211230429.0A Pending CN115960113A (en) | 2021-10-11 | 2022-09-30 | Novel organic compound and organic electroluminescent device comprising the same |
Country Status (2)
| Country | Link |
|---|---|
| KR (2) | KR20230052219A (en) |
| CN (1) | CN115960113A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102201028B1 (en) * | 2020-10-23 | 2021-01-11 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
| WO2021034986A1 (en) * | 2019-08-19 | 2021-02-25 | Alphyn Biologics | Croton lechleri compositions for use in treating bleeding, wounds and infections |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101226700B1 (en) | 2009-08-21 | 2013-01-25 | 에스에프씨 주식회사 | Amine derivatives and organoelectroluminescent device employing the same |
| KR102202171B1 (en) | 2012-12-26 | 2021-01-12 | 이데미쓰 고산 가부시키가이샤 | Oxygen-containing fused ring amine compound, sulphur-containing fused ring amine compound, and organic electroluminescent element |
| CN106397110B (en) | 2015-07-31 | 2019-02-19 | 南京高光半导体材料有限公司 | A kind of novel spiro organic compounds |
| CN106397223B (en) | 2015-08-01 | 2019-04-19 | 南京高光半导体材料有限公司 | A kind of organic compound, the organic electroluminescence device material comprising the compound and the organic electroluminescence device comprising the material |
| KR101825612B1 (en) | 2015-10-28 | 2018-02-05 | 난징고광반도체재료유한회사 | Blue fluorescent dopant materials, and organic thin film and organic light emitting devices comprising the same |
-
2022
- 2022-09-26 KR KR1020220122019A patent/KR20230052219A/en unknown
- 2022-09-30 CN CN202211230429.0A patent/CN115960113A/en active Pending
-
2023
- 2023-09-17 KR KR1020230123577A patent/KR20240043689A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021034986A1 (en) * | 2019-08-19 | 2021-02-25 | Alphyn Biologics | Croton lechleri compositions for use in treating bleeding, wounds and infections |
| KR102201028B1 (en) * | 2020-10-23 | 2021-01-11 | 최돈수 | Compound for organic light emitting diode, organic light emitting diode having the same, and display apparatus having organic light emitting diode |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230052219A (en) | 2023-04-19 |
| KR20240043689A (en) | 2024-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI599565B (en) | New compound, organic electroluminescence device material, organic electroluminescence device and electronic device | |
| KR101825612B1 (en) | Blue fluorescent dopant materials, and organic thin film and organic light emitting devices comprising the same | |
| TWI477580B (en) | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same | |
| US7968874B2 (en) | Organic electroluminescent device material and organic electroluminescent device | |
| WO2019098234A1 (en) | Organic electroluminescent element | |
| JP2014123687A (en) | Organic electroluminescent element and electronic device | |
| JP6158703B2 (en) | COMPOUND HAVING ACRYDAN RING STRUCTURE AND ORGANIC ELECTROLUMINESCENT DEVICE | |
| KR101468493B1 (en) | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same | |
| KR20140145428A (en) | Compound for organic electroluminescent device and organic electroluminescent device comprising the same | |
| JP2013063930A (en) | Aromatic amine derivative, and organic electroluminescent element using the same | |
| KR20140018101A (en) | Compound for organic electroluminescent device and organic electroluminescent device including the same | |
| JP5830097B2 (en) | Novel compounds for organic electronic materials and organic electroluminescent devices using the same | |
| KR101555155B1 (en) | Novel spyrobifluorene type organic compounds and an organic electroluminescent device comprising the same | |
| TW201313681A (en) | Aromatic amine derivative and organic electroluminescent element using same | |
| CN107925008A (en) | Organic electroluminescence device | |
| US20210053954A1 (en) | Aromatic amine compound, covering layer material, and light-emitting element | |
| KR101609020B1 (en) | New compounds and organic electro luminescence device comprising the same | |
| US9755161B2 (en) | Organic light emitting display device | |
| KR20130069431A (en) | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same | |
| TW202140748A (en) | Organic electroluminescent device | |
| WO2014034893A1 (en) | Organic electroluminescent element | |
| CN115611835B (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR20150022461A (en) | Compound for organic electroluminescent device and organic electroluminescent device comprising the same | |
| WO2012114746A1 (en) | Compound containing substituted o-terphenyl structure, and organic electroluminescent element | |
| JP2015233024A (en) | Organic electroluminescent device |
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 |