CN110734448A - Organic compound, application thereof and organic electroluminescent device - Google Patents
Organic compound, application thereof and organic electroluminescent device Download PDFInfo
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- CN110734448A CN110734448A CN201910478531.4A CN201910478531A CN110734448A CN 110734448 A CN110734448 A CN 110734448A CN 201910478531 A CN201910478531 A CN 201910478531A CN 110734448 A CN110734448 A CN 110734448A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 239000000463 material Substances 0.000 claims abstract description 36
- -1 dibenzofuranyl Chemical group 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 description 139
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 96
- 238000006243 chemical reaction Methods 0.000 description 88
- 239000010410 layer Substances 0.000 description 74
- 238000003756 stirring Methods 0.000 description 73
- 230000015572 biosynthetic process Effects 0.000 description 64
- 238000003786 synthesis reaction Methods 0.000 description 64
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
- 238000004440 column chromatography Methods 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 238000010438 heat treatment Methods 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 48
- 238000001035 drying Methods 0.000 description 47
- 238000010992 reflux Methods 0.000 description 45
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 42
- 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 42
- 239000000243 solution Substances 0.000 description 38
- 239000002994 raw material Substances 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 35
- 239000012295 chemical reaction liquid Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 238000001819 mass spectrum Methods 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 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 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 18
- 239000007818 Grignard reagent Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- 150000004795 grignard reagents Chemical class 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 230000002194 synthesizing effect Effects 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 238000001308 synthesis method Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- ULKSWZAXQDJMJT-UHFFFAOYSA-M magnesium;2,2,6,6-tetramethylpiperidin-1-ide;chloride Chemical compound [Cl-].CC1(C)CCCC(C)(C)N1[Mg+] ULKSWZAXQDJMJT-UHFFFAOYSA-M 0.000 description 6
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 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 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 4
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000005049 silicon tetrachloride Substances 0.000 description 4
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 2
- LCLMNWMVIYGMNE-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)oxyboronic acid Chemical compound OB(O)Oc1ccc2n(-c3ccccc3)c3ccccc3c2c1 LCLMNWMVIYGMNE-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- MVAOYMNWVVRUPL-UHFFFAOYSA-N 11,11-dimethyl-5h-indeno[1,2-b]carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=C1C3=CC=CC=C3C(C)(C)C1=C2 MVAOYMNWVVRUPL-UHFFFAOYSA-N 0.000 description 2
- UJORPFQWUKFXIE-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 UJORPFQWUKFXIE-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- IMLDYQBWZHPGJA-UHFFFAOYSA-N 2-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3NC2=C1 IMLDYQBWZHPGJA-UHFFFAOYSA-N 0.000 description 2
- OADZHFGJIVKDJN-UHFFFAOYSA-N 3-bromo-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC=C(Br)C=C3C=CC2=C1 OADZHFGJIVKDJN-UHFFFAOYSA-N 0.000 description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 2
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 2
- NPHLAWPEXYBGTP-UHFFFAOYSA-N 5h-[1]benzothiolo[3,2-c]carbazole Chemical compound C1=CC=C2SC3=C4C5=CC=CC=C5NC4=CC=C3C2=C1 NPHLAWPEXYBGTP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 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
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
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- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 150000005041 phenanthrolines Chemical class 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
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- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
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- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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- 238000005406 washing Methods 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
Classifications
-
- 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
- C07D491/12—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 three hetero rings
- C07D491/20—Spiro-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
- C07D495/12—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 three hetero rings
- C07D495/20—Spiro-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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- 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
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Abstract
The invention relates to the field of organic electroluminescent devices, and discloses an organic compound, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I) or a formula (II). The organic compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of the organic electroluminescent material, and simultaneously can enable the organic electroluminescent material containing the organic compound to have better performance than that of the organic electroluminescent materialHigh hole mobility and electron mobility, thereby improving luminous efficiency.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to organic compounds, application of the organic compounds in organic electroluminescent devices, and organic electroluminescent devices containing or more than two compounds in the organic compounds.
Background
Compared with the traditional liquid crystal technology, the organic electroluminescence (OLED) technology does not need backlight illumination and color filters, pixels can emit light to be displayed on a color display panel, and the OLED technology has the characteristics of ultrahigh contrast, ultrahigh visual angle, curved surface, thinness and the like.
The properties of OLEDs are not only influenced by the emitter, but in particular the materials forming the individual layers of the OLED have a very important influence on the properties of the OLED, for example substrate materials, hole-blocking materials, electron-transport materials, hole-transport materials and electron-or exciton-blocking materials, light-emitting materials, etc.
At present, the OLED device or panel still has the defects of high driving voltage, short service life, low current efficiency and low brightness, in order to improve the defects, the device structure needs to be further optimized by step in aspect, and in addition, the performance of each functional layer and luminescent material needs to be improved in aspect, wherein the green organic electroluminescent host material greatly affects the efficiency and the service life of the green device, so the development of the novel green host material has very important significance.
Disclosure of Invention
The invention aims to overcome the defects of low luminous efficiency and short service life of a green organic electroluminescent device in the prior art, and provides novel organic compounds which have better thermodynamic stability, good film-forming property and proper triplet state energy level when being used as a green organic electroluminescent main body material, and can obviously improve the luminous efficiency of the device and prolong the service life of the device.
In order to achieve the above object, the th aspect of the present invention provides kinds of organic compounds having a structure represented by formula (I) or formula (II),
wherein, in the formula (I) and the formula (II),
x is O or S, and X is O or S,
z is C or Si, and Z is C or Si,
R11and R12Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing arylheterocyclic group, substituted phenyl group, and substituted or unsubstituted diphenylamine group;
R21and R22Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing aryltricyclic group, substituted or unsubstituted nitrogen-containing arylpentacyclic group, substituted phenyl group, substituted or unsubstituted dianilino group, and
R11、R12、R21and R22Each substituent on is independently selected from C1-3At least of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl groups of (a).
A second aspect of the present invention provides the use of an organic compound as described in the preceding aspect in an organic electroluminescent device.
The third aspect of the present invention provides kinds of organic electroluminescent devices containing or two or more kinds of the organic compounds described in the aforementioned aspect of the present invention.
The organic compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of the organic electroluminescent material, and simultaneously, the organic electroluminescent material containing the organic compound has higher and balanced hole mobility and electron mobility, so that the exciton recombination rate is improved, and the high luminous efficiency of a device is realized.
When the organic compound provided by the invention is used in an organic light-emitting device, the organic compound is used as a green phosphorescent main body material, so that the working voltage of the device can be remarkably reduced, the photoelectric property of the device is improved, the efficiency advantage of the phosphorescent material can be more effectively exerted, and the device has a longer service life.
Detailed Description
For numerical ranges, between the endpoints of each range and the individual points, and between the individual points may be combined with each other to yield new numerical ranges or ranges, which should be considered as specifically disclosed herein.
As previously mentioned, the th aspect of the invention provides organic compounds having a structure represented by formula (I) or formula (II),
wherein, in the formula (I) and the formula (II),
x is O or S, and X is O or S,
z is C or Si, and Z is C or Si,
R11and R12Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing arylheterocyclic group, substituted phenyl group, and substituted or unsubstituted diphenylamine group;
R21and R22Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing aryltricyclic group, substituted or unsubstituted nitrogen-containing arylpentacyclic group, substituted phenyl group, substituted or unsubstituted dianilino group, and
R11、R12、R21and R22Each substituent on is independently selected from C1-3Alkyl, phenyl, biphenyl, or a salt thereof,At least of dibenzofuranyl, dibenzothienyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl groups.
In the present invention, "C1-3The "alkyl group of (1)" includes methyl, ethyl, n-propyl and isopropyl groups.
Preferably, in the formula (I) and the formula (II),
the nitrogen-containing aromatic heterocyclic tricyclic in the substituted or unsubstituted nitrogen-containing aromatic heterocyclic tricyclic is a tricyclic shown in a formula (I1) or a formula (I2), and any position in the tricyclic shown in the formula (I1) and the formula (I2) which can be connected in a bonding mode is connected with the mother nucleus in the formula (I) and the formula (II) through a C-C bond or a C-N bond;
wherein Y in formula (I2) is O, S, C or N atom;
and the C atom and/or the N atom in the tricyclic ring represented by the formula (I1) and the formula (I2) are optionally substituted by a group selected from C1-3At least groups of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl of (a);
according to preferred embodiments, the nitrogen-containing aromatic tricyclic ring of the substituted or unsubstituted nitrogen-containing aromatic tricyclic ring is a tricyclic ring of formula (I2), and the N atom in the tricyclic ring of formula (I2) is linked to the parent nucleus of formula (I) and formula (II) via a C-N bond;
wherein Y in formula (I2) is O, S, C or N atom;
and the C atom and/or the N atom in the tricyclic ring of formula (I2) is optionally substituted by a group selected from C1-3At least of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl.
Preferably, in formula (I) and formula (II),
the nitrogen-containing aromatic pentacyclic ring in the substituted or unsubstituted nitrogen-containing aromatic pentacyclic ring is selected from pentacyclic rings shown in formulas (II1) to (II6),
wherein X in the formulae (II1) to (II6)1、X2、X3、X4、X5And X6Each independently selected from O, S, C and an N atom;
and the C atom and/or the N atom in the pentacyclic ring shown in the formulas (II1) to (II6) are optionally selected from C1-3At least groups of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl of (a);
preferably, in the formula (I) and the formula (II), the substituted or unsubstituted diphenylamine group is represented by the formula (III),
R31and R32Is selected from H, C1-3At least groups selected from alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl and carbazolyl.
According to preferred embodiments, the structures represented by formula (I) or formula (II) are at least of the following structures, and R in the following structures11、R12、R21And R22Are as defined in relation to the previous invention:
according to another preferred embodiments, the compound having the structure shown in formula (I) or formula (II) is selected from any of the specific compounds listed in claim 5 of the present invention.
According to still another preferred embodiments, the compound having the structure shown in formula (I) or formula (II) is selected from any of the specific compounds listed in claim 6 of the present invention.
When the specific compounds recited in claims 5 and 6 of the present invention are used as green organic electroluminescent host materials, the luminous efficiency of the device can be improved more remarkably, and the service life of the device can be prolonged.
As mentioned above, the second aspect of the present invention provides the use of the organic compound described in the aspect of the present invention in an organic electroluminescent device.
As described above, the third aspect of the present invention provides organic electroluminescent devices containing or more compounds among the organic compounds described in the aspect of the present invention.
Preferably, the organic compound is present in at least layers among an electron transport layer, a light emitting layer, and a hole blocking layer of the organic electroluminescent device.
More preferably, the organic compound is present in a light emitting layer of the organic electroluminescent device. Particularly preferably, the organic compound is used as a host material in the light-emitting layer.
According to preferred embodiments, the organic electroluminescent device includes a substrate, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an optional electron blocking layer, an emission layer (EML), an optional hole blocking layer, an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode, which are sequentially stacked.
Preferably, the organic electroluminescent device further comprises an th covering layer and/or a second covering layer, wherein the th covering layer is arranged on the outer surface of the anode, and the second covering layer is arranged on the outer surface of the cathode.
For example, the organic electroluminescent device may be sequentially stacked with an th capping layer, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an emission layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a cathode, and a second capping layer.
Preferably, the th capping layer and the second capping layer each independently contain an organic compound according to of the present invention.
The substrate of the present invention may use a glass substrate, a plastic substrate, or a metal substrate.
Preferably, the anode material forming the anode is or more selected from indium tin oxide, indium zinc oxide and tin dioxide, wherein the thickness of the anode active layer formed by the anode material can be 100-1700 angstroms, for example.
Preferably, the material forming the hole injection layer is a hole injection material, and the material forming the hole transport layer is a hole transport material, and the hole injection material and hole transport material are selected from aromatic amine derivatives (e.g. NPB, SqMA1), hexaazatriphenylene derivatives (e.g. HACTN), indolocarbazole derivatives, conductive polymers (e.g. PEDOT/PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorenamine, spirobifluorenylamine.
The Hole Injection Layer (HIL) and the Hole Transport Layer (HTL) can be formed, for example, using an aromatic amine derivative of the following general formula:
the groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
Preferably, the hole injection layer has a thickness of 100-2000 angstroms, more preferably 200-600 angstroms.
Preferably, the hole transport layer has a thickness of 100-1000 angstroms, more preferably 200-400 angstroms.
Preferably, the material forming the electron transport layer can also be at least species selected from the group consisting of metal complexes, benzimidazole derivatives, pyrimidine derivatives, pyridine derivatives, quinoline derivatives, and quinoxaline derivatives.
The material for forming the electron blocking layer is not particularly limited, and compounds capable of satisfying the following conditions 1 and/or 2 can be considered to be used in the case of :
1, the method comprises the following steps: the luminescent layer has a higher LUMO energy level, and the purpose of the luminescent layer is to reduce the number of electrons leaving the luminescent layer, so that the recombination probability of the electrons and holes in the luminescent layer is improved.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
Materials forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (e.g., NPB), spirobifluorene amines (e.g., SpMA2), in which the structures of a portion of the electron blocking material and the hole injecting material and the hole transporting material are similar. The electron blocking layer preferably has a thickness of 50 to 600 angstroms.
The material forming the hole blocking layer is preferably a compound having the following conditions 1 and/or 2:
1, the method comprises the following steps: the organic electroluminescent device has a higher HOMO energy level, and the purpose of the organic electroluminescent device is to reduce the number of holes leaving a light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is improved.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
The material forming the hole blocking layer may further contain, for example, phenanthroline derivatives (e.g., Bphen, BCP), triphenylene derivatives, benzimidazole derivatives. Preferably, the hole blocking layer has a thickness of 50 to 600 angstroms.
Preferably, the material of the electron injection layer is LiF, CsF, CsCO3 in LiQ, etc. preferably, the electron injection layer has a thickness of 1-50 angstroms.
Preferably, the cathode material is or more of Al, Mg and Ag preferably, the thickness of the cathode layer is 800-1500 angstroms.
The organic electroluminescent device of the invention is preferably coated with layers or a plurality of layers by means of a sublimation process, in this case in a vacuum sublimation system at less than 10-3Pa, preferably less than 10-4The compound provided by the present invention is applied by vapor deposition at an initial pressure of Pa.
The organic electroluminescent device according to the invention is preferably coated with layers or a plurality of layers by means of an organic vapour deposition method or sublimation with the aid of a carrier gas in this case at 10-6The material is applied under a pressure of Pa to 100 Pa. A particular example of such a process is an organic vapor deposition jet printing process, wherein the compounds provided by the present invention are applied directly through a nozzle and form a device structure.
The organic electroluminescent device of the present invention is preferably formed into layers or a multilayer structure by photo-induced thermal imaging or thermal transfer.
The organic electroluminescent device of the present invention preferably comprises layers or a multi-layer structure prepared by spin coating or by any printing means, such as screen printing, flexographic printing, ink jet printing, lithographic printing, more preferably ink jet printing, but when multiple layers are prepared by this method, layer-to-layer damage is likely to occur, i.e. when layers are prepared and then additional layers are prepared from the solution, the solvent in the solution will destroy the already formed layers, which is detrimental to device preparation.
Preferably, the organic electroluminescent device of the present invention is manufactured by applying or more layers from a solution and or more layers by a sublimation method.
Preferred solvents for the preparation of organic electroluminescent devices according to the invention are selected from the group consisting of toluene, anisole, o-xylene, m-xylene, p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, phenoxytoluene, in particular 3-phenoxytoluene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, benzothiazole, butyl benzoate, isopropanol, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, cyclohexanol, Methyl benzoate, NMP, p-methylisobenzene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, 2-heptanol, 3-heptanol, or a mixture of these solvents.
Preferably, in preparing the organic electroluminescent device of the present invention, the compound of the present invention and the other compounds are thoroughly mixed and then applied as described above to form layers or more-3Pa, preferably less than 10-4Each compound was applied by vapor deposition at an initial pressure of Pa to form layers or multiple layers.
The technical solution of the present invention is described in detail by specific examples below.
The various starting materials used are all commercially available, unless otherwise specified.
Preparation example 1: compound 1-1
Synthesis of intermediate 1-1-1-1: dissolving 0.1mol of 2-bromo-o-phenanthroline and 0.3mol of KOH in 1500ml of water, refluxing for 1h, and gradually dropwise adding 0.03mol of KMnO41L of hot saturated aqueous solution. The reaction solution is refluxed for 2 hours and reactedAfter completion, the mixture was filtered while it was hot, the filtrate was cooled to room temperature, a large number of needle crystals were precipitated, the filtrate was filtered, the filtrate was extracted with chloroform 3 times, the organic phases were combined, the solution was yellow and transparent, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain a yellow solid, whereby intermediate 1-1-1 was obtained (yield: 50%).
Synthesis of intermediate 1-1-1-2: 0.05mol of the intermediate 1-1-1-1 is added into 200ml of o-dichlorobenzene to be stirred and dissolved completely, and then added into 0.5mol of methane sulfonic acid dropwise and stirred for 1 hour at room temperature. And dropwise adding an o-dichlorobenzene solution containing 0.25mol of phenol, keeping the temperature at 35 ℃ for 2h, heating to 150 ℃, reacting for 24h, detecting that the raw materials are completely reacted, concentrating and rotationally steaming the reaction liquid, and performing column chromatography to obtain an intermediate 1-1-1-2 (the yield is 41%).
Synthesis of Compound 1-1-1: dissolving 0.0205mol of intermediate 1-1-1-2 in 80ml of toluene solvent, sequentially adding 0.0205mol of carbazole, 0.051mol of sodium tert-butoxide, 0.0002mol of tri-tert-butylphosphine and 0.0002mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 6 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-1 (yield is 58%).
Mass spectrum: C35H21N3O, theoretical value: 499.17, found: 499.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.05-7.08 (2H, m), 7.17-7.33 (9H, m), 7.48-7.55 (4H, m), 7.63-7.68 (1H, m), 7.94-7.95 (1H, m), 8.11-8.12 (1H, m), 8.51-8.55 (2H, m).
Preparation example 2: compound 1-1-2
Synthesis of Compounds 1-1-2: synthesis method the synthesis of Compound 1-1-1 was performed (yield 61%).
Mass spectrum: C41H25N3O, theoretical value: 575.20, found: 575.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.05-7.06 (2H, m), 7.21-7.52 (16H, m), 7.62-7.63 (1H, m), 7.79-7.80 (1H, m), 7.94-7.95 (1H, m), 7.18-7.19 (1H, m), 8.51-8.55 (2H, m).
Preparation example 3: compounds 1-1-4
Synthesis of intermediate 1-1-4-1: dissolving 0.1mol of iodobenzene in 200ml of toluene solvent, sequentially adding 0.1mol of 1-bromocarbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting that the reaction of the raw materials is finished after 6 hours, decompressing and spin-drying the reaction liquid, and obtaining an intermediate 1-1-4-1 (yield 65%) by column chromatography.
Synthesis of intermediate 1-1-4-2: dissolving 0.065mol of intermediate 1-1-4-1 in 200ml of dioxane solvent, sequentially adding 0.065mol of diboron pinacol ester, 0.163mol of potassium acetate and 0.00065mol of 1, 1' -bis (diphenylphosphine) ferrocene palladium dichloride under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and obtaining the intermediate 1-1-4-2 (the yield is 80%) by column chromatography.
Synthesis of Compounds 1-1-4: dissolving 0.052mol of the intermediate 1-1-4-2 in 200ml of dioxane solvent, sequentially adding 0.052mol of diboron pinacol ester, 0.13mol of potassium acetate and 0.00052mol of 1, 1' -bis (diphenylphosphine) ferrocene palladium dichloride under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography to obtain the compound 1-1-4 (the yield is 78%).
Mass spectrum: C41H25N3O, theoretical value: 575.20, found: 575.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.05-7.06 (2H, m), 7.19-7.34 (9H, m), 7.48-7.63 (9H, m), 8.12-8.13 (1H, m), 8.51-8.57 (2H, m), 9.00-9.01 (1H, m).
Preparation example 4: compounds 1-1-5
Synthesis of intermediate 1-1-5-1: the synthesis method is the same as that of the intermediate 1-1-4-1 (yield is 78%).
Synthesis of intermediate 1-1-5-2: the synthesis method is the same as that of the intermediate 1-1-4-2 (yield 72%).
Synthesis of Compounds 1-1-5: synthesis method the synthesis of Compound 1-1-4 was performed (yield 68%).
Mass spectrum: C47H29N3O, theoretical value: 651.23, found: 651.23. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.29 (8H, m), 7.41-7.52 (7H, m), 7.62-7.68 (4H, m), 7.79-7.80 (2H, m), 8.03-8.04 (1H, m), 8.12-8.13 (1H, m), 8.28-8.29 (1H, m), 8.51-8.52 (1H, m), 8.69-8.70 (1H, m).
Preparation example 5: compounds 1-1-8
Synthesis of Compounds 1-1-8: synthesis method the synthesis of Compound 1-1-4 was performed (yield 72%).
Mass spectrum: C41H25N3O, theoretical value: 575.20, found: 575.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (10H, m), 7.48-7.63 (6H, m), 7.94-7.95 (1H, m), 8.12-8.13 (1H, m), 8.30-8.31 (1H, m), 8.51-8.60 (3H, m).
Preparation example 6: compounds 1-1-10
Intermediate 1-1-10-1: dissolving 0.10mol of 9-phenyl-9H-carbazole-3-yl boric acid in 300ml of dioxane solvent, sequentially adding 0.10mol of 3-bromocarbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain an intermediate 1-1-10-1 (yield is 80%).
Synthesis of Compounds 1-1-10: synthesis method the synthesis of Compound 1-1-1 (yield 72%) was followed.
Mass spectrum: C53H32N4O, theoretical value: 740.26, found: 740.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (9H, m), 7.48-7.63 (11H, m), 7.77-7.78 (2H, m), 7.87-8.00 (3H, m), 8.12-8.18 (2H, m), 8.51-8.55 (2H, m).
Preparation example 7: compounds 1-1-12
Synthesis of Compounds 1-1-12: dissolving 0.10mol of intermediate 1-1-1-2 in 400ml of toluene solvent, sequentially adding 0.10mol of 9, 10-dihydro-9, 9-dimethylacridine, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 6h, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-12 (the yield is 52%).
Mass spectrum: C38H27N3O, theoretical value: 541.22, found: 541.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 6.35-6.36 (1H, m), 6.54-6.55 (2H, m), 6.73-6.81 (3H, m), 7.02-7.05 (6H, m), 7.17-7.22 (7H, m), 7.48-7.49 (1H, m), 8.51-8.52 (1H, m).
Preparation example 8: compounds 1-1-14
Synthesis of Compounds 1-1-14: dissolving 0.10mol of intermediate 1-1-1-2 in 400ml of toluene solvent, sequentially adding 0.10mol of 11-phenyl-11, 12-indolino [2,3-a ] carbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5 hours, carrying out reduced pressure spin drying on reaction liquid, and obtaining the compound 1-1-14 (yield is 55%) by column chromatography.
Mass spectrum: C47H28N4O, theoretical value: 664.23, found: 664.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (10H, m), 7.48-7.58 (9H, m), 7.94-7.95 (2H, m), 8.12-8.13 (1H, m), 8.51-8.55 (3H, m).
Preparation example 9: compounds 1-1-16
Synthesis of Compounds 1-1-16: dissolving 0.10mol of intermediate 1-1-1-2 in 400ml of toluene solvent, sequentially adding 0.10mol of 8H- [1] benzothieno [2,3-c ] carbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-16 (yield is 55%).
Mass spectrum: C41H23N3OS, theoretical value: 605.16, found: 605.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (9H, m), 7.48-7.55 (5H, m), 7.94-7.98 (3H, m), 8.51-8.55 (3H, m).
Preparation example 10: compounds 1-1-20
Synthesis of Compounds 1-1-20: dissolving 0.10mol of intermediate 1-1-1-2 in 400ml of toluene solvent, sequentially adding 0.10mol of 5, 7-dihydro-7, 7-dimethyl-indeno [2,1-b ] carbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5h, carrying out reduced pressure spin drying on reaction liquid, and obtaining the compound 1-1-20 (yield is 58%) by column chromatography.
Mass spectrum: C44H29N3O, theoretical value: 615.23, found: 615.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 6.80-6.81 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (10H, m), 7.44-7.61 (5H, m), 7.69-7.70 (1H, m), 7.94-7.95 (1H, m), 8.09-8.10 (1H, m), 8.51-8.55 (2H, m).
Preparation example 11: compounds 1-1-25
Synthesis of intermediate 1-1-25-1: the synthesis method is the same as that of the intermediate 1-1-1-1 (yield 57%).
Synthesis of intermediates 1-1-25-2: the synthesis method is the same as that of the intermediate 1-1-1-2 (yield 43%).
Synthesis of Compounds 1-1-25: the synthesis method is the same as that of the intermediate 1-1-4 (yield 54%).
Mass spectrum: C47H29N3O, theoretical value: 651.23, found: 651.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.05-7.06 (2H, m), 7.17-7.29 (7H, m), 7.41-7.52 (10H, m), 7.63-7.64 (1H, m), 7.77-7.82 (2H, d), 8.01-8.02 (1H, m), 8.09-8.18 (3H, m), 8.51-8.52 (1H, m), 8.80-8.80 (1H, s).
Preparation example 12: compound 1-1-29
Synthesis of Compounds 1-1-29: dissolving 0.10mol of intermediate 1-1-25-2 in 400ml of toluene solvent, sequentially adding 0.10mol of dibenzo-1, 4-thiazine, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5h, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-29 (yield is 61%).
Mass spectrum: C35H21N3OS, theoretical value: 531.14, found: 531.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 6.97-7.22 (17H, m), 7.48-7.49 (1H, m), 7.63-7.64 (1H, m), 8.51-8.52 (1H, m).
Preparation example 13: compounds 1-1-36
Synthesis of Compounds 1-1-36: dissolving 0.10mol of intermediate 1-1-25-2 in 400ml of toluene solvent, sequentially adding 0.10mol of 5H- [1] benzothieno [3,2-c ] carbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-36 (yield is 65%).
Mass spectrum: C41H23N3OS, theoretical value: 605.16, found: 605.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.05-7.06 (2H, m), 7.19-7.33 (9H, m), 7.48-7.52 (3H, m), 7.94-8.05 (3H, m), 8.12-8.13 (1H, m), 8.34-8.35 (1H, d), 8.45-8.55 (3H, m).
Preparation example 14: compounds 1-1-44
Synthesis of intermediate 1-1-44-1: adding 0.1mol of 2-bromo-17-phenanthroline and 0.35mol of KOH into 1.3L of water, stirring and heating to reflux reaction, and dropwise adding 0.3mol of KMNO4 into a hot solution in water (1L) after about 1 h. The mixture was refluxed for an additional 2h and then filtered hot. The filtrate was cooled, extracted with chloroform three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried under reduced pressure to obtain intermediate 1-1-44-1 (yield 60%) by column chromatography.
Synthesis of intermediates 1-1-44-2: dissolving 0.06mol of intermediate 1-1-44-1 in 40ml of o-dichlorobenzene, dropwise adding the mixture into 30ml of methane sulfonic acid, stirring the mixture at 35 ℃ for 30min, then adding 0.3mol of phenol, stirring the mixture, heating the mixture to 80 ℃, detecting that the reaction of the raw materials is finished after 4h, carrying out reduced pressure spin drying on the reaction liquid, and carrying out column chromatography to obtain the intermediate 1-1-44-2 (the yield is 50%).
Synthesis of Compounds 1-1-44: adding 130ml of dioxane solvent and 10ml of water into a three-neck flask, sequentially adding 0.03mol of intermediate 1-1-44-2, 0.03mol of 4-boric acid-9 phenyl carbazole, 0.075mol of sodium tert-butoxide, 0.0003mol of tri-tert-butylphosphine and 0.0003mol of tris (dibenzylideneacetone) dipalladium, stirring, heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-44 (the yield is 70%).
Mass spectrum: C41H25N3O, theoretical value: 575.20, found: 575.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.04-7.05 (2H, m), 7.19-7.34 (10H, m), 7.45-7.63 (7H, m), 7.84-7.86 (1H, m), 8.12-8.15 (1H, m), 8.40-8.45 (2H, m), 8.57-8.59 (1H, m), 9.00-9.01 (1H, m).
Preparation example 15: compounds 1-1-48
Synthesis of intermediate 1-1-48-1: adding 0.1mol of 3-bromo-1, 7-phenanthroline and 0.35mol of KOH into 1.3L of water, stirring and heating to reflux reaction, and dropwise adding 0.3mol of KMNO4 into a hot solution in water (1L) after about 1 h. The mixture was refluxed for an additional 2h and then filtered hot. The filtrate was cooled, extracted with chloroform three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried under reduced pressure to give intermediate 1-1-48-1 (yield 60%) by column chromatography.
Synthesis of intermediates 1-1-48-2: dissolving 0.06mol of intermediate 1-1-48-1 in 40ml of o-dichlorobenzene, dropwise adding the mixture into 30ml of methane sulfonic acid, stirring the mixture at 35 ℃ for 30min, then adding 0.3mol of phenol, stirring the mixture, heating the mixture to 80 ℃, detecting that the reaction of the raw materials is finished after 4h, carrying out reduced pressure spin drying on the reaction liquid, and carrying out column chromatography to obtain the intermediate 1-1-48-2 (the yield is 50%).
Synthesis of Compounds 1-1-48: adding 130ml of dioxane solvent and 10ml of water into a three-neck flask, sequentially adding 0.03mol of intermediate 1-1-48-2, 0.03mol of 9, 10-dihydro-9, 9-dimethylacridine, 0.075mol of sodium tert-butoxide, 0.0003mol of tri-tert-butylphosphine and 0.0003mol of tris (dibenzylideneacetone) dipalladium, stirring, heating to reflux, detecting the completion of the reaction of the raw materials after 4h, performing reduced pressure spin drying on the reaction liquid, and performing column chromatography to obtain the compound 1-1-48 (yield 70%).
Mass spectrum: C38H27N3O, theoretical value: 541.22, found: 541.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 6.55-6.56 (2H, m), 6.73-6.75 (2H, m), 7.02-7.05 (6H, m), 7.19-7.29 (8H, m), 7.69-7.72 (1H, m), 8.40-8.45 (2H, m).
Preparation example 16: compound 1-1-56
Synthesis of Compounds 1-1-56: adding 130ml of dioxane solvent and 10ml of water into a three-neck flask, sequentially adding 0.01mol of intermediate 1-1-48-2 and 0.01mol of 11, 11-dimethyl-5, 11-dihydroindeno [1,2-b ] carbazole, 0.025mol of sodium tert-butoxide, 0.0001mol of tri-tert-butylphosphine and 0.0001mol of tris (dibenzylideneacetone) dipalladium, stirring and heating to reflux, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-1-48 (yield is 70%).
Mass spectrum: C44H29N3O, theoretical value: 615.23, found: 615.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 7.05-7.06 (2H, m), 7.19-7.33 (10H, m), 7.44-7.45 (1H, m), 7.54-7.54 (1H, s), 7.60-7.61 (3H, m), 7.94-7.95 (1H, m), 8.09-8.12 (2H, m), 8.27-8.28 (1H, m), 8.40-8.45 (2H, m), 8.55-8.56 (1H, m).
Preparation example 17: compound 1-2-1
And (3) synthesizing an intermediate 1-2-1-1: dissolving 0.1mol of 2-bromobenzothiol in 200ml of toluene solvent, sequentially adding 0.1mol of iodobenzene, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting the completion of the reaction of the raw materials after 4h, decompressing and spin-drying the reaction liquid, and obtaining an intermediate 1-2-1-1 (yield 90%) by column chromatography.
And (3) synthesizing an intermediate 1-2-1-2: adding 0.1mol of 3-bromo-1, 10-phenanthroline and 0.35mol of KOH into 1.3L of water, stirring and heating to reflux reaction, and dropwise adding 0.3mol of KMNO4 into a hot solution in water (1L) after about 1 h. The mixture was refluxed for an additional 2h and then filtered hot. The filtrate was cooled, extracted with chloroform three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried under reduced pressure to obtain intermediate 1-2-1-2 (yield 50%) by column chromatography.
Synthesis of intermediate 1-2-1-3: a solution of 0.05mol of intermediate 1-2-1-3 in 20ml of o-dichlorobenzene was added dropwise to 5ml of trifluoromethanesulfonic acid as a ketone solution. Adding 0.06mol of intermediate 1-2-1-1 into 130ml of anhydrous THF, stirring, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 0.06mol of 2.5mol/L n-butyllithium, keeping the temperature for 1 hour at-78 ℃, heating to room temperature, keeping for 2 hours, cooling to-78 ℃, adding the prepared ketone solution, heating to room temperature, adding water for quenching and filtering after 3 hours, extracting the filtrate for three times by using chloroform, drying by using anhydrous sodium sulfate, filtering, performing reduced pressure spin drying on the filtrate, and performing column chromatography to obtain intermediate 1-2-1-3 (the yield is 40%).
Synthesis of Compound 1-2-1: dissolving 0.02mol of intermediate 1-2-28-2 in 100ml of toluene solvent, sequentially adding 0.02mol of 2-phenyl-9H-carbazole, 0.05mol of sodium tert-butoxide, 0.0002mol of tri-tert-butylphosphine and 0.0002mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 1-2-1 (yield is 75%).
Mass spectrum: C41H25N3S, theoretical value: 591.18, found: 591.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.03-7.07 (4H, m), 7.21-7.65 (16H, m), 8.10-8.12 (2H, m), 8.49-8.51 (2H, m).
Preparation example 18: compounds 1-2-15
Synthesis of Compounds 1-2-15: the synthesis method was the same as the synthesis of compound 1-1-36 to give compound 1-2-15 (yield 66%). Mass spectrum: C41H23N3S2, theoretical value: 621.13, found: 621.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 6.81-6.82 (1H, m), 7.03-7.07 (4H, m), 7.25-7.33 (5H, m), 7.48-7.55 (5H, m), 7.65-7.66 (2H, m), 7.94-8.05 (3H, m), 8.45-8.55 (3H, m).
Preparation example 19: compounds 1-2-28
Synthesis of intermediate 1-2-28-1: dissolving 0.1mol of 2-bromobenzothiol in 200ml of toluene solvent, sequentially adding 0.1mol of iodobenzene, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting the completion of the reaction of the raw materials after 4h, decompressing and spin-drying the reaction liquid, and obtaining an intermediate 1-2-28-1 (yield 90%) through column chromatography.
Synthesis of intermediate 1-2-28-2: adding 0.1mol of 3-bromo-1, 10-phenanthroline and 0.35mol of KOH into 1.3L of water, stirring and heating to reflux reaction, and dropwise adding 0.3mol of KMNO4 into a hot solution in water (1L) after about 1 h. The mixture was refluxed for an additional 2h and then filtered hot. The filtrate was cooled, extracted with chloroform three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried under reduced pressure to obtain intermediate 1-2-28-2 (yield 50%) by column chromatography.
Synthesis of intermediates 1-2-28-3: dissolving 0.05mol of intermediate 1-2-28-2 in 150ml of toluene solvent, sequentially adding 0.05mol of 9, 10-dihydro-9, 9-dimethylacridine, 0.125mol of sodium tert-butoxide, 0.0005mol of tri-tert-butylphosphine and 0.0005mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and obtaining the intermediate 1-2-28-3 (the yield is 80%) by column chromatography.
Synthesis of Compounds 1-2-28: a solution of 0.04mol of intermediate 1-2-28-3 in 20ml of o-dichlorobenzene was added dropwise to 5ml of trifluoromethanesulfonic acid as a ketone solution. Adding 0.05mol of intermediate 1-2-28-1 into 130ml of anhydrous THF, stirring, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 0.05mol of 2.5mol/L n-butyllithium, keeping the temperature for 1 hour at-78 ℃, heating to room temperature, keeping for 2 hours, cooling to-78 ℃, adding the prepared ketone solution, heating to room temperature, adding water for quenching and filtering after 3 hours, extracting the filtrate for three times by using chloroform, drying by using anhydrous sodium sulfate, filtering, decompressing and spin-drying the filtrate, and obtaining the intermediate 1-2-28 (the yield is 25%) by column chromatography.
Mass spectrum: C38H27N3S, theoretical value: 557.19, found: 557.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 6.55-6.56 (2H, m), 6.73-6.81 (3H, m), 7.02-7.11 (9H, m), 7.33-7.35 (2H, m), 7.48-7.52 (1H, m), 7.63-7.65 (3H, m), 8.51-8.55 (1H, m).
Preparation example 20: compound 2-1
And (3) synthesizing an intermediate 2-1-1-1: dissolving 0.125mol of o-bromoiodobenzene in 300ml of NMP solvent, adding 0.125mol of o-bromophenol and 0.31mol of cesium carbonate, stirring, heating to 60 ℃ for reaction, detecting the completion of the reaction of the raw materials after 3h, performing reduced pressure spin drying on the reaction liquid, and obtaining an intermediate 2-1-1-1 (yield is 80%) through column chromatography.
And (2) synthesizing the intermediate 2-1-1-2, namely preparing a Grignard reagent, adding 0.01mol of the intermediate 2-1-1-1 and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.09mol of the intermediate 2-1-1-1 tetrahydrofuran saturated solution into the tetrahydrofuran saturated solution, preserving the heat and refluxing for about 1h, keeping the nitrogen for later use, adding 0.1mol of silicon tetrachloride and tetrahydrofuran into another three-neck flask, uniformly stirring, cooling to-5 ℃ under the protection of nitrogen, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping, keeping the temperature of the system not more than 10 ℃, stirring for 30min after finishing dripping, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping saturated ammonium chloride aqueous solution into the reaction solution, stirring for 5min, adding dichloromethane for extraction, performing pressure spin drying on the organic phase by using organic phase, and performing column chromatography on the residue to obtain the intermediate 2-1-1-2 (.
And (3) synthesizing an intermediate 2-1-1-3: preparation of the Grignard reagent TMPMgCl LiCl, 54ml of isopropyl magnesium chloride (1.3M), 0.07mol of lithium chloride were added to 16ml of tetrahydrofuran under nitrogen protection, 0.07mol of TMPH was slowly added dropwise with stirring, and the mixture was stirred at room temperature for 24 hours under nitrogen protection.
0.5mol of 5-bromo-2-methoxypyridine, 0.5mol of 3-bromopyridine, 0.025mol of nickel dichloride and 70ml of TMPMgCl LiCl (1.0M) were stirred at room temperature for 2 hours, a saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture, the mixture was stirred for 5 minutes and extracted with dichloromethane, the organic phase was removed and dried by spinning, and the residue was subjected to column chromatography to obtain intermediate 2-1-1-3 (yield 20%).
And (2) synthesizing the intermediate 2-1-1-4, namely preparing a Grignard reagent, adding 0.005mol of the intermediate 2-1-1-2 and 0.2mol of magnesium into 10ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.045mol of the intermediate 2-1-1-2 saturated tetrahydrofuran solution into another three-neck flask, keeping the temperature and refluxing for about 1h, keeping the nitrogen protection for later use, adding 0.5mol of the intermediate 2-1-3 and tetrahydrofuran into the other three-neck flask, uniformly stirring, protecting the nitrogen, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping, keeping the temperature of the system not more than 10 ℃, stirring for 30min after the dripping is finished, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping a saturated ammonium chloride aqueous solution into the reaction liquid, stirring for 5min, adding dichloromethane for extraction, taking the organic pressure for spin drying, and passing the residue through column chromatography to obtain the intermediate 2-1-1-4 (yield is 50%).
Synthesis of intermediate 2-1-1-5: 0.025mol of intermediate 2-1-1-4 is dissolved in 100ml of dichloromethane, 0.0275mol of boron tribromide is reacted for 2h at room temperature, organic phase is removed, spinning-drying is carried out under reduced pressure, and the residue is subjected to column chromatography to obtain intermediate 2-1-1-5 (yield 70%).
Synthesis of intermediate 2-1-1-6: dissolving 0.017mol of intermediate 2-1-1-5 in 60ml dichloromethane, dropwise adding trifluoromethanesulfonic anhydride, reacting at room temperature for 5h, taking the organic phase, performing vacuum spin drying, and performing column chromatography on the residue to obtain intermediate 2-1-1-6 (yield is 90%).
Synthesis of Compound 2-1-1: dissolving 0.015mol of intermediate 2-1-1-6 in 50ml of toluene solvent, sequentially adding 0.015mol of 9, 10-dihydro-9, 9-dimethylacridine, 0.0375mol of sodium tert-butoxide, 0.00015mol of tri-tert-butylphosphine and 0.00015mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 4 hours, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 2-1-1 (yield is 80%).
Mass spectrum: C34H21N3OSi, theoretical: 515.15, found: 515.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.09-7.12 (2H, m), 7.24-7.51 (11H, m), 7.63-7.65 (1H, m), 7.74-7.74 (1H, d), 7.85-7.85 (1H, d), 7.94-7.99 (2H, m), 8.12-8.15 (1H, m), 8.55-8.57 (1H, m), 8.63-8.66 (1H, m).
Preparation example 21: compound 2-1-5
Synthesis of Compounds 2-1-5: the synthesis method was the same as the synthesis of compound 1-1-29 to give compound 1-2-15 (yield 72%).
Mass spectrum: C34H21N3OSSi, theoretical value: 547.12, found: 547.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.42-7.43 (1H, m), 6.97-6.98 (2H, m), 7.16-7.24 (11H, m), 7.42-7.51 (4H, m), 7.63-7.64 (1H, m), 7.94-7.95 (1H, m), 8.63-8.64 (1H, m).
Preparation example 22: compound 2-1-11
Synthesis of intermediate 2-1-11-1: dissolving 0.125mol of o-bromoiodobenzene in 300ml of NMP solvent, adding 0.125mol of o-bromophenol and 0.31mol of cesium carbonate, stirring, heating to 60 ℃ for reaction, detecting the completion of the reaction of the raw materials after 3h, performing reduced pressure spin drying on the reaction liquid, and performing column chromatography to obtain an intermediate 2-1-11-1 (yield is 80%).
And (2) synthesizing an intermediate 2-1-11-2, namely preparing a Grignard reagent, adding 0.01mol of intermediate 2-1-11-1 and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.09mol of intermediate 2-1-11-1 tetrahydrofuran saturated solution into the tetrahydrofuran saturated solution, preserving the heat and refluxing for about 1h, keeping the nitrogen for later use, adding 0.1mol of silicon tetrachloride and tetrahydrofuran into another three-neck flask, uniformly stirring, reducing the temperature to-5 ℃ under the protection of nitrogen, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping the Grignard reagent, keeping the temperature of the system not more than 10 ℃, stirring for 30min after finishing dripping, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping saturated ammonium chloride aqueous solution into the reaction solution, stirring for 5min, adding dichloromethane for extraction, taking organic phase, performing pressure spin drying on the residue, and performing column chromatography on the intermediate 2-1-11-2 (yield 51.
Synthesis of intermediate 2-1-11-3: preparation of the Grignard reagent TMPMgCl LiCl, 54ml of isopropyl magnesium chloride (1.3M), 0.07mol of lithium chloride were added to 16ml of tetrahydrofuran under nitrogen protection, 0.07mol of TMPH was slowly added dropwise with stirring, and the mixture was stirred at room temperature for 24 hours under nitrogen protection.
0.5mol of 3-bromo-5-methoxypyridine, 0.5mol of 3-bromopyridine, 0.025mol of nickel dichloride and 70ml of TMPMgCl LiCl (1.0M) were stirred at room temperature for 2 hours, a saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture, the mixture was stirred for 5 minutes and extracted with dichloromethane, the organic phase was removed and dried by spinning, and the residue was subjected to column chromatography to obtain intermediate 2-1 to 11-3 (yield 20%).
And (2) synthesizing the intermediate 2-1-11-4, namely preparing a Grignard reagent, adding 0.005mol of the intermediate 2-1-11-2 and 0.2mol of magnesium into 10ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.045mol of the intermediate 2-1-11-2 saturated tetrahydrofuran solution into another three-neck flask, keeping the temperature and refluxing for about 1h, keeping the nitrogen protection for later use, adding 0.5mol of the intermediate 2-1-11-3 and tetrahydrofuran into the other three-neck flask, uniformly stirring, protecting the nitrogen, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping, keeping the temperature of the system not more than 10 ℃, stirring for 30min after the dripping is finished, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping a saturated ammonium chloride aqueous solution into a reaction liquid, stirring for 5min, adding dichloromethane for extraction, taking the organic phase for rotary drying by phase subtraction, and passing the residue through column chromatography to obtain the intermediate 2-1-11-4 (yield.
Synthesis of intermediate 2-1-11-5: 0.025mol of intermediate 2-1-11-4 is dissolved in 100ml of dichloromethane, 0.0275mol of boron tribromide is reacted for 2 hours at room temperature, organic phase is taken out, spinning-drying is carried out under reduced pressure, and the residue is subjected to column chromatography to obtain intermediate 2-1-11-5 (yield is 70%).
Synthesis of intermediate 2-1-11-6: dissolving 0.017mol of intermediate 2-1-11-5 in 60ml dichloromethane, dropwise adding trifluoromethanesulfonic anhydride, reacting at room temperature for 5h, taking the organic phase, performing vacuum spin drying, and performing column chromatography on the residue to obtain intermediate 2-1-11-6 (yield is 90%).
Synthesis of Compounds 2-1-11: dissolving 0.015mol of intermediate 2-1-11-6 in 50ml of toluene solvent, sequentially adding 0.015mol of 2-phenyl-9H-carbazole, 0.0375mol of sodium tert-butoxide, 0.00015mol of tri-tert-butylphosphine and 0.00015mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring, heating to reflux reaction, detecting that the reaction of the raw materials is finished after 4 hours, decompressing and spin-drying the reaction liquid, and performing column chromatography to obtain the compound 2-1-11 (yield is 65%).
Mass spectrum: C40H25N3OSi, theoretical: 591.18, found: 591.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.09-7.10 (2H, m), 7.24-7.52 (14H, m), 7.62-7.63 (1H, m), 7.79-7.85 (2H, m), 7.94-7.95 (2H, m), 8.18-8.19 (1H, m), 8.46-8.46 (1H, s), 8.55-8.56 (1H, m), 8.63-8.64 (1H, m).
Preparation example 23: compounds 2-1-14
Synthesis of Compounds 2-1-14: the synthesis method was followed by synthesis of compound 1-1-29 to give compound 1-2-14 (yield 68%).
Mass spectrum: C34H21N3OSSi, theoretical value: 547.12, found: 547.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.42-7.43 (1H, m), 6.97-6.98 (2H, m), 7.16-7.24 (11H, m), 7.42-7.51 (5H, m), 7.75-7.76 (1H, m), 7.94-7.95 (1H, m), 8.63-8.64 (1H, m).
Preparation example 24: compounds 2-1-19
Synthesis of Compounds 2-1-19: dissolving 0.10mol of intermediate 2-1-11-6 in 400ml of toluene solvent, sequentially adding 0.10mol of 5H- [1] benzothieno [3,2-c ] carbazole, 0.25mol of sodium tert-butoxide, 0.001mol of tri-tert-butylphosphine and 0.001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography to obtain the compound 2-1-19 (yield is 62%).
Mass spectrum: C40H23N3OSSi, theoretical value: 621.13, found: 547.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.09-7.10 (2H, m), 7.24-7.52 (12H, m), 7.85-7.86 (1H, m), 7.94-8.05 (4H, m), 8.45-8.46 (2H, m), 8.55-8.56 (1H, m), 8.63-8.64 (1H, m).
Preparation example 25: compounds 2-1-24
Synthesis of intermediate 2-1-24-1: dissolving 0.125mol of o-bromoiodobenzene in 300ml of NMP solvent, adding 0.125mol of o-bromophenol and 0.31mol of cesium carbonate, stirring, heating to 60 ℃ for reaction, detecting the completion of the reaction of the raw materials after 3h, performing reduced pressure spin drying on the reaction liquid, and obtaining an intermediate 2-1-24-1 (yield is 80%) through column chromatography.
And (2) synthesizing an intermediate 2-1-24-2, namely preparing a Grignard reagent, adding 0.01mol of intermediate 2-1-24-1 and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.09mol of intermediate 2-1-24-1 tetrahydrofuran saturated solution into the tetrahydrofuran saturated solution, preserving the heat and refluxing for about 1h, keeping the nitrogen for later use, adding 0.1mol of silicon tetrachloride and tetrahydrofuran into another three-neck flask, uniformly stirring, reducing the temperature to-5 ℃ under the protection of nitrogen, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping the Grignard reagent, keeping the temperature of the system not more than 10 ℃, stirring for 30min after finishing dripping, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping saturated aqueous solution of ammonium chloride into the reaction solution, stirring for 5min, adding dichloromethane for extraction, taking organic phase, performing pressure spin drying on the residue, and performing column chromatography on the intermediate 2-1-24-2 (yield 51%).
Synthesis of intermediates 2-1-24-3: preparation of the Grignard reagent TMPMgCl LiCl, 54ml of isopropyl magnesium chloride (1.3M), 0.07mol of lithium chloride were added to 16ml of tetrahydrofuran under nitrogen protection, 0.07mol of TMPH was slowly added dropwise with stirring, and the mixture was stirred at room temperature for 24 hours under nitrogen protection.
0.5mol of 5-bromo-2-methoxypyridine, 0.5mol of 2-bromopyridine, 0.025mol of nickel dichloride and 70ml of TMPMgCl LiCl (1.0M) were stirred at room temperature for 2 hours, a saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture, the mixture was stirred for 5 minutes and extracted with dichloromethane, the organic phase was removed and dried by spinning, and the residue was subjected to column chromatography to obtain intermediate 2-1 to 24-3 (yield 6%).
And (2) synthesizing the intermediate 2-1-24-4, namely preparing a Grignard reagent, adding 0.005mol of the intermediate 2-1-24-2 and 0.2mol of magnesium into 10ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dripping the rest 0.045mol of the intermediate 2-1-24-2 saturated tetrahydrofuran solution into another three-neck flask, keeping the temperature and refluxing for about 1h, keeping the nitrogen protection for later use, adding 0.5mol of the intermediate 2-1-24-3 and tetrahydrofuran into the other three-neck flask, uniformly stirring, protecting the nitrogen, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dripping, keeping the temperature of the system not more than 10 ℃, stirring for 30min after the dripping is finished, slowly heating to room temperature, detecting that the reaction of the raw materials is finished after 5h, dripping a saturated ammonium chloride aqueous solution into the reaction liquid, stirring for 5min, adding dichloromethane for extraction, taking the organic pressure for spin drying, and passing the residue through column chromatography to obtain the intermediate 2-1-24-4 (yield is 50.
Synthesis of intermediates 2-1-24-5: 0.025mol of intermediate 2-1-24-4 is dissolved in 100ml of dichloromethane, 0.0275mol of boron tribromide is reacted for 2 hours at room temperature, organic phase is taken out, spinning-drying is carried out under reduced pressure, and the residue is subjected to column chromatography to obtain intermediate 2-1-24-5 (yield is 70%).
Synthesis of intermediates 2-1-24-6: dissolving 0.017mol of intermediate 2-1-24-5 in 60ml dichloromethane, dropwise adding trifluoromethanesulfonic anhydride, reacting at room temperature for 5h, taking the organic phase, performing vacuum spin drying, and performing column chromatography on the residue to obtain intermediate 2-1-24-6 (yield is 90%).
Synthesis of Compounds 2-1-24: 0.01mol of intermediate 2-1-24-6 is dissolved in a mixed solvent of 50ml of 1, 4-dioxane and 5ml of water, 0.12mol of (9-phenyl-9H-carbazole-3-yl) boric acid is added, then 0.25mol of sodium carbonate and 0.0001mol of tetratriphenylphosphine palladium catalyst are added, and reflux is carried out for 2 hours under the condition of nitrogen. After the reaction is finished, removing sodium carbonate and a palladium catalyst of tetratriphenylphosphine, and purifying by column chromatography to obtain the compound 2-1-24 (the yield is 72%).
Mass spectrum: C40H25N3OSi, theoretical: 591.18, found: 591.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.09-7.10 (2H, m), 7.24-7.29 (3H, m), 7.42-7.63 (12H, m), 7.81-7.82 (1H, m), 8.03-8.04 (2H, m), 8.12-8.13 (1H, m), 8.28-8.29 (1H, m), 8.53-8.58 (2H, m), 8.69-8.70 (1H, m).
Preparation example 26: compound 2-2-3
And (3) synthesizing an intermediate 2-2-3-1: 30ml of 1M n-butyllithium n-hexane solution is put into a 250ml reaction bottle, cooled to-78 ℃ under the protection of nitrogen, and stirred for 10 minutes. Slowly dripping 0.01mol of bis (2-bromophenyl) sulfane into 50ml of THF solution for about 45 minutes, and stirring for 2 hours at the temperature of-78 ℃ to-60 ℃ after finishing dripping. 0.02mol of silicon tetrachloride is added, and the temperature is controlled not to exceed 5 ℃. After the feeding is finished, the temperature is naturally raised to the room temperature, and the mixture is stirred for 5 hours. After the reaction, 30ml of saturated ammonium chloride solution was added dropwise, the mixture was stirred for 30 minutes, and extracted with 50ml of DCM 3 times. The organic layers were combined, washed 1 time with 50ml of saturated brine, dried over anhydrous sodium sulfate, concentrated to dryness to give a yellow-white solid, and purified by column chromatography (EA: PE ═ 1:10) to give intermediate 2-2-3-1, yield 67%).
And (3) synthesizing an intermediate 2-2-3-2: 30ml of 1M n-butyllithium n-hexane solution is put into a 250ml reaction bottle, cooled to-78 ℃ under the protection of nitrogen, and stirred for 10 minutes. Slowly dropwise adding 0.01mol of 3,3 '-dibromo-2, 2' -bipyridine into 50ml of THF solution, finishing dropping within about 45 minutes, and then controlling the temperature to be between-78 ℃ and-60 ℃ and stirring for 2 hours. 0.01mol of intermediate 2-2-3-1 is added, and the temperature is controlled not to exceed 5 ℃. After the feeding is finished, the temperature is naturally raised to the room temperature, and the mixture is stirred for 5 hours. After the reaction, 30ml of saturated ammonium chloride solution was added dropwise, the mixture was stirred for 30 minutes, and extracted with 50ml of DCM 3 times. The organic layers were combined, washed with 50ml of saturated brine for 1 time, dried over anhydrous sodium sulfate, concentrated to dryness to give a yellow-white solid, and purified by column chromatography (EA: PE ═ 1:8) to give intermediate 2-2-3-2 (yield 81%).
And (3) synthesizing an intermediate 2-2-3-3: putting 0.01mol of intermediate 2-2-3-2 into a 250ml reaction bottle, adding 50ml of DMF, controlling the temperature in an ice-water bath, stirring for 5 minutes, dropwise adding 0.01mol of NBS, after dropwise adding for about 30 minutes, continuously stirring the ice-water bath for 10 minutes, naturally returning to the room temperature, then heating to 50 ℃, stirring for 4 hours, adding 100ml of purified water into the reaction solution, cooling to the room temperature while stirring, continuously stirring for 30 minutes, filtering to obtain a crude product, and drying (50 ℃, 6 hours) by hot air to obtain the intermediate 2-2-3-3 (yield 83%) through column chromatography purification.
Synthesis of Compounds 2-2-3: 0.001mol of intermediate 2-2-3-3, 0.011mol of 3- (9H-carbazole-9-yl) phenylboronic acid, 0.025mol of potassium carbonate, 200ml of 1, 4-dioxane, 10ml of water, 0.5mmol of tricyclohexylphosphine, 1mmol of tricyclohexylphosphine tetrafluoroborate and 3mmol of palladium acetate are put into a 500ml reaction bottle under the protection of nitrogen, the mixture is heated to reflux under stirring once nitrogen displacement is performed, the mixture is continuously stirred for 4 hours, reaction liquid is dried by spinning after the reaction is completed, 200ml of toluene is added and heated to reflux, 200-mesh 300-mesh silica gel with the thickness of 1cm is paved on a Buchner funnel, and the mixture is filtered while the mixture is hot. And (4) spin-drying the filtrate, and recrystallizing by 3 times of toluene to obtain a compound 2-2-3. (yield 82%)
Mass spectrum: C40H25N3SSi, theoretical: 607.15, found: 607.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.11-7.15 (2H, m), 7.24-7.35 (8H, m), 7.50-7.54 (5H, m), 7.63-7.66 (2H, m), 7.81-7.85 (1H, m), 7.94-7.99 (2H, m), 8.12-8.15 (1H, m), 8.30-8.33 (1H, m), 8.55-8.63 (3H, m).
Preparation example 27: compound 2-2-5
Synthesis of Compounds 2-2-5: dissolving 0.01mol of intermediate 2-2-3-3 in 40ml of toluene solvent, sequentially adding 0.01mol of 11-phenyl-11, 12-indolino [2,3-a ] carbazole, 0.025mol of sodium tert-butoxide, 0.0001mol of tri-tert-butylphosphine and 0.0001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5 hours, carrying out reduced pressure spin drying on reaction liquid, and obtaining the compound 1-1-20 (yield 82%) by column chromatography.
Mass spectrum: C46H28N4SSi, theoretical: 696.18, found: 696.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.11-7.15 (2H, m), 7.24-7.58 (17H, m), 7.74-7.75 (1H, m), 7.85-7.86 (1H, m), 7.94-7.95 (3H, m), 8.11-8.12 (1H, m), 8.55-8.56 (2H, m), 8.63-8.64 (1H, m).
Preparation example 28: compound 2-2-28
And (3) synthesizing the intermediate 2-2-28-1, namely adding 30ml of 1M n-butyllithium n-hexane solution into a 250ml reaction bottle, cooling to-78 ℃ under the protection of nitrogen, and stirring for 10 minutes. Slowly dropwise adding 0.01mol of 2', 1, 3-dibromo-2, 3' -bipyridyl into 50ml of THF solution, finishing dropping within about 45 minutes, and then controlling the temperature to be between-78 ℃ and-60 ℃ and stirring for 2 hours. 0.01mol of intermediate 2-2-2-3-1 is added, and the temperature is controlled not to exceed 5 ℃. After the feeding is finished, the temperature is naturally raised to the room temperature, and the mixture is stirred for 5 hours. After the reaction, 30ml of saturated ammonium chloride solution was added dropwise, the mixture was stirred for 30 minutes, and extracted with 50ml of DCM 3 times. The organic layers were combined, washed with 50ml of saturated brine for 1 time, dried over anhydrous sodium sulfate, concentrated to dryness, and purified by column chromatography (EA: PE ═ 1:8) to give intermediate 2-2-28-1 (yield 81%).
Synthesis of intermediate 2-2-28-2: adding 0.01mol of intermediate 2-2-28-1 into a 250ml reaction bottle, adding 50ml of DMF, controlling the temperature in an ice water bath, stirring for 5 minutes, dropwise adding 0.01mol of NBS, after about 30 minutes of dropwise addition, after the dropwise addition is finished, continuously stirring the ice water bath for 10 minutes, naturally returning to the room temperature, then heating to 50 ℃, stirring for 4 hours, adding 100ml of purified water into the reaction solution, cooling to the room temperature under stirring, continuously stirring for 30 minutes, filtering to obtain a crude product, drying by hot air (50 ℃, 6 hours), and purifying by column chromatography (EA: PE 1:8) to obtain intermediate 2-2-28-2 (yield 83%).
Synthesis of Compounds 2-2-28: dissolving 0.01mol of intermediate 2-2-28-2 in 40ml of toluene solvent, sequentially adding 0.01mol of 11, 11-dimethyl-5, 11-dihydroindeno [1,2-b ] carbazole, 0.025mol of sodium tert-butoxide, 0.0001mol of tri-tert-butylphosphine and 0.0001mol of tris (dibenzylideneacetone) dipalladium under the protection of nitrogen, stirring and heating until reflux reaction is carried out, detecting that the reaction of the raw materials is finished after 5 hours, carrying out reduced pressure spin drying on reaction liquid, and obtaining the compound 1-1-20 (yield 80%) by column chromatography.
Mass spectrum: C43H29N3SSi, theoretical: 647.19, found: 647.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.72-1.72 (6H, s), 7.11-7.15 (2H, m), 7.24-7.61 (13H, m), 7.94-8.00 (2H, m), 8.09-8.12 (2H, m), 8.52-8.58 (4H, m).
Preparation example 29: synthesis of Compounds 2-2-22:
synthesis of Compounds 2-2-22: 0.01mol of intermediate 2-2-28-2, 0.011mol of 3- (9H-carbazole-9-yl) phenylboronic acid, 0.025mol of potassium carbonate, 200ml of 1, 4-dioxane, 10ml of water, 0.5mmol of tricyclohexylphosphine, 1mmol of tricyclohexylphosphine tetrafluoroborate and 3mmol of palladium acetate are put into a 500ml reaction bottle under the protection of nitrogen, the mixture is heated to reflux under stirring once nitrogen displacement is performed, the mixture is continuously stirred for 4 hours, reaction liquid is dried by spinning after the reaction is completed, 200ml of toluene is added and heated to reflux, 200-mesh 300-mesh silica gel with the thickness of 1cm is paved on a Buchner funnel, and the mixture is filtered while the mixture is hot. The filtrate was spin-dried and 3-fold recrystallized from toluene to obtain 2-2-22 (yield 80%).
Mass spectrum: C40H25N3SSi, theoretical: 607.15, found: 607.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.11-7.15 (2H, m), 7.25-7.35 (7H, m), 7.46-7.63 (8H, m), 7.94-7.99 (1H, m), 8.09-8.12 (2H, m), 8.31-8.33 (1H, m), 8.53-8.58 (3H, m), 8.93-8.94 (1H, m).
Example 1: preparation of organic light emitting device
After ultrasonically washing a glass substrate having an Indium Tin Oxide (ITO) electrode ( th electrode, anode) having a thickness of about 1500 angstroms with distilled water and methanol in sequence, the washed glass substrate was dried, moved to a plasma cleaning system, and then cleaned using an oxygen plasma for about 5 minutes.
Vacuum depositing HAT-CN onto the ITO electrode of the glass substrate to form a HIL having a thickness of about 100 angstroms; TAPC was vacuum deposited to a thickness of 300 angstroms onto the hole injection layer followed by 100 angstroms of mCP to form the HTL.
Reacting the Compound 1-1-1 with Ir (ppy))3And (3) mixing the following raw materials in a ratio of 95: a weight ratio of 5 was co-deposited on the hole transport region to form an EML having a thickness of about 300 angstroms.
Subsequently, BCP was vacuum deposited on the EML to form an ETL having a thickness of about 300 angstroms. Then, LiF was deposited on the ETL to form an EIL having a thickness of about 10 angstroms, and Al was deposited on the EIL to a thickness of about 1000 angstroms to form a second electrode (cathode), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 32
Organic light-emitting devices of the remaining examples were prepared in a similar manner to example 1, except that the compounds shown in table 1 were used instead of compound 1-1-1 in example 1.
Comparative example 1
An organic light-emitting device was produced in a similar manner to that in example 1, except that compound M-1 was used instead of compound 1-1-1 in example 1.
Evaluation: evaluation of characteristics of organic light-emitting device
The driving voltage, emission efficiency and lifetime of the organic light emitting devices in examples and comparative examples were measured using a current-voltage source meter (Keithley 2400) and a Minolta CS-1000A spectroradiometer, and the wavelengths in examples and comparative examples were measured using I-V-L. The results are shown in table 1 below.
(1) Measurement of current density change with respect to voltage change
Current density was obtained by measuring current value of every flowing through the organic light emitting device while increasing the voltage from 0 volt (V) to about 10V by using a current-voltage source meter (Keithley 2400), and then dividing it by the area of the corresponding light emitting device.
(2) Measurement of brightness variation with respect to voltage variation
The brightness of the organic light emitting device was measured while increasing the voltage from about 0V to about 10V by using a Minolta CS-1000A spectroradiometer.
(3) Measurement of emission efficiency
The organic light emitting device was calculated at 20 milliamperes per square centimeter (Ma/cm) based on the current density, voltage, and luminance obtained from the measurements (1) and (2) described above2) current efficiency at constant current density.
(4) Measurement of lifetime
Maintaining an initial luminance of 10000cd/m2Current density at the time of the measurement, and luminance (cd/m)2) Decrease to 90% time.
TABLE 1
As can be seen from the experimental results shown in table 1, the organic compound of the present invention forms an organic electroluminescent device having a low driving voltage, a high current efficiency, a high luminance, and a long lifespan, as compared to the prior art.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1, kinds of organic compound, the compound has the structure shown in formula (I) or formula (II),
wherein, in the formula (I) and the formula (II),
x is O or S, and X is O or S,
z is C or Si, and Z is C or Si,
R11and R12Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing arylheterocyclic group, substituted phenyl group, and substituted or unsubstituted diphenylamine group;
R21and R22Wherein are H and are selected from the group consisting of substituted or unsubstituted nitrogen-containing aryltricyclic group, substituted or unsubstituted nitrogen-containing arylpentacyclic group, substituted phenyl group, substituted or unsubstituted dianilino group, and
R11、R12、R21and R22Each substituent on is independently selected from C1-3At least of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl groups of (a).
2. The organic compound according to claim 1, wherein, in the formula (I) and the formula (II),
the nitrogen-containing aromatic heterocyclic tricyclic in the substituted or unsubstituted nitrogen-containing aromatic heterocyclic tricyclic is a tricyclic shown in a formula (I1) or a formula (I2), and any position in the tricyclic shown in the formula (I1) and the formula (I2) which can be connected in a bonding mode is connected with the mother nucleus in the formula (I) and the formula (II) through a C-C bond or a C-N bond;
wherein Y in formula (I2) is O, S, C or N atom;
and the C atom and/or the N atom in the tricyclic ring represented by the formula (I1) and the formula (I2) are optionally substituted by a group selected from C1-3At least groups of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl of (a);
3. the organic compound according to claim 1 or 2, wherein, in the formula (I) and the formula (II),
the nitrogen-containing aromatic pentacyclic ring in the substituted or unsubstituted nitrogen-containing aromatic pentacyclic ring is selected from pentacyclic rings shown in formulas (II1) to (II6),
wherein X in the formulae (II1) to (II6)1、X2、X3、X4、X5And X6Each independently selected from O, S, C and an N atom;
and the C atom and/or the N atom in the pentacyclic ring shown in the formulas (II1) to (II6) are optionally selected from C1-3At least groups of alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, and phenyl-substituted carbazolyl of (a);
4. the organic compound according to claim 1, wherein the substituted or unsubstituted dianilino group is represented by formula (III) in formula (I) and formula (II),
R31and R32Is selected from H, C1-3At least groups selected from alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl and carbazolyl.
5. The organic compound according to claim 1, wherein the compound having the structure represented by formula (I) or formula (II) is selected from any of the following compounds:
6. the organic compound according to claim 5, wherein the compound having the structure represented by formula (I) or formula (II) is selected from any of the following compounds:
7. use of an organic compound of any of claims 1-6 in an organic electroluminescent device.
8, kinds of organic electroluminescent devices containing or more kinds of the organic compounds according to any of claims 1 to 6, preferably,
the organic compound is present in at least layers among an electron transport layer, a light emitting layer, and a hole blocking layer of the organic electroluminescent device.
9. The organic electroluminescent device according to claim 8, wherein the organic compound is present in a light-emitting layer of the organic electroluminescent device; preferably, the first and second electrodes are formed of a metal,
the organic compound serves as a host material in the light-emitting layer.
10. The organic electroluminescent device according to claim 8 or 9, wherein the organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked.
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| CN111285879A (en) * | 2018-12-07 | 2020-06-16 | 乐金显示有限公司 | Novel compound, and organic light emitting device and organic light emitting display device including the same |
| CN111518109A (en) * | 2019-02-01 | 2020-08-11 | 北京绿人科技有限责任公司 | Organic compound, application thereof and organic electroluminescent device |
| CN114276361A (en) * | 2020-09-28 | 2022-04-05 | 北京绿人科技有限责任公司 | Organic compound and organic electroluminescent device containing same |
| CN116554200A (en) * | 2022-01-28 | 2023-08-08 | 北京绿人科技有限责任公司 | Nitrogen-containing organic compound, application thereof and organic electroluminescent device |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285879A (en) * | 2018-12-07 | 2020-06-16 | 乐金显示有限公司 | Novel compound, and organic light emitting device and organic light emitting display device including the same |
| CN111285879B (en) * | 2018-12-07 | 2022-08-30 | 乐金显示有限公司 | Novel compound, and organic light emitting device and organic light emitting display device including the same |
| CN111518109A (en) * | 2019-02-01 | 2020-08-11 | 北京绿人科技有限责任公司 | Organic compound, application thereof and organic electroluminescent device |
| CN111518109B (en) * | 2019-02-01 | 2021-10-01 | 北京绿人科技有限责任公司 | Organic compound, application thereof and organic electroluminescent device |
| CN114276361A (en) * | 2020-09-28 | 2022-04-05 | 北京绿人科技有限责任公司 | Organic compound and organic electroluminescent device containing same |
| CN116554200A (en) * | 2022-01-28 | 2023-08-08 | 北京绿人科技有限责任公司 | Nitrogen-containing organic compound, application thereof and organic electroluminescent device |
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