CN115073445B - 基于硒杂蒽酮的有机发光材料及其制备方法与应用 - Google Patents
基于硒杂蒽酮的有机发光材料及其制备方法与应用 Download PDFInfo
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- CN115073445B CN115073445B CN202110264914.9A CN202110264914A CN115073445B CN 115073445 B CN115073445 B CN 115073445B CN 202110264914 A CN202110264914 A CN 202110264914A CN 115073445 B CN115073445 B CN 115073445B
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- Prior art keywords
- selenohexanthrone
- luminescent material
- benzoic acid
- catalyst
- organic luminescent
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- 239000000463 material Substances 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 238000003384 imaging method Methods 0.000 claims abstract description 4
- 230000001699 photocatalysis Effects 0.000 claims abstract description 4
- 238000007146 photocatalysis Methods 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 239000000543 intermediate Substances 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 21
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000003513 alkali Substances 0.000 claims description 16
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 claims description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004327 boric acid Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- -1 II Chemical compound 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 235000011181 potassium carbonates Nutrition 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 5
- 235000011009 potassium phosphates Nutrition 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 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 claims description 3
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 2
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- LEFPWWWXFFNJAA-UHFFFAOYSA-N dicyclohexylphosphorylcyclohexane Chemical compound C1CCCCC1P(C1CCCCC1)(=O)C1CCCCC1 LEFPWWWXFFNJAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000532 dioxanyl group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 150000001559 benzoic acids Chemical group 0.000 claims 1
- 238000003818 flash chromatography Methods 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 239000007787 solid Substances 0.000 description 18
- 150000002430 hydrocarbons Chemical group 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000000171 quenching effect Effects 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000010183 spectrum analysis Methods 0.000 description 8
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 239000013256 coordination polymer Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- LAXRNWSASWOFOT-UHFFFAOYSA-J (cymene)ruthenium dichloride dimer Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ru+2].[Ru+2].CC(C)C1=CC=C(C)C=C1.CC(C)C1=CC=C(C)C=C1 LAXRNWSASWOFOT-UHFFFAOYSA-J 0.000 description 2
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- DHMPDNLGFIBQCK-UHFFFAOYSA-N 3,4-dibromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(Br)=C1 DHMPDNLGFIBQCK-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical group 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
-
- 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
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Abstract
本发明涉及一种基于硒杂蒽酮的有机发光材料及其制备方法与应用,属于有机发光材料技术领域。本发明的基于硒杂蒽酮的有机发光材料具有式(I)或者式(II)所示结构通式,其中D1、D2各自独立的选自芳环、芳杂环或者稠芳杂环等;所述的D1、D2通过C‑N或C‑C键与硒杂蒽酮的苯环上任意位置相连;m、n各自独立的选自1~4的整数。本发明的有机发光材料能克服纯有机室温磷光材料在膜态条件下发光效率偏低的问题,实现在膜态下高的发光效率,在光学传感、电致发光器件、光催化、光存储、防伪标识和成像等领域具有应用前景。
Description
技术领域
本发明属于有机发光材料技术领域,具体涉及一种基于硒杂蒽酮的有机发光材料及其制备方法与应用。
背景技术
近年来,随着光电子器件领域的发展,尤其是有机电致发光二极管(OLED)所展示出的广阔应用前景,有机发光材料在科学界和产业界得到了广泛的研究与关注。有机发光材料主要分为传统荧光材料、延迟荧光材料与磷光材料。与传统荧光材料相比,延迟荧光材料与磷光材料均能够利用三线态激子的能量,可以有效的提升发光效率。然而,由于三线态激子与单线态不同,三线态激子的直接辐射跃迁通常为禁阻过程,在多数情况下,三线态激子主要通过非辐射跃迁回到基态,从而造成三线态激子损失,激子利用率偏低,导致发光效率较低。因此,目前所广泛研究与使用的磷光材料是以金属配合物为主的传统磷光材料。这类材料借助Ru、Pt、Ir等重金属元素的重原子效应,促进电子的自旋翻转,进而促进系间窜越与三线态激子的辐射跃迁,增强磷光发射,从而获得高的发光效率。尽管一些金属配合物磷光材料已实现了商业化,但由于价格昂贵的重金属元素的使用,导致其品种有限、成本高昂。而不含贵金属的纯有机室温磷光材料成本相对便宜、结构容易调节、有着良好的加工性,因此发展纯有机室温磷光材料具有重要意义。然而,纯有机材料由于自旋轨道耦合效应弱,系间窜越过程慢,导致三线态激子主要通过非辐射过程失活,所以目前能够呈现室温磷光行为的纯有机小分子种类稀少,发光效率普遍较低,极大限制了这类材料的应用。
发明内容
本发明要解决现有技术中的技术问题,提供一种基于硒杂蒽酮的有机发光材料及其制备方法与应用。
为了解决上述技术问题,本发明的技术方案具体如下:
本发明提供一种基于硒杂蒽酮的有机发光材料,该化合物具有式(I)或者式(II)所示结构通式:
式(I)和式(II)中:
D1、D2各自独立的选自芳环、芳杂环或者稠芳杂环等;所述的D1、D2通过C-N或C-C键与硒杂蒽酮的苯环上任意位置相连;m、n各自独立的选自1~4的整数。
在上述技术方案中,优选的是:D1、D2各自独立的为式(2-1)~(2-70)电子给体单元中的一种:
其中,L1、L2、L3和L4各自独立的选自H、卤素、-CN、-NO2、-PO(Ph)2、苯基、吡啶基、嘧啶基、三嗪基、取代或非取代的C1~C22的直链烃基、取代或非取代的C1~C22的支链烃基、取代或非取代的C1~C22的环烷基、或者取代或非取代的C1~C22的烷氧基;优选自H、卤素、-CN、-NO2、-PO(Ph)2、取代或非取代的C2~C20的直链烃基、取代或非取代的C2~C20的支链烃基、取代或非取代的C2~C20的环烷基、或者取代或非取代的C2~C20的烷氧基;进一步优选自H、卤素、-CN、-NO2、-PO(Ph)2、取代或非取代的C3~C18的直链烃基、取代或非取代的C3~C18的支链烃基、取代或非取代的C3~C18的环烷基、或者取代或非取代的C3~C18的烷氧基;再进一步优选自H、卤素、-CN、-NO2、-PO(Ph)2、取代或非取代的C5~C15的直链烃基、取代或非取代的C5~C15的支链烃基、取代或非取代的C5~C15的环烷基、或者取代或非取代的C5~C15的烷氧基;最优选自H、卤素、-CN、-NO2、-PO(Ph)2、取代或非取代的C8~C12的直链烃基、取代或非取代的C8~C12的支链烃基、取代或非取代的C8~C12的环烷基、或者取代或非取代的C8~C12的烷氧基;
L5、L6和L7各自独立的选自H、苯基、吡啶基、嘧啶基、三嗪基、-CN、取代或非取代的C1~C22的直链烃基、取代或非取代的C1~C22的支链烃基、取代或非取代的C1~C22的环烷基、或者取代或非取代的C1~C22的烷氧基;优选自H、取代或非取代的C2~C20的直链烃基、取代或非取代的C2~C20的支链烃基、取代或非取代的C2~C20的环烷基、或者取代或非取代的C2~C20的烷氧基;进一步优选自H、取代或非取代的C3~C18的直链烃基、取代或非取代的C3~C18的支链烃基、取代或非取代的C3~C18的环烷基、或者取代或非取代的C3~C18的烷氧基;再进一步优选自H、取代或非取代的C5~C15的直链烃基、取代或非取代的C5~C15的支链烃基、取代或非取代的C5~C15的环烷基、或者取代或非取代的C5~C15的烷氧基;最优选自H、取代或非取代的C8~C12的直链烃基、取代或非取代的C8~C12的支链烃基、取代或非取代的C8~C12的环烷基、或者取代或非取代的C8~C12的烷氧基。
在上述技术方案中,最优选的是:所述基于硒杂蒽酮的有机发光材料选自下述结构之一:
本发明还提供一种基于硒杂蒽酮的有机发光材料的制备方法,包括以下步骤:
步骤I:硒杂蒽酮中间体的制备
第一步:在空气条件下,苯甲酸或者苯甲酸衍生物,二苯基二硒醚或者二苯基二硒醚衍生物,催化剂,配体,碱和有机溶剂在反应瓶中混合,加热90℃~120℃,反应20~60小时,冷却至室温后,加入醋酸酸化,乙酸乙酯萃取,饱和食盐水洗涤三次,除去溶剂后,获得中间体粗产物后,无需分离;
第二步将步骤一获得的中间体粗产物直接和酸混合后,进一步加热至90℃~120℃,反应1~12小时,反应结束后冷却至室温,乙酸乙酯萃取,饱和食盐水洗涤,除去溶剂,快速柱层析,获得硒杂蒽酮中间体,并且硒杂蒽酮中间体中最少存在一个卤素取代基;
所述的苯甲酸衍生物为单卤代苯甲酸或者多卤代苯甲酸,并且卤代位点为苯环上任意可取代位置;
所述的二苯基二硒醚衍生物为单卤代二苯基二硒醚或者多卤代二苯基二硒醚,并且卤代位点为苯环上任意可取代位置;
步骤II:
当硒杂蒽酮中间体与D1、D2均通过C-N键相连时,通过Buchwald偶联反应合成,即方法A,具体步骤为:
在惰性气氛下,将硒杂蒽酮中间体,与D1芳胺原料、或者分别与D1、D2芳胺原料,催化剂,配体,碱和有机溶剂混合后,加热至90℃~120℃,反应时间为5~36小时,得到式(I)或者式(II)所示的基于硒杂蒽酮的有机发光材料;
当硒杂蒽酮中间体与D1、D2均通过C-C键相连时,通过Suzuki偶联反应合成,即方法B,具体步骤为:
在惰性气氛下,将硒杂蒽酮中间体,与D1硼酸原料,或者分别与D1、D2硼酸原料,催化剂,碱和有机溶剂混合后,加热至90℃~120℃,反应时间为5~36小时,得到式(I)或者式(II)所示的基于硒杂蒽酮的有机发光材料。
在上述技术方案中,优选的是:步骤I第一步中,所述的催化剂为二氯双(4-甲基异丙基苯基)钌(II);所述的配体为三环己基膦或者三环己基氧膦;所述的碱为碳酸钾、碳酸钠、碳酸氢钾、磷酸钾或者碳酸氢钠,特别优选为碳酸钠或者碳酸氢钠;所述的有机溶剂为1,4-二氧六环、四氢呋喃、甲苯、N,N-二甲基乙酰胺或者N,N-二甲基甲酰胺,特别优选为N,N-二甲基甲酰胺;步骤I第二步中,所述的酸为浓硫酸或者三氟甲磺酸,特别优选为三氟甲磺酸。
在上述技术方案中,优选的是:所述苯甲酸或者苯甲酸衍生物与二苯基二硒醚或者二苯基二硒醚衍生物的摩尔比为1:1~1:10,特别优选为1:2;
所述苯甲酸或者苯甲酸衍生物、催化剂、配体的摩尔比为1:0.01:0.01~1:0.1:0.1,特别优选为1:0.04:0.04;
所述苯甲酸或者苯甲酸衍生物与碱的摩尔比为1:1;
所述苯甲酸或者苯甲酸衍生物与酸的比例为1g:5mL~1g:50mL,特别优选为1g:25mL。
在上述技术方案中,优选的是:步骤I中,所述第一步加热反应温度为105℃,时间为36小时;所述第二步加热反应温度为100℃,时间为5小时。
在上述技术方案中,优选的是:步骤II中,所述的方法A中,催化剂为三(二亚苄基丙酮)二钯或者醋酸钯,特别优选为三(二亚苄基丙酮)二钯;碱为碳酸铯、叔丁醇钾或者叔丁醇钠,特别优选为叔丁醇钠;配体为(±)-2,2'-双-(二苯膦基)-1,1'-联萘、三叔丁基膦、三(邻甲基苯基)膦或者4,5-双二苯基膦-9,9-二甲基氧杂蒽,特别优选为三叔丁基膦;有机溶剂为二氧六环、甲苯或者二甲苯,特别优选为甲苯或者二甲苯;
所述的方法B中,催化剂为四(三苯基膦)钯、双(三苯基膦)二氯化钯(II)、[1,1'-双(二苯基膦基)二茂铁]二氯化钯、1,4-双(二苯基膦丁烷)二氯化钯、双(2-甲基烯丙基)氯化钯、氯化钯、碘化钯或者三二亚苄基丙酮二钯,特别优选为双(三苯基膦)二氯化钯(II)或者[1,1'-双(二苯基膦基)二茂铁]二氯化钯,更优选为四(三苯基膦)钯或者三二亚苄基丙酮二钯;碱为碳酸钠、碳酸钾、磷酸钾、叔丁醇钠或者碳酸铯,特别优选为碳酸钠或者磷酸钾,更优选为碳酸钾;有机溶剂为二甲基亚砜、N,N-二甲基甲酰胺、二氧六环、甲苯或者二甲苯,特别优选为二甲基亚砜、甲苯或者二甲苯。
在上述技术方案中,优选的是:步骤II中,所述的方法A中,硒杂蒽酮中间体与D1芳胺原料或者D2芳胺原料的摩尔比为1:1~1:5,特别优选为1:1.5;
所述硒杂蒽酮中间体与催化剂摩尔比为1:0.01~1:0.2,特别优选为1:0.1;
所述催化剂与配体的摩尔比为1:1~1:3;
所述硒杂蒽酮中间体与碱摩尔比为1:1;
所述反应温度为105℃,反应时间为12小时;
所述的方法B中,所述硒杂蒽酮中间体与D1硼酸原料或者D2硼酸原料的摩尔比为1:1~1:5,特别优选为1:1.5;
所述硒杂蒽酮中间体与催化剂摩尔比为1:0.01~1:0.2,特别优选为1:0.1;
所述硒杂蒽酮中间体与碱摩尔比为1:1;
所述反应温度为100℃,反应时间为12小时。
本发明还提供了一种基于硒杂蒽酮的有机发光材料在传感、成像、防伪标识、光催化、光存储或者有机电致发光器件等领域的应用。
本发明的有益效果是:
本发明提供了基于硒杂蒽酮的有机发光材料及其制备方法和应用。本发明利用硒原子的重原子效应促进单重态与三重态之间的系间窜越,能够提高三线态激子利用率,促进三线态激子辐射跃迁,有利于实现高效室温磷光发射。同时,以硒杂蒽酮为受体单元(A),常见供电子基团作为给体单元(D),形成D-A结构,能减小单线态与三线态之间的能级差,进一步促进S1-Tn之间的系间窜越,提高的三线态激子产率,从而增强磷光效率。该类材料能克服纯有机室温磷光材料在膜态条件下发光效率偏低的问题,实现在膜态下高的发光效率,在光学传感、电致发光器件、光催化、光存储、防伪标识和成像等领域具有应用前景。
附图说明
下面结合附图和具体实施方式对本发明作进一步详细说明。
图1为本发明实施实例1SeX-3-CP的常温吸收光谱;
图2为本发明实施实例1SeX-3-CP的常温稳态光谱;
图3为本发明实施实例1SeX-3-CP的低温磷光光谱;
图4为本发明实施实例1SeX-3-CP453 nm处的瞬态光谱;
图5为本发明实施实例1SeX-3-CP 500nm处的瞬态光谱;
图6为本发明实施实例1SeX-3-CP的氧气淬灭曲线;
图7为本发明实施实例1SeX-3-CP的氧气传感工作曲线。
具体实施方式
为了进一步理解本发明,下面结合实施例对本发明优选实施方案进行描述,但是应当理解,这些描述只是为进一步说明本发明的特征和优点,而不是对本发明权利要求的限制。
实施实例1:一种结构为SeX-3-CP基于硒杂蒽酮有机发光材料,合成路线如下:
(1)中间体SeX-3-Br的合成:在空气条件下,将间溴苯甲酸(1g,4.97mmol),二苯基二硒醚(3.12g,9.94mmol),[Ru(p-cymene)Cl2]2(130mg,0.20mmol),PCy3(112mg,0.4mmol),碳酸氢钠(420mg,4.97mmol),加入到40mL干燥的DMF中,随后在100℃反应48小时,反应颜色由橘黄色变为深红色最后转变为黑色。冷却至室温后,乙酸淬灭反应,使反应体系pH<7,倒入水中,乙酸乙酯萃取并使用饱和食盐水洗涤三次,有机层用无水硫酸钠干燥,除去乙酸乙酯并干燥获得黄褐色固体,随后将固体加入到含有20mL三氟甲磺酸的反应器中,在100℃下反应5小时。冷却至室温后,用水淬灭反应,二氯甲烷萃取,饱和食盐水洗涤三次后,分离出有机相并且用无水硫酸钠干燥,浓缩,硅胶柱分离获得黄色固体SeX-3-Br1.02 g,产率61%。MALDI-TOF MS(m/z):337.9[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3,25℃,TMS)δ8.78(d,J=2.3Hz,1H),8.65(dd,J=8.1,1.4Hz,1H),7.67–7.62(m,2H),7.57(td,J=7.6,1.5Hz,1H),7.53(d,J=8.4Hz,1H),7.51–7.47(m,1H).
(2)化合物SeX-3-CP的合成:在氩气氛围下,将SeX-3-Br(500mg,1.48mmol),N-苯基-9H-咔唑-3-硼酸(637mg,2.22mol),Pd(PPh3)4(85.5mg,0.074mmol),2mol/L的碳酸钾水溶液(5mL),Aliquant-336(2滴)加入到干燥的甲苯(25mL)中,在100℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-3-CP黄色固体460mg,产率62%。MALDI-TOF MS(m/z):501.1[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3,25℃,TMS)δ9.04(d,J=2.1Hz,1H),8.71(dd,J=8.0,1.5Hz,1H),8.48(d,J=1.6Hz,1H),8.23(d,J=7.8Hz,1H),7.95(dd,J=8.2,2.2Hz,1H),7.78–7.74(m,2H),7.68(dd,J=7.8,0.7Hz,1H),7.64(dd,J=10.2,5.1Hz,2H),7.61(dd,J=5.3,3.1Hz,2H),7.57(td,J=7.6,1.5Hz,1H),7.53–7.48(m,3H),7.44(dd,J=4.0,1.5Hz,2H),7.34(ddd,J=7.9,5.3,2.8Hz,1H).
实施实例2:一种结构为SeX-DMAC基于硒杂蒽酮有机发光材料,合成路线如下:
在氩气氛围下,SeX-3-Br(500mg,1.48mmol),9,10-二氢-9,9-二甲基吖啶(342mg,1.64mmol),Pd2dba3(131mg,0.15mmol),PtBuHBF4(131mg,0.45mmol),NaOtBu(128mg,1.34mmol)加入到30mL干燥甲苯溶液中在110℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-DMAC 481.9mg,产率73%。MALDI-TOF MS(m/z):446.5[M]+。
实施实例3一种结构为SeX-PTZ基于硒杂蒽酮有机发光材料,合成路线如下:
在氩气氛围下,SeX-3-Br(500mg,1.48mmol),吩噻嗪(326mg,1.64mmol),Pd2dba3(131mg,0.15mmol),PtBuHBF4(131mg,0.45mmol),NaOtBu(128mg,1.34mmol)加入到30mL干燥甲苯溶液中在110℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-PTZ 445.8mg,产率66%。质谱分析MALDI-TOF MS(m/z):456.3[M]+。
实施实例4:一种结构为SeX-Pxz基于硒杂蒽酮有机发光材料,合成路线如下:
在氩气氛围下,SeX-3-Br(500mg,1.48mmol),吩恶嗪(300mg,1.64mmol),Pd2dba3(131mg,0.15mmol),PtBuHBF4(131mg,0.45mmol),NaOtBu(128mg,1.34mmol)加入到30mL干燥甲苯溶液中在110℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-Pxz 397.2mg,产率61%。MALDI-TOF MS(m/z):440.4[M]+。
实施实例5:一种结构为SeX-2-CP基于硒杂蒽酮有机发光材料,合成路线如下:
(1)中间体SeX-2-Br的合成:在空气条件下,将对溴苯甲酸(1g,4.97mmol),二苯基二硒醚(3.12g,9.94mmol),[Ru(p-cymene)Cl2]2(130mg,0.20mmol),PCy3(112mg,0.4mmol),碳酸氢钠(420mg,4.97mmol),加入到40mL干燥的DMF中,随后在100℃反应48小时,反应颜色由橘黄色变为深红色最后转变为黑色。冷却至室温后,乙酸淬灭反应,使反应体系pH<7,倒入水中,乙酸乙酯萃取并使用饱和食盐水洗涤三次,有机层用无水硫酸钠干燥,除去乙酸乙酯并干燥获得黄褐色固体,随后将固体加入到含有20mL三氟甲磺酸的反应器中,在100℃下反应5小时。冷却至室温后,用水淬灭反应,二氯甲烷萃取,饱和食盐水洗涤三次后,分离出有机相并且用无水硫酸钠干燥,浓缩,硅胶柱分离获得黄色固体SeX-2-Br 836mg,产率50%。MALDI-TOF MS(m/z):337.9[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3)δ8.63(dd,J=8.1,1.5Hz,1H),8.49(d,J=8.7Hz,1H),7.81(d,J=1.9Hz,1H),7.64–7.60(m,1H),7.57(s,2H),7.51–7.46(m,1H).
(2)化合物SeX-2-CP的合成:在氩气氛围下,将SeX-2-Br(500mg,1.48mmol),N-苯基-9H-咔唑-3-硼酸(637mg,2.22mol),Pd(PPh3)4(85.5mg,0.074mmol),2mol/L的碳酸钾水溶液(5mL),Aliquant-336(2滴)加入到干燥的甲苯(25mL)中,在100℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-2-CP淡黄色固体519mg,产率70%。MALDI-TOF MS(m/z):501.1[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3)δ8.75(d,J=8.4Hz,1H),8.69(dd,J=8.0,1.5Hz,1H),8.46(d,J=1.6Hz,1H),8.23(d,J=7.7Hz,1H),7.97(d,J=1.7Hz,1H),7.86–7.83(m,1H),7.73(d,J=1.8Hz,1H),7.69–7.62(m,3H),7.60(t,J=4.2Hz,2H),7.56(td,J=7.5,1.6Hz,1H),7.53–7.42(m,5H),7.35(ddd,J=7.9,6.4,1.8Hz,1H).
实施实例6:一种结构为SeX-3-2CP基于硒杂蒽酮有机发光材料,合成路线如下:
(1)中间体SeX-3-2Br的合成:在空气条件下,将间溴苯甲酸(1g,2.96mmol),1,2-二(4-溴苯基)二硒醚(2.78g,5.92mmol),[Ru(p-cymene)Cl2]2(130mg,0.20mmol),PCy3(112mg,0.4mmol),碳酸氢钠(420mg,4.97mmol),加入到40mL干燥的DMF中,随后在100℃反应48小时,反应颜色由橘黄色变为深红色最后转变为黑色。冷却至室温后,乙酸淬灭反应,使反应体系pH<7,倒入水中,乙酸乙酯萃取并使用饱和食盐水洗涤三次,有机层用无水硫酸钠干燥,除去乙酸乙酯并干燥获得黄褐色固体,随后将固体加入到含有20mL三氟甲磺酸的反应器中,在100℃下反应5小时。冷却至室温后,用水淬灭反应,二氯甲烷萃取,饱和食盐水洗涤三次后,分离出有机相并且用无水硫酸钠干燥,浓缩,硅胶柱分离获得黄色固体SeX-3-2Br 1.18g,产率57%。MALDI-TOF MS(m/z):417.8[M]+。核磁共振氢谱分析:1H NMR(400MHz,CDCl3)δ8.78(d,J=2.2Hz,2H),7.68(d,J=2.2Hz,2H),7.66(d,J=2.2Hz,1H),7.53(d,J=8.4Hz,2H)。
(2)化合物SeX-3-2CP的合成:在氩气氛围下,将SeX-3-2Br(500mg,1.2mmol),N-苯基-9H-咔唑-3-硼酸(1.03g,3.9mol),Pd(PPh3)4(69.3mg,0.06mmol),2mol/L的碳酸钾水溶液(5mL),Aliquant-336(2滴)加入到干燥的甲苯(25mL)中,在100℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-3-2CP淡黄色固体507mg,产率57%。MALDI-TOF MS(m/z):742.2[M]+。核磁共振氢谱分析:1H NMR(400MHz,CDCl3)δ9.09(s,2H),8.51(s,2H),8.25(d,J=7.9Hz,2H),7.98(d,J=8.3Hz,2H),7.83–7.76(m,4H),7.64(q,J=7.6Hz,8H),7.52(d,J=8.9Hz,4H),7.45(s,4H),7.35(s,2H).
实施实例7:一种结构为SeX-2,3-2CP基于硒杂蒽酮有机发光材料,合成路线如下:
(1)中间体SeX-2,3-2Br的合成:在空气条件下,将3,4-二溴苯甲酸(1g,2.96mmol),1,2-二(4-溴苯基)二硒醚(2.78g,5.92mmol),[Ru(p-cymene)Cl2]2(130mg,0.20mmol),PCy3(112mg,0.4mmol),碳酸氢钠(420mg,4.97mmol),加入到40mL干燥的DMF中,随后在100℃反应48小时,反应颜色由橘黄色变为深红色最后转变为黑色。冷却至室温后,乙酸淬灭反应,使反应体系pH<7,倒入水中,乙酸乙酯萃取并使用饱和食盐水洗涤三次,有机层用无水硫酸钠干燥,除去乙酸乙酯并干燥获得黄褐色固体,随后将固体加入到含有20mL三氟甲磺酸的反应器中,在100℃下反应5小时。冷却至室温后,用水淬灭反应,二氯甲烷萃取,饱和食盐水洗涤三次后,分离出有机相并且用无水硫酸钠干燥,浓缩,硅胶柱分离获得黄色固体SeX-2,3-2Br 1.06g,产率57%。MALDI-TOF MS(m/z):417.8[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3)δ8.97(s,1H),8.76(dd,J=7.9,1.5Hz,1H),8.34(s,1H),8.15(dd,J=7.9,1.5Hz,1H),7.61(td,J=7.5,1.5Hz,1H),7.50(td,J=7.6,1.5Hz,1H).
(2)化合物SeX-2,3-2CP的合成:在氩气氛围下,将SeX-2,3-2Br(500mg,1.2mmol),N-苯基-9氢-咔唑-3-硼酸(1.03g,3.9mol),Pd(PPh3)4(69.3mg,0.06mmol),2mol/L的碳酸钾水溶液(5mL),Aliquant-336(2滴)加入到干燥的甲苯(25mL)中,在100℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-2,3-2CP淡黄色固体500mg,产率57%。MALDI-TOF MS(m/z):742.2[M]+。核磁共振氢谱分析:1H NMR(500MHz,CDCl3)δ8.79(s,1H),8.62(dd,J=7.8,1.6Hz,1H),8.38(s,1H),8.20–8.10(m,2H),8.01(d,J=1.7Hz,1H),8.00–7.91(m,3H),7.78(d,J=8.4Hz,1H),7.66–7.56(m,4H),7.55–7.45(m,9H),7.43–7.25(m,7H).
实施实例8:一种结构为SeX-AC-Cz基于硒杂蒽酮有机发光材料,合成路线如下:
(1)中间体SeX-Cl-Br的合成:在空气条件下,将间氯苯甲酸(1g,3.41mmol),1,2-二(4-溴苯基)二硒醚(3.2g,6.82mmol),[Ru(p-cymene)Cl2]2(130mg,0.20mmol),PCy3(112mg,0.4mmol),碳酸氢钠(420mg,4.97mmol),加入到40mL干燥的DMF中,随后在100℃反应48小时,反应颜色由橘黄色变为深红色最后转变为黑色。冷却至室温后,乙酸淬灭反应,使反应体系pH<7,倒入水中,乙酸乙酯萃取并使用饱和食盐水洗涤三次,有机层用无水硫酸钠干燥,除去乙酸乙酯并干燥获得黄褐色固体,随后将固体加入到含有20mL三氟甲磺酸的反应器中,在100℃下反应5小时。冷却至室温后,用水淬灭反应,二氯甲烷萃取,饱和食盐水洗涤三次后,分离出有机相并且用无水硫酸钠干燥,浓缩,硅胶柱分离获得黄色固体SeX-Cl-Br730 mg,产率57%。MALDI-TOF MS(m/z):372.5[M]+。
(2)中间体SeX-Cl-Cz的合成:在氩气氛围下,SeX-Cl-Br(1g,2.68mmol),9氢-咔唑(358mg 2.14mmol),Pd2dba3(247mg,0.27mmol),PtBuHBF4(241mg,0.81mmol),NaOtBu(257mg,2.68mmol)加入到35mL干燥甲苯溶液中在110℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到中间体SeX-Cl-Cz706mg,产率72%。MALDI-TOF MS(m/z):458.8[M]+。
(3)化合物SeX-AC-Cz的合成:在氩气氛围下,SeX-Cl-Cz(500mg,1.09mmol),9,10-二氢-9,9-二甲基吖啶(342mg,1.64mmol),Pd2dba3(123mg,0.11mmol),PtBuHBF4(120mg,0.41mmol),NaOtBu(128mg,1.34mmol)加入到30mL干燥甲苯溶液中在110℃下反应12h。冷却至室温后,反应液加入二氯甲烷稀释,并用饱和食盐水洗涤,分离出有机相并用无水硫酸钠干燥,浓缩,硅胶柱分离得到SeX-AC-Cz337 mg,产率49%。MALDI-TOF MS(m/z):631.6[M]+。
对本发明实施例1制备的纯有机室温磷光材料光物理性质进行检测。参见表1,表1为本发明实施例1制备的纯有机室温磷光材料光物理性质;参见图1-5,图1-5为本发明实施例1基于硒杂蒽酮发光材料的掺杂膜态光谱图。
表1
由表1,本发明提供的基于硒杂蒽酮发光材料在掺杂膜条件下具有磷光发射和较高的磷光发光效率(44.3%)。
实施实例9
将实例1所制备的磷光化合物SeX-3-CP以5wt%掺杂到聚苯乙烯(PS)中制备成薄膜型传感器,将该传感器至于真空石英瓶中,通过流量阀控制氧气与氮气的流速制备一系列不同氧气浓度的气体。随后,将不同浓度的气体导入中控石英瓶中,稳定2分钟,使用360nm光源激发,测量其在380~630nm的发射光谱(图6),与真空条件下的光谱相比,氧气浓度的上升,SeX-3-CP发生了光强猝灭,表明氧气对SeX-3-CP具有较好的发光淬灭。
根据Stern-Volmer方程计算淬灭常数(图7),Stern-Volmer方程如下I0/I=KSV[Q]+1,式中[Q]为氧气浓度,KSV为Stern-Volmer淬灭常数,根据计算上述工作曲线斜率得到淬灭常数为KSV=1.27×10-4ppm-1。通过图5获得SeX-3-CP的薄膜氧气传感器具有0-2.1×104ppm(0-21%)宽线性检测范围与4.9ppm低检测限,是优良的氧气传感器。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (7)
1.一种基于硒杂蒽酮的有机发光材料,其特征在于,其选自下述结构之一:
2.一种权利要求1所述的基于硒杂蒽酮的有机发光材料的制备方法,其特征在于,包括以下步骤:
步骤I:硒杂蒽酮中间体的制备
第一步:在空气条件下,苯甲酸或者苯甲酸衍生物,二苯基二硒醚或者二苯基二硒醚衍生物,催化剂,配体,碱和有机溶剂在反应瓶中混合,加热90℃~120℃,反应20~60小时,冷却至室温后,加入醋酸酸化,乙酸乙酯萃取,饱和食盐水洗涤三次,除去溶剂后,获得中间体粗产物后,无需分离;
第二步:将步骤一获得的中间体粗产物直接和酸混合后,进一步加热至90℃~120℃,反应1~12小时,反应结束后冷却至室温,乙酸乙酯萃取,饱和食盐水洗涤,除去溶剂,快速柱层析,获得硒杂蒽酮中间体,并且硒杂蒽酮中间体中最少存在一个卤素取代基;
所述的苯甲酸衍生物为单卤代苯甲酸或者多卤代苯甲酸,并且卤代位点为苯环上任意可取代位置;
所述的二苯基二硒醚衍生物为单卤代二苯基二硒醚或者多卤代二苯基二硒醚,并且卤代位点为苯环上任意可取代位置;
步骤II:
当硒杂蒽酮中间体与D1、D2均通过C-N键相连时,通过Buchwald偶联反应合成,即方法A,具体步骤为:
在惰性气氛下,将硒杂蒽酮中间体,与D1芳胺原料、或者分别与D1、D2芳胺原料,催化剂,配体,碱和有机溶剂混合后,加热至90℃~120℃,反应时间为5~36小时,得到权利要求1所示的基于硒杂蒽酮的有机发光材料;
当硒杂蒽酮中间体与D1、D2均通过C-C键相连时,通过Suzuki偶联反应合成,即方法B,具体步骤为:
在惰性气氛下,将硒杂蒽酮中间体,与D1硼酸原料,或者分别与D1、D2硼酸原料,催化剂,碱和有机溶剂混合后,加热至90℃~120℃,反应时间为5~36小时,得到权利要求1所示的基于硒杂蒽酮的有机发光材料;
步骤I第一步中,所述的催化剂为二氯双(4-甲基异丙基苯基)钌(II);所述的配体为三环己基膦或者三环己基氧膦;所述的碱为碳酸钾、碳酸钠、碳酸氢钾、磷酸钾或者碳酸氢钠;所述的有机溶剂为1,4-二氧六环、四氢呋喃、甲苯、N,N-二甲基乙酰胺或者N,N-二甲基甲酰胺;步骤I第二步中,所述的酸为浓硫酸或者三氟甲磺酸;
其中,D1、D2分别与权利要求1中各化合物上的取代基团相对应。
3.根据权利要求2所述的基于硒杂蒽酮的有机发光材料的制备方法,其特征在于,所述苯甲酸或者苯甲酸衍生物与二苯基二硒醚或者二苯基二硒醚衍生物的摩尔比为1:1~1:10;
所述苯甲酸或者苯甲酸衍生物、催化剂、配体的摩尔比为1:0.01:0.01~1:0.1:0.1;
所述苯甲酸或者苯甲酸衍生物与碱的摩尔比为1:1;
所述苯甲酸或者苯甲酸衍生物与酸的比例为1g:5mL~1g:50mL。
4.根据权利要求2所述的基于硒杂蒽酮的有机发光材料的制备方法,其特征在于,步骤I中,所述第一步加热反应温度为105℃,时间为36小时;所述第二步加热反应温度为100℃,时间为5小时。
5.根据权利要求2所述的基于硒杂蒽酮的有机发光材料的制备方法,其特征在于,步骤II中,所述方法A中,催化剂为三(二亚苄基丙酮)二钯或者醋酸钯;碱为碳酸铯、叔丁醇钾或者叔丁醇钠;配体为(±)-2,2'-双-(二苯膦基)-1,1'-联萘、三叔丁基膦、三(邻甲基苯基)膦或者4,5-双二苯基膦-9,9-二甲基氧杂蒽;有机溶剂为二氧六环、甲苯或者二甲苯;
所述方法B中,催化剂为四(三苯基膦)钯、双(三苯基膦)二氯化钯(II)、[1,1'-双(二苯基膦基)二茂铁]二氯化钯、1,4-双(二苯基膦丁烷)二氯化钯、双(2-甲基烯丙基)氯化钯、氯化钯、碘化钯或者三二亚苄基丙酮二钯;碱为碳酸钠、碳酸钾、磷酸钾、叔丁醇钠或者碳酸铯;有机溶剂为二甲基亚砜、N,N-二甲基甲酰胺、二氧六环、甲苯或者二甲苯。
6.根据权利要求2所述的基于硒杂蒽酮的有机发光材料的制备方法,其特征在于,步骤II中,所述的方法A中,硒杂蒽酮中间体与D1芳胺原料或者D2芳胺原料的摩尔比为1:1~1:5;
所述硒杂蒽酮中间体与催化剂摩尔比为1:0.01~1:0.2;
所述催化剂与配体的摩尔比为1:1~1:3;
所述硒杂蒽酮中间体与碱摩尔比为1:1;
所述反应温度为105℃,反应时间为12小时;
所述的方法B中,所述硒杂蒽酮中间体与D1硼酸原料或者D2硼酸原料的摩尔比为1:1~1:5;
所述硒杂蒽酮中间体与催化剂摩尔比为1:0.01~1:0.2;
所述硒杂蒽酮中间体与碱摩尔比为1:1;
所述反应温度为100℃,反应时间为12小时。
7.一种权利要求1所述的基于硒杂蒽酮的有机发光材料在光学传感、成像、防伪标识、光催化、光存储或者有机电致发光器件领域中的应用。
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