CN103936791A - Series organic electrophosphorescent material - Google Patents
Series organic electrophosphorescent material Download PDFInfo
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- CN103936791A CN103936791A CN201310682719.3A CN201310682719A CN103936791A CN 103936791 A CN103936791 A CN 103936791A CN 201310682719 A CN201310682719 A CN 201310682719A CN 103936791 A CN103936791 A CN 103936791A
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- 239000000463 material Substances 0.000 title claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- -1 4,5-disubstituted phenanthrene Chemical class 0.000 claims abstract description 36
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 31
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 9
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 5
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002322 conducting polymer Substances 0.000 claims description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 239000010931 gold Substances 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 4
- 239000011147 inorganic material Substances 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 229920001447 polyvinyl benzene Polymers 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 abstract description 10
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GVUGQJWAXYSFPE-UHFFFAOYSA-N 2-(2-carboxy-6-fluorophenyl)-3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1C1=C(F)C=CC=C1C(O)=O GVUGQJWAXYSFPE-UHFFFAOYSA-N 0.000 description 4
- IPDAAGWNRONPEN-UHFFFAOYSA-N 4,5-difluoro-9,10-dihydrophenanthrene Chemical compound C1CC2=CC=CC(F)=C2C2=C1C=CC=C2F IPDAAGWNRONPEN-UHFFFAOYSA-N 0.000 description 4
- 0 CCC1(C)c(c2c(c(*)c3C=*)-c4c(*)c(C)ccc4CC2)c3-c2cc*c*2C1=C Chemical compound CCC1(C)c(c2c(c(*)c3C=*)-c4c(*)c(C)ccc4CC2)c3-c2cc*c*2C1=C 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 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
- 239000003054 catalyst Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- NCOFQZRLIYPMNJ-UHFFFAOYSA-N 3-ethoxy-4-phenylmethoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 NCOFQZRLIYPMNJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910020427 K2PtCl4 Inorganic materials 0.000 description 1
- KUHAYJJXXGBYBW-UHFFFAOYSA-N Nc(c(F)ccc1)c1C(O)=O Chemical compound Nc(c(F)ccc1)c1C(O)=O KUHAYJJXXGBYBW-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
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- 238000005424 photoluminescence Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- HQYNSFAFYFMRLG-UHFFFAOYSA-N tribromo phosphite Chemical compound BrOP(OBr)OBr HQYNSFAFYFMRLG-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a series organic electrophosphorescent material. A structural general formula of the electrophosphorescent material is shown as a formula I. The complex electrophosphorescent luminescent material takes 4,5-disubstituted phenanthrene and 4,5-disubstituted 9, 10-dihydrophenanthrene as a main body. Due to influence of electron donating group with 4,5-two large steric hindrance, fixing effect of phenanthrene and 9,10- dihydrophenanthrene hydrocarbon chain, the capture capability to exciton is greatly increased, phosphorescence life can be effectively shortened, the luminescence efficiency is increased, and the luminescent device performance is increased. The compound has excellent film forming ability and high luminescence efficiency.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent display, and relates to a series of organic electrophosphorescent materials.
Background
For organic electroluminescence (abbreviated as OLED) and related research, the electroluminescence phenomenon of organic compound single crystal anthracene was first discovered by pope et al in 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display realization and the like, and can be widely applied to flat panel displays and surface light sources, thereby being widely researched, developed and used.
Organic electroluminescent materials fall into two broad categories: organic electroluminescent materials and organic electrophosphorescent materials, in which organic electroluminescence is a result of radiative deactivation of singlet excitons, unlike photoluminescence, during which triplet excitons and singlet excitons are simultaneously generated. The generation ratio of singlet excitons and triplet excitons is generally 1: 3, according to the forbidden effect of quantum forbidden meter, the triplet exciton mainly generates non-radiative decay, has little contribution to luminescence, and only the singlet exciton radiates luminescence, therefore, for the organic/polymer electroluminescent device, the fundamental reason that the luminescence efficiency is difficult to improve is that the luminescence process is the luminescence of the singlet exciton.
In the early stage of organic light emitting device research, people put forward the assumption of triplet state luminescence, and the Forrest group made red electrophosphorescent light emitting devices by doping octaethylporphyrin platinum in a small molecular host material of octahydroxyquinoline aluminum, so that the external quantum efficiency reaches 4%, so far, the research of electrophosphorescence started to get great attention from academia, and the research of organic electrophosphorescence in the following years is rapidly developed. The iridium complex is a phosphorescent material which is developed most and has the best application prospect due to the short triplet state service life and the good luminescent performance, and the phosphorescent material has stronger triplet state quenching in a solid, so that generally the iridium complex is used as a doping object material, a material with a wider band gap is used as a doping host material, and high luminescent efficiency is obtained by energy transfer or direct exciton trapping on an object for luminescence.
Organic electroluminescent green phosphorescent materials are the earliest studied and the most mature materials. Hino et al in 2004 made phosphorescent devices by spin coating, the external quantum efficiency was at most 29cd/A, and the high efficiency achieved by this simple device structure was attributable to the good film-forming properties of the material and the energy transfer from host to guest material. Adachi et al will (ppy)2Ir (acac) is doped into TAZ, HMTPD is used as a hole transport layer, a green device with the maximum external quantum efficiency of 20% and the energy efficiency of 65lm/W is obtained, the internal quantum efficiency is almost close to 100% through calculation, and the triplet excitons and the singlet excitons are simultaneously utilized.
Disclosure of Invention
The invention aims to provide a series of organic electrophosphorescent materials.
The organic electrophosphorescent material has a structural general formula shown in formula I,
in the formula I, R1、R4And R5All selected from any one of hydrogen atom, fluorine atom, methoxyl, cyano, trifluoromethoxy, aliphatic hydrocarbon group of C1-C50, aromatic group of C1-C50 and condensed ring aromatic group of C1-C50;
R2any one selected from a hydrogen atom, a fluorine atom, a trifluoromethyl group, a methoxy group, a methyl group and a C1-C50 aliphatic hydrocarbon group;
m is an iridium or platinum atom;
z is-CH2CH2-or-CH = CH-;
x is 1, 2 or 3;
when X is 1 or 2, R6Is acetylacetone group, C1-C50 aliphatic alkyl substituted acetoacetyl group, 2-pyridine formyloxy group or substituted 2-pyridine formyloxy group; in the 2-pyridine formyloxy containing the substituent, the substituent is selected from any one of fluorine atoms, C1-C10 alkyl, cyano and trifluoromethyl;
when X is 3, R6Is selected from 2- (8-R)5-6-R3-4,5-2R2-3-R1-7-R4Phenanthrene) pyridyl or 2- (8-R)5-6-R3-4,5-2R2-3-R1-7-R4-9, 10-dihydrophenanthren-2-yl) pyridyl, wherein R1、R4And R5All selected from any one of hydrogen atom, fluorine atom, methoxyl, cyano, trifluoromethoxy, aliphatic hydrocarbon group of C1-C50, aromatic group of C1-C50 and condensed ring aromatic group of C1-C50; r2Any one selected from a hydrogen atom, a fluorine atom, a trifluoromethyl group, a methoxy group, a methyl group and a C1-C50 aliphatic hydrocarbon group;
specifically, the compound shown in the formula I is any one of the compounds shown in the formula I-1a, the formula I-1b, the formula I-2a, the formula I-2b and the formula I-3:
the formula I-1a is specifically a compound shown as PHPT-AC-I:
the formula I-2a is specifically a compound shown as PHIR-AC-I:
the formula I-2b is specifically a compound shown as PHIR-PY-I:
the formula I-3 is specifically a compound represented by PHIR-CJH-I:
in the formula I-1a, the formula I-1b, the formula I-2a, the formula I-2b, the formula I-3, the PHIR-AC-I, PHPT-AC-I, PHIR-PY-I and the PHIR-CJH-I, R1To R5Is defined in relation to R in formula I in claim 11To R5The definitions of (A) are the same;
the R is7Are each a hydrogen atom or an aliphatic hydrocarbon group of C1-C50;
the R is8Are all selected from any one of hydrogen atoms, fluorine atoms, alkyl groups of C1-C10, cyano groups and trifluoromethyl groups;
the PHIR-AC-I compound is more specifically any one of the following compounds:
the PHPT-AC-I compound is more specifically any one of the following compounds:
the compound represented by the PHIR-PY-I is more specifically any one of the following compounds:
the PHIR-CJH-I compound is more specifically any one of the following compounds:
in addition, the luminescent material containing the compound shown in the formula I provided by the invention and the application of the compound shown in the formula I in preparing the luminescent material also belong to the protection scope of the invention. The luminescent material is specifically an organic electrophosphorescent luminescent material, and more specifically an organic electrophosphorescent orange phosphorescent luminescent material; the luminescent material has a luminescent wavelength of 460-620nm, specifically 512, 518, 522, 524, 526, 533, 535, 542 or 512-542 nm.
The application of the compound shown in the formula I as a luminescent layer in preparing an organic electroluminescent device and the organic electroluminescent device containing the compound shown in the formula I as the luminescent layer also belong to the protection scope of the invention. The organic electroluminescent device is specifically an organic electroluminescent phosphorescent device, and more specifically an organic electroluminescent orange phosphorescent material; the luminescent material has a luminescent wavelength of 460-620nm, specifically 512, 518, 522, 524, 526, 533, 535, 542 or 512-542 nm.
Specifically, the organic electroluminescent device consists of a transparent substrate, an anode, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer from bottom to top in sequence;
wherein, the material for forming the transparent substrate is glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material for forming the hole injection layer is TDATA;
the structural formula of the TDATA is as follows:
the material constituting the hole transport layer is NPB;
the structural formula of the NPB is as follows:
the material for forming the organic light-emitting layer is a compound shown in a formula I and a host material;
wherein the host material is mCP, CBP, NATZ or
Wherein the structural formulas of mCP, CBP and NATZ are as follows:
the mass of the compound shown in the formula I is 1-10% of that of the main material, specifically 5%;
the material for forming the electron transport layer is Alq3, Gaq3 or BPhen;
wherein the structural formulas of Alq3, Gaq3, BPhen and TPBi are as follows in sequence:
the cathode layer is made of a material selected from any one or two of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
Specifically, the thickness of the hole injection layer is 30-50nm, specifically 40 nm;
the thickness of the hole transport layer is 5-15nm, specifically 10 nm;
the thickness of the organic light-emitting layer is 10-100nm, specifically 50 nm;
the thickness of the electron transmission layer is 10-30nm, specifically 20 nm;
the thickness of the cathode layer is 90-110nm, specifically 100 nm.
The complex electrophosphorescent luminescent material with phenanthrene and 9, 10-dihydrophenanthrene structures provided by the invention takes 4, 5-disubstituted phenanthrene and 4, 5-disubstituted 9, 10-dihydrophenanthrene as main bodies. Due to the influence of electron donor groups with two large steric hindrance at the 4, 5-position and the fixation effect of phenanthrene and 9, 10-dihydrophenanthrene hydrocarbon chains, the capture capacity of excitons is greatly improved, the phosphorescence life is effectively shortened, the luminous efficiency is improved, and the performance of a luminescent device is improved.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
The compound shown in the formula I provided by the invention can be prepared according to the following reaction formula:
the following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED device performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
The following abbreviations are used in the examples:
EXAMPLE 1 preparation of the Compound PHIR-AC-005
The first step is as follows: preparation of 6,6 '-difluorobiphenyl-2, 2' -dicarboxylic acid
75g of copper sulfate pentahydrate are dissolved in 300ml of water, 230ml of 25% ammonia water are added with stirring, and the temperature is reduced to 0 ℃ by an ice salt bath. An aqueous solution of 20.8g of hydroxylamine hydrochloride and 12.8g of sodium hydroxide was slowly added dropwise to the cold copper solution and kept below 0 ℃ for further use.
31g of 2-amino-3-fluorobenzoic acid and 85ml of concentrated hydrochloric acid are mixed, 300ml of water and 60ml of acetonitrile are added, the temperature is reduced to below 0 ℃ by using a salt-freezing bath, 15.9g of a solution of sodium nitrite dissolved in 120ml of water is slowly dripped into the solution, the solution is stirred and reacted for 1 hour at the temperature below 5 ℃, and the clear diazo solution is slowly dripped into the copper solution for standby, and the process is kept below 10 ℃. Stirring and reacting for 1 hour at room temperature, heating to 85 ℃, dropwise adding concentrated hydrochloric acid for acidification, cooling to 0 ℃ in an ice water bath, filtering out insoluble solid, washing a filter cake with water, and drying in vacuum to obtain 30.5g of 6,6 '-difluorobiphenyl-2, 2' -dicarboxylic acid as white solid.
The second step is that: preparation of methyl 6,6 '-difluorobiphenyl-2, 2' -dicarboxylate
30g of 6,6 '-difluorobiphenyl-2, 2' -dicarboxylic acid and 600ml of anhydrous methanol are mixed, heated to reflux, 10ml of thionyl chloride is slowly added dropwise, the reflux reaction is carried out overnight, the clear solution is obtained, the solution is concentrated under reduced pressure and dried, the residue is separated and purified by a silica gel column and eluted by ethyl acetate and petroleum ether, and 29g of 6,6 '-difluorobiphenyl-2, 2' -dicarboxylic acid methyl ester is obtained and is white crystals.
The third step: preparation of (6,6 '-difluorobiphenyl-2, 2' -yl) dimethanol
15g of methyl 6,6 '-difluorobiphenyl-2, 2' -dicarboxylate was dissolved in 400ml of dry THF, the clear solution was cooled to-5 ℃ in an ice salt bath, 5.6g of lithium aluminum hydride was added in portions slowly, the mixture was stirred at constant temperature for 1 hour, slowly warmed to room temperature, stirred for 12 hours, water and 17ml of a 15% aqueous sodium hydroxide solution were added dropwise to the reaction mixture to quench the reaction, the reaction mixture was filtered, the filter cake was washed with THF, the filtrate was concentrated under reduced pressure to dryness, and the residue was separated and purified by a silica gel column to give 10g of (6,6 '-difluorobiphenyl-2, 2' -yl) dimethanol as white crystals.
The fourth step: preparation of 2,2 '-bis (bromomethyl) -6, 6' -difluorobiphenyl
10.7g of (6,6 '-difluorobiphenyl-2, 2' -yl) dimethanol was dissolved in 250ml of chloroform, 49g of tribromooxyphosphorus was slowly added in portions, the reaction was refluxed for 10 hours at elevated temperature, cooled to room temperature, washed three times with saturated brine, the collected organic phase was dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure to dryness, and the residue was separated and purified by a silica gel column to give 14.5g of 2,2 '-bis (bromomethyl) -6, 6' -difluorobiphenyl as a yellow oil.
The fifth step: preparation of 4, 5-difluoro-9, 10-dihydrophenanthrene
6.16g of 2,2 '-bis (bromomethyl) -6, 6' -difluorobiphenyl were dissolved in 250ml of anhydrous diethyl ether and 0.7g was added under nitrogen protectionHeating magnesium powder and iodine, reflux-reacting for 1 hr under ultrasound till magnesium powder disappears, cooling to room temperature, adding small amount of water, separating ether phase, washing with saturated salt water, and collecting organic phase with anhydrous MgSO4Drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying the residue with silica gel column to obtain 1.0g of 4, 5-difluoro-9, 10-dihydrophenanthrene as white solid.
And a sixth step: preparation of 2-bromo-4, 5-difluoro-9, 10-dihydrophenanthrene
Dissolving 2.16g of 4, 5-difluoro-9, 10-dihydrophenanthrene in 150ml of chloroform, adding 16.2mg of anhydrous ferric chloride, heating to reflux, slowly dropwise adding a solution of 1.95g of bromine in 20ml of chloroform, continuing reflux reaction for 24 hours, cooling to room temperature, washing with saturated aqueous sodium bisulfite for three times, drying the collected organic phase with anhydrous sodium sulfate, filtering, concentrating the filtrate under reduced pressure to dryness, and decoloring the residue with a short silica gel column to obtain a mixture of 2-bromo-4, 5-difluoro-9, 10-dihydrophenanthrene and 4, 5-difluoro-9, 10-dihydrophenanthrene, which cannot be separated and purified, wherein the GC content of the product is 79 percent, and the yellow oily substance.
The seventh step: preparation of 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) -boronic acid pinacol ester
2.8g of the mixture of 2-bromo-4, 5-difluoro-9, 10-dihydrophenanthrene obtained in the sixth step, 2.1g of pinacol diboron, 1.1g of anhydrous potassium acetate, 61mg of Pd (dppf) Cl2Heating DCM palladium catalyst and 50ml N, N-dimethylformamide to 85 deg.C, stirring for 8 hr, cooling to room temperature, pouring into ice water, extracting with ethyl acetate, washing organic phase with saturated saline three times, collecting organic phaseThe organic phase is dried over anhydrous sodium sulfate, filtered, the filtrate is concentrated to dryness under reduced pressure, and the residue is separated and purified by a silica gel column to give 2.46g of 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) -boronic acid pinacol ester as a white solid.
Eighth step: preparation of 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) pyridine
2.0g of the compound 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) -pinacol borate obtained in the seventh step were mixed with 1.3g of 2-bromopyridine, 2.5g of anhydrous sodium carbonate, 50ml of toluene, 20ml of ethanol and 20ml of water, and 65mg of Pd (PPh) as a catalyst was further added3)4Heating and refluxing for 12 hours under the protection of nitrogen, cooling to room temperature, separating an organic phase, extracting an aqueous phase by using ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying residues by using a silica gel column to obtain 1.5g of 2- (4, 5-difluoro-9, 10-dihydrophenanthrene-2-yl) pyridine which is a white solid.
The ninth step: preparation of Compound G-2
1.0g of the compound 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) pyridine and 573mg of IrCl3·3H2Dispersing O in 30ml of ethylene glycol ethyl ether and 10ml of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain 850mg of a compound G-2, namely a yellow solid.
The tenth step: preparation of compound PHIR-AC-005
800mg of compound G-2, 98mg of acetylacetone and 520mg of anhydrous sodium carbonate are dispersed in 40ml of ethylene glycol ethyl ether, the mixture is heated under reflux for 24 hours under the protection of nitrogen, the mixture is cooled to room temperature, the reaction solution is poured into water, DCM is used for extraction, an organic phase is dried and filtered, the filtrate is concentrated under reduced pressure to dryness, and the residue is separated and purified by a silica gel column to obtain 650mg of compound PHIR-AC-005 as a yellow solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.29-8.35(m,4H),8.14-8.21(m,4H),7.73-7.76(m,4H),7.63-7.69(m,2H),6.65-6.69(m,2H),5.01(s,1H),2.59-2.63(m,4H),2.83-2.90(m,4H),1.64(s,6H)。
(1) glass transition temperature (DSC): 268.71 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,335 nm;
(3) phosphorescent emission wavelength (DCM): 526nm
Example 2 preparation of the Compound PHIR-AC-006
The first step is as follows: preparation of Compound G-2
1.0g of the compound 2- (4, 5-bistrifluoromethyl-9, 10-dihydrophenanthren-2-yl) pyridine (cf. example 1, synthesis in the first to eight steps) and 427mg of IrCl3·3H2O is dispersed in 30ml of ethylene glycol ethyl ether and 10ml of water, and the mixture is heated and refluxed under the protection of nitrogenAfter 24 hours, it was cooled to room temperature, filtered, and the filter cake was washed with water and dried under vacuum to give 520mg of Compound G-2 as a yellow solid.
The second step is that: preparation of compound PHIR-AC-006
500mg of compound G-2, 62mg of acetylacetone and 262mg of anhydrous sodium carbonate are dispersed in 40ml of ethylene glycol ethyl ether, the mixture is heated under reflux for 24 hours under the protection of nitrogen, the mixture is cooled to room temperature, the reaction solution is poured into water, DCM is used for extraction, the organic phase is dried and filtered, the filtrate is concentrated under reduced pressure to dryness, and the residue is separated and purified by a silica gel column to obtain 300mg of compound PHIR-AC-006 as a yellow solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.27-8.34(m,4H),8.14-8.21(m,4H),7.73-7.76(m,4H),7.63-7.68(m,2H),6.64-6.68(m,2H),5.01(s,1H),2.59-2.63(m,4H),2.83-2.90(m,4H),1.66(s,6H)。
(1) glass transition temperature (DSC): 245.58 deg.C;
(2) UV maximum absorption wavelength (DCM): 255nm,305 nm;
(3) phosphorescent emission wavelength (DCM): 524nm
EXAMPLE 3 preparation of the Compound PHIR-AC-001
The first step is as follows: preparation of 2- (4, 5-difluorophenanthren-2-yl) pyridine
1.5g of 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) pyridine prepared in the eighth step of example 1 was dissolved in 100ml of benzene, 3.5g of DDQ was added, the mixture was heated under reflux for 3 days, cooled to room temperature, concentrated under reduced pressure to dryness, and the residue was separated and purified by a neutral alumina column to give 1.4g of 2- (4, 5-difluorophenanthren-2-yl) pyridine as a white solid.
The second step is that: preparation of Compound G-2
Referring to the ninth step of example 1, compound G-2 was prepared as a yellow solid by replacing 2- (4, 5-difluoro-9, 10-dihydrophenanthren-2-yl) pyridine with 2- (4, 5-difluorophenanthren-2-yl) pyridine.
The third step: preparation of compound PHIR-AC-001
Referring to the tenth step of example 1, the compound PHIR-AC-001 was obtained as a yellow solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.30-8.37(m,4H),8.14-8.22(m,4H),7.73-7.76(m,4H),7.63-7.69(m,2H),7.50(s,4H),6.64-6.68(m,2H),5.01(s,1H),1.64(s,6H)。
(1) glass transition temperature (DSC): 273.37 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,335 nm;
(3) phosphorescent emission wavelength (DCM): 522nm
EXAMPLE 4 preparation of the Compound PHIR-CJH-001
872mg of PHIR-AC-001 and 2.9g of 2- (4, 5-difluorophenanthren-2-yl) pyridine, the compound being prepared in the first step in example 2, were dispersed with 20ml of glycerin under stirring, the temperature was raised to 180 ℃ under nitrogen protection, the reaction was stirred for 8 hours, the temperature was cooled to room temperature, the reaction mixture was poured into 100ml of 1N diluted hydrochloric acid, suction filtration and washing of the cake with water were carried out, and the obtained solid was separated and purified by a silica gel column to obtain 450mg of PHIR-CJH-001 as a brown solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.31-8.36(m,6H),8.14-8.22(m,6H),7.73-7.76(m,6H),7.63-7.69(m,3H),7.51(s,6H),6.64-6.68(m,3H)。
(1) glass transition temperature (DSC): 288.56 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,315nm,335 nm;
(3) phosphorescent emission wavelength (DCM): 518nm
EXAMPLE 5 preparation of the Compound PHIR-PY-001
1.6G of the compound G-2 prepared in the second step of example 2, 707mg of 2-picolinic acid, 324mg of anhydrous potassium carbonate and 50ml of 1, 4-dioxane were reacted under reflux at elevated temperature for 8 hours, concentrated to dryness under reduced pressure, and the residue was separated and purified by a silica gel column to give 0.8G of the compound PHIR-PY-001 as a yellow solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.31-8.36(m,4H),8.14-8.22(m,6H),7.73-7.76(m,4H),7.63-7.69(m,4H),7.50(s,4H),7.26-7.34(m,2H)。
(1) glass transition temperature (DSC): 287.39 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,325nm and 355 nm;
(3) phosphorescent emission wavelength (DCM): 512nm
EXAMPLE 6 preparation of PHPT-AC-001 Compound
The first step is as follows: preparation of Compound G-2
2.0g of the compound 2- (4, 5-difluorophenanthren-2-yl) pyridine prepared in the first step in example 2 and 1.35g of K2PtCl4Dispersing in 60ml of ethylene glycol ethyl ether and 20ml of water, heating to 80 ℃ under the protection of nitrogen, stirring for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain 1.8G of a compound G-2, namely a brown solid.
The second step is that: preparation of compound PHPT-AC-001
And (2) dispersing the compound G-21.0G obtained in the step (1), 384mg of acetylacetone and 1G of anhydrous sodium carbonate in 20ml of ethylene glycol ethyl ether, heating to 100 ℃ under the protection of nitrogen, stirring for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water, dissolving with DCM, filtering, drying and filtering the filtrate, and concentrating the filtrate under reduced pressure to obtain 420mg of a compound PHPT-AC-001 which is a dark yellow solid.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.34(s,1H),8.14-8.22(m,2H),7.73-7.76(m,2H),7.63-7.69(m,2H),7.50(s,2H),6.68(s,1H),5.01(s,1H),1.64(s,6H)。
(1) glass transition temperature (DSC): 258.06 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,315nm,335 nm;
(3) phosphorescent emission wavelength (DCM): 533nm
Preparation of the Compound of example 7 PHPT-AC-006
Referring to example 6, compound PHPT-AC-006 was prepared as a brown solid by replacing 2- (4, 5-bistrifluoromethyl-9, 10-dihydrophenanthren-2-yl) pyridine with 2- (4, 5-bistrifluoromethyl-2, 10-dihydrophenanthren-2-yl) pyridine.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.36(s,1H),8.13-8.17(m,2H),7.72-7.76(m,2H),7.63-7.69(m,2H),6.77(s,1H),5.01(s,1H),2.59-2.63(m,2H),2.83-2.90(m,2H),1.66(s,6H)。
(1) glass transition temperature (DSC): 246.39 deg.C;
(2) UV maximum absorption wavelength (DCM): 255nm,305nm,325 nm;
(3) phosphorescent emission wavelength (DCM): 535nm
EXAMPLE 8 preparation of PHPT-AC-014 Compound
Referring to example 6, compound PHPT-AC-014 was prepared as a brown solid by replacing 2- (4, 5-difluorophenanthren-2-yl) pyridine with 2- (7-methyl-4, 5-bistrifluoromethyl-9, 10-dihydrophenanthren-2-yl) pyridine.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.27-8.34(m,2H),8.14(s,1H),7.73-7.76(m,2H),7.63-7.68(m,1H),6.64-6.68(m,1H),5.01(s,1H),2.59-2.63(m,2H),2.83-2.90(m,2H),2.63(s,3H),1.64(s,6H)。
(1) glass transition temperature (DSC): 242.52 deg.C;
(2) UV maximum absorption wavelength (DCM): 255nm,305nm,325 nm;
(3) phosphorescent emission wavelength (DCM): 532nm
Preparation of the Compound of example 9 PHPT-AC-016
Referring to example 6, compound PHPT-AC-016 was prepared as a brown solid by replacing 2- (4, 5-dimethoxy-7-methyl-9, 10-dihydrophenanthren-2-yl) pyridine with 2- (4, 5-dimethoxy-7-methyl-2, 10-dihydrophenanthren-2-yl) pyridine.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.32(s,1H),8.16-8.19(m,2H),7.73-7.76(m,2H),7.64(s,1H),6.92(s,1H),5.00(s,1H),2.59-2.64(m,2H),2.83-2.89(m,2H),2.64(s,3H),1.64(s,6H)。
(1) glass transition temperature (DSC): 358.05 deg.C;
(2) UV maximum absorption wavelength (DCM): 305nm,315nm and 325 nm;
(3) phosphorescent emission wavelength (DCM): 542nm
EXAMPLE 10 preparation of PHPT-AC-022 Compound
Referring to example 6, compound PHPT-AC-022 was prepared as a brown solid by replacing 2- (4, 5-difluorophenanthren-2-yl) pyridine with 2- (3, 6-difluoro-4, 5-bistrifluoromethyl-9, 10-dihydrophenanthren-2-yl) pyridine.
Experimental data:
1H NMR(CDCl3,300MHz):δ=8.34(s,1H),8.14-8.18(m,2H),7.73-7.76(m,2H),6.96(m,1H),5.00(s,1H),2.59-2.63(m,2H),2.84-2.89(m,2H),1.65(s,6H)。
(1) glass transition temperature (DSC): 242.95 deg.C;
(2) UV maximum absorption wavelength (DCM): 255nm,305nm,325 nm;
(3) phosphorescent emission wavelength (DCM): 526nm
Example 11 preparation of devices OLED-1, OLED-2, OLED-3
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, continuously and respectively evaporating a compound TDATA as a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
wherein, the structural formula of TDATA is as follows:
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
wherein the structural formula of NPB is as follows:
4) and continuously evaporating compounds PHIR-AC-001 and CBP shown in a layer type I on the hole transport layer to be used as an organic light emitting layer of the device, wherein the evaporation rate ratio of the compounds PHIR-AC-001 to CBP is 1: 100, the dosage of the compound PHIR-AC-001 is 5 percent of the mass of CBP, the evaporation rate is 0.1nm/s, and the thickness of an organic luminescent layer obtained by evaporation is 50 nm;
5) continuously evaporating a layer of Alq3 material on the organic light-emitting layer to be used as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
wherein the structural formula of Alq3 is as follows:
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: 9, obtaining the OLED-1 provided by the invention.
According to the same steps as the above, only replacing the PHIR-AC-001 used in the step 4) with the PHIR-AC-005 to obtain the OLED-2 provided by the invention;
according to the same steps as the above, only the PHIR-AC-001 used in the step 4) is replaced by the PHIR-AC-006, and the OLED-3 provided by the invention is obtained.
The results of the performance tests of the obtained devices OLED-1 to OLED-3 are shown in Table 1.
TABLE 1 Performance test results of OLED-1 to OLED-3
From the above, it can be seen that the organic light emitting device obtained by doping 5% of the compound represented by formula I has a current density exceeding 2100A/m2The power efficiency is as high as 6.92cd/A, and the light color is relatively pure green light.
EXAMPLE 12 preparation of devices OLED-4-OLED-8
Prepared according to the method of example 11, replacing only PHIR-AC-001 with PHPT-AC-001, PHPT-AC-006, PHPT-AC-014, PHPT-AC-016, and PHPT-AC-022 in this order to obtain devices OLED-4 to OLED-8.
The device properties are detailed in table 2:
TABLE 2 Performance test results of OLED-4 to OLED-8
From the above, the organic light emitting device obtained by doping 5% of the compound shown in formula I has higher current density, significantly improved power efficiency, and a relatively pure green light color.
Although the present invention has been described in connection with the preferred embodiments, it is not limited to the above-described embodiments, and it is to be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the present invention, and the scope of the present invention is outlined by the appended claims.
Claims (6)
1. A compound of the formula I, wherein,
in the formula I, R1、R4And R5All selected from any one of hydrogen atom, fluorine atom, methoxyl, cyano, trifluoromethoxy, aliphatic hydrocarbon group of C1-C50, aromatic group of C1-C50 and condensed ring aromatic group of C1-C50;
R2any one selected from a hydrogen atom, a fluorine atom, a trifluoromethyl group, a methoxy group, a methyl group and a C1-C50 aliphatic hydrocarbon group;
m is an iridium or platinum atom;
z is-CH2CH2-or-CH = CH-;
x is 1, 2 or 3;
when X is 1 or 2, R6Is acetylacetone group, C1-C50 aliphatic alkyl substituted acetoacetyl group, 2-pyridine formyloxy group or substituted 2-pyridine formyloxy group; in the 2-pyridine formyloxy containing the substituent, the substituent is selected from any one of fluorine atoms, C1-C10 alkyl, cyano and trifluoromethyl;
when X is 3, R6Is selected from 2- (8-R)5-6-R3-4,5-2R2-3-R1-7-R4Phenanthrene) pyridyl or 2- (8-R)5-6-R3-4,5-2R2-3-R1-7-R4-9, 10-dihydrophenanthren-2-yl) pyridyl, wherein R1、R4And R5All selected from any one of hydrogen atom, fluorine atom, methoxyl, cyano, trifluoromethoxy, aliphatic hydrocarbon group of C1-C50, aromatic group of C1-C50 and condensed ring aromatic group of C1-C50; r2Any one selected from hydrogen atom, fluorine atom, trifluoromethyl, methoxy, methyl and C1-C50 aliphatic hydrocarbon group.
2. The compound of claim 1, wherein: the compound shown in the formula I is any one of compounds shown in formula I-1a, formula I-1b, formula I-2a, formula I-2b and formula I-3:
the formula I-1a is specifically a compound shown as PHPT-AC-I:
the formula I-2a is specifically a compound shown as PHIR-AC-I:
the formula I-2b is specifically a compound shown as PHIR-PY-I:
the formula I-3 is specifically a compound represented by PHIR-CJH-I:
in the formula I-1a, the formula I-1b, the formula I-2a, the formula I-2b, the formula I-3, the PHIR-AC-I, PHPT-AC-I, PHIR-PY-I and the PHIR-CJH-I, R1To R5Is defined in relation to R in formula I in claim 11To R5The definitions of (A) are the same;
the R is7Are each a hydrogen atom or an aliphatic hydrocarbon group of C1-C50;
the R is8Are all selected from any one of hydrogen atoms, fluorine atoms, alkyl groups of C1-C10, cyano groups and trifluoromethyl groups;
the PHIR-AC-I compound is more specifically any one of the following compounds:
the PHPT-AC-I compound is more specifically any one of the following compounds:
the compound represented by the PHIR-PY-I is more specifically any one of the following compounds:
the PHIR-CJH-I compound is more specifically any one of the following compounds:
3. a luminescent material comprising a compound of formula I according to any one of claims 1-2; or,
use of a compound of formula I according to any one of claims 1-2 for the preparation of a luminescent material;
the luminescent material is specifically an organic electrophosphorescent luminescent material;
the light-emitting wavelength of the light-emitting material is specifically 460-620 nm.
4. Use of a compound of formula I according to any one of claims 1-2 as a light-emitting layer in the preparation of an organic electroluminescent device;
an organic electroluminescent device comprising a compound of formula I as claimed in any of claims 1 to 2 as a light-emitting layer;
the organic electroluminescent device is specifically an organic electroluminescent phosphorescent device, and more specifically an organic electroluminescent orange phosphorescent material;
the light-emitting wavelength of the light-emitting material is specifically 460-620 nm.
5. The use or device of claim 4, wherein: the organic electroluminescent device consists of a transparent substrate, an anode, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer from bottom to top in sequence;
wherein, the material for forming the transparent substrate is glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material for forming the hole injection layer is TDATA;
the structural formula of the TDATA is as follows:
the material constituting the hole transport layer is NPB;
the structural formula of the NPB is as follows:
the material constituting the organic light-emitting layer is the compound represented by the formula I according to any one of claims 1 to 2 and a host material;
wherein the host material is mCP, CBP, NATZ or
Wherein the structural formulas of mCP, CBP and NATZ are as follows:
the mass of the compound shown in the formula I is 1-10% of that of the main material, specifically 5%;
the material for forming the electron transport layer is Alq3, Gaq3 or BPhen;
wherein the structural formulas of Alq3, Gaq3, BPhen and TPBi are as follows in sequence:
the cathode layer is made of a material selected from any one or two of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
6. The use or device of claim 5, wherein:
the thickness of the hole injection layer is 30-50nm, specifically 40 nm;
the thickness of the hole transport layer is 5-15nm, specifically 10 nm;
the thickness of the organic light-emitting layer is 10-100nm, specifically 50 nm;
the thickness of the electron transmission layer is 10-30nm, specifically 20 nm;
the thickness of the cathode layer is 90-110nm, specifically 100 nm.
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