CN102203109A - 磷光铱络合物 - Google Patents
磷光铱络合物 Download PDFInfo
- Publication number
- CN102203109A CN102203109A CN2009801437747A CN200980143774A CN102203109A CN 102203109 A CN102203109 A CN 102203109A CN 2009801437747 A CN2009801437747 A CN 2009801437747A CN 200980143774 A CN200980143774 A CN 200980143774A CN 102203109 A CN102203109 A CN 102203109A
- Authority
- CN
- China
- Prior art keywords
- substituted
- arylalkyl
- alkyl
- aryl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002503 iridium Chemical class 0.000 title 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 47
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 21
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- -1 vinyloxy group Chemical group 0.000 claims description 12
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 10
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- TUYBTSCLNRYVED-UHFFFAOYSA-N 3,4-difluoro-2-phenylpyridine Chemical compound FC1=CC=NC(C=2C=CC=CC=2)=C1F TUYBTSCLNRYVED-UHFFFAOYSA-N 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 5
- 239000003446 ligand Substances 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 45
- 238000000034 method Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000005215 recombination Methods 0.000 description 8
- 230000027756 respiratory electron transport chain Effects 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000006798 recombination Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 229960000935 dehydrated alcohol Drugs 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 description 1
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical class C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- XEQHAEZWPZICKJ-UHFFFAOYSA-N 2-naphthalen-1-yl-1h-indole Chemical class C1=CC=C2C(C3=CC4=CC=CC=C4N3)=CC=CC2=C1 XEQHAEZWPZICKJ-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910018170 Al—Au Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YTGVNMPXTQBRBK-OVCLIPMQSA-N Cc1cc(O)cc(C)c1/N=C/c1ccc[nH]1 Chemical compound Cc1cc(O)cc(C)c1/N=C/c1ccc[nH]1 YTGVNMPXTQBRBK-OVCLIPMQSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- KLGFDKJPNYXTQP-UHFFFAOYSA-N NCC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 Chemical class NCC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 KLGFDKJPNYXTQP-UHFFFAOYSA-N 0.000 description 1
- QVRQLUCJLGBZAH-GXDHUFHOSA-N Oc1ccc(CC/N=C/c2ccc[nH]2)cc1 Chemical compound Oc1ccc(CC/N=C/c2ccc[nH]2)cc1 QVRQLUCJLGBZAH-GXDHUFHOSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- HRHKULZDDYWVBE-UHFFFAOYSA-N indium;oxozinc;tin Chemical compound [In].[Sn].[Zn]=O HRHKULZDDYWVBE-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WHLAXDUXKMECTM-UHFFFAOYSA-N oxadiazol-4-amine Chemical class NC1=CON=N1 WHLAXDUXKMECTM-UHFFFAOYSA-N 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
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Abstract
式I和IA的金属络合物和衍生自所述络合物的聚合物可用于光电器件(参见I和IA),其中:M为Ir、Co或Rh;XX为环金属化配体(参见XX);R1为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;R2为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;且R1和R2中的至少一者不为氢;R1a为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;R2a为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;且R1a和R2a中的至少一者为被取代的烷基、被取代的芳基、被取代的芳基烷基,且所述被取代的烷基、被取代的芳基或被取代的芳基烷基中的至少一个取代基为可聚合的基团。
Description
发明背景
本发明通常涉及磷光铱络合物、在主链中结合所述络合物或结合所述络合物作为端基的聚合物和含有所述络合物和聚合物的光电器件。
预期利用在经受偏压时发光的薄膜材料的有机发光器件(OLEDs)将成为平板照明和显示技术的日益受欢迎的形式。这是因为OLEDs具有广泛的潜在应用,包括蜂窝电话、个人数字助理(PDAs)、计算机显示器、车载信息显示器、电视监视器以及用于一般照明的光源。由于其颜色明亮、视角宽、与全动视频相容、温度范围广、形状因子薄且适合、动力需求低且具有用于低成本制造工艺的潜能,所以OLEDs被看作是阴极射线管(CRTs)和液晶显示器(LCDs)的未来替代技术。由于其发光效率高,因此对于某些类型的应用来说,OLEDs被看作具有替代白炽灯和或许甚至荧光灯的潜能。
来自OLEDs的光发射通常通过电致发光发生,即从通过对基态电致发光材料两端施加偏压形成的单线激态发射光。认为能够通过其他机制(电致磷光,即从通过对基态电致发光材料两端施加偏压形成的三重激态发射光)产生光的OLEDs将显示出比主要通过电致发光产生光的OLEDs明显更高的量子效率。通过电致磷光从OLEDs发射光受到限制,因为大多数发光有机材料中的三重激态强烈倾向于非辐射驰豫到基态。因此,电致磷光材料有希望作为相对于技术现状显示出更大效率的OLED器件及其它光电器件的关键组分。例如,能够通过电致磷光产生光的OLEDs预期显示出器件内无辐射衰变过程的能量损失量降低(相对于主要通过电致发光产生光的OLEDs来说),由此在OLED的操作期间提供额外的温度控制措施。
改善的发光效率已经通过在诸如OLED的有机电致发光器件中结合含磷光铂的染料来实现(参见Baldo等,“Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices(来自有机电致发光器件的高效磷光发射)”,Nature,395卷,151-154,1998)且也已经使用了磷光含铱的染料(例如参见Lecloux等美国专利申请20030096138,2003年5月22日)。尽管有早先的研发,但当前寻找不仅增加效率而且提供控制OLED产生的光的颜色的更好措施的新型发磷光材料相当重要。例如,将非常希望提供使有机电致发光器件能够具有改善的总效率、而同时允许光输出根据应用的性质而红移或蓝移的新型发磷光材料。
发明简述
简短地讲,一方面,本发明涉及式I金属络合物,衍生自所述络合物的聚合物和含有衍生自所述络合物的聚合物的光电器件,
其中:
M为Ir、Co或Rh;
R1为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;
R2为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;且
R1和R2中的至少一者不为氢。
在特定的实施方案中,M可为Ir。
发明详述
在式I金属络合物中,所述环金属化配体可衍生自苯基吡啶、二氟吡啶、甲苯基吡啶、苯并噻吩基吡啶、芴基吡啶、噻吩基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亚胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基异喹啉、二苯并喹喔啉(dibenzoquinozaline)、8-羟基喹啉、酮基吡咯、吡啶甲酸、乙酰丙酮、六氟乙酰丙酮、亚胺基丙酮、2-(1-萘基)苯并唑)、2-苯基苯并唑、2-苯基苯并噻唑、邻羟基亚苄基、邻羟基苯甲醛、香豆素、苯基吲哚、其衍生物或其组合。具体地说,所述环金属化配体可为苯基吡啶或二氟苯基吡啶。
在特定的实施方案中,R2可为氢。在一些实施方案中,R1可为被取代的烷基、被取代的芳基或被取代的芳基烷基。所述被取代的烷基、被取代的芳基或被取代的芳基烷基的取代基可为可聚合的基团,特别是卤素、羟基、乙烯基、烯丙基、乙烯氧基、烯丙氧基、(甲基)丙烯酸酯、烷基甲硅烷氧基或其组合。特别是,R1可为被取代的芳基。
特别是,R1可选自
本发明的金属络合物的特定实例包括:
根据本发明的光电器件包含具有在主链中或作为端基的衍生自式I金属络合物的结构或末端单元的一种或多种聚合物,也就是说所述聚合物在主链中结合式I金属络合物或结合式I金属络合物作为端基。所述聚合物通常用于发光层中。具体地说,所述光电器件可具有包含具有衍生自至少一种式IA金属络合物的侧基或端基的聚合物的至少一个层,
其中M如上定义;
R1a为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;
R2a为氢、烷基、被取代的烷基、芳基、被取代的芳基、芳基烷基或被取代的芳基烷基;且
R1a和R2a中的至少一者为被取代的烷基、被取代的芳基、被取代的芳基烷基,且所述被取代的烷基、被取代的芳基或被取代的芳基烷基中的至少一个取代基为可聚合的基团。
所述聚合物可包含除了衍生自式I金属络合物的单元以外的单元,诸如另外包含衍生自芴或被取代的芴的结构单元。另外的结构单元可衍生自共轭化合物,例如美国专利第6,900,285号中描述的那些共轭化合物。特别是,可使用衍生自芳族叔胺的结构单元。衍生自不饱和单体的结构单元的量为约0.05%摩尔-约50%摩尔,特别为约1%摩尔-约25%摩尔、更特别为约1%摩尔-约10%摩尔。在一些实施方案中,可将诸如聚(9,9-二辛基芴)的电致发光聚合物及其共聚物(诸如F8-TFB)与所述聚合物共混。
所述聚合物可通过本领域已知用于制备聚芴的方法制备,所述方法包括适当的被二卤素-和二硼酸酯/二硼酸取代的单体的Suzuki偶合、和Yamamoto偶合。美国专利第5,708,130号、第6,169,163号、第6,512,083号和第6,900285号描述了含有芴子单元的聚合物的合成。
光电器件(例如有机发光器件)通常包括多个层,在最简单的情况下,其包括阳极层和相应的阴极层以及布置在所述阳极和所述阴极之间的有机电致发光层。当在电极两端施加偏压时,电子通过阴极注入电致发光层中,同时电子从阳极从电致发光层除去(或“空穴”被“注入”电致发光层中)。随着空穴与电子在电致发光层内结合形成单线态或三线态激子而发生发光,随着单线态激子通过辐射衰减将能量转移到环境而发生发光。根据本发明的光电器件包括由本发明的聚合物组合物构成的有机电致发光层。
除了阳极、阴极和发光材料以外可以存在于有机发光器件中的其它部件包括空穴注入层、电子注入层和电子传输层。电子传输层不必与阴极接触,且电子传输层常常不是有效的空穴运输者且因此用于阻挡空穴向阴极迁移。在包括电子传输层的有机发光器件的操作期间,存在于电子传输层中的大部分载流子(即空穴和电子)为电子且发光可通过存在于电子传输层中的空穴和电子的复合而发生。可存在于有机发光器件的另外部件包括空穴传输层、空穴传输发射(emission(emitting))层和电子传输发射层。
所述有机电致发光层为在有机发光器件内的层,当处于操作中时,其含有显著浓度的电子和空穴二者且提供激子形成和发光的部位。空穴注入层为与阳极接触的层,其促进空穴从阳极注入OLED的内部层中;电子注入层为与阴极接触的层,其促进电子从阴极注入OLED中;电子传输层为便于电子从阴极传导到电荷复合部位的层。空穴传输层为当OLED处于操作中时便于空穴从阳极传导到电荷复合部位且不必与阳极接触的层。空穴传输发射层为当OLED处于操作中时便于空穴传导到电荷复合部位且大部分载流子为空穴且发射不仅通过与残留电子复合发生、而且通过从器件中其它地方的电荷复合区转移能量发生的层。电子传输发射层为当OLED处于操作中时便于电子传导到电荷复合部位且大部分载流子为电子且发射不仅通过与残留空穴复合发生、而且通过从器件中其它地方的电荷复合区转移能量发生的层。
适合用作阳极的材料包含具有通过四点探针技术测量的至少约100欧姆/□的体积电导率的材料。常将氧化铟锡(ITO)用作阳极,因为其对光透射基本透明且因此便于从电活性有机层发射的光逸出。可用作阳极层的其它材料包含氧化锡、氧化铟、氧化锌、氧化铟锌、氧化锌铟锡、氧化锑及其混合物。
适合用作阴极的材料包括可将负载流子(电子)注入OLED的(一个或多个)内层中的零价金属。适合用作阴极20的各种零价金属包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、镧系元素、其合金及其混合物。用作阴极层的合适合金材料包括Ag-Mg、Al-Li、In-Mg、Al-Ca和Al-Au合金。多层非合金结构也可用于阴极中,诸如,由诸如铝或银的零价金属的较厚层覆盖的诸如钙的金属或诸如LiF的金属氟化物的薄层。特别是,阴极可由单一零价金属构成,特别是由铝金属构成。
适用于空穴注入层的材料包括3,4-亚乙二氧基噻吩(PEDOT)和PEDOT与聚苯乙烯磺酸酯(PSS)的共混物,从H.C.Stark,Inc.以商品名BAYTRON购得;和基于噻吩并[3,4b]噻吩(TT)单体的聚合物,从Air Products Corporation购得。
适用于空穴传输层的材料包括如美国专利第6,023,371号中所公开的1,1-双((二-4-甲苯基氨基)苯基)环己烷、N,N′-双(4-甲基苯基)-N,N′-双(4-乙基苯基)-(1,1′-(3,3′-二甲基)联苯)-4,4′-二胺、四(3-甲基苯基)-N,N,N′,N′-2,5-苯二胺、苯基-4-N,N-二苯基氨基苯乙烯、对-(二乙氨基)苯甲醛二苯基腙、三苯胺、1-苯基-3-(对-(二乙氨基)苯乙烯基)-5-(对-(二乙氨基)苯基)吡唑啉、1,2-反-双(9H-咔唑-9-基)环丁烷、N,N,N′,N′-四(4-甲基苯基)-(1,1′-联苯)-4,4′-二胺、铜酞菁、聚乙烯基咔唑、(苯基甲基)聚硅烷、聚(3,4-亚乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族叔胺、腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、具有氨基的二唑衍生物和聚噻吩。
实施例
配体合成
在22℃下制备并混合吡咯-2-甲醛(Aldrich,1.0g,10.51毫摩尔)和4-溴苯胺(Aldrich,1.81g,10.52毫摩尔)的无水乙醇(5mL)溶液14小时。所形成的灰白色固体沉淀物通过真空过滤收集(1.47g,6毫摩尔,产率56%)。产物通过1H-NMR和13C-NMR的分析与所要产物N-((1H-吡咯-2-基)亚甲基)-4-溴苯胺的形成一致。
在22℃下制备并混合吡咯-2-甲醛(Aldrich,1.0g,10.51毫摩尔)和酪胺(Aldrich,1.44g,10.51毫摩尔)的无水乙醇(5mL)溶液14小时。所形成的灰白色固体沉淀物通过真空过滤收集(1.22g,5.7毫摩尔,产率54%)。产物通过1H-NMR和13C-NMR的分析与所要产物4-(2-((1H-吡咯-2-基)亚甲基氨基)乙基)苯酚的形成一致。
实施例3
在22℃下制备并混合吡咯-2-甲醛(Aldrich,1.0g,10.51毫摩尔)和丝氨醇(Aldrich,0.96g,10.51毫摩尔)的无水乙醇(5mL)溶液14小时。通过旋转蒸发除去乙醇,留下淡黄色油状产物(1.2g,5.7毫摩尔,产率54%)。产物通过1H-NMR和13C-NMR的分析与所要亚胺的形成一致。
在22℃下制备并混合吡咯-2-甲醛(Aldrich,1.0g,10.51毫摩尔)和环己胺(Aldrich,1.04g,10.51毫摩尔)的无水乙醇(5mL)溶液14小时。通过旋转蒸发除去乙醇,留下淡黄色油状产物(1.1g,5.7毫摩尔,产率54%)。产物通过1H-NMR和13C-NMR的分析与所要亚胺的形成一致。
实施例5
在22℃下制备并混合吡咯-2-甲醛(Aldrich,1.0g,10.51毫摩尔)和乙醇胺盐酸盐(Aldrich,1.03g,10.51毫摩尔)的无水乙醇(5mL)溶液14小时。通过旋转蒸发除去乙醇,留下暗黑色油状产物。产物通过1H-NMR和13C-NMR的分析与所要亚胺的形成不一致。
配体的组合合成
通用方法A
在乙醇中合成亚胺配体的通用方法:向在Chemspeed自动工作站上的不同孔中加入1.3毫摩尔的如下所列的6种胺。随后在N2下加入5mL干燥乙醇。随后将反应器在25℃下以300rpm涡旋10分钟。将1H-吡咯-2-甲醛(1134mg,在29.9mL无水EtOH中)的储备溶液放置在Chemspeed自动工作站上。Chemspeed自动工作站的液体输送机向各个含有胺的孔传送1.3毫摩尔1H-吡咯-2-甲醛(约3.3mL)。涡旋增加到850rpm且使温度升高到75℃历时10小时。随后将涡旋降低到300rpm且使温度降到25℃。
通用方法B
使用类似于上述程序的程序,将约100mg活化4A分子筛、1.3毫摩尔如下所列的4种胺和5mL干燥甲苯装入Chemspeed反应器的不同孔中。将1H-吡咯-2-甲醛(799mg,在19.77mL干燥甲苯中)的储备溶液放置在Chemspeed自动工作站上。Chemspeed自动工作站的液体输送机向各个含有胺的孔传送1.3毫摩尔1H-吡咯-2-甲醛(约2.9mL)。涡旋增加到850rpm且使温度升高到75℃历时10小时。随后将涡旋降低到300rpm且使温度降到25℃。
纯化
处理:对于亚胺配体4-((1H-吡咯-2-基)亚甲基氨基)-3,5-二甲基苯酚和N-((1H-吡咯-2-基)亚甲基)-2,6-二甲基苯胺来说,经确定在下一步骤中使用不纯的反应混合物是最方便的,因此不必进行进一步纯化(对于甲苯路径,通过过滤除去4A分子筛)。对于其它配体(与路径无关),溶液经45微米过滤器过滤且在氮气流下除去溶剂。使用乙醇的小等分试样再溶解残余物并将1.5g硅胶加到各反应中。在真空下除去乙醇且使用硅胶来装载纯化配体(乙酸乙酯/己烷梯度)的Combi-快速层析体系。合并含有产物的流分并除去溶剂。所得固体通过NMR(d6-DMSO)鉴定。
使用上述通用方法B,将4-乙烯基苯胺转化为N-((1H-吡咯-2-基)亚甲基)-4-乙烯基苯胺。
使用上述通用方法B,将烯丙胺转化为N-((1H-吡咯-2-基)亚甲基)丙-2-烯-1-胺。
使用上述通用方法B,将2,6-二甲基苯胺转化为N-((1H-吡咯-2-基)亚甲基)-2,6-二甲基苯胺。
实施例9
使用上述通用方法B,将4-氨基-3,5-二甲基苯酚转化为4-((1H-吡咯-2-基)亚甲基氨基)-3,5-二甲基苯酚。
磷光络合物的合成
实施例10
将[(4,6-二氟苯基)-吡啶根合(pyridinato)-N,C2]2IrCl二聚体(American Dye Source,0.25g,0.20毫摩尔)溶解于含有4-(2-((1H-吡咯-2-基)亚甲基氨基)乙基)苯酚(实施例2,0.102g,0.48毫摩尔)和碳酸钠(Aldrich,0.25g,过量)的6mL二甲基甲酰胺中。将溶液加热到85℃历时14小时。将溶液冷却到22℃并过滤以从碳酸钠中分离。逐滴加到己烷中,产生黄色微晶固体(170mg,产率53%)。结构通过1H-NMR和13C-NMR证实。
实施例11
将[(4,6-二氟苯基)-吡啶根合-N,C2]2IrCl二聚体(American Dye Source,0.25g,0.20毫摩尔)溶解于含有N-((1H-吡咯-2-基)亚甲基)-4-溴苯胺(实施例1,0.130g,0.48毫摩尔)和碳酸钠(Aldrich,0.25g,过量)的6mL二甲基甲酰胺中。将溶液加热到85℃历时14小时。将溶液冷却到22℃并过滤以从碳酸钠中分离。逐滴加到己烷中,产生黄色微晶固体(194mg,产率58%)。结构通过1H-NMR和13C-NMR证实。
磷光络合物的组合合成
通用方法C:使用以下程序在THF/甲苯中使上述实施例6-9的配体独立地与两种Ir络合物[(4,6-F2ppy)2IrCl]2和[(ppy)2IrCl]2反应:将作为固体或在甲苯溶液中的各配体(300毫摩尔)装入具有220mgNa2CO3的Chemspeed反应器中。加入甲苯使总体积达到5mL。加入作为来自THF的浆液的Ir二聚体(100毫摩尔二聚体)。加入THF以使总体积达到10mL。使Chemspeed反应器在85℃下以850rpm涡旋14小时。随后将溶液经45微米过滤器过滤并用THF洗涤。除去THF并将残余物再溶解于少量THF中。随后加入硅胶(1.5g)并在真空下除去THF。使用硅胶来装载Combi快速层析体系,在其中纯化络合物(参见下文)(乙酸乙酯/己烷梯度洗脱)。合并含有产物的流分并除去溶剂。将残余物从氯仿/己烷中重结晶且产物通过NMR光谱鉴定。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)丙-2-烯-1-胺(实施例7)与[(4,6-二氟苯基)-吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物(83mg,产率59%)。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)-4-乙烯基苯胺(实施例6)与[(4,6-二氟苯基)-吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物(89mg,产率58%)。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)-2,6-二甲基苯胺(实施例8)与[(4,6-二氟苯基)-吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,4-((1H-吡咯-2-基)亚甲基氨基)-3,5-二甲基苯酚(实施例9)与[(4,6-二氟苯基)-吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)-4-溴苯胺(实施例1)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,4-(2-((1H-吡咯-2-基)亚甲基氨基)乙基)苯酚(实施例2)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
实施例18
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)丙-2-烯-1-胺(实施例7)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)-4-乙烯基苯胺(实施例6)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,N-((1H-吡咯-2-基)亚甲基)-2,6-二甲基苯胺(实施例8)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
根据上述通用方法C,4-((1H-吡咯-2-基)亚甲基氨基)-3,5-二甲基苯酚(实施例9)与[(苯基吡啶根合-N,C2]2IrCl二聚体的反应得到所要产物。
虽然在本文中仅说明并描述了本发明的某些特征,但本领域技术人员将想到许多修改和变化。因此,所附权利要求书将涵盖所有这类属于本发明的真实精神内的修改和变化。
Claims (23)
2.权利要求1的光电器件,其中所述环金属化配体为苯基吡啶或二氟苯基吡啶。
3.权利要求1的光电器件,其中M为Ir。
4.权利要求1的光电器件,其中R2为氢。
5.权利要求1的光电器件,其中R1为被取代的烷基、被取代的芳基或被取代的芳基烷基。
6.权利要求5的光电器件,其中所述被取代的烷基、被取代的芳基或被取代的芳基烷基的至少一个取代基为可聚合的基团。
7.权利要求6的光电器件,其中所述可聚合的基团为卤素、羟基、乙烯基、烯丙基、乙烯氧基、烯丙氧基、(甲基)丙烯酸酯、烷基甲硅烷氧基或其组合。
10.权利要求6的光电器件,其中所述至少一个层包含具有衍生自式I金属络合物的结构或末端单元的聚合物。
11.权利要求10的光电器件,其中所述聚合物另外包含衍生自芴或被取代的芴的结构单元。
13.权利要求12的光电器件,其中所述被取代的烷基、被取代的芳基或被取代的芳基烷基的至少一个取代基为卤素、羟基、烷氧基甲硅烷基、乙烯基或(甲基)丙烯酸酯。
15.权利要求14的金属络合物,其中M为Ir。
16.权利要求14的金属络合物,其中所述被取代的烷基、被取代的芳基或被取代的芳基烷基的至少一个取代基为可聚合的基团。
17.权利要求15的金属络合物,其中所述可聚合的基团为卤素、羟基、乙烯基、烯丙基、乙烯氧基、烯丙氧基、(甲基)丙烯酸酯、烷基甲硅烷氧基或其组合。
19.权利要求14的金属络合物,其中所述环金属化配体为苯基吡啶或二氟苯基吡啶。
22.权利要求21的聚合物,其另外包含衍生自芴或被取代的芴的结构单元。
23.权利要求21的聚合物,其中所述被取代的烷基、被取代的芳基或被取代的芳基烷基的至少一个取代基为卤素、羟基、烷氧基甲硅烷基、乙烯基或(甲基)丙烯酸酯。
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