CN104804045A - 近红外发光材料及有机电致发光器件 - Google Patents
近红外发光材料及有机电致发光器件 Download PDFInfo
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- CN104804045A CN104804045A CN201510173262.2A CN201510173262A CN104804045A CN 104804045 A CN104804045 A CN 104804045A CN 201510173262 A CN201510173262 A CN 201510173262A CN 104804045 A CN104804045 A CN 104804045A
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- iridium
- complex
- electroluminescence device
- layer
- organic electroluminescence
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- 239000000463 material Substances 0.000 title claims abstract description 36
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 132
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 129
- 238000005401 electroluminescence Methods 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 230000005540 biological transmission Effects 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 11
- -1 carbazyl Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 claims description 2
- HCIMXTXCDVBLOA-UHFFFAOYSA-N [4-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=C(C(F)(F)F)C=C1 HCIMXTXCDVBLOA-UHFFFAOYSA-N 0.000 claims description 2
- 230000021615 conjugation Effects 0.000 claims description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003384 small molecules Chemical class 0.000 claims description 2
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- 238000000034 method Methods 0.000 description 8
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 239000012298 atmosphere Substances 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 3
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- FZICDBOJOMQACG-UHFFFAOYSA-N benzo[h]isoquinoline Chemical compound C1=NC=C2C3=CC=CC=C3C=CC2=C1 FZICDBOJOMQACG-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 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
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GGHQCCFDFXDENC-UHFFFAOYSA-N N1=CC=CC=C1.C1(=CC=CC=C1)C=1N=NNC1 Chemical compound N1=CC=CC=C1.C1(=CC=CC=C1)C=1N=NNC1 GGHQCCFDFXDENC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
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- 230000006399 behavior Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 150000001716 carbazoles Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000004297 night vision Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000012780 transparent material Substances 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
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Abstract
本发明提供一种用作近红外发光材料的铱配合物以及含有该铱配合物的有机电致发光器件,该铱配合物的结构通式为LnIrX3-n或[LnIrX3-n]+Z-,其中,Ir是所述铱配合物的中心原子,L与X均为所述铱配合物的配体,Z-为阴离子,n=1,2或3,L选自:。
Description
技术领域
本发明涉及一种近红外发光材料,尤其涉及一种金属铱配合物以及应用该金属铱配合物的有机电致发光器件,属于有机发光显示技术领域。
背景技术
近红外区是指波长从700纳米到1500纳米的一段波谱区间。最近几年,近红外材料和技术引起了科学界越来越多的关注和投入。在军需方面,近红外技术被用于热源目标锁定、区域防务、夜视设备、导弹定位和目标追踪等;在民用方面,近红外技术可用于热效率分析、温度遥感传输、短程无限通讯及天气预报等;在生物体组织和细胞中,近红外光可以穿透表层进入生物体组织,且能避免生物体自荧光的信号干涉,因此近红外光谱是最佳的生物分析窗口;近红外光谱也是光纤通信的窗口,波长为1.31和1.55微米的近红外光源能使光纤的损耗降到最低;此外,将近50%的太阳能落于近红外区,为了充分利用这部分能量,也需要开发新型的近红外光伏材料。
环金属铱配合物由于具备丰富的光物理特性而成为一类优秀的磷光染料,广泛用于有机发光器件、传感器和激光器等。目前,环金属铱配合物在红光、绿光及蓝光等可见光区已取得了成功的应用。然而,环金属铱配合物在近红外区的研究尚未突破,目前研究的两个难点在于:发光波长的进一步红移和提高近红外发光效率,为了使近红外发光材料发射波长红移,需要通过调整分子结构来降低HOMO-LUMO间的能隙,然而由能隙规则可知,随着能隙变窄,激发态非辐射弛豫的速率就会变大,导致发光效率下降。如何解决波长红移和发光效率下降之间的矛盾,找到近红外区发光纯正且具有相当发光效率的金属铱配合物是目前近红外发光材料研究的难点。
发明内容
有鉴于此,确有必要提供一种光色纯正且具有较高发光效率的近红外发光材料铱配合物,以及含有该铱配合物的有机电致发光器件。
一种用作近红外发光材料的铱配合物,该铱配合物的结构通式为LnIrX3-n或[LnIrX3-n]+Z-,其中,Ir是所述铱配合物的中心原子,L与X均为所述铱配合物的配体,Z-为阴离子,n=1,2或3,L选自具有以下通式的L1配体、L2配体或L3配体:
其中,R1~R8分别独立地选自氢原子、碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、碳原子数为1~10的烷基氨基、咔唑基、氟原子、三氟甲基和碳原子数为5~18的芳香基团,Ar选自碳原子数为5~18的芳基和碳原子数为5~18的杂环芳基。
一种有机电致发光器件,包括一阳极、一空穴传输层、一有机发光层、一电子传输层以及一阴极,所述有机发光层包括上述铱配合物。
在所述L1配体、L2配体和L3配体中,三个芳环并联形成一个大的共轭体系,同时引入吸电子性的氮杂原子,有效地降低了分子HOMO轨道和LUMO轨道的裂分,使得所述铱配合物发光红移;如此刚性结构的配体,可有效控制所述铱配合物的几何异构化以及限制所述铱配合物分子内的转动,提高了所述铱配合物的发光效率,并且还可以减少所述铱配合物三线态激子间的淬灭,克服含有该铱配合物的有机电致发光器件在大电流密度下效率滚降的问题;同时,更重要的是,由于进行配位的N原子所在的位阻基团与进行配位的C原子所在的位阻基团同时位于该两个配位原子的同一侧,因此金属铱元素可与该两个配位原子从另一侧进行螯合而不会受到任何位阻基团的阻碍,使空间位阻效应的影响大大降低,从而使所述铱配合物具有很高的稳定性,不仅进一步提高了所述铱配合物的发光效率,而且有利于改善含有该铱配合物的有机电致发光器件的使用寿命。
附图说明
图1为本发明提供的有机电致发光器件的结构示意图。
图2为本发明实施例16、实施例18、实施例27以及实施例31与对比例1提供的铱配合物的理论计算对比图。
图3为本发明实施例29提供的铱配合物C2-13和对比例1提供的对比配合物2的热重分析(TGA)图。
图4为本发明实施例36提供的有机电致发光器件的电致发光谱图。
图5为本发明实施例36提供的有机电致发光器件的辐射出射度-电压曲线以及电流密度-电压曲线。
图6为本发明实施例36提供的有机电致发光器件的外量子效率-电流密度曲线。
图7为本发明实施例37提供的有机电致发光器件的外量子效率-电流密度曲线。
如下具体实施方式将结合上述附图进一步说明本发明。
具体实施方式
下面将结合附图及具体实施例对本发明提供的铱配合物以及含有该铱配合物的有机电致发光器件作进一步的详细说明。
本发明提供一种用作近红外发光材料的铱配合物,该铱配合物的结构通式为LnIrX3-n或[LnIrX3-n]+Z-,其中,Ir为金属铱元素,Ir是所述铱配合物的中心原子,L与X均为所述铱配合物的配体,Z-为阴离子,n=1,2或3。
结构通式为LnIrX3-n的铱配合物为中性配合物,结构通式为[LnIrX3-n]+Z-的铱配合物为离子型配合物。
L选自具有以下通式的L1配体、L2配体或L3配体:
R1~R8可分别独立地选自氢原子、碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、碳原子数为1~10的烷基氨基、咔唑基、氟原子、三氟甲基和碳原子数为5~18的芳香基团中的一种。Ar可选自碳原子数为5~18的芳基和碳原子数为5~18的杂环芳基中的一种。
X为双齿配位体。在本发明实施例中,X可选自联吡啶、1,10-菲啰啉、4,7-二苯基-1,10-菲啰啉、乙酰丙酮、二苯甲酰基甲烷、二叔戊酰甲烷以及吡啶甲酸。
Z-为一价阴离子。在本发明实施例中,Z-可选自氯离子,六氟磷酸根、高氯酸根、四苯基硼酸根以及四(对三氟甲基苯基)硼酸根。
优选地,所述铱配合物可选自:
其中,所述铱配合物C1-1至C1-16以所述L1配体为主配体,所述铱配合物C2-1至C2-14以所述L2配体为主配体,所述铱配合物C3-1至C3-7以所述L3配体为主配体。可以理解,所述铱配合物C1-1至C1-16的L1配体、所述铱配合物C2-1至C2-14的L2配体以及所述铱配合物C3-1至C3-7的L3配体的芳香环上还可以具有R1~R8取代基中的一种或多种。
对于所述L1配体,所述金属铱元素同时与N原子以及Ar基团上的C原子进行配位。对于所述L2配体和L3配体,所述金属铱元素同时与离Ar基团最近的N原子以及Ar基团上的C原子进行配位。
在所述L1配体、L2配体和L3配体中,三个芳环并联形成一个大的共轭体系,同时引入吸电子性的氮杂原子,有效地降低了分子HOMO轨道和LUMO轨道的裂分,使得所述铱配合物发红红移;如此刚性结构的配体,可有效控制所述铱配合物的几何异构化以及限制所述铱配合物分子内的转动,提高了所述铱配合物的发光效率,并且还可以减少所述铱配合物三线态激子间的淬灭,克服含有该铱配合物的有机电致发光器件在大电流密度下效率滚降的问题;同时,更重要的是,由于进行配位的N原子所在的位阻基团与进行配位的C原子所在的位阻基团同时位于该两个配位原子的同一侧(结构式左侧),因此所述金属铱元素可与该两个配位原子从另一侧(结构式右侧)进行螯合而不会受到任何位阻基团的阻碍,使空间位阻效应的影响大大降低,从而使所述铱配合物具有很高的稳定性,不仅进一步提高了所述铱配合物的发光效率,而且有利于改善含有该铱配合物的有机电致发光器件的使用寿命。
其中,所述L1配体的制备可参照以下路线及方法:
向苯并异喹啉的乙醚溶液(12mL)中加入溴化苯基镁(2.5M,在2.55mL的四氢呋喃中),23℃搅拌36小时。之后用10mL的NH4Cl溶液淬灭反应,分液,浓缩有机相,柱层析分离,得黄色固体粉末,产率为38%。
用带有取代基的苯并异喹啉和带有取代基的溴化苯基镁可以得到不同的所述L1配体。
所述L2配体的制备可参照以下路线及方法:
将2.1g(6.35mmol)配体原料溶于40mL甲醇中,再加入过量水合肼,于室温搅拌1小时等到黄色沉淀,再用甲醇重结晶,产率90%。
用带有取代基的甲酰乙烷和水合肼可以得到不同的所述L2配体。
所述L3配体的制备可参照以下路线及方法:
将2mmol的3-氨基萘-2-苯甲酮,3mmol氨基乙酸,1mmol碘和0.55mL叔丁基过氧化氢(70%水溶液)溶于5mL二甲基甲酰胺中,于密封管中80℃反应18小时。柱层析分离,得黄色固体,产率70%。
用带有取代基的3-氨基萘-2-苯甲酮和带有取代基的氨基乙酸可以得到不同的L3配体。
请参阅图1,本发明进一步提供一种有机电致发光器件10,包括一阳极120、一空穴传输层130、一有机发光层140、一电子传输层160以及一阴极170。所述有机发光层140包括所述铱配合物。
所述阳极120、空穴传输层130、有机发光层140、电子传输层160以及阴极170依次层叠设置。所述阳极120用于向所述空穴传输层130注入空穴。所述阳极120由导电材料组成。所述阳极120的导电材料可为选自铟锡氧(ITO),铟锌氧(IZO),二氧化锡(SnO2),氧化锌(ZnO)、银、铝、金、铂以及钯的一种或几种。
所述有机电致发光器件10可以进一步包括一基板110,用于承载所述阳极120、空穴传输层130、有机发光层140、电子传输层160以及阴极170。所述基板110为透明材料,例如玻璃或塑料。所述基板110可具有光滑的表面,以便容易进行处理。
所述空穴传输层130用于将空穴从所述阳极传输到所述有机发光层140。所述空穴传输层130的材料为具有较高空穴迁移率的材料。所述空穴传输层130的材料可为选自酞菁化合物以及芳香胺类化合物中的一种或几种,例如4,4’-二[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N'-二(3-甲基苯基)-N,N'-二苯基联苯(TPD)、1,3,5-三(3-甲基二苯氨基)苯(m-MTDATA)、聚乙烯基咔唑(PVK)等。
所述有机发光层140可发射近红外光。所述有机发光层140包括一主体材料以及所述铱配合物,所述主体材料通过接收空穴和电子产生激子,然后向所述铱配合物转移激子的能量,所述铱配合物利用转移的能量通过形成激子的方式而发光。所述主体材料可选自含咔唑类共轭小分子、芳基硅类小分子以及金属配合物中的一种或几种,例如聚乙烯基咔唑/2-(4-联苯基)-5-苯基恶二唑(PVK/PBD)、4,4’-(N,N’-二咔唑基)-联苯(CBP)、8-羟基喹啉铝(Alq3)、镓双核配合物Ga2(saph)2q2、双(10-羟基苯并[h]喹啉)铍(Bebq2)等。
所述铱配合物在所述有机发光层中的用量可以根据实际需要进行调控。当所述铱配合物的掺杂浓度很低时,主体材料到所述铱配合物能量传输不完全,但当浓度掺杂过高时,所述铱配合物的浓度淬灭现象又会很严重。优选地,所述铱配合物占所述有机发光层140总质量的1%至30%,这一用量范围的所述铱配合物既可以大大减轻三重态激子的自淬灭程度,又可以实现主体材料到铱配合物的有效能量传输,提高所述有机电致发光器件的发光效率,并使所述有机电致发光器件具有较长的使用寿命。
所述电子传输层160用于将电子从所述阴极传输到所述有机发光层140。所述电子传输层160的材料为具有较高电子迁移率的材料。所述电子传输层160的材料可为为噁唑类化合物、金属络合物、喹啉类化合物、喔啉类化合物、二氮蒽衍生物及二氮菲衍生物的一种或几种,例如8-羟基喹啉铝(Alq3)及其衍生物。
所述有机电致发光器件10可进一步包括一空穴阻挡层150,用于阻挡空穴向电子传输层160的传输,从而提高载流子传输效率,有利于获得高效的发光效率。所述空穴阻挡层150可设置在所述有机发光层140与所述电子传输层160之间。所述空穴阻挡层150的材料可选自2,9-二甲基-4,7-二苯基-1,10-菲啰啉(BCP)、4,7-二苯基-1,10-菲啰啉(BPhen)、1,3,5-三(2-N-苯基苯并咪唑基)苯(TPBI)以及3-(4-二苯基)-5-(4-叔丁基苯基)-4-(4-乙基苯基)-1,2,4-三唑(TAZ)中的一种或几种。所述空穴阻挡层150的材料也可与所述电子传输层160的材料相同。
所述阴极170用于向所述电子传输层160注入电子。所述阴极170的材料可以采用锂、镁、铝、钙、铝锂合金、镁银合金、镁铟合金等低功函数的金属或合金,或金属与金属氟化物交替形成的电极层。
可以理解,所述有机电致发光器件10还可进一步包括一个或两个中间层、空穴注入层、电子注入层以及电子阻挡层等。
本发明提供的有机电致发光器件可以发出纯正的近红外光,该有机电致发光器件具有较高的发光效率及较长的使用寿命,且效率滚降现象受到了明显抑制,可在大电流密度条件下进行使用。
实施例1:铱配合物C1-1的制备
将IrCl3·xH2O(58%Ir)和2.2倍化学当量的L1配体溶于乙二醇甲醚和去离子水(v/v=3/1)的混合溶剂中。在Ar气氛下110℃回流搅拌24小时。冷至室温后过滤,滤饼用去离子水洗至中性,再依次用10mL乙醇、200mL乙醚淋洗滤饼。最后用二氯甲烷溶解滤饼,收集滤液,蒸除溶剂,70℃真空干燥5小时,得到深褐色固体的二氯桥连中间体,产率85%,无需进一步提纯直接投入下步反应。
将0.34mmol二氯桥连中间体和1.0g 4,7-二苯基-1,10-菲啰啉溶于40mL乙二醇中,反应体系用氮气保护,130℃回流搅拌15小时。冷至室温后将反应液倒入100mL的烧瓶中,在搅拌下向其加入饱和的NH4PF6水溶液,析出大量固体,过滤,用少量去离子水洗涤,70℃真空干燥5小时,粗产品用色谱柱进行层析分离,得到深褐色固体,产率50%。
ESI-MS(电喷雾离子化质谱)[m/z]:801[M+H]+。
元素分析(C63H42N4IrPF6):Anal.Calcd.(理论值):C,63.47;H,3.55;N,4.70;Found(测量值):C,63.55;H,3.88;N,4.53。
实施例2:铱配合物C1-2的制备
二氯桥连中间体的制备方法请参见实施例1。
将0.17mmol二氯桥连中间体、0.05g(0.5mmol)乙酰丙酮及0.056g(0.5mmol)叔丁醇钾溶于12mL二氯甲烷/乙醇(体积比=3/1)的混合溶剂中。反应体系用氩气保护,30℃回流搅拌24小时。冷至室温后,蒸干溶剂,再用二氯甲烷溶解,去离子水萃取3次,用无水MgSO4干燥有机相。过滤,蒸除溶剂,柱层析分离,收集黑色的产物带。浓缩后再用二氯甲烷/乙醚重结晶,得黑色固体,产率45%。
1H-NMR(核磁共振,CDCl3,300MHz,δ[ppm]):1.62(s,6H),4.54(s,H),7.02(d,2H),7.47~7.54(m,6H),7.63~7.67(m,6H),7.79(s,2H),8.16~8.18(m,6H),8.30(d,2H)。
ESI-MS[m/z]:801[M+H]+。
元素分析(C43H31N2IrO2):Anal.Calcd.:C,64.56;H,3.91;N,3.50;Found:C,64.55;H,3.88;N,3.53。
实施例3:铱配合物C1-3的制备
将IrCl3·xH2O(58%Ir)和过量L1配体及三氟甲磺酸银溶于乙二醇甲醚和去离子水(体积比=3/1)的混合溶剂中。在N2气氛下110℃回流搅拌18小时。冷至室温后过滤,滤饼用去离子水洗至中性,再依次用10mL乙醇、200mL乙醚淋洗滤饼。最后用二氯甲烷溶解滤饼,收集滤液,旋蒸除去溶剂,70℃真空干燥5小时,得到深褐色固体,柱层析分离,产率65%。
ESI-MS[m/z]:955[M+H]+。
元素分析(C57H35IrN3):Anal.Calcd.:C,71.75;H,3.70;N,4.40;Found:C,71.55;H,3.88;N,4.53。
实施例4:铱配合物C1-4的制备
本实施例与实施例2基本相同,其不同之处主要在于,L1配体中的Ar基团不同,产物产率为47%。
ESI-MS[m/z]:901[M+H]+。
元素分析(C51H35IrN2O2):Anal.Calcd.:C,68.06;H,3.92;N,3.11;Found:C,68.35;H,3.78;N,3.43。
实施例5:铱配合物C1-5的制备
本实施例与实施例3基本相同,其不同之处主要在于,L1配体中的Ar基团不同,产物产率为35%。
ESI-MS[m/z]:1105[M+H]+。
元素分析(C69H41IrN3):Anal.Calcd.:C,75.05;H,3.74;N,3.81;Found:C,74.95;H,3.68;N,3.53。
实施例6:铱配合物C1-6的制备
本实施例与实施例2基本相同,其不同之处主要在于,L1配体中的Ar基团不同,产物产率为45%。
ESI-MS[m/z]:901[M+H]+。
元素分析(C51H35IrN2O2):Anal.Calcd.:C,68.06;H,3.92;N,3.11;Found:C,68.35;H,3.88;N,3.36。
实施例7:铱配合物C1-7的制备
本实施例与实施例1基本相同,其不同之处在于,L1配体中的Ar基团不同,且用联吡啶代替4,7-二苯基-1,10-菲啰啉,产物产率为40%。
ESI-MS[m/z]:869[M-PF6]+。
元素分析(C44H28F6IrN4PS2):Anal.Calcd.:C,52.12;H,2.78;N,5.53;Found:C,52.45;H,2.88;N,5.35。
实施例8:铱配合物C1-8的制备
本实施例与实施例2基本相同,其不同之处在于,L1配体中的Ar基团不同,产物产率为40%。
ESI-MS[m/z]:813[M+H]+。
元素分析(C39H27IrN2O2S2):Anal.Calcd.:C,57.69;H,3.35;N,3.45;Found:C,57.55;H,3.68;N,3.53。
实施例9:铱配合物C1-9的制备
本实施例与实施例3基本相同,其不同之处在于,L1配体中的Ar基团不同,产物产率为40%。
ESI-MS[m/z]:974[M+H]+。
元素分析(C51H30IrN3S3):Anal.Calcd.:C,62.94;H,3.11;Ir,19.75;N,4.32;S,9.88;Found:C,62.65;H,3.28;N,4.53。
实施例例10:铱配合物C1-10的制备
本实施例与实施例1基本相同,其不同之处在于,L1配体中的Ar基团不同,且用1,10-菲啰啉代替4,7-二苯基-1,10-菲啰啉,产物产率为37%。
ESI-MS[m/z]:993[M-PF6]+。
元素分析(C54H32F6IrN4PS2):Anal.Calcd.:C,56.98;H,2.83;N,4.92;Found:C,56.65;H,3.58;N,4.68。
实施例11:铱配合物C1-11的制备
本实施例与实施例2基本相同,其不同之处在于,L1配体中的Ar基团不同,产物产率为40%。
ESI-MS[m/z]:913[M+H]+。
元素分析(C47H31IrN2O2S2):Anal.Calcd.:C,61.89;H,3.43;N,3.07;Found:C,61.65;H,3.28;N,3.43。
实施例12:铱配合物C1-12的制备
本实施例与实施例3基本相同,其不同之处在于,L1配体中的Ar基团不同,产物产率为40%。
ESI-MS[m/z]:1124[M+H]+。
元素分析(C63H36IrN3S3):Anal.Calcd.:C,67.36;H,3.23;N,3.74;Found:C,67.65;H,3.28;N,3.43。
实施例13:铱配合物C1-13的制备
本实施例与实施例3基本相同,其不同之处在于,L1配体中的Ar基团不同,产物产率35%。
ESI-MS[m/z]:1106[M+H]+。
元素分析(C69H42IrN3):Anal.Calcd.:C,74.98;H,3.83;N,3.80;Found:C,66.78;H,3.88;N,5.84。
实施例14:铱配合物C1-14的制备
本实施例与实施例2基本相同,其不同之处在于,L1配体中的取代基R7及R8不同,产物产率为35%。
ESI-MS[m/z]:901[M+H]+。
元素分析(C51H35IrN2O2):Anal.Calcd.:C,68.06;H,3.92;N,3.11;Found:C,66.78;H,3.88;N,5.84。
实施例15:化合物C1-15
本实施例与实施例1基本相同,其不同之处在于,L1配体中的取代基R7及R8不同,且用苯基三唑吡啶代替4,7-二苯基-1,10-菲啰啉,产物产率为37%。
ESI-MS[m/z]:1022[M-PF6]+。
元素分析(C59H37F6IrN6P):Anal.Calcd.:C,60.71;H,3.20;N,7.20;Found:C,60.78;H,3.58;N,7.54。
实施例16:化合物C1-16
本实施例与实施例1基本相同,其不同之处在于,L1配体中的取代基R7不同,产物产率为40%。
ESI-MS[m/z]:1199[M-PF6]+。
元素分析(C75H50F6IrN4P):Anal.Calcd.:C,60.71;H,3.75;N,4.17;Found:C,60.78;H,3.58;N,4.54。
实施例17:铱配合物C2-1的制备
本实施例与实施例1基本相同,其不同之处在于,使用的配体为L2配体,且实施例1中的4,7-二苯基-1,10-菲啰啉换成1,10-菲啰啉,产率40%。
ESI-MS[m/z]:1036[M-PF6]+。
元素分析(C60H39F6IrN6P):Anal.Calcd.:C,61.01;H,3.33;N,7.11;Found:C,61.38;H,3.68;N,7.34。
实施例18:铱配合物C2-2的制备
本实施例与实施例1基本相同,其不同之处在于,使用的配体为L2配体,产率35%。
1H-NMR(600MHz,CDCl3):δ9.60(d,J=10.4Hz,2H),8.75(s,2H),8.60(d,J=7.9Hz,2H),8.48(d,J=5.2Hz,2H),8.29(d,J=8.4Hz,2H),8.09(d,J=8.5Hz,2H),8.01(s,2H),7.81–7.78(m,2H),7.75–7.71(m,2H),7.67(d,J=5.2Hz,2H),7.60–7.55(m,7H),7.49(t,J=7.5Hz,3H),7.45(d,J=7.6Hz,4H),7.35(dt,J=29.2,7.5Hz,8H),7.09(t,J=7.4Hz,2H),6.76(d,J=7.5Hz,2H)。
ESI-MS(m/z):1187[M-PF6]+。
元素分析(IrC72H46N6PF6):Anal.Calcd:C,64.91;H,3.48;N,6.31;Found:C,63.36;H,3.20;N,5.70。
实施例19:铱配合物C2-3的制备方法
本实施例与实施例2基本相同,其不同之处在于,使用的配体为L2配体,产率35%。
1H-NMR(CDCl3,600MHz,δ[ppm]):1.68(s,6H),4.72(s,H),7.41(m,4H),7.51(m,8H),7.67(m,4H),7.79(m,6H),8.16(b,4H),8.74(s,2H)。
ESI-MS[m/z]:955[M+H]+。
元素分析(C53H37N4IrO2):Anal.Calcd.:C,66.72;H,3.91;N,5.87;Found:C,66.78;H,3.88;N,5.84。
实施例20:铱配合物C2-4的制备
本实施例与实施例16基本相同,其不同之处在于,用联吡啶代替1,10-菲啰啉,用Na[Bph4]代替NH4PF6,产率40%。
ESI-MS[m/z]:1012[M-Bph4]+。
元素分析(C82H59BIrN6):Anal.Calcd.:C,73.97;H,4.47;N,6.31;Found:C,73.78;H,4.78;N,6.24。
实施例21:铱配合物C2-5的制备
本实施例与实施例16基本相同,其不同之处在于,用Na[BArF12]代替Na[Bph4],产率40%。
ESI-MS[m/z]:1012[M-BArF12]+。
元素分析(C86H55BF12IrN6):Anal.Calcd.:C,64.42;H,3.46;N,5.24;Found:C,64.68;H,3.78;N,5.54。
实施例22:铱配合物C2-6的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L2配体,且用吡啶甲酸代替乙酰丙酮,产率45%。
ESI-MS[m/z]:978[M+H]+。
元素分析(C54H34IrN5O2):Anal.Calcd.:C,66.38;H,3.51;N,7.17;Found:C,66.78;H,3.88;N,7.34。
实施例23:铱配合物C2-7的制备方法
本实施例与实施例3基本相同,其不同之处在于,配体为L2配体,产率28%。
ESI-MS[m/z]:1187[M+H]+。
元素分析(C72H45IrN6):Anal.Calcd.:C,72.89;H,3.82;N,7.08;Found:C,72.78;H,3.88;N,6.84。
实施例24:铱配合物C2-8的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L2配体,产率32%。
ESI-MS[m/z]:1155[M+H]+。
元素分析(C69H45IrN4O2):Anal.Calcd.:C,71.79;H,3.93;N,4.85;Found:C,71.68;H,3.88;N,4.64。
实施例25:铱配合物C2-9的制备
本实施例与实施例1基本相同,其不同之处在于,配体为L2配体,产率40%。
ESI-MS[m/z]:1387[M-PF6]+。
元素分析(C88H54F6IrN6P):Anal.Calcd.:C,68.96;H,3.55;N,5.48;Found:C,68.78;H,3.88;N,5.74。
实施例26:铱配合物C2-10的制备
本实施例与实施例1基本相同,其不同之处在于,配体为L2配体,产率32%。
ESI-MS[m/z]:1287[M-PF6]+。
元素分析(C80H50F6IrN6P):Anal.Calcd.:C,67.08;H,3.52;N,5.87;Found:C,66.98;H,3.88;N,5.84。
实施例27:铱配合物C2-11的制备
本实施例与实施例1基本相同,其不同之处在于,配体为L2配体,产率25%。
1H-NMR(600MHz,CD2Cl2):δ9.44(d,J=19.4Hz,1H),9.10(d,J=14.3Hz,1H),8.52–8.44(m,1H),8.34(d,J=8.4Hz,1H),8.20(d,J=8.4Hz,1H),8.11(d,J=7.6Hz,1H),7.84–7.80(m,2H),7.79–7.75(m,2H),7.70(t,J=5.1Hz,1H),7.64–7.60(m,3H),7.58–7.54(m,2H),7.40–7.35(m,1H),7.23–7.16(m,1H),6.85–6.80(m,1H)。
ESI-MS(m/z):1211[M-PF6]+。
元素分析(IrC64H38N6S4PF6):Anal.Calcd:C,56.67;H,2.82;N,6.20;Found:C,56.51;H,2.60;N,6.12。
实施例28:铱配合物C2-12的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L2配体,产率15%。
ESI-MS(m/z):979[M+H]+。
元素分析(C45H29IrN4O2S4):Anal.Calcd:C,55.25;H,2.99;N,5.73;Found:C,55.68;H,2.88;N,5.84。
实施例29:铱配合物C2-13的制备
本实施例与实施例3基本相同,其不同之处在于,配体为L2配体,产率35%。
1H-NMR(600MHz,CDCl3):δ9.36(s,1H),8.95(s,1H),8.14(t,J=15.7Hz,1H),8.03(dd,J=23.5,6.4Hz,1H),7.64–7.56(m,3H),7.41(d,J=3.3Hz,1H),7.07(t,J=5.2Hz,1H),6.97(d,J=4.9Hz,1H),6.88(dd,J=18.8,14.0Hz,1H)。
ESI-MS(m/z):1223[M+H]+。
元素分析(C60H33IrN6S6):Anal.Calcd:C,58.95;H,2.72;N,6.87;Found:C,58.78;H,2.88;N,6.74。
实施例30:铱配合物C2-14的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L2配体,产率25%。
ESI-MS(m/z):1179[M+H]+。
元素分析(C61H37IrN4O2S4):Anal.Calcd:C,62.17;H,3.16;N,4.75;Found:C,62.48;H,3.38;N,4.84。
实施例31:化合物C3-1
本实施例与实施例1基本相同,其不同之处在于,将L1配体换为L3配体,产物产率为40%。
ESI-MS[m/z]:1049[M-PF6]+。
元素分析(C61H40F6IrN6P):Anal.Calcd:C,61.35;H,3.38;N,7.04;Found:C,61.48;H,3.50;N,7.34。
实施例32:铱配合物C3-2的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L3配体,产率35%。
1H-NMR(CDCl3,600MHz,δ[ppm]):1.65(s,6H),5.38(s,H),7.41(t,2H),7.50(m,4H),7.67(m,4H),7.79(d,2H),7.84(s,2H),8.01(s,2H),8.16(d,4H),9.20(s,2H)。
ESI-MS[m/z]:803[M+H]+。
元素分析(C41H29N4IrO2):Anal.Calcd.:C,61.41;H,3.65;N,6.99;Found:C,61.40;H,3.61;N,6.95。
实施例33:铱配合物C3-3的制备
本实施例与实施例3基本相同,其不同之处在于,配体为L3配体,产率35%。
ESI-MS[m/z]:959[M+H]+。
元素分析(C54H33IrN6):Anal.Calcd.:C,67.69;H,3.47;N,8.77;Found:C,67.78;H,3.58;N,8.84。
实施例34:铱配合物C3-4的制备
本实施例与实施例2基本相同,其不同之处在于,配体为L3配体,产率15%。
ESI-MS[m/z]:831[M+H]+。
元素分析(C43H33IrN4O2):Anal.Calcd.:C,62.23;H,4.01;N,6.75;Found:C,62.58;H,3.88;N,6.84。
实施例35:铱配合物C3-5的制备
本实施例与实施例3基本相同,其不同之处在于,配体为L3配体,产率28%。
ESI-MS[m/z]:1151[M+H]+。
元素分析(C69H45IrN6):Anal.Calcd.:C,72.04;H,3.94;N,7.31;Found:C,71.78;H,3.88;N,7.64。
实施例36:铱配合物C3-6的制备
本实施例与实施例3基本相同,其不同之处在于,配体为L3配体,产率35%。
ESI-MS[m/z]:1169[M+H]+。
元素分析(C63H39IrN6S3):Anal.Calcd.:C,64.76;H,3.36;N,7.19;Found:C,64.78;H,3.68;N,7.56。
实施例37:铱配合物C3-7的制备
本实施例与实施例3基本相同,其不同之处在于,配体为L3配体,产率30%。
ESI-MS[m/z]:931[M+H]+。
元素分析(C51H37IrN4O2):Anal.Calcd.:C,65.86;H,4.01;N,6.02;Found:C,65.78;H,3.88;N,5.94。
对比例1
本对比例提供一种对比配体以及含该对比配体的对比配合物,该对比配体及该对比配合物的结构分别为:
本发明分别选取基于L1、L2和L3配体的实施例16、18、27以及31与对比例1的配合物进行理论计算。请参阅图2,从图2可以看出,实施例16、18、27以及31中所述铱配合物的Ir-N键更短(依次为 ),而所述对比配合物中的Ir-N键长为可见本发明提供的所述铱配合物键能更大,此外,在所述对比配合物中,所述对比配体与另一辅助配体之间的二面角为79°,而实施例16、18、27和31中的L配体与另一辅助配体之间的二面角更大(89°),这些特征都有利于提高分子稳定性,并进一步提高分子及其有机电致发光器件的发光效率。
请参阅图3,从图3可以看出,所述铱配合物C2-13的热分解温度高达452℃,而所述对比配合物2在368℃下即会发生分解。说明本发明提供的铱配合物具有更高的稳定性,稳定性高的所述铱配合物具有更高的发光效率,而且有利于改善含有该铱配合物的有机电致发光器件的使用寿命。
实施例38:OLED-1的制备
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。
在室温大气氛围下,将聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸(PEDOT:PSS,Bayer AG,CH8000型)与去离子水按1:1的体积比混合均匀,用0.45μm孔径的水性滤头过滤并滴在所述玻璃板上,以3000r/min旋涂60秒,用去离子水擦出阴极和阳极,传入氮气氛围的手套箱内,在200℃的热板上烘干10分钟以除去溶剂,最终膜厚为40~45nm。当基片完全冷却后可继续进行有机发光层的旋涂,将所述铱配合物C2-2(20%)与主体材料PVK用1,2-二氯乙烷溶解后,以1500~2000r/min旋涂30秒,在80℃的热板上干燥半小时。
把上述玻璃板置于真空腔内,抽真空至1×10-5~1×10-3Pa,真空蒸镀Cs2CO3提高电子注入性能,蒸镀速率为0.02nm/s,蒸镀膜厚为2.3nm;在Cs2CO3之上真空蒸镀一层Al作为阴极,蒸镀速率为0.5nm/s,蒸镀膜厚为1500nm。并在有机发光层和阴极之间增加一层既可以改善电子传输性能又能起激子阻挡作用的TPBi。
实施例39:OLED-2的制备
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。
把上述带有阳极的玻璃板置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm。
在空穴传输层之上真空蒸镀一层掺杂所述铱配合物C1-2的Ga2(saph)2q2作为器件的有机发光层,所述铱配合物C1-2与Ga2(saph)2q2的蒸镀速率比为2:10,C1-2在Ga2(saph)2q2中的掺杂浓度为20wt%,其蒸镀总速率为0.1nm/s,蒸镀总膜厚为40nm。
在有机发光层上真空蒸镀一层TPBi材料作为器件的电子传输层,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm。
在电子传输层上依次真空蒸镀Mg:Ag合金层和Ag层作为器件的阴极,其中Mg:Ag合金层的蒸镀速率为2.0~3.0nm/s,厚度为100nm,Ag层的蒸镀速率为0.3nm/s,厚度为100nm。
实施例40:OLED-3的制备
本实施例与实施例38基本相同,其不同之处在于,所述铱配合物为C2-3。
实施例41:OLED-4的制备
本实施例与实施例38基本相同,其不同之处在于,所述铱配合物为C2-9。
实施例42:OLED-5的制备
本实施例与实施例39基本相同,其不同之处在于,所述铱配合物为C2-3。
实施例43:OLED-6的制备
本实施例与实施例39基本相同,其不同之处在于,所述铱配合物为C2-6。
表1
从表1以及图4可以看出,本发明提供的有机电致发光器件可以发出纯正的近红外光,所述有机电致发光器件的量子外发光效率可达到2%,辐射出射度均在700uW/m2(20V)以上。从图5、图6及图7可以看出,在大电流密度条件下,所述有机电致发光器件仍然保持较高的外量子效率,且效率滚降效应很小。
此外,在所述有机电致发光器件制备过程中,通常需要通过真空蒸镀、化学气相沉积等方法将发光材料蒸镀在基板上形成所述有机发光层,而真空蒸镀、化学气相沉积等方法通常都是在一定温度条件下进行的,由于所述对比配合物的稳定性差,因此所述对比配合物在所述有机电致发光器件的制备过程中会有相当一部分发生分解,从而使所述对比配合物的利用率大大降低,并且含有该对比配合物的有机电致发光器件也具有不稳定、使用寿命短等缺点。而本发明提供的所述铱配合物在所述有机电致发光器件制备过程不会发生分解,使所述铱配合物的利用率大大提高,且含有该铱配合物的有机电致发光器件较稳定、具有较长的使用寿命。
尽管结合优选实施例对本发明进行了说明,但本发明并不局限于上述实施例和附图。另外,本领域技术人员还可在本发明精神内做其他变化,当然,这些依据本发明精神所做的变化,都应包含在本发明所要求保护的范围之内。
Claims (10)
1.一种用作近红外发光材料的铱配合物,该铱配合物的结构通式为LnIrX3-n或[LnIrX3-n]+Z-,其中,Ir是所述铱配合物的中心原子,L与X均为所述铱配合物的配体,Z-为阴离子,n=1,2或3,L选自具有以下通式的L1配体、L2配体或L3配体:
其中,R1~R8分别独立地选自氢原子、碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、碳原子数为1~10的烷基氨基、咔唑基、氟原子、三氟甲基和碳原子数为5~18的芳香基团中的一种,Ar选自碳原子数为5~18的芳基和碳原子数为5~18的杂环芳基。
2.如权利要求1所述用作近红外发光材料的铱配合物,其特征在于,X选自联吡啶、1,10-菲啰啉、4,7-二苯基-1,10-菲啰啉、乙酰丙酮、二苯甲酰基甲烷、二叔戊酰甲烷和吡啶甲酸中的一种。
3.如权利要求1所述用作近红外发光材料的铱配合物,其特征在于,Z-选自氯离子,六氟磷酸根、高氯酸根、四苯基硼酸根以及四(对三氟甲基苯基)硼酸根中的一种。
4.如权利要求1所述用作近红外发光材料的铱配合物,其特征在于,所述铱配合物选自下列结构式的一种:
5.一种有机电致发光器件,包括一阳极、一空穴传输层、一有机发光层、一电子传输层以及一阴极,其特征在于,所述有机发光层包括权利要求1到权利要求4中任意一项所述铱配合物。
6.如权利要求5所述的有机电致发光器件,其特征在于,所述铱配合物占所述有机发光层总质量的1%~30%。
7.如权利要求5所述的有机电致发光器件,其特征在于,所述有机发光层进一步包括一主体材料,所述主体材料通过接收空穴和电子产生激子,然后向所述铱配合物转移激子的能量。
8.如权利要求7所述的有机电致发光器件,其特征在于,所述主体材料选自含咔唑类共轭小分子、芳基硅类小分子以及金属配合物中的一种或几种。
9.如权利要求5所述的有机电致发光器件,其特征在于,所述阳极、空穴传输层、有机发光层、电子传输层以及阴极依次层叠设置。
10.如权利要求9所述的有机电致发光器件,其特征在于,所述有机电致发光器件进一步包括一空穴阻挡层,所述空穴阻挡层设置在所述有机发光层与所述电子传输层之间。
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