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US 2010/0141120 A1Published application
Oligomers of Isonitrile-Metal Complexes as Triplett Emitters for OLED Applications
AssigneeNovaled GmbH
InventorsHartmut Yersin, Uwe Monkowius, Tobias Fischer, Walter Finkenzeller, Rafal Czerwieniec
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Abstract
The present invention relates to light-emitting devices and in particular organic light-emitting devices (OLEDs). In particular, the invention relates to the use of luminescent isonitrile/metal complexes as oligomer emitters in devices of this type.
Claims35
Light-emitting device comprising
- (i) an anode,
- (ii) a cathode and
- (iii) an emitter layer, arranged between and in direct or indirect contact with the anode and cathode, comprising at least one complex of the formula (I)
- (NC)nM(CNR)m
- in which M represents Pt(II), Pd(II), Rh(I), Ir(I) or Au(III),
- R represents a hydrocarbon group, which may optionally contain heteroatoms,
- n=0 to 4 and
- m=0 to 4,
- where the proportion of complexes of the formula (I) in the emitter layer is more than 10% by weight, based on the total weight of the emitter layer.
6 more elements
Light-emitting device according to one of the preceding claims,
- characterised in that
- it is insulated from the environment, so that ingress of gas from the environment into the emitter layer cannot occur.
Light-emitting device according to one of the preceding claims,
- characterised in that
- M in formula (I) represents Pt(II) or Pd(II).
Light-emitting device according to one of the preceding claims,
- characterised in that
- R represents an alkyl, alkenyl, alkynyl, aryl, heteroaryl or —SO2R′ group, which may optionally contain one or more functional groups, in particular a phenyl, epoxide, cyclic ether, cyanate, alcohol, carboxylate, amine, halogen, organoboric acid, olefin or halogen group, where R′ represents a hydrocarbon group, which may optionally contain heteroatoms.
Light-emitting device according to one of the preceding claims,
- characterised in that
- two radicals CNR together form a radical CN—R″—NC, where R″ is selected from alkylene, alkenylene, alkynylene, arylene, heteroarylene, where R″ may optionally contain one or more heteroatoms.
Light-emitting device according to one of the preceding claims,
- characterised in that
- n and/or m represent an integer and in particular
- n+m=4.
Light-emitting device according to one of the preceding claims,
- characterised in that
- n=m=2.
Light-emitting device according to one of the preceding claims,
- characterised in that
- the complex of the formula (I) in the emitter layer is bonded to a polymer.
Light-emitting device according to one of the preceding claims,
- characterised in that
- it comprises, as emitter, the compound
- dicyanobis(isopropylisocyanide)platinum(II), Pt(CN)2(i-C3H7NC)2
- dicyanobis(n-butylisocyanide)platinum(II), Pt(CN)2(n-C4H9NC)2
- dicyanobis(cyclohexylisocyanide)platinum(II), Pt(CN)2(C6H11NC)2
- dicyanobis((S)-(−)-α-methylbenzylisocyanide)platinum(II), Pt(CN)2(C8H9NC)2
- dicyanobis(tert-butylisocyanide)palladium(II), Pd(CN)2(t-C4H9NC)2
- dicyanobis(isopropylisocyanide)palladium(II), Pd(CN)2(i-C3H7NC)2
- dicyanobis(methylisocyanide)platinum(II), Pt(CN)2(CH3NC)2
- dicyanobis(ethylisocyanide)platinum(II), Pt(CN)2(C2H5NC)2 and/or
- dicyanobis(tert-butylisocyanide)platinum(II), Pt(CN)2(t-C4H9NC)2
- dicyanobis(3-isocyanopropyltriethoxysilane)platinum(II), Pt(CN)2((OEt)3SiC3H6NC)2
- dicyanobis(1,3-diisocyanopropane)platinum(II), Pt(CN)2(CNCH2CH2CH2NC)2
- dicyanobis(2,5-dimethylphenylisocyanide)platinum(II), Pt(CN)2(C8H9NC)2
- dicyanobis(3,3-difluorophenylisocyanide)platinum(II), Pt(CN)2(C6H3F2NC)2
- dicyanobis(3-isocyanomethylpyridine)platinum(II), Pt(CN)2(C5H4NCH2NC)2
- dicyanobis(2,2,2-trifluoroethylisocyanide)platinum(II), Pt(CN)2—(CF3CH2CH2NC)2.
14 more elements
Light-emitting device according to one of the preceding claims,
- characterised in that
- it comprises at least two different complexes of the formula (I).
Light-emitting device according to one of the preceding claims,
- characterised in that
- complexes of the formula (I) are present in a columnar structure in the emitter layer.
Light-emitting device according to one of the preceding claims,
- characterised in that
- it is a display and/or a lighting device.
Use of a complex of the formula (I) as emitter in a light-emitting device.
Complex selected from
- dicyanobis(isopropylisocyanide)platinum(II), Pt(CN)2(i-C3H7NC)2
- dicyanobis(n-butylisocyanide)platinum(II), Pt(CN)2(n-C4H9NC)2
- dicyanobis(cyclohexylisocyanide)platinum(II), Pt(CN)2(C6H11NC)2
- dicyanobis((S)-(−)-α-methylbenzylisocyanide)platinum(II), Pt(CN)2(C8H9NC)2
- dicyanobis(tert-butylisocyanide)palladium(II), Pd(CN)2(t-C4H9NC)2
- dicyanobis(isopropylisocyanide)palladium(II), Pd(CN)2(i-C3H7NC)2
- dicyanobis(isopropylisocyanide)palladium(II), Pd(CN)2(i-C3H7NC)2
- dicyanobis(methylisocyanide)platinum(II), Pt(CN)2(CH3NC)2
- dicyanobis(2,5-dimethylphenylisocyanide)platinum(II), Pt(CN)2(C8H9NC)2
- dicyanobis(1,3-diisocyanopropane)platinum(II), Pt(CN)2(CNCH2CH2CH2NC)
- dicyanobis(3,4-difluorophenylisocyanide)platinum(II), Pt(CN)2(C6H3F2NC)2
- dicyanobis(3-isocyanomethylpyridine)platinum(II), Pt(CN)2(C5H4NCH2NC)2
- dicyanobis(2,2,2-trifluoroethylisocyanide)platinum(II), Pt(CN)2(CF3CH2NC)2
- dicyanobis(methoxymethylisocyanide)platinum(II), Pt(CN)2(CH3OCH2NC)2
- dicyanobis(4-fluorophenylisocyanide)platinum(II), Pt(CN)2(C6H4FNC)2
- dicyanobis(4-methoxyphenylisocyanide)platinum(II), Pt(CN)2(CH3OC6H4NC)2
- dicyanobis(4-isocyanoacetophenone)platinum(II), Pt(CN)2(CH3COC6H4NC)2
- dicyanobis(2-naphthylisocyanide)platinum(II), Pt(CN)2(C10H7NC)2
- dicyanobis(4-chlorophenylisocyanide)platinum(II), Pt(CN)2(C6H4CINC)2
- dicyanobis(4-bromophenylisocyanide)platinum(II), Pt(CN)2(C6H4CINC)2
- dicyanobis(4-nitrophenylisocyanide)platinum(II), Pt(CN)2(O2NC6H4NC)2
- dicyanobis(methyl-3-isocyano-4-methylbenzoate)platinum(II), Pt(CN)2(C9H9O2NC)2
- dicyanobis(4-isocyanobenzotrifluoride)platinum(II), Pt(CN)2(CF3C6H4NC)2
- dicyanobis(4-(methylthio)phenylisocyanide)platinum(II), Pt(CN)2(CH3SC6H4NC)2
- dicyanobis(4-methylphenylisocyanide)platinum(II), Pt(CN)2(CH3C6H4NC)2
- dicyanobis(4-tert-butylphenylisocyanide)platinum(II), Pt(CN)2((CH3)3CC6H4NC)2
- dicyanobis(3,4,5-trimethoxyphenylisocyanide)platinum(II), Pt(CN)2(C9H11O3NC)2
- dicyanobis(4-formylaminophenylisocyanide)platinum(II), Pt(CN)2(C7H6NONC)2
- dicyanobis(4-butoxyphenylisocyanide)platinum(II), Pt(CN)2(C4H9OC6H4NC)2
- dicyanobis(4-(trifluoromethoxy)phenylisocyanide)platinum(II), Pt(CN)2(CF3OC6H4NC)2
- dicyanobis(4-vinylphenylisocyanide)platinum(II), Pt(CN)2(C8H7NC)2
- dicyanobis(1-cyclohexenylisocyanide)platinum(II), Pt(CN)2(C6H9NC)2
- dicyanobis(2-(thien-2-yl)ethylisocyanide)platinum(II), Pt(CN)2(C6H7SNC)2
- dicyanobis(5-methylfurfurylisocyanide)platinum(II), Pt(CN)2(C6H7ONC)2
- dicyanobis(N-(2-isocyanoethyl)imidazole)platinum(II), Pt(CN)2(C6H7N2NC)2
- dicyanobis(6-isocyanoquinolino)imidazole)platinum(II), Pt(CN)2(C9H6NNC)2
- dicyanobis(4-isocyanomethylpyridine)platinum(II), Pt(CN)2(C5H4NCH2NC)2
- dicyanobis(allylisocyanide)platinum(II), Pt(CN)2(C3H6NC)2
- dicyanobis(2-isocyanoethyltosylate)platinum(II), Pt(CN)2(C9H11O3SNC)2
- dicyanobis(propylisocyanide)platinum(II), Pt(CN)2(C3H7NC)2
- dicyanobis(2-(morpholino)cyanoethane)platinum(II), Pt(CN)2(CNCH2C4H8NO)2
- dicyanobis(2-(thiazolidino)cyanoethane)platinum(II), Pt(CN)2(CNCH2C3H6S)2
- dicyanobis(2-(methylpiperazino)cyanoethane)platinum(II), Pt(CN)2(CNCH2C5H11N2)2
- dicyanobis(2-(ethylenedioxypiperazino)cyanoethane)platinum(II), Pt(CN)2(CNCH2C6H12N2O2)2
- dicyanobis(1-isocyanoindane)platinum(II), Pt(CN)2(CNC9H9)2
- dicyanobis(4-methoxybenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C6H4OCH3)2
- dicyanobis(1-isocyano-1,2,3,4-tetrahydronaphthalene)platinum(II), Pt(CN)2(CNC10H11)2
- dicyanobis(5-isocyanomethylbenzo[4,5]-1,3-dioxolane)platinum(II), Pt(CN)2(CNCH2C7H5O2)2
- dicyanobis(4-tert-butylbenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C10H13)2
- dicyanobis(3,5-dimethylbenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C8H9)2
- dicyanobis(3-methoxybenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C7H7O)2
- dicyanobis(1-(4-fluorophenyl)methylisocyanide)platinum(II), Pt(CN)2(CNCH2C6H4F)2
- dicyanobis(4-(trifluoromethoxy)benzylisocyanide)platinum(II), Pt(CN)2(CNCH2C7H4F3O)2
- dicyanobis(2,6-difluorobenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C6H3F2)2
- dicyanobis(2-(trifluoromethyl)benzylisocyanide)platinum(II), Pt(CN)2(CNCH2C7H4F3)2
- dicyanobis(4-(trifluoromethyl)benzylisocyanide)platinum(II), Pt(CN)2(CNCH2C7H4F3)2
- dicyanobis(3,4,5-trimethoxybenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C9H11O3)3
- dicyanobis(triphenylisocyanomethane)platinum(II), Pt(CN)2(CNC19H15)2
- dicyanobis(2,6-dichlorobenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C6H3Cl3)2
- dicyanobis(2,3-dimethylbenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C8H9)2
- dicyanobis(4-trifluoromethylbenzylisocyanide)platinum(II), Pt(CN)2(CNCH2C6H4CF3)2
- dicyanobis(cycloheptylisocyanide)platinum(II), Pt(CN)2(CNC7H14)2
- dicyanobis(isocyanooctane)platinum(II), Pt(CN)2(CNC8H17)2
- dicyanobis(1-isocyano-3-isopropoxypropane)platinum(II), Pt(CN)2(CNC6H13O)2
- dicyanobis(3,3-dimethylbut-1-ylisocyanide)platinum(II), Pt(CN)2(CNC6H13O)2.
62 more elements
Dependencies are inferred from the claim text.