Organic electroluminescent device
View Patent ↗The present invention relates to compounds of the general formula (S-A)n-T, in which at least one fluorescent group S is linked to a phosphorescent group T via a divalent group A, to the use thereof in an electronic device, and to a formula to a formulation and an electronic device which comprise the novel compounds.
1. A compound of the general formula (1):
(S-A) n -T formula (1),
where the symbols and indices used have the following meaning:
S is on each occurrence, independently of one another, a monovalent group which includes a fluorescent emitter unit;
T is an n-valent group which includes a phosphorescent emitter unit;
A represents on each occurrence, independently of one another, a divalent unit selected from the group consisting of divalent units of the general formulae (240) to (254),
where Ar 1 , Ar 2 and Ar 3 each, independently of one another, denote a mono- or polycyclic aromatic unit having 6 to 20 ring atoms or a mono- or polycyclic heteroaromatic unit having 5 to 20 ring atoms, two of the radicals R 1 to R 4 or one of the radicals R 1 to R 4 and one of the groups Ar 1 , Ar 2 and Ar 3 have a bond to S or T of the compound of the general formula (1), and where R 1 , R 2 , R 3 and R 4 each, independently of one another, denote alkyl(ene), cycloalkyl(ene), alkylsilyl(ene), silyl(ene), arylsilyl(ene), alkylalkoxy-alkyl(ene), arylalkoxyalkyl(ene), alkylthioalkyl(ene), phosphine, phosphine oxide, sulfone, alkylene sulfone, sulfone oxide, alkylene sulfone oxide, where the alkylene group in each case, independently of one another, has 1 to 12 C atoms and where one or more H atoms may be replaced by F, Cl, Br, I, alkyl or cycloalkyl, where one or more CH 2 is optionally replaced by a heteroatom or an aromatic or heteroaromatic hydrocarbon radical having 5 to 20 aromatic ring atoms;
n is 1, 2, 3, 4, or 5;
wherein the phosphorescent emitter unit is a metal-ligand coordination compound which includes a metal selected from the group consisting of Ir, Zn, Cu, Os, Ru, Pd, Pt, Re, Au, Mo, W, Rh and Eu and a ligand selected from the group consisting of formulae (34) through (39) and (34a) through (39a)
where:
R is identical or different on each occurrence and is selected from the group consisting of alkyl(ene), cycloalkyl(ene), alkylsilyl(ene), silyl(ene), arylsilyl(ene), alkylalkoxyalkyl(ene), arylalkoxyalkyl(ene), alkylthio-alkyl(ene), phosphine, phosphine oxide, sulfone, alkylene sulfone, sulfoxide and alkylene sulfoxide, where the alkylene group in each case has, independently of one another, 1 to 12 C atoms and where one or more H atoms is optionally replaced by F, Cl, Br, I, alkyl or cycloalkyl, where one or more CH 2 is optionally replaced by NH, O or S, or an aromatic or heteroaromatic hydrocarbon radical having 5 to 20 aromatic ring atoms;
m is on each occurrence, independently of one another, 0, 1, 2, 3 or 4;
n is on each occurrence, independently of one another, 0, 1, or 2;
o is on each occurrence, independently of one another, 0, 1, 2 or 3;
wherein S is selected from the group consisting of styrylamine, indenofluorene, tetracene, xanthene, perylene, phenylene, fluorene, arylpyrene, arylenevinylene, rubrene, coumarine, rhodamine, quinacridone, dicyanomethylenepyran, thiopyran, polymethine, pyrylium and thiapyrylium salts, periflanthene, indenoperylene, bis(azinyl)imineboron compounds, bis(azinyl)methine compounds, carbostyryl compounds, monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers, arylamines, indenofluorenamines and indenofluorenediamines, benzoindenofluorenamines, benzoindenofluorenediamines, dibenzoindenofluorenamines, dibenzoindenofluorenediamines, substituted or unsubstituted tristilbenamines, distyrylbenzene and distyrylbiphenyl, triarylamines, naphthalene, anthracene, tetracene, periflanthene, indenoperylene, phenanthrene, perylene, pyrene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene, pyran, oxazone, benzoxazole, benzothiazole, benzimidazole, pyrazine, cinnamic acid esters, diketopyrrolopyrrole, acridone, and combinations thereof.
2. The compound according to claim 1 , wherein S is selected from the group consisting of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphophines, styryl ethers, arylamines, indenofluorenamines, and indenofluorenediamines.
3. The compound according to claim 1 , wherein A is one of the following divalent units:
in which the dashed lines represent bonds to the groups S and T, and W and Z are selected, independently of one another, from the group consisting of C 1-12 -alkyl, a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon radical having 5 to 20 ring atoms.
4. The compound according to claim 1 , wherein n is equal to 1, 2 or 3.
5. The compound according to claim 1 , wherein an emission band of the fluorescent emitter unit has an emission maximum in the wavelength range from 500 to 750 nm.
6. The compound according to claim 1 , wherein an absorption band of the fluorescent emitter unit has an absorption maximum in the wavelength range from 400 to 600 nm.
7. The compound according to claim 1 , wherein an emission band of the phosphorescent emitter unit has an emission maximum in the wavelength range from 400 to 600 nm.
8. The compound according to claim 1 , wherein an absorption band of the fluorescent emitter unit has a wavelength range which overlaps with an emission band of the phosphorescent emitter unit.
9. The compound according to claim 1 , wherein an emission band of the fluorescent emitter unit has a wavelength range which overlaps with an absorption band of the phosphorescent emitter unit.
10. An electronic device which comprises the compound according to claim 1 .
11. An organic electroluminescent device comprising the compound according to claim 1 .
12. The organic electroluminescent device as claimed in claim 11 , wherein the device is an organic light-emitting diode, an organic light-emitting electrochemical cell or an organic light-emitting transistor.
13. The electronic device according to claim 10 , wherein the device is an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic solar cell, a dyesensitised organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, an organic laser diode or an organic plasmon emitting device.
14. A formulation comprising at least one compound according to claim 1 and at least one solvent.