Organic electronic device
AssigneeMerck Patent GmbH
InventorEsther Breuning
Life of this patent
Estimating the term…
Abstract
The present invention relates to organic electroluminescent devices which comprise aromatic nitrogen heterocyclic compounds, in particular in a hole-injection layer and/or in a hole-blocking layer and/or in an electron-transport layer and/or in an emitting layer.
Claims19
An organic electronic device comprising a cathode, an anode and at least one organic layer, which is arranged between the cathode and anode and which comprises at least one compound of the formula (1) or formula (2):
- where the following applies to the symbols and indices used:
- X is on each occurrence, identically or differently, CR1 or N;
- Y is on each occurrence, identically or differently, a divalent group selected from the group consisting of B(R1)2, C(R1)2, NR1, O, S, C(═O), C═C(R1)2, S(═O), S(═O)2, P(═O)(R1)2, and a divalent aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which is optionally substituted by one or more radicals R1;
- R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R1)2, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR1═CR1Ar, CN, NO2, Si(R1)3, B(OR1)2, B(R1)2, B(Ar)2, B(N(R1)2)2, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or a combination of these systems;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R2)2, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1;
- two radicals Ar which are bonded to the same nitrogen or phosphorus atom which is optionally linked to one another here by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S═O, SO2, N(R2), P(R2) and P(═O)R2;
- R2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F;
- two or more adjacent substituents R2 here optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- n is 0, 1, 2, 3, 4, 5 or 6;
- m is 0, 1, 2 or 3;
- p is on each occurrence, identically or differently, 0, 1, 2 or 3 and
- wherein the compounds of the formula (1) or formula (2) are employed as electron-transport material or as hole-blocking material in an electron-transport layer or hole-blocking layer or as charge-generation material in a charge-generation layer and wherein the organic electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O—SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs) and organic laser diodes (O-lasers).
An organic electronic device comprising at least one oligomer, polymer or dendrimer which comprises one or more compounds of the formulae (1) to (6)
- where the following applies to the symbols and indices used:
- X is on each occurrence, identically or differently, CR1 or N;
- Y is on each occurrence, identically or differently, a divalent group selected from the group consisting of B(R1)2, C(R1)2, NR1, O, S, C(═O), C═C(R1)2, S(═O), S(═O)2, P(═O)(R1)2, and a divalent aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which is optionally substituted by one or more radicals R1;
- R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R1)2, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(˜0)Ar, S(═O)2Ar, CR1═CR1Ar, CN, NO2, Si(R1)3, B(OR1)2, B(R1)2, B(Ar)2, B(N(R1)2)2, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R1, where one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or a combination of these systems;
- R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R2)2, N(Ar)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR2═CR2Ar, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R1;
- two radicals Ar which are bonded to the same nitrogen or phosphorus atom which is optionally linked to one another here by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S═O, SO2, N(R2), P(R2) and P(═O)R2;
- R2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F;
- two or more adjacent substituents R2 here optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- n is 0, 1, 2, 3, 4, 5 or 6;
- m is 0, 1, 2 or 3;
- p is on each occurrence, identically or differently, 0, 1, 2 or 3, where one or more radicals R represent bonds from the compound of the formulae (1) to (6) to the polymer, oligomer or dendrimer wherein the compounds of the formulae (1) to (6) are employed as electron-transport material or as hole-blocking material in an electron-transport layer or hole-blocking layer or as charge-generation material in a charge-generation layer, and
- wherein the organic electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (G-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs) and organic laser diodes (O-lasers).
Dependencies are inferred from the claim text.