Electroluminescent devices comprising diketopyrrolopyrroles
AssigneeCiba Specialty Chemicals Corporation
InventorsJunji Otani, Hiroshi Yamamoto, Norihisa Dan, Abul Iqbal, Robert Moretti
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Abstract
Electroluminescent device comprising in this order (a) an anode (b) a hole transporting layer (c) a light-emitting layer (d) optionally an electron transporting layer and (e) a cathode and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole represented by formula I or formula III processes for the preparation of compounds I, its uses and compositions comprising the compounds I and/or III.
Claims7
Electroluminescent device comprising in this order
- (a) an anode
- (b) a hole transporting layer
- (c) a light-emitting layer
- (d) optionally an electron transporting layer and
- (e) a cathode
- and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole (“DPP”) represented by formula I or formula III
- wherein R1 and R2, independently from each other, stand for C1–C25-alkyl, allyl which can be substituted one to three times with C1–C3alkyl or Ar3, or —CR3R4—(CH2)m—Ar3, wherein R3 and R4 independently from each other stand for hydrogen, C1–C4alkyl, or phenyl which can be substituted one to three times with C1–C3 alkyl,
- Ar3 stands for phenyl or 1- or 2-naphthyl which can be substituted one to three times with C1–C8alkyl, C1–C8alkoxy, halogen or phenyl, which can be substituted with C1–C8alkyl or C1–C8alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4,
- Ar1 and Ar2, independently from each other, stand for
- or phenanthryl, 2- or 9-fluorenyl, or anthracenyl,
- wherein
- R5, R6 and R7, independently from each other, stand for hydrogen, cyano, halogen, C1–C6alkyl, —NR8R9, —OR10, —S(O)nR8, —Se(O)nR8, or phenyl, which can be substituted one to three times with C1–C8aIkyl or C1–C8alkoxy,
- wherein R8 and R9, independently from each other, stand for hydrogen, phenyl, C1–C25-alkyl, C5–C12-cycloalkyl, —CR3R4—(CH2)m-Ph, R10, wherein R10 stands for C6–C24-aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein Ph, the aryl and heterocyclic radical can be substituted one to three times with C1–C8alkyl, C1–C8alkoxy, or halogen, or R8 and R9 stand for —C(O)R11, wherein R11 can be C1–C25-alkyl, C5–C12-cycloalkyl, R10, —OR12 or —NR13R14, wherein R12, R13, and R14 stand for C1–C25-alkyl, C5–C12-cycloalkyl, C6–C24-aryl,
- or R5, R6 and R7 stand for
- a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the heterocyclic radical can be substituted one to three times with C1–C8alkyl or C1–C8alkoxy, or —NR8R9 stands for a five- or six membered heterocyclic radical in which R8 and R9 together stand for tetramethylene, pentamethylene, —CH2—CH2—O—CH2—CH2—, or —CH2—CH2—NR50—CH2—CH2—, wherein R50 stands for hydrogen, C1–C6alkyl, phenyl or phenyl substituted one to three times with C1–C8alkyl or C1–C8alkoxy
- and n stands for 0, 1, 2 or 3,
- and wherein Z stands for a diradical selected from the group consisting of a single bond, C2–C6alkylene, which can be substituted one to three times with C1–C4alkyl, C1–C4alkoxy, or phenyl, phenylene or naphthylene.
An electroluminescent device comprising in this order
- (a) an anode
- (b) a hole transporting layer
- (c) a light-emitting layer
- (d) optionally an electron transporting layer and
- (e) a cathode
- and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole (“DPP”) represented by formula I
- wherein
- R1 and R2 are C1–C8alkyl, or —(CH2)m-Ph, Ar1 and Ar2 are a group of formula
- wherein R7 is —N(R8)2, wherein R8 is unsubstituted or substituted phenyl, unsubstituted or substituted heterocyclic radical or C5–C12-cycloalkyl, and m stands for 0, 1, 2, 3 or 4.
An electroluminescent device comprising in this order
- (a) an anode
- (b) a hole transporting layer
- (c) a light-emitting layer
- (d) optionally an electron transporting layer and
- (e) a cathode
- and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole (“DPP”) represented by formula I
- wherein
- R1 and R2 are —CH2-Ph, wherein phenyl can be substituted with phenyl, naphthyl or C1–C4alkyl up to two times, Ar1 and Ar2 are a group of formula
- wherein R7 is hydrogen or OMe.
Dependencies are inferred from the claim text.