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US 10,065,959 B2Granted
Electronic device
AssigneeMerck Patent GmbH
InventorsJunyou Pan, Amir Hossain Parham, Rene Peter Scheurich, Thomas Rudolph
Life of this patent
Estimating the term…
Abstract
The present application relates to an electronic device comprising a heteroaromatic compound of a formula (I) as functional material, in particular as electron-transport material and as matrix material for emitter compounds.
Claims14
An electronic device comprising an anode, a cathode, and at least one organic layer comprising at least one compound of formula (I):
- wherein
- E is selected on each occurrence, identically or differently, from a single bond, B(R1), C═O, N(R1), P(R1), P(═O)R1, O, S, S═O, and S(═O)2, wherein both groups E cannot be a single bond;
- T is on each occurrence, identically or differently, CR1 or N;
- W is N;
- Y is N(R1), O, or S;
- Z is on each occurrence, identically or differently, CR2 or N;
- R1 is on each occurrence, identically or differently, H, D, F, C(═O)R3, CN, Si(R3)3, N(R3)2, P(═O)(R3)2, S(═O)R3, S(═O)2R3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R3, wherein one or more CH2 groups in said groups are optionally replaced by C═NR3, C(═O)O —R3C═CR3—, —C≡C—, Si(R3)2, C═O, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3;
- R2 is on each occurrence, identically or differently, H, D, F, C(═O)R3, CN, Si(R3)3, N(R3)2, P(═O)(R3)2, S(═O)R3, S(═O)2R3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R3, wherein one or more CH2 groups in said groups are optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, and wherein two or more radicals R2 are optionally linked to one another and optionally define an aliphatic or heteroaliphatic ring;
- R3 is on each occurrence, identically or differently, H, D, F, C(═O)R4, CN, Si(R4)3, N(R4)2, P(═O)(R4)2, S(═O)R4, S(═O)2R4, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R4, wherein one or more CH2 groups in said groups are optionally replaced by —R4C═CR4—, —C≡C—, Si(R4)2, C═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(═O)(R4), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R4, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R4, and wherein two or more radicals R3 are optionally linked to one another and optionally define a ring;
- R4 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F;
- and wherein two or more substituents R4 are optionally linked to one another and optionally define a ring;
- n is 0 or 1;
- wherein at least one group R1 or R2 in the compound of formula (I) is selected from an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R3.
10 more elements
A compound of formula (I-1):
- wherein
- E2 is on each occurrence, identically or differently, a single bond, C═O, N(R1), O, or S, wherein both groups E2 cannot be a single bond;
- T is on each occurrence, identically or differently, CR1 or N;
- Y is N(R1), O, or S;
- Z is on each occurrence, identically or differently, CR2 or N;
- R1 is on each occurrence, identically or differently, H, D, F, C(═O)R3, CN, Si(R3)3, N(R3)2, P(═O)(R3)2, S(═O)R3, S(═O)2R3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R3, wherein one or more CH2 groups in said groups are optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3;
- R2 is on each occurrence, identically or differently, H, D, F, C(═O)R3, CN, Si(R3)3, N(R3)2, P(═O)(R3)2, S(═O)R3, S(═O)2R3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R3, wherein one or more CH2 groups in said groups are optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, C═O, C═NR3, —C(═O)O—, —C(═O)NR3—, NR3, P(═O)(R3), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, and wherein two or more radicals R2 are optionally linked to one another and optionally define an aliphatic or heteroaliphatic ring;
- R3 is on each occurrence, identically or differently, H, D, F, C(═O)R4, CN, Si(R4)3, N(R4)2, P(═O)(R4)2, S(═O)R4, S(═O)2R4, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein said groups are optionally substituted by one or more radicals R4, wherein one or more CH2 groups in said groups are optionally replaced by —R4C═CR4—, —C≡C—, Si(R4)2, C═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(═O)(R4), —O—, —S—, SO, or SO2, and wherein one or more H atoms in said groups are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R4, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R4, and wherein two or more radicals R3 are optionally linked to one another and optionally define a ring;
- R4 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F;
- and wherein two or more substituents R4 are optionally linked to one another and optionally define a ring;
- n is 0 or 1;
- wherein at least one group R1 or R2 in the compound of formula (I) is selected from an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R3;
- and
- wherein at least one group R1 is selected from groups of formulae (Het-a) to (Het-e):
- wherein
- Ar1 is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R3;
- V is on each occurrence, identically or differently, N or CR3;
- k is 0 or 1;
- the dashed line denotes the bond to the remainder of the compound;
- and
- wherein at least one group V in the ring in formula (Het-a), (Het-d), and (Het-e) is N.
18 more elements
Dependencies are inferred from the claim text.