Electronic device

Patent metadata

Field	Value
Publication number	US-10065959-B2
Application number	US-201314648409-A
Country	US
Kind code	B2
Filing date	Nov 4, 2013
Priority date	Nov 30, 2012
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

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.

First claim

The invention claimed is:

1. 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(R 1 ), C═O, N(R 1 ), P(R 1 ), P(═O)R 1 , 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, CR 1 or N;
W is N;
Y is N(R 1 ), O, or S;
Z is on each occurrence, identically or differently, CR 2 or N;
R 1 is on each occurrence, identically or differently, H, D, F, C(═O)R 3 , CN, Si(R 3 ) 3, N(R 3 ) 2 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , 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 R 3 , wherein one or more CH 2 groups in said groups are optionally replaced by C═NR3, C(═O)O —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , 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 R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 3 ;
R 2 is on each occurrence, identically or differently, H, D, F, C(═O)R 3 , CN, Si(R 3 ) 3, N(R 3 ) 2 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , 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 R 3 , wherein one or more CH 2 groups in said groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , 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 R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 3 , and wherein two or more radicals R 2 are optionally linked to one another and optionally define an aliphatic or heteroaliphatic ring;
R 3 is on each occurrence, identically or differently, H, D, F, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , 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 R 4 , wherein one or more CH 2 groups in said groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , 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 R 4 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 4 , and wherein two or more radicals R 3 are optionally linked to one another and optionally define a ring;
R 4 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 R 4 are optionally linked to one another and optionally define a ring;
n is 0 or 1;
wherein at least one group R 1 or R 2 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 R 3 .

2. The electronic device of claim 1 , wherein at least one group R 1 or R 2 in the compound of formula (I) is selected from a group comprising at least one of the following groups:
heteroaryl groups having 5 to 20 aromatic ring atoms which comprise at least one heteroaromatic five-membered ring having two or more heteroatoms selected from the group consisting of N, O, and S;
heteroaryl groups having 6 to 20 aromatic ring atoms which comprise at least one heteroaromatic six-membered ring having one or more heteroatoms selected from the group consisting of N, O, and S; and
carbazole groups.

3. The electronic device of claim 1 , wherein at least one group R 1 or R 2 in the compound of formula (I) is selected from groups of formulae (Het-a) to (Het-e):

wherein
Ar 1 is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R 3 ;
V is on each occurrence, identically or differently, N or CR 3 ;
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.

4. The electronic device of claim 1 , wherein n is 1.

5. The electronic device of claim 1 , wherein all Z are CR 2 .

6. The electronic device of claim 1 , wherein E is on each occurrence, identically or differently, a single bond, C═O, N(R 1 ), O, S, S═O, or S(═O) 2 , wherein both groups E cannot be a single bond.

7. The electronic device of claim 1 , wherein said electronic device is selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices.

8. The electronic device of claim 1 , wherein said electronic device comprises the compound of formula (I) in an electron-transport layer or comprises the compound of formula (I) in an emitting layer as matrix material in combination with one or more dopants.

9. A compound of formula (I-1):

wherein
E 2 is on each occurrence, identically or differently, a single bond, C═O, N(R 1 ), O, or S, wherein both groups E 2 cannot be a single bond;
T is on each occurrence, identically or differently, CR 1 or N;
Y is N(R 1 ), O, or S;
Z is on each occurrence, identically or differently, CR 2 or N;
R 1 is on each occurrence, identically or differently, H, D, F, C(═O)R 3 , CN, Si(R 3 ) 3 , N(R 3 ) 2 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , 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 R 3 , wherein one or more CH 2 groups in said groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , and wherein o

Assignees

• Merck Patent Gmbh

Inventors

• Pan Junyou
• Parham Amir Hossain
• Scheurich Rene Peter
• Rudolph Thomas

Classifications

• H01L51/5024

  Electricity · mapped topic

• C07D491/052

  the oxygen-containing ring being six-membered · CPC title

• H01L51/0072

  Electricity · mapped topic

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title