Triarylamine-substituted benzo[H]quinoline-derivatives as materials for electronic devices

Patent metadata

Field	Value
Publication number	US-10407394-B2
Application number	US-201415026650-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Oct 4, 2013
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

The invention relates to a heteroaryl compound according to formula (I) and to the use thereof in electronic devices.

First claim

The invention claimed is:

1. A compound of formulae (I-1), (I-2) or (I-3)

where:
A is a group (A-1)

which are bonded via the bond marked *,
Ar 1 is the same or different at each instance and is selected from benzene, pyridine, pyrimidine, triazine, naphthalene, quinoline, fluorene, spirobifluorene, indenofluorene, carbazole, indenocarbazole, indolocarbazole, dibenzofuran and dibenzothiophene, each of which may be substituted by one or more R 1 radicals;
Ar 2 is the same or different at each instance and is selected from benzene, biphenyl, terphenyl, quaterphenyl, pyridine, pyrimidine, pyrazine, pyridazine, triazine, naphthalene, quinoline, fluorene, spirobifluorene, indenofluorene, carbazole, indenocarbazole, indolocarbazole, dibenzofuran or dibenzothiophene, each of which may be substituted by one or more R 1 radicals;
X is the same or different at each instance and is a single bond or a group selected from BR 2 , C(R 2 ) 2 , —C(R 2 ) 2 —C(R 2 ) 2 —, —C(R 2 )═C(R 2 )—, —C(R 2 ) 2 —O—, —C(R 2 ) 2 —NR 2 —, Si(R 2 ) 2 , C═O, NR 2 , PR 2 , P(═O)R 2 , O, S, S═O and SO 2 ;
R 1 , R 2 are the same or different at each instance and are H, D, F, C(═O)R 3 , CN, Si(R 3 ) 3 , N(R 3 ) 2 , P(═O)(R 3 ) 2 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms, where the abovementioned groups may each be substituted by one or more R 3 radicals and where one or more CH 2 groups in the abovementioned groups may be 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 , or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R 3 radicals; two or more R 2 radicals may be joined to one another and form a ring;
R 3 is the same or different at each instance and is H, D, F, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms, where the abovementioned groups may each be substituted by one or more R 4 radicals and where one or more CH 2 groups in the abovementioned groups may be 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 , or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R 4 radicals; two or more R 3 radicals may be joined to one another and form a ring;
R 4 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D, F or CN; two or more R 4 substituents may be joined to one another and form a ring;
n is 0, 1, 2 or 3;
i is the same or different at each instance and is 0 or 1; and
wherein the compound of formulae (I-1), (I-2) or (I-3) does not have any fused aryl or heteroaryl group having more than 10 aromatic ring atoms, as substituent R 1 , R 2 , R 3 and R 4 .

2. A compound of claim 1 , wherein n is 0.

3. A compound of claim 1 , wherein X is the same or different at each instance and is selected from a single bond and a group selected from C(R 2 ) 2 , C═O, NR 2 , O or S.

4. A compound of claim 1 , wherein the compound does not have any further arylamino group, any further bridged arylamino group or any further carbazole group in addition to the A group.

5. A process for preparing a compound of claim 1 , comprising converting a compound of formulae (I-1), (I-2) or (I-3)

in a coupling reaction,
where the variable groups and indices are as defined in claim 1 ,
and where Y is any reactive group.

6. An oligomer, polymer or dendrimer comprising one or more compounds of claim 1 , wherein the bonds to the polymer, oligomer or dendrimer may be localized at any desired positions substituted by R 1 or R 2 in formulae (I-1), (I-2) or (I-3).

7. A formulation comprising at least one compound of claim 1 , and at least one solvent.

8. An electronic device comprising anode, cathode and at least one organic layer, wherein the organic layer comprises at least one compound of claim 1 .

9. The electronic device of claim 8 , that 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.

10. The electronic device of claim 8 , wherein the organic layer is an emitting layer, and the at least one compound of formulae (I-1), (I-2) or (I-3) is present as matrix material, and the electronic device is an organic electroluminescent device.

11. The electronic device of claim 8 , wherein the organic layer is a hole transporting layer, and the at least one compound of formulae (I-1), (I-2) or (I-3) is present as a hole transport material, and the electronic device is an organic electroluminescent device.

12. The compound of claim 1 , wherein the compound is a compound of formula (I-1).

13. The compound of claim 1 , wherein
R 1 is the same or different at each instance and is H, D, F, CN, Si(R 3 ) 3 , N(R 3 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, optionally substituted by one or more R 3 radicals and where one or more CH 2 groups optionally replaced by —C≡C—, —R 3 C═CR 3 —, Si(R 3 ) 2 , C═O, C═NR 3 , —NR 3 —, —O—, —S—, —C(═O)O— or —C(═O)NR 3 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals,
R 2 is the same or different at each instance and is H, D, F, Si(R 3 ) 3 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, optionally substituted by one or more R 3 radicals and where one or more CH 2 groups optionally replaced by —C≡C—, —R 3 C═CR 3 —, Si(R 3 ) 2 , C═O, C═NR 3 , —NR 3 —, —O—, —S—, —C(═O)O— or —C(═O)NR 3 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals,
R 3 is the same or different at each instance and is H, D, F, CN, Si(R 4 ) 3 , N(R 4 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, optionally substituted by one or more R 4 radicals and where one or more CH 2 groups is optionally replaced by —C≡C—, —R 4 C═CR 4 —, Si(R 4 ) 2 , C═O, C═NR 4 , —NR 4 —, —O—, —S—, —C(═O)O— or —C(═O)NR 4 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, each of which may be substituted by one or more R

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Stoessel Philipp
• Eberle Thomas
• Jatsch Anja
• Kroeber Jonas Valentin
• Pflumm Christof
• Martynova Irina
• Voges Frank
• Stieber Frank

Classifications

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title