Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9780311-B2
Application number	US-201214235511-A
Country	US
Kind code	B2
Filing date	Jul 3, 2012
Priority date	Jul 29, 2011
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention relates to compounds for use in electronic devices, preferably organic electroluminescent devices. The invention furthermore relates to processes for the preparation of these compounds and to electronic devices comprising these compounds, preferably in a function as matrix materials and/or as electron-transport materials.

First claim

The invention claimed is:

1. A compound of formula (or formula (II)

wherein
R* is, identically or differently on each occurrence, —CN, or
a group selected from a keto group the formula (K)

a Phosphorus oxide group of the formula (P)

a sulfur oxide group of the formula (S)

 wherein a is 1 or 2, or
a group of the formulae (H-1) to (H-10)

wherein the dashed bond marks the bonding, position, and
W is, identically or differently on each occurrence, CR 2 or N, with the proviso that at least one group W per formula is N, and
U is NR 2 , O, or S;

X, Y are, identically or differently on each occurrence, a single bond, C(R 1 ) 2 , NR 1 , O, or S, wherein at least one of the two groups X and Y of a ring is NR 1 , O, or S;
V is a single bond, CO, CS, P(O)R 1 , SO, or SO 2 , with the proviso that V may only be a single bond if at least one of the groups Z in the rings bonded to V is N;
T is, identically or differently on each occurrence, a single bond, C(R 1 ) 2 , CO, CS, Si(R 1 ) 2 , NR 1 , P(O)R 1 , O, S, SO, or SO 2 ;
Z is, identically or differently on each occurrence, CR 1 or N if no group is bonded to Z, and C if a group is bonded to Z;
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein each is optionally substituted by one or more radicals R 2 , and wherein one or more CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), O—, —S—, SO, or SO 2 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, NO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , wherein two or more radicals R 1 optionally define a ring system;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein each is optionally substituted by one or more radicals R 3 , and wherein one or more CH 2 groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═S, 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 are optionally replaced by D, F, Cl, Br, I, CN, NO 2 , 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 , wherein two or more radicals R 2 optionally define a ring system;
R 3 is, identically or differently on each occurrence, 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 car F, and wherein two or more substituents R 3 optionally define a ring system;
m is, identically or differently on each occurrence, 0 or 1, where at least one m in formula (I) or formula (II) is 1;
n is, identically or differently on each occurrence, 0 or 1, where at least one n in formula (I) is 1, and wherein the groups X and Y are each bonded in adjacent positions to the six-membered ring of the spirobifluorene derivative.

2. The compound of claim 1 , wherein said compound contains no condensed aryl groups having more than 16 aromatic ring atoms.

3. The compound of claim 1 , wherein X or Y is independently, C(R 1 ) 2 or NR 1 , and R 1 is on each occurrence, identical or different, selected from H, D, F, CN, Si(R 2 ) 3 , or a straight-chain alkyl or alkoxyl group having 1 to 20 C or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms.

4. The compound of claim 1 , wherein the group R* is bonded to the modified spirobifluorene skeleton in position 2′ or in position 7′.

5. The compound of claim 1 , wherein one of the two groups X and Y is a single bond and the other of the two groups X and Y is a group NR 1 .

6. The compound of claim 1 , wherein the group T is, identically or differently on each occurrence, a single bond, C(R 1 ) 2 , O, or S.

7. The compound of claim 1 , wherein one of the two indices m in formula (I) or formula (II) is 1 and the other is zero.

8. The compound of claim 1 , wherein one of the two indices n in formula (I) is 1 and the other is zero.

9. An oligomer, polymer, or dendrimer, comprising one or more compounds of claim 1 , wherein the bond(s) to the polymer, oligomer, or dendrimer, may be localised at any desired positions in formula (I) or (II) that are substituted by R 1 , or R 2 .

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

11. A formulation comprising at least one oligomer, polymer, or dendrimer of claim 9 and at least one solvent.

12. A process for the preparation of the compound of claim 1 , wherein
a heteroaryl group is condensed onto a spirobifluorene group which is substituted by an electron-deficient group, or wherein
a cyclisation reaction is carried out via which a modified spirobifluorene group is obtained.

13. An electronic device comprising at least one compound of claim 1 .

14. The electronic device of claim 13 , wherein the 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, light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices.

15. The electronic device of claim 13 , wherein the electronic device is an organic electroluminescent device, and wherein the compound is
matrix material in an emitting layer,
electron-transport material in an electron-transport or electron-injection layer, or
hole-blocking material in a hole-blocking layer.

16. An electronic device comprising at least one oligomer, polymer, or dendrimer, of claim 9 .

17. The electronic device of claim 16 , wherein the electronic device is selected from the group consisting

Assignees

• Parham Amir Hossain
• Pflumm Christof
• Jatsch Anja
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Pflumm Christof
• Jatsch Anja

Classifications

• C07D471/20

  Spiro-condensed systems · CPC title

• C07D221/20

  Spiro-condensed ring systems · CPC title

• C07D487/10

  Spiro-condensed systems · CPC title

• C07D265/34

  condensed with carbocyclic rings · CPC title

• C07D403/04 Primary

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