Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9343683-B2
Application number	US-201113637402-A
Country	US
Kind code	B2
Filing date	Feb 28, 2011
Priority date	Mar 26, 2010
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The present invention relates to compounds having a spirobifluorene skeleton of the formula (I) for use as functional materials in electronic devices, in particular for use in the charge-transport layer and/or emission layer of organic electroluminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to mixtures comprising the compounds according to the invention. The invention furthermore relates to the use of the compounds of the formula (I) in electronic devices and to electronic devices comprising the compounds of the formula (I).

First claim

The invention claimed is:

1. An electroluminescent device comprising a hole-transport material, matrix material, or emitter material, the material including at least one compound of formula (I),

wherein:
X is, identically or differently on each occurrence, CH or CR 1 , with the provisos that at least two groups X per aromatic 6-membered ring is CR 1 , and X is C when Y is bonded to X;
Y is, identically or differently on each occurrence, a single bond, O, S, C(R 3 ) 2 , or NR 3 ;
R is, identically or differently on each occurrence, H, D, CHO, C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, COOR 3 , CON(R 3 ) 2 , a straight-chain alkyl group having 1 to 4 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, wherein one or more methylene groups in the alkyl, alkenyl and alkynyl groups are optionally replaced by Si(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , —O—, —S—, —COO— or —CONR 3 — and the above-mentioned alkyl, alkenyl and alkynyl groups are optionally substituted by one or more groups R 3 , or an aromatic ring system having 6 to 60 aromatic ring atoms or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, wherein two radicals R optionally define an aliphatic or aromatic ring system;
R 1 is, identically or differently on each occurrence, a straight-chain alkyl group having 1 to 8 C atoms or a branched or cyclic alkyl group having 3 to 8 C;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(Ar) 2 , N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, COOR 3 , CON(R 3 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent methylene groups are optionally replaced by Si(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , —O—, —S—, —COO— or —CONR 3 — and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, wherein two or more radicals R 2 optionally define an aliphatic or aromatic ring system;
R 3 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , OH, COOR 4 , CON(R 4 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 4 , wherein one or more non-adjacent methylene groups are optionally replaced by Si(R 4 ) 2 , C═S, C═Se, C—NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , —O—, —S—, —COO— or —CONR 4 — and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 4 , or a combination of these systems, wherein two or more radicals R 3 optionally define an aliphatic or aromatic ring system;
R 4 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic, and/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 identical or different substituents R 4 optionally define an aliphatic or aromatic ring system;
Ar is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 60 aromatic C atoms, and optionally substituted by one or more radicals R 3 ;
n is, identically or differently on each occurrence, 0 or 1, wherein when n=0 the group Y in question is not present.

2. The electroluminescent device of claim 1 , wherein 2 to 4× per aromatic six-membered ring is CR 1 .

3. The electroluminescent device of claim 1 , wherein said compound is a compound of formula (II)

wherein A 1 and A 2 are selected, identically or differently on each occurrence, from the group consisting of formulae (1-35) to (1-55):

wherein the dashed line represents the bond from the group to the spirobifluorene unit of the compound of formula (II).

4. The electroluminescent device of claim 3 , wherein A 1 and A 2 are identical.

5. The electroluminescent device of claim 1 , wherein R is, identically or differently on each occurrence, selected from the group consisting of H, D, an aromatic ring system having 6 to 14 aromatic ring atoms, and a heteroaromatic ring system having 5 to 14 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R 3 .

6. The electroluminescent device of claim 1 , wherein R 1 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl or 2-ethylhexyl.

7. The electroluminescent device of claim 1 , wherein the hole-transport material, the matrix material, or the emitter material is prepared with a formulation including the at least one compound of formula I and at least one solvent.

8. The electroluminescent device of claim 1 , wherein said compound is present in the hole-transport material as a hole-transport layer or a hole-injection layer and/or as a matrix material in the emitting layer.

9. The electroluminescent device of claim 4 , wherein R 2 is H.

10. The electroluminescent device of claim 4 , wherein the groups A 1 and A 2 are selected from formulae (1-36), (1-39), (1-41), (1-42), (1-43), (1-44), (1-45), (1-48), (1-51), (1-53) or (1-54).

11. The electroluminescent device of claim 5 , wherein R 1 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl or 2-ethylhexyl.

Assignees

• Becker Heinrich
• Schwaiger Jochen
• Spreitzer Hubert
• Voges Frank
• Heil Holger
• Merck Patent Gmbh

Inventors

• Becker Heinrich
• Schwaiger Jochen
• Spreitzer Hubert
• Voges Frank
• Heil Holger

Classifications

• C07C2603/94

  containing "free" spiro atoms · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• H01L51/006 Primary

  Electricity · mapped topic