Formulations for the production of electronic devices

Patent metadata

Field	Value
Publication number	US-9666806-B2
Application number	US-201013395542-A
Country	US
Kind code	B2
Filing date	Sep 15, 2010
Priority date	Sep 16, 2009
Publication date	May 30, 2017
Grant date	May 30, 2017

Abstract

The present invention relates to formula, comprising at least one solvent, and at least one functional composition of the general formula (I), wherein A is a functional structural element, B is a solvent-providing structural element, and k is an integer in the range of 1 to 20. The molecular weight of the functional composition is at least 550 g/mol, and the solvent-providing structural element B corresponds to the general formula ((L-I). Ar1, Ar2 JeWeUs, independently of each other, signify an aryl or heteroaryl group, which can be substituted with one or several discretionary residues R. Each X is, independently of one another, N or CR2, preferably CH. R1, R2, independently of one another, is hydrogen, a linear alkyl, alkoxy, or thioalkoxy group with 1 to 40 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group with 3 to 40 C atoms, or a silyl group, or a substituted keto group with 1 to 40 C atoms, an alkoxycarbonyl group with 2 to 40 C atoms, an aryloxycarbonyl group with 7 to 40 C atoms, a cyano group (—CN), a carbamoyl group (—C(═O)NH2), a haloformyl group (—C(═O)—X, wherein X signifies a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or a thioisocyanate group, a hydroxy group, a nitro group, a CF3 group, C1, Br, F, a cross-linkable group, or a substituted or non-substituted aromatic or heteroaromatic ring system with 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group with 5 to 60 ring atoms, or a combination of these systems, wherein one or several of groups R1 and/or R2 can form a monocyclic or polycyclic, aliphatic or aromatic ring system with one another and/or with the ring to which group R1 is bound, and I is 0, 1, 2, 3 or 4, wherein the dashed linkage indicates the linkage to the functional structure element A. The present invention further relates to preferred compositions of the formula (I) and electronic devices containing said compositions.

First claim

The invention claimed is:

1. A formulation comprising at least one solvent and at least one functional compound of the general formula (I)
A B] k   (I)

where

A is a functional structural element, which has
(a) hole-injection and/or hole-transport properties,
(b) light-emitting properties
B is a solubility-promoting structural element and
k is an integer in the range from 1 to 20,
wherein
the solubility-promoting structural element B conforms to the general formula (L-I)

where
Ar 1 and Ar 2 are each, independently of one another, an aryl or heteroaryl group, which may be substituted by one or more radicals R,
X is in each case, independently of one another, N or CR 2 ,
R 1 and R 2 are each, independently of one another, hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a cyano group (—CN), a carbamoyl group (—C(═O)NH 2 ), a haloformyl group (—C(═O)—X′, in which X′ represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or a thioisocyanate group, a hydroxyl group, a nitro group, a CF 3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where one or more of the groups R 1 and/or R 2 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another and/or with the ring to which the group R 1 is bonded; and
I is 0, 1, 2, 3 or 4;
where the dashed bond indicates the bond to the functional structural element A and the molecular weight of the functional compound of the general formula (I) is at least 800 g/mol,
wherein the functional structural elements A having hole-injection and/or hole-transport properties are selected from the group consisting of triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, phenoxathiyne, carbazole, azulene, thiophene, pyrrole and furan derivatives and further O-, S- or N-containing heterocycles having a high HOMO (HOMO=highest occupied molecular orbital) and
wherein the functional structural element A having light-emitting properties is a unit which contains at least one heavy atom having an atomic number of greater than 36.

2. The formulation according to claim 1 , wherein X is CH.

3. The formulation according to claim 1 , wherein the solubility-promoting structural element B conforms to the general formula (L-II)

where
R 1 , R 2 , R 3 , R 4 are each, independently of one another, a straight-chain alkyl, alkenyl or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a formyl group (—C(═O)—H), a CF 3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where one or more of the groups R 1 , R 2 , R 3 and/or R 4 optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another and/or with another ring;
m is 0, 1, 2 or 3,
n, o are each, independently of one another, 0, 1, 2, 3, 4 or 5
and the dashed bond and the index 1 have the meaning mentioned in claim 1 .

4. The formulation according to claim 1 , wherein the formulation comprises at least 80% by weight of aromatic or heteroaromatic solvent.

5. The formulation according to claim 1 , wherein the index k in formula (I) is an integer greater than or equal to 2.

6. The formulation according to claim 1 , wherein the molecular weight of the functional compound of the general formula (I) is at least 900 g/mol.

7. The formulation according to claim 1 , wherein the functional compound of the general formula (I) has a glass-transition temperature of at least 70° C.

8. The formulation according to claim 1 , wherein the functional structural element A in formula (I) is a unit which has hole-injection and/or hole-transport properties.

9. The formulation according to claim 1 , wherein the functional structural element A in formula (I) is a unit which has light-emitting properties.

10. The formulation according to claim 9 , wherein the functional structural element A in formula (I) is a unit having phosphorescent properties.

11. The formulation according to claim 1 , wherein the functional structural element A in formula (I) is a unit which improves the transfer from the singlet state to the triplet state of light-emitting compounds.

12. The formulation according to claim 1 , wherein the weight ratio of structural element A to structural element B in formula (I) is in the range from 2:1 to 1:20.

13. A functional compound of the general formula (I)
A B] k   (I)

wherein
A is a functional structural element, which has
(a) hole-injection and/or hole-transport properties,
(b) light-emitting properties
B is a solubility-promoting structural element and
k is an integer in the range from 1 to 20,
wherein
the molecular weight of the functional compound is at least 800 g/mol and
the solubility-promoting structural element B conforms to the formula (L-I)

where
Ar 1 and Ar 2 are each, independently of one another, an aryl or heteroaryl group, which may be substituted by one or more radicals R of any desired type,
X is in each case, independently of one another, N or CR 2 ,
R 1 and R 2 are each, independently of one another, hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a cyano group (—CN), a carbamoyl group (—C(═O)NH 2 ), a haloformyl group (—C(═O)—X′, in which X′ represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or a thioisocyanate group, a hydroxyl group, a nitro group, a CF 3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where one or more of the groups R 1 and/or R 2 optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another and/or with the ring to which the group R 1 is bonded; and
I is 0, 1, 2, 3 or 4;
where the dashed bond indicates the bond to the functional structural element A;
with the exception of compounds of the general fo

Assignees

• Anémian Rémi Manouk
• Heun Susanne
• Eberle Thomas
• Stoessel Philipp
• Merck Patent Gmbh

Inventors

• Anémian Rémi Manouk
• Heun Susanne
• Eberle Thomas
• Stoessel Philipp

Classifications

• H10K85/60

  Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence) · CPC title

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• H01L51/0085

  Electricity · mapped topic

• H01L51/5048

  Electricity · mapped topic

• H01L51/0508

  Electricity · mapped topic