Formulations and electronic devices

Patent metadata

Field	Value
Publication number	US-10615343-B2
Application number	US-201515508366-A
Country	US
Kind code	B2
Filing date	Aug 4, 2015
Priority date	Sep 5, 2014
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

The present invention relates to a formulation comprising at least one organofunctional material which can be employed for the production of functional layers of electronic devices, and at least one aromatic compound. The present invention furthermore relates to electronic devices which are obtainable from these formulations.

First claim

The invention claimed is:

1. A formulation comprising at least one organofunctional material which can be employed for the production of functional layers of electronic devices, and at least one aromatic compound having a structure of the formula (1) or (2)

where the following applies to the symbols used:
X is on each occurrence, identically or differently, CR or N, where in total at most 2 radicals X stand for N;
R is on each occurrence, identically or differently, H, D, F, N(R 1 ) 2 , CN, NO 2 , C(═O)N(R 1 ) 2 , Si(R 1 ) 3 , C(═O)R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C Si(R 1 ) 2 , C═O, NR 1 , O, S or CONR 1 and where one or more H atoms is optionally replaced by D, F, NO 2 or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ; two adjacent radicals R here may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
R 1 is on each occurrence, identically or differently, H, D, F, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , C(═O)R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two or more adjacent radicals R 1 with one another or R 1 with R here may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
R 2 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 2 here may also form a mono- or polycyclic, aliphatic ring system with one another;
Y is on each occurrence, identically or differently, a group CR,
wherein
the adjacent groups Y in the structure of the formula (1) or (2) together form a ring of one of the following formulae (3), (4), (5), (6), (7), (8) and (9):

where R 1 has the meaning given above, the dashed lines represent the bonds from the two carbon atoms of group Y to the radicals X of the aromatic or heteroaromatic ring in the structure of the formula (1) or formula (2), and furthermore:
A 1 , A 3 are, identically or differently on each occurrence, C(R 3 ) 2 , O, S, NR 3 or C(═O);
A 2 is C(R 1 ) 2 , O, S, NR 3 or C(═O);
G is an alkylene group having 1, 2 or 3 C atoms, which is optionally substituted by one or more radicals R 2 , or is —CR 2 ═CR 2 — or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
R 3 is, identically or differently on each occurrence, F, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two radicals R 3 which are bonded to the same carbon atom may form an aliphatic or aromatic ring system with one another here and thus form a spiro system; furthermore, R 3 may form an aliphatic ring system with an adjacent radical R or R 1 ;
with the proviso that two identical heteroatoms in the above-mentioned groups are not bonded directly to one another and two groups C═O are not bonded directly to one another and
the aromatic compound having a structure of the formula (1) or (2) is a solvent having a viscosity of at least 3 mPas and a surface tension of at most 40 mN/m wherein the organofunctional material which can be employed for the production of functional layers of electronic devices is selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron-transport materials, exciton-blocking materials, electron-injection materials, hole-conductor materials, hole-injection materials, n-dopants, p-dopants, wide-band-gap materials, electron-blocking materials and hole-blocking materials.

2. The formulation according to claim 1 , wherein the proportion of the aromatic compound having a structure of the formula (1) or (2) in the formulation is at least 0.1% by weight based on the formulation.

3. The formulation according to claim 1 , wherein the proportion of the aromatic compound having a structure of the formula (1) or (2) in the formulation is at least 20% by weight based on the formulation.

4. The formulation according to claim 1 , wherein the aromatic compound having a structure of the formula (1) or (2) has a boiling point of at most 300° C.

5. The formulation according to claim 1 , wherein
the aromatic compound having a structure of the formula (1) or (2) has a viscosity of at least 5 mPas,
the proportion of the aromatic compound having a structure of the formula (1) or (2) in the formulation is at least 80% by weight, based on the formulation
the aromatic compound having a structure of the formula (1) or (2) has a surface tension of at most 30 mN/m, and
the aromatic compound having a structure of the formula (1) or (2) has a boiling point of at most 280° C.

6. The formulation according to claim 1 , wherein, in the ring structures of one of the formulae (3), (4), (5), (6), (7), (8) or (9), at least one

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Martynova Irina
• Ludemann Aurélie
• Kluge Edgar
• Koenen Nils

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/185

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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title