Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11629126-B2
Application number	US-201716336720-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Oct 6, 2016
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

The present invention relates to compounds of formula (1). The compounds are suitable for use in electronic devices, in particular organic electroluminescent devices, comprising these compounds. In some embodiments, the compounds are used as matrix materials for phosphorescent or fluorescent emitters as well as a hole-blocking or electron-transport materials.

First claim

The invention claimed is:

1. A crosslinked compound obtained by crosslinking groups Q of a compound of the formula (2) or (3),

where
Ar 3 , Ar 4 , Ar 5 are selected on each occurrence, identically or differently, from the group consisting of an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;
Q is on each occurrence, identically or differently, a crosslinkable group bonded to the adjacent phenyl group via a single bond, or Q is a crosslinkable mono- or polycyclic group condensed on the adjacent phenyl group;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, (R)C═C(R)Ar, CN, NO 2 , Si(R 1 )3, B(OR 1 ) 2 , B(R 1 ) 2 , B(N(R 1 ) 2 ) 2 , OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 1 , where one or more, non-adjacent CH 2 groups may be replaced by (R 1 )C═C(R 1 ), C≡C, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, P(═O)(R 1 ), SO, SO 2 , N(R 1 ), O, S or CON(R 1 ) and where one or more H atoms may be replaced by D, F, Cl, Br, I, 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 1 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , where optionally two adjacent substituents R can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
Ar is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , (R 2 )C═C(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , B(R 2 ) 2 , B(N(R 2 ) 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more, non-adjacent CH 2 groups may be replaced by (R 2 )C═C(R 2 ), C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, P(═O)(R 2 ), SO, SO 2 , N(R 2 ), O, S or CON(R 2 ) and where one or more H atoms may be replaced by D, F, Cl, Br, I, 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 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , where optionally two adjacent substituents R 1 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, NO 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or a straightchain alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms; where optionally two adjacent substituents R 2 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
m is on each occurrence, identically or differently, 1 or 2;
n is on each occurrence, identically or differently, 0 or 1;
with the proviso that m+n=2 in the amino moiety comprising a group Ar 3 and an aromatic or heteroaromatic ring system containing Y, and m+n=2 in the amino moiety comprising a group Ar 5 and an aromatic or heteroaromatic ring system containing Y;
p is 1;
s is on each occurrence, identically or differently, 0, 1, 2, 3 or 4; and
t is on each occurrence, identically or differently, 0, 1, 2 or 3.

2. The compound according to claim 1 ,
with the proviso that s≤3 and t≤2 when the corresponding phenyl ring is substituted by a group Q which corresponds to a mono- or polycyclic group condensed on this phenyl ring.

3. The compound according to claim 1 , characterized in that Q is on each occurrence, identically or differently, a crosslinkable group selected from terminal or cyclic alkenyl groups, terminal dienyl groups, terminal alkynyl groups, alkenyloxy groups, dienyloxy groups, alkynyloxy groups, acrylic acid derivatives, oxetane groups, oxirane groups, silanes groups and cyclobutane groups.

4. The compound according to claim 1 , characterized in that Q is selected from groups of the following formulae Q1 to Q24,

where the dashed bond in the formulae Q1 to Q11, Q13 to Q24 and the dashed bonds in the formula Q12 represent the linking of the crosslinkable group to; the adjacent phenyl group of the formula (2) or (3);
and where
R 11 , R 12 and R 13 are on each occurrence, identically or differently, H, a straight-chain or branched alkyl group having 1 to 6 C atoms;
Ar 10 is on each occurrence, in each case identically or differently, a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, where R is as defined in claim 1 ;
u is an integer from 0 to 8; and
v is an integer from 1 to 8.

5. The compound according to claim 1 , where Ar 3 , Ar 4 and Ar 5 are selected on each occurrence, identically or differently, from the group consisting of an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R.

6. The compound according to claim 1 , where Ar 3 , Ar 4 and Ar 5 are selected on each occurrence, identically or differently, from the group consisting of benzene, naphthalene, anthracene, biphenyl, terphenyl, quaterphenyl, fluorene, dibenzofuran, dibenzothiophene, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, azacarbazole, benzocarboline, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, each of which may be substituted by one or more radicals R.

7. The compound according to claim 1 , where m is equal to 1 and n is equal to 1.

8. The compound according to claim 1 , where m is equal to 1.

9. A formulation comprising at least one compound according to claim 1 and at least one solvent.

10. An electronic device comprising at least one compound according to claim 1 selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, dye-sensitised organic solar cells, organic optical detectors,

Assignees

• Merck Patent Gmbh

Inventors

• Scheible Katja Maria
• Eckes Fabrice
• Heil Holger
• Burkhart Beate
• Joosten Dominik
• Montenegro Elvira

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C07C211/61 Primary

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

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title