Phenoxazine derivatives for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-2018240983-A1
Application number	US-201615752718-A
Country	US
Kind code	A1
Filing date	Jul 15, 2016
Priority date	Aug 14, 2015
Publication date	Aug 23, 2018
Grant date	—

Abstract

The present invention relates to the compounds of the formulae (1) and (2) and to organic electroluminescent devices, in particular blue-emitting devices, in which these compounds are used as host material or dopant in the emitting layer and/or as hole-transport material and/or as electron-transport material.

First claim

1 - 16 . (canceled)

17 . A compound of formula (1) or formula (2):

wherein
Ar is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
Ar 1 is, on each occurrence, identically or differently, a group of formulae (Ar1-1) through (Ar1-4):

wherein the dashed bond denotes the linking to Ar S or to the phenoxazine structure if Ar S is absent;
V is, on each occurrence, identically or differently, CR 2 or N or two adjacent groups V are a group of formula (V-1) or (V-2);

wherein the dashed bonds denote the linking of these units;

Ar 2 is, on each occurrence, identically or differently, an aryl group having 10 to 18 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
Ar S is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 2 ;
E 0 is selected from the group consisting of a single bond, C(R 1 ) 2 , Si(R 1 ) 2 , C═O, O, S, S═O, SO 2 , N(R 1 ), P(R 1 ), and P(═O)R 1 ;
E 1 , E 2 , and E 3
are, on each occurrence, identically or differently, selected from the group consisting of B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ), and P(═O)R 1 ;

or
E 1 , E 2 and/or E 3 is a group of formula (E-1):

wherein the dashed bonds denote the bonding to the 5-membered ring comprising E 1 , E 2 , or E3;
R, R 1 , R 2 , and R 3
are, on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are each optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , wherein two adjacent radicals R, two adjacent radicals R 1 , two adjacent radicals R 2 , and/or two adjacent radicals R 3 are optionally linked to one another and optionally define an aliphatic or aromatic ring;

R 4 is, on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are each optionally substituted by one or more radicals R 5 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 5 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 , where two adjacent radicals R 4 are optionally linked to one another and optionally define an aliphatic or aromatic ring;
R 5 is, on each occurrence, identically or differently, H or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein H atoms are optionally replaced by F; and wherein two adjacent radicals R 5 also optionally define a mono- or polycyclic aliphatic or aromatic ring system with one another;
a, b, c, and d
are, identically or differently, selected from 0 or 1; wherein a=0, b=0, c=0, or d=0 denotes that the corresponding bridge is not present;

wherein
a+b= 1 or 2; and
c+d= 1 or 2;

f is, identically or differently, on each occurrence 0, 1, 2, or 3;
g and h
are, identically or differently, on each occurrence 0, 1, or 2; wherein g+a+b≤3 and h+c+d≤3;

m is, identically or differently, on each occurrence 0, 1, 2, 3, or 4; and
i is, identically or differently, on each occurrence 0, 1, 2, or 3, wherein i=0 denotes that the group Ar S is absent and replaced by a single bond.

18 . The compound of claim 17 , wherein E 0 is a single bond and Ar 1 is, on each occurrence identically, a group of formulae (Ar1′-1) through (Ar1′-4):

wherein the dashed bond denotes the linking to Ar S or to the phenoxazine structure if Ar S is absent.

19 . The compound of claim 17 , wherein a+c=1 and b+d=0 or b+d=1 and a+c=0.

20 . The compound of claim 17 , wherein Ar is an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms.

21 . The compound of claim 17 , wherein Ar is selected from the group consisting of phenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, biphenyl, terphenyl, quaterphenyl, naphtyl, anthracyl, phenanthryl, chrysenyl, and pyrenyl, wherein each of which is optionally substituted by one or more radicals R 2 .

22 . The compound of claim 17 , wherein Ar 2 is selected from the group consisting of naphtyl, anthracyl, phenanthryl, chrysenyl, and pyrenyl, wherein each of which is optionally substituted by one or more radicals R 2 .

23 . The compound of claim 17 , wherein the compound is selected from group consisting of compounds of formulae (1-1-a), (2-1-a), and (2-2-a):

wherein Ar 2 is a group of formulae (Ar2-1) through (Ar2-3)

wherein
the dashed bond denotes the linking to the phenoxazine structure and
* indicates the linking position to the group E 2 ; and

wherein each free position on the naphtyl group in formulae (Ar2-1) through (Ar2-3) is optionally substituted by a radical R 2 ;
with the proviso that in formula (1-1-a), V is C when the linking to the phenoxazine structure or the phenyl phenoxazine structure takes place via V.

24 . The compound of claim 17 , wherein the compound is selected from group consisting of compounds of formulae (1-1-b) through (2-2-d):

wherein each free position of the two phenyl rings condensed on the

Assignees

• Merck Patent Gmbh

Inventors

• Heil Holger
• Burkhart Beate
• Rodriguez Lara-Isabel
• Meyer Sebastian
• Linge Rouven

Classifications

• H01L51/5012

  Electricity · mapped topic

• H01L51/0071 Primary

  Electricity · mapped topic

• H01L51/0055

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic

• H01L51/0056

  Electricity · mapped topic