Bisbenzofuran-fused indeno[1,2-B]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)

Patent metadata

Field	Value
Publication number	US-11453680-B2
Application number	US-201716463507-A
Country	US
Kind code	B2
Filing date	Nov 22, 2017
Priority date	Nov 25, 2016
Publication date	Sep 27, 2022
Grant date	Sep 27, 2022

Abstract

The present invention relates to Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLEDs).

First claim

The invention claimed is:

1. A compound of formula (1-1a)-(1-6a):

wherein
Z is on each occurrence, identically or differently, CR or N;
E is on each occurrence, identically or differently, selected from the group consisting of —BR 0 —, —C(R 0 ) 2 —, —C(R 0 ) 2 —C(R 0 ) 2 —, —C(R 0 ) 2 —O—, —C(R 0 ) 2 —S—, —R 0 C═CR 0 —, —R 0 C═N—, —Si(R 0 ) 2 —, —Si(R 0 ) 2 —Si(R 0 ) 2 —, Ge(R 0 ) 2 , —C(═O)—, —C(═NR 0 )—, —C(═C(R 0 ) 2 )—, —O—, —S—, —Se—, —S(═O)—, —SO 2 —, —N(R 0 )—, —P(R 0 )— and —P((═O)R 0 )—,
X is on each occurrence, identically or differently, selected from the group consisting of —O—, —S—, —S(═O)—, —SO 2 —, —N(R 0 )—, —BR 0 —, Si(R 0 ) 2 , —P(R 0 )—, and —P((═O)R 0 )—;
W is on each occurrence, identically or differently, CR or N;
R and R 0 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 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, each of which is optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 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 , O, S, or CONR 2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , and wherein two adjacent substituents R and/or two adjacent substituents R 0 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R 2 ;
R 1 is on each occurrence, identically or differently, D, F CN, C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, —Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 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, each of which is optionally substituted by one or more radicals R 2 ,
wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , 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 , O, S, or CONR 2 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , and wherein two adjacent substituents R 1 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R 2 ;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , 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, each of which is optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 3 C═CR 3 , Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S, or CONR 3 and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , and wherein two adjacent substituents R 2 optionally define a mono- or polycyclic, aliphatic ring system or aromatic ring system, which is optionally substituted by one or more radicals R 3 ;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, wherein one or more non-adjacent CH 2 groups are optionally replaced by SO, SO 2 , O, S and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms; and
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 .

2. The compound of claim 1 , wherein X is O or S.

3. The compound of claim 1 , wherein E is —C(R 0 ) 2 — or —Si(R 0 ) 2 —.

4. The compound of claim 1 , wherein the compound is selected from the group consisting of compounds of formulae (1-1b) through (1-6c):

5. The compound of claim 1 , wherein when R 1 is an aromatic or heteroaromatic ring system, then R 1 is selected on each occurrence, identically or differently, from the group consisting of formula (R 1 -1):

wherein the dashes denotes the bond to the structure of formula (1);
Ar 3 and Ar 4 are selected on each occurrence, identically or differently, from the group consisting of benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, fluorene, benzofluorene, spirobifluorene, cis-indenofluorene, trans-indenofluorene, cis-benzindenofluorene, trans-benzindenofluorene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, indole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, pyrazole, indazole, imidazole, benzimidazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, pyrazine, quinoxaline, 1,3,5-triazine, 1,2,4-triazine, and 1,2,3-triazine, which are optionally substituted by one or more radicals R 2 ; and
n is an integer from 0 to 20.

6. The compound of claim 5 , wherein Ar 3 and Ar 4 are on each occurrence, identically or differently, selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, fluorene, benzofluorene, spirobifluorene, cis-indenofluorene, trans-indenofluorene, cis-benzindenofluorene, trans-benzindenofluorene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, indole, carbazole, indolocarbazole, and indenocarbazole, which in each case is optionally substituted by one or more radicals R 2 .

7. The compound of claim 1 , wherein R 0 is on each occurrence, identically or differently, H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R 2 , wherein one or more H atoms are optionally replaced by F, or an aryl or heteroaryl group having 5 to 25 aromatic ring atoms, which is optionally substituted by one or more radicals

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C07D493/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title