Heterocyclic bridged biphenyls

Patent metadata

Field	Value
Publication number	US-10934262-B2
Application number	US-201815910568-A
Country	US
Kind code	B2
Filing date	Mar 2, 2018
Priority date	Sep 14, 2006
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

The present invention relates electroluminescent devices, comprising a compound of the formula

especially as host for phosphorescent compounds. The hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.

First claim

The invention claimed is:

1. An electroluminescent (EL) device, comprising a compound of the formula

wherein A is a 6-membered heteroaromatic ring, containing at least one heteroatom selected from nitrogen, oxygen, and sulfur,
Z 1 is

—NA 1 A 1 , —P(═O)A 4 A 4′ , or —SiA 6 A 7 A 8
Z 2

NA 2 A 2′ , —P(═O)A 5 A 6′ , or —SiA 6′ A 7′ A 8′ ,
Ar and Ar′ are independently of each other C 6 -C 14 aryl, which may optionally be substituted by one or more groups selected from C 1 -C 25 alkyl which may be optionally interrupted by —O—, or C 1 -C 25 alkoxy,
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently of each other hydrogen, halogen, or an organic substituent, or
R 1 and R 2 , R 4 and R 6 , R 2 and R 3 , R 5 and R 3 , and/or R 5 and R 6 , which are adjacent to each other, together form an aromatic or heteroaromatic ring or a ring system which can optionally be substituted,
R 7 is an organic substituent, wherein two or more substituents R 7 in the same molecule may have different meanings, or can form together an aromatic or heteroaromatic ring or ring system, and
x is 0, or an integer of 1 to 5;
A 1 , A 2 , A 1′ , and A 2′ are independently of each other a C 6 -C 24 aryl group, a C 2 -C 30 heteroaryl group, which can optionally be substituted, or a group

wherein BU is a bridging unit, A 3 and A 3′ are independently or each other a C 6 -C 24 aryl group or a C 2 -C 30 heteroaryl group, which can optionally be subsituted, or A 1 and A 1′ or A 2 and A 2′ or A 3 and A 3′ together with the nitrogen atom to which they are bonded form a heteroaromatic ring or ring system,
A 4 , A 4′ , A 6 , A 7 , A 8 , A 5 , A 5′ , A 6′ , A 7′ , and A 8′ are independently of each other a C 6 -C 24 aryl group or a C 2 -C 30 heteroaryl group, which can optionally be substituted.

2. The EL device according to claim 1 , comprising a compound of formula

wherein R 1 and R 4 are independently of each other hydrogen, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, CN, or —CO—R 28 ,
R 2 , R 3 , R 5 , and R 6 are independently of each other hydrogen, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, CN, or —CO—R 28 ,
R 8 and R 9 are independently of each other hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, CN, or —CO—R 28 , or
R 8 and R 9 together form a group

wherein R 206′ , R 208′ , R 205 , R 206 , R 207 , R 208 , R 209 , and R 210 are independently of each other hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, CN, or —CO—R 28 ,
R 10 is hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, CN, or —CO—R 28 ,
R 8′ and R 9′ are independently of each other hydrogen, CN, CONR 25 R 26 , C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or —CO—R 28 ,
or two substituents R 1 and R 2 , R 4 and R 6 , R 2 and R 3 , and/or R 5 and R 6 , which are adjacent to each other, together form a group

or two substituents R 5 and R 3 , which are adjacent to each other, together form a group

wherein X 3 is O, S, C(R 119 )(R 120 ), or NR 17 , R 105 , R 106 , R 107 , R 108 , R 106 ′ and R 108 ′ are independently hydrogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, R 119 and R 120 are independently of each C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or
R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein
R 121 and R 122 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 119 and R 120 together form a five or six membered ring, which optionally can be substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 14 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or —C(═O)—R 2 , and
R 127 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
D is —CO—; —COO—; —S—; —SO—; —SO 2 —; —O—; —NR 25 —; —SiR 30 R 31 —; —POR 32 —; —CR 23 ═CR 24 —; or —C≡C—; and
E is —OR 29 ; —SR 29 ; —NR 25 R 26 ; —COR 28 ; —COOR 27 ; —CONR 25 R 26 ; —CN; or halogen;
G is E, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted by D, C 1 -C 18 perfluoroalkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy w

Assignees

• Udc Ireland Ltd

Inventors

• Wendeborn Frederique
• Schmidhalter Beat
• SCHäFER THOMAS
• Murer Peter
• Bardon Kristina

Classifications

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/649

  Aromatic compounds comprising a hetero atom · CPC title