Heterocyclic bridged biphenyls

Patent metadata

Field	Value
Publication number	US-2018258053-A1
Application number	US-201815910568-A
Country	US
Kind code	A1
Filing date	Mar 2, 2018
Priority date	Sep 14, 2006
Publication date	Sep 13, 2018
Grant date	—

Abstract

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

1 .- 10 . (canceled)

11 . 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 is

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 substituted, 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.

12 . The EL device according to claim 11 , 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

Assignees

• Udc Ireland Ltd

Inventors

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

Classifications

• C07D263/57

  Aryl or substituted aryl radicals · CPC title

• C07D235/18 Primary

  with aryl radicals directly attached in position 2 · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07F9/65324

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07D241/42

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring · CPC title