Organic molecules for use as emitters

Patent metadata

Field	Value
Publication number	US-10651394-B2
Application number	US-201515506346-A
Country	US
Kind code	B2
Filing date	Sep 17, 2015
Priority date	Sep 17, 2014
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The invention relates to purely organic molecules according to formula A without metal center and their use as emitters in organic light-emitting diodes (OLEDs) and in other optoelectronic devices

with
Y is independently selected from the group consisting of C, PR, S, and S(═O); W is independently selected from the group consisting of C(CN) 2 , NR, O, and S; X is selected from the group consisting of CR 2 , C═C(CN) 2 , NR, O, and S; Ar is a substituted aryl or heteroaryl group with 5 to 40 aromatic ring atoms, which is substituted with m same or different radicals R* and with n same or different donor groups D with electron-donating properties, wherein m+n equals the number of substitutable ring atoms and wherein D comprises a structure of formula I:

wherein
A and B are independently selected from the group consisting of CRR′, CR, NR, and N, wherein there is a single of a double bond between A and B and a single or a double bond between B and Z; Z is a direct bond or a divalent organic bridge group selected from the group consisting of a substituted or unsubstituted C1-C9-alkylene group, C2-C8-alkenylene group, C2-C8-alkynylene or arylene group or a combination of these, —CRR′, —C═CRR′, —C═NR, —NR—, —O—, —SiRR′—, —S—, —S(O)—, —S(O) 2 —, O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene groups, and phenyl or substituted phenyl units; wherein the waved line indicates the position over which D is bound to Ar.

First claim

The invention claimed is:

1. An organic molecule comprising a structure of formula D:

wherein
R″ is R or an organic bridge via which a second same or different unit of formula D is bound forming a dimeric system and wherein at least one R at the aryl ring is a donor group comprising a structure of formula I

wherein
A and B are independently selected from the group consisting of CRR′, CR, NR, and N, wherein there is a single or a double bond between A and B and a single or a double bond between B and Z;
Z is a direct bond or a divalent organic bridge group selected from the group consisting of a substituted or un substituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group or a combination of these, —CRR′, —C═CRR′, —C═NR, —NR—, —O—, —SiRR′—, —S—, —S(O)—, —S(O) 2 —, and O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene groups, or phenyl or substituted phenyl units; wherein the waved line indicates the position over which R is bound to the aryl ring;
wherein each R and R′ at each occurrence is the same or different H, deuterium, azide (N 3 − ), F, Cl, Br, I, N(R 2 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 2 , CO(NR 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C-atoms or a linear alkenyl or alkynyl group with 2 to 40 C-atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C-atoms, which each can be substituted by one or more radicals R 2 , wherein one or more not adjacent CH 2 -groups can be 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, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and wherein one or more H-atoms can be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which each can be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 2 , or a combination of these systems, or a cross-linkable unit, whereby two or more of the substituents R and R′ can also form with each other a mono- or polycyclic, aliphatic, aromatic and/or benzoannulated ring system;
R 2 is at each occurrence is the same or different H, deuterium, F, Cl, Br, I, N(R 3 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 3 , CO(NR 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C-atoms or a linear alkenyl or alkynyl group with 2 to 40 C-atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C-atoms, which each can be substituted by one or more radicals R 3 , wherein one or more not adjacent CH 2 -groups can be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and wherein one or more H-atoms can be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which each can be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 3 , or a combination of these systems; whereby two or more of these substituents R 2 can also form with each other a mono- or polycyclic, aromatic and/or benzoannulated ring system;
R 3 is at each occurrence is the same or different H, deuterium, F, CF 3 or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical with 1 to 20 C-atoms, in which one or more H-atoms can be replaced by F or CF 3 ; whereby two or more substituents R 3 can form with each other a mono- or polycyclic aliphatic ring system,
wherein at least one of the donor groups of formula I comprises a structure of formula II:

wherein
Z is a direct bond or a divalent organic bridge group selected from the group consisting of a substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene group or a combination of these, —CRR′, —C═CRR′, —C═NR—, —NR—, —O—, —SiRR′—, —S—, —S(O)—, —S(O) 2 —, and O-interrupted substituted or unsubstituted C1-C9-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or arylene groups, phenyl or substituted phenyl units; wherein the waved line indicates the linkage position of D;
each R and R′ at each occurrence is same or different H, deuterium, F, Cl, Br, I, N(R 2 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 2 , CO(NR 2 ) 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)(R 2 ), P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C-atoms or a linear alkenyl or alkenyl group with 2 to 40 C-atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C-atoms, which each can be substituted by one or more radicals R 2 , wherein one or more not adjacent CH 2 -groups 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, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and wherein one or more H-atoms can be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which each can be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2 , a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 2 , or a combination of these systems, or a cross-linkable unit, which can be cross-linked by acid-catalyzed thermal or UV cross-linking processes; thereby two or more of the substituents R and R′ can form with each other a mono- or polycyclic, aliphatic, aromatic and/or benzoannulated ring system;
R 2 is at each occurrence is the same or different H, deuterium F, Cl, Br, I, N(R 3 ) 2 , CN, CF 3 , NO 2 , OH, COOH, COOR 3 , CO(NR 3 ) 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 C-atoms or a linear alkenyl or alkynyl group with 2 to 40 C-atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C-atoms, which each can be substituted by one or more radicals R 3 , wherein one or more not adjacent CH 2 -groups can be replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and wherein one or more H-atoms can be replaced by deuterium, F, Cl, Br, I, CN, CF 3 or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which each can be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which

Assignees

• Cynora Gmbh

Inventors

• Danz Michael

Classifications

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/104

  with other heteroatoms · CPC title

• H01B1/12

  organic substances {(organic macromolecular compounds or compositions C08)} · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title