Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same

Patent metadata

Field	Value
Publication number	US-9293712-B2
Application number	US-201414486468-A
Country	US
Kind code	B2
Filing date	Sep 15, 2014
Priority date	Oct 11, 2013
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

Compounds according to Formula 1, devices containing the same and formulations containing the same are described. Formula 1 has the following structure:

where at least two of R 1 —R 10 are not H,
where at least one of R 1 —R 10 has the formula T1

where L is an organic linker,
where Y 1 to Y 4 are CR or N,
where adjacent R moieties can form fused rings,
where R s and R t are independently aryl or heteroaryl, either of which may independently be further substituted, and
where R s and R t do not form fused rings with any part of the molecule.

First claim

We claim:

1. A compound having Formula 1:

wherein R 1 —R 10 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein at least two of R 1 —R 10 are not H,
wherein at least one of R 1 —R 10 has the formula T1

wherein L is an organic linker,
wherein Y 1 to Y 4 are CR or N,
wherein R is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein adjacent R moieties can form fused rings,
wherein R s and R t are independently aryl or heteroaryl, either of which may independently be further substituted, and
wherein R s and R t do not form fused rings with any part of the molecule.

2. The compound of claim 1 , wherein linker L is alkyl, aryl or heteroaryl.

3. The compound of claim 1 , wherein R s can comprise a moiety selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-dibenzothiophene, aza-dibenzofuran, or aza-dibenzoselenophene, phenyl, pyridine, and combinations thereof.

4. The compound of claim 1 , wherein linker L is selected from the group consisting of:

wherein X 1 to X 8 are CR′ or N,
wherein Y is NR″, O or S, and
wherein R′ and R″ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

5. The compound of claim 1 , wherein R 1 has the formula

6. The compound of claim 1 , wherein R 1 has the formula

and R 6 is alkyl, aryl or heteroaryl.

7. The compound of claim 6 , wherein the compound is selected from the group consisting of:

8. The compound of claim 1 , wherein the compound is selected from the group consisting of:

9. The compound of claim 1 , wherein R 1 has the formula

and R 6 is amino.

10. The compound of claim 9 , wherein the compound is selected from the group consisting of:

11. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having Formula 1:

wherein R 1 —R 10 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein at least two of R 1 —R 10 are not H,
wherein at least one R 1 —R 10 has the formula T1

wherein L is an organi

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Tsang Kit Yee
• Lam Sze Kui

Classifications

• H01L51/0059

  Electricity · mapped topic

• H01L51/0054 Primary

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic