Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9780316-B2
Application number	US-201514659228-A
Country	US
Kind code	B2
Filing date	Mar 16, 2015
Priority date	Mar 16, 2015
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

A compound having the structure of Formula I

is disclosed, where G a has the structure

and G b has the structure

In the structure of Formula I, Z is selected from Si and Ge; X a and X b are independently selected from the group consisting of O, S, and Se; the Y and Z atoms forming the six-membered rings in Formula I, G a , and G b are each independently selected from C or N; each R 1 , R 2 , R a1 , R a2 , R b1 , and R b2 is independently selected from a variety of substituents; at least one R a1 is L a -A a ; at least one R b1 is L b -A b ; A a and A b are each independently selected from carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, triphenylene, and nitrogen-substituted variants thereof, which are optionally further substituted; and L a and L b are each independently an organic linker. Formulations and devices, such as an OLEDs, that include the compound of Formula I are also described.

First claim

We claim:

1. A compound having the structure of Formula I:

wherein G a has the structure

wherein G b has the structure

wherein Z is selected from Si and Ge;
wherein X a and X b are independently selected from the group consisting of O, S, and Se;
wherein Y a1 -Y a3 , Y a6 -Y a9 , Y b1 -Y b3 , Y b6 -Y b9 , Z a2 -Z a6 and Z b2 -Z b6 are each independently selected from C or N;
wherein R 1 and R 2 each independently represent mono, di, tri, tetra, or penta substitution, or no substitution;
wherein R a1 and R b1 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a2 and R b2 each independently represent mono, di, or tri substitution, or no substitution;
wherein each R 1 , R 2 , R a1 , R a2 , R b1 , and R b2 is 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, phosphine, and combinations thereof;
wherein at least one R a1 is L a -A a ;
wherein at least one R b1 is L b -A b ;
wherein A a and A b are each independently selected from the group consisting of carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene and azatriphenylene which are optionally further substituted, and wherein the substitution is optionally fused to at least one benzo or azabenzo ring; and
wherein L a and L b are each independently selected from the group consisting of a direct connection and an organic linker.

2. The compound according to claim 1 , wherein each one of Z a2 -Z a6 and Z b2 -Z b6 is carbon.

3. The compound according to claim 1 , wherein each one of Y a1 -Y a3 , Y a6 -Y a9 , Y b1 -Y b3 , and Y b6 -Y b9 is carbon.

4. The compound according to claim 1 , wherein exactly one of Y a1 -Y a3 and Y a6 -Y a9 is nitrogen.

5. The compound according to claim 1 , wherein exactly one of Y b1 -Y b3 and Y b6 -Y b9 is nitrogen.

6. The compound according to claim 1 , wherein G a and G b are the same.

7. The compound according to claim 1 , wherein G a and G b are different.

8. The compound according to claim 1 , wherein linkers L a and L b are independently selected from the group consisting of a direct connection, alkyl, aryl, heteroaryl, and combinations thereof.

9. The compound according to claim 1 , wherein linkers L a and L b are independently selected from the group consisting of:
a direct connection,

wherein X 1 to X 8 are C or N,
wherein Y is N, O or S, and
wherein each one of L1 through L23 may be further substituted by substituents 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.

10. The compound according to claim 1 , wherein linkers L a and L b are independently selected from the group consisting of: a direct connection,

which may be further substituted by substituents 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.

11. The compound according to claim 1 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Tsang Kit Yee
• Lam Siu Tung

Classifications

• H01L51/0074

  Electricity · mapped topic

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• H01L27/3244

  Electricity · mapped topic

• C07F7/0814 Primary

  said ring is substituted at a C ring atom by Si · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title