Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10008679-B2
Application number	US-201514672034-A
Country	US
Kind code	B2
Filing date	Mar 27, 2015
Priority date	Apr 14, 2014
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

Phosphorescent complexes are designed with intramolecular H-bonding properties to prevent deprotonation of neighboring molecules.

First claim

We claim:

1. A compound comprising a ligand L selected from the group A consisting of:

wherein X 7 is Z 2 ; and

wherein X 9 is Z 2 ;
wherein each X 1 , X 3 , X 4 , and X 5 are carbon, and X 2 , and X 6 to X 11 are independently selected from carbon or nitrogen;
wherein each R a , R b , and R c may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein each R a , R b , and R c 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 when R a , R b , and R c represent at least di substitution, each of the two adjacent R a , two adjacent R b , and two adjacent R c are optionally fused or joined to form a ring;
wherein the ligand L is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein the ligand L is optionally linked to provide a tridentate, or tetradentate-ligand;
wherein the compound comprises at least one intramolecular hydrogen bonding interaction as shown
Z 1 —H----Z 2

wherein Z 1 is carbon of alkyl, and Z 2 is nitrogen
and
the proton NMR chemical shift of H is shifted downfield by at least 1.3 ppm compared to the compound when Z 2 is carbon.

2. The compound of claim 1 , wherein the compound has an emission with the first peak wavelength at the high energy end smaller at room temperature than that at 77K.

3. The compound of claim 1 , wherein M is Ir or Pt.

4. The compound of claim 1 , wherein the compound has a formula of Ir(L) n (L′) 3-n ;
wherein L′ is selected from group A; and
wherein n is 1, 2, or 3.

5. The compound of claim 1 , wherein the compound has a formula of Pt(L) m (L′) 2-m ;
wherein L′ is selected from group A; and
wherein m is 1 or 2.

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

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

8. 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 comprising a ligand L of claim 1 .

9. The first device of claim 8 , wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

10. The first device of claim 8 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

11. The first device of claim 8 , wherein the organic layer further comprises a host; wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , C n H 2n —Ar 1 , or no substitution;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

12. The first device of claim 8 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

13. The first device of claim 8 , wherein the organic layer further comprises a host and the host is selected from the group consisting of:

and combinations thereof.

14. The compound of claim 1 , wherein X 5 , X 6 , and X 8 are carbon, and are each substituted with R b , wherein R b is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, aryl, and heteroaryl.

15. The compound of claim 14 , wherein X 6 and X 9 are Z 2 .

16. The compound of claim 1 , wherein X 6 , X 7 , and X 9 are carbon, and are each substituted with R c , wherein R c is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, aryl, and heteroaryl.

17. The compound of claim 16 , wherein X 5 and X 8 are Z 2 .

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Beers Scott
• Szigethy Geza
• Brooks Jason

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

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