IP Library Granted Patent US 12,029,055
Granted Patent B2
US 12,029,055 · App. 16/262,408 · Granted Jul 2, 2024

OLED with hybrid emissive layer

Inventors: Mark E. Thompson (Anaheim, CA); Abegail Tadle (Bakersfield, CA); Muazzam Idris (Los Angeles, CA); Karim El Roz (Los Angeles, CA); Daniel Sylvinson Muthiah Ravinson (Los Angeles, CA); Stephen R. Forrest (Ann Arbor, MI); Chan Ho Soh (Ann Arbor, MI)
Assignees: The University of Southern California; The Regents of the University of Michigan
H10K50/11C07D233/58C07D401/10C09K11/06H10K50/125H10K85/322H10K85/654H10K85/6572C09K2211/1018H10K2101/10H10K2101/27H10K2101/30H10K2101/90
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Quick Facts
Patent No.
US 12,029,055
App. No.
16/262,408
Granted
Jul 2, 2024
Kind
B2
Abstract

A hybrid emissive layer and OLED incorporating the same are provided. The hybrid emissive layer includes a first material having a triplet state energy level T1 H and a singlet state energy level S1 H , a second material having a triplet state energy level T1 F and a singlet state energy level S1 F ; and a third material having a triplet state energy level T1 P and a single state energy level S1 P , where T1 F T1 H ; S1 F S1 H ; and T1 P <T1 H .

Claims (43)

1. An organic light emitting diode (OLED) comprising:

an anode;

a cathode; and

a hybrid first emissive layer disposed between the anode and the cathode, wherein the hybrid emissive layer comprises:

a first material having a triplet state energy level T1 H and a singlet state energy level S1 H ;

a second material having a triplet state energy level T1 F and a singlet state energy level S1 F ; and

a third material having a triplet state energy level T1 P and a single state energy level S1 P ;

wherein:

T1 F T1 H ; S1 F S1 H and T1 P <T1 H ;

wherein the first material is a compound of Formula I:

wherein

W 1 and W 2 are independently selected from C, CH, or N; wherein one of W 1 or W 2 is C that is substituted with Ring A;

W 3 and W 4 are independently selected from C, CR W , or N, and n is 0 or 1, wherein if n is 1 then one of W 3 or W 4 is C that is substituted with AO;

Z 1 , Z 2 , and Z 3 are independently selected from CR A or N, and at least one of Z 1 , Z 2 , or Z 3 is N;

V 1 and V 2 are independently selected from CR C or N;

V 3 and V 4 are independently selected from CR B or N; and

Ar 1 is selected from an optionally substituted aryl, or an optionally substituted heteroaryl;

R W is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, heterocyclic, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof;

each R A is independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, heterocyclic, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof; or optionally, two adjacent R A join to form a fused aromatic ring, which is optionally substituted;

R B and R C independently represent from mono substitution to the maximum possible number of substitution, or no substitution; and

each R B and R C is independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, heterocyclic, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof, or optionally, two adjacent R B or R C join to form a fused aromatic ring, which is optionally substituted.

2. The OLED of claim 1 , wherein the second material is a fluorescent emissive material.

3. The OLED of claim 1 , wherein the third material is a phosphorescent emissive material.

4. The OLED of claim 1 , wherein T1 H is at least 0.1 eV greater than T1 P .

5. The OLED of claim 1 , wherein T1 F is at least 0.1 eV greater than T1 H .

6. The OLED of claim 1 , wherein all emission by the OLED is from the first material.

7. The OLED of claim 6 , further comprising a second emissive layer, the second emissive layer comprising the first material.

8. The OLED of claim 6 wherein the first and second materials are the same material.

9. The OLED of claim 1 , wherein the energy gap between S1 F and T1 F is 0.05 eV to 0.8 eV.

10. The OLED of claim 1 , wherein T1 H is 2.4 eV to 2.6 eV.

11. The OLED of claim 1 , wherein S1 H is at least 3.5 eV.

12. The OLED of claim 1 , wherein T1 P is 1.7 to 2.5 eV.

13. The OLED of claim 2 , wherein the fluorescent emissive material has a fluorescence efficiency of at least 60%.

14. The OLED of claim 1 , wherein the second material is selected from compounds A and B:

wherein each R 1 to R 12 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

15. The OLED of claim 1 , wherein the second material emits light with a peak wavelength of 400 nm to 510 nm.

16. The OLED of claim 1 , wherein the compound is selected from the group consisting of

wherein m is 0 or 1, and Ar 2 is aryl or heteroaryl, each of which is optionally substituted.

17. The OLED of claim 1 , wherein Ar 1 and R A are independently selected from the group consisting of

and combinations thereof, or any one aza variant thereof,

wherein X is selected from O, S, or Se;

R, R′, and R″ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, amino, silyl, alkynyl, aryl, heteroaryl, and combinations thereof; and

the dotted line represents attachment to Formula I.

Assignments (3)
CONFIRMATORY LICENSE Recorded Jan 25, 2022
From: UNIVERSITY OF SOUTHERN CALIFORNIA
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 058838/0224 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2020
From: THOMPSON, MARK E.; TADLE, ABEGAIL; IDRIS, MUAZZAM; EL ROZ, KARIM; MUTHIAH RAVINSON, DANIEL SYLVINSON
To: UNIVERSITY OF SOUTHERN CALIFORNIA
Reel/Frame 054249/0054 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2020
From: FORREST, STEPHEN R; SOH, CHAN HO
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 054223/0200 →
Continuity (2)
Provisional Application 62623764 · Jan 30, 2018
Related Publication 20190237694A1 · Aug 1, 2019