OLED with hybrid emissive layer

Patent metadata

Field	Value
Publication number	US-12029055-B2
Application number	US-201916262408-A
Country	US
Kind code	B2
Filing date	Jan 30, 2019
Priority date	Jan 30, 2018
Publication date	Jul 2, 2024
Grant date	Jul 2, 2024

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 .

First claim

We claim:

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.

Assignees

• Univ Southern California
• Univ Michigan Regents

Inventors

• Thompson Mark E
• Tadle Abegail
• Idris Muazzam
• El Roz Karim
• Muthiah Ravinson Daniel Sylvinson
• Forrest Stephen R
• Soh Chan Ho

Classifications

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/27

  Combination of fluorescent and phosphorescent emission · CPC title