Oled with hybrid emissive layer

Patent metadata

Field	Value
Publication number	US-2019237694-A1
Application number	US-201916262408-A
Country	US
Kind code	A1
Filing date	Jan 30, 2019
Priority date	Jan 30, 2018
Publication date	Aug 1, 2019
Grant date	—

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 T1H and a singlet state energy level S1H, a second material having a triplet state energy level T1F and a singlet state energy level S1F; and a third material having a triplet state energy level T1P and a single state energy level S1P, where T1F≥T1H; S1F≤S1H; and T1P<T1H.

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 .

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 9 . wherein the energy gap between S1 F and T1 F is 0.1 eV to 0.8 eV.

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

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

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

14 . The OLED of claim 1 , wherein the fluorescent emissive dopant has a fluorescence efficiency of at least 60%.

15 . The OLED of claim 1 , wherein the second material is selected from compounds A, B, C, and/or D:

16 . The OLED of claim 1 , wherein the first material comprises a compound selected from the group consisting of:

wherein
R is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkenyl, aryl, heteroaryl, and combinations thereof.

17 . The OLED of claim 1 , wherein the first material comprises a compound selected from the group consisting of:

wherein
ring members 1 to 4 are independently selected from CR P or N, wherein no more than two of ring members 1 to 4 are N, and each group R P 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, sulfonyl, phosphino, and combinations thereof.

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

19 . 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 1 or W 4 is C that is substituted with Ar 1 ;
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 1 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 fuzed 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 fuzed aromatic ring, which is optionally substituted.

20 . A compound of claim 19 selected from the group consisting of

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

21 . The compound of claim 12 , wherein Ar 1 and A 2 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 the Ring A.

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

• C07D233/58

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• H01L2251/5376

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic