Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12069949-B2
Application number	US-202217815691-A
Country	US
Kind code	B2
Filing date	Jul 28, 2022
Priority date	Sep 7, 2017
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

Compounds that are organic radicals that can have a dual function. The compounds can be fluorescent emitters that emit in the near-IR. The compounds can also facilitate reverse intersystem crossing (RISC) to convert triplet excitons in an OLED to singlet excited states to maximize utilization of generated excitons in the OLED and approach 100% internal quantum efficiency.

First claim

We claim:

1. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer comprising a first compound selected from the group consisting of Formulae BB, BC, BD, BE, BF, and BG

wherein
X 1 to X 5 are independently selected from CR A or N;
X 6 to X 10 are independently selected from CR B or N;
X 11 to X 15 are independently selected from CR C or N;
X 16 to X 23 are independently selected from CR D or N;
X 24 to X 31 are independently selected from CR E or N;
R A , R B , R C , R D , and R E independently represent mono to the maximum allowable substitution, or no substitution;
each R 1 to R 5 , R A , R B , R C , R D , and R E 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; or optionally, any two adjacent R 1 to R 4 , or any two adjacent R A , R B , R C , R D , and R E , can join to form a ring;
each R N is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one of R 1 to R 5 , R A , R B , R C , R D , or R E includes a polycyclic group selected from the group consisting of:

and any aza-analogue of each thereof, wherein the polycyclic group is optionally substituted with R P , wherein R P is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein R F to R I are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
Z and Z 1 are independently selected from the group consisting of O, S, Se, NR N , CR′CR″, SiR′R″, and GeR′R″, wherein R′ and R″ are independently R N ;
with the proviso that the following compounds are excluded

wherein the organic layer further comprises a second compound, wherein the second compound is capable of emitting light by fluorescence or thermally activated delayed fluorescence; and
wherein the organic layer further comprises a host.

2. The OLED of claim 1 , wherein the polycyclic group is selected from the group consisting of

and aza-analogues thereof;
wherein R F to R M and R O are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and the polycyclic group is attached through one of R F to R M , R O or R′, wherein R′ is independently R N .

3. The OLED of claim 1 , wherein the first compound is selected from the group consisting of:

4. The OLED of claim 1 , wherein the first compound is selected from the group consisting of:

5. The OLED of claim 1 , wherein the organic layer is an emissive layer.

6. The OLED of claim 1 , wherein the first compound can produce emission.

7. The OLED of claim 1 , wherein the first compound produces emission via fluorescence or thermally activated delayed fluorescence.

8. The OLED of claim 1 , wherein the first compound is an emissive dopant.

9. The OLED of claim 1 , wherein the second compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Lu Tongxiang (Aaron)
• Thompson Nicholas J
• Margulies Eric A
• Fitzgerald George
• Feldman Jerald

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title