Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12089486-B2
Application number	US-201815874057-A
Country	US
Kind code	B2
Filing date	Jan 18, 2018
Priority date	Feb 8, 2017
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

The present invention includes novel compounds having a boron containing ring for use as charge transporters, hosts or emitters in OLEDs.

First claim

We claim:

1. A compound having Formula I:
G 1 L-G 2 ) n ,  Formula I;

wherein G 1 is selected from the group consisting of:

wherein X 1 is selected from the group consisting of O, S, and Se;
wherein in each structure G 1 , at least one of R 1 to R 5 is L-G 2 ;
wherein n is an integer from 1 to 20;
wherein L is an organic linker;
wherein R 1 to R 5 and G 2 are each 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, a boron containing group, and combinations thereof;
wherein any two adjacent substituents can optionally join or fuse to form a ring, provided that L does not join or fuse to form a ring with any adjacent substituent;
wherein at least one of G 2 is a substituted or unsubstituted group selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenphene, carbazole, fluorene, triphenylene, azadibenzofuran, azadibenzothiophene, azadibenzoselenphene, azatriphenylene, triazine, pyrimidine, pyridine, and quinazoline;
provided that the triphenylene group is not fused to any additional rings.

2. The compound of claim 1 , wherein at least one L is attached to a boron atom.

3. The compound of claim 1 , wherein at least one L is attached to a nitrogen atom.

4. The compound of claim 1 , wherein n is 1, 2, 3, or 4.

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

6. The compound of claim 1 , wherein G 2 is selected from the group consisting of:

wherein X is selected from the group consisting of O, S, Se, NR, and CR 2 ; and
wherein R a , R b , and each occurrence of R 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, boron containing group, and combinations thereof; wherein any two adjacent substituents can optionally join or fuse to form a ring.

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

wherein each L and G 2 can be same or different.

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

9. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having Formula I:
G 1 L-G 2 ) n ,  Formula I;

wherein G 1 is selected from the group consisting of:

wherein X 1 is selected from the group consisting of O, S, and Se;
wherein in each structure G 1 , at least one of R 1 to R 5 is L-G 2 ;
wherein n is an integer from 1 to 5;
wherein L is an organic linker;
wherein R 1 to R 5 and G 2 are each 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, a boron containing group, and combinations thereof;
wherein any two adjacent substituents can optionally join or fuse to form a ring, provided that L does not join or fuse to form a ring with any adjacent substituent;
wherein at least one of G 2 is a substituted or unsubstituted group selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenphene, carbazole, fluorene, triphenylene, azadibenzofuran, azadibenzothiophene, azadibenzoselenphene, azatriphenylene, triazine, pyrimidine, pyridine, and quinazoline;
provided that the triphenylene group is not fused to any additional rings.

10. The OLED of claim 9 , wherein the organic layer is an emissive layer and the compound of Formula I is a host; or the organic layer is an emissive layer and the compound of Formula I is an emitter.

11. The OLED of claim 9 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d are each 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; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

12. The OLED of claim 9 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or a transporting layer and the compound of Formula I is a transporting material in the organic layer.

13. A consumer product comprising an organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having Formula I:
G 1 L-G 2 ) n ,  Formula I;

wherein G 1 is selected from the group consisting of:

wherein X 1 is selected from the group consisting of O, S, and Se;
wherein in each structure G 1

Assignees

• Universal Display Corp

Inventors

• Fitzgerald George
• Lin Chun
• Dyatkin Alexey Borisovich
• Lahti Paul M

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/322 Primary

  comprising boron · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/171

  Electron injection layers · CPC title