Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12274165-B2
Application number	US-202218066085-A
Country	US
Kind code	B2
Filing date	Dec 14, 2022
Priority date	Feb 27, 2014
Publication date	Apr 8, 2025
Grant date	Apr 8, 2025

Abstract

Novel host compounds consisting of carbazole and nitrile groups are disclosed. These compounds are useful in phosphorescent OLEDs.

First claim

The invention claimed is:

1. A compound having the following formula:
A-L-B,  Formula I;

wherein A is selected from the group consisting of:

wherein Z 1 , Z 2 , z 3 , Z 4 , Z 5 , Z 6 , and Z 7 are independently selected from the group consisting of N and CR 1 ;
wherein each R 1 is 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, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the dashed lines in A represent the bonds between A and L;
wherein L is selected from the group consisting of benzene, biphenyl, terphenyl, pyridine, and combinations thereof;
wherein B is selected from the group consisting of biphenyl, terphenyl, triphenylene, phenanthrene, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-triphenylene, pyridine, triazine, pyrimidine, and combinations thereof;
wherein B is optionally further substituted with one or more substituents selected from the group consisting of 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, with the proviso that B is not further substituted by anthracene; and
if B comprises pyridine, triazine, or pyrimidine, then the pyridine, triazine, or pyrimidine is substituted by at least one heteroaryl.

2. The compound of claim 1 , wherein Z 1 , Z 2 , z 3 , Z 4 , z 5 , Z 6 , and Z 7 are CR 1 .

3. The compound of claim 1 , wherein each R 1 is independently selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, and combinations thereof.

4. The compound of claim 1 , wherein each R 1 is independently selected from the group consisting of hydrogen, deuterium, benzene, biphenyl, terphenyl, dibenzofuran, dibenzothiophene, triphenylene, carbazole, fluorene and combinations thereof.

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

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

and
wherein X is selected from the group consisting of O, S and Se.

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

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

9. The compound of claim 1 , wherein the compound is Compound x having the formula A i -L j -B k ;
wherein x=570k+38j+i−608, i is an integer from 1 to 38, j is an integer from 2 to 15, and k is an integer from 1 to 11 and 16 to 24; and
wherein A 1 to A 38 have the following structures:

wherein L 2 to L 15 have the following structures:

and
wherein B 1 to B 11 and B 16 to B 24 have the following structures:

10. A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the following formula:
A-L-B,  Formula I;

wherein A is selected from the group consisting of:

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , and Z 7 are independently selected from the group consisting of N and CR 1 ;
wherein each R 1 is 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, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, benzene, biphenyl, terphenyl, dibenzofuran, dibenzothiophene, triphenylene, carbazole, fluorene, and combinations thereof;
wherein the dashed lines in A represent the bonds between A and L;
wherein L is selected from the group con

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Xia Chuanjun

Classifications

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/6576

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

• H10K85/622

  containing four rings, e.g. pyrene · CPC title

• H10K85/342

  comprising iridium · CPC title