Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9929353-B2
Application number	US-201514636310-A
Country	US
Kind code	B2
Filing date	Mar 3, 2015
Priority date	Apr 2, 2014
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

Novel host compounds containing indolo[3,2,1-jk]carbazole moiety are disclosed. These compounds are useful in phosphorescent OLEDs and particularly as hosts and/or electron-blocking layer materials.

First claim

We claim:

1. A compound having a structure according to a formula G 1 -G 2 -G 3 -G 4 -G 5 , Formula I;
wherein G 1 has the structure:

wherein R 1 and R 3 each independently represent mono, di, tri, or tetra substitutions, or no substitution,
wherein R 2 represents mono, di, or tri substitutions, or no substitution,
wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein G 2 and G 4 are each independently selected from the group consisting of a direct bond, an aryl group having from 6-30 carbon atoms, a heteroaryl group having from 3-30 carbon atoms, and combinations thereof, wherein the aryl group and the heteroaryl group are optionally further substituted with one or more groups selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein G 3 and G 5 are each independently a carbazole or a carbazole that is substituted with one or more groups selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein the structure according to Formula I is further defined according to at least one of:

wherein R 6 , and R 7 each independently represents mono, di, tri, or tetra substitutions, or no substitution;
wherein R 6 , and R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein R 4 represents mono, di, or tri substitutions, or no substitution;
wherein R 5 represents mono, di, tri, or tetra substitutions, or no substitution;
wherein R 4 , R 5 , and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein R 4 represents mono, di, or tri substitutions, or no substitution;
wherein R 5 represents mono, di, tri, or tetra substitutions, or no substitution;
wherein R 4 , R 5 , and R 8 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein G 1 connects to G 2 at the ring having R 2 substituent.

3. The compound of claim 1 , wherein G 1 connects to G 2 at the ring having R 3 substituent.

4. The compound of claim 1 , wherein G 2 and G 4 are each a direct bond.

5. The compound of claim 1 , wherein the compound has a structure selected from the group consisting of:

wherein R 4 , R 6 , and R 7 each independently represents mono, di, tri, or tetra substitutions, or no substitution;
wherein R 5 represents mono, di, or tri, substitutions, or no substitution;
wherein R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

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

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

8. A formulation comprising the compound in claim 1 .

9. A device comprising one or more organic light emitting devices, at least one of the organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure according to the formula G 1 -G 2 -G 3 -G 4 -G 5 , Formula I;
wherein G 1 has the structure:

wherein R 1 and R 3 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono, di, or tri substitution, or no substitution;
wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein G 2 and G 4 are each independently selected fro

Assignees

• Universal Display Corp

Inventors

• Kottas Gregg
• Elshenawy Zeinab
• Xia Chuanjun
• Zeng Lichang

Classifications

• H01L51/0072 Primary

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/5024

  Electricity · mapped topic

• C07D487/06 Primary

  Peri-condensed systems · CPC title

• H01L51/5016

  Electricity · mapped topic