9 membered ring carbazole compounds

Patent metadata

Field	Value
Publication number	US-11038121-B2
Application number	US-201916378559-A
Country	US
Kind code	B2
Filing date	Apr 8, 2019
Priority date	Apr 9, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Novel 9 membered ring carbazole compounds are disclosed, which can be used as host materials etc. in an electroluminescent device. Compared with the existing host materials etc., these novel compounds can effectively modulate the charge transporting properties in the above materials and give OLEDs better performance. Also disclosed are an electroluminescent device and a formulation.

First claim

What is claimed is:

1. A compound comprising Formula 1:

wherein
X 1 to X 19 are each independently selected from CR, or N;
R are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Any adjacent substitution can be optionally joined to form a ring.

2. The compound of claim 1 , wherein X 1 to X 19 are each independent CR.

3. The compound of claim 1 , wherein the compound comprises a Formula 2 structure:

Wherein
R 1 , R 3 , R 4 , and R 5 independently represent mono, di, tri, tetra substitution, or no substitution;
R 2 independently represent mono, di, tri substitution, or no substitution;
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Any adjacent substitution can be optionally joined to form a ring.

4. The compound of claim 1 , wherein the compound comprises a structure of any one of Formula 3-6:

Wherein
R 1 , R 3 , R 4 , R 5 , R 6 , and R 7 independently represent mono, di, tri, tetra substitution, or no substitution;
R 2 independently represent mono, di, tri substitution, or no substitution;
X, are each independently selected from the group consisting of O, S, Se, NR′, CR″R′″ and SiR″″R′″″;
Y are each independently selected from the group consisting of O, S, NR′, CR″R′″ and SiR″″R′″″;
R′, R″, R″″, R′″″, R′″″, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Any adjacent substitution can be optionally joined to form a ring;
L is selected from the group consisting of:

Single bond.

5. The compound of claim 1 , wherein the compound comprises a structure of any one of Formula 7-9:

Wherein
R 1 independently represent mono, di, tri, tetra substitution, or no substitution;
R 2 , R 3 , R 4 , and R 5 independently represent mono, multi substitution, or no substitution; said multi substitution refer to a range that includes di substitution, up to the maximum available substitutions of the formula;
Z are each independently selected from the group consisting of O, S, NR′, CR″R′″ and SiR″″R′″″;
R′, R″, R″″, R′″″, R′″″, R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Any adjacent substitution can be optionally joined to form a ring.

6. The compound of claim 3 , wherein R 1 , and R 2 are each independently selected from the group consisting of:

Assignees

• Beijing Summer Sprout Tech Co Ltd

Inventors

• Xia Chuanjun

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D495/16 Primary

  Peri-condensed systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title