Indoloacridine-containing derivative, preparation process and use thereof, and organic luminescent device

Patent metadata

Field	Value
Publication number	US-9676767-B2
Application number	US-201414425254-A
Country	US
Kind code	B2
Filing date	May 30, 2014
Priority date	Dec 10, 2013
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

The disclosure provides an indoloacridine-containing derivative represented by formula (I), wherein A is a group represented by formula (II), and wherein X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represent a nitrogen atom; R represents a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group. The disclosure further provides a process for preparing the compound. The disclosure further provides an organic electroluminescent device comprising the compound. This compound can be used as a phosphorescence host material, a hole-injecting material or a hole-transporting material in an organic electroluminescent device.

First claim

What is claimed is:

1. An indoloacridine-containing derivative represented by the following molecular structural formula (I):

wherein A is a group represented by the formula (II):

wherein X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represents a nitrogen atom; and
wherein R represents a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group.

2. The indoloacridine-containing derivative according to claim 1 , wherein X represents a nitrogen atom.

3. The indoloacridine-containing derivative according to claim 2 , wherein X and Y represent a nitrogen atom.

4. The indoloacridine-containing derivative according to claim 3 , wherein X, Y and Z represent a nitrogen atom.

5. The indoloacridine-containing derivative according to claim 4 , wherein X, Y, Z and W represent a nitrogen atom.

6. The indoloacridine-containing derivative according to claim 1 , wherein R represents phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 3-biphenylyl or 9-phenanthryl.

7. The indoloacridine-containing derivative according to claim 1 , wherein the indoloacridine-containing derivative is any one selected from the compounds represented by the following chemical structural formulae (1) to (24):

8. A process for preparing the compound of claim 1 , comprising a step of reacting a compound represented by formula (III)

with a compound represented by formula (IV)

wherein R, X, Y, Z and W have the same definitions as those in claim 1 ,
wherein the process comprises the following Steps S1 to S3:
Step S1: adding the compound represented by formula (III), the compound represented by formula (IV), potassium hydroxide, copper iodide and a solvent into a degassed reaction container;
Step S2: increasing a reaction temperature and refluxing, allowing the reaction to be carried out; and
Step S3: performing filtration, washing and recrystallization to obtain the indoloacridine-containing derivative represented by formula (I).

9. The process according to claim 8 , wherein the process further comprises performing the following Steps M1 to M5 to produce the compound represented by formula (III):
Step M1: reacting 9,10-dihydro-9,9-dimethylacridine with solid triphosgene to obtain a compound represented by formula (V):

Step M2: reacting the compound represented by formula (V) with N-bromosuccinimide to obtain a compound represented by formula (VI):

Step M3: reacting the compound represented by formula (VI) with 2-chloroaniline to obtain a compound represented by formula (VII):

Step M4: reacting the compound represented by formula (VII) in the presence of palladium acetate, di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate, to obtain a compound represented by formula (VIII):

Step M5: removing the chloroformyl protection of the compound represented by formula (VIII) to obtain the compound represented by formula (III).

10. The process according to claim 8 , wherein the process further comprises producing the compound represented by formula (IV) by reacting R—B(OH) 2 with a compound represented by formula (IX):

wherein R, X, Y, Z and W have the same definitions as those in claim 1 .

11. The process according to claim 10 , wherein the compound represented by formula (IV) is obtained by the following Steps N1 to N3:
Step N1: adding the compound represented by formula (IX), R—B(OH) 2 , potassium carbonate and a solvent into a degassed reaction container;
Step N2: refluxing, and allowing the reaction to be carried out sufficiently;
Step N3: performing extraction, washing, drying and purification with column chromatography, to obtain the compound represented by formula (IV).

12. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more organic compound layer(s) provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises at least one indoloacridine-containing derivative according to claim 1 .

13. The organic electroluminescent device according to claim 12 , wherein the indoloacridine-containing derivative is a phosphorescence host material.

14. The organic electroluminescent device according to claim 13 , wherein the indoloacridine-containing derivative is a red phosphorescence host material.

Assignees

• Boe Technology Group Co Ltd
• Jilin Oled Mat Tech Co Ltd

Inventors

• Ma Wenyu
• Ma Xiaoyu
• Wang Hui
• Li Na

Classifications

• H01L2251/308

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C07D475/00

  Heterocyclic compounds containing pteridine ring systems · CPC title