Organic electroluminescent compound and organic photoelectric apparatus thereof

Patent metadata

Field	Value
Publication number	US-9899609-B2
Application number	US-201615164053-A
Country	US
Kind code	B2
Filing date	May 25, 2016
Priority date	Dec 25, 2015
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

The present disclosure provides a nitrogen-containing heterocyclic compound having a general formula (I) and an organic photoelectric apparatus thereof. The general formula (I) is:

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a hydrogen atom, a nitrile group and a function group having a general formula (II), and A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include at least one nitrile group and at least one function group having the general formula (II),
the general formula (II) being:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from hydrogen atoms, deuterium atoms, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group.

First claim

What is claimed is:

1. A nitrogen-containing heterocyclic compound having a general formula (I):

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a nitrile group and a functional group having a general formula (II), and A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include at least one nitrile group and at least one functional group having the general formula (II),
the general formula (II) being:

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from hydrogen atoms, deuterium atoms, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group.

2. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
A 1 , A 2 , A 3 , A 4 , and A 5 include at least one nitrile group and at least one functional group having the general formula (II); and
A 6 , A 7 , A 8 , A 9 , and A 10 include at least one nitrile group and at least one functional group having the general formula (II).

3. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
A 1 , A 2 , A 3 , A 4 , and A 5 include at least one nitrile group without having a functional group having the general formula (II);
A 6 , A 7 , A 8 , A 9 , and A 10 include at least one functional group having the general formula (II) without having a nitrile group; and
a quantity of the at least one nitrile group in A 1 , A 2 , A 3 , A 4 , and A 5 is less than or equal to a quantity of the functional group having the general formulation (II) in A 6 , A 7 , A 8 , A 9 , and A 10 .

4. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
an energy level difference (ΔE st ) between a lowest singlet state S 1 and a lowest triplet state T 1 of the nitrogen-containing heterocyclic compound is smaller than or equal to approximately 0.30 eV.

5. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are all hydrogen.

6. The nitrogen-containing heterocyclic compound according to claim 1 , comprising one of:

7. The nitrogen-containing heterocyclic compound according to claim 1 , comprising:
a thermally activated delayed fluorescence performance.

8. An organic photoelectric apparatus, comprising:
an anode substrate;
at least one organic layer formed over the anode substrate; and
a cathode layer formed over the organic layer,
wherein the at least one organic layer includes at least one nitrogen-containing heterocyclic compound of general formula (I):

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a nitrile group and a functional group having a general formula (II), and A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include at least one nitrile group and at least one functional group having the general formula (II),
the general formula (II) being:

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from hydrogen atoms, deuterium atoms, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group.

9. The organic photoelectric apparatus according to claim 8 , wherein the organic layer comprises:
at least one light-emitting layer; and
the at least one light emitting layer includes one or at least two nitrogen-containing heterocyclic compounds.

10. The organic photoelectric apparatus according to claim 9 , wherein the organic layer further comprises:
one or at least two of a hole transport layer, a hole injection layer, a hole barrier layer, an electron transport layer, an electron injection layer and an electron barrier layer.

11. The organic photoelectric apparatus according to claim 9 , wherein:
the one or at least two nitrogen-containing heterocyclic compounds are used as one of a host material, a doping material and a co-doping material of the at least one light-emitting layer.

12. The organic photoelectric apparatus according to claim 11 , wherein:
the one or at least two nitrogen-containing heterocyclic compounds are the host material of the at least one light-emitting layer.

13. The organic photoelectric apparatus according to claim 8 , wherein:
an energy level difference (ΔE st ) between a lowest singlet state S 1 and a lowest triplet state T 1 of the nitrogen-containing heterocyclic compound is smaller than or equal to approximately 0.30 eV.

14. A method for fabricating an organic photoelectric apparatus, comprising:
providing an anode substrate,
forming at least one organic layer over the anode substrate; and
forming a cathode layer over the organic layer,
wherein the at least one organic layer includes at least one nitrogen-containing heterocyclic compound having a general formula (I),

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a nitrile group and a functional group having a general formula (II), and A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include at least one nitrile group and at least one functional group having the general formula (II),
the general formula (II) being:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from hydrogen atoms, deuterium atoms, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group.

15. The method according to claim 14 , wherein the at least one organic layer comprises:
at least one light-emitting layer; and
the at least one light emitting layer includes one or at least two nitrogen-containing heterocyclic compounds.

16. The method according to claim 14 , wherein forming the at least one organic layer further comprises:
forming a hole transport layer on the anode substrate;
forming a light-emitting layer on the hole transport layer;
forming a hole barrier layer on the light-emitting layer;
forming an electron transport layer on the hole barrier layer; and
forming an electron injection layer on the electron transport layer.

17. The method according to claim 15 , wherein:
the one or at least two nitrogen-containing heterocyclic compounds are used as one of a host material, a doping material, and a co-doping material of the at least one light-emitting layer.

18. The method according to claim 14 , wherein:
the organic layer is formed by an evaporation process.

19. The method according to claim 14 , wherein:
an energy level difference (E st ) among a lowest singlet state S 1 and a lowest triplet state T 1 of the nitrogen-containing heterocyclic compound is smaller than or equal to approximately 0.30 eV.

20. The method according to claim 14 , whe

Assignees

• Shanghai Tianma Am Oled Co Ltd
• Tianma Micro Electronics Co Ltd
• Shanghai Tianma Am Oled Co Ltd

Inventors

• Ren Hongyang
• Wang Xiangcheng
• He Wei

Classifications

• H01L51/001

  Electricity · mapped topic

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L51/56

  Electricity · mapped topic