Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12404271-B2
Application number	US-201916523168-A
Country	US
Kind code	B2
Filing date	Jul 26, 2019
Priority date	Jul 31, 2018
Publication date	Sep 2, 2025
Grant date	Sep 2, 2025

Abstract

An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, the emission layer including a condensed polycyclic compound of three or more six-membered rings, at least two six-membered rings among the six-membered rings including an electron donor moiety and an electron acceptor moiety at facing positions, respectively, the at least two six-membered rings not being immediately adjacent to each other, an electron transport region on the emission layer, and a second electrode on the electron transport region.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region, the emission layer including a condensed polycyclic compound of three or more six-membered rings, at least two six-membered rings among the six-membered rings including an electron donor moiety and an electron acceptor moiety at facing positions, respectively, the at least two six-membered rings not being immediately adjacent to each other;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and oxides thereof,
wherein the polycyclic compound is represented by any one among Formula 1 to Formula 3:

in Formula 1 to Formula 3,
A 1 to A 7 are each independently CO, BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , PSR 7 , SO, or SO 2 ,
D 1 to D 7 are each independently NR 8 , O, S, or Se,
W 1 to W 4 are each independently N or CR 9 ,
a to g are each independently 0 or 1,
rings M 1 to M 7 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 9 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
when D 3 is NR 8 and A 3 and A 4 are CO, D 4 is NR 8 , O, or Se,
when D 5 to D 7 are NR 8 , at least one Ra is a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
when, in Formula 1, W 1 and We are each CR 9 , A 1 and A 2 are each BR 1 , D 1 and D 2 are each NR 8 , and rings M 1 and M 2 are each a substituted or unsubstituted phenyl group, at least one selected from R 1 , R 9 , and rings M 1 and M 2 is substituted with a halogen atom, and
when M 1 and M 2 in Formula 1 are each a six-membered ring, i) D 1 and D 2 are each not NR 8 , or ii) at least one selected from A 1 and A 2 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 , and when M 3 and M 4 in Formula 2 are each a six-membered ring, iii) D 3 and D 4 are each not NR 8 , or iv) at least one selected from A 3 and A 4 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 .

2. The organic electroluminescence device as claimed in claim 1 , wherein:
the emission layer is a delayed fluorescence emission layer including a host and a dopant, and
the host or the dopant includes the polycyclic compound.

3. The organic electroluminescence device as claimed in claim 1 , wherein:
the emission layer is a phosphorescence emission layer including a host and a dopant, and
the host includes the polycyclic compound.

4. The organic electroluminescence device as claimed in claim 1 , wherein the electron donor moiety includes an amine group, an oxygen atom, a sulfur atom, or a selenium atom.

5. The organic electroluminescence device as claimed in claim 1 , wherein the electron acceptor moiety includes a carbonyl group, a boron group, a silyl group, a germyl group, a phosphine oxide group, a phosphine sulfide group, a sulfoxide group, or a sulfur dioxide group.

6. The organic electroluminescence device as claimed in claim 1 , wherein the emission layer emits blue light.

7. The organic electroluminescence device as claimed in claim 1 , wherein A 1 to A 7 are represented by the following Formula 4:

in Formula 4,
V 1 to V 5 are each independently N, CR 10 , or CR 11 , provided that at least one among V 1 to V 5 is CR 11 ,
R 10 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and
R 11 is a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

8. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 to Formula 3 are represented by the following Formula 1-1 to Formula 1-3, respectively:

in Formulae 1-1 to 1-3,
R 21 to R 34 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and
A 1 to A 7 , D 1 to D 7 , and W 1 to W 4 are the same as defined in Formula 1 to Formula 3.

9. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 to Formula 3 are represented by the following Formula 2-1 to Formula 2-3, respectively:

in Formula 2-1 to Formula 2-3,
R 35 to R 62 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide

Assignees

• Samsung Display Co Ltd

Inventors

• YAMATANI Akinori

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K2101/10

  Triplet emission · CPC title