IP Library › Granted Patent US 10,734,586

Granted Patent B2

US 10,734,586 · App. 15/447,704 · Granted Aug 4, 2020

Organic light emitting device

Inventors: Yoshimasa Fujita (Yokohama, JP); Shuri Sato (Yokohama, JP); Hiroaki Itoi (Yokohama, JP)

H01L51/0061 C07C211/54 C07C211/58 C07D209/80 C07D209/86 C07D307/91 C07D405/14 C07F7/081 C07F7/0812 C07F7/0816 H01L51/006 H01L51/0054 H01L51/0059 H01L51/0071 H01L51/0072 H01L51/0073 H01L51/0094 H01L51/0052 H01L51/0058 H01L51/5024 H01L51/5056 H01L51/5064 H01L51/5072 H01L51/5088 H01L51/5092 H01L51/5096

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Quick Facts

Patent No.: US 10,734,586
App. No.: 15/447,704
Granted: Aug 4, 2020
Kind: B2

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Abstract

An organic light emitting device including an anode; a hole transport region on the anode; an emission layer on the hole transport region; an electron transport region on the emission layer; and a cathode on the electron transport region, wherein the hole transport region includes: a first hole transport layer including a first hole transport material represented by the following Formula 1 or a second hole transport material represented by the following Formula 2; and a second hole transport layer on the first hole transport layer, the second hole transport layer including a third hole transport material represented by the following Formula 3 or a fourth hole transport material represented by the following Formula 4:

Claims (94)

1. An organic light emitting device, comprising:

an anode;

a hole transport region on the anode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a cathode on the electron transport region,

wherein the hole transport region includes:

a first hole transport layer including a first hole transport material represented by the following Formula 1 or a second hole transport material represented by the following Formula 2; and

a second hole transport layer on the first hole transport layer, the second hole transport layer including a third hole transport material represented by the following Formula 3 or a fourth hole transport material represented by the following Formula 4:

wherein, in Formulae 1, 2, 3 and 4,

Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 8 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a deuterium atom, or a hydrogen atom,

Ar 6 and Ar 7 are each independently a substituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted aryl group having 10 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a deuterium atom, or a hydrogen atom, provided that, in Ar 6 and Ar 7 , a substituent of the substituted aryl group having 6 to 30 ring carbon atoms, the substituted heteroaryl group having 5 to 30 ring carbon atoms, the substituted alkyl group having 1 to 20 carbon atoms, and the substituted silyl group does not include an amino group, and provided that neither Ar 6 nor Ar 7 are a substituted fluorenyl group,

X is a direct linkage or CR 14 R 15 ,

R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a deuterium atom, or a hydrogen atom,

R 5 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, a deuterium atom, or a hydrogen atom, provided that, in R 5 , a substituent of the substituted aryl group having 6 to 30 ring carbon atoms, the substituted heteroaryl group having 5 to 30 ring carbon atoms, the substituted alkyl group having 1 to 20 carbon atoms, and the substituted silyl group does not include an amino group,

L 1 and L 2 are each independently a direct linkage, a substituted or unsubstituted alkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms,

a, b, and c are each independently an integer of 0 to 4,

d is an integer of 0 to 3, and

e is an integer of 0 to 5,

in the case where e is an integer of 2 to 5, adjacent ones of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are separate or are bound form a ring,

wherein the emission layer includes an emission material containing a donor and an acceptor, the emission material being a thermally activated delayed fluorescence material.

2. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the first hole transport material represented by Formula 1, and

Ar 1 and Ar 2 in Formula 1 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted acridine group.

3. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the first hole transport material represented by Formula 1, and

L 1 in Formula 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted fluorenylene group.

4. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the first hole transport material represented by Formula 1, and

the first hole transport material includes one of the following Compounds:

5. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the second hole transport material represented by Formula 2, and

Ar 3 and Ar 4 in Formula 2 are bound to form a ring.

6. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the second hole transport material represented by Formula 2, and

Ar 3 and Ar 4 in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted spirobifluorenyl group.

7. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the second hole transport material represented by Formula 2, and

Ar 5 in Formula 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted pyridine group.

8. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the second hole transport material represented by Formula 2, and

L 2 in Formula 2 is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted fluorenylene group.

9. The organic light emitting device as claimed in claim 1 , wherein:

the first hole transport layer includes the second hole transport material represented by Formula 2, and

the second hole transport material includes one of the following Compounds 2-1 to 2-20:

10. The organic light emitting device as claimed in claim 1 , wherein:

the second hole transport layer includes the third hole transport material represented by Formula 3,

Ar 6 and Ar 7 in Formula 3 are each independently a substituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, provided that, in Ar 6 and Ar 7 , a substituent of the substituted phenyl group, the substituted biphenyl group, the substituted naphthyl group, the substituted dibenzofuran group, and the substituted dibenzothiophene group does not include an amino group.

11. The organic light emitting device as claimed in claim 1 , wherein:

the second hole transport layer includes the third hole transport material represented by Formula 3,

e is an integer of 1 to 5, and

R 5 in Formula 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted benzo[def]carbazole group, provided that, in R 5 , a substituent of the substituted phenyl group, the substituted biphenyl group, the substituted naphthyl group, the substituted fluorenyl group, the substituted dibenzofuran group, and the substituted benzo[def]carbazole group does not include an amino group.

12. The organic light emitting device as claimed in claim 1 , wherein:

the second hole transport layer includes the third hole transport material represented by Formula 3, and

the third hole transport material includes one of the following Compounds 3-1 to 3-20:

13. The organic light emitting device as claimed in claim 1 , wherein: