	US 11,230,521 C1 (13,310th)
	Monoamine compound and organic electroluminescence device including the same
Ichinori Takada, Yokohama (JP); Takuya Uno, Yokohama (JP); and Xiulan Jin, Yokohama (JP)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Assigned to MASSIVELY BROADBAND LLC, Austin, TX (US)
Reexamination Request No. 90/015,512, Sep. 12, 2025.
Reexamination Certificate for Patent 11,230,521, issued Jan. 25, 2022, Appl. No. 15/921,936, Mar. 15, 2018.
Ex Parte Reexamination Certificate issued on Aug. 4, 2026.
Int. Cl. C07C 211/54 (2006.01); C07D 307/91 (2006.01); C07D 333/76 (2006.01); C07F 7/08 (2006.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)

CPC C07C 211/54 (2013.01) [C07D 307/91 (2013.01); C07D 333/76 (2013.01); C07F 7/0805 (2013.01); C09K 11/06 (2013.01); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 85/40 (2023.02); H10K 85/631 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C07C 2603/26 (2017.05); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/1092 (2013.01)]

AS A RESULT OF REEXAMINATION, IT HAS BEEN DETERMINED THAT:

Claims 1-3, 10-12, 15, 16, and 19-20 are determined to be patentable as amended.

Claims 4-9, 13, 14, 17 and 18, dependent on an amended claim, are determined to be patentable.

1. A monoamine compound represented by the following Formula 1:

wherein, in Formula 1,

Ar¹is a group represented by the following Formula 2,

Ar²and Ar³are each independently a group represented by the following Formula 2, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, 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,

[ L¹is a direct linkage,]

~~L¹to~~ [ L²and ] L³are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,

wherein, in Formula 2,

R¹to R⁴are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted arylthio group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms,

R¹to R⁴are separate or form a ring by combining adjacent groups with each other,

I is 0 or 1,

m, n, and o are each independently an integer of 0 to 4, and

p is an integer of 0 to 5,

wherein at least one selected from Ar¹, Ar²and Ar³is different from at least an other one selected from Ar¹, Ar²and Ar³, and

wherein when ~~L¹to~~ [ L²and ] L³are each independently a direct linkage, and one selected from Ar²and Ar³is a group represented by Ar-18, an other one selected from Ar²and Ar³is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group derived from an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or the group represented by Ar-18,

wherein in Ar-18, * is a bonding location,

wherein in Ar¹represented by Formula 2, when R¹to R⁴are each a hydrogen atom, I is 1,

[ wherein, in Ar¹represented by Formula 2, when I is 0, at least one of L²-Ar²or L³-Ar³comprises a fused ring structure including two or more directly fused benzene rings,

wherein when L²-Ar²and L³-Ar³are each a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R¹excludes a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, ] and

wherein the monoamine compound represented by Formula 1 is a single amine group compound.

2. The monoamine compound as claimed in claim 1, wherein the compound represented [ by ] Formula 1 is represented by the following Formula 1-1, 1-2 or 1-6:

wherein, in Formulae 1-1, 1-2 and 1-6, Ar², Ar³, L¹to L³, R¹to R⁴, and I to p are defined the same as those of Formula 1.

3. The monoamine compound as claimed in claim 1, wherein the compound represented [ by ] Formula 1 is represented by one of the following Formulae 1-3 to 1-5:

wherein, in Formulae 1-3 to 1-5, Ar², Ar³, L¹to L³, R¹to R⁴, and I to p are defined the same as those of Formula 1.

10. The monoamine compound as claimed in claim 1, wherein ~~L¹to~~ [ L²and ] L³are each independently a direct linkage or a substituted or unsubstituted phenylene group.

11. A compound of the following Compound Group 1:

12. An organic electroluminescence device, comprising:

a first electrode;

an organic layer on the first electrode, the organic layer including a hole transport region, an emission layer, and an electron transport region; and

a second electrode on the organic layer,

wherein the organic layer includes a monoamine compound represented by the following Formula 1:

wherein, in Formula 1,

Ar¹is a group represented by the following Formula 2,

Ar²and Ar³are each independently a group represented by the following Formula 2, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, 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,

[ L¹is a direct linkage,]

wherein, in Formula 2,

R¹to R⁴are separate or form a ring by combining adjacent groups with each other, I is 0 or 1,

m, n, and o are each independently an integer of 0 to 4, and

p is an integer of 0 to 5,

wherein at least one selected from Ar¹, Ar²and Ar³is different from at least an other one selected from Ar¹, Ar²and Ar³, and

wherein when ~~L¹to~~ [ L^{2 and}] L³are each independently a direct linkage, and one selected from Ar²and Ar³is a group represented by Ar-18, an other one selected from Ar²and Ar³is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group derived from an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or the group represented by Ar-18,

wherein in Ar-18, * is a bonding location,

wherein in Ar¹represented by Formula 2, when R¹to R⁴are each a hydrogen atom, I is 1,

[ wherein, in Ar¹represented by Formula 2, when I is 0, at least one of L²-Ar²or L³-Ar³comprises a fused ring structure including two or more directly fused benzene rings,

wherein the monoamine compound represented by Formula 1 is a single amine group compound.

15. The organic electroluminescence device as claimed in claim 12, wherein the compound represented by Formula 1 is represented by the following Formula 1-1, 1-2 or 1-6:

wherein, in Formulae 1-1, 1-2 and 1-6, Ar², Ar³, L¹to L³, R¹to R⁴, and I to p are defined the same as those of Formula 1.

16. The organic electroluminescence device as claimed in claim 12, wherein the compound represented [ by ] Formula 1 is represented by one of the following Formulae 1-3 to 1-5:

wherein, in Formulae 1-3 to 1-5, Ar², Ar³, L¹to L³, R¹to R⁴, and I to p are defined the same as those of Formula 1.

19. The organic electroluminescence device as claimed in claim 12, wherein ~~L¹to~~ [ L²and ] L³are each independently a direct linkage or a substituted or unsubstituted phenylene group.

20. An organic electroluminescence device, comprising:

a first electrode;

an organic layer on the first electrode, the organic layer including a hole transport region, an emission layer, and an electron transport region; and

a second electrode on the organic layer, wherein the organic layer includes a monoamine compound, the hole transport region includes the monoamine compound, and the monoamine compound is a compound of the following Compound Group 1: