Luminescence device and nitrogen-containing compound for same
A luminescence device, includes: a first electrode; a hole transport region disposed on the first electrode; an emission layer disposed on the hole transport region; an electron transport region disposed on the emission layer; and a second electrode disposed on the electron transport region, wherein the hole transport region includes a compound of Formula 1: in Formula 1, the variables are described herein.
1 . A luminescence device, comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region,
wherein the hole transport region comprises a nitrogen-containing compound represented by Formula 1:
in Formula 1,
X is O, S, or NR 5 ,
R 1 is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group,
R 2 to R 5 are each, independently from one another, a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
a is an integer of 1 to 4,
b and c are each, independently from one another, an integer of 0 to 4,
d is an integer of 0 to 3, and
hydrogen is optionally replaced with deuterium.
2 . The luminescence device of claim 1 , wherein the hole transport region comprises:
a hole injection layer disposed on the first electrode; and
a hole transport layer disposed on the hole injection layer, and
the nitrogen-containing compound of Formula 1 is comprised in at least one of the hole injection layer or the hole transport layer.
3 . The luminescence device of claim 2 , further comprising an electron blocking layer disposed on the hole transport layer.
4 . The luminescence device of claim 1 , wherein the Formula 1 is represented by Formula 2:
in Formula 2,
a′ and b′ are each, independently from one another, an integer of 0 to 3,
R a is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group,
R b is a hydrogen atom, a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
X, R 1 to R 4 , c, and d have, independently from one another, the same meaning as defined in the Formula 1 in claim 1 .
5 . The luminescence device of claim 1 , wherein the Formula 1 is represented by Formula 3:
in Formula 3,
a′ and b′ are each, independently from one another, an integer of 0 to 3,
R a is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group,
R b is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
X, R 1 to R 4 , c, and d have, independently from one another, the same meaning as defined in the Formula 1 in claim 1 .
6 . The luminescence device of claim 4 , wherein the Formula 2 is represented by Formula 4:
in Formula 4,
R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 4 .
7 . The luminescence device of claim 4 , wherein the Formula 2 is represented by Formula 5:
in Formula 5,
R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 4 .
8 . The luminescence device of claim 4 , wherein the Formula 2 is represented by Formula 6:
in Formula 6,
R 5 is a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 4 .
9 . The luminescence device of claim 4 , wherein the Formula 2 is represented by Formula 7-1 or Formula 7-2:
in Formula 7-1 and Formula 7-2,
X, R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 4 .
10 . The luminescence device of claim 4 , wherein R a is a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group, and
R b is a hydrogen atom, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.
11 . The luminescence device of claim 1 , wherein the nitrogen-containing compound of the Formula 1 is at least one of the compounds in Compound Group 1:
12 . The luminescence device of claim 1 , wherein the nitrogen-containing compound of the Formula 1 is at least one compound of the Compound Group 2:
13 . The luminescence device of claim 1 , wherein the nitrogen-containing compound of the Formula 1 is at least one compound of Compound Group 3:
14 . A nitrogen-containing compound represented by Formula 1:
in Formula 1,
X is O, S, or NR 5 ,
R 1 is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group,
R 2 to R 5 are each, independently from one another, a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
a is an integer of 1 to 4,
b and c are each, independently from one another, an integer of 0 to 4,
d is an integer of 0 to 3, and
hydrogen is optionally replaced with deuterium.
15 . The nitrogen-containing compound of claim 14 , wherein the Formula 1 is represented by Formula 2:
in Formula 2,
a′ and b′ are each, independently from one another, an integer of 0 to 3,
R a is a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, a substituted or an unsubstituted dibenzofuran group, a substituted or an unsubstituted dibenzothiophene group, or a substituted or an unsubstituted carbazole group,
R b is a hydrogen atom, a substituted or an unsubstituted oxy group, a substituted or an unsubstituted silyl group, a substituted or an unsubstituted thiol group, a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted alkenyl group of 2 to carbon atoms, a substituted or an unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
X, R 1 to R 4 , c, and d have, independently from one another, the same meaning as defined in the Formula 1 in claim 14 .
16 . The nitrogen-containing compound of claim 15 , wherein the Formula 2 is represented by any one of Formula 4 to Formula 6:
in Formula 4 to Formula 6,
R 5 is a substituted or an unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or an unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or an unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 15 .
17 . The nitrogen-containing compound of claim 15 , wherein the Formula 2 is represented by Formula 7-1 or Formula 7-2:
in Formula 7-1 and Formula 7-2,
X, R 1 to R 4 , R a , R b , c, d, a′ and b′ have, independently from one another, the same meaning as defined in the Formula 2 in claim 15 .
18 . A nitrogen-containing compound is selected from the compounds in Compound Group 1, the compounds in Compound Group 2, and the compounds in Compound Group 3: