Organic light-emitting device
Disclosed is an organic light-emitting device with high efficiency and long lifespan that uses an anthracene derivative having a characteristic structure as a host compound in a light-emitting layer of the organic light-emitting device and uses a compound having a characteristic structure as a compound for an electron transport layer.
1 . An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
a light-emitting layer interposed between the first electrode and the second electrode; and
an organic layer interposed between the second electrode and the light-emitting layer,
wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A] and the organic layer comprises at least one selected from compounds represented by the following [Formula B] to [Formula D],
the organic layer comprises an electron injection layer, an electron transport layer, or a layer capable of injecting and transporting electrons,
wherein L 1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L 1 are identical to or different from each other,
X is an oxygen atom (O) or a sulfur atom(S),
Ar 1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
R 1 to R 14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group, with the proviso that any one of Re to R 14 is bonded to the linker L 1 ,
wherein X 21 is a single bond, or O or S,
R 21 to R 24 are identical to or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group, and a halogen group, with the proviso that one or more of R 21 to R 24 are bonded to each other to further form a substituted or unsubstituted alicyclic or aromatic monocyclic or polycyclic ring, at least one carbon atom of which is substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur,
L 2 is a single bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,
Z 1 to Z 3 are each independently N or CR, with the proviso that at least one of Z 1 to Z 3 is N, wherein R's are identical to or different from each other, and are each independently hydrogen, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C2-C30 alkenyl group, or each R is bonded to Ar 21 or Ar 22 to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
Ar 21 and Ar 22 are identical to or different from each other, and are each independently hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, or are bonded to R to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
a 21 to a 23 are integers from 0 to 4, provided that when a 21 to a 23 are 2 or more, a plurality of R 21 to R 23 are identical to or different from each other, and
a 24 is an integer from 0 to 3, provided that when a 24 is 2 or more, a plurality of R 24 are identical to or different from each other,
wherein at least one of Z 4 to Z 6 is N and the remainder is CH, and at least one of Z 7 to Z 9 is N and the remainder is CH,
L 3 and L 4 are identical to or different from each other, and are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, and
Ar 31 to Ar 34 are identical to or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group,
wherein at least one of Z 10 to Z 12 is N and the remainder is CH,
L 5 and L 6 are identical to or different from each other, and are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, and
Ar 41 and Ar 42 are identical to or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group, and
n is 1 or 2,
wherein at least one of R 11 to R 14 in R is a substituted or unsubstituted C3-C20 cycloalkyl group.
2 . The organic light-emitting device according to claim 1 , wherein the compound of [Formula A] is represented by any one selected from the following compounds [Formula A-1] to [Formula A-6]:
wherein Ar 1 , R 1 to R 14 , L 1 , X and m are as defined in [Formula A] above.
3 . The organic light-emitting device according to claim 2 , wherein each of the compounds represented by [Formula A-1] to [Formula A-6] comprises at least one deuterium atom (D) as a substituent.
4 . The organic light-emitting device according to claim 2 , wherein each of the compounds represented by [Formula A-1] to [Formula A-6] has a degree of deuteration of 10% or more.
5 . The organic light-emitting device according to claim 1 , wherein the compound of [Formula B] is any one selected from the following compounds [B-1] to [B-196]:
6 . The organic light-emitting device according to claim 1 , wherein the compound of [Formula B] is any one selected from the following compounds [B-201] to [B-344]:
7 . The organic light-emitting device according to claim 1 , wherein the compound of [Formula C] is any one selected from the following compounds [C-1] to [C-60]:
8 . The organic light-emitting device according to claim 1 , wherein the compound of [Formula D] is any one selected from the following compounds [D-1] to [D-90]:
9 . The organic light-emitting device according to claim 1 , wherein the light-emitting layer comprises a host and a dopant, and
the compound represented by [Formula A] is used as the host.
10 . The organic light-emitting device according to claim 1 , wherein the organic light-emitting device is used for a display or lighting system selected from flat panel displays, flexible displays, monochromatic or white flat panel lighting systems, monochromatic or white flexible lighting systems, vehicle displays, and displays for virtual or augmented reality.
11 . An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
a light-emitting layer interposed between the first electrode and the second electrode; and
an organic layer interposed between the second electrode and the light-emitting layer,
wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A] and the organic layer comprises at least one selected from compounds represented by the following [Formula B],
the organic layer comprises an electron injection layer, an electron transport layer, or a layer capable of injecting and transporting electrons,
wherein L 1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L 1 are identical to or different from each other,
X is an oxygen atom (O) or a sulfur atom(S),
Ar 1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
R 1 to R 14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group, with the proviso that any one of R 9 to R 14 is bonded to the linker L 1 ,
wherein X 21 is a single bond,
R 21 to R 24 are identical to or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group, and a halogen group, with the proviso that one or more of R 21 to R 24 are bonded to each other to further form a substituted or unsubstituted alicyclic or aromatic monocyclic or polycyclic ring, at least one carbon atom of which is substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur,
L 2 is a single bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,
Z 1 to Z 3 are each independently N or CR, with the proviso that at least one of Z 1 to Z 3 is N, wherein R's are identical to or different from each other, and are each independently hydrogen, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C2-C30 alkenyl group, or each R is bonded to Ar 21 or Ar 22 to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
Ar 21 and Ar 22 are identical to or different from each other, and are each independently hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, or are bonded to R to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
a 21 to a 23 are integers from 0 to 4, provided that when a 21 to a 23 are 2 or more, a plurality of R 21 to R 23 are identical to or different from each other, and
a 24 is an integer from 0 to 3, provided that when a 24 is 2 or more, a plurality of R 24 are identical to or different from each other.
12 . The organic light-emitting device according to claim 11 , wherein the compound of [Formula A] is represented by any one selected from the following compounds [Formula A-1] to [Formula A-6]:
wherein Ar 1 , R 1 to R 14 , L 1 , X and m are as defined in [Formula A] above.
13 . The organic light-emitting device according to claim 12 , wherein each of the compounds represented by [Formula A-1] to [Formula A-6] has a degree of deuteration of 10% or more.
14 . The organic light-emitting device according to claim 12 , wherein at least one of R 11 to R 14 in each of the compounds represented by [Formula A-1] to [Formula A-6] is selected from a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 cycloalkyl group, and a substituted or unsubstituted C3-C20 heteroaryl group.
15 . The organic light-emitting device according to claim 11 , wherein the compound of [Formula A] is any one selected from the following compounds [A-1] to [A-218]:
16 . An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
a light-emitting layer interposed between the first electrode and the second electrode; and
an organic layer interposed between the second electrode and the light-emitting layer,
wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A] and the organic layer comprises at least one selected from compounds represented by the following [Formula C] or [Formula D],
the organic layer comprises an electron injection layer, an electron transport layer, or a layer capable of injecting and transporting electrons,
wherein L 1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L 1 are identical to or different from each other,
X is an oxygen atom (O) or a sulfur atom(S),
Ar 1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
R 1 to R 14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group, with the proviso that any one of R 9 to R 14 is bonded to the linker L 1 ,
wherein at least one of Z 4 to Z 6 is N and the remainder is CH, and at least one of Z 7 to Z 9 is N and the remainder is CH,
L 3 and L 4 are identical to or different from each other, and are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, where at least one of L 3 and L 4 is a substituted or unsubstituted C2-C30 heteroarylene group, and
Ar 31 to Ar 34 are identical to or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group,
wherein at least one of Z 10 to Z 12 is N and the remainder is CH,
L 5 and L 6 are identical to or different from each other, and are each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, where at least one of L 5 and L 6 is a substituted or unsubstituted C2-C30 heteroarylene group, and
Ar 41 and Ar 42 are identical to or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group, and
n is 1 or 2.
17 . The organic light-emitting device according to claim 16 , wherein the compound of [Formula A] is represented by any one selected from the following compounds [Formula A-1] to [Formula A-6]:
wherein Ar 1 , R 1 to R 14 , L 1 , X and m are as defined in [Formula A] above.
18 . The organic light-emitting device according to claim 17 , wherein each of the compounds represented by [Formula A-1] to [Formula A-6] comprises at least one deuterium atom (D) as a substituent.
19 . The organic light-emitting device according to claim 17 , wherein each of the compounds represented by [Formula A-1] to [Formula A-6] has a degree of deuteration of 10% or more.
20 . The organic light-emitting device according to claim 16 , wherein the compound of [Formula A] is any one selected from the following compounds [A-1] to [A-218]: