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US 12,615,960 B2Granted
Organic light-emitting device
AssigneeSfc Co., Ltd.
InventorsJin-hwi Cho, Se-jin Yu, So-young Shim, Yong-woon Yang
Life of this patent
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Abstract
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.
Claims20
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 L1 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 L1 are identical to or different from each other,
- X is an oxygen atom (O) or a sulfur atom(S),
- Ar1 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,
- R1 to R14 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 R14 is bonded to the linker L1,
- wherein X21 is a single bond, or O or S,
- R21 to R24 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 R21 to R24 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,
- L2 is a single bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,
- Z1 to Z3 are each independently N or CR, with the proviso that at least one of Z1 to Z3 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 Ar21 or Ar22 to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
- Ar21 and Ar22 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,
- a21 to a23 are integers from 0 to 4, provided that when a21 to a23 are 2 or more, a plurality of R21 to R23 are identical to or different from each other, and
- a24 is an integer from 0 to 3, provided that when a24 is 2 or more, a plurality of R24 are identical to or different from each other,
- wherein at least one of Z4 to Z6 is N and the remainder is CH, and at least one of Z7 to Z9 is N and the remainder is CH,
- L3 and L4 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
- Ar31 to Ar34 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 Z10 to Z12 is N and the remainder is CH,
- L5 and L6 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
- Ar41 and Ar42 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 R11 to R14 in R is a substituted or unsubstituted C3-C20 cycloalkyl group.
24 more elements
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 L1 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 L1 are identical to or different from each other,
- X is an oxygen atom (O) or a sulfur atom(S),
- Ar1 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,
- R1 to R14 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 R9 to R14 is bonded to the linker L1,
- wherein X21 is a single bond,
- R21 to R24 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 R21 to R24 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,
- L2 is a single bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,
- Z1 to Z3 are each independently N or CR, with the proviso that at least one of Z1 to Z3 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 Ar21 or Ar22 to form a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted aromatic heterocycle,
- Ar21 and Ar22 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,
- a21 to a23 are integers from 0 to 4, provided that when a21 to a23 are 2 or more, a plurality of R21 to R23 are identical to or different from each other, and
- a24 is an integer from 0 to 3, provided that when a24 is 2 or more, a plurality of R24 are identical to or different from each other.
16 more elements
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 L1 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 L1 are identical to or different from each other,
- X is an oxygen atom (O) or a sulfur atom(S),
- Ar1 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,
- R1 to R14 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 R9 to R14 is bonded to the linker L1,
- wherein at least one of Z4 to Z6 is N and the remainder is CH, and at least one of Z7 to Z9 is N and the remainder is CH,
- L3 and L4 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 L3 and L4 is a substituted or unsubstituted C2-C30 heteroarylene group, and
- Ar31 to Ar34 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 Z10 to Z12 is N and the remainder is CH,
- L5 and L6 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 L5 and L6 is a substituted or unsubstituted C2-C30 heteroarylene group, and
- Ar41 and Ar42 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.
16 more elements
Dependencies are inferred from the claim text.