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US 9,960,359 B2Granted
Arylamine-based compound and organic light emitting diode comprising the same
AssigneeSamsung Display Co., Ltd.
InventorsSeok-Hwan Hwang, Young-Kook Kim, Hye-Jin Jung, Jun-Ha Park, Eun-Young Lee, Jin-O Lim, Sang-Hyun Han, Eun-Jae Jeong, Soo-Yon Kim, Jong-Hyuk Lee
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Abstract
An arylamine-based compound is represented by Formula 1 below. The arylamine-based compound is included in an organic light emitting diode.
Claims14
An arylamine-based compound represented by Formula 1 below:
- wherein in Formula 1,
- ring A is selected from:
- benzene, naphthalene, anthracene, fluorene, spiro-fluorene, phenanthrene, triphenylene, chrysene, naphthacene, perylene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, quinoline, isoquinoline, benzoquinoline, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, or benzocarbazole;
- (X)n is selected from Formulae 3a to 3n below:
- wherein in Formulae 3a to 3n, * is a binding site to the nitrogen atom of a pyrrole ring in Formula 1 and *′ is a binding site to the other nitrogen atom;
- each of Ar1 and Ar2 is independently selected from:
- a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group;
- each of R1, and R2 is independently selected from:
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;
- each of R3 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or an unsubstituted C2-C30 heteroaryl group;
- and
- a is an integer of 0 to 4.
9 more elements
An organic light emitting diode comprising:
- a first electrode;
- a second electrode facing the first electrode;
- and an organic layer between the first electrode and the second electrode, and comprising an emission layer;
- wherein the organic layer comprises a hole transporting layer between the first electrode and the emission layer;
- wherein the hole transporting layer between the first electrode and the emission layer comprises a first hole transporting layer and a second hole transporting layer, wherein the second hole transporting layer is between the first hole transporting layer and the emission layer, and the second hole transporting layer comprises the arylamine-based compound of Formula 1.
2 more elements
An organic light emitting diode comprising:
- a first electrode;
- a second electrode facing the first electrode;
- and
- an organic layer between the first electrode and the second electrode, and comprising an emission layer,
- wherein the organic layer comprises an arylamine-based compound represented by Formula 1 below,
- Formula 1
- wherein in Formula 1,
- ring A is selected from:
- a C6-C20 aromatic ring or a C2-C20 heteroaromatic ring;
- each X is independently selected from:
- a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, and two or more Xs are optionally connected to each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring;
- n is an integer of 1 to 5;
- each of Ar1 and Ar2 is independently selected from:
- a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group;
- each of R1, R2 and each of R3 is independently selected from:
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;
- and
- a is an integer of 0 to 4,
- wherein the organic layer comprises:
- a hole transporting region between the first electrode and the emission layer, the hole transporting region further comprising at least one of:
- a hole injecting layer, a hole transporting layer, a functional layer having both hole injecting and hole transporting capabilities, a buffer layer, or an electron blocking layer, and
- an electron transporting region between the emission layer and the second electrode, the electron transporting region further comprising at least one of:
- a hole blocking layer, an electron transporting layer, or an electron injecting layer,
- wherein the hole transporting layer comprises a first hole transporting layer and a second hole transporting layer,
- wherein the second hole transporting layer is between the first hole transporting layer and the emission layer, and
- the second hole transporting layer comprises the arylamine-based compound of Formula 1.
23 more elements
An arylamine-based compound represented by Formula 1 below:
- Formula 1
- wherein in Formula 1,
- ring A is selected from:
- benzene, naphthalene, anthracene, fluorene, spiro-fluorene, phenanthrene, triphenylene, chrysene, naphthacene, perylene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, quinoline, isoquinoline, benzoquinoline, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, or benzocarbazole;
- each X is independently selected from:
- a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group, and two or more Xs are optionally connected to each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring;
- n is an integer of 1 to 5;
- each of Ar1 and Ar2 is independently any one of Formulae 4a to 4s:
- wherein in Formulae 4a to 4s,
- is a binding site to the nitrogen atom;
- each of Ar1 and Ar2 is independently selected from:
- a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroaryl group;
- each of R1, and R2 is independently selected from:
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;
- each of R3 is independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, or an unsubstituted C2-C30 heteroaryl group;
- and
- a is an integer of 0 to 4.
14 more elements
Dependencies are inferred from the claim text.