Organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsMikyung Kim, Jihyun Seo, Seunggak Yang, Kwanhee Lee, Jino Lim
Life of this patent
Estimating the term…
Abstract
An organic light-emitting device is provided. The organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, the organic layer including a first compound, a second compound, and a third compound. The first compound, the second compound, and the third compound are each independently an azine-based compound represented by one selected from Formulae 1-1 to 1-5, except for a case where the first compound, the second compound, and the third compound concurrently include an azine-based compound represented by Formula 1-3.
Claims20
An organic light-emitting device comprising:
- a first electrode;
- a second electrode;
- and
- an organic layer between the first electrode and the second electrode and comprising an emission layer,
- wherein the organic layer comprises a first compound, a second compound, and a third compound, and
- the first compound, the second compound, and the third compound are each independently an azine-based compound represented by one selected from Formulae 1-1 to 1-5, except for a case where the first compound, the second compound, and the third compound concurrently include an azine-based compound represented by Formula 1-3:
- wherein, in Formulae 1-1 to 1-5,
- X11a is selected from N and C[(L11a)a11a-R11a];
- X11b is selected from N and C[(L11b)a11b-R11b];
- X11c is selected from N and C[(L11c)a11c-R11c];
- X11d is selected from N and C[(L11d)a11d-R11d];
- X11e is selected from N and C[(L11e)a11e-R11e];
- X11f is selected from N and C[(L11f)a11f-R11f];
- and one of X11a to X11f is N,
- X12a is selected from N and C[(L12a)a12a-R12a];
- X12b is selected from N and C[(L12b)a12b-R12b];
- X12c is selected from N and C[(L12c)a12c-R12c];
- X12d is selected from N and C[(L12d)a12d-R12d];
- X12e is selected from N and C[(L12e)a12e-R12e];
- X12f is selected from N and C[(L12f)a12f-R12f];
- and two of X12a to X12f are N,
- X13a is selected from N and C[(L13a)a13a-R13a];
- X13b is selected from N and C[(L13b)a13b-R13b];
- X13c is selected from N and C[(L13c)a13c-R13c];
- X13d is selected from N and C[(L13d)a13d-R13d];
- X13e is selected from N and C[(L13e)a13e-R13e];
- X13f is selected from N and C[(L13f)a13f-R13f];
- and three of X13a to X13f are N,
- X14a is selected from N and C[(L14a)a14a-R14a];
- X14b is selected from N and C[(L14b)a14b-R14b];
- X14c is selected from N and C[(L14c)a14c-R14c];
- X14d is selected from N and C[(L14d)a14d-R14d];
- X14e is selected from N and C[(L14e)a14e-R14e];
- X14f is selected from N and C[(L14f)a14f-R14f];
- and four of X14a to X14f are N,
- X15a is selected from N and C[(L15a)a15a-R15a];
- X15b is selected from N and C[(L15b)a15b-R15b];
- X15c is selected from N and C[(L15c)a15c-R15c];
- X15d is selected from N and C[(L15d)a15d-R15d];
- X15e is selected from N and C[(L15e)a15e-R15e];
- X15f is selected from N and C[(L15f)a15f-R15f];
- and five of X15a to X15f are N,
- L11a to L11f, L12a to L12f, L13a to L13f, L14a to L14f, and L15a to L15f are each independently selected from:
- a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group;
- and
- a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C6-C30 arylthio group, a C1-C30 heteroaryloxy group, a C1-C30 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group, wherein L11a to L11f, L12a to L12f, L13a to L13f, L14a to L14f, and L15a to L15f are not each independently selected from:
- a triazinylene group;
- and a triazinylene group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C6-C30 arylthio group, a C1-C30 heteroaryloxy group, a C1-C30 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group,
- a11a to a11f, a12a to a12f, a13a to a13f, a14a to a14f, and a15a to a15f are each independently selected from 0, 1, 2, 3, and 4,
- R11a to R11f, R12a to R12f, R13a to R13f, R14a to R14f, and R15a to R15f are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group;
- a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I;
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, and a benzothienopyrimidinyl group;
- and
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, and a benzothienopyrimidinyl group that are each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I, and
- neighboring atoms of R11a to R11f, neighboring atoms of R12a to R12f, neighboring atoms of R13a to R13f, neighboring atoms of R14a to R14f, and/or neighboring atoms of R15a to R15f optionally form a saturated ring or an unsaturated ring.
An organic light-emitting device comprising:
- a substrate divided into a first sub-pixel region, a second sub-pixel region, and a third sub-pixel region;
- a plurality of first electrodes respectively arranged in the first sub-pixel region, the second sub-pixel region, and the third sub-pixel region of the substrate;
- a second electrode facing the plurality of first electrodes;
- and
- an organic layer between the plurality of first electrodes and the second electrode and comprising an emission layer,
- wherein the organic layer comprises a first compound, a second compound, and a third compound, and
- the first compound, the second compound, and the third compound are each independently an azine-based compound represented by one selected from Formulae 1-1 to 1-5, except for a case where the first compound, the second compound, and the third compound concurrently include an azine-based compound represented by Formula 1-3:
- wherein, in Formulae 1-1 to 1-5,
- X11a is selected from N and C[(L11a)a11a-R11a];
- X11b is selected from N and C[(L11b)a11b-R11b];
- X1 is selected from N and C[(L11c)a11c-R11c];
- X11d is selected from N and C[(L11d)a11d-R11d];
- X11e is selected from N and C[(L11e)a11e-R11e];
- X11f is selected from N and C[(L11f)a11f-R11f];
- and one of X11a to X11f is N,
- X12a is selected from N and C[(L12a)a12a-R12a];
- X12b is selected from N and C[(L12b)a12b-R12b];
- X12c is selected from N and C[(L12c)a12c-R12c];
- X12d is selected from N and C[(L12d)a12d-R12d];
- X12e is selected from N and C[(L12e)a12e-R12e];
- X12f is selected from N and C[(L12f)a12f-R12f];
- and two of X12a to X12f are each N,
- X13a is selected from N and C[(L13a)a13a-R13a];
- X13b is selected from N and C[(L13b)a13b-R13b];
- X13c is selected from N and C[(L13c)a13c-R13c];
- X13d is selected from N and C[(L13d)a13d-R13d];
- X13e is selected from N and C[(L13e)a13e-R13e];
- X13f is selected from N and C[(L13f)a13f-R13f];
- and three of X13a to X13f are each N,
- X14a is selected from N and C[(L14a)a14a-R14a];
- X14b is selected from N and C[(L14b)a14b-R14b];
- X14c is selected from N and C[(L14c)a14c-R14c];
- X14d is selected from N and C[(L14d)a14d-R14d];
- X14e is selected from N and C[(L14e)a14e-R14e];
- X14f is selected from N and C[(L14f)a14f-R14f];
- and four of X14a to X14f are each N,
- X15a is selected from N and C[(L15a)a5a-R15a];
- X15b is selected from N and C[(L15b)a15b-R15b];
- X15e is selected from N and C[(L15c)a15c-R15c];
- X15d is selected from N and C[(L15d)a15d-R15d];
- X15e is selected from N and C[(L15e)a15e-R15e];
- X15f is selected from N and C[(L15f)a15f-R15f];
- and five of X15a to X15f are each N,
- L11a to L11f, L12a to L12f, L13a to L13f, L14a to L14f, and L15a to L15f are each independently selected from:
- a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group;
- and
- a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C6-C30 arylthio group, a C1-C30 heteroaryloxy group, a C1-C30 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group, wherein L11a to L11f, L12a to L12f, L13a to L13f, L14a to L14f, and L15a to L15f are not each independently selected from:
- a triazinylene group;
- and a triazinylene group substituted with at least one selected from:
- deuterium, —F, —Cl, —Br, —I, 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C6-C30 arylthio group, a C1-C30 heteroaryloxy group, a C1-C30 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group,
- a11a to a11f, a12a to a12f, a13a to a13f, a14a to a14f, and a15a to a15f are each independently selected from 0, 1, 2, 3, and 4,
- R11a to R11f, R12a to R12f, R13a to R13f, R14a to R14f, and R15a to R15f are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group;
- a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I;
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, and a benzothienopyrimidinyl group;
- and
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a benzofuropyrimidinyl group, and a benzothienopyrimidinyl group that are each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I, and
- neighboring atoms of R11a to R11f, neighboring atoms of R12a to R12f, neighboring R13a to R13f, neighboring atoms of R14a to R14f, and/or neighboring atoms of R15a to R15f optionally form a saturated ring or an unsaturated ring.
Dependencies are inferred from the claim text.