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US 10,651,402 B2Granted
Organometallic compound and organic light-emitting device including the same
AssigneeSamsung Electronics Co., Ltd.
InventorsKum Hee Lee, Kyuyoung Hwang, Yoonhyun Kwak, Ohyun Kwon, Aram Jeon, Hyeonho Choi, Byoungki Choi
Life of this patent
Estimating the term…
Abstract
An organometallic compound represented by Formula 1: wherein, in Formula 1, b18, A11, L11, M, m, R18, and X11 to X17 are the same as described in the specification.
Claims18
An organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal;
- A11 is selected from a C3-C14 heterocyclic group condensed with a 6-membered ring group and a C3-C14 heterocyclic group condensed with a 5-membered ring group,
- the C3-C14 heterocyclic group is selected from a pyrrole group, a pyrazole group, an imidazole group, a thiazole group, an isothiazole group, an oxazole group, an iso-oxazole group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a thiazine group, an oxazine group, a quinoline group, an isoquinoline group, a cinnoline group, a quinazoline group, a quinoxaline group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 1,8-naphthyridine group, a phthalazine group, 2,6-naphthyridine group, and 2,7-naphthyridine group, the 6-membered ring group is selected from a benzene group, a cyclohexane group, a cyclohexene group, a pyridine group, a piperidine group, a pyrazine group, a hexahydropyrimidine group, a tetrahydropyrazine group, and a piperazine group, and the 5-membered ring group is selected from a cyclopentene group, a cyclopentadiene group, a dihydropyrrole group, a pyrrole group, an imidazole group, and a pyrrolidine group;
- X11 is N, X12 is CR12, X13 is CR13, X14 is CR14, X15 is CR15, X16 is CR16, and X17 is CR17;
- X11 is CR11, X12 is N, X13 is CR13, X14 is CR14, X15 is CR15, X16 is CR16, and X17 is CR17;
- X11 is CR11, X12 is CR12, X13 is N, X14 is CR14, X15 is CR15, X16 is CR16, and X17 is CR17;
- X11 is CR11, X12 is CR12, X13 is CR13, X14 is N, X15 is CR15, X16 is CR16, and X17 is CR17;
- X11 is CR11, X12 is CR12, X13 is CR13, X14 is CR14, X15 is N, X16 is CR16, and X17 is CR17;
- X11 is CR11, X12 is CR12, X13 is CR13, X14 is CR14, X15 is CR15, X16 is N, and X17 is CR17;
- X11 is CR11, X12 is CR12, X13 is CR13, X14 is CR14, X15 is CR15, X16 is CR16, and X17 is N;
- or
- X11 is CR11, X12 is CR12, X13 is CR13, X14 is CR14, X15 is CR15, X16 is CR16, and X17 is CR17;
- R11 to R18 are each independently selected from a hydrogen, 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q1), —N(Q1)(Q2), and —Si(Q1)(Q2)(Q3), wherein at least two adjacent groups of R11 to R17 are optionally linked to each other to form a saturated or unsaturated ring;
- Q1 to Q3 are each independently selected from a hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C60 aryl group;
- b18 is selected from 1, 2, 3, 4, 5, 6, 7, and 8;
- n is 1, 2, 3, and 4;
- L11 is selected from a monodentate ligand or a bidentate ligand selected from the group consisting of an oxalate, an acetylacetonate, a picolinic acid, a 2-(2-hydroxyphenyl)-pyridine, 2-phenylpyridine, a 1,2-bis(diphenylphosphino)ethane, a 1,1-bis(diphenylphosphino)methane, a glycinate, an ethylenediamine, a 2,2′-bipyridine, a 1,10-phenanthroline and ligands represented by Formulae 2-1 to 2-3;
- wherein, in Formulae 2-1 to 2-3,
- A21 is selected from a C5-C20 carbocyclic group and a C1-C20 heterocyclic group;
- X21 and X22 are each independently selected from C and N;
- Y21 is selected from a single bond, a double bond, a substituted or unsubstituted C1-C5 alkylene group, a substituted or unsubstituted C2-C5 alkenylene group, and a substituted or unsubstituted C6-C10 arylene group;
- Z21 and Z22 are each independently selected from N, O, N(R25), P(R25)(R26), and As(R25)(R26);
- R21 to R26 are each independently selected from a hydrogen, 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, and a C1-C20 alkoxy group,
- a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of 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 phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,
- a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl 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 triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, and
- a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl 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 triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl 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 triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group;
- b21 is selected from 1, 2, and 3;
- and
- * and *′ are each independently a binding site with an adjacent atom;
- and
- m is selected from 0, 1, 2, 3, 4, 5, and 6.
29 more elements
Dependencies are inferred from the claim text.