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US 12,721,036 B2Granted
Organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsHwan-Hee Cho, Myeong-Suk Kim, Jae-Yong Lee, Hye-In Jeong
Life of this patent
Estimating the term…
Abstract
An organic light-emitting device is provided. The device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer. The organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2. Various possibilities for the constituents of chemical structures in Formulas 1 and 2 are presented.
Claims3
An organic light-emitting device comprising:
- a first electrode;
- a second electrode;
- and
- an organic layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein
- the emission layer comprises:
- a first compound that is selected from Compounds A-108, A-114 to A-116, A-119, A-120, A-123 to A-128, A-130, A-131, A-146, A-151 to A-184, A-190 to A-205, or A-210 to A-215;
- and
- a second compound represented by Formula 2:
- wherein, in Formulae 2 and 9,
- L21 to L23 are each independently selected from:
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, and or a C1-C60 heteroarylene group;
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, and or a C1-C60 heteroarylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a group represented by Formula 9, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), or —B(Q31)(Q32);
- or
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, or a C1-C60 heteroarylene group, each substituted with at least one selected from a C6-C60 aryl group or a C1-C60 heteroaryl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a group represented by Formula 9, —N(Q21)(Q22), —Si(Q21)(Q22)(Q23), or —B(Q21)(Q22),
- a21 to a23 are each independently selected from 1, 2, 3, 4 or 5,
- R21 to R23 are RHT,
- R24 to R26 are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
- and/or
- a C6-C60 aryl group, substituted with at least one selected from a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, or a group represented by Formula 9,
- n21 to n23 are each independently selected from 0, 1 or 2,
- the sum of n21, n22, and n23 is selected from 1, 2, 3, 4, 5 or 6,
- RHT is selected from:
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, a benzothiophenyl group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), or —B(Q1)(Q2);
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, or a benzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a group represented by Formula 9, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or —B(Q31)(Q32);
- or
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, or a benzothiophenyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a group represented by Formula 9, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), or —B(Q21)(Q22),
- X91 is selected from a single bond, O, S, C(R93)(R94), B(R93), P(R93), or P(R93)(R94)
- X92 is selected from O, S, C(R95)(R96), B(R95), P(R95), or P(R95)(R96),
- provided that, when RHT is a group represented by Formula 9 and one of X91 or X92 is S, the rest of X91 or X92 is neither O nor S, A91 and A92 are each independently selected from a benzene group, a naphthalene group, an anthracene group, or a phenanthrene group,
- R91 to R96 are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or —B(Q31)(Q32);
- or
- a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), or —B(Q21)(Q22),
- b91 is selected from 1, 2, 3, 4 or 5,
- b92 is selected from 1, 2, 3, 4, 5 or 6, and
- Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group.
34 more elements
An organic light-emitting device comprising:
- a first electrode;
- a second electrode;
- and
- an organic layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein
- the emission layer comprises:
- a first compound represented by Formula 1;
- and
- a second compound that is selected from Compounds B-101, B-112 to B-113, B-124, B-125, B-127 to B-164, B-167, B-168, B-173, B-178 to B-180, B-183, B-186, B-189, B-193, B-195, B-200, B-204, B-205, B-208, B-212, B-213, B-218, B-219, B-222, B-227, B-228, or B-233:
- wherein, in Formulae 1 and 9,
- L11 to L13 are each independently selected from:
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, 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, or a divalent non-aromatic condensed heteropolycyclic group;
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, 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, or a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), or —B(Q31)(Q32);
- or
- a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, 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, or a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, or a carbolinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —N(Q21)(Q22), —Si(Q21)(Q22)(Q23), or —B(Q21)(Q22),
- a11 to a13 are each independently selected from 1, 2, 3, 4 or 5,
- R11 to R13 are each independently selected from RHT or RET, provided that at least one selected from R11 to R13 is RET,
- R14 to R16 are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
- or
- a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, or a carbolinyl group, each substituted with at least one selected from a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, or a group represented by Formula 9,
- n11 to n13 are each independently selected from 0, 1 or 2,
- the sum of n11, n12, and n13 is selected from 1, 2, 3, 4, 5 or 6,
- RHT is selected from:
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, a benzothiophenyl group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), or —B(Q1)(Q2);
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, or a benzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a group represented by Formula 9, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or —B(Q31)(Q32);
- or
- a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, or a benzothiophenyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a group represented by Formula 9, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), or —B(Q21)(Q22),
- RET is selected from 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzophenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a naphthoimidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a carbolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyrimidobenzothiophenyl group, or —P(═O)(Q1)(Q2);
- 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzophenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a naphthoimidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a carbolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, or a pyrimidobenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbolinyl group, a group represented by Formula 9, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32);
- or
- 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzophenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a naphthoimidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a carbolinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, or a pyrimidobenzothiophenyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbolinyl group, a group represented by Formula 9, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), or —P(═O)(Q21)(Q22),
- X91 is selected from a single bond, O, S, C(R93)(R94), B(R93), P(R93), or P(R93)(R94), provided that X91 is not a single bond when RET is a group substituted with a group represented by Formula 9,
- X92 is selected from O, S, C(R95)(R96), B(R95), P(R95), or P(R95)(R96), provided that, when RHT is a group represented by Formula 9 and one of X91 or X92 is S, the other one of X91 or X92 is not a single bond, O, or S,
- A91 and A92 are each independently selected from a benzene group, a naphthalene group, an anthracene group, or a phenanthrene group,
- R91 to R96 are each independently selected from:
- hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or —B(Q31)(Q32);
- or
- a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), or —B(Q21)(Q22),
- b91 is selected from 1, 2, 3, 4 or 5,
- b92 is selected from 1, 2, 3, 4, 5 or 6, or
- Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group,
38 more elements
Dependencies are inferred from the claim text.