Patent Application
20230217817
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0001685, filed on Jan. 5, 2022, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
One or more embodiments relate to a light-emitting device and an electronic apparatus including the same.
Self-emissive devices from among light-emitting devices have wide viewing angles, high contrast ratios, short response times, and/or excellent or suitable characteristics in terms of luminance, driving voltage, and/or response speed.
In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer region to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.
Aspects according to one or more embodiments of the present disclosure are directed toward a light-emitting device and an electronic apparatus including the light-emitting device.
Additional aspects will be set forth in part in the description, which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments,
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and duplicative descriptions thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the drawings, to explain aspects of the present description. As utilized herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression such as “at least one of a, b or c”, “at least one selected from a, b, and c”, “at least one selected from the group consisting of a, b, and c”, etc., indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variation(s) thereof.
A light-emitting device according to an embodiment of the disclosure includes: a first electrode; a second electrode facing the first electrode; and an interlayer including an emission layer arranged between the first electrode and the second electrode and an electron transport region arranged between the emission layer and the second electrode,
the electron transport region may include a first electron transport layer arranged between the emission layer and the second electrode and a second electron transport layer arranged between the first electron transport layer and the second electrode, the first electron transport layer may include a first compound, the second electron transport layer may include a second compound, the first compound may include a pyrimidine group, the second compound may include a triazine group, and an absolute value of a lowest unoccupied molecular orbital (LUMO) energy of the first compound (ELUMO_E1) may be less than an absolute value of a LUMO energy of the second compound (ELUMO_E2).
In an embodiment, the LUMO energy level may be evaluated by utilizing the Gaussian 09 program with molecular structure enhancement or optimization obtained by B3LYP-based density functional theory (DFT).
In an embodiment, the first compound may include a pyrimidine group, and may not include (e.g., may exclude) a triazine group.
In an embodiment, the second compound may include a triazine group, and may not include (e.g., may exclude) a pyrimidine group.
In an embodiment, at least one of the first compound or the second compound may further include a cyano group.
In an embodiment, the first compound or the second compound may further include a nitrogen-free cyclic group.
In an embodiment, the first compound or the second compound may further include a C6-C14 carbocyclic group.
In an embodiment, the first compound may be represented by Formula 1 and may not include (e.g., may exclude) a triazine group (e.g., any triazine group), and the second compound may be represented by Formula 2 and may not include (e.g., may exclude) a pyrimidine group (e.g., any pyrimidine group).
In Formulae 1 and 2,
L1 to L4 and L11 to L13 may each independently be a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each independently be a single bond, a C6-C14 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C3-C14 nitrogen-free heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each independently be a nitrogen-free cyclic group. In an embodiment, L1 to L4 and L11 to L13 may each independently be a C6-C14 carbocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each independently be: a single bond; a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a 9,9′-dimethylfluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a fluoranthenylene group, a pyrenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a phenanthrolenylene group, a dibenzoquinolenylene group, a bipyridinylene group, or a pyridinylene group; or a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a 9,9′-dimethylfluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a fluoranthenylene group, a pyrenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a bipyridinylene group, or a pyridinylene group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, 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 9,9′-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl 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 carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a dibenzoquinolinyl group, a dibenzoisoquinolinyl group, a biphenyl group, a phenylpyridinyl group, a phenanthronyl group, a dibenzoquinol group, a bipyridinyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each independently be: a single bond; a phenylene group, a naphthylene group, a 9,9′-dimethylfluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a fluoranthenylene group, a pyrenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a phenanthronylene group, a dibenzoquinolenylene group, a bipyridinylene group, or a pyridinylene group; or a phenylene group, a naphthylene group, a 9,9′-dimethylfluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, phenalenylene group, a phenanthrenylene group, a fluoranthenylene group, a pyrenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a bipyridinylene group, or a pyridinylene group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 9,9′-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a fluoranthenyl group, a pyrenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a dibenzoquinolinyl group, a dibenzoisoquinolinyl group, a biphenyl group, a phenylpyridinyl group, a phenanthronyl group, a dibenzoquinol group, a bipyridinyl group, a pyridinyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each independently be: a single bond; a phenylene group, a naphthylene group, or a 9,9′-dimethylfluorenylene group; or a phenylene group, a naphthylene group, or a 9,9′-dimethylfluorenylene group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, L1 to L4 and L11 to L13 may each not be any of the groups selected from an anthracenylene group, a 9,9′-diphenylfluorenylene group, a phenanthrenylene group, a chrysenylene group, a benzochrysenylene group, a triphenylenylene group, a spirofluorenylene group, and a spirofluorenexanthenylene group. That is, none of L1 to L4 and L11 to L13 may be any of the groups selected from an anthracenylene group, a 9,9′-diphenylfluorenylene group, a phenanthrenylene group, a chrysenylene group, a benzochrysenylene group, a triphenylenylene group, a spirofluorenylene group, and a spirofluorenexanthenylene group.
In an embodiment, in Formula 1, L1 to L4 may each not be a triazine group. That is, none of L1 to L4 may be a triazine group.
In an embodiment, in Formula 2, L11 to L13 may each not be a pyrimidine group. That is, none of L11 to L13 may be a pyrimidine group.
In an embodiment, in Formula 1, at least one of L1 to L4 may be a phenylene group, and a1 to a4 may each be 1.
In an embodiment, in Formula 2, at least one of L11 to L13 may be a phenylene group, and a11 to a13 may each be 1.
In Formulae 1 and 2, a1 to a4 and a11 to a13 may each independently be an integer from 0 to 3. a1 to a4 and a11 to a13 may respectively indicate the numbers of L1(s) to L4(s) and L11(s) to L13(s).
In an embodiment, when a1 is an integer of 2 or more, two or more of L1(s) may be identical to or different from each other. In an embodiment, when a2 is an integer of 2 or more, two or more of L2(s) may be identical to or different from each other. In an embodiment, when a3 is an integer of 2 or more, two or more of L3(s) may be identical to or different from each other. In an embodiment, when a4 is an integer of 2 or more, two or more of L4(s) may be identical to or different from each other. In an embodiment, when a11 is an integer of 2 or more, two or more of L11(s) may be identical to or different from each other. In an embodiment, when a12 is an integer of 2 or more, two or more of L12(s) may be identical to or different from each other. In an embodiment, when a13 is an integer of 2 or more, two or more of L13(s) may be identical to or different from each other. In an embodiment, when a14 is an integer of 2 or more, two or more of L14(s) may be identical to or different from each other.
In an embodiment, in Formulae 1 and 2, a1 to a4 and a11 to a13 may each independently be an integer from 0 to 2.
In Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C7-C60 aryl alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 heteroaryl alkyl group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a nitrogen-free C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a. In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be a C6-C14 carbocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formulae 1 and 2, at least one of R1 to R4 and R11 to R13 may be a cyano group.
In an embodiment, in Formula 1, R1 to R4 may each not be a triazine group. That is, none of R1 to R4 may be a triazine group. In an embodiment, in Formula 2, R11 to R13 may each not be a pyrimidine group. That is, none of R11 to R13 may be a pyrimidine group.
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, -CD3, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group; a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a 9,9′-methylfluorenyl group, a fluoranthenyl group, a pyrenyl 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 indenyl 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 benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzoisothiazolyl 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 dibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azafluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or an azadibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a 9,9′-methylfluorenyl group, a fluoranthenyl group, a pyrenyl 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 indenyl 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 benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzoisothiazolyl 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 dibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, naphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof; or —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2), and
Q1 to Q3 and Q31 to Q33 may each independently be: —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, a cyano group, —CD3, a tert-butyl group, a C1-C20 alkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be: hydrogen, deuterium, —F, a cyano group, —CD3, a C1-C20 alkyl group, or a C1-C20 alkoxy group; a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, or any combination thereof; or a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a 9,9′-dimethylfluorenyl group, a thiophenyl group, a furanyl group, an indenyl group, an isoindolyl group, an indolyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a 9,9′-dimethylfluorenyl group, a thiophenyl group, a furanyl group, an indenyl group, an isoindolyl group, an indolyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be: hydrogen, deuterium, —F, a methyl group, an iso-propyl group, a tert-butyl group, or a cyano group; or a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a 9,9′-dimethylfluorenyl group, a quinolinyl group, an isoquinolinyl group, or a carbazolyl group, each unsubstituted or substituted with deuterium, —F, a tert-butyl group, a cyano group, a C1-C20 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a C1-C20 alkylphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each independently be: hydrogen, deuterium, a C1-C20 alkyl group, or a cyano group; or a phenyl group, a biphenyl group, a naphthyl group, or a 9,9′-dimethylfluorenyl group, each unsubstituted or substituted with deuterium, a cyano group, a C1-C20 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a C1-C20 alkylphenyl group, or any combination thereof.
In an embodiment, in Formulae 1 and 2, R1 to R4 and R11 to R13 may each not be any of the groups selected from an anthracenyl group, a 9,9′-diphenylfluorenyl group, a phenanthrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a spirofluorenyl group, and a spirofluorenexanthenyl group. That is, none of R1 to R4 and R11 to R13 may be any of the groups selected from an anthracenyl group, a 9,9′-diphenylfluorenyl group, a phenanthrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a spirofluorenyl group, and a spirofluorenexanthenyl group.
In Formulae 1 and 2, b1 to b4 and b11 to b13 may each independently be an integer from 0 to 10. b1 to b4 and b11 to b13 may respectively indicate the numbers of R1(s) to R4(s) and R11(s) to R13(s).
In an embodiment, when b1 is an integer of 2 or more, two or more of R1(s) may be identical to or different from each other. In an embodiment, when b2 is an integer of 2 or more, two or more of R2(s) may be identical to or different from each other. In an embodiment, when b3 is an integer of 2 or more, two or more of R3(s) may be identical to or different from each other. In an embodiment, when b4 is an integer of 2 or more, two or more of R4(s) may be identical to or different from each other. In an embodiment, when b11 is an integer of 2 or more, two or more of R11(s) may be identical to or different from each other. In an embodiment, when b12 is an integer of 2 or more, two or more of R12(s) may be identical to or different from each other. In an embodiment, when b13 is an integer of 2 or more, two or more of R13(s) may be identical to or different from each other.
In an embodiment, in Formulae 1 and 2, b1 to b4 and b11 to b13 may each independently be an integer from 0 to 5.
In an embodiment, the first compound may be represented by Formula 1a, and the second compound may be represented by Formula 2a.
In Formulae 1a and 2a, R5 to R7 and R15 to R17 may each independently the same as described in connection with R1 in the present specification.
In an embodiment, in Formulae 1a and 2a, R5 to R7 and R15 to R17 may each independently be a C6-C14 carbocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formula 1a, R5 to R7 may each not be a triazine group. That is, none of R5 to R7 may be a triazine group. In an embodiment, in Formula 2a, R15 to R17 may each not be a pyrimidine group. That is, none of R15 to R17 may be a pyrimidine group.
In an embodiment, the first compound may be one of compounds represented by Formulae 1-1 to 1-16.
In an embodiment, the second compound may be one of compounds represented by Formulae 2-1 to 2-16.
In an embodiment, the emission layer may include a host and a dopant, and the host may include two different hosts, each independently represented by Formula 3.
In Formula 3, Ar31 and L31 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
In an embodiment, the emission layer may include a host and a dopant, and the host may include a first host represented by Formula 3a or 3b and a second host represented by Formula 4a or 4b.
In Formulae 3a, 3b, 4a, and 4b, ring CY32 to ring CY35 and ring CY42 and ring CY43 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, ring CY32 to ring CY35 and ring CY42 and ring CY43 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a carbazole group, a dibenzofuran group, a fluorene group, a dibenzothiophene group, or a dibenzosilole group.
In an embodiment, ring CY32 to ring CY35, ring CY42, and ring CY43 may each independently be a benzene group, a naphthalene group, or a phenanthrene group.
In Formula 3b, X36 may be O, S, N(T36), C(R36)(R37), or Si(R36)(R37).
In an embodiment, in Formula 3b, X36 may be O or N(T36).
In Formula 4b, X41 may be N, C(R41), or Si(R41), X42 may be N, C(R42), or Si(R42), and X43 may be N, C(R43), or Si(R43).
In an embodiment, in Formula 4b, X41 may be N or C(R41), X42 may be N or C(R42), and X43 may be N or C(R43).
In an embodiment, the second host may be represented by Formula 4b and may satisfy one of Conditions 4-1 to 4-3.
In Formulae 3a, 3b, 4a, and 4b, T31 may be *-[(L31)a31-R31], T32 may be *-[(L32)a32-R32], T33 may be *-[(L33)a33-R33], T34 may be *-[(L34)a34-R34], T35 may be *-[(L35)a35-R35], T36 may be *-[(L36)a36-R36], T41 may be *-[(L41)a41-R41], T42 may be *-[(L42)a42-R42], T43 may be *-[(L43)a43-R43], T44 may be *-[(L44)a44-R44], T45 may be *-[(L45)a45-R45], and T46 may be *-[(L46)a46-R46]. * indicates a binding site to a neighboring atom.
In Formulae 3a, 3b, 4a, and 4b, L31 to L36 and L41 to L46 may each independently each independently be a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, L31 to L36 and L41 to L46 may each independently be: a single bond;
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, L31 to L36 and L41 to L46 may each independently be: a single bond;
a phenylene group, a naphthylene group, a fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a phenanthronylene group, a dibenzoquinolene group, a bipyridinylene group, or a pyridinylene group; or a phenylene group, a naphthylene group, a fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a dibenzoquinolinylene group, a dibenzoisoquinolinylene group, a biphenylene group, a phenylpyridinylene group, a phenanthronylene group, a dibenzoquinolene group, a bipyridinylene group, or a pyridinylene group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl 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 thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a dibenzoquinolinyl group, a dibenzoisoquinolinyl group, a biphenyl group, a phenylpyridinyl group, a phenanthronyl group, a dibenzoquinol group, a bipyridinyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), or any combination thereof.
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, L31 to L36 and L41 to L46 may each independently be: a single bond; or
a phenylene group, a naphthylene group, a fluorenylene group, a triphenylenylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, or a dibenzocarbazolylenegroup; or a phenylene group, a naphthylene group, a fluorenylene group, a triphenylenylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, or dibenzocarbazolylenegroup, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolyl group, a dibenzocarbazolyl group, or any combination thereof.
In Formulae 3a, 3b, 4a, and 4b, a31 to a36 and a41 to a46 may each independently be an integer from 0 to 3.
a31 to a36 and a41 to a46 may respectively indicate the numbers of L31(s) to L36(s) and L44(s) to L46(s). When a31 is an integer of 2 or more, two or more of L31(s) may be identical to or different from each other. When a32 is an integer of 2 or more, two or more of L32(s) may be identical to or different from each other. When a33 is an integer of 2 or more, two or more of L33(s) may be identical to or different from each other. When a34 is an integer of 2 or more, two or more of L34(s) may be identical to or different from each other. When a41 is an integer of 2 or more, two or more of L41(s) may be identical to or different from each other. When a42 is an integer of 2 or more, two or more of L42(s) may be identical to or different from each other. When a43 is an integer of 2 or more, two or more of L43(s) may be identical to or different from each other. When a44 is an integer of 2 or more, two or more of L44(s) may be identical to or different from each other. When a45 is an integer of 2 or more, two or more of L45(s) may be identical to or different from each other. When a46 is an integer of 2 or more, two or more of L46(s) may be identical to or different from each other.
In an embodiment, a31 to a36 and a41 to a46 may each independently be an integer of 0 to 2.
In Formulae 3a, 3b, 4a, and 4b, R31 to R37 and R41 to R46 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C7-C60 aryl alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 heteroaryl alkyl group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, R31 to R37 and R41 to R46 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —CD3, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, R31 to R37 and R41 to R46 may each independently be: hydrogen, deuterium, —F, a cyano group, —CD3, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, in Formulae 3a, 3b, 4a, and 4b, R31 to R37 and R41 to R46 may each independently be: hydrogen, deuterium, —F, a methyl group, an iso-propyl group, a tert-butyl group, or a cyano group;
a phenyl group, a biphenyl group, a naphthyl group, a C1-C20 alkylphenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a tert-butyl group, a cyano group, a C1-C20 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a C1-C20 alkylphenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; or —Si(Q1)(Q2)(Q3).
In Formulae 3a, 3b, 4a, and 4b, b32 to b35, b42, and b43 may each independently be an integer from 0 to 10.
b32 to b35 and b42 to b43 may respectively indicate the numbers of T32(s) to T35(s) and T42(s) to T43(s). When b32 is an integer of 2 or more, two or more of T32(s) may be identical to or different from each other. When b33 is an integer of 2 or more, two or more of T33(s) may be identical to or different from each other. When b34 is an integer of 2 or more, two or more of T34(s) may be identical to or different from each other. When b35 is an integer of 2 or more, two or more of T35(s) may be identical to or different from each other. When b42 is an integer of 2 or more, two or more of T42(s) may be identical to or different from each other. When b43 is an integer of 2 or more, two or more of T43(s) may be identical to or different from each other.
In an embodiment, b32 to b35 and b42 to b43 may each independently be an integer from 0 to 5.
In an embodiment, the first host may be one of compounds represented by Formulae 3-1 to 3-22.
In an embodiment, the second host may be one of compounds represented by Formulae 4-1 to 4-16.
In an embodiment, the emission layer may include a host and a dopant, and the dopant may be an organometallic compound represented by Formula 5.
In Formulae 5 and 5a, M may be iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm).
In an embodiment, in Formula 5, M may be iridium (Ir) or platinum (Pt).
In Formula 5, L51 may be a ligand represented by Formula 5a.
In Formula 5, a51 may be an integer from 1 to 3. a51 may indicate the number of L51(s). When a51 is 2 or 3, two or three of L51(s) may be identical to or different from each other.
When a51 is 2 or 3, two rings CY51 of two or more of L51(s) may optionally be linked together via T52, which is a linking group, or two rings CY52 may optionally be linked together via T53, which is a linking group.
In Formula 5, L52 may be an organic ligand.
In an embodiment, the organic ligand may be a halogen group, a diketone group, a carboxylic acid group, —C(═O), an isonitrile group, a —CN group, a phosphorus group, or any combination thereof.
In Formula 5, a52 may be an integer from 1 to 3. a52 may indicate the number of L52(s). When a52 is 2 or 3, two or three of L52(s) may be identical to or different from each other.
In Formula 5a, X51 and X52 may each independently be nitrogen or carbon.
In an embodiment, in Formula 5a, X51 and X52 may satisfy one of Conditions 5-1 to 5-3.
In an embodiment, in Formula 5a, X51 and X52 may satisfy Condition 5-1 or 5-2.
In Formula 5a, ring CY51 and ring CY52 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, in Formula 5a, ring CY51 and ring CY52 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, an imidazole group, a pyrazole group, a pyridine group, a pyrimidine group, a pyridoindole group, a benzimidazole group, a carbazole group, a dibenzofuran group, a fluorene group, a dibenzothiophene group, or a dibenzosilole group.
In an embodiment, in Formula 5a, ring CY51 and ring CY52 may each independently be a benzene group, an imidazole group, a pyrazole group, a pyridine group, a pyrimidine group, a pyridoindole group, a benzimidazole group, or a carbazole group.
In Formula 5a, T51 to T53 may each independently be a single bond, *“—O—*”’, *“—S—*”’ , *“—C(═O)—*”’, *“—N(Q411)—*”’, *“—C(Q411)(Q412)—*”’, *“—C(Q411)═C(Q412)—*”’, *“—C(Q411)═*”’, or *“═C═*”’. Q411 to Q414 are respectively the same as described in connection with Q1 in the present specification.
In an embodiment, in Formula 5a, T51 to T53 may each independently be a single bond or *“—O—*”’.
In Formula 5a, R51 and R52 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group that is unsubstituted or substituted with at least one R10a, a C1-C20 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q401)(Q402)(Q403), —N(Q401)(Q402), —B(Q401)(Q402), —C(═O)(Q401), —S(═O)2(Q401), or —P(═O)(Q401)(Q402).
Q401 to Q403 are respectively the same as described in connection with Q1 in the present specification.
In an embodiment, in Formula 5a, R51 and R52 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —CD3, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, in Formula 5a, R51 and R52 may each independently be: hydrogen, deuterium, —F, a cyano group, —CD3, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, in Formula 5a, R51 and R52 may each independently be: hydrogen, deuterium, —F, a methyl group, an iso-propyl group, a tert-butyl group, or a cyano group; or
In an embodiment, two or more of R51(s); two or more of R52(s); and R51 and R52 may optionally be bonded together to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, the dopant may be one of compounds represented by Formulae 5-1 to 5-8.
The light-emitting device may include an electron transport region including a first electron transport layer and a second electron transport layer. The first electron transport layer may include a first compound, the second electron transport layer may include a second compound, the first compound may include a pyrimidine group, the second compound may include a triazine group, and an absolute value of a LUMO energy of the first compound (ELUMO_E1) may be less than an absolute value of a LUMO energy of the second compound (ELUMO_E2).
Although embodiments are not limited by any specific theory, the light-emitting device as described above may include the first and second electron transport layers, each with a repective specific compound, and the specific compounds included in the first and second electron transport layers satisfy a specific LUMO energy condition, resulting in improvement in electron mobility.
Therefore, because the electron transport region has improved electron mobility, an electronic device, for example, a light-emitting device, including the electron transport region including the first electron transport layer and the second electron transport layer, may have low voltage characteristics and/or an improved lifespan.
Synthesis method of the compound represented by Formula 1, the compound represented by Formula 2, the compound represented by Formula 3, the compound represented by Formula 4, and the compound represented by Formula 5 may be recognizable by one of ordinary skill in the art by referring to Examples provided below.
In an embodiment,
In an embodiment,
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
The electron transport region may further include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
The emission layer may be to emit red light, green light, blue light, and/or white light.
In an embodiment, the emission layer may be to emit blue light. The blue light may have a maximum emission wavelength of, for example, about 400 nm to about 490 nm. The blue light may have a maximum emission wavelength of, for example, about 440 nm to about 480 nm.
In an embodiment, the emission layer may further include a host (i.e., another host) other than the first host and the second host.
In an embodiment, the emission layer may further include a phosphorescent dopant, a delayed fluorescence material, or a combination thereof. In an embodiment, the emission layer may further include a phosphorescent dopant other than the above host(s) and the above dopant(s).
In an embodiment, the dopant may include a transition metal and ligand(s) in the number of m, m may be an integer from 1 to 6, the ligand(s) in the number of m may be identical to or different from each other, at least one of the ligand(s) in the number of m may be bound to the transition metal via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordinate bond. For example, at least one of the ligand(s) in the number of m may be a carbene ligand (e.g., Ir(pmp)3 and/or the like). The transition metal may be, for example, iridium, platinum, osmium, palladium, rhodium, or gold. The emission layer and the dopant may respectively be the same as described in the present specification.
In an embodiment, the light-emitting device may include a capping layer located outside the first electrode or located outside the second electrode.
For example, the light-emitting device may further include at least one of a first capping layer located outside the first electrode or a second capping layer located outside the second electrode. More details for the first capping layer and/or second capping layer are respectively the same as described in the present specification.
The wording “(interlayer and/or electron transport layer) includes a compound” as used herein may refer to that the (interlayer and/or electron transport layer) may include one kind of compound represented by Formula 1 or two or more different kinds of compounds, each represented by Formula 1.
In an embodiment, the electron transport region may include the compound represented by Formula 1 and the compound represented by Formula 2.
In an embodiment, the compound represented by Formula 1 may be included in the first electron transport layer. In an embodiment, the compound represented by Formula 2 may be included in the second electron transport layer.
The term “interlayer” as utilized herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.
According to one or more embodiments, provided is an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. In an embodiment, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. More details for the electronic apparatus are as described in the present specification.
Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described in connection with
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be utilized as a material for forming a first electrode.
The first electrode 110 may have a single-layered structure consisting of a single layer or a multilayer structure including a plurality of layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region arranged between the first electrode 110 and the emission layer.
The interlayer 130 may further include one or more metal-containing compounds such as one or more organometallic compounds, inorganic materials such as quantum dots, and/or the like, in addition to one or more suitable organic materials.
In an embodiment, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, with constituting layers of each structure being stacked sequentially from the first electrode 110 in the respective stated order.
The hole transport region may further include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
wherein, in Formulae 201 and 202,
In an embodiment, each of Formulae 201 and 202 may include at least one of the groups represented by Formulae CY201 to CY217:
wherein in Formulae CY201 to CY217, R10b and R10c may each independently be the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described above.
In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In an embodiment, each of Formulae 201 and 202 may include at least one of the groups represented by Formulae CY201 to CY203.
In an embodiment, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
In an embodiment, xa1 in Formula 201 may be 1, R201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203.
In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203, and may include at least one of the groups represented by Formulae CY204 to CY217.
In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY217.
In an embodiment, the hole transport region may include at least one of Compounds HT1 to HT50, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4’,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce the leakage of electrons from the emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, a LUMO energy level of the p-dopant may be about -3.5 eV or less.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing an element EL1 and an element EL2 (to be described in more detail below), or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and/or the like.
In Formula 221,
In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a non-metal, a metalloid, or a combination thereof.
Examples of the metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
In an embodiment, examples of the compound containing the element EL1 and the element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, or a metal iodide), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or any combination thereof.
Examples of the metal oxide may include tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoOs, Mo2O5, etc.), and rhenium oxide (for example, ReO3, etc.).
Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.
Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, Nal, Kl, Rbl, and Csl.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mgl2, Cal2, Srl2, and Bal2
Examples of the transition metal halide may include titanium halide (for example, TiF4, TiCl4, TiBr4, Til4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, Zrl4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, Hfl4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, Vl3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, Nbl3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, Tal3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, Crl3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, Mol3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, Wl3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, Mnl2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, Tcl2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, Rel2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, Fel2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, Rul2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, Osl2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, Col2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, Rhl2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, Irl2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, Nil2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, Pdl2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, Ptl2, etc.), copper halide (for example, CuF, CuCl, CuBr, Cul, etc.), silver halide (for example, AgF, AgCl, AgBr, Agl, etc.), and gold halide (for example, AuF, AuCl, AuBr, Aul, etc.).
Examples of the post-transition metal halide may include zinc halide (for example, ZnF2, ZnCl2, ZnBr2, Znl2, etc.), indium halide (for example, Inl3, etc.), and tin halide (for example, Snl2, etc.).
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, Ybl, Ybl2, Ybl3, and Sml3.
Examples of the metalloid halide may include antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light. In an embodiment, the emission layer may be to emit blue light.
In an embodiment, a wavelength of the blue light may be in a range of about 440 nm to about 480 nm.
In an embodiment, the emission layer may include a host and a dopant, and the host may include two different hosts represented by Formula 3.
The dopant may include the organometallic compound represented by Formula 5.
The phosphorescent dopant or the fluorescent dopant that may be included in the emission layer may be understood by referring to the descriptions of the phosphorescent dopant or the fluorescent dopant provided herein.
In an embodiment, the emission layer may include a quantum dot.
In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act (e.g., serve) as a host or a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable light-emission characteristics may be obtained without a substantial increase in driving voltage.
The host may include a carbazole-containing compound, an anthracene-containing compound, a triazine-containing compound, or any combination thereof. The host may further include, for example, a carbazole-containing compound and a triazine-containing compound.
In an embodiment, the host may further include a compound represented by Formula 301:
wherein, in Formula 301,
In an embodiment, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In an embodiment, the host may further include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
wherein, in Formulae 301-1 and 301-2,
In an embodiment, the host may further include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In an embodiment, the host may further include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In an embodiment, the host may further include at least one of Compounds H1 to H131, 9,10-di(2-naphthyl)anthracene (DNA), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
wherein, in Formulae 401 and 402,
In an embodiment, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In an embodiment, when xc1 in Formula 402 is 2 or more, two ring A401 in two or more of L401(s) may be optionally linked to each other via T402, which is a linking group, and/or two ring A402 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as described in connection with T401.
L402 in Formula 401 may be an organic ligand. In an embodiment, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, -CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, at least one of Compounds PD1 to PD39, at least one of PS-1 and PS-2, or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
wherein, in Formula 501,
In an embodiment, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
In an embodiment, xd4 in Formula 501 may be 2.
In an embodiment, the fluorescent dopant may include: at least one of Compounds FD1 to FD36; DPVBi; DPAVBi; or any combination thereof:
The emission layer may include a different delayed fluorescence material.
In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material that is further included in the emission layer may act (e.g., serve) as a host or a dopant, depending on the type or kind of other materials included in the emission layer.
In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material may be greater than or equal to about 0 eV and less than or equal to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
In an embodiment, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, and/or a π electron-deficient nitrogen-containing C1-C60 cyclic group), and ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).
Examples of the delayed fluorescence material may include at least one of the following Compounds DF1 to DF9:
The emission layer may include a quantum dot.
In the present specification, a quantum dot refers to a crystal of a semiconductor compound, and may include any suitable material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic (e.g., organometallic) chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
In the wet chemical process, a precursor material is mixed with an organic solvent to grow a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts (e.g., serves) as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled or selected through lower cost process which is more easily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) and/or molecular beam epitaxy (MBE).
The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Examples of the Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.
Examples of the group III-V semiconductor compound may include: a binary compound such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and/or InSb; a ternary compound such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GalnNP, GalnNAs, GalnNSb, GalnPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; or any combination thereof. In an embodiment, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and/or the like.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and/or InTe; a ternary compound, such as InGaS3, and/or InGaSe3; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and/or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or any combination thereof.
The Group IV element or compound may include: a single element compound, such as Si and/or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.
Each element included in a multi-element compound such as the binary compound, the ternary compound and/or the quaternary compound, may exist in a particle with a substantially uniform concentration or non-uniform concentration.
In an embodiment, the quantum dot may have a single structure or a dual core-shell structure. In the case of the quantum dot having a single structure, the concentration of each element included in the corresponding quantum dot is substantially uniform. In an embodiment, in a quantum dot with a core-shell structure, the material contained in the core and the material contained in the shell may be different from each other.
The shell of the quantum dot may act (e.g., serve) as a protective layer to prevent or reduce chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The element presented in the interface between the core and the shell of the quantum dot may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the quantum dot.
Examples of the shell of the quantum dot may include (e.g., may be) an oxide of metal, metalloid, or non-metal, a semiconductor compound, and any combination thereof. Examples of the oxide of metal, metalloid, or non-metal may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; or any combination thereof. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. In some embodiments, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AIP, AlSb, or any combination thereof.
A full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In some embodiments, the quantum dot may be a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In an embodiment, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by combining light of one or more suitable colors.
The electron transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron transport region may include the first compound and the second compound.
In an embodiment, the electron transport region may include a first electron transport layer including the first compound and a second electron transport layer including the second compound. In an embodiment, the electron transport region may include an electron transport layer, and the electron transport layer may include the first electron transport layer and the second electron transport layer.
The first electron transport layer may be arranged between the emission layer and the second electrode, and the second electron transport layer may be arranged between the first electron transport layer and the second electrode.
The electron transport region may further include a buffer layer, a hole blocking layer, an electron control layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, with the constituting layers of each structure being sequentially stacked from an emission layer in the respective stated order.
In an embodiment, the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, and/or the electron transport layer in the electron transport region) may further include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, the electron transport region may further include a compound represented by Formula 601.
In Formula 601,
In an embodiment, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked via a single bond.
In an embodiment, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In an embodiment, the electron transport region may further include a compound represented by Formula 601-1:
wherein, in Formula 601-1,
In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include at least one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, TSPO1, TPBl, or any combination thereof:
A thickness of the electron transport region may be from about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be from about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole-blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
In an embodiment, a ratio of a thickness of the first electron transport layer to a thickness of the second electron transport layer may be in a range of about 3:7 to about 7:3. In an embodiment, a ratio of the thickness of the first electron transport layer to the thickness of the second electron transport layer may be in a range of about 4:6 to about 6:4.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
The electron injection layer may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include one or more oxides, halides (for example, fluorides, chlorides, bromides, and/or iodides), and/or tellurides of the alkali metal, the alkaline earth metal, and/or the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include one or more alkali metal oxides, such as Li2O, Cs2O, and/or K2O, alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, an alkali metal halide), or ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited, and/or the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be located on the interlayer 130 having such a structure as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be utilized.
In an embodiment, the second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including two or more layers.
A first capping layer may be located outside the first electrode 110 (e.g., on the side of the first electrode 110 facing oppositely away from the second electrode 150), and/or a second capping layer may be located outside the second electrode 150 (e.g., on the side of the second electrode 150 facing oppositely away from the first electrode 110). In one or embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.
Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted (e.g., emitted) toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer or light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted (e.g., emitted) toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the emission efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and second capping layer may include a material having a refractive index (at a wavelength of 589 nm) of 1.6 or more.
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer or the second capping layer may each independently include one or more carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.
In an embodiment, at least one of the first capping layer or the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In an embodiment, at least one of the first capping layer or the second capping layer may each independently include at least one of Compounds HT28 to HT33, at least one of Compounds CP1 to CP6, β-NPB, P4, or any combination thereof:
The light-emitting device may be included in one or more suitable electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, a quantum dot as described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the plurality of subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the plurality of subpixel areas.
A pixel-defining layer may be located among the plurality of subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns located among the plurality of color filter areas, and the color conversion layer may include a plurality of color conversion areas and light-shielding patterns located among the plurality of color conversion areas.
The plurality of color filter areas (or the color conversion areas) may include a first area emitting a first color light, a second area emitting a second color light, and/or a third area emitting a third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. For example, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include (e.g., may exclude) any quantum dots. The quantum dot is the same as described in the present specification. The first area, the second area, and/or the third area may each further include a scatterer.
In an embodiment, the light-emitting device may be to emit a first light, the first area may be to absorb the first light to emit a first first-color light, the second area may be to absorb the first light to emit a second first-color light, and the third area may be to absorb the first light to emit a third first-color light. In this regard, the first first-color light, the second first-color light, and the third first-color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first first-color light may be red light, the second first-color light may be green light, and the third first-color light may be blue light.
The electronic apparatus may further include a thin-film transistor in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein the source electrode or the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, etc.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion and/or the color conversion layer may be located between the color filter and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, while concurrently (e.g., simultaneously) preventing or reducing ambient air and/or moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
Various suitable functional layers may be additionally located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the usage of the electronic apparatus. The functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device, a biometric information collector.
The electronic apparatus may be applied to one or more suitable displays, light sources, lighting apparatuses, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers (e.g., diaries), electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting apparatus 180 of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be formed on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be located on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor such as silicon and/or polysilicon, an organic semiconductor, and/or an oxide semiconductor, and may include a source region, a drain region and a channel region.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be located on the activation layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be placed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be in contact with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be formed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.
A pixel-defining layer 290 containing an insulating material may be located on the first electrode 110. The pixel-defining layer 290 exposes a region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel-defining layer 290 may be a polyimide or polyacrylic organic film. In one embodiment, one or more layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining layer 290 in the form of a common layer.
The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or a combination thereof; or a combination of the inorganic film and the organic film.
The light-emitting apparatus 190 of
Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10-8 torr to about 10-3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as used herein refers to a cyclic group consisting of only three to sixty carbon atoms as ring-forming atoms, and the term “C1-C60 heterocyclic group” as used herein refers to a cyclic group that has, in addition to one to sixty carbon atoms, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. In an embodiment, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The term “cyclic group” as used herein may include the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used herein refers to a cyclic group that has three to sixty carbon atoms and does not include *—N═*’ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N═*’ as a ring-forming moiety.
In an embodiment,
The term “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, or “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein each refers to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are used. In an embodiment, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may include 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, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include 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, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle and/or at a terminal end (e.g., the terminus) of the C2-C66 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle and/or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof may include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by -OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group that includes, in addition to 1 to 10 carbon atoms, at least one heteroatom as ring-forming atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” used herein refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has, in addition to 1 to 10 carbon atoms, at least one heteroatom as ring-forming atoms, and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having six to sixty carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having six to sixty carbon atoms. Examples of the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl 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 perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a fluorenyl group, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has, in addition to 1 to 60 carbon atoms, at least one heteroatom as ring-forming atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has, in addition to 1 to 60 carbon atoms, at least one heteroatom as ring-forming atoms. Examples of the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiofuranyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an adamantyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other, at least one heteroatom in addition to 1 to 60 carbon atoms as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, an azaadamantyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein refers to a monovalent group represented by -OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein refers to a monovalent group represented by -SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 aryl alkyl group” used herein refers to a monovalent group represented by -A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroaryl alkyl group” used herein refers to a monovalent group represented by -A106A107 (where A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
R10a may be:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 aryl alkyl group; or a C2-C66 heteroaryl alkyl group.
The term “hetero atom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “the third-row transition metal” used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “ter-Bu” or “But” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. The “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was utilized instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2 (1,200 Å) ITO electrode formed thereon was cut to a size of 50 mm×50 mm×0.5 mm, sonicated in isopropyl alcohol and pure water for 5 minutes each, and then cleaned with irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes. Then, the resultant glass substrate was mounted on a vacuum deposition apparatus.
HT1 was deposited on the anode to form a hole injection layer having a thickness of 120 nm, and Compound 3-3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 5 nm.
Compound 3-1 (first host), Compound 4-1 (second host), and Compound 5-1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 7:3:1 to form an emission layer having a thickness of 30 nm.
Next, Compound 1-4, which is a first compound, and ET-D1 (LiQ) were co-deposited on the emission layer at a weight ratio of 5:5 to form a first electron transport layer having a thickness of 10 nm, Compound 2-4, which is a second compound, and ET-D1 (LiQ) were co-deposited on the first electron transport layer at a weight ratio of 5:5 to form a second electron transport layer having a thickness of 10 nm, ET-D1 (LiQ) was deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm, and then Mg:Ag was deposited on the electron injection layer to form a cathode having a thickness of 10 nm, thereby completing manufacture of a light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 1 were utilized to form a first electron transport layer and a second electron transport layer. However, in the case of Comparative Examples 1 and 2, an electron transport layer having a single layer rather than having a multi-layered structure was formed.
The driving voltage at 1,000 cd/m2 and lifespan of the organic light-emitting devices manufactured in Examples 1 to 3 and Comparative Examples 1 to 4 were measured by utilizing the Keithley MU 236 and the luminance meter PR650. The lifespan is a measure of the time taken for the luminance to reduce to 95% of the initial luminance value while a relative luminance change over time was recorded by applying a constant current corresponding to 1,000 cd/m2. The measurement results are shown as relative values with respect to Comparative Example 1. That is, the driving voltage and lifespan shown in Table 1 are relative values with those of Comparative Example 1 as 100%.
Also, a LUMO energy level of each compound was measured by utilizing the Gaussian 09 program with molecular structure optimization obtained by B3LYP-based density functional theory (DFT), and a value thereof is shown in Table 1.
From Table 1, it may be confirmed that when the first electron transport layer and the second electron transport layer each include a specific compound, as in the organic light-emitting devices of Examples 1 to 3, in which the compounds satisfies a specific LUMO energy condition, improved driving voltage and improved efficiency were obtained, as compared to Comparative Examples 1 to 4.
The light-emitting device includes a first electron transport layer and a second electron transport layer, wherein the first electron transport layer includes a first compound represented by Formula 1, the second electron transport layer includes a second compound, and the first compound and the second compound satisfy a specific LUMO energy level relationship, and thus, electron mobility is improved, and the light-emitting device may have excellent or suitable driving voltage and excellent or suitable luminescence lifespan, and may be utilized to manufacture a high-quality electronic apparatus.
The use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
As used herein, the terms “substantially”, “about”, and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” or “approximately,” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ± 30%, 20%, 10%, 5% of the stated value.
Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The electronic apparatus, the display device, and/or any other relevant devices or components according to embodiments of the present invention described herein may be implemented utilizing any suitable hardware, firmware (e.g. an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate.
Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0001685 | Jan 2022 | KR | national |
