Organic light-emitting devices

Abstract

An organic light emitting device is disclosed, which includes a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes a predetermined host and a thermally activated delayed fluorescent emitter.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the priority of Korean Patent Application No. 10-2018-0073403 filed on June 26, 2018 in the Korean Intellectual Property Office and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments relate to an organic light emitting device. Background Art

[0004] An organic light emitting device (OLED) is a self-emitting device that produces full-color images and also has a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to other types of devices.

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.

[0006] Various types of organic light emitting devices are known. However, there is still a need for OLEDs with low driving voltage, high efficiency, high brightness, and long lifetime. Summary of the invention

[0007] Aspects of the present disclosure provide an organic light emitting device having high efficiency and long lifetime.

[0008] 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.

[0009] One aspect provides an organic light emitting device comprising:

[0010] a first electrode;

[0011] a second electrode facing the first electrode; and

[0012] an emission layer disposed between the first electrode and the second electrode,

[0013] wherein the emitting layer comprises a host and a thermally activated delayed fluorescent emitter, and

[0014] wherein the host comprises at least one compound selected from the group consisting of a compound represented by Formula 1 and a compound represented by Formula 2, and CZ in Formulas 1 and 2 is a group represented by Formula CZ1 or CZ2:

[0015]

[0016] In formulas 1, 2, CZ1, and CZ2,

[0017] Ring A 1 , A 2 , A 5 , and A 6 can be independently a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzosilole group, a dibenzofuran group, or a dibenzothiophene group, wherein the ring A in Formula 2 6 may be a dibenzofuran group or a dibenzothiophene group,

[0018] X 22 Can be O or S,

[0019] m can be 0, 1, or 2,

[0020] n can be 0 or 1,

[0021] Z 1 -Z 7 Can be independently:

[0022] Hydrogen, deuterium, or cyano (CN); or

[0023] Each is unsubstituted or substituted by at least one selected from the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, dibenzofuranyl, or dibenzothiophenyl: deuterium, cyano, C 1 -C 20 Alkyl, phenyl, and biphenyl,

[0024] b1-b6 can each independently be 0, 1, 2, or 3,

[0025] * indicates the binding site with the adjacent atom, and

[0026] Each of the compound represented by Formula 1 and the compound represented by Formula 2 may include at least one cyano group. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] By combining Figure 1 These and / or other aspects will become clear and more readily understood from the following description of the embodiments contemplated herein. Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION

[0028] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following merely describes the embodiments with reference to the accompanying drawings to illustrate aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind) of..." modify the entire list of elements without modifying the individual elements of the list when before or after the list of elements.

[0029] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0030] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.

[0031] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0032] The term "or" means "and / or". It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0033] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0034] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are expected. Thus, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as shown herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Thus, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions, and are not intended to limit the scope of the claims.

[0035] As used herein, "about" or "approximately" includes 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 taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within a range of ±10% or 5%.

[0036] According to one or more exemplary embodiments, an organic light emitting device is provided. The organic light emitting device includes a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode.

[0037] The emissive layer may include a host and a thermally activated delayed fluorescent emitter.

[0038] In one or more embodiments, the host may include at least one compound selected from the group consisting of a compound represented by Formula 1 and a compound represented by Formula 2:

[0039]

[0040] CZ in Formulae 1 and 2 may be a group represented by the formula CZ1 or CZ2:

[0041]

[0042] In Formulas 1, 2, CZ1, and CZ2, ring A 1 , A 2 , A 5 , and A 6 can be independently a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzosilole group, a dibenzofuran group, or a dibenzothiophene group, wherein the ring A in Formula 2 6 It may be a dibenzofuran group or a dibenzothiophene group.

[0043] For example, ring A in formula 1 5 and A6 , Ring A in Formula 2 5 , and ring A in formula CZ1 and CZ2 1 and A 2 may each be a phenyl group, and Ring A in Formula 2 6 It may be a dibenzofuran group or a dibenzothiophene group, but embodiments of the present disclosure are not limited thereto.

[0044] X in Formula 1 22 Can be O or S.

[0045] In Formulae 1 and 2, m may be 0, 1, or 2.

[0046] n in Formulas 1 and 2 may be 0 or 1.

[0047] When n in equations 1 and 2 is 0, The group represented by may be a single bond.

[0048] In Formulas 1, 2, CZ1, and CZ2, Z 1 -Z 7 Can be independently:

[0049] Hydrogen, deuterium, or cyano (CN); or

[0050] Each is unsubstituted or substituted by at least one selected from the following C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, dibenzofuranyl, or dibenzothiophenyl: deuterium, cyano, C 1 -C 20 Alkyl, phenyl, and biphenyl.

[0051] In one embodiment, in Formulas 1, 2, CZ1, and CZ2, Z 1 -Z 7 Can be independently:

[0052] hydrogen, deuterium, or cyano; or

[0053] Each is unsubstituted or substituted by at least one selected from the following C 3 -C 10 Alkyl, phenyl, biphenyl, terphenyl, dibenzofuranyl, or dibenzothiophenyl: deuterium, cyano, C 3 -C 10 Alkyl, phenyl, and biphenyl.

[0054] In one or more embodiments, in Formulas 1, 2, CZ1, and CZ2, Z 1 -Z 7 Can be independently:

[0055] hydrogen, deuterium, or cyano; or

[0056] and n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, biphenyl, or terphenyl, each being unsubstituted or substituted with at least one substituted radical selected from the group consisting of deuterium, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and biphenyl.

[0057] In formula 1, 2, CZ1, and CZ2, b1-b6 represent groups Z 1 To group Z 6 The number of b1-b6 is 0, 1, 2, or 3, and each of them can be independently 0, 1, 2, or 3. When b1-b6 are each 2 or greater, two or more corresponding groups Z 1 To group Z 6 For example, b1-b6 may be each independently 0, 1, or 2, but the embodiments of the present disclosure are not limited thereto.

[0058] In formulae CZ1 and CZ2, * indicates a binding site with an adjacent atom.

[0059] Each of the compound represented by Formula 1 and the compound represented by Formula 2 may include at least one cyano group.

[0060] For example, the number of cyano groups included in the compound represented by Formula 1 and the number of cyano groups included in the compound represented by Formula 2 may each independently be 1, 2, 3, or 4 (eg, 1 or 2).

[0061] In one or more embodiments, with respect to Formulas 1 and 2,

[0062] Selected from b1 groups Z 1 and a group Z of number b2 2 At least one of may be a cyano group,

[0063] Selected from the group Z having a number b3 3 and a group Z of number b4 4 At least one of may be a cyano group,

[0064] Selected from the group Z having a number b5 5 and a group Z of number b6 6 At least one of may be a cyano group,

[0065] Selected from b1 groups Z 1 and a group Z of number b2 2 At least one of them may be a cyano group and is selected from a group Z having a number b3 3 and a group Z of number b4 4At least one of may be a cyano group,

[0066] Selected from b1 groups Z 1 and a group Z of number b2 2 At least one of them may be a cyano group and is selected from a group Z having a number b5 5 and a group Z of number b6 6 At least one of may be a cyano group,

[0067] Selected from the group Z having a number b3 3 and a group Z of number b4 4 At least one of them may be a cyano group and is selected from a group Z having a number b5 5 and a group Z of number b6 6 At least one of may be a cyano group, or

[0068] Selected from b1 groups Z 1 and a group Z of number b2 2 At least one of them may be a cyano group and is selected from a group Z having a number b3 3 and a group Z of number b4 4 At least one of them may be a cyano group and is selected from a group Z having a number b5 5 and a group Z of number b6 6 At least one of may be a cyano group.

[0069] In one or more embodiments, CZ in Formulae 1 and 2 may be a group represented by Formula CZ2, and Z in Formula CZ2 7 may be C each substituted with at least one cyano group 1 -C 20 An alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, but embodiments of the present disclosure are not limited thereto.

[0070] In one or more embodiments, the The group represented by may be one selected from the group represented by the formulas PO1 to PO25, PM1 to PM25, PP1 to PP18, MO1 to MO37, MM1 to MM37, MP1 to MP25, OO1 to OO37, OM1 to OM37, OP1 to OP25, O1 to O16, M1 to M16, and P1 to P9, but embodiments of the present disclosure are not limited thereto:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] In formulas PO1 to PO25, PM1 to PM25, PP1 to PP18, MO1 to MO37, MM1 to MM37, MP1 to MP25, OO1 to OO37, OM1 to OM37, OP1 to OP25, O1 to O16, M1 to M16, and P1 to P9, Z 10 To Z 19 Can be independently related to Z 3 and Z 4 The descriptions are the same, and * and *' each indicate a binding site with an adjacent atom.

[0083] In one embodiment, in Formulas PO1 to PO25, PM1 to PM25, PP1 to PP18, MO1 to MO37, MM1 to MM37, MP1 to MP25, OO1 to OO37, OM1 to OM37, OP1 to OP25, O1 to O16, M1 to M16, and P1 to P9, Z 10 To Z 19 It may not be cyano.

[0084] In one or more embodiments, in Formulas PO1 to PO25, PM1 to PM25, PP1 to PP18, MO1 to MO37, MM1 to MM37, MP1 to MP25, OO1 to OO37, OM1 to OM37, OP1 to OP25, O1 to O16, M1 to M16, and P1 to P9, Z 10 To Z 19 Can be independently:

[0085] hydrogen, deuterium, or cyano; or

[0086] and n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, biphenyl, or terphenyl, each being unsubstituted or substituted with at least one substituted radical selected from the group consisting of deuterium, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and biphenyl.

[0087] In one or more embodiments, the The group represented by may be selected from the groups represented by formulae 1(1) to 1(4), and / or

[0088] In formula 2, The group represented by may be selected from the groups represented by formulae 2(1) to 2(12), and / or

[0089] The group represented by formula CZ1 may be selected from the groups represented by formulas CZ1(1) to CZ1(3), and / or

[0090] The group represented by formula CZ2 may be selected from the groups represented by formulas CZ2(1) to CZ2(14), but the embodiments of the present disclosure are not limited thereto:

[0091]

[0092]

[0093] In Formulas 1(1) to 1(4), 2(1) to 2(12), CZ1(1) to CZ1(3), and CZ2(1) to CZ2(14), X 22 , Z 1 , Z 2 , Z 5 -Z 7 b5, and b6 may each independently be the same as described herein, and * indicates a binding site with an adjacent atom.

[0094] For example, in Formulas 1(1) to 1(4), 2(1) to 2(12), CZ1(1) to CZ1(3), and CZ2(1) to CZ2(14), Z 1 , Z 2 , and Z 5 -Z 7 It may not be cyano.

[0095] In one embodiment, in formulas CZ2(1) to CZ2(14), Z 7 The group may be a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with at least one cyano group, a biphenyl group substituted with at least one cyano group, or a terphenyl group substituted with at least one cyano group, but embodiments of the present disclosure are not limited thereto.

[0096] For example, the host may be selected from compounds H1 to H28, but embodiments of the present disclosure are not limited thereto:

[0097]

[0098]

[0099] X in Formula 1 22 is O or S, and ring A in formula 2 6 is a dibenzofuran group or a dibenzothiophene group. Therefore, Formulas 1 and 2 each have an asymmetric structure that must include a dibenzofuran group or a dibenzothiophene group (or a fused cyclic group including a dibenzofuran group or a dibenzothiophene group) in addition to the carbazole-based group represented by CZ, and thus may have a high dipole moment. Therefore, an electronic device such as an organic light-emitting device including at least one selected from a compound represented by Formula 1 and a compound represented by Formula 2 may have excellent luminous efficiency.

[0100] For example, the dipole moment of the compound represented by Formula 1 and the compound represented by Formula 2 may be 3.41 Debye or more, for example, in the range of about 3.41 Debye to about 10 Debye, but embodiments of the present disclosure are not limited thereto.

[0101] The dipole moment can be evaluated by calculating the Mulliken charge and interatomic distance of each atom of the corresponding compound by a density functional theory (DFT) method using a Gaussian program (structural optimization is performed at the B3LYP, 6-31G (d, p) level) and calculating the dipole moment of the corresponding compound therefrom.

[0102] Since Formulas 1 and 2 have an asymmetric structure as described above, but do not include a group represented by *=o (wherein * represents a binding site with an adjacent atom) (for example, a compound containing a phosphine oxide group includes a group represented by *=o), high luminescence efficiency can be achieved and the material used for the emission layer is substantially (essentially) prevented from being decomposed by *=o when the organic light-emitting device is stored and / or driven, thereby "simultaneously" achieving high luminescence efficiency and long life.

[0103] The difference between the triplet energy level (electron volt, eV) of the host and the triplet energy level (eV) of the thermally activated delayed fluorescent emitter may be in the range of about 0.2 eV to about 0.5 eV. Although not wishing to be bound by theory, it is understood that when the difference between the triplet energy level (eV) of the host and the triplet energy level (eV) of the thermally activated delayed fluorescent emitter is within this range, the energy of the triplet excitons generated in the thermally activated delayed fluorescent emitter is prevented from leaking to the host in the emission layer. Therefore, efficient light emission can be achieved and the activated excitation energy level of the host can be suppressed, thereby achieving long-life driving of the organic light-emitting device.

[0104] The triplet energy levels are evaluated using a DFT method with structural optimization at the level of B3LYP / 6-31G(d,p), for example by using a Gaussian program.

[0105] The thermally activated delayed fluorescence emitter may be selected from any compound that can emit delayed fluorescence according to a thermally activated delayed fluorescence emission mechanism.

[0106] In one embodiment, the difference between the singlet energy level (eV) of the thermally activated delayed fluorescent emitter and the triplet energy level (eV) of the thermally activated delayed fluorescent emitter may be in the range of about 0 eV to about 0.5 eV. Although not wishing to be bound by theory, it is understood that when the difference between the singlet energy level (eV) of the thermally activated delayed fluorescent emitter and the triplet energy level (eV) of the thermally activated delayed fluorescent emitter is within this range, up-conversion from triplet to singlet may be effectively achieved, and the fluorescent dopant may emit delayed fluorescence with high efficiency.

[0107] The triplet energy level and the singlet energy level are evaluated by using a DFT method of structural optimization at the level of B3LYP / 6-31G(d,p), for example, by using a Gaussian program.

[0108] In one embodiment, the thermally activated delayed fluorescent emitter may include a compound represented by Formula 11:

[0109] Formula 11

[0110]

[0111] In formula 11, X 1 Can be a single bond, N-[(L 4 ) c4 -R 4 ]、C(R 5 )(R 6 ), O, or S.

[0112] For example, X 1 It may be a single bond, but the embodiments of the present disclosure are not limited thereto.

[0113] In Formula 11, Ring A 1 and Ring A 2 Each of the groups may independently be a benzene group, a naphthalene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

[0114] For example, in Formula 11, Ring A 1 and Ring A 2 may be independently a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, and are selected from ring A 1 and Ring A 2 At least one of may be each independently a phenyl group, but the embodiments of the present disclosure are not limited thereto, and

[0115] L 3 and L 4 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

[0116] For example, in Formula 11, L 3 and L 4 Can be independently selected from:

[0117] phenylene, naphthylene, fluorenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, carbazolylene, dibenzofuranylene, dibenzothiophenylene, and indolocarbazolylene; and

[0118] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, carbazolylene, dibenzofuranylene, dibenzothiophenylene, and indolocarbazolylene: deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, indolecarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 ), and -N(Q 34 )(Q 35 ),and

[0119] Q 31 -Q 35 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. However, embodiments of the present disclosure are not limited thereto.

[0120] In Formula 11, c3 and c4 each represent L 3 The number and L 4 The number of L and L can be independently an integer of 0-4. When c3 is 2 or greater, the group L 3 Two or more of may be different from or the same as each other, and when c4 is 2 or greater, the group L 4 Two or more of may be different or the same as each other. For example, c3 and c4 may each independently be 0, 1, or 2, but the embodiments of the present disclosure are not limited thereto. When c3 is 0, *-(L 3 ) c3 -*' may be a single bond, and when c4 is 0, *-(L 4 ) c4 -*' can be a single bond.

[0121] In formula 11, R 1 -R 6 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 ), and -B(Q 6 )(Q 7 ), where Q 1 -Q 7 Same as described above.

[0122] In one embodiment, in Formula 11, R 3 At least one π-electron-depleted nitrogen-containing cyclic group may be included.

[0123] As used herein, the term "π-electron-depleted nitrogen-containing cyclic group" refers to a group including a cyclic group having at least one *-N=*' portion, and examples thereof include an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, benzoquinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, a diazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0124] In one or more embodiments, R in Formula 11 3 You can choose from:

[0125] Each is unsubstituted or substituted by at least one substituted phenyl, indenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, isoindolyl, indolyl, furanyl, thienyl, thioyl, benzofuranyl, benzothienyl, benzothioyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzothioyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiorrolocarbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, azaindenyl, azaindolyl, azabenzofuranyl, azabenzothiophenyl, azabenzothioyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzothioyl: deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, (C 1 -C10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, terphenyl, di(phenyl)phenyl, di(biphenyl)phenyl, (pyridyl)phenyl, di(pyridyl)phenyl, (pyrimidyl)phenyl, di(pyrimidyl)phenyl, (triazine)phenyl, di(triazine)phenyl, pyridyl, (C 1 -C 10 alkyl)pyridyl, di(C 1 -C 10 alkyl)pyridyl, (phenyl)pyridyl, di(phenyl)pyridyl, (biphenyl)pyridyl, di(biphenyl)pyridyl, (terphenyl)pyridyl, di(terphenyl)pyridyl, (pyridyl)pyridyl, di(pyridyl)pyridyl, (pyrimidinyl)pyridyl, di(pyrimidinyl)pyridyl, (triazine)pyridyl, di(triazine)pyridyl, pyrimidinyl, (C 1 -C 10 alkyl)pyrimidinyl, di(C 1 -C 10 alkyl) pyrimidinyl, (phenyl) pyrimidinyl, di(phenyl) pyrimidinyl, (biphenyl) pyrimidinyl, di(biphenyl) pyrimidinyl, (terphenyl) pyrimidinyl, di(terphenyl) pyrimidinyl, (pyridinyl) pyrimidinyl, di(pyridinyl) pyrimidinyl, (pyrimidinyl) pyrimidinyl, di(pyrimidinyl) pyrimidinyl, (triazinyl) pyrimidinyl, di(triazinyl) pyrimidinyl, triazinyl, (C 1 -C 10 Alkyl) triazine, di(C 1 -C 10 alkyl)triazinyl, (phenyl)triazinyl, di(phenyl)triazinyl, (biphenyl)triazinyl, di(biphenyl)triazinyl, (terphenyl)triazinyl, di(terphenyl)triazinyl, (pyridyl)triazinyl, di(pyridyl)triazinyl, (pyrimidyl)triazinyl, di(pyrimidyl)triazinyl, (triazinyl)triazinyl, di(triazinyl)triazinyl, fluorenyl, di(C 1 -C 10 alkyl)fluorenyl, di(phenyl)fluorenyl, di(biphenyl)fluorenyl, carbazolyl, (C 1 -C 10 alkyl) carbazolyl, (phenyl) carbazolyl, (biphenyl) carbazolyl, dibenzofuranyl, (C 1 -C 10 alkyl)dibenzofuranyl, (phenyl)dibenzofuranyl, (biphenyl)dibenzofuranyl, dibenzothiophenyl, (C 1 -C 10 alkyl)dibenzothiophenyl group, (phenyl)dibenzothiophenyl group, and (biphenyl)dibenzothiophenyl group, but the embodiments of the present disclosure are not limited thereto.

[0126] In one or more embodiments, R in Formula 11 3 You can choose from:

[0127] A group represented by formula 13(1) and 13(2);

[0128] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and indolocarbazolyl; and

[0129] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and indolocarbazolyl, each of which is substituted by at least one member selected from the group consisting of deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, indolocarbazolyl, and -Si(Q 31 )(Q 32 )(Q 33 ),and

[0130] Q 31 -Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0131]

[0132] In formula (13), X 11 -X 15 may be independently C or N, wherein X 11 -X 15 At least one of can be N independently.

[0133] For example, X 11 -X 15 Two or three of may each independently be N.

[0134] In Formula 13(2), Ring A 11 and Ring A 12 may be each independently a benzene group, a naphthyl group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, and is selected from ring A 11 and Ring A 12At least one of each may be independently a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

[0135] For example, Ring A 11 can be a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, and Ring A 12 It may be a benzene group or a naphthalene group, but the embodiments of the present disclosure are not limited thereto.

[0136] In formula (2), X 16 Can be N-[(L 12 ) a12 -R 12 ]、C(R 14 )(R 15 ), O, or S, X 17 Can be a single bond, N-[(L 13 ) a13 -R 13 ]、C(R 16 )(R 17 ), O, or S.

[0137] For example, X 16 Can be O or S, and X 17 It may be a single bond, but the embodiments of the present disclosure are not limited thereto.

[0138] In formulas 13(1) and 13(2), L 11 -L 13 Can each independently have 3 a11-a13 may each independently have the same definition as c3, and R 11 -R 17 Can each independently have 1 The definition is the same as the definition of .

[0139] In Formula 13(2), d16 may be an integer of 0-6, and in Formula 13(1), d14 may be an integer of 0-4.

[0140] In Formulae 13(1) and 13(2), * represents a bonding site with an adjacent atom.

[0141] In one embodiment, R in Formula 11 3 It may be a group represented by one selected from Formulae 13-1 to 13-20, but the embodiments of the present disclosure are not limited thereto:

[0142]

[0143] In formulas 13-1 to 13-20,

[0144] X 16 Can be N-[(L 12 ) a12 -R 12 ]、C(R 14 )(R 15 ), O, or S,

[0145] L 11 and L 12 Can each independently have 3 The same definition as

[0146] a11 and a12 may each independently have the same definition as that of c3,

[0147] R 11 , R 12 , R 14 , and R 15 Can each independently have 1 The same definition as the definition of

[0148] d16 can be an integer from 0 to 6.

[0149] d15 can be an integer from 0 to 5.

[0150] d14 can be an integer from 0 to 4.

[0151] d13 can be an integer from 0 to 3.

[0152] d12 can be an integer from 0 to 2, and

[0153] *Indicates the binding site with the adjacent atom.

[0154] In one embodiment, in Formula 11, R 1 , R 2 , R 5 , and R 6 can be independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, indolecarbazolyl, -Si(Q 1 )(Q 2 )(Q 3 ), and -N(Q 4 )(Q 5 ),and

[0155] Q 1 -Q 5Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0156] In Formula 11, a1 and a2 each represent R 1 The number and R 2 When a1 is 2 or more, the group R 1 Two or more of may be the same or different from each other, and when a2 is 2 or greater, the group R 2 Two or more of may be the same as or different from each other.

[0157] In one embodiment, the thermally activated delayed fluorescent emitter may include a compound represented by one selected from Formulae 11-1 to 11-7, but embodiments of the present disclosure are not limited thereto:

[0158]

[0159] In formulas 11-1 to 11-7,

[0160] X 1 , L 3 , c3, and R 1 -R 3 may be independently the same as described above,

[0161] X 2 Can be N-[(L 5 ) c5 -R 7 ]、C(R 8 )(R 9 ), O, or S,

[0162] L 5 and c5 may each independently have 3 The same definition as c3,

[0163] R 7 Can have R 3 The same definition as the definition of

[0164] R 8 and R 9 Can each independently have 5 and R 6 The same definition as the definition of

[0165] a16 can be an integer from 0 to 6, and

[0166] a14 and a24 may each independently be an integer of 0-4.

[0167] In one embodiment, in Formulas 11-1 to 11-17, 1) when X 2 C(R 8 )(R 9 ), O, or S, R 3 , and 2) when X 2 N-[(L 5 ) c5 -R 7 ], select R 3 and R 7 At least one of the may each independently include at least one π-electron-depleted nitrogen-containing cyclic group.

[0168] In one or more embodiments, in Formulas 11-1 to 11-17, 1) when X 2 C(R 8 )(R 9 ), O, or S, R 3 , and 2) when X 2 N-[(L 5 ) c5 -R 7 ], R 3 and R 7 , can be independently selected from:

[0169] A group represented by formula 13(1) or 13(2) (for example, a group represented by one selected from formulae 13-1 to 13-20);

[0170] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and indolocarbazolyl; and

[0171] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and indolocarbazolyl, each of which is substituted by at least one member selected from the group consisting of deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, indolocarbazolyl, and -Si(Q 31 )(Q 32 )(Q 33 ),

[0172] 1) When X 2 C(R8 )(R 9 ), O, or S, R 3 , and 2) when X 2 N-[(L 5 ) c5 -R 7 ], select R 3 and R 7 At least one of may be each independently a group represented by Formula 13(1) or 13(2) (for example, a group represented by one selected from Formulae 13-1 to 13-20).

[0173] In one embodiment, the thermally activated delayed fluorescent emitter may include a compound represented by Formula 14A:

[0174] Formula 14A

[0175]

[0176] In Formula 14A, R 21 -R 25 can be independently hydrogen, deuterium, cyano, C 1 -C 10 Alkyl, phenyl, biphenyl, or terphenyl.

[0177] In one embodiment, the thermally activated delayed fluorescent emitter may not include a cyano group.

[0178] The thermally activated delayed fluorescent emitter may include at least one compound selected from compounds D1-1 to D1-83, D2-1 to D2-81, D3-1 to D3-81, and D201 to D211, but embodiments of the present disclosure are not limited thereto:

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] The emission layer including the host and the thermally activated delayed fluorescent emitter as described above does not include an organic metal compound containing a transition metal. That is, the emission layer is different from a phosphorescent emission layer including an organic metal compound containing a transition metal and emitting phosphorescence from the organic metal compound containing a transition metal.

[0199] Based on the total emission components emitted from the emission layer including the body and the thermally activated delayed fluorescent emitter, the delayed fluorescence component emitted from the thermally activated delayed fluorescent emitter may be about 20% or greater, about 26.7% or greater, about 90% or greater, about 92% or greater, about 94% or greater, about 96% or greater, or about 98% or greater.

[0200] The emission layer may differently emit red light, green light, and blue light according to a maximum emission wavelength of the thermally activated delayed fluorescent emitter.

[0201] In one embodiment, light emitted from the thermally activated delayed fluorescent emitter in the emission layer may be blue light, but embodiments of the present disclosure are not limited thereto.

[0202] The amount of the thermally activated delayed fluorescent emitter in the emission layer may be in the range of about 0.01 parts by weight to about 30 parts by weight based on 100 parts by weight of the host, but the embodiments of the present disclosure are not limited thereto. Although not wishing to be bound by theory, it is understood that when the amount of the thermally activated delayed fluorescent emitter is within this range, a high-quality organic light-emitting device without concentration quenching can be achieved.

[0203] In one embodiment, since the emission layer includes the main body and the thermally activated delayed fluorescence emitter, but does not include a phosphorescent compound (for example, an organic metal compound containing a transition metal), the organic light-emitting device including the emission layer may not emit phosphorescence but emit delayed fluorescence, and may have both high efficiency and long lifetime.

[0204] Figure 1 FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.

[0205] A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in a general organic light-emitting device may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0206] The first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can be selected from materials having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode can be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the first electrode.

[0207] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0208] The organic layer 15 is provided on the first electrode 11 .

[0209] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0210] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0211] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0212] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are sequentially stacked in the order stated starting from the first electrode 11.

[0213] The hole injection layer may be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.

[0214] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the compound used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and about 0.01 angstroms / second -about However, the deposition conditions are not limited thereto.

[0215] When the hole injection layer is formed using spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature of heat treatment after coating to remove the solvent may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0216] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[0217] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, and a compound represented by the following Formula 202:

[0218]

[0219] Formula 201

[0220]

[0221] Formula 202

[0222]

[0223] Ar in Formula 201 101 and Ar 102 Can be independently selected from:

[0224] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene phenylene, tetraphenylene, perylenene, and pentacene; and

[0225] Each of the following is selected from at least one substituted phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenyl ... phenanthrenylene, fluorenylene, benzo[9,10]phenan phenylene, tetraphenylene, perylene, and pentphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0226] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xb are not limited thereto.

[0227] R in formula 201 and 202 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently selected from:

[0228] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, and C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0229] Each of the following is substituted by at least one C 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, and phosphoric acid group or its salt;

[0230] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl; and

[0231] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 Alkyl, or C 1 -C 10 Alkoxy,

[0232] However, the implementation of the present disclosure is not limited thereto.

[0233] R in Formula 201 109 You can choose from:

[0234] phenyl, naphthyl, anthracenyl, and pyridyl; and

[0235] phenyl, naphthyl, anthracenyl, and pyridyl groups, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, and pyridyl.

[0236] According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0237] Formula 201A

[0238]

[0239] R in Formula 201A 101 , R 111 , R 112 , and R 109 May each independently have the same definition as described above.

[0240] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20 shown below, but are not limited thereto.

[0241]

[0242]

[0243]

[0244] The thickness of the hole transport region may be about 100 angstroms. -about For example, about -about When the hole transport region includes a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about -about and for example about about and the thickness of the hole transport layer may be in the range of about -about and for example about -about While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0245] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0246] The charge generating material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano-containing compound, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano-containing compounds such as the following compound HT-D1 or compound HT-D2, but are not limited thereto.

[0247]

[0248] The hole transport region may include a buffer layer.

[0249] In addition, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

[0250] The hole transport region may further include an electron blocking layer. The electron blocking layer may include, for example, mCP, but the material therefor is not limited thereto.

[0251]

[0252] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, deposition or coating conditions may be similar to those applied when forming the hole injection layer, although deposition or coating conditions may vary depending on the compound used to form the emission layer.

[0253] When the organic light emitting device is a full-color organic light emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer can emit white light.

[0254] The emitting layer may include a host and a thermally activated delayed fluorescent emitter, and the host and the thermally activated delayed fluorescent emitter may be the same as described above.

[0255] The thickness of the emission layer may be about -about For example, about -about Although not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0256] Then, an electron transport region may be disposed on the emission layer.

[0257] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0258] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure including two or more different materials or a single layer structure.

[0259] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.

[0260] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and BPhen, but may also include other materials.

[0261]

[0262] The thickness of the hole blocking layer may be about -about For example, about -about While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking capability without a significant increase in driving voltage.

[0263] The electron transport layer may further include at least one selected from the following: BCP, BPhen, Alq 3 , BAlq, TAZ, and NTAZ.

[0264]

[0265] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:

[0266]

[0267]

[0268] The thickness of the electron transport layer may be about -about For example, about -about Although not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0269] In addition, the electron transport layer may further include a material containing a metal in addition to the materials described above.

[0270] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinolate lithium, LiQ) or ET-D2.

[0271]

[0272] The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 thereto.

[0273] The electron injection layer may include at least one selected from the group consisting of LiF, NaCl, CsF, Li 2 O, and BaO.

[0274] The thickness of the electron injection layer can be about -about For example, about -about Although not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0275] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0276] In the above, reference has been made to Figure 1 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0277] As used herein, the term "C 1 -C60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0278] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0279] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The alkyl group includes at least one carbon-carbon double bond in the middle or at the terminal, and examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0280] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The alkyl group includes at least one carbon-carbon triple bond in the middle or at the terminal, and examples thereof include ethynyl and propynyl. As used herein, the term "C 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0281] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0282] As used herein, the term "C 2 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring atom and having 2 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 2 -C 10 "Heterocycloalkylene" refers to a group having a C 2 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0283] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0284] As used herein, the term "C 2 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, 2 to 10 carbon atoms, and at least one double bond in its ring. 2 -C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term “C 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0285] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0286] As used herein, the term "C 2 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, and 2 to 60 carbon atoms. As used herein, the term "C 2 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, and 2 to 60 carbon atoms. 2 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 2 -C 60 Heteroaryl and C 2 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0287] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 Aryl), as used herein, 6 -C 60 Arylthio represents -SA 103 (A 103 C 6 -C 60 aryl), and as used herein the term "C 7 -C 60 Aralkyl" means -A 104 A 105 (A 105 C 6 -C 59 Aryl and A 104 C 1 -C 54 alkylene).

[0288] As used herein, the term "C1 -C 60 "Heteroaryloxy" refers to -OA 106 (A 106 C 1 -C 60 Heteroaryl), as used herein, 1 -C 60 "Heteroarylthio" means -SA 107 (A 107 C 1 -C 60 heteroaryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 108 A 109 (A 109 C 1 -C 59 Heteroaryl, and A 108 C 1 -C 59 alkylene).

[0289] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having only carbon atoms (e.g., the number of carbon atoms may be in the range of 8-60) as ring-forming atoms, and not having aromaticity in terms of its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0290] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having heteroatoms selected from N, O, P, Si, and S as ring-forming atoms in addition to carbon atoms (e.g., the number of carbon atoms may be in the range of 2-60), and having no aromaticity in terms of its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0291] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 7 -C 60 Arylalkyl, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Heteroarylthio, substituted C 2 -C 60 At least one substituent of the heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0292] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy;

[0293] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3-C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 ), and -B(Q 16 )(Q 17 );

[0294] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroaralkyl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0295] Each of the following is substituted by at least one C 3 -C 10 Cycloalkyl, C1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 ), and -B(Q 26 )(Q 27 );and

[0296] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 ), and -B(Q 36 )(Q 37 ),and

[0297] Q 11 -Q 17 , Q 21 -Q 27 , and Q 31 -Q 37 may be independently selected from hydrogen, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroaralkyl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0298] The term "room temperature" as used herein refers to about 25°C.

[0299] The terms "biphenyl" and "terphenyl" as used herein refer to a monovalent group in which two or three phenyl groups are linked via a single bond.

[0300] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that the amount of B used is the same as the amount of A used in terms of molar equivalents.

[0301] Example

[0302] Synthesis Example 1: Synthesis of Compound H1

[0303] Compound H1 was synthesized according to the following reaction scheme.

[0304]

[0305] Synthesis of intermediate (1)

[0306] Dibenzofuran-2-ylboronic acid (10 g, 47.2 mmol), 3-bromo-2-fluorobenzonitrile (9.43 g, 47.2 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) (10.9 g, 9.4 mmol), and potassium carbonate (K 2 CO 3 ) (19.6 g, 141.5 mmol) was added to a mixture of 100 milliliters (ml) of tetrahydrofuran and 70 ml of distilled water, and the reaction mixture was heated under reflux. After the reaction was completed, the reaction product was cooled to room temperature, and an organic layer was extracted therefrom using ethyl acetate, and the organic layer was washed with anhydrous sodium sulfate (Na 2 SO 4 ) was dried, concentrated, and then separated by silica gel column chromatography (dichloromethane / hexane). The solid obtained therefrom was recrystallized (dichloromethane / methanol) to synthesize Intermediate (1) as a white solid.

[0307] Synthesis of compound H1

[0308] 20 ml of N, N-dimethylformamide was added to sodium hydride (NaH, 60% in mineral oil) (1.9 g, 47.8 mmol) at a temperature of 0°C and stirred for 10 minutes. Then, carbazole (8 g, 47.8 mmol) was dissolved in 30 ml of N, N-dimethylformamide, slowly added to the reaction solution, and the reaction mixture was stirred at room temperature for 2 hours. A mixture of 90 ml of N, N-dimethylformamide and intermediate (1) (10.9 g, 38.0 mmol) was added to the reaction solution. Then, the reaction solution was heated to a temperature of 120°C under reflux. After the reaction was completed, the reaction product was poured into a methanol / water mixture and the precipitate obtained therefrom was filtered. The obtained product obtained by washing with methanol was dissolved in hot toluene and filtered by using silica gel. The solid obtained by concentrating the filtrate obtained therefrom was recrystallized twice (dichloromethane / methanol, ethyl acetate) to provide compound H1 (52% yield).

[0309] MALDI-TOF MS (calculated: 434.49 g / mol, found: 434.15 g / mol).

[0310] Evaluation Example 1: Measurement of Dipole Moment

[0311] The Milligan charge and interatomic distance of each atom of compounds H1 and H21 to H28 were calculated by the DFT method using the Gaussian program (structural optimization was performed at the B3LYP, 6-31G (d, p) level), and the dipole moment of the corresponding compound was calculated therefrom. The results are shown in Table 1.

[0312] Table 1

[0313] Compound No. Dipole moment (Debye) H1 4.6323 H21 3.4481 H22 4.5336 H23 8.5754 H24 8.2051 H25 7.3057 H26 5.2772 H27 8.5898 H28 8.716

[0314]

[0315] Referring to Table 1, it was confirmed that compounds H1 and H21-H28 had relatively high dipole moments.

[0316] Evaluation Example 2: Evaluation of decay time and ratio of delayed fluorescence component

[0317] A quartz substrate was prepared by cleaning it with chloroform and pure water and by -7 The predetermined materials shown in Table 2 were vacuum deposited (co-deposited) at a vacuum degree of 200 torr to prepare films H1, H21, H24, H25, H26, and B each having a thickness of 50 nanometers (nm).

[0318] Table 2

[0319] Film name Compounds used to make membranes Membrane H1 Compound H1: Compound D205 (85:15 volume ratio) Membrane H21 Compound H21: Compound D205 (85:15 volume ratio) Membrane H24 Compound H24: Compound D205 (85:15 volume ratio) Membrane H25 Compound H25: Compound D205 (85:15 volume ratio) Membrane H26 Compound H26: Compound D205 (volume ratio of 85:15) Membrane B Compound B: Compound D205 (volume ratio of 85:15)

[0320] Then, the PL spectra of each of the films H1, H21, H24, H25, H26, and B were evaluated at room temperature by using a time-resolved photoluminescence (TRPL) measurement system FluoTime 300 (manufactured by PicoQuant) and a pump source PLS340 (manufactured by PicoQuant) (excitation wavelength = 340 nm, spectrum width = 20 nm), and the wavelength of the main peak of the spectrum was determined. PLS340 repeats the measurement of the number of photons emitted from each film at the main peak by a photon pulse (pulse width = 500 picoseconds, ps) applied to each film over time based on time-correlated single photon counting (TCSPC), thereby obtaining a TRPL curve that can be fully fitted. For the results obtained therefrom, two or more exponential decay functions are fitted to obtain the TRPL curves of the films H1, H21, H24, H25, H26, and B. 衰减 (E x )(decay time). The function used for fitting is represented by Equation 1, and is taken in the equation used for fitting T 衰减 T obtained by each exponential decay function 衰减 The maximum value among the values ​​is taken as T 衰减 (Ex) and the maximum value is shown in Table 3. Other T 衰减 The value can be used to determine the decay lifetime of the normal fluorescence. At this time, the same measurement is performed again in a dark state (a state in which the pump signal incident on the predetermined film is blocked) for the same measurement time as the measurement time used to calculate the TRPL curve. In this way, a baseline or background signal curve is obtained and used as a baseline for fitting.

[0321] Then, the calculation is done by passing T 衰减 (E x The ratio of the exponential decay curve (=intensity change over time) determined by ) to the total luminescence intensity over time was calculated, and the ratio of the delayed fluorescence component to the total emission component was evaluated. The results are shown in Table 3.

[0322] Equation 1

[0323]

[0324] Table 3

[0325]

[0326]

[0327] Referring to Table 3, it was confirmed that, when compared with the film B, the films H1, H21, H24, H25, and H26 had longer decay times and larger delayed fluorescence component ratios.

[0328] Example 1

[0329] Formed thereon The glass substrate of thick ITO electrode (first electrode, anode) is washed with distilled water ultrasonic wave. When the washing with distilled water is completed, ultrasonic washing is carried out using solvent such as isopropanol, acetone or methanol. The resulting product is dried and then transferred to a plasma washer, and the resulting substrate is washed with oxygen plasma for 5 minutes and then transferred to a vacuum deposition device.

[0330] Compound HT3 and compound HT-D2 are co-deposited on the ITO electrode of the glass substrate to form a A hole injection layer having a thickness of A hole transport layer having a thickness of , and mCP is deposited on the hole transport layer to form a An electron blocking layer with a thickness of , thereby forming a hole transport region.

[0331] Compound H1 (host) and compound D205 (delayed fluorescence emitter) were co-deposited on the hole transport region in a volume ratio of 85:15 to form a The thickness of the emission layer.

[0332] Compound BCP is vacuum deposited on the emission layer to form a A hole blocking layer with a thickness of , compound ET3 and LiQ are vacuum deposited on the hole blocking layer to form a An electron transport layer having a thickness of , and then LiQ is deposited on the electron transport layer to form a An electron injection layer having a thickness of An Al second electrode (cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0333]

[0334] Comparative Examples A and B

[0335] An organic light emitting device was manufactured in the same manner as in Example 1, except that the host in the emission layer was changed as shown in Table 4.

[0336] Evaluation Example 3: Evaluation of the performance of the organic light-emitting device

[0337] The maximum external quantum efficiency (EQE) of Example 1 and Comparative Examples A and B was measured by using a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A).最大 ), at 500 candela / m2 (cd / m 2 ) under external quantum efficiency (EQE), and lifetime (T 80 ), and the results are shown in Table 4. The lifespan (T 80 ) data (at 500cd / m 2 ) represents the amount of time (hours, h) that has elapsed when the brightness is 80% of the initial brightness (100%).

[0338] Table 4

[0339]

[0340]

[0341] Referring to Table 4, it is confirmed that, compared with the organic light-emitting devices of Comparative Examples A and B, the organic light-emitting device of Example 1 has improved luminous efficiency and lifespan characteristics “at the same time”.

[0342] The organic light emitting device according to the embodiment may have high efficiency and a long lifespan.

[0343] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0344] Although one or more embodiments have been described with reference to the drawings, persons skilled in the art will recognize that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims.

Claims

1. An organic light emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an emission layer disposed between the first electrode and the second electrode, wherein the emitting layer comprises a host and a thermally activated delayed fluorescent emitter, and The host includes at least one compound selected from the group consisting of a compound represented by Formula 1 and a compound represented by Formula 2, and CZ in Formulas 1 and 2 is a group represented by Formula CZ1 or CZ2: Wherein, in Formula 1, CZ1, and CZ2, rings A1, A2, A5, and A6 are each independently a phenyl group or a naphthalene group, In Formula 2, Ring A5 is a benzene group or a naphthyl group, and Ring A6 is a dibenzofuran group or a dibenzothiophene group, In formulas 1, 2, CZ1, and CZ2, X 22 is O or S, m is 0, n is 0 or 1, Z1-Z7 are each independently: Hydrogen, deuterium, or cyano (CN); or Each is unsubstituted or substituted by at least one C1-C 20 Alkyl, phenyl, biphenyl, or terphenyl: deuterium, cyano, and C1-C 20 alkyl, b1-b6 are each independently 0, 1, 2, or 3, * indicates the binding site with the adjacent atom, and The compound represented by Formula 1 and the compound represented by Formula 2 each include at least one cyano group, The thermally activated delayed fluorescent emitter includes a compound represented by Formula 11-7: Among them, in formula 11-7, X1 is a single bond, L3 are each independently selected from: phenylene, naphthylene, and fluorenylene; and phenylene, naphthylene, and fluorenylene, each of which is substituted by at least one selected from the group consisting of deuterium, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and fluorenyl, c3 is 1 or 2, R1 and R2 are each independently selected from hydrogen, deuterium, C1-C 10 Alkyl, C1-C 10 alkoxy, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, a14 and a24 are each independently an integer of 0-4, R3 is a group represented by formula 13-8: In formula 13-8, L 11 Each independently selected from: phenylene, naphthylene, and fluorenylene; and phenylene, naphthylene, and fluorenylene, each of which is substituted by at least one selected from the group consisting of deuterium, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and fluorenyl, a11 is 1, R 11 are each independently selected from hydrogen, deuterium, C1-C 10 Alkyl, and C1-C 10 Alkoxy, and d12 is an integer greater than 0 and less than or equal to 2, The emissive layer does not include an organometallic compound containing a transition metal, and A delayed fluorescence component emitted from the thermally activated delayed fluorescence emitter is 20% or more based on a total emission component emitted from the emission layer.

2. The organic light emitting device according to claim 1, wherein Z1-Z7 are each independently: hydrogen, deuterium, or cyano; or Each is unsubstituted or substituted by at least one C3-C 10 Alkyl, phenyl, biphenyl, or terphenyl: deuterium, cyano, and C3-C 10 alkyl.

3. The organic light emitting device according to claim 1, wherein The number of cyano groups included in the compound represented by Formula 1 and the number of cyano groups included in the compound represented by Formula 2 are each independently 1, 2, 3, or 4.

4. The organic light emitting device according to claim 1, wherein: In equations 1 and 2, At least one selected from the group Z1 having a number b1 and the group Z2 having a number b2 is a cyano group, At least one of the groups Z3 selected from the group b3 is a cyano group, At least one selected from the group Z5 having a number b5 and the group Z6 having a number b6 is a cyano group, At least one of the groups Z1 selected from the number b1 and the groups Z2 selected from the number b2 is a cyano group, and at least one of the groups Z3 selected from the number b3 is a cyano group, At least one selected from the group Z1 in number b1 and the group Z2 in number b2 is a cyano group, and at least one selected from the group Z5 in number b5 and the group Z6 in number b6 is a cyano group, At least one of the groups Z3 selected from the number b3 is a cyano group, and at least one of the groups Z5 selected from the number b5 and the number b6 is a cyano group, or At least one selected from the number b1 of groups Z1 and the number b2 of groups Z2 is a cyano group, at least one selected from the number b3 of groups Z3 is a cyano group, and at least one selected from the number b5 of groups Z5 and the number b6 of groups Z6 is a cyano group.

5. The organic light emitting device according to claim 1, wherein CZ in Formulae 1 and 2 is a group represented by the formula CZ2, Z7 in formula CZ2 is a C1-C 20 Alkyl, phenyl, biphenyl, or terphenyl.

6. The organic light emitting device according to claim 1, wherein In formula 1 and 2, The group represented by is one selected from formulae O1 to O16, M1 to M16, and P1 to P9: in, In O1 to O16, M1 to M16, and P1 to P9, Z 15 , Z 16 , Z 18 and Z 19 Each independently is: hydrogen, deuterium, or cyano; or Each is unsubstituted or substituted by at least one C1-C 20 Alkyl, phenyl, biphenyl, and terphenyl: deuterium, cyano, and C1-C 20 Alkyl, and * and *' each represent a binding site with an adjacent atom.

7. The organic light emitting device according to claim 1, wherein In formula 1, The group represented by is selected from the groups represented by formulae 1(1) to 1(4), In formula 2, The group represented by is selected from the groups represented by formulae 2(1) to 2(12), The group represented by the formula CZ1 is selected from the groups represented by the formulae CZ1(1) to CZ1(3), and The group represented by formula CZ2 is selected from the group represented by formulas CZ2(1) to CZ2(14): in, In Formulas 1(1) to 1(4), 2(1) to 2(12), CZ1(1) to CZ1(3), and CZ2(1) to CZ2(14), X 22 , Z1, Z2, Z5-Z7, b5, and b6 are each independently the same as described in claim 1, and * represents a binding site with an adjacent atom.

8. The organic light emitting device according to claim 1, wherein The host comprises at least one compound selected from compounds H1 to H21, and H24 to H28:

9. The organic light emitting device according to claim 1, wherein The difference between the singlet energy level of the thermally activated delayed fluorescent emitter in electron volts and the triplet energy level of the thermally activated delayed fluorescent emitter in electron volts is in the range of 0 electron volts to 0.5 electron volts, and The singlet energy level and the triplet energy level were evaluated by a density functional theory method using structure optimization at the level of B3LYP / 6-31G(d,p).

10. The organic light-emitting device according to claim 1, wherein the thermally activated delayed fluorescence emitter is compound D205:

11. The organic light emitting device according to claim 1, wherein A delayed fluorescence component emitted from the thermally activated delayed fluorescence emitter is 26.7% or more based on total emission components emitted from the emission layer.

12. The organic light emitting device according to claim 1, wherein The light emitted from the thermally activated delayed fluorescent emitter in the emitting layer is blue light.

13. The organic light emitting device according to claim 1, wherein The amount of the thermally activated delayed fluorescent emitter is in the range of 0.01 parts by weight to 30 parts by weight based on 100 parts by weight of the host.

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