Azido compound, composition, organic light-emitting device and manufacturing method of organic light-emitting device

Abstract

Provided are an azide-based compound, a composition including the azide-based compound, an organic light-emitting device including the azide-based compound, and a method of manufacturing the organic light-emitting device. The organic light emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode and including an emission layer; and an azide compound represented by Formula 1.

Description

[0001] This application is a divisional application of a patent application with an application date of December 19, 2019, application number 201911314124.6, and invention name “Azide compounds, compositions, organic light-emitting devices and manufacturing methods thereof”. Technical Field

[0002] Exemplary embodiments of the invention generally relate to an azide-based compound, an organic light-emitting device including the azide-based compound, and a method of manufacturing the organic light-emitting device. Background Art

[0003] Organic light-emitting devices are self-emissive devices that produce full-color images, and also have wide viewing angles, high contrast, short response times, and excellent characteristics in brightness, driving voltage, and response speed compared to devices in the art.

[0004] Examples of such organic light-emitting devices may include a first electrode located on a substrate, and a hole transport region, an emissive layer, an electron transport region, and a second electrode located sequentially on the first electrode. Holes provided from the first electrode can move toward the emissive layer through the hole transport region, and electrons provided from the second electrode can move toward the emissive layer through the electron transport region. Carriers such as holes and electrons recombine in the emissive layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.

[0005] The above information disclosed in this Background section is only for understanding the background of the inventive concept and therefore it may contain information that does not constitute the prior art. Summary of the Invention

[0006] One or more embodiments of the present disclosure include an azide-based compound, an organic light-emitting device including the azide-based compound, and a method of manufacturing the organic light-emitting device.

[0007] Additional features of the inventive concepts will be set forth in the description which follows, and in part will be apparent from the description, or may be learned by practice of the inventive concepts.

[0008] In one aspect, an azide compound represented by Formula 1 is provided:

[0009] <Formula 1>

[0010]

[0011] In formula 1,

[0012] L1 to L3 and L 11 and L 12 Each of them may be independently a single bond or a substituted or unsubstituted C1-C 10 Alkylene,

[0013] a1 to a3 and a11 and a12 may each independently be an integer from 1 to 5, wherein when a1 is two or more, two or more L1s may be the same or different from each other, when a2 is two or more, two or more L2s may be the same or different from each other, when a3 is two or more, two or more L3s may be the same or different from each other, and when a11 is two or more, two or more L 11 They may be the same or different from each other. When a12 is two or more, two or more L 12 can be the same as or different from each other,

[0014] b1 and b2 can each independently be an integer of 1 or 2,

[0015] b3 can be an integer of 0 or 1.

[0016] When b3 is 0, *-((L3) a3 -N3) b3 It can be hydrogen,

[0017] When b1 is 2, two *-((L1) a1 -N3) can be the same or different from each other. When b2 is two, the two *-((L2) a2 -N3) may be the same as or different from each other,

[0018] * indicates the binding site with the adjacent atom,

[0019] Substituted C1-C 10 At least one substituent in the alkylene group may be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 Alkoxy.

[0020] Another aspect provides a composition comprising: the azide compound described above; a polymer represented by Formula 2; and a solvent:

[0021] <Formula 2>

[0022]

[0023] In formula 2,

[0024] Ar1 to Ar3 may each independently be a substituted or unsubstituted C3-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,

[0025] c1 and c2 can each independently be an integer from 1 to 3,

[0026] n can be an integer from 70 to 400,

[0027] Substituted C3-C 60 Carbocyclic and substituted C1-C 60 At least one substituent in the heterocyclic group may be selected from:

[0028] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0029] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0030] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;

[0031] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0032] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31)、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0033] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

[0034] Another aspect provides an organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an organic layer located between the first electrode and the second electrode and including an emission layer; and an azide compound.

[0035] Another aspect provides a method for manufacturing an organic light-emitting device, the method comprising forming a hole transport region on a first electrode,

[0036] The formation of the hole transport region includes a solution process using the composition described above.

[0037] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] The accompanying drawings illustrate exemplary embodiments of the invention and, together with the description, serve to explain the inventive concept, wherein the accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification. In the drawings:

[0039] Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment;

[0040] Figure 2is a schematic diagram of an organic light emitting device according to another embodiment;

[0041] Figure 3 is a schematic diagram of an organic light emitting device according to another embodiment; and

[0042] Figure 4 is a schematic diagram of an organic light emitting device according to another embodiment. DETAILED DESCRIPTION

[0043] In the following description, for the purpose of illustration, many specific details are set forth to provide a thorough understanding of the various exemplary embodiments or implementations of the invention. As used herein, "embodiment" and "implementation" are interchangeable words that are non-limiting examples of devices or methods employing one or more inventive concepts disclosed herein. However, it is apparent that the various exemplary embodiments may be implemented without these specific details or in the presence of one or more equivalent arrangements. In other cases, in order to avoid making the various exemplary embodiments unnecessarily obscure, well-known structures and devices are shown in block diagram form. In addition, the various exemplary embodiments may be different, but need not be exclusive. For example, without departing from the inventive concept, the specific shape, construction, and characteristics of the exemplary embodiment may be used or implemented in another exemplary embodiment.

[0044] Unless otherwise stated, the exemplary embodiments shown will be understood as providing exemplary features of different details of some ways in which the inventive concept can be implemented in practice. Therefore, unless otherwise stated, the features, components, modules, layers, films, panels, regions and / or aspects of the various embodiments (hereinafter, individually or collectively referred to as "elements") can be further combined, separated, interchanged and / or rearranged without departing from the inventive concept.

[0045] The use of cross hatching and / or shading is generally provided in the accompanying drawings to make the boundaries between adjacent elements clear. Thus, unless otherwise specified, the presence and absence of cross hatching or shading do not express or indicate any preference or requirement for the specific material, material properties, size, ratio, commonality between the elements shown and / or any other characteristics, attributes, properties, etc. of the elements. In addition, in the accompanying drawings, the size and relative size of the elements can be exaggerated for clarity and / or descriptive purposes. When the exemplary embodiment can be implemented differently, the specific process sequence can be performed in a different order than described. For example, two processes described in succession can be performed substantially simultaneously or in an order opposite to the described order. In addition, the same reference numerals represent the same elements.

[0046] When an element or layer is referred to as being "on" another element or layer, "connected to" or "bound to" another element or layer, the element or layer may be directly on, directly connected to or directly bound to the other element or layer, or there may be an intermediate element or layer. However, when an element or layer is referred to as being "directly on" another element or layer, "directly connected to" or "directly bound to" another element or layer, there are no intermediate elements or layers. For this purpose, the term "connected" may refer to a physical connection, electrical connection and / or fluid connection with or without an intermediate element. In addition, the D1 axis, the D2 axis and the D3 axis are not limited to the three axes of a rectangular coordinate system (such as the x-axis, the y-axis and the z-axis), but may be interpreted in a broader sense. For example, the D1 axis, the D2 axis and the D3 axis may be perpendicular to each other, or may represent different directions that are not perpendicular to each other. For the purposes of this disclosure, "at least one of X, Y, and Z" and "at least one selected from the group consisting of X, Y, and Z" may be understood as X only, Y only, Z only, or any combination of two or more of X, Y, and Z, such as, for example, XYZ, XYY, YZ, and ZZ. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0047] Although the terms "first," "second," etc. may be used herein to describe various types of elements, these elements should not be limited by these terms. These terms are used to distinguish one element from another. Thus, the first element discussed below could be named a second element without departing from the disclosed teachings.

[0048] For descriptive purposes, spatially relative terms such as "under," "beneath," "beneath," "down," "over," "up," "above," "higher," "side" (e.g., as in "sidewall"), etc., may be used herein to describe the relationship of one element to another (other) element as shown in the accompanying drawings. Spatially relative terms are intended to encompass different orientations of the device in use, operation, and / or manufacture in addition to the orientation depicted in the accompanying drawings. For example, if the device in the drawings is turned over, elements or features described as "under" or "beneath" other elements or features would subsequently be positioned "over" the other elements or features. Thus, the exemplary term "under" can include both above and below orientations. Furthermore, the device can be positioned otherwise (e.g., rotated 90 degrees or at other orientations), and as such, the spatially relative descriptors used herein should be interpreted accordingly.

[0049] The terms used herein are for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, unless the context clearly indicates otherwise, the singular forms "one", "a(kind / person)" and "the(s)" are also intended to include plural forms. In addition, when the terms "comprise" and / or "include" and their variations are used in this specification, the features, integral bodies, steps, operations, elements, components and / or their groups stated are indicated, but the presence or addition of one or more other features, integral bodies, steps, operations, elements, components and / or their groups is not excluded. It should also be noted that, as used herein, the terms "substantially", "approximately" and other similar terms are used as approximate terms rather than as terms of degree, and as such, they are used to explain the inherent deviations of measured values, calculated values and / or provided values that will be recognized by those of ordinary skill in the art.

[0050] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure is a part. Terms (such as those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless so explicitly defined herein.

[0051] Azide compounds are represented by formula 1:

[0052] <Formula 1>

[0053]

[0054] In formula 1,

[0055] L1 to L3 and L 11 and L 12 Each of them may be independently a single bond or a substituted or unsubstituted C1-C 10 Alkylene.

[0056] In one embodiment, L1 to L3 may each independently be a single bond.

[0057] In one embodiment, L 11 and L 12 Can be independently selected from:

[0058] single bonds, methylene, ethylene, propylene, butylene, and pentylene; and

[0059] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone and C1-C 10 At least one selected from the group consisting of methylene, ethylene, propylene, butylene and pentylene among the alkyl groups.

[0060] For example, *-(L 11 ) a11 -*' and *-(L 12 ) a12 -*' may be identical to each other, but the embodiments of the present disclosure are not limited thereto.

[0061] In Formula 1, a1 to a3 and a11 and a12 may each independently be an integer of 1 to 5, wherein when a1 is 2 or greater, two or more L1s may be the same as or different from each other, when a2 is 2 or greater, two or more L2s may be the same as or different from each other, when a3 is 2 or greater, two or more L3s may be the same as or different from each other, and when a11 is 2 or greater, two or more L 11 can be the same as or different from each other, and when a12 is two or more, two or more L 12 They may be the same as or different from each other.

[0062] For example, a1 to a3 may each independently be 1, and L1 to L3 may each independently be a single bond.

[0063] For example, a11 and a12 may each independently be an integer from 1 to 3.

[0064] For example, a11 and a12 may each independently be an integer from 1 to 3, and L 11 and L 12 Each may be independently selected from methylene, ethylene and propylene.

[0065] In Formula 1, b1 and b2 can each independently be an integer of 1 or 2,

[0066] b3 can be an integer of 0 or 1.

[0067] When b3 is 0, *-((L3) a3 -N3) may be hydrogen, and

[0068] When b1 is 2, two *-((L1) a1 -N3) can be the same as or different from each other, and when b2 is two, the two *-((L2) a2 -N3) can be the same as or different from each other.

[0069] In one embodiment, the sum of b1, b2, and b3 may be 2 to 5.

[0070] In formula 1, * represents the binding site with the adjacent atom, and the substituted C1-C 10 At least one substituent in the alkylene group may be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 Alkoxy.

[0071] For example, the azide compound may have a molecular weight of about 100 g / mol to about 2000 g / mol.

[0072] In one or more embodiments, the azide compound can be represented by Formula 1-1:

[0073] <Formula 1-1>

[0074]

[0075] In formula 1-1,

[0076] b1 to b3 may each independently be the same as defined in conjunction with b1 to b3 in Formula 1, and

[0077] Z1 to Z8 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 Alkoxy.

[0078] In one embodiment, the azide compound can be selected from Compound 1 to Compound 3, but the embodiments of the present disclosure are not limited thereto:

[0079]

[0080] In azide-based compounds, since the main chain is composed of alkyl groups, thermal and photocrosslinking can be well performed without destroying the conjugation that is the main feature of the hole-transporting region.

[0081] In addition, the azide compound includes two or more azide groups as cross-linking groups, thereby exhibiting more excellent cross-linking properties.

[0082] Therefore, electronic devices (e.g., organic light-emitting devices) including the azide compound represented by Formula 1 can exhibit low driving voltage and high efficiency. When the azide compound represented by Formula 1 is used, an organic light-emitting device manufactured by an inkjet process and improved in driving voltage and efficiency can be provided.

[0083] The synthesis method of the azide compound represented by Formula 1 will be apparent to those skilled in the art by referring to the following examples.

[0084] Another exemplary embodiment provides a composition comprising:

[0085] An azide compound represented by Formula 1;

[0086] a polymer compound represented by Formula 2; and

[0087] Solvent:

[0088] <Formula 2>

[0089]

[0090] In formula 2,

[0091] Ar1 to Ar3 may each independently be a substituted or unsubstituted C3-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 Heterocyclic group.

[0092] In an exemplary embodiment, Ar1 to Ar3 may each be independently selected from:

[0093] phenyl, naphthyl, fluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0094] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl 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 indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group.

[0095] In Formula 2, c1 and c2 may each independently be an integer from 1 to 3, and n may be an integer from 70 to 400,

[0096] Substituted C3-C 60 Carbocyclic and substituted C1-C 60 At least one substituent in the heterocyclic group may be selected from:

[0097] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0098] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0099] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;

[0100] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0101] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q31 )(Q 32 ),and

[0102] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

[0103] In one exemplary embodiment, the polymer compound represented by Formula 2 may include at least one selected from Compound 101 to Compound 103:

[0104]

[0105] In one exemplary embodiment, the polymer compound may have a molecular weight of about 5000 g / mol or greater, and the azide compound may have a molecular weight of about 2000 g / mol or less.

[0106] For example, the polymer compound may have a molecular weight in the range of about 5,000 g / mol to about 100,000 g / mol, for example, in the range of about 10,000 g / mol to about 100,000 g / mol, for example, in the range of about 25,000 g / mol to about 100,000 g / mol, but exemplary embodiments of the present disclosure are not limited thereto.

[0107] For example, the azide compound may have a molecular weight in the range of about 100 g / mol to about 2000 g / mol, for example, in the range of about 100 g / mol to about 1000 g / mol, for example, in the range of about 250 g / mol to about 1000 g / mol, but exemplary embodiments of the present disclosure are not limited thereto.

[0108] In one exemplary embodiment, the composition may include the azide compound in an amount ranging from about 0.1 parts by weight to about 10 parts by weight and the polymer compound in an amount ranging from about 90 parts by weight to about 99 parts by weight, based on 100 parts by weight of the composition excluding the solvent.

[0109] In one exemplary embodiment, the solvent may be a compound represented by Formula 8:

[0110] <Formula 8>

[0111]

[0112] In formula 8,

[0113] X 81 may be selected from a single bond, -O-, -S-, -C(=O)-, -C(=O)O- and -C(=O)NH-,

[0114] R 81 and R 82 Can be independently selected from:

[0115] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, -Si(Q 31 )(Q 32 )(Q 33 ), C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, phenanthrenyl, pyrenyl, carbazolyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl; and

[0116] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, -Si(Q 81 )(Q 82 )(Q 83 ), methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, C1-C 10 a C1-C1 residue selected from at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthrenyl group, a pyrenyl group, a carbazolyl group, a carbazolyl group substituted with a phenyl group, a dibenzofuranyl group, a benzonaphthofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group; 10 Alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, phenanthrenyl, pyrenyl, carbazolyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl,

[0117] b 81 can be an integer from 1 to 5, and

[0118] Q 81 To Q 83 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C6-C 60 Aryl, substituted with C1-C 60 Alkyl C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

[0119] For example, the solvent may be methyl benzoate, but is not limited thereto.

[0120] At least one of the azide compounds of Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the azide compound can be included in an emission layer. In one or more exemplary embodiments, the azide compound represented by Formula 1 can be used as a material for forming a cap layer located outside the pair of electrodes of the organic light-emitting device.

[0121] Therefore, an organic light-emitting device is provided, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and at least one azide compound represented by Formula 1.

[0122] For example, the organic layer may include only Compound 1 as an azide compound. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In one or more exemplary embodiments, the organic layer may include Compound 1 and Compound 2 as azide compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the emission layer), or in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the hole transport layer).

[0123] In one exemplary embodiment, the first electrode of the organic light emitting device may be an anode.

[0124] The second electrode of the organic light emitting device may be a cathode,

[0125] The organic layer may include at least one azide-based compound represented by Formula 1, and may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode.

[0126] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and

[0127] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0128] In one or more exemplary embodiments, the hole transport region may include an azide-based compound represented by Formula 1.

[0129] In one exemplary embodiment, the hole transport region may further include a polymer having a molecular weight of 5000 g / mol or more.

[0130] In one exemplary embodiment, the emissive layer may include a host material and a dopant material, and

[0131] The dopant material may include a phosphorescent dopant or a fluorescent dopant.

[0132] In one exemplary embodiment, the emitting layer may be a first emitting layer for emitting light of a first color,

[0133] The organic light emitting device may further include, between the first electrode and the second electrode: i) at least one second emission layer for emitting second color light, or ii) at least one third emission layer for emitting third color light,

[0134] The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light may be the same as or different from each other, and

[0135] The first color light and the second color light may be emitted in the form of mixed light, or the first color light, the second color light, and the third color light may be emitted in the form of mixed light.

[0136] As used herein, the term "organic layer" refers to a single layer and / or a plurality of layers located between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0137] For example, the organic light-emitting device may have: i) a stacked structure comprising a first electrode, an organic layer, a second electrode, and a second covering layer stacked sequentially in the order of the statement; ii) a stacked structure comprising a first covering layer, a first electrode, an organic layer, a second electrode, and a second covering layer stacked sequentially in the order of the statement; or iii) a stacked structure comprising a first covering layer, a first electrode, an organic layer, a second electrode, and a second covering layer stacked sequentially in the order of the statement, and at least one selected from the first covering layer and the second covering layer may include an azide compound.

[0138] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an exemplary embodiment. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0139] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to exemplary embodiments are described.

[0140] exist Figure 1 In the embodiment, a substrate may be additionally provided below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface flatness, ease of handling, and waterproofness.

[0141] The first electrode 110 may be formed by depositing or sputtering a material on a substrate for forming the first electrode 110. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0142] 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, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the exemplary embodiments of the present disclosure are not limited thereto. In one or more exemplary embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the exemplary embodiments of the present disclosure are not limited thereto.

[0143] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0144] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

[0145] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .

[0146] The hole transport region in the organic layer 150 may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0147] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.

[0148] For example, the hole transport region may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer containing a plurality of different materials, and the multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.

[0149] The hole transport region may include at least one selected from 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 / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0150]

[0151] <Formula 201>

[0152]

[0153] <Formula 202>

[0154]

[0155] In Equations 201 and 202,

[0156] L 201 To L 204 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0157] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 Alkenylene, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0158] xa1 to xa4 may each independently be an integer from 0 to 3,

[0159] xa5 can be an integer from 1 to 10, and

[0160] R 201 to R 204 and Q 201 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60Arylthio, substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0161] For example, in Equation 202, R 201 and R 202 R may alternatively be linked via a single bond, dimethyl-methylene or diphenyl-methylene. 203 and R 204 Attachment may alternatively be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0162] In one or more exemplary embodiments, in Equation 201 and Equation 202,

[0163] L 201 To L 205 Can be independently selected from:

[0164] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanth ... phenylene, tetraphenylene, perylenene, pentaphenylene, hexaphenylene, pentaphenylene, rubinylene, camphenylene, ovophene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, and pyridylene; and

[0165] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, -Si(Q31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from the group consisting of phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinylene, camphenylene, ovophene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene and pyridinylene, and

[0166] Q 31 To Q 33 Can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0167] In one or more exemplary embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

[0168] In one or more exemplary embodiments, xa5 may be 1, 2, 3, or 4.

[0169] In one or more exemplary embodiments, R 201 to R 204 and Q 201 Can be independently selected from:

[0170] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetracene, perylenyl, pentaphenyl, hexacenyl, pentacene, rubinyl, camphenyl, oophenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0171] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetracene, perylenyl, peryl, pentaphenyl, hexacenyl, pentacene, rubinyl, camphenyl, oophenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiorol and pyridyl, and

[0172] Q 31 To Q 33 Same as described above.

[0173] In one or more exemplary embodiments, in Formula 201, from R 201 to R 203 At least one of the selected ones can be independently selected from:

[0174] Fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0175] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10phenyl of an alkyl group, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, but exemplary embodiments of the present disclosure are not limited thereto.

[0176] In one or more exemplary embodiments, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.

[0177] In one or more exemplary embodiments, in Equation 202, from R 201 to R 204 At least one of the selected ones may be selected from:

[0178] carbazolyl; and

[0179] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10 A carbazolyl group of at least one selected from among a phenyl group of an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but exemplary embodiments of the present disclosure are not limited thereto.

[0180] The compound represented by Formula 201 can be represented by Formula 201A:

[0181] <Formula 201A>

[0182]

[0183] In one exemplary embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but exemplary embodiments of the present disclosure are not limited thereto:

[0184] <Formula 201A(1)>

[0185]

[0186] In one exemplary embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but exemplary embodiments of the present disclosure are not limited thereto:

[0187] <Formula 201A-1>

[0188]

[0189] In one exemplary embodiment, the compound represented by Formula 202 may be represented by Formula 202A:

[0190] <Formula 202A>

[0191]

[0192] In one exemplary embodiment, the compound represented by Formula 202 may be represented by Formula 202A-1:

[0193] <Formula 202A-1>

[0194]

[0195] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,

[0196] L 201 To L 203 , xa1 to xa3, xa5 and R 202 to R 204 Same as described above,

[0197] R 211 and R 212 Can independently bind to R 203 are defined identically, and

[0198] R 213 to R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, and pyridyl.

[0199] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but exemplary embodiments of the present disclosure are not limited thereto:

[0200]

[0201]

[0202]

[0203] The thickness of the hole transport region can be approximately to approximately In the range of, for example, about to approximately When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to approximately In the range of, for example, about to approximately In the range of to approximately In the range of, for example, about to approximately 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 can be obtained without significantly increasing the driving voltage.

[0204] The emission assisting layer can improve luminous efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer can include the materials described above.

[0205] In addition to these materials, the hole transport region may also include a charge generating material for improving the conductive properties. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0206] The charge generating material may be, for example, a p-dopant.

[0207] In one exemplary embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of approximately −3.5 eV or less.

[0208] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but exemplary embodiments of the present disclosure are not limited thereto.

[0209] For example, the p-dopant may include at least one selected from the following compounds:

[0210] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0211] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0212] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0213] A compound represented by the following formula 221:

[0214]

[0215] <Formula 221>

[0216]

[0217] But exemplary embodiments of the present disclosure are not limited thereto.

[0218] In formula 221,

[0219] R 221 to R 223 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, provided that R 221 to R 223 At least one selected from cyano, -F, -Cl, -Br, -I, C1-C substituted with -F 20 Alkyl, C1-C substituted with -Cl 20 Alkyl, C1-C substituted with -Br 20 Alkyl and C1-C substituted with -I 20 At least one substituent selected from the group consisting of:

[0220] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer in the organic layer 150 can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more exemplary embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more exemplary embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0221] The emission layer may include an azide-based compound represented by Formula 1.

[0222] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0223] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but exemplary embodiments of the present disclosure are not limited thereto.

[0224] The thickness of the emission layer can be approximately to approximately In the range of, for example, about to approximately When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0225] The host in the emission layer may include an azide-based compound represented by Formula 1.

[0226] In one or more exemplary embodiments, the host may further include a compound represented by the following Formula 301:

[0227] <Formula 301>

[0228] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0229] In formula 301,

[0230] Ar 301 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,

[0231] xb11 can be 1, 2 or 3,

[0232] L 301 Can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0233] xb1 can be an integer from 0 to 5,

[0234] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 ),-C(=O)(Q 301 )、-S(=O)2(Q 301 ) and -P(=O)(Q 301 )(Q 302 ),

[0235] xb21 can be an integer from 1 to 5, and

[0236] Q 301 To Q 303 Can be independently selected from C1-C 10 Alkyl, C1-C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but exemplary embodiments of the present disclosure are not limited thereto.

[0237] In one exemplary embodiment, Ar in Formula 301 301 Can be selected from:

[0238] Naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, perylenyl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0239] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, perylenyl, perylenyl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, and

[0240] Q 31 To Q 33 Can be independently selected from C1-C 10 Alkyl, C1-C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but exemplary embodiments of the present disclosure are not limited thereto.

[0241] In Formula 301, when xb11 is two or greater, two or more Ar 301 Can connect via one-touch.

[0242] In one or more exemplary embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:

[0243] <Formula 301-1>

[0244]

[0245] <Formula 301-2>

[0246]

[0247] In Formula 301-1 and Formula 301-2,

[0248] A 301 To A 304 can be independently selected from benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene,

[0249] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0250] R 311 to R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0251] xb22 and xb23 can each independently be 0, 1 or 2,

[0252] L301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0253] L 302 To L 304 Can be independently combined with L 301 The same definition,

[0254] xb2 to xb4 may each independently be the same as defined in conjunction with xb1, and

[0255] R 302 to R 304 Can independently bind to R 301 The same definition.

[0256] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:

[0257] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanthrenylene phenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofurylene, benzothiophenylene, dibenzofurylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and

[0258] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, pyrenylene phenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofurylene, benzothiophenylene, dibenzofurylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene, and

[0259] Q 31 To Q 33 Same as described above.

[0260] In one exemplary embodiment, in Equation 301, Equation 301-1, and Equation 301-2, R 301 to R 304Can be independently selected from:

[0261] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0262] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32) is at least one selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and

[0263] Q 31 To Q 33 Same as described above.

[0264] In one or more exemplary embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0265] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), and compounds H1 to H55, but exemplary embodiments of the present disclosure are not limited thereto.

[0266]

[0267]

[0268]

[0269] The phosphorescent dopant included in the emission layer of the organic layer 150 may include an organic metal complex represented by Formula 401 described below.

[0270] Formula 401

[0271] M(L 401 ) xc1 (L 402 )xc2

[0272] Formula 402

[0273]

[0274] In Equations 401 and 402,

[0275] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),

[0276] L 401 can be selected from the ligands represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is two or greater, two or more L 401 can be the same as or different from each other,

[0277] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more, two or more L 402 can be the same as or different from each other,

[0278] X 401 To X 404 may each independently be nitrogen or carbon,

[0279] X 401 and X 403 Can be connected via single or double bonds, X 402 and X 404 Can be connected via single or double bonds,

[0280] A 401 and A 402 Can be independently selected from C5-C 60 Carbocyclic or C1-C 60 heterocyclic group,

[0281] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' or *=C=*', where Q 411 and Q 412 can be independently hydrogen, deuterium, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl or naphthyl, X 406 Can be a single bond, O or S,

[0282] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 ),-C(=O)(Q 401 )、-S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 Can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 heteroaryl,

[0283] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0284] * and *' in Formula 402 both represent the binding sites with M in Formula 401.

[0285] In one exemplary embodiment, A in equation 402 401 and A 402Each of the radicals may be independently selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl.

[0286] In one or more exemplary embodiments, in equation 402, i) X 401 Can be nitrogen, X 402 Can be carbon, or ii) X 401 and X 402 They may both be nitrogen.

[0287] In one or more exemplary embodiments, R in equation 402 401 and R 402 Can be independently selected from:

[0288] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 alkoxy;

[0289] C1-C12 substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl 20 Alkyl and C1-C 20 alkoxy;

[0290] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;

[0291] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20at least one selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0292] -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 ),-C(=O)(Q 401 )、-S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ),and

[0293] Q 401 To Q 403 Can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl and naphthyl, but not limited thereto.

[0294] In one or more exemplary embodiments, when xc1 in equation 401 is two or greater, two or more L 401 Two A's 401 It can be optionally connected via X as a linker 407 Connect, or two or more L 401 Two A's 402 It can be optionally connected via X as a linker 408 Connection (see Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 Each of them may be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414can be independently hydrogen, deuterium, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but exemplary embodiments of the present disclosure are not limited thereto.

[0295] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. For example, L 402 It can be selected from halogen, diketone (e.g., acetylacetone (compound)), carboxylic acid (e.g., picolinic acid (salt)), -C(=O)-, isonitrile, -CN and phosphorus-containing materials (e.g., phosphine or phosphorous acid (salt)), but exemplary embodiments of the present disclosure are not limited thereto.

[0296] In one or more exemplary embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD26, but exemplary embodiments of the present disclosure are not limited thereto:

[0297]

[0298]

[0299] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0300] The fluorescent dopant may include a compound represented by the following Formula 501:

[0301] <Formula 501>

[0302]

[0303] In formula 501,

[0304] Ar 501 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,

[0305] L 501 To L 503 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0306] xd1 to xd3 may each independently be an integer from 0 to 3,

[0307] R 501 and R 502 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

[0308] xd4 can be an integer from 1 to 6.

[0309] In one exemplary embodiment, Ar in Formula 501 501 Can be selected from:

[0310] naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0311] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 At least one selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl and indenophenanthrenyl.

[0312] In one or more exemplary embodiments, L in Equation 501 501 To L 503 Can be independently selected from:

[0313] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanthrenylene phenylene, benzothiophene, benzofuranylene, dibenzofuranylene, dibenzothiophene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioxylene, and pyridylene; and

[0314] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene radical, a naphthylene radical, a fluorenyl radical, a spirobifluorenyl radical, a benzofluorenyl radical, a dibenzofluorenyl radical, a phenanthrenyl radical, an anthracene radical, a fluoranthenyl radical, a benzo[9,10]phenanthrenyl radical, a pyrenyl radical, ... phenylene, benzothiophene, benzofuranylene, dibenzofuranylene, dibenzothiophene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioxylene, and pyridylene.

[0315] In one or more exemplary embodiments, R in Equation 501 501 and R 502 Can be independently selected from:

[0316] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl; and

[0317] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiorol and pyridyl, and

[0318] Q 31 To Q 33 Can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0319] In one or more exemplary embodiments, xd4 in Formula 501 may be 2, but exemplary embodiments of the present disclosure are not limited thereto.

[0320] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:

[0321]

[0322]

[0323]

[0324] In one or more exemplary embodiments, the fluorescent dopant may be selected from the following compounds, but exemplary embodiments of the present disclosure are not limited thereto.

[0325]

[0326] The electron transport region in the organic layer 150 may have: i) a single layer structure having a single layer including a single material; ii) a single layer structure having a single layer including multiple different materials; or iii) a multilayer structure having multiple layers including multiple different materials.

[0327] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but exemplary embodiments of the present disclosure are not limited thereto.

[0328] 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, wherein for each structure, the constituent layers are sequentially stacked in the order of the description from the emission layer. However, exemplary embodiments of the structure of the electron transport region are not limited thereto.

[0329] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-depleted nitrogen-containing ring.

[0330] "π-electron-poor nitrogen-containing ring" means a C1-C2-N3 ... 60 Heterocyclic group.

[0331] For example, the “π-electron-poor nitrogen-containing ring” may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are condensed with each other; or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is condensed with at least one C5-C 60 A carbocyclyl condensed heteropolycyclic group.

[0332] Examples of π-electron-poor nitrogen-containing rings include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0333] For example, the electron transport region may include a compound represented by Formula 601:

[0334] <Formula 601>

[0335] [Ar 601 ] xe11 -[(L601 ) xe1 -R 601 ] xe21 .

[0336] In Equation 601,

[0337] Ar 601 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,

[0338] xe11 can be 1, 2 or 3,

[0339] L 601 can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0340] xe1 can be an integer from 0 to 5,

[0341] R 601 Can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ),-C(=O)(Q 601 )、-S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0342] Q601 To Q 603 Can be independently C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0343] xe21 can be an integer from 1 to 5.

[0344] In one exemplary embodiment, xe11 numbers of Ar 601 and xe21 numbers of R 601 At least one of the may include a π-electron-poor nitrogen-containing ring.

[0345] In one exemplary embodiment, Ar in Formula 601 601 Can be selected from:

[0346] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiazolyl, benzoxazolyl, isobenzoxazolyl, benzodiazolyl, benzophenanthrenyl, benzophenanthrenyl, benzophenanthridin ...

[0347] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzophenone ...

[0348] Q 31 To Q 33 Can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0349] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.

[0350] In one or more exemplary embodiments, Ar in Formula 601 601 It may be anthracene.

[0351] In one or more exemplary embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0352] <Formula 601-1>

[0353]

[0354] In formula 601-1,

[0355] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and from X 614 To X 616 At least one of the selected ones may be N,

[0356] L 611 To L 613 Can be independently combined with L 601 The same definition,

[0357] xe611 to xe613 can each independently be the same as defined in conjunction with xe1,

[0358] R611 to R 613 Can independently bind to R 601 are defined identically, and

[0359] R 614 to R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0360] In one exemplary embodiment, L in Equation 601 601 and L in formula 601-1 611 To L 613 Can be independently selected from:

[0361] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanthrenylene phenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofurylene, benzothiophenylene, dibenzofurylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and

[0362] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazine at least one selected from the group consisting of phenylene, naphthylene, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofurylene, benzothiophenylene, dibenzofurylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene,

[0363] But exemplary embodiments of the present disclosure are not limited thereto.

[0364] In one or more exemplary embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.

[0365] In one or more exemplary embodiments, R in Equation 601 601 and R in formula 601-1 611 to R 613 Can be independently selected from:

[0366] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0367] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide at least one selected from the group consisting of oxazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0368] -S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and

[0369] Q 601 and Q 602 Same as described above.

[0370] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but exemplary embodiments of the present disclosure are not limited thereto:

[0371]

[0372]

[0373]

[0374]

[0375] In one or more exemplary embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:

[0376]

[0377] The thickness of the buffer layer, hole blocking layer and electron control layer can be about to approximately In the range of, for example, about to approximately When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the electron transport region may have excellent hole blocking properties or electron control properties without significantly increasing the driving voltage.

[0378] The thickness of the electron transport layer can be approximately to approximately In the range of, for example, about to approximately 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 significantly increasing the driving voltage.

[0379] In addition to the materials described above, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.

[0380] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the alkaline earth metal complex may include a metal ion selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but exemplary embodiments of the present disclosure are not limited thereto.

[0381] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or compound ET-D2:

[0382]

[0383] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0384] The electron injection layer may have: i) a single-layer structure having a single layer including a single material; ii) a single-layer structure having a single layer including a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0385] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0386] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one exemplary embodiment, the alkali metal may be Li, Na, or Cs. In one or more exemplary embodiments, the alkali metal may be Li or Cs, but the exemplary embodiments of the present disclosure are not limited thereto.

[0387] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0388] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0389] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0390] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In one exemplary embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the exemplary embodiments of the present disclosure are not limited thereto.

[0391] The alkaline earth metal compound may be selected from alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-x O(0 < x < 1)). In one exemplary embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the exemplary embodiments of the present disclosure are not limited thereto.

[0392] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one exemplary embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the exemplary embodiments of the present disclosure are not limited thereto.

[0393] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include ions of alkali metal, alkaline earth metal and rare earth metal as described above, and the ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but exemplary embodiments of the present disclosure are not limited thereto.

[0394] The electron injection layer can be made up of alkali metal as described above, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof (or include alkali metal as described above, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof). In one or more exemplary embodiments, the electron injection layer can also include organic material. When the electron injection layer also includes organic material, alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0395] The thickness of the electron injection layer can be about to approximately In the range of, for example, about to approximately 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 significantly increasing the driving voltage.

[0396] The second electrode 190 may be provided on the organic layer 150 having such a structure. The second electrode 190 may be a cathode serving as an electron injection electrode. In this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0397] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but exemplary embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0398] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0399] Reference Figures 2 to 4 , Figure 2 The organic light emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 sequentially stacked in the order stated, Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 sequentially stacked in the order stated, Figure 4 The organic light emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the stated order.

[0400] about Figures 2 to 4 , can be combined by reference Figure 1 The description is given to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .

[0401] In the organic layer 150 of each of the organic light-emitting devices 20 and the organic light-emitting device 40, light generated in the emission layer can pass through the first electrode 110 and the first cover layer 210 toward the outside, and the first electrode 110 is a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and the organic light-emitting device 40, light generated in the emission layer can pass through the second electrode 190 and the second cover layer 220 toward the outside, and the second electrode 190 is a semi-transmissive electrode or a transmissive electrode.

[0402] The first capping layer 210 and the second capping layer 220 may improve external light emitting efficiency according to the principle of constructive interference.

[0403] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

[0404] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from a carbocyclic compound, an azide compound, an amine compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the azide compound, and the amine compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one exemplary embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0405] In one exemplary embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0406] In one or more exemplary embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but exemplary embodiments of the present disclosure are not limited thereto.

[0407]

[0408] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the exemplary embodiment is described. However, the exemplary embodiments of the present disclosure are not limited thereto.

[0409] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.

[0410] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature can be set at about 100° C. to about 500° C., about 10 -8 Up to about 10 -3 Torr vacuum and approx. to approximately Vacuum deposition was performed at a deposition rate of 100 Å.

[0411] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and at a heat treatment temperature of about 80°C to about 200°C, taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.

[0412] As used herein, the term "C1-C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C1-C 60 "Alkylene" refers to a C1-C 60 An alkyl group is a divalent group having the same structure.

[0413] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 The term "C2-C4" as used herein is a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, examples of which include ethenyl, propenyl, and butenyl. 60 "Alkenylene" refers to a C2-C 60 Alkenyl is a divalent group having the same structure.

[0414] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The term "C2-C 2-alkyl" as used herein is a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, examples of which include ethynyl and propynyl. 60 "Alkynylidene" refers to a C2-C 60 Alkynyl is a divalent group having the same structure.

[0415] As used herein, the term "C1-C 60 "Alkoxy" refers to a 101 (Among them, A 101 C1-C 60 The monovalent group represented by an alkyl group is exemplified by a methoxy group, an ethoxy group, and an isopropoxy group.

[0416] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a C3-C 10 The cycloalkyl group is a divalent group having the same structure.

[0417] As used herein, the term "C1-C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom and 1 to 10 carbon atoms, examples of which include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkylene" refers to a C1-C 10 The heterocycloalkyl group is a divalent group having the same structure.

[0418] The term "C3-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, examples of which include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a C3-C10 The cycloalkenyl group is a divalent group having the same structure.

[0419] As used herein, the term "C1-C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring. 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkenylene" refers to a C1-C 10 The heterocycloalkenyl group is a divalent group having the same structure.

[0420] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. The term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C6-C 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0421] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. As used herein, the term "C1-C 60 "Heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring atom in addition to 1 to 60 carbon atoms. 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 60 Heteroaryl and C1-C 60 When the heteroarylene group includes two or more rings, the rings may be condensed with each other.

[0422] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C6-C 60Aryl), the term "C6-C 60 "Arylthio" means -SA 103 (Among them, A 103 C6-C 60 aryl).

[0423] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed with each other, having only carbon atoms (e.g., 8 to 60 carbon atoms) as ring atoms, and having no aromaticity in its entire molecular structure. A specific example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0424] As used herein, the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings condensed with each other, at least one heteroatom selected from N, O, Si, P, and S as a ring atom other than carbon atoms (e.g., having 1 to 60 carbon atoms), and having no aromaticity in its entire molecular structure. An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0425] As used herein, the term "C5-C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more exemplary embodiments, the carbonyl group is connected to a C5-C 60 The number of substituents of the carbocyclic group, C5-C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0426] As used herein, the term "C1-C 60 "Heterocyclic group" refers to a group consisting of C5-C 60 The carbocyclic group has a group of the same structure.

[0427] In this specification, substituted C3-C 60 Carbocyclic, substituted C1-C 60 Heterocyclic, substituted C1-C 20 Alkylene, substituted C2-C20 Alkenylene, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocycloalkylene, substituted C3-C 10 Cycloalkenylene, substituted C1-C 10 Heterocycloalkenylene, substituted C6-C 60 Arylene, substituted C1-C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from the group consisting of:

[0428] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0429] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0430] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups;

[0431] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0432] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0433] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.

[0434] 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, and the term "ter-Bu" or "Bu" as used herein refers to an ethyl group. t ” refers to tert-butyl group, and the term “OMe” used herein refers to methoxy group.

[0435] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a group having C6-C 60 A phenyl group substituted with an aryl group as a substituent.

[0436] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" is a group having a C6-C 60 C6-C 60 Phenyl with an aryl group as a substituent.

[0437] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula.

[0438] Another aspect provides a method for manufacturing an organic light-emitting device, the method comprising forming a hole transport region on a first electrode,

[0439] The hole transport region is formed by a solution process using a composition comprising:

[0440] Azide compounds described above;

[0441] a polymer compound represented by Formula 2; and

[0442] Solvent:

[0443] <Formula 2>

[0444]

[0445] In formula 2,

[0446] Ar1 to Ar3 may each independently be a substituted or unsubstituted C3-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,

[0447] c1 and c2 can each independently be an integer from 1 to 3,

[0448] n can be an integer from 70 to 400,

[0449] Substituted C3-C 60 Carbocyclic and substituted C1-C 60 At least one substituent in the heterocyclic group may be selected from:

[0450] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0451] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy;

[0452] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups;

[0453] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0454] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0455] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

[0456] In the method of manufacturing an organic light-emitting device, descriptions of the azide compound, the polymer compound, and the solvent may be the same as described above.

[0457] The solution process can be performed by spin coating, slot coating, dip coating, rod coating, roller coating, gravure coating, micro gravure coating, wire coating, spray coating, inkjet printing, nozzle printing, screen printing, flexographic printing, offset printing, or casting.

[0458] In one exemplary embodiment, the forming of the hole transport region may further include: performing thermal curing or photocuring on the azide compound and the polymer compound; or removing the solvent, and

[0459] The removal of the solvent may be performed at a temperature ranging from about 160°C to about 280°C.

[0460] In one exemplary embodiment, the method of manufacturing an organic light emitting device may further include forming an emission layer on the hole transport region, and

[0461] The formation of the emission layer may include a solution process using a second composition, and the second composition may include a host material, a dopant material, and a second solvent.

[0462] The second solvent in the second composition may be the same as described in conjunction with the solvent, and the host material and the dopant material may be the same as described above.

[0463] Hereinafter, compounds according to exemplary embodiments and organic light-emitting devices according to exemplary embodiments will be described in detail with reference to synthesis examples and examples. The term "using B instead of A" used in describing the synthesis examples means using B instead of A in the same molar equivalent.

[0464] [Example]

[0465] Synthesis Example 1: Synthesis of Compound 1

[0466]

[0467] In nitrogen atmosphere, intermediate A (1.0g, 3.8mmol) and sodium azide (0.6g, 2.4eq.) are added DMF (20mL), and at room temperature stirred 12 hours.After reaction is completed, the mixture thus obtained is passed through silica gel pad, and washed with toluene. Remove solvent from the solution thus obtained, and carry out recrystallization and silica gel chromatography to obtain compound 1 (0.66g, productive rate is 96%).

[0468] MS (MALDI-TOF) m / z: 182 [M] +.

[0469] Synthesis Example 2: Synthesis of Compound 2

[0470]

[0471] Compound 2 (0.63 g, yield 95%) was synthesized in the same manner as in the synthesis of Compound 1, except that Intermediate B was used instead of Intermediate A.

[0472] MS (MALDI-TOF) m / z: 223 [M] +.

[0473] Synthesis Example 3: Synthesis of Compound 3

[0474]

[0475] Compound 3 (0.56 g, yield 91%) was synthesized in the same manner as in the synthesis of Compound 1, except that Intermediate C was used instead of Intermediate A.

[0476] MS (MALDI-TOF) m / z: 305 [M] +.

[0477] Slurry preparation example 1

[0478] The polymer compound 101 and the compound 1 as a low molecular material were mixed at a weight ratio of 9:1, and anisole was used as a solvent to prepare a slurry 1 having a concentration of 1.5%.

[0479] Slurry preparation example 2

[0480] Slurry 2 was prepared in the same manner as in Slurry Preparation Example 1, except that Compound 2 was used instead of Compound 1.

[0481] Slurry preparation example 3

[0482] Slurry 3 was prepared in the same manner as in Slurry Preparation Example 1, except that Compound 3 was used instead of Compound 1.

[0483] Slurry Preparation Example 4

[0484] Slurry 4 was prepared in the same manner as in Slurry Preparation Example 1, except that the polymer compound 102 was used instead of the polymer compound 101 .

[0485] Slurry Preparation Example 5

[0486] Slurry 5 was prepared in the same manner as in Slurry Preparation Example 4, except that Compound 2 was used instead of Compound 1.

[0487] Slurry Preparation Example 6

[0488] Slurry 6 was prepared in the same manner as in Slurry Preparation Example 4, except that Compound 3 was used instead of Compound 1.

[0489] Slurry Preparation Example 7

[0490] Slurry 7 was prepared in the same manner as in Slurry Preparation Example 1, except that the polymer compound 103 was used instead of the polymer compound 101 .

[0491] Slurry Preparation Example 8

[0492] Slurry 8 was prepared in the same manner as in Slurry Preparation Example 7, except that Compound 2 was used instead of Compound 1.

[0493] Slurry Preparation Example 9

[0494] Slurry 9 was prepared in the same manner as in Slurry Preparation Example 7, except that Compound 3 was used instead of Compound 1.

[0495] Comparative Preparation Example 1

[0496] Comparative slurry 1 was prepared in the same manner as in Slurry Preparation Example 1, except that Comparative Compound A was used instead of Compound 1.

[0497]

[0498] <Comparative Compound A>

[0499] Comparative Preparation Example 2

[0500] Comparative slurry 2 was prepared in the same manner as in Slurry Preparation Example 4, except that Comparative Compound A was used instead of Compound 1.

[0501] Comparative Preparation Example 3

[0502] Comparative slurry 3 was prepared in the same manner as in Slurry Preparation Example 7, except that Comparative Compound A was used instead of Compound 1.

[0503] Comparative Preparation Example 4

[0504] Comparative slurry 4 was prepared in the same manner as in Slurry Preparation Example 1, except that Comparative Compound B was used instead of Compound 1.

[0505]

[0506] <Comparative Compound B>

[0507] Comparative Preparation Example 5

[0508] Comparative slurry 5 was prepared in the same manner as in Slurry Preparation Example 4, except that Comparative Compound B was used instead of Compound 1.

[0509] Comparative Preparation Example 6

[0510] Comparative slurry 6 was prepared in the same manner as in Slurry Preparation Example 7, except that Comparative Compound B was used instead of Compound 1.

[0511] Evaluation Example

[0512] By using the slurries prepared according to Slurry Preparation Examples 1 to 9 and Comparative Preparation Examples 1 to 6, a slurry having A single-layer film with a thickness of 1000 nm was formed and heat-treated at 200° C. for 30 minutes, and then the UV spectrum of the single-layer film was measured.

[0513] 50 μL of methyl benzoate was added dropwise to the top of each monolayer film and allowed to stand for 30 minutes. The solvent was absorbed using a wiper, and each monolayer film was allowed to stand at 100° C. for 1 minute, and the UV spectrum of each monolayer film was measured.

[0514] Table 1 shows the film remaining ratio calculated as follows with respect to each single-layer film.

[0515] Film remaining rate = (UV measurement area after adding solvent (methyl benzoate) (solvent treatment) and leaving it to stand for 30 minutes) / (UV measurement area before solvent treatment)

[0516] [Table 1]

[0517] Slurry name polymer compounds low molecular weight compounds Membrane residual rate (%) Slurry 1 Compound 101 Compound 1 100 Slurry 2 Compound 101 Compound 2 100 Slurry 3 Compound 101 Compound 3 100 Slurry 4 Compound 102 Compound 1 100 Slurry 5 Compound 102 Compound 2 100 Slurry 6 Compound 102 Compound 3 100 Slurry 7 Compound 103 Compound 1 100 Slurry 8 Compound 103 Compound 2 100 Slurry 9 Compound 103 Compound 3 100 Comparative slurry 1 Compound 101 Comparative Compound A 20 Comparative slurry 2 Compound 102 Comparative Compound A 10 Comparative slurry 3 Compound 103 Comparative Compound A 20 Comparative slurry 4 Compound 101 Comparative Compound B 30 Comparative slurry 5 Compound 102 Comparative Compound B 35 Comparative slurry 6 Compound 103 Comparative Compound B 35

[0518] Example 1

[0519] Corning 15Ω / cm 2 The (120 nm) ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes.

[0520] PEDOT-PSS (AI4083) (purchased from Bayer) was coated on an ITO glass substrate and heat treated at 150°C for 30 minutes to form a The hole injection layer was spin-coated with slurry 1, dried at 100°C for 10 minutes, and then thermally cross-linked at 200°C for 30 minutes to form a hole injection layer having a thickness of The hole transport layer has a thickness of .

[0521] Then, a solution in which the host compound A and the dopant compound B (host ratio of 5%) were dissolved in a xylene solvent was spin-coated on the hole transport layer and dried at a temperature of 100° C. for 10 minutes to form a The thickness of the emission layer.

[0522] Then, compound C and 8-hydroxyquinoline lithium (LiQ) were vacuum deposited on the emission layer at a ratio of 5:5 to form a An electron transport layer having a thickness of The thickness of LiQ (electron injection layer) and having Al (cathode) with a thickness of , thereby completing the manufacture of the organic light-emitting device.

[0523]

[0524] [Compound C]

[0525]

[0526] Examples 2 to 9 and Comparative Examples 1 to 6

[0527] An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming the hole transport layer, each of Paste 2 to Paste 9 and Comparative Paste 1 to Comparative Paste 6 was used instead of Paste 1. In Table 2, the lifetime (T90) represents the amount of time (hr) that elapses when the luminance is 90% of the initial luminance (100%).

[0528] [Table 2]

[0529]

[0530] Referring to Table 2, it was confirmed that the organic light emitting devices of Examples 1 to 9 had low driving voltage and high efficiency compared with those of Comparative Examples 1 to 6.

[0531] An organic light emitting device including an azide-based compound may have low driving voltage and high efficiency.

[0532] While certain exemplary embodiments and implementations have been described herein, other embodiments and modifications will be apparent from this description. Accordingly, the inventive concept is not limited to such embodiments, but rather to the broader scope of the appended claims and various obvious modifications and equivalent arrangements as will be apparent to those skilled in the art.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode and including an emission layer; and Azide compounds represented by formula 1: <Formula 1> In formula 1, L1, L2, L3, L 11 and L 12 Each of the 10 Alkylene, Each of a1, a2, a3, a11 and a12 is independently an integer from 1 to 5, wherein when a1 is two or more, two or more L1s are the same or different from each other, when a2 is two or more, two or more L2s are the same or different from each other, when a3 is two or more, two or more L3s are the same or different from each other, when a11 is two or more, two or more L 11 are the same as or different from each other, and when a12 is two or more, two or more L 12 Same or different from each other, Each of b1 and b2 is independently an integer of 1 or 2, b3 is an integer of 0 or 1, When b3 is 0, *-((L3) a3 -N3) b3 For hydrogen, When b1 is 2, two *-((L1) a1 -N3) are the same or different from each other, and when b2 is two, the two *-((L2) a2 -N3) are the same as or different from each other, * indicates the binding site with the adjacent atom, and The substituted C1-C 10 At least one substituent in the alkylene group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 Alkoxy.

2. The organic light-emitting device according to claim 1, wherein The first electrode is an anode, the second electrode is a cathode, The organic layer includes at least one of the azide compounds represented by Formula 1, The organic layer further includes a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode. The hole transport region is selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, and any combination thereof, and The electron transport region is selected from the group consisting of a hole blocking layer, an electron transport layer, an electron injection layer, and any combination thereof.

3. The organic light-emitting device according to claim 2, wherein: The hole transport region includes at least one of the azide compounds.

4. The organic light-emitting device according to claim 3, wherein: The hole transport region further includes a polymer having a molecular weight of 5000 g / mol or greater. The organic light-emitting device according to claim 1 , wherein: The emission layer includes a host material and a dopant material, and The dopant material includes a phosphorescent dopant or a fluorescent dopant. The organic light-emitting device according to claim 1 , wherein: Each of L1, L2 and L3 is independently a single bond.

7. The organic light-emitting device according to claim 1, wherein L 11 and L 12 Each of is independently selected from: single bonds, methylene, ethylene, propylene, butylene, and pentylene; and are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone and C1-C 10 At least one selected from the group consisting of methylene, ethylene, propylene, butylene and pentylene among the alkyl groups.

8. The organic light-emitting device according to claim 1, wherein *-(L 11 ) a11 -*' and *-(L 12 ) a12 -*' are identical to each other, and * and *' indicate the binding sites with adjacent atoms.

9. The organic light emitting device according to claim 1, wherein The azide compound has a molecular weight of 100 g / mol to 2000 g / mol.

10. The organic light emitting device according to claim 1, wherein The sum of b1, b2, and b3 is 2, 3, 4, or 5. The organic light-emitting device according to claim 1 , wherein: The azide compound is represented by formula 1-1: <Formula 1-1> Among them, in formula 1-1, Each of b1 and b2 is independently an integer of 1 or 2, b3 is an integer of 0 or 1, When b3 is 0, *-(N3) b3 For hydrogen, * indicates the binding site with the adjacent atom, Each of Z1, Z2, Z3, Z4, Z5, Z6, Z7 and Z8 is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 Alkoxy.

12. The organic light emitting device according to claim 1, wherein The azide compound is selected from Compound 1, Compound 2 and Compound 3:

13. A composition comprising: Azide compounds represented by formula 1: <Formula 1> In formula 1, L1, L2, L3, L 11 and L 12 Each of the 10 Alkylene, Each of a1, a2, a3, a11 and a12 is independently an integer from 1 to 5, wherein when a1 is two or more, two or more L1s are the same or different from each other, when a2 is two or more, two or more L2s are the same or different from each other, when a3 is two or more, two or more L3s are the same or different from each other, when a11 is two or more, two or more L 11 are the same as or different from each other, and when a12 is two or more, two or more L 12 Same or different from each other, Each of b1 and b2 is independently an integer of 1 or 2, b3 is an integer of 0 or 1, When b3 is 0, *-((L3) a3 -N3) b3 For hydrogen, When b1 is 2, two *-((L1) a1 -N3) are the same or different from each other, and when b2 is two, the two *-((L2) a2 -N3) are the same as or different from each other, * indicates the binding site with the adjacent atom, and The substituted C1-C 10 At least one substituent in the alkylene group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 alkoxy; a polymer represented by Formula 2; and Solvent: <Formula 2> In formula 2, Each of Ar1, Ar2 and Ar3 is independently a substituted or unsubstituted C3-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group, Each of c1 and c2 is independently an integer from 1 to 3, n is an integer from 70 to 400, The substituted C3-C 60 The carbocyclic group and the substituted C1-C 60 At least one substituent in the heterocyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), and Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

14. The composition according to claim 13, wherein Ar1 to Ar3 are independently selected from: phenyl, naphthyl, fluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl 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 indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group.

15. The composition according to claim 13, wherein The polymer represented by Formula 2 is selected from Compound 101, Compound 102, and Compound 103:

16. The composition according to claim 13, wherein The polymer has a molecular weight of 5000 g / mol or greater, and The azide compound has a molecular weight of 2000 g / mol or less.

17. A method for manufacturing an organic light-emitting device, the method comprising: forming a hole transport region on the first electrode, wherein the formation of the hole transport region comprises a solution process using a composition, and The composition comprises: Azide compounds represented by formula 1: <Formula 1> In formula 1, L1, L2, L3, L 11 and L 12 Each of the 10 Alkylene, Each of a1, a2, a3, a11 and a12 is independently an integer from 1 to 5, wherein when a1 is two or more, two or more L1s are the same or different from each other, when a2 is two or more, two or more L2s are the same or different from each other, when a3 is two or more, two or more L3s are the same or different from each other, when a11 is two or more, two or more L 11 are the same as or different from each other, and when a12 is two or more, two or more L 12 Same or different from each other, Each of b1 and b2 is independently an integer of 1 or 2, b3 is an integer of 0 or 1, When b3 is 0, *-((L3) a3 -N3) b3 For hydrogen, When b1 is 2, two *-((L1) a1 -N3) are the same or different from each other, and when b2 is two, the two *-((L2) a2 -N3) are the same as or different from each other, * indicates the binding site with the adjacent atom, and The substituted C1-C 10 At least one substituent in the alkylene group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 Alkynyl and C1-C 10 alkoxy; a polymer represented by Formula 2; and Solvent: <Formula 2> In formula 2, Each of Ar1, Ar2 and Ar3 is independently a substituted or unsubstituted C3-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group, Each of c1 and c2 is an integer of 1, 2, or 3, n is an integer from 70 to 400, The substituted C3-C 60 The carbocyclic group and the substituted C1-C 60 At least one substituent in the heterocyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), and Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups.

18. The method according to claim 17, wherein: The formation of the hole transport region further comprises: performing thermal curing or photocuring on the azide compound and the polymer; or removing the solvent, The removal of the solvent is performed at a temperature ranging from 160°C to 280°C.

19. The method according to claim 17, further comprising forming an emission layer on the hole transport region, in, The forming of the emission layer includes a solution process using a second composition, and The second composition includes a host material, a dopant material, and a second solvent.

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