Light emitting device, method of manufacturing the same, and electronic device including the same

Abstract

A light-emitting device, a method of manufacturing the light-emitting device, and an electronic device including the light-emitting device are disclosed. The light-emitting device includes a first electrode, a second electrode facing the first electrode, and a sandwich layer disposed between the first electrode and the second electrode. The sandwich layer includes an emission layer and a hole transport region disposed between the first electrode and the emission layer. The hole transport region includes a hole injection layer and a hole transport layer disposed between the hole injection layer and the emission layer. The hole injection layer includes a first compound, the hole transport layer includes a second compound, and a glass transition temperature of the first compound is lower than a glass transition temperature of the second compound.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0074956, filed on June 19, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Technology

[0003] The embodiments relate to a light-emitting device, a method of manufacturing the light-emitting device, and an electronic device including the light-emitting device. Technical Field

[0004] A light-emitting device is a device that converts electrical energy into light energy. Examples of such devices include organic light-emitting devices that use organic materials for the emitting layer and quantum dot light-emitting devices that use quantum dots for the emitting layer.

[0005] In a light-emitting device, a first electrode is located on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to produce excitons. These excitons transition from an excited state to the ground state, thereby generating light. Summary of the Invention

[0006] The embodiments relate to light-emitting devices, methods of manufacturing the same, and electronic devices including the light-emitting devices. The embodiments also relate to light-emitting devices including a hole injection layer and a hole transport layer, wherein the glass transition temperature of a compound included in the hole injection layer is lower than the glass transition temperature of a compound included in the hole transport layer.

[0007] Other aspects will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practice of embodiments of this disclosure.

[0008] According to an embodiment, the light-emitting device may include a first electrode, a second electrode facing the first electrode, and a sandwich layer disposed between the first electrode and the second electrode.

[0009] The interlayer may include an emitter layer and a hole transport region disposed between the first electrode and the emitter layer.

[0010] The hole transport region may include a hole injection layer and a hole transport layer disposed between the hole injection layer and the emission layer.

[0011] The hole injection layer may include a first compound.

[0012] The hole transport layer may include a second compound, and

[0013] The glass transition temperature of the first compound may be lower than that of the second compound.

[0014] In an embodiment, the hole injection layer may further include a third compound having a glass transition temperature higher than that of the first compound.

[0015] In an implementation, the third compound may be the same as the second compound included in the hole transport layer.

[0016] In an embodiment, the weight ratio of the first compound to the third compound in the hole injection layer can be in the range of about 9:1 to about 1:9.

[0017] In an embodiment, the first compound may be an amine compound represented by Formula 1, and the second compound may be an amine compound represented by Formula 2:

[0018] [Formula 1]

[0019]

[0020] [Equation 2]

[0021]

[0022] In Equations 1 and 2,

[0023] CY 11 To CY 14 and CY 21 To CY 24 Each can be independently C3-C 30 Carbocyclic groups or C1-C 20 Heterocyclic groups,

[0024] L 11 To L 13 and L 21 To L 23 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0025] a11 to a13 and a21 to a23 can each be an integer selected from 0 to 5 independently.

[0026] Ar 11 and Ar 21 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0027] X 11 It can be O, S, N(R) 17 ), C(R 17 (R) 18 ) or Si(R 17 (R) 18 ),

[0028] X 21 It can be O, S, N(R) 27 ), C(R 27 (R) 28 ) or Si(R 27 (R) 28 ),

[0029] R 11 and R 12 Each can be independently unsubstituted or by at least one R 10a Replacement C2-C 11 alkyl,

[0030] R 21 and R 22 Each can be independently unsubstituted or by at least one R 10a Replacement C1-C 10 alkyl,

[0031] R 13 To R 18 and R 23 To R 28 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthio, -B(Q1)(Q2), -P(Q1)(Q2) or -C(=O)(Q1),

[0032] R 17 and R 18 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups,

[0033] R 27 and R 28 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups,

[0034] c13, c16, c23, and c26 can each be an integer selected from 1 to 3 independently.

[0035] c14, c15, c24, and c25 can each be an integer selected from 1 to 4 independently.

[0036] R 10a Possible forms:

[0037] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0038] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 11 (Q) 12 ) or combinations thereof;

[0039] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 21 (Q) 22 ) or a combination thereof; or

[0040] -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 ) or -P(=O)(Q 31 (Q) 32 ),and

[0041] Q1, Q2, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each group is unsubstituted or substituted with deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0042] In an embodiment, the hole injection layer may include two or more different first compounds represented by Formula 1, and at least one of the two or more different first compounds represented by Formula 1 may have a glass transition temperature lower than that of the second compound.

[0043] In an embodiment, the hole injection layer may further include a p-doper.

[0044] In an implementation, the hole transport region may further include an emission assist layer, an electron blocking layer, or a combination thereof.

[0045] In an embodiment, the hole transport region may further include an electron blocking layer disposed between the hole transport layer and the emission layer.

[0046] In an embodiment, the interlayer may further include an electron transport region disposed between the emitter layer and the second electrode, and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0047] In one embodiment, the electron transport region may include a hole blocking layer, an electron transport layer, and an electron injection layer sequentially disposed on the emitter layer.

[0048] According to an embodiment, a method for manufacturing a light-emitting device may include forming a hole injection layer on a first electrode, the hole injection layer comprising a first compound.

[0049] A hole transport layer is formed on the hole injection layer, the hole transport layer comprising a second compound having a glass transition temperature higher than that of the first compound.

[0050] An emission layer is formed on the hole transport layer.

[0051] A second electrode is formed on the emitting layer to form a light-emitting device, and

[0052] Heat treatment is applied to the light-emitting device.

[0053] According to an embodiment, the electronic device may include a light-emitting device.

[0054] In an embodiment, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode and a drain electrode, and a first electrode of the light-emitting device may be in electrical contact with one of the source electrode and the drain electrode of the thin-film transistor.

[0055] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or a combination thereof. Attached Figure Description

[0056] The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0057] Figure 1 This is a schematic cross-sectional view of the light-emitting device according to an embodiment;

[0058] Figure 2 This is a schematic cross-sectional view of a light-emitting device according to an embodiment of the present disclosure; and

[0059] Figure 3 This is a schematic cross-sectional view of a light-emitting device according to another embodiment of the present disclosure. Detailed Implementation

[0060] Reference will now be made in detail to embodiments, examples of which are shown in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this respect, embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described below with reference to the drawings only to explain aspects of the description.

[0061] Because this disclosure can be implemented in various modified forms, the embodiments are shown in the accompanying drawings and described in the detailed description. The effects and features of this disclosure, as well as the methods of implementing them, will become apparent when referring to the embodiments described with reference to the accompanying drawings. However, this disclosure can be implemented in many different forms and should not be construed as limited to the embodiments set forth herein.

[0062] Embodiments of the present disclosure will now be described in more detail with reference to the accompanying drawings. Components that are identical or corresponding to each other are given the same reference numerals, regardless of the drawing number, and redundant explanations are omitted.

[0063] Expressions used for the singular cover the expressions used for the plural, unless there is a clearly different meaning in the context.

[0064] It should be understood that the terms “comprise,” “comprising,” “include,” “including,” “have,” “having,” “contain,” and / or “containing” are intended to indicate the presence of a feature, integer, step, operation, element, component, or combination thereof stated in this disclosure, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0065] As will be understood in the specification, when an element (area, layer, or section, etc.) is referred to as being “on”, “connected to”, or “attached to” another element, it can be directly on, directly connected to, or directly attached to another element, or one or more intermediate elements can be disposed between them.

[0066] As used herein, the term “and / or” includes any and all combinations of one or more related listed items. For example, “A and / or B” can be understood to mean “A, B, or A and B”. The terms “and” and “or” can be used in a connecting or separating sense and can be understood as equivalent to “and / or”.

[0067] The term "at least one" is intended to include the meaning of "at least one selected from..." for its meaning and interpretation. For example, "at least one of A and B" can be understood to mean "A, B, or A and B". When preceding a list of elements, the term "at least one" modifies the entire list of elements, not any individual element in the list.

[0068] It will be understood that although the terms “first,” “second,” etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of embodiments of the inventive concept, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element.

[0069] The terms “below,” “under,” “above,” and “upper,” etc., are used to describe the relationships of the configurations shown in the accompanying drawings. These terms are used as relative concepts and are described with reference to the directions indicated in the accompanying drawings.

[0070] For ease of explanation, the dimensions of the elements in the accompanying drawings may be exaggerated. Therefore, since the dimensions and thicknesses of the components in the drawings are arbitrarily shown for ease of explanation, the following embodiments are not limited thereto.

[0071] As used herein, the term "interlayer" refers to a single layer, several layers, and / or all layers disposed between the first and second electrodes of a light-emitting device.

[0072] The expression “(interlayer) comprises a compound represented by Formula 1 or Formula 2” as used herein may include cases in which “(interlayer) comprises a compound of Formula 1 or Formula 2 or two or more different compounds of Formula 1 or Formula 2”.

[0073] As used herein, the terms “about” or “approximately” include stated values ​​and mean an acceptable range of deviations from the stated values ​​as determined by a person skilled in the art, taking into account the measurements in question and the errors associated with the measurement of the stated quantities (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.

[0074] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that 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 field and should not be interpreted in an idealized or overly formal sense unless expressly defined in the specification.

[0075] [ Figure 1 [Description]

[0076] Figure 1 This is a schematic cross-sectional view of the light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, a sandwich layer 130, and a second electrode 150.

[0077] Combining Figure 1 The structure of the light-emitting device 10 according to the embodiment and the method of manufacturing the light-emitting device 10 are described.

[0078] [First Electrode 110]

[0079] exist Figure 1 In this embodiment, a substrate may be additionally disposed below the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. The substrate may be a flexible substrate. For example, the substrate may comprise a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or combinations thereof.

[0080] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, a high work function material that can easily inject holes can be used as the material for forming the first electrode 110.

[0081] The first electrode 110 may be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or combinations thereof. In an embodiment, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or combinations thereof.

[0082] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0083] [Mezzanine 130]

[0084] A sandwich layer 130 is disposed on the first electrode 110. The sandwich layer 130 may include an emitter layer 131.

[0085] The interlayer 130 may include a hole transport region 120 disposed between the first electrode 110 and the emitter layer 131, and an electron transport region 140 disposed between the emitter layer 131 and the second electrode 150. Figure 1 The image shows an embodiment in which the light-emitting device 10 includes an electron transmission region 140. However, the electron transmission region 140 may be omitted if necessary.

[0086] In addition to various organic materials, the interlayer 130 may further include compounds containing metal elements (such as organometallic compounds) and inorganic materials (such as quantum dots).

[0087] The interlayer 130 may include: i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150 and ii) a charge generation layer disposed between the two emitting units. When the interlayer 130 includes the emitting units and charge generation layer as described above, the light-emitting device 10 may be a series light-emitting device.

[0088] [Hole transport region 120 in interlayer 130]

[0089] The hole transport region 120 may include a hole injection layer 121 and a hole transport layer 122. The hole transport layer 122 may be disposed between the hole injection layer 121 and the emission layer 131.

[0090] Hole injection layer 121 may include a first compound, and hole transport layer 122 may include a second compound, wherein the glass transition temperature of the first compound may be lower than the glass transition temperature of the second compound.

[0091] When a compound whose glass transition temperature is lower than that of the second compound included in the hole transport layer 122 is used as the first compound included in the hole injection layer 121, the light-emitting device 10 can have a long lifespan by reducing the driving voltage and improving brightness uniformity.

[0092] Furthermore, when the hole injection layer 121 comprises a first compound with a glass transition temperature lower than that of the second compound, the surface uniformity at the interface between the hole injection layer 121 and the hole transport layer 122 can be improved by a heat treatment process performed after manufacturing the light-emitting device 10. Therefore, the light-emitting device 10 can have low driving voltage, high efficiency, and long lifespan.

[0093] In light-emitting devices of the related art, materials with high glass transition temperatures are used as organic materials for the light-emitting device to prevent degradation of device performance. However, by introducing a material with a glass transition temperature lower than that of the material included in the hole transport layer 122 into the hole injection layer 121, the light-emitting device 10 according to the embodiments of the present disclosure can improve the surface uniformity at the interface between the hole injection layer 121 and the hole transport layer 122. Therefore, compared with light-emitting devices of the related art, the light-emitting device 10 is characterized by significantly improved brightness uniformity and lifetime.

[0094] In light-emitting devices in the relevant art, when a material with a low glass transition temperature is included in the hole transport layer, crystallization of the material can occur upon heating, and this crystallization can lead to current leakage in the light-emitting device. Therefore, in the light-emitting device 10 according to an embodiment of the present disclosure, when the hole injection layer 121 includes a compound with a low glass transition temperature and the hole transport layer 122 includes a compound with a glass transition temperature higher than that of the material included in the hole injection layer 121, the light-emitting device 10 can be stable against heat generated by heat treatment processes during the manufacture of the light-emitting device 10 or by the operation of the light-emitting device 10.

[0095] In one embodiment, the hole injection layer 121 may further include a third compound having a glass transition temperature higher than that of the first compound.

[0096] Here, the third compound included in the hole injection layer 121 may be the same as or different from the second compound included in the hole transport layer 122. For example, the third compound included in the hole injection layer 121 may be the same as the second compound included in the hole transport layer 122.

[0097] In some embodiments, the hole injection layer 121 may include a first compound and a third compound, and the ratio of the first compound to the third compound in the hole injection layer 121 may be in the range of about 9:1 to about 1:9. For example, the ratio of the first compound to the third compound in the hole injection layer 121 may be in the range of about 8:2 to about 2:8, or for example, the ratio of the first compound to the third compound in the hole injection layer 121 may be in the range of about 7:3 to about 3:7. However, embodiments of this disclosure are not limited thereto.

[0098] In an embodiment, the first compound may be an amine compound represented by Formula 1, and the second compound may be an amine compound represented by Formula 2:

[0099] [Formula 1]

[0100]

[0101] [Equation 2]

[0102]

[0103] In Equations 1 and 2,

[0104] CY 11 To CY 14 and CY 21 To CY 24 Each can be independently C3-C 30 Carbocyclic groups or C1-C 20 Heterocyclic groups,

[0105] L 11 To L 13 and L 21 To L 23 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0106] a11 to a13 and a21 to a23 can each be an integer selected from 0 to 5 independently.

[0107] Ar 11 and Ar 21 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0108] X 11 It can be O, S, N(R) 17 ), C(R 17 (R) 18 ) or Si(R 17 (R) 18 ),

[0109] X 21 It can be O, S, N(R) 27 ), C(R 27 (R) 28 ) or Si(R 27 (R) 28 ),

[0110] R 11 and R 12 Each can be independently unsubstituted or by at least one R 10a Replacement C2-C 11 alkyl,

[0111] R 21 and R 22 Each can be independently unsubstituted or by at least one R 10a Replacement C1-C 10 alkyl,

[0112] R 13 To R 18 and R 23 To R 28 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60Arylthio, -B(Q1)(Q2), -P(Q1)(Q2) or -C(=O)(Q1),

[0113] R 17 and R 18 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups,

[0114] R 27 and R 28 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups,

[0115] c13, c16, c23, and c26 can each be an integer selected from 1 to 3 independently.

[0116] c14, c15, c24, and c25 can each be an integer selected from 1 to 4 independently.

[0117] R 10a Possible forms:

[0118] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0119] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 11 (Q) 12 ) or combinations thereof;

[0120] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 21 (Q) 22 ) or a combination thereof; or

[0121] -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 ) or -P(=O)(Q 31 (Q) 32 ),and

[0122] Q1, Q2, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each group is unsubstituted or substituted with deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0123] In the implementation, in Equations 1 and 2, the ring CY 11 To CY 14 and CY 21 To CY 24 Each can be independently phenyl, naphthyl, phenanthryl, or anthracene. In embodiments, the cyclo(CY) group... 11 To CY 14 and CY 21 To CY 24 Each of them may be phenyl, but the embodiments disclosed herein are not limited thereto.

[0124] In the implementation method, in Equations 1 and 2, by The group represented and composed of The groups represented can each be independently represented by one of the formulas CY203, CY206, CY207, CY210, CY211, CY214, and CY217:

[0125]

[0126] In formulas CY203, CY206, CY207, CY210, CY211, CY214, and CY217,

[0127] R 10b and R 10c Each can be combined with R 10a The descriptions are the same, and

[0128] CY 201 To CY 204 Each can be independently C3-C 30 Carbocyclic groups or C1-C 20 Heterocyclic groups.

[0129] In the implementation, L in Equations 1 and 2 11 To L 13 and L 21 To L 23 Each can be independently:

[0130] Each of the following substituted or unsubstituted phenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indarabenyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryl, pyrroleyl, thiopheneyl, furanyl, thiorheyl, imidazolyl, pyrazolyl, thiazolyl, isothiazyl Azolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indaneyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, lavany, peryl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl, imidazopyrimidinyl, -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 -P(=O)(Q) 31 (Q) 32 ) or a combination thereof, and

[0131] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, cyano-substituted phenyl, biphenyl, terphenyl, or naphthyl.

[0132] In equations 1 and 2, when a11 is 0, (L 11 ) a11 It can be a single bond; when a12 is 0, (L 12) a12 It can be a single bond; when a13 is 0, (L 13 ) a13 It can be a single bond; when a21 is 0, (L 21 ) a21 It can be a single bond; when a22 is 0, (L 22 ) a22 It can be a single bond, and when a23 is 0, (L 23 ) a23 It can be a single key.

[0133] In the implementation, a11 to a13 and a21 to a23 in Equations 1 and 2 can each be 0 or 1 independently.

[0134] In the implementation, Ar in Equations 1 and 2 11 and Ar 21 Each of these can be independently substituted or substituted with one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenatenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, penfenyl, hexaphenyl, pentaphenyl, pyrroleyl, thiopheneyl, furanyl, thiorhemiyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleyl, isoyindolyl, quinolinyl, isoquinolinyl, benzo[] Quinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, azafluorenyl, azaspiro-difluorenyl, dibenzothiopheneyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopheneyl, imidazopyridyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one phenyl group 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentylenyl, hexaphenyl, pentaphenyl, pyrrole, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isindole, quinolinyl, iso Quinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiopyrimyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopyrimyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, azafluorenyl, azaspiro-difluorenyl, dibenzothiopheneyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopyrimyl, imidazopyridyl, imidazopyrimidinyl, -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 -P(=O)(Q) 31 (Q) 32 (or a combination thereof).

[0135] In the implementation, Ar in Equations 1 and 2 11 and Ar 21 Each can be independently one of the groups represented by formulas 5-1 to 5-21:

[0136]

[0137]

[0138] Among them, in equations 5-1 to 5-21,

[0139] Y 31 It can be O, S, N (Z) 35 ), C(Z) 33 (Z) 34 ) or Si(Z 36 (Z) 37 ),

[0140] Z 31 To Z 37Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl groups, C1-C groups substituted with at least one phenyl group 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, anthracene, fluoranyl, triphenylene, pyridyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthridine, acridineyl, phenanthroline, phenazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or -B(Q 31 (Q) 32 ),

[0141] e3 can be an integer selected from 1 to 3.

[0142] e4 can be an integer selected from 1 to 4.

[0143] e5 can be an integer selected from 1 to 5.

[0144] e6 can be an integer selected from 1 to 6.

[0145] e7 can be an integer selected from 1 to 7.

[0146] e9 can be an integer selected from 1 to 9.

[0147] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, cyano-substituted phenyl, biphenyl, terphenyl, or naphthyl, and

[0148] * Indicates the binding site with adjacent atoms.

[0149] In the implementation, Equations 1 and 2 are derived from *-(L 12 ) a12 -Ar 11 The group represented and the group composed of *-(L 22 ) a22 -Ar 21 The represented groups can each be independently one of the groups represented by formulas 6-1 to 6-6:

[0150]

[0151] In Formulae 6-1 to 6-6, * indicates a binding site to an adjacent atom. ​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​22 Each of these compounds can be independently ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, 1-methylbutyl, n-hexyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, 2-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, or n-decyl.

[0157] In the implementation method, R in Equation 1 11 and R 12 They can be the same as each other, and R in Equation 2 21 and R 22 They can be the same as each other.

[0158] In the implementation, R in Equations 1 and 2 13 To R 18 and R 23 To R 28 Each can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;

[0159] Each of the following C1-C that was not replaced or was replaced by: 20 Alkyl or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, or combinations thereof;

[0160] Each of the following groups, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, finadeninyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrroleyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthrolylyl, phenazinyl Benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl or azadibenzothiopyrrolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenatenyl, anthracene, fluoranyl, triphenylene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, indoleyl, isoyindolyl, indazoleyl, purine, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridine , phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, diazacarbazoleyl, azadibenzofuranyl, azadibenzothiophene, azadibenzothiopyrrolyl or combinations thereof; or

[0161] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) or -B(Q1)(Q2), and

[0162] Q1 to Q3 can each be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0163] In embodiments, the first compound may be represented by one of formulas 1-1 to 1-16, and the second compound may be represented by one of formulas 2-1 to 2-16:

[0164]

[0165]

[0166]

[0167]

[0168] Among them, in equations 1-1 to 1-16 and equations 2-1 to 2-16,

[0169] L 11 To L 13 L 21 To L 23 a11 to a13, a21 to a23, Ar 11Ar 21 X 11 X 21 R 11 To R 16 R 21 To R 26 C13 to C16 and C23 to C26 may each be the same as those described in the instruction manual.

[0170] In an embodiment, the first compound may be represented by one of formulas C-1 to C-60, wherein R1 and R2 may each be independently C2-C60. 11 Alkyl group, and the second compound may be represented by one of C-1 to C-60, wherein R1 and R2 may each be independently C1-C60. 10 alkyl:

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] In an embodiment, the hole injection layer 121 may include two or more different first compounds represented by Formula 1, and at least one of the two or more different first compounds may have a glass transition temperature lower than that of the second compound.

[0177] In an embodiment, the hole transport region 120 may further include a transmission assist layer, an electron blocking layer, or a combination thereof.

[0178] For example, the hole transport region 120 may have a multi-layer structure, such as a hole injection layer 121 / hole transport layer 122 structure, a hole injection layer 121 / hole transport layer 122 / emission auxiliary layer structure, or a hole injection layer 121 / hole transport layer 122 / electron blocking layer structure, wherein, in each structure, the layers are sequentially stacked on the first electrode 110.

[0179] In an embodiment, the hole transport region 120 may further include an electron blocking layer disposed between the hole transport layer 122 and the emission layer 131.

[0180] In addition to the first and second compounds, the hole transport region 120 may include a compound represented by formula 201, a compound represented by formula 202, or a combination thereof:

[0181] [Formula 201]

[0182]

[0183] [Formula 202]

[0184]

[0185] Among them, in equations 201 and 202,

[0186] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0187] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0188] xa1 to xa4 can each be an integer selected from 0 to 5 independently.

[0189] xa5 can be an integer selected from 1 to 10.

[0190] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0191] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10aThe substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group, etc.) (e.g., see compound HT16 below),

[0192] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and

[0193] na1 can be an integer selected from 1 to 4.

[0194] In embodiments, formulas 201 and 202 may each include at least one of the groups represented by formulas CY201 to CY217:

[0195]

[0196] In formulas CY201 to CY217, R 10b and R 10c Each can be combined with R 10a The descriptions are the same, CY ring 201 To CY 204 Each can be independently C3-C 20 Carbocyclic groups or C1-C 20 Heterocyclic groups, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or replaced by at least one R 10a replace.

[0197] In the implementation, the ring CY in formulas CY201 to CY217 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.

[0198] In an embodiment, formula 201 and formula 202 may each include at least one of the groups represented by formulas CY201 to CY203.

[0199] In an embodiment, formula 201 may include at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY217.

[0200] In the implementation, in formula 201, xa1 can be 1, R 201It can be one of the groups represented by formulas CY201 to CY203, xa2 can be 0, and R 202 It can be one of the groups represented by formulas CY204 to CY207.

[0201] In an implementation, each of Formulas 201 and 202 may not include one of the groups represented by Formulas CY201 to CY203.

[0202] In an embodiment, each of Formulas 201 and 202 may not include one of the groups represented by Formulas CY201 to CY203, and may include at least one of the groups represented by Formulas CY204 to CY217.

[0203] In an implementation, each of Formulas 201 and 202 may not include one of the groups represented by Formulas CY201 to CY217.

[0204] For example, hole transport region 120 may include one of compounds HT1 to HT44, 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), or combinations thereof:

[0205]

[0206]

[0207]

[0208]

[0209] The thickness of the hole transport region 120 can be approximately to approximately Within a certain range. For example, the thickness of the hole transport region 120 can be approximately... to approximately Within the range.

[0210] The thickness of the hole injection layer 121 can be approximately to approximately Within a certain range, and the thickness of the hole transport layer 122 can be approximately... to approximately Within a certain range. For example, the thickness of the hole injection layer 121 can be approximately... to approximately Within a certain range. For example, the thickness of the hole transport layer 122 can be approximately... to approximately Within the range.

[0211] When the thicknesses of the hole transport region 120, the hole injection layer 121, and the hole transport layer 122 are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0212] The emission assist layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can comprise the materials described above.

[0213] [p-dopant]

[0214] In addition to these materials, the hole transport region 120 may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region 120 (e.g., in the form of a single layer of charge-generating material).

[0215] The charge-generating material can be, for example, a p-doped agent.

[0216] In an embodiment, the hole injection layer 121 may further include a p-doper.

[0217] For example, the lowest unoccupied molecular orbital (LUMO) energy level of a p-doped agent can be equal to or less than about -3.5 eV.

[0218] In embodiments, p-dopers may include quinone derivatives, cyano-containing compounds, compounds containing elements EL1 and EL2, or combinations thereof.

[0219] Examples of quinone derivatives are TCNQ and F4-TCNQ.

[0220] Examples of cyano-containing compounds are HAT-CN and the compound represented by formula 221:

[0221]

[0222] [Equation 221]

[0223]

[0224] In Equation 221,

[0225] R 221 To R 223Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and

[0226] R 221 To R 223 At least one of them can be independently replaced by C3-C respectively. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or combinations thereof 20 Alkyl groups; or combinations thereof.

[0227] Regarding compounds containing elements EL1 and EL2, element EL1 can be a metal, a metalloid, or a combination thereof, and element EL2 can be a nonmetal, a metalloid, or a combination thereof.

[0228] Examples of metals include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), or cesium (Cs); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), or barium (Ba); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (… Co, rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) or gold (Au), etc.; later transition metals (e.g., zinc (Zn), indium (In) or tin (Sn), etc.); and lanthanides (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) or lutetium (Lu), etc.).

[0229] Examples of metalloids are silicon (Si), antimony (Sb) and tellurium (Te).

[0230] Examples of nonmetals are oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).

[0231] In the embodiments, examples of compounds containing elements EL1 and EL2 are metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides, or quasi-metal iodides), metal tellurides, and combinations thereof.

[0232] Examples of metal oxides are tungsten oxides (e.g., WO, W2O3, WO2, WO3, or W2O5), vanadium oxides (e.g., VO, V2O3, VO2, or V2O5), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, or Mo2O5), and rhenium oxides (e.g., ReO3).

[0233] Examples of metal halides include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0234] Examples of alkali metal halides include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0235] Examples of alkaline earth metal halides are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0236] Examples of transition metal halides include titanium halides (e.g., TiF4, TiCl4, TiBr4, or TiI4), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, or ZrI4), hafnium halides (e.g., HfF4, HfCl4, HfBr4, or HfI4), vanadium halides (e.g., VF3, VCl3, VBr3, or VI3), niobium halides (e.g., NbF3, NbCl3, NbBr3, or NbI3), and tantalum halides (e.g., TaF3, TaCl3, Ta...). Br3 or TaI3), chromium halides (e.g., CrF3, CrCl3, CrBr3 or CrI3), molybdenum halides (e.g., MoF3, MoCl3, MoBr3 or MoI3), tungsten halides (e.g., WF3, WCl3, WBr3 or WI3), manganese halides (e.g., MnF2, MnCl2, MnBr2 or MnI2), technetium halides (e.g., TcF2, TcCl2, TcBr2 or TcI2), rhenium halides (e.g., ReF2, ReCl2, ReBr... 2 or ReI2), iron halides (e.g., FeF2, FeCl2, FeBr2 or FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 or RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2 or OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2 or CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2 or RhI2), iridium halides (e.g., IrF2, IrCl2, Ir Nickel halides (e.g., NiF2, NiCl2, NiBr2, or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2, or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2, or PtI2), copper halides (e.g., CuF, CuCl, CuBr, or CuI), silver halides (e.g., AgF, AgCl, AgBr, or AgI), and gold halides (e.g., AuF, AuCl, AuBr, or AuI).

[0237] Examples of post-transition metal halides are zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, or ZnI2), indium halides (e.g., InI3), and tin halides (e.g., SnI2).

[0238] Examples of lanthanide metal halides are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3 and SmI3.

[0239] Examples of metal halide halides are antimony halides (e.g., SbCl5).

[0240] Examples of metal tellurides include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te, or Cs₂Te), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, or BaTe), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, Fe). Te, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe or Au2Te), post-transition metal tellurides (e.g., ZnTe) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe or LuTe).

[0241] [Emitting layer 131 in interlayer 130]

[0242] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer 131 can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. In an embodiment, the emitting layer 131 may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with or separated from each other. In an embodiment, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0243] In one embodiment, the emitting layer 131 may include a substrate and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or a combination thereof.

[0244] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer 131 can range from about 0.01 parts by weight to about 15 parts by weight.

[0245] In one implementation, the emission layer 131 may include quantum dots.

[0246] In one embodiment, the emission layer 131 may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or dopant in the emission layer 131.

[0247] The thickness of the emission layer 131 can be approximately to approximately Within a certain range. For example, the thickness of the emission layer 131 can be approximately... to approximately Within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer 131 is within these ranges.

[0248] [main body]

[0249] In an implementation, the main component may include a compound represented by formula 301:

[0250] [Formula 301]

[0251] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0252] In Equation 301,

[0253] Ar 301 and L 301 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0254] xb11 can be 1, 2, or 3.

[0255] xb1 can be an integer selected from 0 to 5.

[0256] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -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 ) or -P(=O)(Q 301 (Q) 302 ),

[0257] xb21 can be an integer selected from 1 to 5, and

[0258] Q 301 To Q 303 Each can be the same as described in Q1.

[0259] For example, when xb11 in equation 301 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.

[0260] In embodiments, the main body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or a combination thereof:

[0261] [Formula 301-1]

[0262]

[0263] [Formula 301-2]

[0264]

[0265] Among them, in equations 301-1 and 301-2,

[0266] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0267] X 301 Can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),

[0268] xb22 and xb23 can each be 0, 1, or 2 independently.

[0269] L301 xb1 and R 301 Each can be the same as described in the instruction manual.

[0270] L 302 To L 304 Each can be independently combined with L 301 The descriptions are the same.

[0271] xb2 to xb4 can each be independently identical to the one described in combination with xb1, and

[0272] R 302 To R 305 and R 311 To R 314 Each can be combined with R 301 The descriptions are the same.

[0273] In embodiments, the host may include alkaline earth metal complexes and / or Zn complexes. For example, the host may be a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or a combination thereof.

[0274] In embodiments, the main body may include one of compounds H1 to H124, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), or combinations thereof, but embodiments of this disclosure are not limited thereto:

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282] [Phosphorescent dopant]

[0283] Phosphorescent dopants may include at least one transition metal as the center metal.

[0284] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or combinations thereof.

[0285] Phosphorescent dopants can be electrically neutral.

[0286] For example, phosphorescent dopants may include organometallic compounds represented by formula 401:

[0287] [Formula 401]

[0288] M(L 401 ) xc1 (L 402 ) xc2

[0289] In Equation 401,

[0290] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)).

[0291] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0292] L 402 It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, wherein when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.

[0293] [Formula 402]

[0294]

[0295] In Equation 402, X 401 and X 402 They can be nitrogen or carbon independently.

[0296] Ring A 401 And Ring A 402 Each can be independently C3-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0297] T 401 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 = *',

[0298] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),

[0299] Q 411 To Q 414 Each can be the same as described in Q1.

[0300] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -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 ) or -P(=O)(Q 401 (Q) 402 ),

[0301] Q 401 To Q 403 Each can be the same as described in Q1.

[0302] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and

[0303] In Equation 402, * and *' each indicate the binding site with M in Equation 401.

[0304] In the implementation, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each of them can be nitrogen.

[0305] In the implementation, when xc1 in equation 402 is 2 or greater, two or more L 401 The two rings A in 401 Optional location via T 402 (They are linking groups) linked to each other, or two or more L 401 The two rings A in 402 Optional location via T 403 (They are linking groups) linked to each other (see compounds PD1 to PD4 and PD7). T 402 and T 403 Each can be combined with T 401 The descriptions are the same.

[0306] L in Equation 401 402 It can be an organic ligand. For example, L... 402 It may be a halogen group, a diketone group (e.g., an acetylacetone group), a carboxylic acid group (e.g., a pyridine carboxylic acid group), a -C (=O) group, an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group or a phosphite group), or a combination thereof.

[0307] Phosphorescent dopants may include, for example, one or a combination of compounds PD1 to PD25:

[0308]

[0309] [Fluorescent dopant]

[0310] Fluorescent dopants may include compounds containing amine groups, compounds containing styrene groups, or combinations thereof.

[0311] In an embodiment, the fluorescent dopant may include a compound represented by formula 501:

[0312] [Formula 501]

[0313]

[0314] In Equation 501,

[0315] Ar 501 L 501 To L 503 R 501 and R502 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0316] xd1 to xd3 can each be independently 0, 1, 2, or 3, and

[0317] xd4 can be 1, 2, 3, 4, 5 or 6.

[0318] For example, Ar in Equation 501 501 It can be a fused ring group (e.g., anthracene, 1,2-benzophenanthrene or pyrene) where three or more monocyclic groups are fused together.

[0319] In an implementation, xd4 in Equation 501 can be 2.

[0320] In embodiments, the fluorescent dopant may include one of compounds FD1 to FD36; DPVBi; DPAVBi; or a combination thereof:

[0321]

[0322]

[0323]

[0324] [Delayed fluorescence materials]

[0325] The emitting layer 131 may include a delayed fluorescence material.

[0326] The delayed fluorescence material used in this paper can be selected from any compound that can emit delayed fluorescence based on the delayed fluorescence emission mechanism.

[0327] Depending on the type of other materials included in the emission layer 131, the delayed fluorescence material included in the emission layer 131 may be used as a host or a dopant.

[0328] In this embodiment, the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material can be in the range of about 0 eV to about 0.5 eV. When the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material satisfies the above range, an upconversion from the triplet state to the singlet state of the delayed fluorescent material can occur effectively, and therefore, the luminous efficiency of the light-emitting device 10 can be improved.

[0329] For example, delayed fluorescence materials may include i) at least one electron donor (e.g., π-electron-rich C3-C).60 Cyclic groups, such as carbazole groups, and at least one electron acceptor (e.g., sulfoxide, cyano, or a nitrogen-containing C1-C group lacking π electrons). 60 Materials containing cyclic groups, and / or ii) comprising C8-C alloys in which two or more cyclic groups share boron (B) and are fused together. 60 Materials with polycyclic groups.

[0330] Delayed fluorescence materials may include at least one of compounds DF1 to DF9:

[0331]

[0332] [Quantum dot]

[0333] The emitter layer 131 may include quantum dots.

[0334] As used herein, quantum dot refers to a crystal of semiconductor compound and may include any material capable of emitting light at various wavelengths depending on the crystal size.

[0335] The diameter of quantum dots can be, for example, in the range of about 1 nm to about 10 nm.

[0336] Quantum dots can be synthesized through wet chemical processes, organometallic chemical vapor deposition processes, molecular beam epitaxy processes, or similar processes.

[0337] Wet chemical processes refer to methods in which organic solvents and precursor materials are mixed to grow quantum dot crystals. During crystal growth, the organic solvent acts as a dispersant that naturally coordinates on the surface of the quantum dot crystals and controls their growth. Therefore, the growth of quantum dot particles can be controlled by using processes that are easier and less costly to perform compared to vapor deposition processes (such as metal-organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE)).

[0338] Quantum dots may include group III-VI semiconductor compounds, group II-VI semiconductor compounds, group III-V semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or combinations thereof.

[0339] Examples of group III-VI semiconductor compounds are binary compounds, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2Se3, or InTe; ternary compounds, such as InGaS3, InGaSe3; or combinations thereof.

[0340] Examples of Group II-VI semiconductor compounds are binary compounds, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or combinations thereof.

[0341] Examples of Group III-V semiconductor compounds are binary compounds, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds, such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or GaAlNP; or combinations thereof. Group III-V semiconductor compounds may further include Group II elements. Examples of group III-V semiconductor compounds that further include group II elements are InZnP, InGaZnP, and InAlZnP.

[0342] Examples of group I-III-VI semiconductor compounds are ternary compounds, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or combinations thereof.

[0343] Examples of group IV-VI semiconductor compounds are binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or combinations thereof.

[0344] In embodiments, Group IV elements or compounds may include single-element compounds, such as Si or Ge; binary compounds, such as SiC or SiGe; or combinations thereof.

[0345] Each element included in a multi-element compound (such as binary, ternary, and quaternary compounds) may exist in the particles at a uniform or non-uniform concentration.

[0346] Quantum dots can have a single structure or a core-shell dual structure, with the single structure having a uniform concentration of each element included in the respective quantum dot. For example, the material included in the core can be different from the material included in the shell.

[0347] The shell of a quantum dot can serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the core and the shell can have a concentration gradient, wherein the concentration of elements present in the shell decreases towards the center.

[0348] Examples of the shell for quantum dots are metal or non-metal oxides, semiconductor compounds, or combinations thereof. Examples of metal or non-metal oxides are binary compounds, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; ternary compounds, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; or combinations thereof. Examples of semiconductor compounds are Group III-VI, Group II-VI, Group III-V, Group I-III-VI, Group IV-VI semiconductor compounds, or combinations thereof as described herein. In embodiments, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or combinations thereof.

[0349] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be about 45 nm or less. For example, the FWHM of the emission wavelength spectrum of quantum dots can be about 40 nm or less. For example, the FWHM of the emission wavelength spectrum of quantum dots can be about 30 nm or less. When the FWHM of the emission wavelength spectrum of quantum dots is within this range, color purity or color reproducibility can be improved. Light emitted through these quantum dots is illuminated from all directions. Therefore, a wide viewing angle can be increased.

[0350] Quantum dots can be spherical, conical, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanosheets.

[0351] By adjusting the size of the quantum dots, the band gap can also be adjusted, thereby obtaining light of various wavelengths in the quantum dot emission layer. Therefore, by using quantum dots of different sizes, light-emitting devices that emit light of various wavelengths can be implemented. In one embodiment, the size of the quantum dots can be selected to emit red, green, and / or blue light. Adjusting the size of the quantum dots allows for the combination of various colors of light to emit white light.

[0352] [Electron transport region 140 in interlayer 130]

[0353] The electron transport region 140 may have: i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of different materials, or iii) a multi-layer structure including layers containing different materials.

[0354] The electron transport region 140 may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0355] For example, the electron transport region 140 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 in each structure, the layers are sequentially stacked on the emitter layer 131.

[0356] In one embodiment, the electron transport region 140 may include a hole blocking layer, an electron transport layer, and an electron injection layer sequentially disposed on the emission layer 131.

[0357] Electron transport region 140 (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in electron transport region 140) may include a metal-free compound comprising at least one π-electron-deficient nitrogen-containing C1-C. 60 Cyclic groups.

[0358] In an embodiment, the electron transport region 140 may include a compound represented by formula 601:

[0359] [Formula 601]

[0360] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0361] In Equation 601,

[0362] Ar 601 and L 601 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0363] xe11 can be 1, 2, or 3.

[0364] xe1 can be 0, 1, 2, 3, 4, or 5.

[0365] R 601 It can be unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),

[0366] Q 601 To Q 603 Each can be the same as described in Q1.

[0367] xe21 can be 1, 2, 3, 4, or 5, and

[0368] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups.

[0369] For example, when xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.

[0370] In the implementation method, Ar in formula 601 601 It can be a substituted or unsubstituted anthracene group.

[0371] In an embodiment, the electron transport region 140 may include a compound represented by formula 601-1:

[0372] [Formula 601-1]

[0373]

[0374] In Equation 601-1,

[0375] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,

[0376] L 611 To L 613 Each can be combined with L 601 The descriptions are the same.

[0377] xe611 to xe613 can each be the same as described in conjunction with xe1.

[0378] R 611 To R 613 Each can be combined with R 601 The descriptions are the same, and

[0379] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups.

[0380] For example, xe1 and xe611 to xe613 in Equations 601 and 601-1 can each be 0, 1 or 2 independently.

[0381] Electron transport region 140 may include one of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or combinations thereof:

[0382]

[0383]

[0384]

[0385] The thickness of the electron transport region 140 can be approximately to approximately Within a certain range. For example, the thickness of the electron transport region 140 can be approximately... to approximately Within the range. When the electron transport region 140 includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or a combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each be within approximately [a certain range]. to approximately Within a certain range, and the thickness of the electron transport layer can be approximately... to approximately Within a certain range. For example, the thickness of the buffer layer, hole blocking layer, or electronic control layer can each be within approximately [a certain range]. to approximately Within a certain range. For example, the thickness of the electron transport layer can be approximately... to approximately Within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage when the thickness of the buffer layer, hole blocking layer, electron control layer, and / or electron transport layer is within these ranges.

[0386] In addition to the materials described above, the electron transport region 140 (e.g., the electron transport layer in the electron transport region 140) may further include a material containing metallic elements.

[0387] Materials containing metallic elements may include alkali metal complexes, alkaline earth metal complexes, or combinations thereof. The metal ion in alkali metal complexes may be Li, Na, K, Rb, or Cs ions, while the metal ion in alkaline earth metal complexes may be Be, Mg, Ca, Sr, or Ba ions. The ligands coordinating with the metal ions of the alkali metal or alkaline earth metal complexes may be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or combinations thereof.

[0388] For example, the material containing a metal element may include a Li complex. The Li complex may include, for example, the compound ET-D1(LiQ) or ET-D2:

[0389]

[0390] The electron transport region 140 may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0391] The electron injection layer may have: i) a single-layer structure composed of a single layer consisting of a single material, ii) a single-layer structure composed of a single layer consisting of different materials, or iii) a multilayer structure including layers containing different materials.

[0392] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.

[0393] The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a combination thereof.

[0394] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may be oxides and halides (e.g., fluorides, chlorides, bromides, or iodides), tellurides, or a combination thereof of the alkali metal, the alkaline earth metal, and the rare earth metal.

[0395] The compound containing an alkali metal may be an alkali metal oxide (such as Li2O, Cs2O, or K2O), an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI), or a combination thereof. The compound containing an alkaline earth metal may include an alkaline earth metal oxide, such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying the condition 0 < x < 1) or Ba x Ca 1-xO(x is a real number satisfying the condition 0 < x < 1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or a combination thereof. In an embodiment, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.

[0396] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include i) one of the ions of alkali metal, alkaline earth metal, and rare earth metal, and ii) as ligands connected to the metal ions, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

[0397] The electron injection layer may be composed of an alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof, or may further include an organic material (for example, a compound represented by Formula 601).

[0398] In an embodiment, the electron injection layer may be composed of: i) an alkali metal-containing compound (for example, an alkali metal halide), or ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or a combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer or a RbI:Yb co-deposited layer.

[0399] When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

[0400] The thickness of the electron injection layer may be in the range of about to about For example, the thickness of the electron injection layer may be in the range of about to approximately Within the aforementioned range, when the thickness of the electron injection layer is within this range, the electron injection layer can exhibit satisfactory electron injection characteristics without a significant increase in driving voltage.

[0401] [Second electrode 150]

[0402] The second electrode 150 may be disposed on the interlayer 130 having such a structure. The second electrode 150 may serve as a cathode (which is an electron injection electrode), and the material used for the second electrode 150 may be a metal, alloy, conductive compound, or a combination thereof, each having a low work function.

[0403] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or combinations thereof. The second electrode 150 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0404] The second electrode 150 may have a single-layer structure or a multi-layer structure including two or more layers.

[0405] [Capping layer]

[0406] The first capping layer may be disposed outside the first electrode 110, and / or the second capping layer may be disposed outside the second electrode 150. The light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in the order stated herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order stated herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order stated herein.

[0407] The light generated in the emitting layer 131 of the interlayer 130 of the light-emitting device 10 can be emitted outward through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer, and the light generated in the emitting layer 131 of the interlayer 130 of the light-emitting device 10 can be emitted outward through the second electrode 150 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer.

[0408] According to the principle of constructive interference, the first and second capping layers can increase the external luminous efficiency. Therefore, the light extraction efficiency of the light-emitting device 10 is increased, thereby improving the luminous efficiency of the light-emitting device 10.

[0409] Each of the first capping layer and the second capping layer may include a material having a refractive index equal to or greater than about 1.6 (at 589 nm).

[0410] The first capping layer and the second capping layer can each be an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including organic and inorganic materials.

[0411] The compound selected from at least one of the first and second capping layers may independently include a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthyl phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may optionally be substituted with substituents comprising O, N, S, Se, Si, F, Cl, Br, I, or a combination thereof.

[0412] In an embodiment, at least one of the first capping layer and the second capping layer may each independently comprise an amine-containing compound.

[0413] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by formula 201, a compound represented by formula 202, or a combination thereof.

[0414] In an embodiment, at least one of the first capping layer and the second capping layer may each independently comprise one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or a combination thereof:

[0415]

[0416] [Preparation Method]

[0417] The layers constituting the hole transport region 120, the emission layer 131, and the electron transport region 140 can be formed in specific regions using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0418] When forming the layer constituting the hole transport region 120, the emission layer 131, and the layer constituting the electron transport region 140 by vacuum deposition, by considering the materials to be included in the layers to be formed and the structure of the layers to be formed, a deposition temperature of about 100°C to about 500°C and a deposition temperature of about 10°C can be achieved. -8 To about 10 -3 The vacuum degree and about to approximately Deposition was carried out at a deposition rate of [missing information].

[0419] Another aspect of this disclosure provides a method for manufacturing a light-emitting device.

[0420] A method for manufacturing a light-emitting device may include: forming a hole injection layer on a first electrode, the hole injection layer comprising a first compound; forming a hole transport layer on the hole injection layer, the hole transport layer comprising a second compound having a glass transition temperature higher than that of the first compound; forming an emission layer on the hole transport layer; forming a second electrode on the emission layer to form a light-emitting device; and performing a heat treatment on the light-emitting device.

[0421] In this embodiment, the heat treatment of the light-emitting device can be performed at a temperature below the glass transition temperature of the second compound.

[0422] In one embodiment, prior to forming the emission layer, the method may further include forming an emission assist layer, an electron blocking layer, or a combination thereof on the hole transport layer.

[0423] In one embodiment, prior to forming the second electrode, the method may further include forming an electron transport region on the emitter layer. For example, forming the electron transport region may include forming an electron transport layer and an electron injection layer.

[0424] [Electronic Devices]

[0425] Another aspect of this disclosure provides an electronic device including a light-emitting device.

[0426] For example, electronic devices that include light-emitting devices can be light-emitting devices or authentication devices, etc.

[0427] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include: i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be disposed in at least one direction of propagation of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.

[0428] An electronic device may include a first substrate. The first substrate may include sub-pixels, color filters may include color filter regions corresponding to the sub-pixels respectively, and a color conversion layer may include color conversion regions corresponding to the sub-pixels respectively.

[0429] Pixel delimiting layers can be set between subpixels to delimit each of the subpixels.

[0430] The color filter may further include a color filter area and a light-blocking pattern disposed between adjacent color filter areas of the color filter area, and the color conversion layer may further include a color conversion area and a light-blocking pattern disposed between adjacent color conversion areas of the color conversion area.

[0431] The color filter region (or color conversion region) may include a first region emitting a first color of light, a second region emitting a second color of light, and / or a third region emitting a third color of light, wherein the first color of light, the second color of light, and / or the third color of light may have different maximum emission wavelengths from each other. For example, the first color of light may be red light, the second color of light may be green light, and the third color of light may be blue light. For example, the color filter region (or color conversion region) may include quantum dots. Specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as those described in the specification. The first region, the second region, and / or the third region may further include a scattering element.

[0432] For example, the light-emitting device can emit a first light, a first region can absorb the first light to emit a first first color light, a second region can absorb the first light to emit a second first color light, and a third region can absorb the first light to emit a third first color light. In this respect, the first, second, and third first color lights can have different maximum emission wavelengths from each other. Specifically, the first light can be blue light, the first first color light can be red light, the second first color light can be green light, and the third first color light can be blue light.

[0433] In addition to the light-emitting device described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the light-emitting device.

[0434] Thin-film transistors may further include gate electrodes or gate insulating layers, etc.

[0435] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, or oxide semiconductors, etc.

[0436] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device 10 to be extracted to the outside while preventing ambient air and moisture from penetrating into the light-emitting device 10. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0437] In addition to color filters and / or color conversion layers, various functional layers may be further provided on the sealed portion, depending on the purpose of the electronic device. These functional layers may include a touchscreen layer and a polarization layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device for authenticating an individual using biometric information from a biometric sample (e.g., a fingertip or pupil).

[0438] In addition to the light-emitting device, the certification device may further include a bioassay information collector.

[0439] Electronic devices can be applied to a variety of suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various measuring instruments, measuring instruments (e.g., measuring instruments for vehicles, aircraft, and ships), and projectors, etc.

[0440] [ Figure 2 and Figure 3 [Description]

[0441] Figure 2 A schematic cross-sectional view is provided to show a light-emitting device according to an embodiment of the present disclosure.

[0442] Figure 2 The light-emitting device includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a package portion 300 that seals the light-emitting device.

[0443] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 prevents impurities from penetrating through the substrate 100 and can provide a flat surface on the substrate 100.

[0444] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0445] The active layer 220 may include inorganic semiconductors (such as silicon or polysilicon), organic semiconductors or oxide semiconductors, and may include source region, drain region and channel region.

[0446] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.

[0447] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 is disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and is disposed between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

[0448] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source region and drain region of the active layer 220.

[0449] The TFT is electrically connected to a light-emitting device to drive the light-emitting device and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device is provided on the passivation layer 280. The light-emitting device includes a first electrode 110, a sandwich layer 130, and a second electrode 150.

[0450] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.

[0451] A pixel defining layer 290, including insulating material, may be disposed on the first electrode 110. The pixel defining layer 290 may expose a specific area of ​​the first electrode 110, and an interlayer 130 may be formed in the exposed area of ​​the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic acid-based organic film. Although not explicitly stated... Figure 2 As shown, at least some layers of the mezzanine 130 may extend across the upper portion of the pixel-defined layer 290, and thus may be set as a common layer.

[0452] The second electrode 150 may be disposed on the interlayer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0453] The encapsulation portion 300 may be disposed on the capping layer 170. The encapsulation portion 300 may be disposed on the light-emitting device and protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include an inorganic film, which may include silicon nitride (SiN). x ), silicon dioxide (SiO) xIndium tin oxide, indium zinc oxide, or combinations thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate or polyacrylic acid), epoxy resins (e.g., aliphatic glycidyl ether (AGE)), or combinations thereof; or combinations of inorganic and organic membranes.

[0454] Figure 3 A schematic cross-sectional view is provided to show a light-emitting device according to an embodiment of the present disclosure.

[0455] Figure 3 Light-emitting devices and Figure 2 The light-emitting device is the same, except that the light-blocking pattern 500 and the functional area 400 are additionally disposed on the encapsulation portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In the embodiment, Figure 3 The light-emitting device included in the light-emitting device can be a series of light-emitting devices.

[0456] [Definition of the term]

[0457] As used in this article, the term "C3-C" 60 A "carbocyclic group" refers to a cyclic group consisting only of carbon atoms and having 3 to 60 carbon atoms, such as C3-C6. 30 Carbocyclic groups, and as used herein by the term "C1-C". 60 "Heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms in addition to carbon, such as C1-C. 20 Heterocyclic group. C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups can be monocyclic groups consisting of a single ring or polycyclic groups in which two or more rings are fused together. For example, C1-C 60 The number of cyclic atoms in a heterocyclic group can range from 3 to 61.

[0458] As used in this article, the term "cyclic group" includes C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups.

[0459] As used in this article, “π-electron-rich C3-C” 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and excluding *-N=*' as the cyclic moiety, and as used herein, "a nitrogen-containing C1-C group lacking π electrons". 60 "Cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as the cyclic part.

[0460] For example,

[0461] C3-C 60 The carbocyclic group can be i) group T1 or ii) a fused-ring group in which two or more groups T1 are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentaenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, peryl, penfenyl, heptaenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indole, fluorenyl, spiro-difluorenyl, benzofluorenyl, indophenantyl, or indoanthracene).

[0462] C1-C 60 The heterocyclic group may be i) group T2, ii) a fused-ring group in which two or more groups T2 are fused together, or iii) a fused-ring group in which at least one group T2 and at least one group T1 are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranocarbazole, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranodibenzofuranyl, benzyl... Furanodibenzothiophene, benzothiophene, dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl Benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiopheneyl, or azadibenzofuranyl)

[0463] C3-C rich in π electrons 60 The cyclic group may be i) group T1, ii) a fused ring group in which two or more groups T1 are fused together, iii) group T3, iv) a fused ring group in which two or more groups T3 are fused together, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused together (e.g., C3-C). 60Carbocyclic groups, pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiol, benzothiophene, benzofuranyl, carbazole, dibenzothiol, dibenzothiophene, dibenzofuranyl, indole-carbazole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiophene-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiol, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene or benzothiophene-dibenzothiophene).

[0464] Nitrogen-containing C1-C lacking π electrons 60 The cyclic group may be i) group T4, ii) a fused ring group in which two or more groups T4 are fused together, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused together, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused together, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused together (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazole). The following groups are listed: benzo[i], benzimidazolyl, benzo[i]oxazolyl, benzo[i]isooxazolyl, benzo[i]thiazolyl, benzo[i]isothiazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzo[i]quinolinyl, benzo[i]isoquinolinyl, quinoxalinyl, benzo[i]quinoxalinyl, quinazolinyl, benzo[i]quinazolinyl, phenanthrolinel, cinolinyl, phthalazinyl, naphthidyl, imidazo[i]pyridinyl, imidazo[i]pyrimidinyl, imidazo[i]triazinyl, imidazo[i]pyrazinyl, imidazo[i]pyridazinyl, imidazo[i]pyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophene, azadibenzothiophene, or azadibenzofuranyl.

[0465] Group T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptane), norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl.

[0466] The group T2 can be furanyl, thiopheneyl, 1H-pyrrolyl, thiopheneyl, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaboracyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.

[0467] Group T3 can be furanyl, thiophene, 1H-pyrrole, thiophene, or borocyclopentadienyl, and

[0468] The group T4 can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azirthiolyl, aziboranecyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.

[0469] As used in this article, the terms "cyclic group" and "C3-C" are similar to those used in this article. 60 "Carbon ring group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" refers to a group fused with a cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, or a tetravalent group) according to the structure of a formula described in the corresponding terminology. For example, "phenyl" can be benzo[a], phenyl, or phenylene, etc., which can be readily understood by those skilled in the art from the structure of a formula including "phenyl".

[0470] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups are C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups, and divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups are C3-C. 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.

[0471] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group in a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, such as C2-C. 11 Alkyl, C1-C 10Alkyl, C2-C6 alkyl, or C1-C5 alkyl, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. As used herein, the term "C1-C" is used in conjunction with the preceding text. 60 "alkylene" refers to C1-C 60 Alkyl groups have the same structure as divalent groups, such as C1-C5 alkylene groups.

[0472] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond at the middle or end of an alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes are divalent groups with the same structure, such as C2-C5 alkenyl groups.

[0473] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 An alkyl group having at least one carbon-carbon triple bond at its middle or end, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 Alkynes are divalent groups with the same structure.

[0474] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy, ethoxy and isopropoxy.

[0475] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of such groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornelyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. The term "C3-C" is also used. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have the same divalent structure.

[0476] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms, further comprising at least one heteroatom as a cyclic atom in addition to a carbon atom, and examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have the same divalent structure.

[0477] As used in this article, 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 being non-aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also used. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.

[0478] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that, in addition to carbon atoms, has at least one heteroatom as a cyclic atom in its cyclic structure, and has 1 to 10 carbon atoms and at least one double bond. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.

[0479] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms), and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Examples of aryl groups include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl. When C6-C... 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings can fused together.

[0480] As used in this article, the term "C1-C" 60"Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system, which, in addition to a carbon atom, has at least one heteroatom as a cyclic atom and has 1 to 60 carbon atoms. As used herein, the term "C1-C" is also relevant. 60 "Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system, which, in addition to a carbon atom, has at least one heteroatom as a cyclic atom and has 1 to 60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings can fused together.

[0481] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, with only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure (e.g., having 8 to 60 carbon atoms). Examples of monovalent nonaromatic fused polycyclic groups are indenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, indo[a]phenanthryl, and indo[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0482] As used herein, the term “monovalent nonaromatic fused heterocyclic group” refers to a monovalent group having two or more rings fused together, having at least one heteroatom as a cyclic atom in addition to carbon atoms, and having no aromaticity throughout its molecular structure (e.g., having 1 to 60 carbon atoms). Examples of monovalent non-aromatic fused heterocyclic groups include pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azadibenzothiophene, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, isothiazolyl, oxadiazolyl, thiazolyl. Benzopyrazolyl, benzimidazoyl, benzoxazolyl, benzothiazoyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazoleyl, indolocarbazoleyl, benzofuranocarbazoleyl, benzothiophenecarbazoleyl, benzothiophenecarbazoleyl, benzoindolocarbazoleyl, benzocarbazoleyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenedibenzothiophenyl. As used herein, the term "divalent nonaromatic fused heteropolycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heteropolycyclic group.

[0483] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein by the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).

[0484] As used in this article, the term "R" 10a "refer to:

[0485] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0486] Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 11 (Q) 12 ) or combinations thereof;

[0487] Each of the following C3-Cs was not replaced or was replaced by the others 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -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 -P(=O)(Q) 21 (Q) 22 ) or a combination thereof; or

[0488] -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) or -P(=O)(Q 31 (Q) 32 ).

[0489] In the instruction manual, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each group is unsubstituted or substituted with deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0490] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, and combinations thereof.

[0491] As used herein, “Ph” refers to phenyl, “Me” refers to methyl, “Et” refers to ethyl, and “tert-Bu” or “Bu” refers to ethyl. t "Refers to tert-butyl, and as used herein, the term "OMe" refers to methyl methacrylate (MMA).

[0492] As used in this article, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C2 bond. 60 Aryl groups are substituted phenyl groups.

[0493] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group." For example, "terphenyl" could be a phenyl group having a C6-C substituted molecule. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.

[0494] Unless otherwise defined, as used herein, * and *' each refer to the binding site of the adjacent atom in the corresponding formula.

[0495] The compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail below with reference to synthesis examples and embodiments. The phrase "replacing A with B" used in the description of the synthesis examples means replacing A with an equal molar equivalent of B.

[0496] Example

[0497] [Synthesis example]

[0498] Synthesis Example 1: Synthesis of Compound 1-1

[0499]

[0500] 2-Bromo-9,9-dimethyl-9H-fluorene (2.7 g, 10 mmol) was dissolved in anhydrous toluene, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.6 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 6:1 v / v). The solvent was removed to obtain compound 1-1 as a white solid (4.5 g, 8.2 mmol, yield 82%). 1 H NMR (d 6 -DMSO, 500MHz): δ1.69(12H,-CH3), 7.14(2H), 7.28-7.40(9H), 7.49-7.54(6H), 7.70(2H), 7.85-7.89(4H)ppm.

[0501] Synthesis Example 2: Synthesis of Compounds 1-2

[0502]

[0503] 2-Bromo-9,9-diethyl-9H-fluorene (3.0 g, 10 mmol) was dissolved in anhydrous toluene, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.6 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 6:1 v / v). The solvent was removed to obtain compounds 1-2 as white solids (4.6 g, 8.0 mmol, yield 80%). 1 H NMR (d 6 -DMSO, 500MHz): δ0.89 (6H, -CH3), 1.68 (6H, -CH3), 1.89 (4H, -CH2-), 7.10 (2 H), 7.26-7.39(9H), 7.48(2H), 7.57(4H), 7.70(2H), 7.83(2H), 7.92(2H)ppm.

[0504] Synthesis Example 3: Synthesis of Compounds 1-3

[0505]

[0506] 2-Bromo-9,9-dibutyl-9H-fluorene (3.6 g, 10 mmol) was dissolved in anhydrous toluene, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.6 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 5:1 v / v). The solvent was removed to obtain compounds 1-3 as white solids (4.7 g, 7.4 mmol, yield 74%). 1 H NMR (d 6-DMSO, 500MHz): δ0.90 (6H, -CH3), 1.27-1.29 (8H, -CH2-), 1.69 (6H, -CH3), 1.84 (4H, -CH 2-), 7.17(2H), 7.25-7.41(9H), 7.50(2H), 7.56(4H), 7.72(2H), 7.84(2H), 7.91(2H)ppm.

[0507] Synthesis Example 4: Synthesis of Compounds 1-4

[0508]

[0509] 2-Bromo-9,9-dihexyl-9H-fluorene (4.1 g, 10 mmol) was dissolved in anhydrous toluene, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.6 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 5:1 v / v). The solvent was removed to obtain compounds 1-4 as white solids (4.6 g, 6.6 mmol, yield 66%). 1 H NMR (d 6 -DMSO, 500MHz): δ0.88 (6H, -CH3), 1.29 (16H, -CH2-), 1.69 (6H, -CH3), 1.83 (4H, - CH2-), 7.16(2H), 7.28-7.49(11H), 7.55(4H), 7.75(2H), 7.86(2H), 7.90(2H)ppm.

[0510] Synthesis Example 5: Synthesis of Compound 2-1

[0511]

[0512] (1) Synthetic intermediate 2-1-A

[0513] 3-Aminobiphenyl (17 g, 0.10 mol), 2-bromo-9,9-diphenyl-9H-fluorene (40 g, 0.10 mol), t-BuONa (14 g, 0.15 mol), t-Bu3P (0.6 g, 3.0 mmol), and Pd2(dba)3 (2.7 g, 3.0 mmol) were added to a reaction vessel (i.e., a Schlenk tube), dried under vacuum for 2 hours, and dissolved in toluene (500 mL). The reaction solution was stirred at 130 °C under a nitrogen atmosphere for 24 hours and cooled to room temperature. The solvent was removed under reduced pressure, and the resulting product was washed with excess dichloromethane and distilled water. An extraction process was performed to separate the organic layer. The separated organic layer was dried using MgSO4 and purified by column chromatography (solvent: dichloromethane) to obtain intermediate 2-1-A (44 g, 91 mmol, 91% yield).

[0514] (2) Synthesis of compound 2-1

[0515] 1-Bromo-9,9-dimethyl-9H-fluorene (2.7 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 2-1-A (4.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 3:1 v / v). The solvent was removed to obtain compound 2-1 as a white solid (4.6 g, 6.8 mmol, yield 68%). 1 H NMR (d 6 -DMSO, 500MHz): δ1.70(6H, -CH3), 7.06-7.10(5H), 7.16-7.19(5H), 7.26-7.41(12H), 7.49-7.56(6H), 7.75(2H), 7.84-7.90(3H)ppm.

[0516] Synthesis Example 6: Synthesis of Compound 2-2

[0517]

[0518] 1-Bromo-9,9-diethyl-9H-fluorene (3.0 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 2-1-A (4.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 3:1 v / v). The solvent was removed to obtain compound 2-2 (4.2 g, 6.0 mmol, 60% yield) as a white solid. 1 H NMR (d 6 -DMSO, 500MHz): δ0.89 (6H, -CH3), 1.89 (4H, -CH2-), 7.05-7.11(5H), 7.16- 7.18(5H), 7.27-7.40(12H), 7.50-7.56(6H), 7.73(2H), 7.86-7.90(3H)ppm.

[0519] Synthesis Example 7: Synthesis of Compounds 2-3

[0520]

[0521] 1-Bromo-9,9-dibutyl-9H-fluorene (3.6 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 2-1-A (4.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 2:1 v / v). The solvent was removed to obtain compound 2-3 (4.2 g, 5.5 mmol, 55% yield) as a white solid. 1 H NMR (d 6-DMSO, 500MHz): δ0.88 (6H, -CH3), 1.26-1.29 (8H), 1.83 (4H, -CH2-), 7.06-7.10 (5H ), 7.17-7.20(5H), 7.26-7.41(12H), 7.52-7.58(6H), 7.70(2H), 7.88-7.91(3H)ppm.

[0522] Synthesis Example 8: Synthesis of Compounds 2-4

[0523]

[0524] 1-Bromo-9,9-dihexyl-9H-fluorene (4.1 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 2-1-A (4.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 2:1 v / v). The solvent was removed to obtain compound 2-4 as a white solid (5.2 g, 6.4 mmol, yield 64%). 1 H NMR (d 6 -DMSO, 500MHz): δ0.89 (6H, -CH3), 1.26-1.30 (16H), 1.86 (4H, -CH2-), 7.05-7.10 (5H ), 7.18-7.21(5H), 7.27-7.41(12H), 7.48-7.55(6H), 7.72(2H), 7.86-7.91(3H)ppm.

[0525] Synthesis Example 9: Synthesis of Compound 3-1

[0526]

[0527] 3-(3-bromophenyl)-9,9'-spirodifluorene (4.7 g, 10 mmol) was dissolved in anhydrous toluene, and 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (2.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 3:1 v / v). The solvent was removed to obtain compound 3-1 as a white solid (5.1 g, 7.5 mmol, yield 75%). 1 H NMR (d 6 -DMSO, 500MHz): δ1.65(6H, -CH3), 7.00-7.08(3H), 7.16-7.18(3H), 7.24-7.45(13H), 7.60(4H), 7.70-7.72(2H), 7.86-7.90(5H), 8.17(1H)ppm.

[0528] Synthesis Example 10: Synthesis of Compound 3-2

[0529]

[0530] 3-(3-bromophenyl)-9,9'-spirodifluorene (4.7 g, 10 mmol) was dissolved in anhydrous toluene, and 9,9-diethyl-N-phenyl-9H-fluorene-2-amine (3.1 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 3:1 v / v). The solvent was removed to obtain compound 3-2 as a white solid (4.6 g, 6.6 mmol, yield 66%). 1 H NMR (d 6-DMSO, 500MHz): δ0.85 (6H, -CH3), 1.89 (4H, -CH2-), 6.99-7.08(3H), 7.15-7.19( 3H), 7.28-7.45(13H), 7.56(4H), 7.67-7.70(2H), 7.85-7.90(5H), 8.15(1H)ppm.

[0531] Synthesis Example 11: Synthesis of compound 3-3

[0532]

[0533] 3-(3-bromophenyl)-9,9'-spirodifluorene (4.7 g, 10 mmol) was dissolved in anhydrous toluene, and 9,9-dibutyl-N-phenyl-9H-fluorene-2-amine (3.7 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 2:1 v / v). The solvent was removed to obtain compound 3-3 as a white solid (4.0 g, 5.3 mmol, yield 53%). 1 H NMR (d 6 -DMSO, 500MHz): δ0.88 (6H, -CH3), 1.26-1.30 (8H, -CH2-), 1.83 (4H, -CH2-), 7.00-7. 10(3H), 7.16-7.38(16H), 7.56(4H), 7.67-7.70(2H), 7.86-7.89(5H), 8.17(1H)ppm.

[0534] Synthesis Example 12: Synthesis of Compounds 3-4

[0535]

[0536] 3-(3-bromophenyl)-9,9'-spirodifluoro (4.7 g, 10 mmol) was dissolved in anhydrous toluene, and 9,9-dihexyl-N-phenyl-9H-fluorene-2-amine (4.3 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: hexane:dichloromethane, 1:1 v / v). The solvent was removed to obtain compounds 3-4 as a white solid (5.6 g, 6.9 mmol, yield 69%). 1 H NMR (d 6 -DMSO, 500MHz): δ0.85 (6H, -CH3), 1.26-1.30 (16H, -CH2-), 1.85 (4H, -CH2-), 7.00-7 .08(3H), 7.19-7.38(16H), 7.54(4H), 7.64-7.67(2H), 7.85-7.90(5H), 8.13(1H)ppm.

[0537] Synthesis Example 13: Synthesis of Compound 4-1

[0538]

[0539] 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.0 g, 10 mmol) was dissolved in anhydrous toluene, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (3.6 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: dichloromethane). The solvent was removed to obtain compound 4-1 as a white solid (5.8 g, 8.5 mmol, yield 85%). 1 H NMR (d 6-DMSO, 500MHz): δ1.64(6H, -CH3), 7.16-7.20(2H), 7.30-7.40(8H), 7.49- 7.62(14H), 7.74(2H), 7.89-7.91(3H), 8.13(1H), 8.19(1H), 8.30(1H)ppm.

[0540] Synthesis Example 14: Synthesis of Compound 4-2

[0541]

[0542] (1) Synthetic intermediate 4-2-A

[0543] 4-Aminobiphenyl (17 g, 0.10 mol), 2-bromo-9,9-diethyl-9H-fluorene (30 g, 0.10 mol), t-BuONa (14 g, 0.15 mol), t-Bu3P (0.6 g, 3.0 mmol), and Pd2(dba)3 (2.7 g, 3.0 mmol) were added to a reaction vessel (i.e., a Schlenk tube), dried under vacuum for 2 hours, and dissolved in toluene (500 mL). The reaction solution was stirred at 130 °C under a nitrogen atmosphere for 24 hours and cooled to room temperature. The solvent was removed under reduced pressure, and the resulting product was washed with excess dichloromethane and distilled water. An extraction process was performed to separate the organic layer. The separated organic layer was dried using MgSO4 and purified by column chromatography (solvent: dichloromethane) to obtain intermediate 4-2-A (35 g, 90 mmol, 90% yield).

[0544] (2) Synthesis of compound 4-2

[0545] 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.0 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 4-2-A (3.9 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: dichloromethane). The solvent was removed to obtain compound 4-2 (4.4 g, 6.2 mmol, 62% yield) as a white solid. 1 H NMR (d 6-DMSO, 500MHz): δ0.80 (6H, -CH3), 1.85 (4H, -CH2-), 7.13-7.19 (2H), 7.26-7.38 (8H ), 7.50-7.61(14H), 7.75(2H), 7.89-7.92(3H), 8.12(1H), 8.20(1H), 8.32(1H)ppm.

[0546] Synthesis Example 15: Synthesis of Compound 4-3

[0547]

[0548] (1) Synthetic intermediate 4-3-A

[0549] 4-Aminobiphenyl (17 g, 0.10 mol), 2-bromo-9,9-dibutyl-9H-fluorene (36 g, 0.10 mol), t-BuONa (14 g, 0.15 mol), t-Bu3P (0.6 g, 3.0 mmol), and Pd2(dba)3 (2.7 g, 3.0 mmol) were added to a reaction vessel (i.e., a Schlenk tube), dried under vacuum for 2 hours, and dissolved in toluene (500 mL). The reaction solution was stirred at 130 °C under a nitrogen atmosphere for 24 hours and cooled to room temperature. The solvent was removed under reduced pressure, and the resulting product was washed with excess dichloromethane and distilled water. An extraction process was performed to separate the organic layer. The separated organic layer was dried using MgSO4 and purified by column chromatography (solvent: dichloromethane) to obtain intermediate 4-3-A (28 g, 63 mmol, yield 63%).

[0550] (2) Synthesis of compound 4-3

[0551] 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.0 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 4-3-A (4.5 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: dichloromethane). The solvent was removed to obtain compound 4-3 (4.0 g, 5.4 mmol, 54% yield) as a white solid. 1 H NMR (d 6-DMSO, 500MHz): δ0.89 (6H, -CH3), 1.28-1.33 (8H, -CH2-), 1.89 (4H, -CH2-), 7.15-7.20 (2H), 7. 29-7.40(8H), 7.50-7.62(14H), 7.77(2H), 7.90-7.94(3H), 8.09(1H), 8.21(1H), 8.30(1H)ppm.

[0552] Synthesis Example 16: Synthesis of Compound 4-4

[0553]

[0554] (1) Synthetic intermediate 4-4-A

[0555] 4-Aminobiphenyl (17 g, 0.10 mol), 2-bromo-9,9-dihexyl-9H-fluorene (41 g, 0.10 mol), t-BuONa (14 g, 0.15 mol), t-Bu3P (0.6 g, 3.0 mmol), and Pd2(dba)3 (2.7 g, 3.0 mmol) were added to a reaction vessel (i.e., a Schlenk tube), dried under vacuum for 2 hours, and dissolved in toluene (500 mL). The reaction solution was stirred at 130 °C under a nitrogen atmosphere for 24 hours and cooled to room temperature. The solvent was removed under reduced pressure, and the resulting product was washed with excess dichloromethane and distilled water. An extraction process was performed to separate the organic layer. The separated organic layer was dried using MgSO4 and purified by column chromatography (solvent: dichloromethane) to obtain intermediate 4-4-A (35 g, 70 mmol, 70% yield).

[0556] (2) Synthesis of compound 4-4

[0557] 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.0 g, 10 mmol) was dissolved in anhydrous toluene, and intermediates 4-4-A (5.0 g, 10 mmol), CsCO3 (6.0 g, 32 mmol), Pd(OAc)2 (0.25 g, 1.1 mmol), and t-Bu3P (0.25 g, 1.2 mmol) were added. The reaction solution was stirred at 120 °C under a nitrogen atmosphere for 24 hours. After cooling the solution to room temperature, the solvent was removed under reduced pressure, and the remaining solid was extracted with dichloromethane. The extracted solution was washed with water and brine, and water was removed with MgSO4. The resulting solution was filtered to remove the solid, concentrated, and purified by column chromatography (solvent: dichloromethane). The solvent was removed to obtain compound 4-4 (3.7 g, 4.5 mmol, 45% yield) as a white solid. 1H NMR (d 6 -DMSO, 500MHz): δ0.87 (6H, -CH3), 1.25-1.28 (16H, -CH2-), 1.90 (4H, -CH2-), 7.13-7.18 (2H), 7 .28-7.37(8H), 7.51-7.62(14H), 7.79(2H), 7.89-7.93(3H), 8.15(1H), 8.24(1H), 8.35(1H)ppm.

[0558] Evaluation Example 1: Measurement of Glass Transition Temperature

[0559] The glass transition temperatures of compounds 1-1 to 1-4, 2-1 to 2-4, 3-1 to 3-4 and 4-1 to 4-4 used in the examples and comparative examples were measured at 10 °C / min using a differential scanning calorimeter (TA Instrument Q20), and the results are shown in Table 1.

[0560] [Table 1]

[0561]

[0562]

[0563]

[0564] Referring to Table 1, it was confirmed that in these compounds, the glass transition temperature decreased with increasing number of carbon atoms of the alkyl group substituted on carbon 9 of the fluorenyl group.

[0565] [Example of device manufacturing]

[0566] Comparative Example 1-1

[0567] As the anode, an ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.5 mm, ultrasonicated with isopropanol and pure water for 10 minutes each, and cleaned by exposure to ultraviolet radiation and ozone for 10 minutes. The resulting glass substrate was loaded onto a vacuum deposition apparatus. Compound 1-1 and NDP-9 (Novaled Company) (3 wt%) were co-deposited to form a thickness of [missing information]. A hole injection layer was formed, and compound 1-1 was deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer was then formed. Subsequently, compound HT1 was vacuum-deposited onto the hole transport layer to form a thickness of [missing information]. An electron blocking layer was formed. HOST1:DOPANT1 was deposited on the electron blocking layer at a weight ratio of 97:3 to form a thickness of [missing information]. The emitter layer. Compound T2T was vacuum deposited onto the emitter layer to form a thickness of [missing information]. A hole-blocking layer was formed. TPBi and LiQ (lithium 8-hydroxyquinoline) were vacuum-deposited onto the hole-blocking layer at a 1:1 weight ratio to form a thickness of [missing information]. The electron transport layer. Then, LiF... And Al A light-emitting device is fabricated by depositing an electron transport layer as an electron injection layer and a cathode. The fabricated light-emitting device is then subjected to a heat treatment process at 85°C to complete the fabrication process.

[0568]

[0569] Compare Examples 1-2, 2-1, 2-2, 3-1, 3-2, 4-1, and 4-2

[0570] In Comparative Examples 1-2, 2-1, 2-2, 3-1, 3-2, 4-1, and 4-2, the compounds shown in Table 2 were used instead of compound 1-1 in the formation of the hole injection layer and the hole transport layer.

[0571] Here, the heat treatment process after the manufacture of the light-emitting devices for Comparative Examples 1-2, 2-2, 3-2 and 4-2 is omitted.

[0572] Examples 1-1 to 1-3

[0573] The light-emitting devices of Examples 1-1, 1-2 and 1-3 were manufactured in the same manner as those of Comparative Example 1-1, except that compounds 1-1 were used instead of compound 1-1 in forming the hole injection layer.

[0574] Examples 1-4 to 1-6

[0575] The light-emitting devices of Examples 1-4, 1-5 and 1-6 were manufactured in the same manner as those in Comparative Example 1-1, except that compounds 1-1 and 1-4 were co-deposited in the hole injection layer at ratios of 9:1, 7:3 and 5:5, respectively, instead of compound 1-1.

[0576] Examples 2-1 to 2-3

[0577] The light-emitting devices of Examples 2-2, 2-3 and 2-4 were manufactured in the same manner as those of Comparative Example 2-1, except that compounds 2-2, 2-3 and 2-4 were used instead of compound 2-1 in forming the hole injection layer.

[0578] Examples 2-4 to 2-6

[0579] The light-emitting devices of Examples 2-4, 2-5 and 2-6 were manufactured in the same manner as those in Comparative Example 2-1, except that compounds 2-1 and 2-4 were co-deposited in the hole injection layer at ratios of 9:1, 7:3 and 5:5, respectively, instead of compound 2-1.

[0580] Examples 3-1 to 3-3

[0581] The light-emitting devices of Examples 3-1, 3-2 and 3-3 were manufactured in the same manner as those of Comparative Example 3-1, except that compounds 3-2, 3-3 and 3-4 were used instead of compound 3-1 in forming the hole injection layer.

[0582] Examples 3-4 to 3-6

[0583] The light-emitting devices of Examples 3-4, 3-5 and 3-6 were manufactured in the same manner as those of Comparative Example 3-1, except that compounds 3-1 and 3-4 were co-deposited in the hole injection layer at ratios of 9:1, 7:3 and 5:5, respectively, instead of compound 3-1.

[0584] Examples 4-1 to 4-3

[0585] The light-emitting devices of Examples 4-1, 4-2 and 4-3 were manufactured in the same manner as those of Comparative Example 4-1, except that compounds 4-2, 4-3 and 4-4 were used instead of compound 4-1 in forming the hole injection layer.

[0586] Examples 4-4 to 4-6

[0587] The light-emitting devices of Examples 4-4, 4-5 and 4-6 were manufactured in the same manner as those of Comparative Example 4-1, except that compounds 4-1 and 4-4 were co-deposited in the hole injection layer at ratios of 9:1, 7:3 and 5:5, respectively, instead of compound 4-1.

[0588] Evaluation Example 2: Evaluation of Device Performance

[0589] The driving voltage, current efficiency, and lifetime (T0) of the light-emitting devices manufactured according to Comparative Examples 1-1 to 4-2 and Examples 1-1 to 4-6 were measured using a Keithley SMU 236 and a PR650 luminance meter. 97 The results are shown in Table 2. Lifetime (T) 97 ( ) is the time taken after the light-emitting device is driven until the brightness (@400 nits) decreases to 97% of the initial brightness (100%).

[0590] [Table 2]

[0591]

[0592]

[0593]

[0594] Data marked with * indicates results obtained without heat treatment after the light-emitting device is manufactured.

[0595] As shown in Table 2, compared with the light-emitting devices of the comparative examples in which the hole injection layer and the hole transport layer comprise the same compound, the light-emitting devices of the embodiments in which the hole injection layer comprises a compound with a glass transition temperature lower than that of the compound contained in the hole transport layer have a lower driving voltage, improved efficiency, and a particularly significantly improved lifetime.

[0596] It has been confirmed that the light-emitting device according to the embodiments of this disclosure exhibits excellent performance in terms of driving voltage, luminous efficiency and lifespan.

[0597] According to the implementation method, the light-emitting device may have low driving voltage, high efficiency and long life.

[0598] It should be understood that the embodiments described herein should be considered descriptive only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although embodiments have been described with reference to figures, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as A sandwich layer is disposed between the first electrode and the second electrode, wherein The interlayer includes an emitter layer and a hole transport region disposed between the first electrode and the emitter layer. The hole transport region includes a hole injection layer and a hole transport layer disposed between the hole injection layer and the emission layer. The hole injection layer includes a first compound. The hole transport layer includes a second compound, and The glass transition temperature of the first compound is lower than that of the second compound. The first compound is an amine compound represented by Formula 1, and The second compound is an amine compound represented by Formula 2: [Formula 1] [Equation 2] In Equations 1 and 2, CY 11 To CY 14 and CY 21 To CY 24 Each independently constitutes C3-C 30 Carbocyclic groups or C1-C 20 Heterocyclic groups, L 11 To L 13 and L 21 To L 23 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, a11 to a13 and a21 to a23 are each independent integers selected from 0 to 5. Ar 11 and Ar 21 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, X 11 is O, S, N(R 17 ), C(R 17 )(R 18 ), or Si(R 17 )(R 18 ), X 21 is O, S, N(R 27 ), C(R 27 )(R 28 ), or Si(R 27 )(R 28 ), R 11 and R 12 Each independently is either unsubstituted or by at least one R 10a Replacement C2-C 11 alkyl, R 21 and R 22 Each independently is either unsubstituted or by at least one R 10a Replacement C1-C 10 alkyl, R in Equation 2 21 and R 22 These are R in Equation 1. 11 and R 12 Alkyl groups with fewer carbon atoms R 13 To R 18 and R 23 To R 28 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthio, -B(Q1)(Q2), -P(Q1)(Q2) or -C(=O)(Q1), R 17 and R 18 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, R 27 and R 28 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, c13, c16, c23, and c26 are each independent integers selected from 1 to 3. c14, c15, c24, and c25 are each an independent integer selected from 1 to 4. R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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 -P(=O)(Q) 11 (Q) 12 ) or combinations thereof; Each of the following C3-Cs that were not replaced or were replaced: 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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 -P(=O)(Q) 21 (Q) 22 ) or combinations thereof; or -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 ) or -P(=O)(Q 31 (Q) 32 ),and Q1, Q2, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each group is unsubstituted or substituted with deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

2. The light-emitting device of claim 1, wherein the hole injection layer further comprises a third compound having a glass transition temperature higher than that of the first compound.

3. The light-emitting device of claim 2, wherein the third compound is the same as the second compound included in the hole transport layer.

4. The light-emitting device as claimed in claim 1, wherein: R in Equation 1 11 and R 12 Each independently is either unsubstituted or by at least one R 10a Substituted C2-C6 alkyl groups, and R in Equation 2 21 and R 22 Each independently is either unsubstituted or by at least one R 10a Substituted C1-C5 alkyl groups.

5. The light-emitting device as claimed in claim 1, wherein: The hole injection layer comprises two or more different first compounds represented by Formula 1, and At least one of the two or more different first compounds represented by Formula 1 has a glass transition temperature lower than that of the second compound.

6. The light-emitting device of claim 1, wherein the hole transport region further comprises an electron blocking layer disposed between the hole transport layer and the emission layer.

7. A method for manufacturing a light-emitting device, the method comprising: A hole injection layer is formed on the first electrode, the hole injection layer comprising a first compound; A hole transport layer is formed on the hole injection layer, the hole transport layer comprising a second compound having a glass transition temperature higher than that of the first compound; An emission layer is formed on the hole transport layer; A second electrode is formed on the emitting layer to form a light-emitting device; as well as The light-emitting device is subjected to heat treatment. The first compound is an amine compound represented by Formula 1, and The second compound is an amine compound represented by Formula 2: [Formula 1] [Equation 2] In Equations 1 and 2, CY 11 To CY 14 and CY 21 To CY 24 Each independently constitutes C3-C 30 Carbocyclic groups or C1-C 20 Heterocyclic groups, L 11 To L 13 and L 21 To L 23 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, a11 to a13 and a21 to a23 are each independent integers selected from 0 to 5. Ar 11 and Ar 21 Each independently is either unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, X 11 is O, S, N(R 17 ), C(R 17 )(R 18 ), or Si(R 17 )(R 18 ), X 21 is O, S, N(R 27 ), C(R 27 )(R 28 ), or Si(R 27 )(R 28 ), R 11 and R 12 Each independently is either unsubstituted or by at least one R 10a Replacement C2-C 11 alkyl, R 21 and R 22 Each independently is either unsubstituted or by at least one R 10a Replacement C1-C 10 alkyl, R in Equation 2 21 and R 22 These are R in Equation 1. 11 and R 12 Alkyl groups with fewer carbon atoms R 13 To R 18 and R 23 To R 28 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthio, -B(Q1)(Q2), -P(Q1)(Q2) or -C(=O)(Q1), R 17 and R 18 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, R 27 and R 28 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, c13, c16, c23, and c26 are each independent integers selected from 1 to 3. c14, c15, c24, and c25 are each an independent integer selected from 1 to 4. R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the following C1-C that was not replaced or was replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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 -P(=O)(Q) 11 (Q) 12 ) or combinations thereof; Each of the following C3-Cs that were not replaced or were replaced: 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, -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 -P(=O)(Q) 21 (Q) 22 ) or combinations thereof; or -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 ) or -P(=O)(Q 31 (Q) 32 ),and Q1, Q2, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each group is unsubstituted or substituted with deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

8. An electronic device comprising a light-emitting device as claimed in any one of claims 1 to 6 or the light-emitting device manufactured by the method as claimed in claim 7.

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