Organic Electronic Devices

Abstract

An embodiment of the present invention is directed to an organic electronic device capable of ensuring high luminous efficiency, low driving voltage, and high heat resistance and improving color purity or lifespan.

Description

Technical Field

[0001] Embodiments of the present disclosure relate to an organic electronic device. Background Art

[0002] Generally speaking, organic electroluminescence refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic electronic device using organic electroluminescence has a structure that generally includes an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer has a multilayer structure consisting of a plurality of layers formed of different materials to improve the efficiency and stability of the organic electronic device.

[0003] Currently, in the portable display market, the size of the display is getting larger and larger to become a large-area display. Because the portable display is provided with a battery having a limited power source, the portable display requires more efficient power consumption than that required by a conventional portable display. In addition, in this case, not only the challenge of efficient power consumption but also the challenges related to luminous efficiency and lifespan need to be solved.

[0004] In order to overcome the problems related to power consumption, luminous efficiency and lifespan, research has been conducted on tandem organic electronic devices in which the organic material layer includes two or more stacks (or emission units), each stack including an emission layer. Specifically, research has been conducted to improve power consumption, luminous efficiency and lifespan by improving the organic materials included in the stack.

[0005] Efficiency, lifespan, driving voltage, etc. are related to each other. The improvement of efficiency leads to a relative reduction in driving voltage, which can reduce the crystallization of organic materials caused by Joule heating during driving, thereby extending lifespan. However, simply improving the organic material layer may not maximize efficiency. This is because when the optimal combination of energy levels and T1 values ​​between each organic material and the inherent properties of the material (e.g., mobility, interface characteristics) is achieved, both extended lifespan and high efficiency can be achieved. Therefore, it is necessary to develop a material that can effectively achieve charge balance in the emission layer while having high thermal stability.

[0006] Specifically, in tandem organic electronic devices, the efficiency, lifetime, and driving voltage of the organic electronic device may vary depending on which organic materials are combined and used in a particular layer. Summary of the invention

[0007] Technical issues

[0008] Embodiments of the present disclosure may provide an organic electronic device having low driving voltage, high efficiency, high color purity, and extended lifespan.

[0009] Technical Solutions

[0010] In one aspect, an organic electronic device according to an embodiment of the present disclosure includes a first electrode, a second electrode, and an organic material layer.

[0011] The organic material layer is located between the first electrode and the second electrode, and includes a first stack, a second stack, and a third stack.

[0012] The first stack includes a first hole transport region, a first emissive layer, and a first electron transport region.

[0013] The first hole transport region includes a first hole transport layer and a first auxiliary emission layer.

[0014] The first hole transport layer or the first auxiliary emission layer includes a first compound represented by Formula 1 below.

[0015] [Formula 1]

[0016]

[0017] Beneficial Effects

[0018] Embodiments of the present disclosure may provide an organic electronic device in which high luminous efficiency, low driving voltage, high thermal resistance, significantly improved color purity, and significantly extended lifespan are achieved. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 is a diagram schematically showing an organic electronic device according to an embodiment of the present disclosure;

[0020] Figure 2 is a diagram schematically showing a first hole transport layer of an organic electronic device according to an embodiment of the present disclosure;

[0021] Figure 3 and Figure 4 is a diagram schematically showing an organic electronic device according to an embodiment of the present disclosure; and

[0022] Figure 5 is a diagram schematically showing a stack of an organic electronic device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0023] Hereinafter, embodiments of the present disclosure will be described in detail with reference to the illustrative drawings.

[0024] When the elements of the drawings are represented by reference numerals, the same elements will be represented by the same reference numerals, even though they are shown in different drawings. In addition, in the following description of the present disclosure, in the case where the subject matter of the present disclosure may become unclear due to the detailed description of the known functions and configurations combined herein, the detailed description will be omitted. It should be understood that, unless clearly stated to the contrary, the terms "including", "having", "consisting of..." and any variations thereof used in this article are intended to cover non-exclusive inclusion. Unless clearly stated to the contrary, the description of the elements in the singular form used herein should include the description of the elements in the plural form.

[0025] In addition, when describing the elements of the present disclosure, terms such as first, second, A, B, (a) or (b) may be used herein. Each of these terms is not used to define the nature, order or sequence of the corresponding elements, but is only used to distinguish the corresponding elements from other elements.

[0026] It should be understood that when an element is referred to as being “connected,” “coupled,” or “engaged” to another element, the element may not only be “directly connected, coupled, or engaged” to the other element, but may also be “indirectly connected, coupled, or engaged” to the other element through an “intermediary” element. Here, the intermediary element may be included in one or more of the two elements that are “connected,” “coupled,” or “engaged” to each other.

[0027] In addition, it should be understood that when an element such as a layer, film, region, or plate is referred to as being “on” or “over” another element, the element may not only be “directly” on or over the other element, but may also be “indirectly” on or over the other element or layer through an “intermediary” element. In contrast, when an element is referred to as being “directly” on or over another element, it should be understood that there is no intervening intermediary element.

[0028] Unless the terms "directly" or "immediately" are used together, when time-related terms (such as "after", "following", "next", "before", etc.) are used to describe elements, operations, or manufacturing methods, etc., these terms may be used to describe non-continuous or non-sequential processes or operations.

[0029] Furthermore, when referring to any numerical value of an element or corresponding information, the numerical value of the element or corresponding information should be considered to include a tolerance or error range that may be caused by various factors (e.g., process factors, internal or external influences, noise, etc.), even when no relevant description is specified.

[0030]

[0046] Unless otherwise indicated, the term "halo" or "halogen" as used herein refers to fluorine (F), chlorine (Cl), bromine (Br), iodine (I) and the like.

[0031] Unless otherwise indicated, the term "alkyl" or "alkyl group" as used herein may have single bonds of 1 to 60 carbon atoms, and refers to a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0032] Unless otherwise indicated, the term "haloalkyl" or "haloalkyl" as used herein may include halogen-substituted alkyl groups.

[0033] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein may have a double bond or a triple bond of 2 to 60 carbon atoms, and include a straight chain group or a branched chain group.

[0034] Unless otherwise specified, the term "cycloalkyl group" as used herein may refer to an alkyl group forming a ring having 3 to 60 carbon atoms.

[0035] The term "alkoxy group" or "alkoxy" as used herein refers to an alkyl group bonded to an oxy group, and unless otherwise specified, may have 1 to 60 carbon atoms.

[0036] The term "alkenyloxy group," "alkenyloxy," "alkenoxy group," or "alkenoxy group" refers to an alkenyl group to which is attached an oxy group and, unless otherwise specified, may have from 2 to 60 carbon atoms.

[0037] Unless otherwise indicated, the term "aryl group" or "arylene group" as used herein has, but is not limited to, 6 to 60 carbon atoms. Here, the aryl group or arylene group may include monocyclic compounds, ring components, fused polycyclic systems, spirocyclic compounds, etc. For example, the aryl group includes, but is not limited to, phenyl groups, biphenyl groups, naphthyl groups, anthracenyl groups, indenyl groups, phenanthrenyl groups, triphenylene groups, pyrenyl groups, peryl groups, chrysenyl groups, tetraphenylene groups, fluoranthenyl groups, etc. Naphthyl groups may include 1-naphthyl groups and 2-naphthyl groups, and anthracenyl groups may include 1-anthracenyl groups, 2-anthracenyl groups, and 9-anthracenyl groups.

[0038] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein may refer to a monovalent or divalent functional group of fluorene. In addition, a "fluorenyl group" or "fluorenylene group" may refer to a substituted fluorenyl group or a substituted fluorenylene group. A "substituted fluorenyl group" or "substituted fluorenylene group" may refer to a monovalent or divalent functional group of a substituted fluorene. The term "substituted fluorene" may refer to a compound in which at least one of the following substituents R, R', R", or R'" is a functional group other than hydrogen, and includes a case in which R and R' are bonded to each other to form a spiro compound together with the carbon atom bonded thereto.

[0039]

[0040] The term "spiro compound" as used herein has a "spiro union", which refers to a knot in which two rings share only one atom. In this case, the atom shared by the two rings is called a "spiro atom". Depending on the number of spiro atoms contained in the compound, such spiro compounds are called, for example, "monospiro", "bispiro" and "trispiro" compounds.

[0041] As used herein, the term "heterocyclyl group" includes not only aromatic rings, such as "heteroaryl groups" or "heteroarylene groups", but also non-aromatic rings, and unless otherwise specified, refers to, but is not limited to, monocyclic and polycyclic rings, each ring including one or more heteroatoms and having 2 to 60 carbon atoms. Unless otherwise specified, the term "heteroatom" as used herein refers to N, O, S, P, or Si. "Heterocyclic group" may refer to monocyclic compounds, ring assemblies, fused polycyclic systems, spirocyclic compounds, etc., containing heteroatoms.

[0042] In addition, as used herein, the "heterocyclic group" may include a ring in which a ring-forming carbon atom is replaced by SO2. For example, the "heterocyclic group" may include the following compounds.

[0043]

[0044] The term "ring" as used herein may refer to a monocyclic ring and a polycyclic ring, including not only a hydrocarbon ring but also a heterocyclic ring including at least one heteroatom, and including an aromatic ring and a non-aromatic ring.

[0045] As used herein, the term "polycyclic ring" may include ring assemblies, fused polycyclic ring systems, and spirocyclic compounds. Polycyclic rings may include not only aromatic compounds but also non-aromatic compounds, and not only hydrocarbon rings but also heterocyclic rings containing at least one heteroatom.

[0046] The term "aliphatic cyclic group" as used herein may refer to cyclic hydrocarbons other than aromatic hydrocarbons, including a single ring, a ring assembly, a condensed ring system, a spiro compound, etc., and unless otherwise specified, refers to a ring each having 3 to 60 carbon atoms. For example, a condensed system of benzene as an aromatic ring and cyclohexane as a non-aromatic ring corresponds to an aliphatic ring.

[0047] As used herein, the term "ring assembly" refers to a compound in which two or more rings (monocyclic or fused ring systems) are directly connected by a single bond or a double bond. For example, in an aryl group, the ring assembly can be, but is not limited to, a biphenyl group, a terphenyl group, and the like.

[0048] As used herein, the term "fused polycyclic ring system" refers to a fused ring form that shares at least two atoms. For example, in an aryl group, the fused polycyclic ring system can be, but is not limited to, a naphthyl group, a phenanthrenyl group, a fluorenyl group, and the like.

[0049] In addition, in the case where the prefixes are named consecutively, this means that the substituents are listed in the order of the prefixes. For example, an arylalkoxy group may refer to an alkoxy group substituted by an aryl group, an alkoxycarbonyl group may refer to a carbonyl group substituted by an alkoxy group, and an arylcarbonylalkenyl group may refer to an alkenyl group substituted by an arylcarbonyl group. Here, an arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0050] Unless otherwise specifically stated, the term "substituted or unsubstituted" as used herein may refer to, but is not limited to, deuterium, halogen, an amino group, a nitrile group, a nitro group, a C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C1-C 20 Alkylamino groups, C1-C 20 Alkylthiophene, C6-C 20 Arylthiophene group, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 25 Aryl groups, deuterated C6-C 25 Aryl group, C8-C 20 an arylalkenyl group, a silane group, a boron group, a germanium group, and a C2-C4-H2O group containing at least one heteroatom selected from the group consisting of O, N, S, Si, or P. 20 Heterocyclic group.

[0051] In this article, the "name of the functional group" corresponding to the aryl group, arylene group, heterocyclic group, etc. and its substituent as shown by each symbol can be written as "the name of the functional group reflecting its valence", or can be written as "the name of its parent compound". For example, phenanthrene (i.e., a type of aryl group) can be written as a group name by distinguishing valence. That is, a monovalent phenanthrene "group" can be written as "phenanthrene (group)", and a divalent phenanthrene "group" can be written as "phenanthrene (group)". Alternatively, the phenanthrene group can be written as "phenanthrene", the name of the parent compound, regardless of valence. Similarly, pyrimidine can be written as "pyrimidine" regardless of valence, or can be written as a group name corresponding to each valence, wherein a monovalent pyrimidine group is written as pyrimidinyl (group), and a divalent pyrimidine group is written as pyrimidinylen (group). Thus, when the type of substituent is written as the name of a parent compound herein, the written name may refer to an n-valent "group" formed by desorbing a carbon atom and / or heteroatom-bonded hydrogen atom from the parent compound.

[0052] Furthermore, unless otherwise specifically stated, the formulae used herein may be applied in the same manner as the definition of substituents defined based on the indices of the following formulae.

[0053]

[0054] Here, when a is 0, the substituent R 1 does not exist. This means that all hydrogens are bonded to carbons of the benzene ring. In this case, the hydrogens bonded to the carbons may not be shown, and the chemical formula or compound may be described. When a is 1, one substituent R 1 When a is 2 or 3, the substituent R 1 When a is 4 to 6, the substituent R 1 When a is an integer equal to or greater than 2, R 1 Can be the same or different.

[0055]

[0056] Here, the substituents bonded to form a ring refer to adjacent groups bonded to each other to form a single ring or two or more condensed rings. The single ring or two or more condensed rings formed in this way may also include a heterocycle containing at least one heteroatom, and include aromatic rings and non-aromatic rings.

[0057] Herein, an organic electronic device may refer to one or more compounds between an anode and a cathode, or an organic light-emitting diode (OLED) including an anode, a cathode, and one or more compounds between the anode and the cathode.

[0058] In addition, in this article, in some cases, an organic electronic device may refer to an OLED or a panel having an OLED thereon, or an electronic device including a panel and a circuit. For example, the electronic device may be, but is not limited to, a display device, a lighting device, a solar cell, a portable or mobile terminal (e.g., a smart phone, a tablet computer, a personal digital assistant (PDA), an electronic dictionary, or a portable media player (PMP)), a navigation terminal, a game console, various TVs, and various computer displays. The electronic device may be any type of device including the above components.

[0059] Figure 1 is a diagram schematically showing an organic electronic device according to an embodiment of the present disclosure.

[0060] The organic electronic device 100 according to the embodiment includes a first electrode 110 , a second electrode 120 , and an organic material layer 130 located between the first electrode 110 and the second electrode 120 and including a first stack 141 , a second stack 142 , and a third stack 143 .

[0061] Although Figure 1 An embodiment is shown in which the second stack 142 is located above the first stack 141 and the third stack 143 is located above the second stack 142 , but embodiments of the present disclosure are not limited thereto.

[0062] For example, the first electrode 110 may be an anode, and the second electrode 120 may be a cathode. The organic material layer 130 is a layer located between the first electrode 110 and the second electrode 120 and including an organic material. The organic material layer 130 may be composed of a plurality of layers.

[0063] In one example, the first electrode 110 may be a transparent electrode, and the second electrode 120 may be a reflective electrode. In another example, the first electrode 110 may be a reflective electrode, and the second electrode 120 may be a transparent electrode.

[0064] Since the organic material layer 130 includes at least three stacks, the organic electronic device according to the embodiment may be, for example, a tandem organic electronic device including a plurality of stacks. The organic material layer may be implemented by repeatedly stacking the same stack three or more times or stacking three or more different stacks.

[0065] The three or more stacks may include a first stack 141 , a second stack 142 , and a third stack 143 .

[0066] The first stack 141 includes a first hole transport region 1411 , a first emission layer 1412 , and a first electron transport region 1413 .

[0067] The first emission layer 1412 is a layer that emits light energy generated by electron-hole recombination. For example, the first emission layer 1412 may include a host material and a dopant.

[0068] The first hole transport region 1411 may be, for example, a region located between the first electrode 110 serving as an anode and the first emission layer 1412 to transport holes from the first electrode 110 to the first emission layer 1412. The first electron transport region 1413 may be, for example, a region located between the second electrode 120 serving as a cathode and the first emission layer 1412 to transport electrons from the second electrode 120 to the emission layer.

[0069] The first hole transport region 1411 may include a P-type dopant, and the first electron transport region 1413 may include an N-type dopant. Here, the P-type doped layer refers to a layer doped with a P-type dopant to have a more positive characteristic than before (i.e., the characteristic of a hole). Conversely, the N-type doped layer refers to a layer doped with an N-type dopant to have a more negative characteristic than before (i.e., the characteristic of an electron).

[0070] The thickness of the first hole transport region 1411 may be 10 nm to 100 nm. The lower limit of the thickness of the first hole transport region 1411 may be, for example, 15 nm or more, or 20 nm or more. The upper limit of the thickness of the first hole transport region 1411 may be, for example, 90 nm or less, or 80 nm or less. When the thickness of the first hole transport region 1411 is within this range, the organic electronic device may have high luminous efficiency, low driving voltage, and extended lifespan.

[0071] The organic material layer 130 may include one or more charge generation layers 150 located between the stacks. The charge generation layer 150 refers to a layer that generates holes and electrons when a voltage is applied thereto. When three or more stacks are provided, the charge generation layer 150 may be located between the stacks. Here, the plurality of charge generation layers 150 may be the same or different from each other. Since the charge generation layer 150 is disposed between the stacks, the current efficiency of each stack in the stack can be improved, and the charges can be appropriately distributed on the stacks.

[0072] Specifically, each of the charge generation layers 150 may be disposed between two adjacent stacks and used to drive a tandem organic light emitting device using only one pair of an anode and a cathode without a separate internal electrode between the stacks.

[0073] The charge generation layer 150 may include, for example, an N-type charge generation layer 151 and a P-type charge generation layer 152. For example, the N-type charge generation layer 151 may be located adjacent to the first electrode 110 serving as an anode, and the P-type charge generation layer 152 may be located adjacent to the second electrode 120 serving as a cathode.

[0074] The capping layer 160 may be located on the second electrode 120. When the capping layer 160 is formed, optical efficiency of the organic electronic device may be improved.

[0075] In a top-emitting organic electronic device, the capping layer 160 may be used to reduce light energy loss in the second electrode 120 caused by surface plasmon polariton (SPP). In a bottom-emitting organic electronic device, the capping layer 160 may be used to buffer the second electrode 120.

[0076] The first hole transport region 1411 includes a first hole transport layer 1411a and a first auxiliary emission layer 1411b. The first auxiliary emission layer 1411b may be located, for example, between the first emission layer 1412 and the first hole transport layer 1411a.

[0077] The first electron transport region 1413 may include an electron transport layer (not shown).

[0078] Figure 2 is a diagram schematically illustrating a first hole transport layer 1411 a of an organic electronic device according to an embodiment of the present disclosure.

[0079] refer to Figure 2 , the thickness Tt of the first hole transport layer 1411a may be defined as the distance between H1 and H3. H1 may be a boundary between the first hole transport layer 1411a and any layer located below the first hole transport layer (e.g., the first electrode). H3 may be a boundary between the first hole transport layer 1411a and any layer located above the first hole transport layer (e.g., the first auxiliary emission layer 1411b).

[0080] The thickness Tt of the first hole transport layer 1411a can be to The lower limit of the thickness Tt of the first hole transport layer 1411a may be, for example, or larger, or The upper limit of the thickness Tt of the first hole transport layer 1411a may be, for example, or smaller or or smaller.

[0081] When the thickness of the first hole transport layer 1411a satisfies the above range, the first hole transport layer 1411a may contain an amount of hole transport material sufficient to have excellent hole injection and transport functions while preventing excessive charge injection, thereby providing an organic electronic device having a low thickness and at the same time excellent in driving voltage, efficiency or lifespan.

[0082] In the first hole transport layer 1411a, 10% to 50% of the thickness Tt of the first hole transport layer may be doped with the first doping material. The portion of the first hole transport layer 1411a doped with the first doping material may be referred to as a first doping material doped layer 1411aa. The first hole transport layer 1411a may include a first doping material doped layer 1411aa doped with the first doping material and a first doping material undoped layer 1411ab not doped with the first doping material. The first doping material undoped layer 1411ab may be located between the first doping material doped layer 1411aa and the first emission layer.

[0083] For example, the first hole transport layer 1411a may include a hole transport material. The first dopant doped layer 1411aa may be a layer including a first dopant material in addition to the hole transport material. There is no particular limitation on the hole transport material as long as it is a material having hole transport properties. For example, the hole transport material may be at least one selected from the first compound or the fourth compound.

[0084] The thickness T1 of the first doping material doped layer 1411aa may be 10% to 50% of the thickness of the first hole transport layer 1411a. The thickness T1 of the first doping material doped layer 1411aa may be defined as a distance between H1 and H2. H2 may be a boundary between the first doping material doped layer 1411aa and the first doping material undoped layer 1411ab.

[0085] The lower limit of the ratio of the thickness T1 of the first doping material doping layer 1411aa to the thickness of the first hole transport layer 1411a may be, for example, 12% or more, or 15% or more. The upper limit of the ratio of the thickness T1 of the first doping material doping layer to the thickness Tt of the first hole transport layer 1411a may be, for example, 40% or less, or 30% or less.

[0086] The thickness T1 of the first doping material doping layer 1411aa may be, for example, to At the same time, the above ratio range relative to the thickness Tt of the first hole transport layer is satisfied. The lower limit of the thickness T1 of the first doping material doping layer 1411aa may be, for example or larger, or or greater, while the upper limit of the thickness T1 of the first doping material doping layer 1411aa may be, for example or smaller, or or smaller.

[0087] When the thickness T1 of the first doping material doping layer 1411aa satisfies the above ratio and thickness range, the generation of holes and charges in the first hole transport layer 1411a can be promoted to promote the injection of holes into the first emission layer 1412, thereby providing an organic electronic device superior in life or efficiency. Therefore, short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0088] The first doping material doping layer may include a first compound, and include 5 to 15 parts by weight of the first doping material with respect to 100 parts by weight of the first compound.

[0089] The first doping material doping layer may include at least one of the first compound or the fourth compound, and may include 5 to 15 parts by weight of the first doping material relative to 100 parts by weight of the total amount of the first compound and the fourth compound. The lower limit of the doping ratio of the first doping material may be, for example, 7 parts by weight or more, or 9 parts by weight or more. The upper limit of the doping ratio of the first doping material may be, for example, 13 parts by weight or less, or 11 parts by weight or less.

[0090] When the doping ratio of the first doping material satisfies the above range, the generation of holes and charges in the first hole transport layer can be promoted to promote the injection of holes into the first emission layer, thereby providing an organic electronic device superior in life or efficiency. Therefore, short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0091] Unless explicitly stated otherwise, what is described above with respect to the first stack 141 may also apply to the second stack 142 and the third stack 143 .

[0092] The second stack 142 may include a second hole transport region, a second emission layer, and a second electron transport region. Unless otherwise explicitly stated, the contents described above for the first hole transport region 1411, the first emission layer 1412, and the first electron transport region 1413 may also apply to the second hole transport region, the second emission layer, and the second electron transport region.

[0093] The second hole transport region may include a second hole transport layer and a second auxiliary emission layer. Unless otherwise explicitly stated, the above descriptions for the first hole transport layer 1411a and the first auxiliary emission layer 1411b may also apply to the second hole transport layer and the second auxiliary emission layer.

[0094] Regarding the thickness and doping of the second hole transport layer, the contents described above with respect to the thickness and doping of the first hole transport layer 1411 a may be equally applicable.

[0095] The thickness of the second hole transport layer may be to The lower limit of the thickness of the second hole transport layer may be, for example or larger, or The upper limit of the thickness of the second hole transport layer may be, for example, or smaller, or or smaller.

[0096] When the thickness of the second hole transport layer satisfies the above range, the second hole transport layer may include a hole transport material in an amount sufficient to have excellent hole injection and transport functions and prevent charges from being excessively injected, thereby providing an organic electronic device having a low thickness and at the same time being excellent in driving voltage, efficiency or lifespan.

[0097] In the second hole transport layer, 10% to 50% of the thickness of the second hole transport layer may be doped with the second doping material. The portion of the second hole transport layer doped with the second doping material may be referred to as a second doping material doped layer. The second hole transport layer may include a second doping material doped layer doped with the second doping material and a second doping material undoped layer not doped with the second doping material. The second doping material undoped layer may be located between the second doping material doped layer and the second emission layer.

[0098] For example, the second hole transport layer may include a hole transport material. The second doping material doped layer may be a layer including a second doping material in addition to the hole transport material. There is no particular limitation on the transport material as long as it is a material having hole transport properties. For example, the hole transport material may be a second compound.

[0099] The thickness of the second doping material doped layer may be 10% to 50% of the thickness of the second hole transport layer. The lower limit of the ratio of the thickness of the second doping material doped layer to the thickness of the second hole transport layer may be, for example, 12% or more, or 15% or more. The upper limit of the ratio of the thickness of the second doping material doped layer to the thickness of the second hole transport layer may be, for example, 40% or less, or 30% or less.

[0100] The thickness of the second doping material doping layer may be, for example, to At the same time, the above ratio range relative to the thickness of the second hole transport layer is satisfied. The lower limit of the thickness of the second doping material doped layer can be, for example or larger, or or greater, while the upper limit of the thickness of the second doping material doping layer may be, for example or smaller, or or smaller.

[0101] When the thickness of the second doping material doping layer satisfies the above ratio and thickness range, the generation of holes and charges in the second hole transport layer can be promoted to promote the injection of holes into the second emission layer, thereby providing an organic electronic device superior in life or efficiency. Short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0102] The second doping material doping layer may include the second compound, and include 5 to 15 parts by weight of the second doping material with respect to 100 parts by weight of the second compound.

[0103] The second doping material doping layer may include a second compound and include 5 to 15 parts by weight of the second doping material relative to 100 parts by weight of the second compound. The lower limit of the doping ratio of the second doping material may be, for example, 7 parts by weight or more, or 9 parts by weight or more. The upper limit of the doping ratio of the second doping material may be, for example, 13 parts by weight or less, or 11 parts by weight or less.

[0104] When the doping ratio of the second doping material satisfies the above range, the generation of holes and charges in the second hole transport layer can be promoted to promote the injection of holes into the second emission layer, thereby providing an organic electronic device superior in life or efficiency. Short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0105] The third stack 143 may include a third hole transport region, a third emission layer, and a third electron transport region. Unless otherwise explicitly stated, the contents described above for the first hole transport region 1411, the first emission layer 1412, and the first electron transport region 1413 may also apply to the third hole transport region, the third emission layer, and the third electron transport region.

[0106] The third hole transport region may include a third hole transport layer and a third auxiliary emission layer. Unless otherwise explicitly stated, the above descriptions for the first hole transport layer 1411a and the first auxiliary emission layer 1411b may also apply to the third hole transport layer and the third auxiliary emission layer.

[0107] Regarding the thickness and doping of the third hole transport layer, the contents described above with respect to the thickness and doping of the first hole transport layer 1411 a may be equally applicable.

[0108] The thickness of the third hole transport layer can be to The lower limit of the thickness of the third hole transport layer may be, for example or larger, or The upper limit of the thickness of the third hole transport layer may be, for example, or smaller, or or smaller.

[0109] When the thickness of the third hole transport layer satisfies the above range, the third hole transport layer may include a hole transport material in an amount sufficient to have excellent hole injection and transport functions and prevent charges from being excessively injected, thereby providing an organic electronic device having a low thickness and at the same time excellent in driving voltage, efficiency or lifespan.

[0110] In the third hole transport layer, 10% to 50% of the thickness of the third hole transport layer may be doped with the third doping material. The portion of the third hole transport layer doped with the third doping material may be referred to as a third doping material doped layer. The third hole transport layer may include a third doping material doped layer doped with the third doping material and a third doping material undoped layer not doped with the third doping material. The third doping material undoped layer may be located between the third doping material doped layer and the third emission layer.

[0111] For example, the third hole transport layer may include a hole transport material. The third doping material doped layer may be a layer including a third doping material in addition to the hole transport material. There is no particular limitation on the transport material as long as it is a material having hole transport properties. For example, the hole transport material may be at least one of the first compound or the fourth compound.

[0112] The thickness of the third doping material doped layer may be 10% to 50% of the thickness of the third hole transport layer. The lower limit of the ratio of the thickness of the third doping material doped layer to the thickness of the third hole transport layer may be, for example, 12% or more, or 15% or more. The upper limit of the ratio of the thickness of the third doping material doped layer to the thickness of the third hole transport layer may be, for example, 40% or less, or 30% or less.

[0113] The thickness of the third doping material doping layer may be, for example, to At the same time, the above ratio range relative to the thickness of the third hole transport layer is satisfied. The lower limit of the thickness of the third doping material doped layer can be, for example or larger, or or greater, while the upper limit of the thickness of the third doping material doping layer may be, for example or smaller, or or smaller.

[0114] When the thickness of the third doping material doping layer satisfies the above ratio and thickness range, the generation of holes and charges in the third hole transport layer can be promoted to promote the injection of holes into the third emission layer, thereby providing an organic electronic device superior in life or efficiency. Short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0115] The third doping material doping layer may include a third compound, and include 5 to 15 parts by weight of the third doping material with respect to 100 parts by weight of the third compound.

[0116] The third doping material doping layer may include a third compound, and may include 5 to 15 parts by weight of the third doping material relative to 100 parts by weight of the third compound. The lower limit of the doping ratio of the third doping material may be, for example, 7 parts by weight or more, or 9 parts by weight or more. The upper limit of the doping ratio of the third doping material may be, for example, 13 parts by weight or less, or 11 parts by weight or less.

[0117] When the doping ratio of the third doping material satisfies the above range, the generation of holes and charges in the third hole transport layer can be promoted to promote the injection of holes into the third emission layer, thereby providing an organic electronic device superior in life or efficiency. Short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0118] Figure 3 is a diagram schematically showing an organic electronic device according to an embodiment of the present disclosure.

[0119] refer to Figure 3 , the organic material layer of the organic electronic device according to the embodiment of the present disclosure may further include a fourth stack 144 .

[0120] Unless explicitly stated otherwise, with respect to the fourth stack 144 , the contents described above with respect to the first stack 141 may also apply.

[0121] exist Figure 1 In the embodiment shown, the first electrode 110, the first stack 141, the second stack 142, the third stack 143, the fourth stack 144 and the second electrode 120 are sequentially stacked. However, the embodiments of the present disclosure are not limited to such organic electronic devices. The upper and lower positional relationship of the first stack 141 to the fourth stack 144 may be different from Figure 3 The upper and lower positional relationship shown in the figure only requires that the first stack 141 to the fourth stack 144 are located between the first electrode 110 and the second electrode 120 .

[0122] The fourth stack 144 may include a fourth hole transport region 1441, a fourth emission layer 1442, and a fourth electron transport region 1443. Unless otherwise explicitly stated, the contents described above for the first hole transport region 1411, the first emission layer 1412, and the first electron transport region 1413 may be equally applicable with respect to the fourth hole transport region 1441, the fourth emission layer 1442, and the fourth electron transport region.

[0123] The fourth hole transport region 1441 may include a fourth hole transport layer 1441a and a fourth auxiliary emission layer 1441b. Unless otherwise specifically stated, the contents described above for the first hole transport layer 1411a and the first auxiliary emission layer 1411b may also apply to the fourth hole transport layer 1441a and the fourth auxiliary emission layer 1441b.

[0124] Unless explicitly stated otherwise, regarding the thickness and doping of the fourth hole transport layer 1441 a , the contents described above with respect to the thickness and doping of the first hole transport layer 1411 a may be equally applicable.

[0125] The thickness of the fourth hole transport layer 1441a may be to The lower limit of the thickness of the fourth hole transport layer 1441a may be, for example or larger, or The upper limit of the thickness of the fourth hole transport layer 1441a may be, for example, or smaller, or or smaller.

[0126] When the thickness of the fourth hole transport layer 1441a satisfies the above range, the fourth hole transport layer 1441a may include a hole transport material in an amount sufficient to have excellent hole injection and transport functions and prevent excessive charge injection, thereby providing an organic electronic device having a low thickness and at the same time excellent in driving voltage, efficiency or lifespan.

[0127] In the fourth hole transport layer 1441a, 10% to 50% of the thickness of the fourth hole transport layer 1441a may be doped with the fourth doping material. The portion of the fourth hole transport layer 1441a doped with the fourth doping material may be referred to as a fourth doping material doped layer. The fourth hole transport layer 1441a may include a fourth doping material doped layer doped with the fourth doping material and a fourth doping material undoped layer not doped with the fourth doping material. The fourth doping material undoped layer may be located between the fourth doping material doped layer and the fourth emission layer.

[0128] For example, the fourth hole transport layer may include a hole transport material. The fourth doping material doped layer may be a layer including a fourth doping material in addition to the hole transport material. There is no particular limitation on the transport material as long as it is a material having hole transport properties. For example, the hole transport material may be at least one of the fifth compound or the sixth compound.

[0129] The thickness of the fourth doping material doped layer may be 10% to 50% of the thickness of the fourth hole transport layer. The lower limit of the ratio of the thickness of the fourth doping material doped layer to the thickness of the fourth hole transport layer 1441a may be, for example, 12% or more, or 15% or more. The upper limit of the ratio of the thickness of the fourth doping material doped layer to the thickness of the fourth hole transport layer 1441a may be, for example, 40% or less, or 30% or less.

[0130] The thickness of the fourth doping material doped layer may be, for example to At the same time, the above ratio range relative to the thickness of the fourth hole transport layer 1441a is satisfied. The lower limit of the thickness of the fourth doping material doped layer can be, for example or larger, or or greater, while the upper limit of the thickness of the fourth doping material doping layer may be, for example or smaller, or or smaller.

[0131] When the thickness of the fourth doping material doping layer satisfies the above ratio and thickness range, the generation of holes and charges in the fourth hole transport layer 1441a can be promoted to promote the injection of holes into the fourth emission layer 1442, thereby providing an organic electronic device superior in life or efficiency. Short circuit problems in the device can be prevented, and the manufacturing cost can be prevented from increasing due to excessive use of doping materials.

[0132] Figure 4 is a diagram schematically showing an organic electronic device according to an embodiment of the present disclosure.

[0133] The organic electronic device 200 according to the embodiment includes a first electrode 210 , a second electrode 230 , and an organic material layer 220 located between the first electrode 210 and the second electrode 230 and including at least two stacks 240 .

[0134] For example, the first electrode 210 may be an anode, and the second electrode 230 may be a cathode. The organic material layer 220 is a layer located between the first electrode 210 and the second electrode 230 and including an organic material. The organic material layer 220 may be composed of a plurality of layers.

[0135] In one example, the first electrode 210 may be a transparent electrode, and the second electrode 230 may be a reflective electrode. In another example, the first electrode 210 may be a reflective electrode, and the second electrode 230 may be a transparent electrode.

[0136] Since the organic material layer 220 includes at least two stacks, the organic electronic device according to the embodiment may be, for example, a tandem organic electronic device including a plurality of stacks. The organic material layer may be implemented by repeatedly stacking the same stack two or more times or by stacking two or more different stacks.

[0137] Each of the three or more stacks 240 includes a hole transport region 241, an emission layer 242, and an electron transport region 243. The hole transport region 241 may be, for example, a region located between the first electrode 210 used as an anode and the emission layer 242 to transport holes from the first electrode 210 to the emission layer 242. The electron transport region 243 may be, for example, a region located between the second electrode 230 used as a cathode and the emission layer 242 to transport electrons from the second electrode 230 to the emission layer.

[0138] The emission layer 242 is a layer in which energy generated by electron-hole recombination is emitted as light. For example, the emission layer 242 may include a host material and a dopant.

[0139] The thickness of the hole transport region may be 10 nm to 100 nm. The lower limit of the thickness of the hole transport region may be, for example, 15 nm or more, or 20 nm or more. The upper limit of the thickness of the hole transport region may be, for example, 80 nm or less, or 60 nm or less. When the thickness of the hole transport region is within this range, the organic electronic device may have high luminous efficiency, low driving voltage, and extended lifespan.

[0140] The organic material layer 220 may include one or more charge generation layers 250 located between the stacks 240. When three or more stacks 240 are provided, the charge generation layer 250 may be located between the stacks 240. Here, the plurality of charge generation layers 250 may be the same as or different from each other. Since the charge generation layer 250 is disposed between the stacks, the current efficiency of each stack in the stack can be improved, and the charges can be appropriately distributed on the stacks.

[0141] The charge generation layer 250 may include, for example, an N-type charge generation layer 251 and a P-type charge generation layer 252. For example, the N-type charge generation layer 251 may be located adjacent to the first electrode 210 serving as an anode, and the P-type charge generation layer 252 may be located adjacent to the second electrode 230 serving as a cathode.

[0142] The charge generation layer 250 and the stack 240 may be repeatedly positioned n times, where n is a positive integer. For example, n may be an integer from 1 to 5. For example, when n is 2, the organic material layer may include three stacks and two charge generation layers.

[0143] The capping layer 260 may be located on the second electrode 230. When the capping layer 260 is formed, optical efficiency of the organic electronic device may be improved.

[0144] In a top-emitting organic electronic device, the capping layer 260 may be used to reduce light energy loss in the second electrode 230 caused by SPP. In a bottom-emitting organic electronic device, the capping layer 260 may be used to buffer the second electrode 230.

[0145] In the hole transport region 241 of each stack of the plurality of stacks 240, at least one hole transport region 241 includes a first hole transport layer and a second hole transport layer. For example, when the organic material layer includes two stacks, one of the two hole transport layers in the two stacks may include a first hole transport layer and a second hole transport layer, or each of the two hole transport layers may include a first hole transport layer and a second hole transport layer.

[0146] Figure 5 is a diagram schematically illustrating a stack 240 according to an embodiment of the present disclosure.

[0147] refer to Figure 5 , at least one hole transport region 241 may include a first hole transport layer 244 and a second hole transport layer 245. For example, the first hole transport layer 244 and the second hole transport layer 245 may be located in the hole transport region 241 such that the first hole transport layer 244 is located closer to the first electrode 210 than the second hole transport layer 245, and the second hole transport layer 245 is located closer to the second electrode 230 than the first hole transport layer 244. In addition, the second hole transport layer 245 may be located closer to the emission layer 242 than the first hole transport layer 244.

[0148] although Figure 5 Although not shown in the figure, the hole transport region 241 may further include a third hole transport layer (not shown). The third hole transport layer may be located, for example, between the first hole transport layer 244 and the second hole transport layer 245. In the above illustration, the first hole transport layer 244 may be located closer to the first electrode 210 than the second hole transport layer 245, the second hole transport layer 245 may be located closer to the emission layer 242 than the first hole transport layer 244, and the third hole transport layer may be located between the first hole transport layer 244 and the second hole transport layer 245.

[0149] The electron transport region 243 may include an electron transport layer 248 .

[0150] The first hole transport layer may include a seventh compound. The seventh compound may include a compound group represented by Formula A described below, and may be represented by Formula C or Formula D described below. The second hole transport layer may include an eighth compound. The eighth compound may include a compound group represented by Formula A or Formula B described below, and may be represented by Formula C or Formula D described below.

[0151] Since the first hole transport layer includes the seventh compound and the second hole transport layer includes the eighth compound, the luminous efficiency, lifespan, driving voltage, and color purity of the organic electronic device may be further improved.

[0152] The third hole transport layer may include a ninth compound. The ninth compound includes a compound group represented by Formula A or Formula B described below, and is represented by Formula C or Formula D described below. In addition, the ninth compound is different from the eighth compound. When the hole transport region 241 further includes the third hole transport layer, the luminous efficiency, lifespan, driving voltage and color purity of the organic electronic device can be further improved.

[0153] The first hole transport layer including the seventh compound may mean including one or more types of the seventh compound. For example, the first hole transport layer may include two different types of the seventh compound.

[0154] The second hole transport layer including the eighth compound may mean including one or more types of the eighth compound. For example, the second hole transport layer may include two different types of the eighth compound.

[0155] The third hole transport layer including the ninth compound may mean including one or more types of the ninth compound. For example, the third hole transport layer may include two different types of ninth compounds.

[0156] The organic electronic device according to an embodiment of the present disclosure may be a top emission organic electronic device, a bottom emission organic electronic device, or a dual emission organic electronic device depending on the materials used.

[0157] The advantage of a white organic light emitting device (WOLED) is that high resolution can be easily achieved and processability is excellent. In addition, WOLED can be manufactured using conventional color filter technology for liquid crystal displays (LCDs). For white organic electronic devices that are mainly used as backlight units, a variety of structures have been proposed and patents have been applied for. Representatively, there is a side-by-side method in which red (R), green (G), and blue (B) emission units are arranged in a planar direction; a stacking method in which R, G, and B emission layers are stacked in a top-to-bottom direction; a color conversion material (CCM) method using electroluminescence caused by a blue (B) organic emission layer and light from the electroluminescence, using photoluminescence from an inorganic fluorescent material; and the like. The present disclosure can also be applied to such WOLEDs.

[0158] The first hole transport layer 1411a or the first auxiliary emission layer 1411b may include a first compound represented by the following Formula 1. In another example, the first hole transport layer 1411a and the first auxiliary emission layer 1411b may include a first compound represented by the following Formula 1.

[0159] [Formula 1]

[0160]

[0161] Hereinafter, Formula 1 will be described.

[0162] Each of m and n is independently 0 or 1, wherein m+n is 1.

[0163] Ar 1 and Ar 2 Each of which is selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0164] Ar 1 and Ar 2 Each of which may be selected from the group consisting of: C6-C 60 An aryl group; a fluorenyl group; or a C2-C 60 Heterocyclic group.

[0165] When Ar 1 and Ar 2When one of them is an aryl group, Ar as an aryl group 1 and Ar 2 One of them may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0166] When Ar 1 and Ar 2 When one of them is a heterocyclic group, Ar as a heterocyclic group 1 and Ar 2 One of them may be, for example, a C2-C4-C6-containing heteroatom selected from O, N, S, Si, or P. 40 Heterocyclic group; C2-C 20 or a C2-C4 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, or P. 10 Heterocyclic group.

[0167] Ar 3 and Ar 4 Each of which is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0168] Ar 3 and Ar 4 Each of the above may be independently C6-C 60 Aryl group.

[0169] When Ar 3 and Ar 4 When one of them is an aryl group, Ar as an aryl group 3 and Ar 4 One of them may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0170] L 1 To L 6 Each of the following is independently selected from the group consisting of: a single bond; C6-C 60Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0171] L 1 To L 6 Each of the C6-C 60 or a C2-C arylene group containing at least one O, N, S, Si, or P heteroatom. 60 Heterocyclic group.

[0172] When L 1 To L 6 When one of them is an arylene group, L as the arylene group 1 To L 6 One of them may be, for example, C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group, or C6-C 10 Arylene group.

[0173] When L 1 To L 6 When one of them is a heterocyclic group, L as a heterocyclic group 1 To L 6 One of them may be, for example, a C2-C 40 Heterocyclic group; C2-C 20 or a C2-C ... 10 Heterocyclic group.

[0174] X may be selected from the group consisting of: hydrogen; deuterium; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; or C2-C 20 Alkynyl group.

[0175] X may be selected from the group consisting of: hydrogen; deuterium; C6-C 30Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; or C1-C 30 Alkyl group.

[0176] When X is an aryl group, X as an aryl group can be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0177] When X is a heterocyclic group, X as a heterocyclic group can be, for example, a C2-C4-C6-C8 ... 40 Heterocyclic group; C2-C 20 A heterocyclic group, or a C2-C 10 Heterocyclic group.

[0178] Y when n is 0 is selected from the group consisting of: hydrogen; deuterium; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; or C2-C 20 an alkynyl group, and when n is 1, is selected from the group consisting of: C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0179] When n is 0, Y may be selected from the group consisting of: hydrogen; deuterium; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; or C1-C 30 Alkyl group.

[0180] When n is 1, Y may be selected from the group consisting of: C6-C 60an arylene group; a fluorenyl group; or a C2-C 60 Heterocyclic group.

[0181] When Y is an aryl group, Y as an aryl group can be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0182] When Y is an arylene group, Y as an arylene group can be, for example, C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group, or C6-C 10 Arylene group.

[0183] When Y is a heterocyclic group, Y as a heterocyclic group can be, for example, a C2-C4-C6 ... 40 Heterocyclic group; C2-C 20 A heterocyclic group, or a C2-C 10 Heterocyclic group.

[0184] X and Y may be bonded to form a spiro compound.

[0185] Each of Ring A and Ring B is independently C6-C 10 Aryl group.

[0186] R 1 and R 2 Each of the following is independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group.

[0187] R 1 and R 2Each of the above may be independently selected from the group consisting of: deuterium; C6-C 30 An aryl group; a fluorenyl group; or a C2-C 30 Heterocyclic group.

[0188] When R 1 and R 2 When one of them is an aryl group, R 1 and R 2 One of them may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0189] When R 1 and R 2 When one of them is a heterocyclic group, R 1 and R 2 One of them may be, for example, a C2-C 40 Heterocyclic group; C2-C 20 or a C2-C ... 10 Heterocyclic group.

[0190] a is an integer of 0-7, and b is an integer of 0-8.

[0191] In Formula 1, each of the aryl group, fluorenyl group, heterocyclic group, condensed ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group and fluorenyl group may be further substituted with one or more substituents selected from the group consisting of: deuterium; halogen group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 Cycloalkyl groups.

[0192] Each of the further substituted substituents may be further substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a C1-C 20Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 Cycloalkyl group. These substituents may be bonded to form a ring.

[0193] The first compound may be represented by one of Formula 2 to Formula 5 below.

[0194] [Formula 2]

[0195]

[0196] [Formula 3]

[0197]

[0198] [Formula 4]

[0199]

[0200] [Formula 5]

[0201]

[0202] Hereinafter, Formula 2 to Formula 5 will be described.

[0203] Each of c and d is independently an integer from 0 to 4, and e is an integer from 0 to 5.

[0204] i)R 3 , R 4 , and R 6 Each of the above may be independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group. Or, ii) multiple R 3 , multiple R 4 , and multiple R 6They may be bonded to form a ring.

[0205] R 3 , R 4 , and R 6 Each of the above may be independently selected from the group consisting of: deuterium; C6-C 30 or a C2-C ... 30 Heterocyclic group.

[0206] R 5 Can be selected from the group consisting of: hydrogen; deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group.

[0207] R 5 may be selected from the group consisting of: hydrogen; deuterium; C6-C 30 or a C2-C ... 30 Heterocyclic group.

[0208] When R 3 , R 4 , and R 6 When one of them is an aryl group, R 3 , R 4 , and R 6 One of them may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0209] When R 3 , R 4 , and R 6 When one of them is a heterocyclic group, R 3 , R 4 , and R 6 One of them may be, for example, a C2-C 40Heterocyclic group; C2-C 20 or a C2-C ... 10 Heterocyclic group.

[0210] Ar 1 To Ar 4 , L 1 To L 6 , R 1 , R 2 , a, and b are the same as Ar defined in the description of Formula 1 1 To Ar 4 , L 1 To L 6 , R 1 , R 2 , a, and b are the same.

[0211] The first compound may be represented by one of Formula 6 to Formula 9 below.

[0212] [Formula 6]

[0213]

[0214] [Formula 7]

[0215]

[0216] [Formula 8]

[0217]

[0218] [Formula 9]

[0219]

[0220] Hereinafter, Equation 6 to Equation 9 will be described.

[0221] Z is O, S, NR', or CR'R".

[0222] R' and R" may be respectively and independently selected from the group consisting of: C1-C 30 Alkyl group; C6-C 30 an aryl group; or a C3-C 30 heterocyclic groups, or are bonded separately to form a spirocyclic compound.

[0223] When one of R' and R" is an aryl group, one of R' and R" as an aryl group may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C25 Aryl group, or C6-C 10 Aryl group.

[0224] When one of R' and R" is a heterocyclic group, one of R' and R" as a heterocyclic group can be, for example, a C2-C4-C6 ... 40 Heterocyclic group; C2-C 20 or a C2-C ... 10 Heterocyclic group.

[0225] i)R 7 and R 8 Each of the following may be independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group. Or, ii) multiple R 7 and multiple R 8 They may be bonded to form a ring.

[0226] i)R 7 and R 8 Each of the above may be independently selected from the group consisting of: deuterium; C6-C 30 An aryl group; a fluorenyl group; or a C2-C 30 heterocyclic group, and ii) multiple R 7 and multiple R 8 They may be bonded to form a ring.

[0227] When R 7 and R 8 When one of them is an aryl group, R 7 and R 8 One of them may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0228] When R 7 To R 8 When one of them is a heterocyclic group, R 7 To R 8 One of them may be, for example, a C2-C4-C6-containing heteroatom selected from O, N, S, Si, or P. 40 Heterocyclic group; C2-C 20 or a C2-C4 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, or P. 10 Heterocyclic group.

[0229] f is an integer of 0-4, and g is an integer of 0-3.

[0230] Ar 2 , L 1 To L 3 , Ring A, Ring B, X, Y, R 1 , R 2 , a, and b are the same as Ar defined above in the description of Formula 1 2 , L 1 To L 3 , Ring A, Ring B, X, Y, R 1 , R 2 , a, and b are the same.

[0231] The first compound may be represented by one of Formula 10 to Formula 12 below.

[0232] [Formula 10]

[0233]

[0234] [Formula 11]

[0235]

[0236] [Formula 12]

[0237]

[0238] Hereinafter, Equation 10 to Equation 12 will be described.

[0239] i)R 9 may be independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 aryloxy group, and ii) multiple R 9 Can be bonded to form a ring.

[0240] i)R 9 may be independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; C2-C containing at least one O, N, S, Si, or P heteroatom 30 Heterocyclic group; or C1-C 30 alkyl group, and ii) multiple R 21 , multiple R 22 , multiple R 23 , multiple R 9 May be bonded to form a ring.

[0241] When R 9 When it is an aryl group, R 9 It can be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0242] When R 9 When it is a heterocyclic group, R 9 It may be, for example, a C2-C4-containing heteroatom selected from O, N, S, Si, or P. 40 Heterocyclic group; C2-C 20 or a C2-C4 heterocyclic group containing at least one heteroatom selected from O, N, S, Si, or P. 10 Heterocyclic group.

[0243] Ar 1 ,Ar 3 , L 1 , L 4 , Ring A, Ring B, X, Y, R 1 , R 2 , a, and b are the same as Ar defined above in the description of Formula 1 1 ,Ar 3 , L 1 , L 4 , Ring A, Ring B, X, Y, R 1 , R2 , a, and b are the same.

[0244] The first compound may be one of the following compounds:

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261] When the first hole transport layer 1411a or the first auxiliary emission layer 1411b includes the above-mentioned first compound and the first hole transport layer 1411a satisfies the above-mentioned thickness and doping conditions, an organic electronic device having excellent efficiency or extended lifespan may be provided.

[0262] The second hole transport layer or the second auxiliary emission layer may include the second compound represented by Formula 1. In another example, each of the second hole transport layer and the second auxiliary emission layer may include the second compound represented by Formula 1.

[0263] When the second hole transport layer or the second auxiliary emission layer includes the above-mentioned second compound and the second hole transport layer satisfies the above-mentioned thickness and doping conditions, an organic electronic device having excellent efficiency or extended lifespan may be provided.

[0264] The third hole transport layer or the third auxiliary emission layer may include the third compound represented by Formula 1. In another example, each of the third hole transport layer and the third auxiliary emission layer may include the third compound represented by Formula 1.

[0265] When the third hole transport layer or the third auxiliary emission layer includes the third compound and the third hole transport layer satisfies the above-mentioned thickness and doping conditions, an organic electronic device having excellent efficiency or extended lifespan may be provided.

[0266] The fourth hole transport layer 1441a or the fourth auxiliary emission layer 1441b may include the fifth compound represented by Formula 1. In another example, the fourth hole transport layer 1441a and the fourth auxiliary emission layer 1441b may include the fifth compound represented by Formula 1.

[0267] When the fourth hole transport layer or the fourth auxiliary emission layer includes the fifth compound and the fourth hole transport layer satisfies the above thickness and doping conditions, an organic electronic device having excellent efficiency or extended lifespan may be provided.

[0268] Unless otherwise specifically stated, with respect to the second compound, the third compound, and the fifth compound, what is described above with respect to the first compound may be equally applied.

[0269] In another example, the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include at least one of the first compound or the fourth compound. In another example, the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include at least one of the first compound or the fourth compound.

[0270] When the first hole transport layer 1411a or the first auxiliary emission layer 1411b includes at least one of the first compound or the fourth compound and the first hole transport layer 1411a satisfies the above thickness and doping conditions, an organic electronic device with excellent efficiency or extended lifespan may be provided.

[0271] In another example, the fourth hole transport layer 1441a or the fourth auxiliary emission layer 1441b may include at least one of the fifth compound or the sixth compound. In another example, the fourth hole transport layer 1441a and the fourth auxiliary emission layer 1441b may include at least one of the fifth compound or the sixth compound.

[0272] When the fourth hole transport layer 1441a or the fourth auxiliary emission layer 1441b includes at least one of the fifth compound or the sixth compound and the fourth hole transport layer 1441a satisfies the above thickness and doping conditions, an organic electronic device having excellent efficiency or extended lifespan may be provided.

[0273] The fourth compound may include a compound group represented by the following Formula A or Formula B, and be represented by at least one of the compounds represented by the following Formula C or Formula D.

[0274] [Formula A, Formula B, Formula C, and Formula D]

[0275]

[0276] In the embodiments of the present disclosure, the description that “any compound contains a compound group represented by formula A or formula B, and is represented by formula C or formula D” may mean that the compound has a structure represented by formula C or formula D, and is an n-valent compound group (here, n is an integer equal to or greater than 1) in which one or more of the substituents and bonds in formula C or formula D are represented by formula A or formula B. On the other hand, the description that “any compound contains a compound group represented by formula A or formula B, and is represented by formula C or formula D” may not mean that the compound contains a compound group represented by formula A or formula B in the form of an n-valent group, but may mean that the compound does not contain a compound group represented by formula A or formula B in the form of an n-valent group, but contains a compound group represented by formula A or formula B, which is in a state where the group is covalently bonded to an element of the compound represented by formula C or formula D.

[0277] Hereinafter, Formula A will be described.

[0278] Each of a and b is independently an integer from 0 to 4.

[0279] X is O, S, CR'R", or N-L1-Ar1.

[0280] R1 and R2 are each and independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group. R1 and R2 may be bonded to form a ring.

[0281] When R1 or R2 is an aryl group, R1 or R2 may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C25 Aryl group, or C6-C 10 Aryl group.

[0282] When R1 or R2 is a heterocyclic group, R1 or R2 may be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0283] Each of R' and R" is independently selected from the group consisting of: hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring. R' and R" may be bonded to form a ring.

[0284] When R' or R" is an aryl group, R' or R" can be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0285] When R' or R" is a heterocyclic group, R' or R" can be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0286] L1 is selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0287] When L1 is an arylene group, L1 can be, for example, C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group, or C6-C 10 Arylene group.

[0288] When L1 is a heterocyclic group, L1 can be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C20 Heterocyclic group.

[0289] Ar1 is selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0290] When Ar1 is an aryl group, Ar1 may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0291] When Ar1 is a heterocyclic group, Ar1 may be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0292] Hereinafter, Formula B will be described.

[0293] 1 is an integer from 0 to 5.

[0294] m is an integer from 0 to 4.

[0295] Each of y and z is an integer from 0 to 4, where y+z is not zero (0).

[0296] R a and R b Each of the following is independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group. a and R b They may be respectively bonded to form a ring.

[0297] When R a or R bWhen it is an aryl group, R a or R b It can be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0298] When R a or R b When it is a heterocyclic group, R a or R b It could be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0299] Hereinafter, Formula C will be described.

[0300] n is 1 or 2.

[0301] Ar2 is a compound group represented by formula A or a compound group represented by formula B.

[0302] Each of Ar3 and Ar4 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0303] When Ar3 or Ar4 is an aryl group, Ar3 or Ar4 may be, for example, C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0304] When Ar3 or Ar4 is a heterocyclic group, Ar3 or Ar4 may be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0305] Each of L2 to L4 is independently selected from the group consisting of: a single bond; C6-C 60 an arylene group; a fluorenyl group; or a C2-C 60 Heterocyclic group.

[0306] When one of L2 to L4 is an arylene group, one of L2 to L4 may be, for example, a C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group, or C6-C 10 Arylene group.

[0307] When one of L2 to L4 is a heterocyclic group, one of L2 to L4 can be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0308] Hereinafter, Formula D will be described.

[0309] o is an integer from 1 to 4.

[0310] Each of Ar5 to Ar8 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0311] When one of Ar5 to Ar8 is an aryl group, one of Ar5 to Ar8 can be, for example, a C6-C 60 Aryl group, C6-C 40 Aryl group, C6-C 25 Aryl group, or C6-C 10 Aryl group.

[0312] When one of Ar5 to Ar8 is a heterocyclic group, one of Ar5 to Ar8 can be, for example, a C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0313] Each of L5 to L9 is independently selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 L9 may be a compound group represented by Formula A or a compound group represented by Formula B.

[0314] When one of L5 to L9 is an arylene group, one of L5 to L9 may be, for example, a C6-C 60 Arylene group, C6-C 40 Arylene group, C6-C 25 Arylene group, or C6-C 10 Arylene group.

[0315] When one of L5 to L9 is a heterocyclic group, one of L5 to L9 can be, for example, C2-C 60 Heterocyclic group, C2-C 40 Heterocyclic group, or C2-C 20 Heterocyclic group.

[0316] In Formulae A to D, each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the arylene group and the fluorenyl group may be further substituted by one or more substituents selected from the group consisting of: deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Aralkyl group; or C8-C 20 In addition, the further substituted substituents may be bonded to form a ring. Each of the further substituted substituents may be further substituted by one or more substituents selected from the group consisting of: deuterium; nitro group; nitrile group; halogen group; amino group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20Aralkyl group; or C8-C 20 Furthermore, these substituents may be bonded to form a ring.

[0317] The fourth compound may include a compound group represented by Formula A, represented by Formula C, and represented by one of the following Formulae H-1 to H-5.

[0318] [Formula H-1 and Formula H-2]

[0319]

[0320] [Formula H-3, Formula H-4 and Formula H-5]

[0321]

[0322] In Formulae H-1 to H-5, a, b, n, R1, R2, R', R", Ar1, Ar3, Ar4 and L1 to L4 are the same as a, b, n, R1, R2, R', R", Ar1, Ar3, Ar4 and L1 to L4 defined in the description of Formulae A to D.

[0323] The fourth compound may include a compound group represented by Formula A, represented by Formula D, and represented by one of the following Formulas I-1 to I-3.

[0324] [Formula I-1 and Formula I-2]

[0325]

[0326]

[0327] In Formulas I-1 to I-3, a, b, R1, R2, R', R", Ar5 to Ar8, and L5 to L9 are the same as a, b, R1, R2, R', R", Ar5 to Ar8, and L5 to L9 defined in the description of Formulas A to D.

[0328] The fourth compound may include a compound group represented by Formula A, represented by Formula D, and represented by one of the following Formulas I-4 to I-6.

[0329] [Formula I-4, Formula I-5 and Formula I-6]

[0330]

[0331] In Formulas I-4 to I-6, a, b, R1, R2, R', R", Ar5 to Ar8, and L5 to L9 are the same as a, b, R1, R2, R', R", Ar5 to Ar8, and L5 to L9 defined in the description of Formulas A to D.

[0332] The fourth compound may include a compound group represented by Formula B, represented by Formula C or Formula D, and represented by one of the following Formula J-1 to Formula J-3.

[0333] [Formula J-1 and Formula J-2]

[0334]

[0335]

[0336] In Formula J-1 to Formula J-3, l, m, n, y, z, R a , R b , Ar3 to Ar8 and L5 to L9 and l, m, n, y, z, R defined in the description of Formula A to Formula D a , R b , Ar3 to Ar8 and L5 to L9 are the same.

[0337] Formula H-1 can be represented by the following formula H-1-A or formula H-1-B.

[0338] [Formula H-1-A and Formula H-1-B]

[0339]

[0340] In formula H-1-A and formula H-1-B, a, b, R1, R2, Ar1, Ar3, Ar4, and L1 to L4 are the same as a, b, R1, R2, Ar1, Ar3, Ar4, and L1 to L4 defined in the description of formulas A to D.

[0341] Each of L1 to L8 may be independently represented by one of the following Formulae b-1 to b-13.

[0342] [Formula b-1, formula b-2, formula b-3, formula b-4, formula b-5 and formula b-6]

[0343]

[0344] [Formula b-7, formula b-8, formula b-9 and formula b-10]

[0345]

[0346] [Formula b-11, formula b-12 and formula b-13]

[0347]

[0348] Hereinafter, Formula b-1 to Formula b-13 will be described.

[0349] Y is respectively and independently NL 6 -Ar9 , O, S, or CR d R e .

[0350] L 6 The same as L1 defined in the description of Formulae A to D.

[0351] Ar 9 Ar1 is the same as defined in the description of Formula A to Formula D.

[0352] R d and R e R' and R" are the same as defined in the description of Formulae A to D.

[0353] Each of a", c", d" and e" is independently an integer from 0 to 4, and b" is each and independently an integer from 0 to 6.

[0354] f" and g" are independently integers of 0 to 3, h" is an integer of 0 to 2, and i" is an integer of 0 or 1.

[0355] R 8 To R 10 Each of the following is independently selected from the group consisting of: hydrogen; deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 An aryl group; a fluorenyl group; a C2-C3-C6-pyridinyl group containing at least one heteroatom selected from the group consisting of O, N, S, Si, or P; 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; or -L a -N(R d )(R e ). 8 and R 10 They may be respectively bonded to form a ring.

[0356] L a Selected from the group consisting of: single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 A fused aliphatic ring group; and C3-C 60 Aliphatic hydrocarbon group.

[0357] R d and R e Each of which is independently selected from the group consisting of: C6-C 60 An aryl group; a fluorenyl group; a C2-C3-C6-pyridinyl group containing at least one heteroatom selected from the group consisting of O, N, S, Si, or P; 60 Heterocyclic group; and C6-C 60 Aromatic rings and C3-C 60 A fused ring group of aliphatic rings.

[0358] Z 49 , Z 50 , and Z 51 Each of which is independently CR f or N, Z 49 , Z 50 , or Z 51 At least one of is N.

[0359] R f is selected from the group consisting of: hydrogen; deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 An aryl group; a fluorenyl group; a C2-C3-C6-pyridinyl group containing at least one heteroatom selected from the group consisting of O, N, S, Si, or P; 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy group. The adjacent R 8 and R f May bond to form a ring.

[0360] The fourth compound may include a compound group represented by Formula A, represented by Formula C, and be one or more of the following Compounds 1-1 to 6-35.

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390] The fourth compound may include a compound group represented by Formula A, represented by Formula D, and be one of the following Compounds 7-1 to 10-189.

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401] The fourth compound may include a compound group represented by Formula B, represented by Formula C or Formula D, and be one or more of the following Formula 11-1 to Formula 12-71.

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408] Unless otherwise specifically stated, with respect to the sixth compound, the contents described above with respect to the fourth compound may be equally applied.

[0409] The first doping material can be a P-type dopant. The P-type dopant can be selected from, for example, quinone dimethane compounds, azaindenofluorene dione, azaphenalene, azatriphenylene, I2, metal halides, transition metal halides, metal oxides, metal oxides containing metals from main group 3 or at least one transition metal, transition metal complexes, or complexes of Cu, Co, Ni, Pd, or Pt with ligands, each of which contains at least one oxygen atom as a binding site. In another example, the P-type dopant can be selected from the oxides of rhenium (Re), molybdenum (Mo), and tungsten (W), respectively. For example, the P-type dopant can be selected from Re2O7, MoO3, WO3, or ReO3, respectively.

[0410] In another example, the first doping material may be represented by Formula E below.

[0411] [Formula E]

[0412]

[0413] Hereinafter, Formula E will be described.

[0414] R p1 To R p6 Each of the following may be independently selected from the group consisting of: hydrogen; a halogen group; a nitrile group; a nitro group; -SO2R; -SOR; -SO2NR2; -SO3R; a trifluoromethyl group; -COOR; -CONHR; -CONRR'; C1-C 30 Alkoxy group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 30 Heterocyclic group; Fluorenyl group; C6-C 30 Aryl group; C6-C 30 Aromatic rings and C3-C 30 An aliphatic ring fused group; or -NRR'.

[0415] R and R' may be selected from the group consisting of: C1-C 30 Alkyl group; Fluorenyl group; C6-C 30 Aryl group; C6-C 30 Aromatic rings and C3-C 30 aliphatic ring fused ring group; or a C2-C 30 Heterocyclic group.

[0416] In Formula E, each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, and the alkoxy group may be substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 Cycloalkyl groups.

[0417] In another example, the first doping material may be selected from the following E-1 to E-4.

[0418]

[0419] In another example, the first doping material may be selected from the following E-5 to E-14.

[0420]

[0421] Unless explicitly stated otherwise, with respect to the second to fourth doping materials, the contents described above with respect to the first doping material may also apply.

[0422] In some embodiments of the present disclosure, the organic material layer 130 includes a first stack 141, a second stack 142, and a third stack 143. The first stack 141 may include a first hole transport region 1411, a first emission layer 1412, and a first electron transport region 1413. In these embodiments, the first hole transport region 1411 may include a first hole transport layer 1411a and a first auxiliary emission layer 1411b, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include a first compound represented by Formula 1, and the thickness of the first hole transport layer 1411a may be from to And 10% to 50% of the thickness of the first hole transport layer 1411a may be doped with the first doping material.

[0423] In some embodiments of the present disclosure, the organic material layer 130 may include a first stack 141, a second stack 142, and a third stack 143. The first stack 141 may include a first hole transport region 1411, a first emission layer 1412, and a first electron transport region 1413. In these embodiments, the first hole transport region 1411 may include a first hole transport layer 1411a and a first auxiliary emission layer 1411b, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include a first compound represented by Formula 1, and the thickness of the first hole transport layer 1411a may be from to And 10% to 50% of the thickness of the first hole transport layer 1411a may be doped with the first doping material. In these embodiments, the second stack 142 may include a second hole transport region 1421, a second emission layer 1422, and a second electron transport region 1423. In these embodiments, the second hole transport region 1421 may include a second hole transport layer 1421a and a second auxiliary emission layer 1421b, the second hole transport layer 1421a or the second auxiliary emission layer 1421b may include a second compound represented by Formula 1, and the thickness of the second hole transport layer 1421a may be from to And 10% to 50% of the thickness of the second hole transport layer 1421a may be doped with the second doping material. In these embodiments, the third stack 143 may include a third hole transport region 1431, a third emission layer 1432, and a third electron transport region 1433. In these embodiments, the third hole transport region 1431 may include a third hole transport layer 1431a and a third auxiliary emission layer 1431b, the third hole transport layer 1431a or the third auxiliary emission layer 1431b may include a third compound represented by Formula 1, and the thickness of the third hole transport layer 1431a may be from to And 10% to 50% of the thickness of the third hole transport layer 1431a may be doped with the third doping material.

[0424] In these embodiments, the thickness of the first hole transport layer 1411a may be from to The thickness of the second hole transport layer 1421a can be to And the thickness of the third hole transport layer 1431a can be from to For example, when the first electrode 110, the first stack 141, the second stack 142, the third stack 143 and the second electrode 120 are stacked sequentially, each of the first emission layer 1412, the second emission layer 1422, the first hole transport layer 1411a, the second hole transport layer 1421a and the third hole transport layer 1431a satisfies the above-mentioned thickness range, the third emission layer 1432 includes a blue host and a blue dopant, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b contains a first compound, the second hole transport layer 1421a or the second auxiliary emission layer 1421b contains a second compound, and the third hole transport layer 1431a or the third auxiliary emission layer 1431b contains a third compound, an organic electronic device with excellent efficiency or extended lifespan can be provided.

[0425] In these embodiments, the first hole transport layer 1411a may include a first doping material doped layer 1411aa doped with a first doping material and a first doping material undoped layer 1411ab not doped with the first doping material. The first doping material doped layer 1411aa may include a first compound and include 5 to 15 parts by weight of the first doping material relative to 100 parts by weight of the first compound. The second hole transport layer may include a second doping material doped layer doped with a second doping material and a second doping material undoped layer not doped with the second doping material. The second doping material doped layer may include a second compound and include 5 to 15 parts by weight of the second doping material relative to 100 parts by weight of the second compound. The third hole transport layer may include a third doping material doped layer doped with a third doping material and a third doping material undoped layer not doped with the third doping material. The third doping material doped layer may include a third compound and include 5 to 15 parts by weight of the third doping material relative to 100 parts by weight of the third compound.

[0426] In these embodiments, the first compound, the second compound, and the third compound can be the same compound.

[0427] In some embodiments of the present disclosure, the organic material layer 130 may include a first stack 141, a second stack 142, and a third stack 143. The first stack 141 may include a first hole transport region 1411, a first emission layer 1412, and a first electron transport region 1413. In these embodiments, the first hole transport region 1411 may include a first hole transport layer 1411a and a first auxiliary emission layer 1411b, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include at least one of the first compound or the fourth compound represented by Formula 1, and the thickness of the first hole transport layer 1411a may be from to And 10% to 50% of the first hole transport layer 1411a may be doped with the first doping material.

[0428] In some embodiments of the present disclosure, the organic material layer 130 may include a first stack 141, a second stack 142, a third stack 143, and a fourth stack 144. The first stack 141 may include a first hole transport region 1411, a first emission layer 1412, and a first electron transport region 1413. In these embodiments, the first hole transport region 1411 may include a first hole transport layer 1411a and a first auxiliary emission layer 1411b, the first hole transport layer 1411a or the first auxiliary emission layer 1411b may include a first compound represented by Formula 1, and the thickness of the first hole transport layer 1411a may be from to And 10% to 50% of the first hole transport layer 1411a may be doped with the first doping material. In these embodiments, the fourth stack 144 may include a fourth hole transport region 1441, a fourth emission layer 1442, and a fourth electron transport region 1443. In these embodiments, the fourth hole transport region 1441 may include a fourth hole transport layer 1441a and a fourth auxiliary emission layer 1441b, the fourth hole transport layer 1441a or the fourth auxiliary emission layer 1441b may include at least one of the fifth compound or the sixth compound represented by Formula 1, and the thickness of the fourth hole transport layer 1441a may be from to And 10% to 50% of the fourth hole transport layer 1441a may be doped with the fourth doping material.

[0429] In an embodiment of the present disclosure, at least one of the first emission layer 1412, the second emission layer 1422, or the third emission layer 1432 may be a blue light emission layer. When at least one of the first to third emission layers is a blue light emission layer and the first hole transport layer 1411a or the first auxiliary emission layer 1411b satisfies the above-mentioned thickness and doping conditions while containing the first compound, an organic electronic device superior in efficiency, life, or color purity may be provided.

[0430] Here, the blue light emitting layer may refer to an emission layer that emits light having a wavelength ranging from about 450 nm to about 495 nm when excited by electron-hole recombination therein.

[0431] In an embodiment of the present disclosure, the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 may emit blue light. When the first to third emission layers are blue light emission layers, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b includes the first compound and satisfies the above thickness and doping conditions, an organic electronic device with excellent efficiency, lifespan, or color purity may be provided.

[0432] In an embodiment of the present disclosure, one or both of the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 may be a blue light emission layer, and one or both of the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 may be a green light emission layer. When one or both of the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 are blue light emission layers, one or both of the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 are green light emission layers, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b includes the first compound and satisfies the above-mentioned thickness and doping conditions, an organic electronic device with excellent efficiency, lifespan, or color purity may be provided.

[0433] Here, the green light emitting layer may refer to an emitting layer, each of which emits light having a wavelength ranging from about 495 nm to about 570 nm when excited by electron-hole recombination therein.

[0434] In an embodiment of the present disclosure, two emission layers among the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 may be blue light emission layers, and the remaining one emission layer among the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 may be a green light emission layer. When two emission layers among the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 are blue light emission layers, the remaining one emission layer among the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 is a green light emission layer, and the first hole transport layer 1411a or the first auxiliary emission layer 1411b satisfies the above-mentioned thickness and doping conditions while including the first compound, an organic electronic device having excellent efficiency, lifetime, or color purity may be provided.

[0435] In an embodiment of the present disclosure, when two of the first emission layer 1412, the second emission layer 1422, and the third emission layer 1432 are blue light emission layers and the remaining emission layer is a green light emission layer, the green light emission layer may be located between the two blue light emission layers. When the first hole transport layer 1411a or the first auxiliary emission layer 1411b contains the first compound and satisfies the above thickness and doping conditions, and the first to third emission layers satisfy the above conditions, an organic electronic device having excellent efficiency, lifespan, or color purity may be provided.

[0436] In an embodiment of the present disclosure, at least one of the first emission layer 1412 , the second emission layer 1422 , or the third emission layer 1432 may be a multi-emission layer that emits green light and blue light.

[0437] Here, the multi-emission layer emitting green light and blue light may refer to an emission layer that emits light having a wavelength ranging from about 450 nm to about 570 nm when excited by electron-hole recombination therein.

[0438] When at least one of the first emission layer 1412, the second emission layer 1422 or the third emission layer 1432 is a multi-emission layer that emits green light and blue light and the first hole transport layer 1411a or the first auxiliary emission layer 1411b contains the first compound and satisfies the above-mentioned thickness and doping conditions, an organic electronic device with excellent efficiency, life or color purity can be provided.

[0439] In an embodiment of the present disclosure, two emission layers among the first emission layer 1412 to the fourth emission layer 1442 may be blue light emission layers, and the remaining one emission layer different from the two emission layers may be a green light emission layer. When two emission layers among the first emission layer 1412 to the fourth emission layer 1442 are blue light emission layers, the remaining one emission layer different from the two emission layers is a green light emission layer, and the fourth hole transport layer 1441a or the fourth auxiliary emission layer 1441b satisfies the above-mentioned thickness and doping conditions while including at least one of the fifth compound or the sixth compound, an organic electronic device with excellent efficiency, lifespan or color purity may be provided.

[0440] Hereinafter, the present disclosure will be described in detail with reference to, but not limited to, synthesis examples of compounds for a hole transport layer and preparation examples of an organic electronic device.

[0441] [Synthesis Example]

[0442] According to the present disclosure, a compound represented by Formula C and comprising a compound group represented by Formula A or Formula B (e.g., the fourth compound, the sixth compound, the seventh compound, or the eighth compound described above) is prepared by, but not limited to, reacting one of Sub 1-A to Sub 1-C with Sub 2 as in the following Reaction Formula 1.

[0443] [Reaction 1]

[0444]

[0445] More specifically, Reaction Formula 1 may be represented by, but not limited to, the following Reaction Formulas 2 to 4.

[0446] [Reaction 2]

[0447]

[0448] [Reaction 3]

[0449]

[0450] [Reaction 4]

[0451]

[0452] Synthesis of Sub 1-A

[0453] Sub 1A of Reaction Formula 1 can be synthesized by, but not limited to, the reaction path of the following Reaction Formula 5.

[0454] [Reaction 5]

[0455]

[0456] Synthesis of Sub 1-B

[0457] Sub 1B of Reaction Formula 2 can be synthesized through, but not limited to, the reaction path of the following Reaction Formula 6.

[0458] [Reaction 6]

[0459]

[0460] Synthesis of Sub 1-C

[0461] Sub 1C of Reaction Formula 3 can be synthesized by, but not limited to, the reaction path of the following Reaction Formula 7.

[0462] [Reaction 7]

[0463]

[0464] Synthesis diagram of Sub 1-A-3

[0465]

[0466] Add 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (29.5 g, 80 mmol), 360 ml of THF, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 ml of water, then stir and reflux. When the reaction is complete, extract with ether and water, then dry the organic layer with MgSO4 and concentrate. The resulting organic substance is subjected to silica gel column chromatography and recrystallization to obtain a product in an amount of 22.9 g (72%).

[0467] Sub Synthesis diagram of 1-A-5

[0468]

[0469] After dissolving 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (73.92 g, 200.2 mmol) in 880 ml of THF in a round-bottom flask, 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh3)4 (11.6 g, 10 mmol), K2CO3 (83 g, 600.6 mmol) and 440 ml of water were treated using the same experimental method as in Sub 1-A-3 to obtain a product in an amount of 55.8 g (yield: 70%).

[0470] Sub 1-B-2 Synthesis Example

[0471]

[0472] After dissolving 9H-carbazole (12 g, 71.8 mmol) with nitrobenzene (450 ml) in a round-bottom flask, 4-bromo-4'-iodo-1,1'-biphenyl (38.65 g, 107.6 mmol), Na2SO4 (10.19 g, 71.8 mmol), K2CO3 (9.92 g, 71.8 mmol) and Cu (1.37 g, 21.5 mmol) were added, followed by stirring at 200°C. When the reaction was complete, nitrobenzene was removed by distillation, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4 and concentrated. Then, the resulting compound was subjected to silica gel column chromatography and recrystallization to obtain 21.15 g of the product (yield: 74%).

[0473]

[0474]

[0475]

[0476] [Table 1]

[0477]

[0478]

[0479]

[0480]

[0481] Sub 2 Synthesis Diagram

[0482] Sub 2 of Reaction Formula 1 can be synthesized through, but not limited to, the reaction path of the following Reaction Formula 8.

[0483] [Reaction formula 8]

[0484]

[0485] Sub Synthesis of 2-1

[0486]

[0487] Bromobenzene (37.1 g, 236.2 mmol) was added to a round-bottomed flask and then dissolved with toluene (2200 ml). Then, aniline (20 g, 214.8 mmol), Pd2(dba)3 (9.83 g, 10.7 mmol), P(t-Bu)3 (4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) were added in sequence and then stirred at 100°C. When the reaction was complete, extraction was performed with ether and water, and the organic layer was then dried and concentrated with MgSO4. The resulting compound was subjected to silica gel column chromatography and recrystallization to obtain 28 g of product (yield: 77%).

[0488] Sub Synthesis of 2-80

[0489]

[0490] [1,1'-biphenyl]-4-amine (15 g, 88.64 mmol), 2-bromodibenzo[b,d]thiophene (23.32 g, 88.64 mmol), Pd2(dba)3 (2.43 g, 2.66 mmol), P(t-Bu)3 (17.93 g, 88.64 mmol), NaOt-Bu (17.04 g, 177.27 mmol) and toluene (886 ml) were added to a round-bottom flask, and then the same experimental method as in Sub 2-1 was carried out to obtain 24.61 g of the product (yield: 79%).

[0491] Sub Synthesis of 2-134

[0492]

[0493] [1,1'-biphenyl]-4-amine (15 g, 88.6 mmol), 2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd2(dba)3 (4.06 g, 4.43 mmol), P(t-Bu)3 (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol) and toluene (931 ml) were added to a round-bottom flask, and then the same experimental method as in Sub 2-1 was carried out to obtain 34.9 g of the product (yield: 70%).

[0494] Synthesis Example of Sub 2-222

[0495]

[0496] 3-Bronaphtho[2,3-b]benzofuran (15 g, 50.48 mmol), [1,1'-biphenyl]-4-amine (8.54 g, 50.48 mmol), Pd2(dba)3 (1.39 g, 1.51 mmol), P(t-Bu)3 (10.21 g, 50.48 mmol), NaOt-Bu (9.70 g, 100.96 mmol) and toluene (505 ml) were added to a round-bottom flask, and then the same experimental method as in Sub 2-1 was carried out to obtain 13.82 g of the product (yield: 71%).

[0497] Sub 2 may have, but is not limited to, the following examples.

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504] [Table 2]

[0505]

[0506]

[0507]

[0508]

[0509] Synthesis diagram of final product 1

[0510] Synthesis of 1-54

[0511]

[0512] 1) Synthesis of Inter_A-1

[0513] N-phenyl-[1,1'-biphenyl]-4-amine (11.6 g, 47.3 mmol), toluene (500 ml), 2-(3,5-dibromophenyl)-9-phenyl-9H-carbazole (24.8 g, 52.0 mmol), Pd2(dba)3 (2.4 g, 2.6 mmol), P(t-Bu)3 (1.05 g, 5.2 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added, followed by stirring at 100°C. When the reaction was completed, extraction was performed with CH2Cl2 and water, and then the organic layer was dried with MgSO4 and concentrated. The resulting organic substance was subjected to silica gel column chromatography and recrystallization to obtain 22.8 g of Inter_A-1 (yield: 75%).

[0514] 2) Synthesis of 1-54

[0515] The same experimental method as in Inter_A-1 was carried out on N-phenyldibenzo[b,d]thiophene-2-amine (8 g, 29.05 mmol), Inter_A-1 (20.5 g, 32 mmol), toluene (305 ml), Pd2(dba)3 (1.5 g, 1.6 mmol), P(t-Bu)3 (0.65 g, 3.2 mmol) and NaOH-Bu (8.4 g, 87.2 mmol) to obtain 18 g of product 1 (yield: 74%).

[0516] Synthesis of 2-9

[0517]

[0518] After Sub 2-26 (7 g, 21.8 mmol) was dissolved in toluene (230 ml) in a round-bottom flask, Sub 1-2 (9.54 g, 24 mmol), Pd2(dba)3 (1 g, 1.1 mmol), 50% P(t-Bu)3 (1.1 ml, 2.2 mmol) and NaOt-Bu (6.91 g, 71.9 mmol) were added, and then stirred at 100°C. When the reaction was completed, extraction was performed with CH2Cl2 and water, and then the organic layer was dried with MgSO4 and concentrated. The resulting compound was subjected to silica gel column chromatography and recrystallization to obtain 11.69 g of the product (yield: 84%).

[0519] Synthesis of 3-52

[0520]

[0521] The same experimental method as in Synthesis 2-9 was carried out on 2-bromonaphtho[2,3-b]benzofuran (10 g, 33.65 mmol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-2-amine (11.83 g, 33.65 mmol), Pd2(dba)3 (0.92 g, 1.01 mmol), P(t-Bu)3 (6.81 g, 33.65 mmol), NaOt-Bu (6.47 g, 67.31 mmol) and toluene (337 ml) to obtain 15.28 g of the product (yield: 80%).

[0522] Synthesis of 6-12

[0523]

[0524] 2-Bromo-11,11-dimethyl-11H-benzo[b]fluorene (10 g, 30.94 mmol), N-([1,1'-biphenyl]-4-yl)naphtho[2,3-b]benzofuran-3-amine (11.93 g, 30.94 mmol), Pd2(dba)3 (0.85 g, 0.93 mmol), P(t-Bu)3 (6.26 g, 30.94 mmol), NaOt-Bu (5.95 g, 61.88 mmol) and toluene (309 ml) were subjected to the same experimental method as in Synthesis 2-9 to obtain 15.15 g of the product (yield: 78%).

[0525] Synthesis of 11-4

[0526]

[0527] 1-(4-Bromophenyl)naphthalene (10 g, 35.3 mmol), bis(4-naphth-1-yl)phenyl)amine (14.8 g, 35.31 mmol), Pd2(dba)3 (0.97 g, 1.06 mmol), P(t-Bu)3 (7.14 g, 35.31 mmol), NaOt-Bu (6.79 g, 70.63 mmol) and toluene (353 ml) were subjected to the same experimental method as in Synthesis 2-9 to obtain 16.9 g of the product (yield: 78%).

[0528] [Table 3]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536] [Synthesis Example 2]

[0537] According to the present disclosure, a compound represented by formula D and comprising a compound group of formula A or formula B (e.g., the fourth compound, the sixth compound, the seventh compound, or the eighth compound described above) is prepared by, but not limited to, reacting Sub 3-A to Sub 3-D with Sub 4 as in the following reaction formula 9.

[0538] [Reaction formula 9]

[0539]

[0540] More specifically, Reaction Formula 8 can be represented by, but not limited to, the following Reaction Formulas 10 to 13.

[0541] [Reaction formula 10]

[0542]

[0543] [Reaction formula 11]

[0544]

[0545] [Reaction 12]

[0546]

[0547] [Reaction 13]

[0548]

[0549] Synthesis of Sub 3-A and Sub 3-B

[0550] Sub 3-A and Sub 3-B of Reaction Formula 10 and Reaction Formula 11 can be synthesized through, but not limited to, the reaction paths of the following Reaction Formula 14 and Reaction Formula 15.

[0551] [Reaction 14]

[0552]

[0553] [Reaction 15]

[0554]

[0555] Combination of Sub 3-C and Sub 3-D

[0556] Sub 3-C and Sub 3-D of Reaction Formula 12 and Reaction Formula 13 can be synthesized through, but not limited to, the reaction paths of the following Reaction Formula 16 and Reaction Formula 17.

[0557] [Reaction 16]

[0558]

[0559] [Reaction 17]

[0560]

[0561] 1.Sub 3-1 Synthesis Example

[0562]

[0563] After diphenylamine (15.22 g, 89.94 mmol) as a starting material was dissolved in toluene (750 ml) in a round-bottom flask, Sub 3-1-st (CAS registration number: 669773-34-6) (46.14 g, 134.91 mmol), Pd2(dba)3 (2.47 g, 2.70 mmol), P(t-Bu)3 (1.82 g, 8.99 mmol) and NaOt-Bu (25.93 g, 269.81 mmol) were added, and then stirred at 80°C. When the reaction was completed, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4 and concentrated. Then, the resulting compound was subjected to silica gel column chromatography and recrystallization to obtain 23.61 g of the product (yield: 61%).

[0564] 2.Sub 3-63 Synthesis Example

[0565]

[0566] After adding sub 3-63-st (10 g, 42.18 mmol), Pd2(dba)3 (1.16 g, 1.27 mmol), P(t-Bu)3 (8.53 g, 42.18 mmol), NaOt-Bu (8.11 g, 84.36 mmol) and toluene (422 ml) to N-phenyldibenzo[b,d]furan-4-amine (10.94 g, 42.18 mmol) as the starting material, 13 g of the product was obtained using the synthesis method of Sub 3-1 (yield: 67%).

[0567] 3.Sub 3-157 Synthesis Example

[0568]

[0569] After adding Sub 3-157-st (16.08 g, 95 mmol), Pd2(dba)3 (2.61 g, 2.85 mmol), P(t-Bu)3 (19.22 g, 95 mmol), NaOt-Bu (18.26 g, 190 mmol) and toluene (950 ml) to diphenylamine (25 g, 95 mmol) as the starting material, 24.45 g of the product was obtained using the synthesis method of Sub 3-1 (yield: 65%).

[0570] Sub 3-A to Sub 3-D may have, but are not limited to, the following examples.

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578] [Table 4]

[0579]

[0580]

[0581]

[0582] Sub 4 Synthesis Diagram

[0583] The synthesis method of Sub 4 of Reaction Formula 8 may be the same as that of Sub 2, but is not limited thereto. The compound belonging to Sub 4 may be the same as that of Sub 2, but is not limited thereto.

[0584] Synthesis of final product 2

[0585] After Sub 3 (1 equivalent) was dissolved with toluene in a round-bottom flask, Sub 4 (1 equivalent), Pd2(dba)3 (0.03 equivalent), (t-Bu)3P (0.1 equivalent) and NaOt-Bu (3 equivalents) were stirred at 100°C. When the reaction was completed, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4 and concentrated. Then, the resulting compound was subjected to silica gel column chromatography and recrystallization to obtain the final product 2.

[0586] Some compounds according to the present disclosure are prepared by the synthesis methods disclosed in Korean Patent Nos. 10-1668448 (patented on October 17, 2016) and 10-1789998 (patented on October 19, 2017) of the present applicant.

[0587] 1.10-37 Synthesis Example

[0588]

[0589] N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-2-amine (4.32 g, 12.29 mmol), Pd2(dba)3 (0.34 g, 0.37 mmol), P(t-Bu)3 (0.25 g, 1.23 mmol), NaOt-Bu (3.54 g, 36.87 mmol) and toluene (125 ml) were added to N,N-diphenyldibenzo[b,d]thiophene-3-amine (5.29 g, 12.29 mmol) obtained in the above synthesis, and then 6.81 g of the product was obtained using the synthesis method (yield: 79%).

[0590] 2.7-8 Synthesis Example

[0591]

[0592] N-phenyldibenzo[b,d]thiophene-2-amine (5 g, 18.2 mmol), Pd2(dba)3 (0.5 g, 0.55 mmol), P(t-Bu)3 (0.23 g, 1.1 mmol), NaOt-Bu (5.3 g, 54.6 mmol) and toluene (100 ml) were added to 7-bromo-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (8 g, 18.2 mmol) obtained by the above synthesis, and then 8.9 g of the product was obtained using the above 10-37 synthesis method (yield: 76%).

[0593] 3.10-176 Synthesis Example

[0594]

[0595] Diphenylamine (6.27 g, 37.08 mmol), Pd2(dba)3 (1.02 g, 1.11 mmol), P(t-Bu)3 (7.50 g, 37.08 mmol), NaOt-Bu (7.13 g, 74.15 mmol) and toluene (371 ml) were added to 9-chloro-N-(dibenzo[b,d]thiophene-3-yl)-N-phenyl-[2,4'-bis(dibenzo[b,d]thiophene]-1'-amine (25 g, 37.08 mmol) obtained by the above synthesis, and then 8.9 g of the product was obtained using the above 10-37 synthesis method (yield: 72%).

[0596] 4.12-1 Synthesis Example

[0597]

[0598] Diphenylamine (9.39 g, 55.51 mmol), Pd2(dba)3 (1.52 g, 1.67 mmol), P(t-Bu)3 (11.23 g, 55.51 mmol), NaOt-Bu (10.67 g, 111.02 mmol) and toluene (555 ml) were added to N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalene-1-amine (25 g, 55.51 mmol) obtained by the above synthesis, and then 21.77 g of the product was obtained using the above 10-37 synthesis method (yield: 81%).

[0599] Meanwhile, the FD-MS values ​​of compounds 7-1 to 12-63 prepared according to the Synthesis Examples of the present disclosure as described above are shown in Table 5 below.

[0600] [Table 5]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606] Evaluation of organic electronic device manufacturing

[0607] When the organic electronic device according to the present disclosure is a top emission device and the anode is formed on the substrate before the organic material layer and the cathode are formed, the anode may be formed not only of a transparent material but also of an opaque material having excellent light reflectivity.

[0608] When the organic electronic device according to the present disclosure is a bottom emission device and the anode is formed on the substrate before the organic material layer and the cathode are formed, the anode should be formed of a transparent material, or when formed of an opaque material should be provided as thin a film as possible to be transparent.

[0609] Hereinafter, the following examples will be presented by manufacturing a top emission tandem organic electronic device, but the embodiments of the present disclosure are not limited thereto. The tandem organic electronic device according to an embodiment of the present disclosure is manufactured such that a plurality of stacks are connected through one or more charge generation layers.

[0610] [Example 1 to Example 45] Tandem organic electronic device with two connected stacks

[0611] A series organic electronic device including two connected stacks is manufactured with the structure of anode / hole transport region / emission layer / electron transport region / electron injection layer / cathode. Specifically, a film of N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) doped with 10% HATCN is deposited on the anode formed on the glass substrate with a thickness of 10nm to form a hole injection layer. Afterwards, a hole transport layer I is formed by depositing a compound I (ie, a first hole transport material) represented by formula C or formula D and containing a compound group represented by formula A with a thickness of 15nm, and a hole transport layer II is formed by depositing a compound II (ie, a second hole transport material) represented by formula C or formula D and containing a compound group represented by formula A or formula B with a thickness of 5nm. DPVBi is used as the main body on the hole transport layer, and 5 wt% of BCzVBi is added as a dopant to deposit a 20nm emission layer. An Alq3 film is deposited with a thickness of 30nm as an electron transport layer. Subsequently, a charge generation layer is formed to connect the two stacks. That is, the N-type charge generation layer is formed by depositing Bphen doped with 2% Li, and the P-type charge generation layer is formed by depositing NPB doped with 10% HATCN. Afterwards, the hole transport region, the emission layer, and the electron transport region are sequentially deposited as described above to form a second stack. Thereafter, an electron injection layer is formed by depositing Liq with a thickness of 1.5nm, and then a cathode is formed by depositing Ag:Mg with a thickness of 150nm. Thus, a tandem organic electronic device is manufactured.

[0612] The electroluminescence (EL) characteristics of the organic electron emission devices according to the embodiments and comparative examples manufactured as above were measured using PR-650 available from Photo Research, Inc. by applying a forward bias DC voltage to the devices, and as a result of the measurement, the T95 life of the devices was tested using a life test apparatus available from Mcscience Inc. The following table illustrates the results of the manufacture and testing of the devices.

[0613] [Comparative Example 1 and Comparative Example 2]

[0614] A tandem organic electronic device was manufactured in the same manner as in Example, except that NPB and Compound 4-21 of the present disclosure were used as the first hole transport material, respectively, and the hole transport layer II was not used.

[0615] [Comparative Example 3]

[0616] A tandem organic electronic device was fabricated in the same manner as in Example, except that NPB was used as the first hole transport material and Compounds 6-30 of the present disclosure were used as the second hole transport material.

[0617] [Table 6]

[0618]

[0619]

[0620] [Example 46 to Example 90] A tandem organic electronic device having three connected stacks

[0621] A tandem organic electronic device was manufactured in the same manner as in Examples 1 to 45, except that the tandem organic electronic device was manufactured by connecting three stacks.

[0622] [Comparative Examples 4 and 5]

[0623] A tandem organic electronic device was fabricated in the same manner as in Example 46, except that NPB and Compound 4-21 of the present disclosure were used as the first hole transport material, respectively, and the hole transport layer II was not used.

[0624] [Comparative Example 6]

[0625] A tandem organic electronic device was fabricated in the same manner as Example 46, except that NPB was used as the first hole transport material and Compound 6-30 of the present disclosure was used as the second hole transport material.

[0626] [Table 7]

[0627]

[0628]

[0629] [Example 91 to Example 135] A tandem organic electronic device having four connected stacks

[0630] A tandem organic electronic device was manufactured in the same manner as in Examples 1 to 45, except that the tandem organic electronic device was manufactured by connecting four stacks.

[0631] [Comparative Examples 7 and 8]

[0632] A tandem organic electronic device was fabricated in the same manner as in Example 91, except that NPB and Compound 4-21 of the present disclosure were used as the first hole transport material, respectively, and the hole transport layer II was not used.

[0633] [Comparative Example 9]

[0634] A tandem organic electronic device was fabricated in the same manner as in Example 9, except that NPB was used as the first hole transport material and Compound 6-30 of the present disclosure was used as the second hole transport material.

[0635] [Table 8]

[0636]

[0637]

[0638] As can be seen from the results of Tables 6 to 8, it can be understood that when the hole transport region is formed using Compound I and Compound II of the present disclosure (Examples 1 to 135), the electrical characteristics of the device are improved compared to when NPB or Compound 4-21 of the present disclosure (i.e., a first compound represented by Formula C or Formula D and containing a compound group represented by Formula A) is used only for the first hole transport layer (Comparative Example 1, Comparative Example 2, Comparative Example 4, Comparative Example 5, Comparative Example 7, and Comparative Example 8) or when NPB is used for the first hole transport material and Compound 6-30 of the present disclosure represented by Formula C or Formula D is used for the second hole transport material (Comparative Example 3, Comparative Example 6, and Comparative Example 9).

[0639] It is described in detail that the device characteristics of Comparative Examples 2, 5 and 8 using Compounds 4-21 of the present disclosure are more improved than the device characteristics of Comparative Examples 1, 4 and 7 using NPB for the first hole transport material, and the device characteristics of Comparative Examples 3, 6 and 9 using NPB for the first hole transport material and Compounds 6-30 of the present disclosure for the second hole transport material are more improved than the device characteristics of Comparative Examples 1, 2, 4, 5, 7 and 8 using only the first hole transport material. In addition, it can be understood that in Examples 1 to 135 in which a first compound represented by Formula C or Formula D and containing a compound group represented by Formula A is used for the first hole transport material, and a second compound represented by Formula C or Formula D and containing a compound group represented by Formula A or Formula B is used for the second hole transport material, the device characteristics (such as driving voltage, efficiency and life) are more improved than the device characteristics of Comparative Examples 1 to 9.

[0640] It is believed that using the disclosed compound for the first hole transport material and the second hole transport material allows an appropriate number of holes in the emission layer to move efficiently so as to balance holes and electrons in the emission layer and prevent degradation in the interface of the emission layer, thereby improving efficiency and extending life.

[0641] At the same time, referring to Examples 1 to 45, 46 to 90, and 91 to 135 according to the present disclosure, it can be understood that the efficiency and lifespan in the device characteristics are improved as the number of connected stacks increases. Specifically, in the devices according to Examples 46 to 90 in which three stacks are connected, the driving voltage increases compared to Examples 1 to 45 in which two stacks are connected, but the efficiency and lifespan are improved. In addition, in Examples 91 to 135 in which four stacks are connected, the driving voltage increases compared to Examples 46 to 90, but the efficiency and lifespan are improved. It is believed that the efficiency and lifespan are improved proportionally with the increase in the number of stacks, which is due to the multi-photon emission structure in which excitons are generated to emit light energy in each stack in the stack.

[0642] In addition, referring to Examples 1 to 45, 46 to 90, and 91 to 135 according to the present disclosure, it can be seen that the value of the color coordinate (CIE x) gradually decreases as the number of connected stacks increases. It is believed that when the full width at half maximum (FWHM) of the emission wavelength decreases as the number of stacks increases, the color purity is improved.

[0643] The final product represented by Formula 1 according to the present disclosure may be synthesized by, but not limited to, the following Reaction Formula 18.

[0644] Hal is I, Br, or Cl.

[0645] [Reaction 18]

[0646]

[0647] I. Subsection of Reaction 18 1 Synthesis

[0648] Sub 1 of Reaction Formula 18 is synthesized through, but not limited to, the reaction path of the following Reaction Formula 19.

[0649] Hal 1 is I, Br, Cl, or -B(OH)2, and Hal is I, Br, or Cl.

[0650] p and q are 0 or 1 respectively.

[0651] When p and q are 0, Hal 1 is I, Br, or Cl, and no separate reaction is required.

[0652] When p and q are 1, Hal 1 It is -B(OH)2.

[0653] [Reaction 19]

[0654]

[0655] After adding (9,9-dimethyl-9H-fluorene-4-yl)boric acid (50.0g, 210.0mmol; 50g, 125.8mmol) to a round-bottom flask, 2-bromo-4'-chloro-1,1'-biphenyl (56.2g, 210.0mmol), Pd(PPh3)4 (14.6g, 12.6mmol), NaOH (25.2g, 630.0mmol) and water (525ml) were added, followed by stirring and refluxing. When the reaction was complete, extraction was performed with CH2Cl2 and water, and then the organic layer was dried and concentrated with MgSO4. The resulting organic substance was subjected to silica gel column chromatography and recrystallization to obtain a product in an amount of 65.0g (81.3%).

[0656] The compound belonging to Sub 1 of Reaction Formula 18 may be, but is not limited to, the following compounds, and Table 9 illustrates field desorption-mass spectrometry (FD-MS) values ​​of the compounds belonging to Sub 1.

[0657]

[0658]

[0659]

[0660]

[0661] [Table 9]

[0662]

[0663]

[0664] II.Sub Synthesis of 2

[0665] Sub 2 of Reaction Formula 18 is synthesized through, but not limited to, the reaction path of the following Reaction Formula 20.

[0666] [Reaction 20]

[0667]

[0668] 1.Sub Synthesis of 2-73

[0669]

[0670] Bromobenzene (37.1 g, 236.2 mmol) was added to a round-bottom flask, dissolved with toluene (2200 ml), and then aniline (20 g, 214.8 mmol), Pd2(dba)3 (9.83 g, 10.7 mmol), P(t-Bu)3 (4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) were added in sequence, followed by stirring at 100°C. When the reaction was complete, extraction was performed with ether and water, and then the organic layer was dried with MgSO4 and concentrated. The resulting organic material was subjected to silica gel column chromatography and recrystallization to obtain a product in an amount of 28 g (77%).

[0671] 2.Sub Synthesis of 2-111

[0672]

[0673] [1,1'-biphenyl]-4-amine (15 g, 88.64 mmol), 2-bromodibenzo[b,d]thiophene (23.32 g, 88.64 mmol), Pd2(dba)3 (2.43 g, 2.66 mmol), P(t-Bu)3 (17.93 g, 88.64 mmol), NaOt-Bu (17.04 g, 177.27 mmol) and toluene (886 mL) were added to a round-bottom flask, and the experiment was performed in the same manner as Sub 2-73 to obtain the product in an amount of 24.6 g (yield: 79%).

[0674] The compound belonging to Sub 2 of Reaction Formula 18 may be, but is not limited to, the following compounds, and Table 10 illustrates field desorption mass spectrometry (FD-MS) values ​​of the compound belonging to Sub 2.

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682] [Table 10]

[0683]

[0684]

[0685] III. Synthesis of the final product

[0686] 1. Synthesis Example of P1-4

[0687]

[0688] Sub 1-2 (10.0 g, 43.7 mmol), Sub 2-3 (15.8 g, 43.7 mmol), Pd2(dba)3 (1.2 g, 1.3 mmol), P(t-Bu)3 (0.5 g, 2.6 mmol), NaOt-Bu (8.4 g, 87.4 mmol) and toluene (219 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 17.4 g (yield: 72%).

[0689] 2. Synthesis Example of P2-13

[0690]

[0691] Sub 1-9 (10.0 g, 28.3 mmol), Sub 2-26 (9.5 g, 28.3 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P(t-Bu)3 (0.3 g, 1.7 mmol), NaOt-Bu (5.4 g, 56.7 mmol) and toluene (142 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 13.9 g (yield: 75%).

[0692] 3. Synthesis Example of P3-15

[0693]

[0694] Sub 1-31 (10.0 g, 23.4 mmol), Sub 2-82 (8.5 g, 23.4 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.4 mmol), NaOt-Bu (4.5 g, 46.8 mmol) and toluene (117 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 12.2 g (yield: 69%).

[0695] 4. Synthesis Example of P4-21

[0696]

[0697] Sub 1-9 (10.0 g, 28.3 mmol), Sub 2-3 (10.2 g, 28.3 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P(t-Bu)3 (0.3 g, 1.7 mmol), NaOt-Bu (5.4 g, 56.7 mmol) and toluene (142 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 13.7 g (yield: 72%).

[0698] 5. Synthesis Example of P5-38

[0699]

[0700] Sub 1-63 (10.0 g, 24.9 mmol), Sub 2-112 (9.4 g, 24.9 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (4.8 g, 49.9 mmol) and toluene (125 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 13.1 g (yield: 70%).

[0701] 6. Synthesis Example of P6-9

[0702]

[0703] Sub 1-113 (10.0 g, 35.9 mmol), Sub 2-106 (12.0 g, 35.9 mmol), Pd2(dba)3 (1.0 g, 1.1 mmol), P(t-Bu)3 (0.4 g, 2.2 mmol), NaOt-Bu (6.9 g, 71.7 mmol) and toluene (179 ml) were added to a round-bottom flask, and then the experiment was performed in the same manner as Sub 2-73 to obtain a product in an amount of 15.7 g (yield: 76%).

[0704] The FD-MS values ​​of the compounds prepared according to the above-mentioned synthesis examples of the present disclosure are shown in Table 11.

[0705] [Table 11]

[0706]

[0707]

[0708]

[0709]

[0710] Evaluation of organic electronic device manufacturing

[0711] When the organic electronic device according to the present disclosure is a top emission device and the anode is formed on the substrate before the organic material layer and the cathode are formed, the anode material can be implemented not only as a transparent material but also as an opaque material with excellent light reflectivity.

[0712] When the organic electronic device according to the present disclosure is a bottom emission device and the anode is formed on the substrate before the organic material layer and the cathode are formed, the anode material should be implemented as a transparent material, or when formed of an opaque material should be provided as a thin film as possible to be transparent.

[0713] Hereinafter, the following examples will be presented by manufacturing a top-emitting tandem organic electronic device, but the embodiments of the present disclosure are not limited thereto. The tandem organic electronic device according to the embodiments of the present disclosure is manufactured so that a plurality of stacks are connected by one or more charge generation layers. Although the same compound has been used for the hole transport layer of each of the three stacks in the tandem organic electronic device according to the embodiments of the present disclosure, the present disclosure is not limited thereto.

[0714] [Example 136] A tandem organic electronic device having three connected stacks

[0715] A tandem organic electronic device comprising three connected stacks is manufactured using a structure of first electrode (anode) / first hole transport region / first emission layer / first electron transport region / charge generation layer / second hole transport region / second emission layer / second electron transport region / charge generation layer / third hole transport region / third emission layer / third electron transport region / electron injection layer / second electrode (cathode).

[0716] Specifically, a hole injection layer was formed by vacuum depositing 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as TNATA) on an anode formed on a glass substrate with a thickness of 60 nm, a first hole transport layer of the first stack was formed by doping the compound P1-4 represented by Formula 1 of the present disclosure (hereinafter referred to as the first HTM) with HATCN as a doping material with a thickness of 11 nm (35% of the total thickness of 30 nm), and then P1-4 represented by Formula 1 of the present disclosure was formed on the first hole transport layer with a thickness of 19 nm. Subsequently, a first emission layer with a thickness of 20 nm was deposited on the first hole transport layer using DPVBi as a host and 5 wt% BCzVBi as a dopant. An electron transport layer was formed using Alq3 with a thickness of 30 nm. Thereafter, a charge generation layer was formed by doping Bphen with 2% Li for connection to the second stack. In addition, the compound P1-4 represented by Formula 1 of the present disclosure was doped with 10% HATCN as a doping material. 1 represented by the compound P1-4 (hereinafter referred to as the second HTM) to form the second stacked second hole transport layer with a thickness of 14nm (25% of the total thickness of 55nm), and then the P1-4 represented by Formula 1 of the present disclosure is formed on the second hole transport layer with a thickness of 41nm. After that, as described above, the second emission layer, the second electron transport region and the charge generation layer are sequentially formed. Finally, the third stacked third hole transport layer is formed with a thickness of 10nm (20% of the total thickness of 50nm) by doping the compound P1-4 represented by Formula 1 of the present disclosure (hereinafter referred to as the third HTM) with 10% HATCN as a doping material, and then the P1-4 represented by Formula 1 of the present disclosure is formed on the third hole transport layer with a thickness of 40nm. After the third emission layer and the third electron transport region are sequentially deposited as described above, a Liq electron injection layer with a thickness of 1.5nm is formed, and then a cathode is formed by depositing Ag:Mg with a thickness of 150nm. In this way, a tandem organic electronic device is manufactured.

[0717] The electroluminescence (EL) characteristics of the organic electron emission devices according to the embodiments and comparative examples manufactured in this manner were measured using PR-650 available from Photo Research, Inc. by applying a forward bias DC voltage to the devices, and as a result of the measurement, the T95 lifetime of the devices was tested using a lifetime test apparatus available from Mcscience Inc. The following table illustrates the results of the manufacture and testing of the devices.

[0718] [Example 137 to Example 170]

[0719] An organic electron emission device was manufactured in the same manner as in Example 136, except that the compounds shown in Table 12 below were used as hole transport materials of the first to third stacks.

[0720] [Table 12]

[0721]

[0722]

[0723] [Comparative Example 10 and Comparative Example 11]

[0724] An organic electron emission device was manufactured in the same method as in Example, except that only a single stack was formed, and the following Reference 1 and Reference 2 were used as hole transport materials.

[0725] [Reference 1 and Reference 2]

[0726]

[0727] As can be seen from the results of Table 12, it can be understood that when the compound represented by Formula 1 of the present disclosure is used as a hole transport material to manufacture a series organic light-emitting device (Example 136 to Example 170) each including three stacks, the electrical characteristics of the device are improved compared to when the reference 1 compound and the reference 2 compound are used as hole transport materials each including a single stack of organic light-emitting devices (Comparative Example 10 and Comparative Example 11). It is described in detail in Examples 136 to 170 and Comparative Examples 10 and 11 that the material of the hole transport layer is doped with a doping material having the same thickness, and different numbers of stacks are connected. As in Examples 136 to 170, it can be understood that as the number of connected stacks increases, the efficiency and lifespan in the device characteristics are significantly improved. It is believed that the efficiency and lifespan are improved proportionally with the increase in the number of stacks, which is due to the multi-photon emission structure, in which excitons are generated to emit light energy in each stack in the stack.

[0728] It can also be seen that the value of the color coordinate (CIE x) gradually decreases due to the device structure including three stacks as in the embodiment of the present disclosure. It is believed that when the full width at half maximum (FWHM) of the emission wavelength decreases as the number of stacks increases, color purity is improved.

[0729] At the same time, it can be seen that when the compound represented by Formula 1 of the present disclosure is used as the first hole transport layer material, the device characteristics are more improved than when the reference 1 material or the reference 2 material containing N is used as the first hole transport layer. When the compound of the present disclosure is used as a hole transport layer material, an appropriate number of holes can effectively move in the emission layer to balance the holes and electrons in the emission layer and prevent degradation in the interface of the emission layer, thereby improving efficiency and extending life.

[0730] [Example 171 and Example 174] A tandem organic electronic device having three connected stacks

[0731] A tandem organic light-emitting device was manufactured in the same manner as in Example 136, except that compounds P1-17 and P3-8 were used as hole transport materials for the first to third stacks as shown in Table 13 below, and a portion corresponding to 15% of the thickness of the hole transport layer was doped with HATCN, and each hole transport layer was 50 nm thick.

[0732] [Example 172 and Example 175]

[0733] A tandem organic light-emitting device was manufactured in the same manner as in Example 136, except that compounds P1-17 and P3-8 were used as hole transport materials for the first to third stacks as shown in Table 13 below, and a portion corresponding to 20% of the thickness of the hole transport layer was doped with HATCN, and each hole transport layer was 50 nm thick.

[0734] [Example 173 and Example 176]

[0735] A tandem organic light-emitting device was manufactured in the same manner as in Example 136, except that compounds P1-17 and P3-8 were used as hole transport materials for the first to third stacks as shown in Table 13 below, and a portion corresponding to 25% of the thickness of the hole transport layer was doped with HATCN, and each hole transport layer was 50 nm thick.

[0736] [Comparative Example 12 and Comparative Example 14]

[0737] A tandem organic light-emitting device was manufactured in the same manner as in Example 136, except that compounds P1-17 and P3-8 were used as hole transport materials for the first to third stacks as shown in Table 13 below, and a portion corresponding to 10% of the thickness of the hole transport layer was doped with HATCN, and each hole transport layer was 50 nm thick.

[0738] [Comparative Example 13 and Comparative Example 15]

[0739] A tandem organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds P1-17 and P3-8 were used as hole transport materials for the first to third stacks as shown in Table 13 below, and a portion corresponding to 55% of the thickness of the hole transport layer was doped with HATCN, and each hole transport layer was 50 nm thick.

[0740] [Table 13]

[0741]

[0742] Notes)

[0743] Thickness ratio1) : Thickness ratio (% of hole transport layer thickness)

[0744] As shown in Table 13, according to the present disclosure, a tandem device is manufactured and measured by changing the ratio of the portion of the hole transport layer doped with a doping material relative to the thickness of the hole transport layer of each stack in the first to third stacks. In the illustrative description of the compound, P1-17 and P3-8 are used as examples. As can be seen from the results of Table 13, it can be understood that when the hole transport layer is doped with a doping material so that the thickness of the hole transport layer doped with the doping material is less than 15% of the total thickness of the hole transport layer or greater than 50% of the total thickness of the hole transport layer, compared with the results of Examples 171 to 176 (wherein the hole transport layer is doped with a doping material at a ratio of 15%, 20%, and 25%), the results of the driving voltage, efficiency, and life of the device gradually decrease.

[0745] The result depends on the thickness of the portion of the hole transport layer doped with the doping material, that is, proportional to the weight ratio of the doping material added to the hole transport layer. When the portion of the hole transport layer doped with the doping material is too thin, the generation of holes and charges is insufficient, and the holes are not properly injected into the emission layer. As a result, the device characteristics may be degraded, which is problematic. In contrast, when the thickness of the portion of the hole transport layer doped with the doping material is too thick, problems may arise regarding the occurrence of short circuits or an increase in the total cost consumed by device manufacturing.

[0746] The above description is intended only to illustrate the present disclosure, and a person skilled in the art to which the present disclosure belongs may make various modifications without departing from the basic features of the present disclosure. The aforementioned embodiments disclosed herein should be interpreted as an illustration of the principles and scope of the present disclosure, rather than a limitation. It should be understood that the scope of the present disclosure will be limited by the appended claims, and all their equivalents fall within the scope of the present disclosure.

[0747] [Description of Reference Numbers in the Drawings]

[0748] 110: First electrode

[0749] 120: Second electrode

[0750] 130: Organic material layer

[0751] 141: First stack

[0752] 142: Second stack

[0753] 143: Third stack

[0754] 144: Fourth Stack

[0755] 150: Charge generation layer

[0756] 160: Capping layer

[0757] CROSS-REFERENCE TO RELATED APPLICATIONS

[0758] This application claims the benefit of priority under 35 U.S.C. §119(a) to Korean Patent Application No. 10-2019-0094551, filed on August 2, 2019, Korean Patent Application No. 10-2020-0047638, filed on April 20, 2020, and Korean Patent Application No. 10-2020-0082278, filed on July 3, 2020, respectively, which are hereby incorporated by reference for all purposes as if fully set forth herein. In addition, when this application claims priority on the same basis in countries other than the United States, its entirety is hereby incorporated by reference.

Claims

1. An organic electronic device, comprising: a first electrode; a second electrode; and an organic material layer, the organic material layer being located between the first electrode and the second electrode and comprising a first stack, a second stack and a third stack, wherein the first stack comprises a first hole transport region, a first emission layer and a first electron transport region, The first hole transport region includes a first hole transport layer and a first auxiliary emission layer. The first hole transport layer or the first auxiliary emission layer includes a first compound represented by any one of the following Formula 2, Formula 4, and Formula 5, The thickness of the first hole transport layer ranges from to and 10% to 50% of the thickness of the first hole transport layer is doped with a first doping material, [Formula 2] [Formula 4] [Formula 5] in Ar 1 and Ar 2 Each of which is selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, Ar 3 and Ar 4 Each of which is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, L 1 To L 6 Each of the following is independently selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, Each of Ring A and Ring B is independently C6-C 10 Aryl groups, R 1 and R 2 Each of the following is independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy groups, a is an integer from 0 to 7, and b is an integer from 0 to 8, d is an integer from 0 to 4, and e is an integer from 0 to 5, i)R 4 and R 6 Each of the following is independently selected from the group consisting of: deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 aryloxy group, and ii) multiple R 4 and multiple R 6 are respectively bonded to each other to form a ring, R 5 Selected from the group consisting of: hydrogen; deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C6-C 30 Aromatic rings and C3-C 30 Aliphatic ring fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 Aryloxy groups, Each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the arylene group and the fluorenyl group is further substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 a cycloalkyl group, and Each of the further substituted substituents can be further substituted by one or more substituents selected from the group consisting of: deuterium; a halogen group; a C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 A cycloalkyl group, and the substituents are bonded to each other to form a ring. 2 . The device according to claim 1 , wherein each of the first hole transport layer and the first auxiliary emission layer of the first stack includes the first compound represented by any one of Formula 2, Formula 4, and Formula 5. 3 .

3. The device of claim 1, wherein the first compound comprises one or more of the following compounds:

4. The device according to claim 1, wherein the first doping material is represented by the following formula E: [Formula E] in, In formula E, R p1 To R p6 Each of the following is independently selected from the group consisting of: hydrogen; a halogen group; a nitrile group; a nitro group; -SO2R; -SOR; -SO2NR2; -SO3R; a trifluoromethyl group; -COOR; -CONHR; -CONRR'; C1-C 30 Alkoxy group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 30 Heterocyclic group; Fluorenyl group; C6-C 30 Aryl group; C6-C 30 Aromatic rings and C3-C 30 aliphatic ring fused ring group; or -NRR', R and R' are each selected from the group consisting of: C1-C 30 Alkyl group; Fluorenyl group; C6-C 30 Aryl group; C6-C 30 Aromatic rings and C3-C 30 aliphatic ring fused ring group; or a C2-C 30 A heterocyclic group, and In Formula E, each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, and the alkoxy group is substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; or C3-C 20 Cycloalkyl groups.

5. The device according to claim 1, wherein the first hole transport layer comprises a first doping material doped layer doped with the first doping material and a first doping material undoped layer not doped with the first doping material, and The first doping material doping layer includes the first compound and 5 to 15 parts by weight of the first doping material relative to 100 parts by weight of the first compound.

6. The device of claim 1, wherein the second stack comprises a second hole transport region, a second emissive layer, and a second electron transport region, The second hole transport region includes a second hole transport layer and a second auxiliary emission layer, The second hole transport layer or the second auxiliary emission layer includes a second compound represented by any one of Formula 2, Formula 4, and Formula 5, The thickness of the second hole transport layer ranges from to 10% to 50% of the thickness of the second hole transport layer is doped with a second doping material, The third stack includes a third hole transport region, a third emission layer and a third electron transport region, The third hole transport region includes a third hole transport layer and a third auxiliary emission layer. The third hole transport layer or the third auxiliary emission layer includes a third compound represented by any one of Formula 2, Formula 4, and Formula 5, The thickness of the third hole transport layer ranges from to and 10% to 50% of the thickness of the third hole transport layer is doped with a third doping material. 7 . The device according to claim 6 , wherein the first compound, the second compound, and the third compound are the same compound.

8. The device according to claim 6, wherein the first hole transport layer or the first auxiliary emission layer comprises at least one of the first compound or the fourth compound, The fourth compound includes a compound group represented by the following formula A or formula B, and is represented by at least one of the following formula C or formula D, The thickness of the second hole transport layer ranges from to 10% to 50% of the thickness of the second hole transport layer is doped with a second doping material, [Formula A, Formula B, Formula C, and Formula D] in, In formula A, 1) each of a and b is independently an integer from 0 to 4, 2) X is O, S, CR'R", or N-L1-Ar1, 3) R1 and R2 are respectively and independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 an aryloxy group, and a plurality of R1s and a plurality of R2s are respectively bonded to form a ring, 4) R' and R" are each independently selected from the group consisting of: hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 an aliphatic ring fused ring group, wherein R' and R" are bonded to each other to form a ring, 5) L1 is selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 aliphatic ring fused ring group, and 6) Ar1 is selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, In formula B, 1) l is an integer from 0 to 5, m is an integer from 0 to 4, and each of y and z is an integer from 0 to 4, wherein y+z is not 0, 2) R a and R b are respectively and independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 aryloxy group, and multiple R a and multiple R b are bonded to form a ring, In formula C, 1) n is 1 or 2, 2) Ar2 is a compound group represented by formula A or a compound group represented by formula B, 3) Each of Ar3 and Ar4 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, 4) Each of L2 to L4 is independently selected from the group consisting of: a single bond; C6-C 60 an arylene group; a fluorenyl group; or a C2-C 60 A heterocyclic group, and In formula D, 1) o is an integer from 1 to 4, 2) Each of Ar5 to Ar8 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, 3) Each of L5 to L9 is independently selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 An aliphatic ring condensed ring group, wherein L9 is a compound group represented by formula A or a compound group represented by formula B, and In formulas A to D, Each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the arylene group and the fluorenylene group is further substituted with one or more substituents selected from the group consisting of: deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Aralkyl group; or C8-C 20 an aralkenyl group in which a further substituted substituent is bonded to form a ring, and Each of the further substituted substituents is further substituted by one or more substituents selected from the group consisting of: deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Aralkyl group; or C8-C 20 An aralkenyl group wherein the substituents are bonded to form a ring.

9. The device according to claim 6, wherein the first hole transport layer comprises a first doping material doped layer doped with the first doping material and a first doping material undoped layer not doped with the first doping material, The first doping material doping layer includes the first compound and 5 to 15 parts by weight of the first doping material relative to 100 parts by weight of the first compound, The second hole transport layer includes a second doping material doped layer doped with the second doping material and a second doping material undoped layer not doped with the second doping material, The second doping material doping layer includes the second compound and 5 to 15 parts by weight of the second doping material relative to 100 parts by weight of the second compound, The third hole transport layer includes a third doping material doped layer doped with a third doping material and a third doping material undoped layer not doped with the third doping material, and The third doping material doping layer includes the third compound and 5 to 15 parts by weight of the third doping material relative to 100 parts by weight of the third compound.

10. The device according to claim 8, wherein the first hole transport layer comprises a first doping material doped layer doped with the first doping material and a first doping material undoped layer not doped with the first doping material, and The first doping material doping layer includes at least one of the first compound or the fourth compound, and includes 5 to 15 parts by weight of the first doping material relative to 100 parts by weight of the total amount of the first compound and the fourth compound.

11. The device according to claim 6, wherein the organic material layer further comprises a fourth stack, wherein the fourth stack comprises a fourth hole transport region, a fourth emission layer and a fourth electron transport region, The fourth hole transport region includes a fourth hole transport layer and a fourth auxiliary emission layer, The fourth hole transport layer or the fourth auxiliary emission layer comprises at least one of the fifth compound or the sixth compound, The fifth compound is represented by any one of Formula 2, Formula 4 and Formula 5, The sixth compound includes a compound group represented by the following formula A or formula B, and is represented by the following formula C or formula D, The thickness of the fourth hole transport layer ranges from to 10% to 50% of the thickness of the fourth hole transport layer is doped with a fourth doping material, [Formula A, Formula B, Formula C, and Formula D] in, In formula A, 1) each of a and b is independently an integer from 0 to 4, 2) X is O, S, CR'R", or N-L1-Ar1, 3) R1 and R2 are respectively and independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 an aryloxy group, and a plurality of R1s and a plurality of R2s are respectively bonded to form a ring, 4) R' and R" are each independently selected from the group consisting of: hydrogen; deuterium; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 an aliphatic ring fused ring group, wherein R' and R" are bonded to each other to form a ring, 5) L1 is selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 aliphatic ring fused ring group, and 6) Ar1 is selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, In formula B, 1) l is an integer from 0 to 5, m is an integer from 0 to 4, and each of y and z is an integer from 0 to 4, wherein y+z is not 0, 2) R a and R b are respectively and independently selected from the group consisting of: deuterium; tritium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C6-C 60 Aromatic rings and C3-C 60 Aliphatic ring fused ring group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; or C6-C 30 aryloxy group, and multiple R a and multiple R b are bonded to form a ring, In formula C, 1) n is 1 or 2, 2) Ar2 is a compound group represented by formula A or a compound group represented by formula B, 3) Each of Ar3 and Ar4 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, 4) Each of L2 to L4 is independently selected from the group consisting of: a single bond; C6-C 60 an arylene group; a fluorenyl group; or a C2-C 60 A heterocyclic group, and In formula D, 1) o is an integer from 1 to 4, 2) Each of Ar5 to Ar8 is independently selected from the group consisting of: C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 A fused ring group of an aliphatic ring, 3) Each of L5 to L9 is independently selected from the group consisting of: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C 60 Heterocyclic group; or C6-C 60 Aromatic rings and C3-C 60 An aliphatic ring condensed ring group, wherein L9 is a compound group represented by formula A or a compound group represented by formula B, and In formulas A to D, Each of the aryl group, the fluorenyl group, the heterocyclic group, the condensed ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the arylene group and the fluorenylene group is further substituted with one or more substituents selected from the group consisting of: deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Aralkyl group; or C8-C 20 an aralkenyl group, wherein the further substituted substituents are bonded to form a ring, and Each of the further substituted substituents is further substituted with one or more substituents selected from the group consisting of: deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 25 Aryl group; C6-C substituted by deuterium 25 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Aralkyl group; or C8-C 20 An aralkenyl group wherein the substituents are bonded to form a ring. 12 . The device of claim 6 , wherein at least one of the first emission layer, the second emission layer, or the third emission layer is a blue light emitting layer. 13 . The device of claim 6 , wherein each of the first emission layer, the second emission layer, and the third emission layer is a blue light emitting layer.

14. The device of claim 6, wherein one or both of the first emission layer, the second emission layer, and the third emission layer are blue light emission layers, and one or both of the first emission layer, the second emission layer, and the third emission layer are green light emission layers.

15. The device according to claim 6, wherein two emission layers among the first emission layer, the second emission layer, and the third emission layer are blue light emission layers, and the remaining one emission layer among the first emission layer, the second emission layer, and the third emission layer is a green light emission layer.

16. The device of claim 15, wherein the green light emitting layer is located between the two blue light emitting layers. 17 . The device of claim 6 , wherein at least one of the first emission layer, the second emission layer, or the third emission layer is a multi-emission layer that emits green light and blue light. 18 . The device according to claim 11 , wherein two light emitting layers among the first to fourth light emitting layers are blue light emitting layers, and the remaining one light emitting layer different from the blue light emitting layer is a green light emitting layer. The device according to claim 11 , wherein the fourth hole transport layer comprises the fifth compound.

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