Compound, light-emitting device including same, electronic device including light-emitting device, and electronic equipment including electronic device

By using a specific compound in the interlayer of the light emitting device, in which three amine groups are substituted on the phenyl group and fluorenyl group is at the 4-position position of one amine group, the problem of insufficient luminescence efficiency and lifetime in the prior art is solved, and higher luminescence efficiency and longer lifetime are achieved.

CN119874540APending Publication Date: 2025-04-25SAMSUNG DISPLAY CO LTD
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Patent Information

Application Number
CN202411474425.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2023-10-23
Filing Date
2024-10-22
Publication Date
2025-04-25

AI Technical Summary

Technical Problem

The existing light emitting devices still have shortcomings in terms of luminescence efficiency and lifetime, especially when using phenylenediamine structures and aromatic diamine derivatives, it is difficult to achieve higher luminescence efficiency and long lifetime.

Method used

A compound represented by Formula 1 is provided for forming an interlayer of a light emitting device in which three amine groups are substituted on phenyl groups and fluorenyl groups are in a 4-position position in one amine group to improve luminescence efficiency and lifetime.

Benefits of technology

By using this compound, the luminescence efficiency and lifetime of the luminescence device have been significantly improved, and the problem of insufficient luminescence efficiency and lifetime in the prior art has been solved.

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Abstract

The present application provides a compound represented by Formula 1, a light-emitting device including the compound represented by Formula 1, an electronic device including the light-emitting device, and an electronic device including the electronic device. Formula 1 # imgabs0 #
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Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0142339 filed in the Korean Intellectual Property Office on October 23, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of the present disclosure are directed to a compound, a light-emitting device including the compound, an electronic device including the light-emitting device, and electronic equipment including the electronic device. Background Art

[0004] The light emitting device is a self-emissive device having a relatively wide viewing angle, a relatively high contrast ratio, a relatively short response time, and excellent or appropriate characteristics in terms of brightness, driving voltage and / or response speed compared to comparable devices in the prior art.

[0005] In the light-emitting device, a first electrode is provided on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to generate light. Summary of the invention

[0006] One or more aspects of the embodiments of the present disclosure relate to a compound, a light-emitting device including the compound, an electronic device including the light-emitting device, and electronic equipment including the electronic device.

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

[0008] According to one or more embodiments of the present disclosure,

[0009] A compound represented by Formula 1 is provided.

[0010] Formula 1

[0011]

[0012] In formula 1,

[0013] R 1 , R 2 , R 4 and Ar 1 To Ar 5 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a The substituted monovalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group,

[0014] R 3 may be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl is either unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl,

[0015] Optionally, R 1 and R 2 can be connected together to form a ring,

[0016] L can be a single bond, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a The substituted divalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group,

[0017] m may be an integer selected from 0 to 3, wherein when m is 2 or more, each L may be the same as or different from each other, and n may be an integer selected from 0 to 3, wherein when n is 2 or more, each R 4 can be the same or different from each other, R 10a Can be:

[0018] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0019] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0020] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0021] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0022] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1-C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0023] According to one or more embodiments of the present disclosure,

[0024] A light-emitting device includes the above compound.

[0025] According to one or more embodiments of the present disclosure,

[0026] The electronic device includes a light emitting device.

[0027] According to one or more embodiments of the present disclosure,

[0028] Electronic equipment includes electronic equipment. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and together with the description are used to explain the principles of the present disclosure. The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:

[0030] Figure 1 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;

[0031] Figure 2 is a cross-sectional view of an electronic device according to one or more embodiments of the present disclosure;

[0032] Figure 3 is a cross-sectional view of an electronic device according to one or more embodiments of the present disclosure;

[0033] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to one or more embodiments of the present disclosure;

[0034] Figure 5 is a schematic diagram of the exterior of a vehicle as an electronic device including a light emitting device according to one or more embodiments of the present disclosure; and

[0035] Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of the interior of a vehicle according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION

[0036] The embodiments in the accompanying drawings will now be explained in more detail with reference to their examples, wherein the same reference numerals refer to the same elements throughout the present disclosure, and for the sake of brevity, their repeated description may not be provided. In this regard, the embodiments of the present disclosure may have different forms and should not be interpreted as being limited to the descriptions stated herein. Accordingly, by referring to the accompanying drawings, the embodiments of the present disclosure are only described to explain the various aspects of the present disclosure. As used herein, the term "and / or" or "or" may include any and all combinations of one or more related enumerated items. Throughout the present disclosure, expressions such as "at least one of ...", "one of ..." and "selected from ...", when before / after the list of elements, modify the entire list of elements without modifying the individual elements of the list. For example, "at least one of a, b and c", "selected from at least one of a, b and c", "selected from at least one of a to c", etc., may indicate only a, only b, only c, both a and b (e.g., a and b at the same time), both a and c (e.g., a and c at the same time), both b and c (e.g., b and c at the same time), all a, b and c, or variations thereof. As used herein, “ / ” may be interpreted as “and” or as “or” depending on the specific circumstances.

[0037] In the prior art, a phenylenediamine structure is used as a hole injection layer material used in a light-emitting device, and aromatic diamine derivatives, aromatic condensed ring diamine derivatives, etc. are used as hole transport layer materials. Aromatic amine compounds containing carbazole are used as hole transport layer materials as improved compounds among these compounds. In addition, aromatic amine compounds having carbazole substituted at the 3-position are used as hole injection layer materials in the art. Light-emitting devices using these compounds in a hole injection layer or a hole transport layer still do not have sufficient luminous efficiency, and therefore, still require and / or expect higher efficiency characteristics.

[0038] In addition, light-emitting devices using two or more hole transport layers having ionization potential values ​​set in a stepwise manner in order to efficiently inject holes from the anode into the emission layer have been studied, but the above-mentioned light-emitting devices have insufficient light emission efficiency and insufficient lifespan.

[0039] According to one or more aspects of the present disclosure, there is provided a compound represented by Formula 1:

[0040] Formula 1

[0041]

[0042] Among them, in formula 1,

[0043] R 1 , R 2 , R 4 and Ar 1 To Ar 5 can be each independently hydrogen, deuterium, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a The substituted monovalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group,

[0044] R 3 may be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl is either unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl,

[0045] Optionally, R 1 and R 2 can be connected together to form a ring,

[0046] L can be a single bond, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a The substituted divalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group,

[0047] m may be an integer selected from 0 to 3,

[0048] in,

[0049] When m is 0, -(L) m - can be a single key,

[0050] When m is 2 or more, each L may be the same as or different from each other,

[0051] n may be an integer selected from 0 to 3, wherein when n is 2 or greater, each R 4 can be the same or different from each other, R 10a Can be:

[0052] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0053] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0054] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0055] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0056] Q 11 To Q13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0057] In the compound represented by Formula 1 according to one or more embodiments, three amine groups are substituted on the phenyl group, and a fluorenyl group is substituted at one of the three amine groups. Here, according to one or more embodiments of the present disclosure, R 3 Substitution at the 4-position of the fluorenyl group of Formula 1 (see herein).

[0058]

[0059] According to some embodiments, a substituent may be present at another position of the fluorenyl group of Formula 1 (eg, 1-position, 2-position, or 3-position or R 4 Position), but in which R 3 In the embodiment present at the 4-position of the fluorenyl group, the luminous efficiency and life of the light-emitting device including the compound represented by Formula 1 may be improved. 3 may be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkyl is either unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl.

[0060] In one or more embodiments, Ar 1 To Ar 5 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl.

[0061] In one or more embodiments, Ar 1 To Ar 5 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, coronenyl or ovalenyl.

[0062] For example, in some embodiments, Ar 1 To Ar 5 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl or naphthyl.

[0063] In one or more embodiments, each R 4 may independently be hydrogen or deuterium.

[0064] In one or more embodiments, R 1 To R 3 may be each independently unsubstituted or substituted with at least one R 10a substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentalenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, corundum or ovalenyl.

[0065] In one or more embodiments, the compound represented by Formula 1 may be a compound represented by Formula 2:

[0066] Formula 2

[0067]

[0068] Among them, in formula 2,

[0069] R 1 To R 3 ,Ar 1 , L and m may be the same as defined in Formula 1, respectively.

[0070] In one or more embodiments, R 1 To R 3 may be each independently unsubstituted or substituted with at least one R 10a Substituted methyl, phenyl or naphthyl.

[0071] For example, in some embodiments, R 1 To R 3 Each may independently be a methyl group or a phenyl group.

[0072] In one or more embodiments, Ar 1 may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, and R 10a Can be unsubstituted or replaced by C 3 -C 60 Carbocyclic substituted C 3 -C 60 For example, in some embodiments, R 10a Can be: unsubstituted or replaced by C 3 -C 10 Cycloalkyl or C 6 -C 60 Aryl substituted C 6 -C 60 Aryl; either unsubstituted or substituted by C 3 -C 10 Cycloalkyl or C 6 -C 60 Aryl substituted C 3 -C 10 Cycloalkyl.

[0073] In one or more embodiments, the compound represented by Formula 1 may include (eg, selected from) one of the following compounds:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] A light emitting device according to one or more aspects of the present disclosure may include:

[0083] a first electrode;

[0084] a second electrode facing (eg, opposite and toward) the first electrode; and

[0085] an interlayer between the first electrode and the second electrode and including an emitting layer,

[0086] The interlayer may include a compound represented by Formula 1.

[0087] In one or more embodiments,

[0088] An electronic device may include a light emitting device.

[0089] In one or more embodiments, the electronic device may further include a thin film transistor,

[0090] The thin film transistor comprises a source electrode and a drain electrode, and

[0091] The first electrode of the light emitting device may be electrically connected to a source electrode or a drain electrode of the thin film transistor.

[0092] The term "interlayer" as used herein refers to a single layer and / or multiple layers between a first electrode and a second electrode of a light emitting device.

[0093] Figure 1 Description

[0094] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments of the present disclosure. The light emitting device 10 may include a first electrode 110 , an interlayer 130 , and a second electrode 150 .

[0095] In the following, reference Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described in more detail.

[0096] First electrode 110

[0097] exist Figure 1In one or more embodiments, a substrate may be additionally provided and arranged under the first electrode 110 and / or on the second electrode 150. A glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or appropriate heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0098] The first electrode 110 may be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.

[0099] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0100] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. In some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.

[0101] Mezzanine 130

[0102] The interlayer 130 is disposed above (eg, on) the first electrode 110. The interlayer 130 may include an emission layer.

[0103] In one or more embodiments, the interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .

[0104] In one or more embodiments, the interlayer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots), etc., in addition to one or more suitable organic materials.

[0105] In one or more embodiments, the interlayer 130 may include, i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emission units. When the interlayer 130 includes the emission units and the charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.

[0106] Hole transport region in interlayer 130

[0107] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.

[0108] The hole transport region may include a hole transport layer, a hole injection layer, an emission assisting layer, an electron blocking layer, or any combination thereof. For example, the hole transport region may include a hole transport layer, and a hole injection layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0109] In one or more embodiments, the hole transport region may have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, and the constituent layers of each structure are stacked in sequence in the order described starting from the first electrode 110.

[0110] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0111] Formula 201

[0112]

[0113] Formula 202

[0114]

[0115] Among them, in equation 201 and equation 202,

[0116] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1 -C 60 Heterocyclic group,

[0117] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0118] xa1 to xa4 may each independently be an integer selected from 0 to 5,

[0119] xa5 may be an integer selected from 1 to 10,

[0120] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0121] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (eg, carbazole groups) (eg, see compound HT16),

[0122] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 polycyclic groups, and

[0123] na1 may be an integer selected from 1 to 4.

[0124] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY217:

[0125]

[0126] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be respectively with respect to R 10a Same as described, CY 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.

[0127] In one or more embodiments, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.

[0128] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY203.

[0129] In one or more embodiments, Formula 201 may include at least one selected from the group represented by Formulas CY201 to CY203 and at least one selected from the group represented by Formulas CY204 to CY217.

[0130] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be a group represented by one selected from Formula CY201 to Formula CY203, xa2 may be 0, and R 202It may be a group represented by one selected from Formula CY204 to Formula CY207.

[0131] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any one of the groups represented by Formula CY201 to Formula CY203.

[0132] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any one of the groups represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.

[0133] In one or more embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) any one of the groups represented by Formula CY201 to Formula CY217. In the present disclosure, "not including one or any 'component'", "excluding one or any 'component'" and / or "not containing a 'component'" and the like means that the "component" is not added, selected or used as a component in the composition / formula / structure, but, in some embodiments, due to other impurities and / or external factors, the "component" may still be included in an appropriate amount.

[0134] In one or more embodiments, the hole transport region may include at least one selected from the group consisting of Compound HT1 to Compound HT46, 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB (NPD)), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPB), D), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0135]

[0136]

[0137]

[0138]

[0139] In one or more embodiments, the hole transport layer may include the compound represented by Formula 1.

[0140] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer may be about to about For example, about to about When the thickness of the hole transport region, the hole injection layer and the hole transport layer is within the above range, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0141] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The materials that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.

[0142] p-dopant

[0143] In one or more embodiments, in addition to one or more of these aforementioned materials, the hole transport region may further include a charge generation material for improved conductive properties. The charge generation material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer including (e.g., consisting of) the charge generation material).

[0144] The charge generating material may be, for example, a p-dopant.

[0145] For example, in one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be less than or equal to -3.5 eV.

[0146] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound containing the element EL1 and the element EL2, or any combination thereof.

[0147] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ).

[0148] Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and a compound represented by Formula 221.

[0149]

[0150] Formula 221

[0151]

[0152] In formula 221,

[0153] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and

[0154] Selected from R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0155] In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0156] Non-limiting examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc.); (e.g., tantalum (Tb), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

[0157] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te).

[0158] Non-limiting examples of non-metals may include oxygen (O) and / or halogens (eg, F, Cl, Br, I, etc.).

[0159] Non-limiting examples of compounds containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0160] Non-limiting examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO3 wait).

[0161] Non-limiting examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides.

[0162] Non-limiting examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI.

[0163] Non-limiting examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 .

[0164] Non-limiting examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 , TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0165] Non-limiting examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 wait).

[0166] Non-limiting examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 .

[0167] Non-limiting examples of metalloid halides may include antimony halides (e.g., SbCl 5 wait).

[0168] Non-limiting examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0169] Emission layer in interlayer 130

[0170] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer and the blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from the red light-emitting material, the green light-emitting material and the blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).

[0171] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0172] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0173] In one or more embodiments, the emissive layer may include quantum dots.

[0174] In one or more embodiments, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emission layer.

[0175] In one or more embodiments, the emission layer may include two hosts. In one or more embodiments, the emission layer may include a hole transport host and an electron transport host.

[0176] In one or more embodiments, the emission layer may include two dopants. In one or more embodiments, the emission layer may include a phosphorescent dopant and a fluorescent dopant.

[0177] In one or more embodiments, the fluorescent dopant may include a delayed fluorescent material.

[0178] The thickness of the emission layer may be about to about For example, about to about When the thickness of the emission layer is within the above range, excellent or appropriate light emitting characteristics may be obtained without significantly increasing the driving voltage.

[0179] main body

[0180] The hole transport host may be a compound with strong hole properties. The expression "compound with strong hole properties" refers to a compound that easily accepts and / or transports holes (e.g., has a relatively high hole mobility), and this property can be obtained by including a hole accepting part (also called a hole transporting part).

[0181] Such a compound including a hole accepting moiety may include, for example, a π-electron-rich heteroaromatic compound (eg, a carbazole derivative or an indole derivative) or an aromatic amine compound.

[0182] The electron transport host may be a compound with strong electronic properties. The expression "compound with strong electronic properties" refers to a compound that easily accepts and / or transports electrons (e.g., has a relatively high electron mobility), and this property can be obtained by including an electron accepting part (also called an electron transporting part).

[0183] Such a compound including an electron accepting moiety may include, for example, a π-electron-deficient heteroaromatic compound. For example, the electron accepting moiety may include a nitrogen-containing heteroaromatic compound (eg, a π-electron-deficient nitrogen-containing heteroaromatic compound).

[0184] The emission layer of the light-emitting device according to one or more embodiments may include a hole transport host and an electron transport host as a mixed host. For example, in some embodiments, the host may be a pre-mixed host of a hole transport host and an electron transport host.

[0185] When the compound includes only a hole transporting portion or only an electron transporting portion, it is clear whether the property of the compound has a hole transporting property or an electron transporting property.

[0186] In some embodiments, a compound may include (e.g., include) both a hole transport moiety and an electron transport moiety. In these embodiments, a simple comparison between the total amount of hole transport moieties and the total amount of electron transport moieties in the compound may be a criterion for predicting whether a compound is a hole transport compound or an electron transport compound, but may not be an absolute criterion. One reason why this simple comparison may not be an absolute criterion is that the ability of a hole transport moiety to attract and / or transport holes and the ability of an electron transport moiety to attract and / or transport electrons are not exactly the same.

[0187] Therefore, a relatively reliable means of determining whether a compound having a particular structure is a hole transport compound or an electron transport compound is to implement the compound directly in a device.

[0188] In one or more embodiments, the host may include a compound represented by Formula 301:

[0189] Formula 301

[0190] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,

[0191] Wherein, in Formula 301,

[0192] Ar 301 and L 301 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0193] xb11 can be 1, 2 or 3,

[0194] xb1 may be an integer selected from 0 to 5,

[0195] R301 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0196] xb21 may be an integer selected from 1 to 5, and

[0197] Q 301 To Q 303 Can be respectively with respect to Q 11 Same as described.

[0198] In some embodiments, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be connected to each other via a single bond.

[0199] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0200] Formula 301-1

[0201]

[0202] Formula 301-2

[0203]

[0204] Among them, in Formula 301-1 and Formula 301-2,

[0205] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0206] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0207] xb22 and xb23 can each independently be 0, 1 or 2,

[0208] L 301 , xb1 and R 301 may each be the same as described in the present disclosure,

[0209] L 302 To L 304 Can be independently compared with L 301 Same as described,

[0210] xb2 to xb4 may each independently be the same as described for xb1, and

[0211] R 302 To R 305 and R 311 To R 314 Can be respectively with respect to R 301 Same as described.

[0212] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In some embodiments, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0213] In one or more embodiments, the host may include at least one selected from Compound H1 to Compound H126, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9H-carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] Phosphorescent dopants

[0221] In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.

[0222] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0223] The phosphorescent dopant may be electrically neutral.

[0224] In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0225] Formula 401

[0226] M(L 401 ) xc1 (L 402 ) xc2

[0227] Formula 402

[0228]

[0229] Among them, in equation 401 and equation 402,

[0230] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0231] L 401 may be a ligand represented by Formula 402, and xc1 is 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,

[0232] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,

[0233] X 401 and X 402 may each independently be nitrogen or carbon,

[0234] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0235] T 401 It can be a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C=,

[0236] X 403 and X 404 can be independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0237] Q 411 To Q 414 can be independently compared with Q 11 Same as described,

[0238] R 401and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0239] Q 401 To Q 403 can be independently compared with Q 11 Same as described,

[0240] xc11 and xc12 may each independently be an integer selected from 0 to 10, and

[0241] * and *' in Formula 402 each indicate a binding site with M in Formula 401.

[0242] In one or more embodiments, in Formula 402, i) X 401 may be nitrogen and X 402 Can be carbon, or ii) X 401 and X 402 Each of may be nitrogen.

[0243] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 The two rings A 401 Optionally, T as a linking group 402 Connect together and / or two rings A 402 Optionally, T as a linking group 403Connected together (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be respectively with respect to T 401 Same as described.

[0244] L in Formula 401 402 Can be an organic ligand. In one or more embodiments, L 402 It may include halogen, diketone group (e.g., acetylacetonate group), carboxylic acid group (e.g., picolinate group), -C(=O), isonitrile group, -CN group, phosphorus-containing group (e.g., phosphine group, phosphite group, etc.) or any combination thereof.

[0245] In the ligand of the organometallic compound, adjacent substituents may optionally be bonded together to form a ring.

[0246] In one or more embodiments, the phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD40 or any combination thereof:

[0247]

[0248]

[0249]

[0250] Fluorescent dopants

[0251] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.

[0252] For example, in one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:

[0253] Formula 501

[0254]

[0255] Wherein, in Formula 501,

[0256] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0257] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0258] xd4 can be 1, 2, 3, 4, 5 or 6.

[0259] In one or more embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracenyl, 1,2-triphenylenyl, pyrenyl, etc.).

[0260] In some embodiments, xd4 in equation 501 may be 2.

[0261] In one or more embodiments, the fluorescent dopant may include: at least one selected from Compound FD1 to Compound FD37; 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi); or any combination thereof:

[0262]

[0263]

[0264]

[0265] Delayed fluorescence material

[0266] In one or more embodiments, the emission layer may include a delayed fluorescent material.

[0267] Herein, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0268] The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the types or kinds of other materials included in the emission layer.

[0269] In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be at least about 0 eV and not more than about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material is satisfied within the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus the light emitting device 10 may have improved luminous efficiency.

[0270] In one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C 3 -C 60a cyclic group, such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group and / or a π-electron-deficient nitrogen-containing C 1 -C 60 cyclic groups, etc.), and / or ii) includes C containing at least two cyclic groups fused to each other and sharing boron (B) 8 -C 60 Polycyclic materials.

[0271] Non-limiting examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:

[0272]

[0273]

[0274] Electron transport region in interlayer 130

[0275] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.

[0276] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0277] For example, in one or more embodiments, the electron transport region may have a structure including an electron transport layer / electron injection layer structure or a hole blocking layer / electron transport layer / electron injection layer structure, wherein in each structure, constituent layers are sequentially stacked in the order recited from the emission layer.

[0278] In one or more embodiments, the electron transport region (eg, a hole blocking layer or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.

[0279] In one or more embodiments, the electron transport region may include a compound represented by Formula 601:

[0280] Formula 601

[0281] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,

[0282] In formula 601,

[0283] Ar 601 and L 601 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,

[0284] xe11 can be 1, 2 or 3,

[0285] xe1 can be 0, 1, 2, 3, 4 or 5,

[0286] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0287] Q 601 To Q 603 can be independently compared with Q 11 Same as described,

[0288] xe21 can be 1, 2, 3, 4, or 5, and

[0289] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.

[0290] In one or more embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be linked together via a single bond.

[0291] In one or more embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.

[0292] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:

[0293] Formula 601-1

[0294]

[0295] Among them, in formula 601-1,

[0296] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and selected from X 614 To X 616 At least one of may be N,

[0297] L 611 To L 613 Can be independently compared with L 601 Same as described,

[0298] xe611 to xe613 can each independently be the same as described for xe1,

[0299] R 611 To R 613 Can be independently compared with R 601 Same as described, and

[0300] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.

[0301] In some embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0302] In one or more embodiments, the electron transport region may include: at least one selected from the group consisting of Compound ET1 to Compound ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinoline)aluminum (Alq 3 ); bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq); 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ); 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ); or any combination thereof:

[0303]

[0304]

[0305]

[0306] The thickness of the electron transport region may be about to about For example, about to about When the electron transport region includes a hole blocking layer, an electron transport layer, or any combination thereof, the thickness of the hole blocking layer may be about to about For example, about to about The thickness of the electron transport layer may be about to about For example, about to about When the thickness of the hole blocking layer and / or the electron transport layer is within the range as described above, satisfactory electron transport characteristics may be obtained without significantly increasing the driving voltage.

[0307] In one or more embodiments, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the one or more materials described above.

[0308] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0309] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:

[0310]

[0311] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

[0312] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.

[0313] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0314] The alkali metal may include Li, Na, K, Rb, Cs or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd or any combination thereof.

[0315] The alkali metal-containing compound, the alkaline earth metal-containing compound and the rare earth metal-containing compound may include oxides, halides (eg, fluorides, chlorides, bromides, iodides, etc.) or tellurides of alkali metals, alkaline earth metals and rare earth metals, respectively, or any combination thereof.

[0316] Alkali metal compounds may include: alkali metal oxides, such as Li 2 O、Cs 2 O or K2 O; an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI; or any combination thereof. The alkaline earth metal compound may include an alkaline earth metal oxide, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The rare earth metal compound may include YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 or any combination thereof. In one or more embodiments, the rare earth metal compound may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 , Ce 2 Te 3 , Pr 2 Te 3 , Nd 2 Te 3 , Pm 2 Te 3 , Sm 2 Te 3 , Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 , Dy 2 Te 3 , Ho 2 Te 3 , Er 2 Te 3 , Tm 2 Te 3 , Yb 2 Te 3 and Lu 2 Te 3 .

[0317] The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex may include i) one of the metal ions of the alkali metal, one of the metal ions of the alkaline earth metal and one of the metal ions of the rare earth metal, and ii) a ligand bonded to the metal ion (e.g., the respective metal ion), for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0318] In one or more embodiments, the electron injection layer may include (e.g., be composed of): an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In some embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).

[0319] In one or more embodiments, the electron injection layer may include (e.g., consisting of): i) an alkali metal compound (e.g., an alkali metal halide), or ii) a) an alkali metal compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In some embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.

[0320] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.

[0321] The thickness of the electron injection layer may be about to about Or, for example, about to about When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0322] The second electrode 150

[0323] The second electrode 150 may be disposed on the interlayer 130. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.

[0324] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.

[0325] The second electrode 150 may have a single-layer structure, or a multi-layer structure including a plurality of layers.

[0326] Capping layer

[0327] The first capping layer may be disposed on the outside (e.g., on) the first electrode 110, and / or the second capping layer may be disposed on the outside (e.g., on) the second electrode 150. In one or more embodiments, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the order recited, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the order recited, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the order recited.

[0328] In some embodiments, light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first capping layer. In some embodiments, light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second capping layer.

[0329] The first capping layer and the second capping layer can increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be increased.

[0330] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).

[0331] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0332] At least one of the first capping layer or the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include an amine-containing compound.

[0333] In one or more embodiments, at least one of the first capping layer and the second capping layer may (eg, the first capping layer and the second capping layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0334] In one or more embodiments, at least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include: at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB or any combination thereof:

[0335]

[0336] Electronic devices

[0337] The light emitting device may be included in one or more suitable electronic devices. For example, in one or more embodiments, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.

[0338] In one or more embodiments, in addition to the light emitting device, the electronic device (e.g., light emitting device) may further include: i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction of travel of the light emitted from the light emitting device. For example, in some embodiments, the light emitted from the light emitting device may be blue light or white light (e.g., combined white light). A detailed description of the light emitting device is provided above.

[0339] The electronic device may include a first substrate, the first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.

[0340] A pixel defining film may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.

[0341] The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the plurality of color conversion regions.

[0342] The plurality of color filter regions (or the plurality of color conversion regions) may include a first region configured to emit a first color light, a second region configured to emit a second color light, and / or a third region configured to emit a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. In one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In one or more embodiments, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In some embodiments, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) quantum dots. In one or more embodiments, the first region, the second region, and / or the third region may each further include a scatterer.

[0343] In one or more embodiments, the light emitting device may emit a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. In some embodiments, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In some embodiments, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

[0344] In one or more embodiments, in addition to the light emitting device described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light emitting device.

[0345] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.

[0346] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.

[0347] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be extracted to the outside, and synchronously (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0348] In one or more embodiments, in addition to the color filter and / or color conversion layer, various functional layers may be additionally arranged on the sealing portion according to the purpose of the electronic device. Non-limiting examples of the functional layer may include a touch screen layer and / or a polarizing layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.

[0349] The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (eg, fingertip, pupil, etc.) In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.

[0350] The electronic device can be applied to one or more displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish finders, one or more appropriate measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), and / or projectors, etc.

[0351] Electronic equipment

[0352] The light emitting device may be included in one or more suitable electronic devices.

[0353] In one or more embodiments, the electronic equipment including the light emitting device may be at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, and a sign.

[0354] Since the light emitting device has excellent or appropriate effects in terms of light emitting efficiency and long life, electronic equipment including the light emitting device may have desirable characteristics of high brightness, high resolution, and low power consumption.

[0355] Figure 2 and Figure 3 Description

[0356] Figure 2 is a cross-sectional view of an electronic device 180 according to one or more embodiments of the present disclosure.

[0357] Figure 2 The electronic device 180 may include a substrate 100, a thin film transistor (TFT), a light emitting device, and a packaging portion 300 that seals the light emitting device.

[0358] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100, and may provide a flat surface on the substrate 100.

[0359] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0360] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0361] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220 , and the gate electrode 240 may be on the gate insulating film 230 .

[0362] The interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate each other.

[0363] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.

[0364] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

[0365] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.

[0366] A pixel defining film 290 including an insulating material may be on the first electrode 110. The pixel defining film 290 may expose a certain area of ​​the first electrode 110, and the interlayer 130 may be formed in the exposed area of ​​the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290 and be arranged in the form of a common layer.

[0367] The second electrode 150 may be on the interlayer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0368] The encapsulation part 300 may be on the capping layer 170. The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyaromatic ester, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0369] Figure 3 is a cross-sectional view of an electronic device 190 according to one or more embodiments.

[0370] Figure 3 Electronic equipment 190 and Figure 2 The electronic device 180 is substantially the same as the electronic device 180, except that the light shielding pattern 500 and the functional area 400 are additionally arranged on the packaging portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, Figure 3 The light-emitting device included in the electronic device 190 may be a series-connected light-emitting device.

[0371] Figure 4 Description

[0372] Figure 4 Schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. The electronic device 1 can be a device for displaying moving images or still images, a portable electronic device (such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation or ultra mobile PC (UMPC)), and one or more suitable products (such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device). The electronic device 1 can be such a product or a part thereof as above. In some embodiments, the electronic device 1 can be a wearable device, such as a smart watch, a watch phone, a display of the type or kind of glasses or a head-mounted display (HMD), or a part of a wearable device. However, the embodiments of the present disclosure are not limited thereto. In one or more embodiments, the electronic device 1 may be a dashboard of a vehicle, a center information display (CID) arranged on a center console or dashboard of a vehicle, an interior rearview mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display arranged on a backrest of a front seat of a vehicle, a head-up display (HUD) mounted in front of the vehicle or projected on a front windshield, and / or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 4 An embodiment is explained in which the electronic device 1 is a smart phone.

[0373] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic equipment 1 may realize an image through a plurality of pixel arrays two-dimensionally arranged in the display area DA.

[0374] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to a display element arranged in the display area DA may be arranged. In the non-display area NDA, a pad may be arranged, which may be electrically connected to an electronic element or a printed circuit board.

[0375] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction (eg, width) may be different from each other. Figure 4 , the length in the x-axis direction may be smaller than the length (e.g., width) in the y-axis direction. In some embodiments, the length in the x-axis direction may be substantially the same as the length (e.g., width) in the y-axis direction. In some embodiments, the length in the x-axis direction may be greater than the length (e.g., width) in the y-axis direction.

[0376] Figure 5 and FIG. 6A to FIG. 6CDescription

[0377] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.

[0378] See also Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving an object to be transported (such as a person, object, or animal) from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or river, and / or an airplane flying in the air using the action of air.

[0379] In one or more embodiments, the vehicle 1000 may travel on a road or track. The vehicle 1000 may move in a certain direction according to the rotation of at least one wheel thereof. In some embodiments, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, or a train traveling on a track.

[0380] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical equipment required for driving is installed as other parts outside the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front wheels and rear wheels and / or left wheels and right wheels, etc.

[0381] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , an instrument cluster 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0382] The side window glass 1100 and the front window glass 1200 may be divided by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0383] The side window glass 1100 may be mounted on the side of the vehicle 1000. In some embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the instrument cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.

[0384] In one or more embodiments, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). In some embodiments, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In other words, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. In some embodiments, the imaginary or virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.

[0385] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.

[0386] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In some embodiments, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be arranged outside the second side window glass 1120.

[0387] Instrument cluster 1400 may be arranged in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a tachometer, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.

[0388] The center console 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a seat heater are disposed. The center console 1500 may be disposed on one side of the instrument cluster 1400 .

[0389] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, and the center console 1500 may be disposed between the passenger seat instrument panel 1600 and the instrument cluster 1400. In some embodiments, the instrument cluster 1400 may be disposed corresponding to the driver's seat, and the passenger seat instrument panel 1600 may be disposed corresponding to the passenger seat. In some embodiments, the instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0390] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In some embodiments, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the instrument cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.

[0391] The display device 2 may include an organic light emitting display, an inorganic electroluminescent display, and / or a quantum dot display, etc. Hereinafter, as a display device 2 according to one or more embodiments, an organic light emitting display device including a light emitting device will be described as an example, but one or more appropriate types (kinds) of display devices as described above may be used in the embodiments.

[0392] See also Fig. 6A In one or more embodiments, the display device 2 may be arranged on the center console 1500. In some embodiments, the display device 2 may display navigation information. In some embodiments, the display device 2 may display audio, video, or information about vehicle settings.

[0393] See also Figure 6B In one or more embodiments, the display device 2 may be arranged on the instrument cluster 1400. In this case, the instrument cluster 1400 may display driving information and the like through the display device 2. In some embodiments, the instrument cluster 1400 may be implemented digitally. The instrument cluster 1400 may digitally display vehicle information and driving information as images. In some embodiments, the needle and instrument of the tachometer and one or more appropriate warning light icons may be displayed through digital signals.

[0394] See also Figure 6CIn one or more embodiments, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500.

[0395] Manufacturing method

[0396] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be each formed in a specific region by using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and / or laser induced thermal imaging.

[0397] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C. ... -8 About 10 -3 Torr range and under vacuum at about / second to about The deposition is carried out at a deposition rate in the range of 200 Å / s.

[0398] Definition of terms

[0399] As used herein, the term "C 3 -C 60 "Carbocyclyl" refers to a cyclic group that includes only carbon (e.g., consists of carbon) as a ring-forming atom and has 3 to 60 carbon atoms, and the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including a hetero atom as a ring-constituting atom in addition to the carbon atom. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may each be a monocyclic group including one (eg, exactly one) ring (eg, consisting of one ring) or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group may be 3 to 61.

[0400] As used herein, the term "cyclic group" may include (eg, simultaneously include) C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.

[0401] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.

[0402] In one or more embodiments,

[0403] C 3 -C 60 The carbocyclic group may be i) a group T1 (e.g., one of the groups selected from the group T1) or ii) a fused ring group in which two or more groups T1 (e.g., two or more of the groups selected from the group T1) are fused to each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentaphenanthrenyl group, a heptalenyl group, a tetracenyl group, a phenanthrenyl group, a hexacenyl group, a pentacene group, a rubinyl group, a coronet group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, or an indenoanthryl group),

[0404] C 1 -C 60The heterocyclic group may be i) a group T2, ii) a condensed ring group in which two or more groups T2 are condensed to each other, or iii) a condensed ring group in which at least one group T2 (e.g., at least one of the groups selected from the group T2) and at least one group T1 (e.g., at least one of the groups selected from the group T1) are condensed to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothioyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothioyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofurancarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzo naphthothioyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenylodibenzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazoline, benzoquinazolinyl, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, etc.),

[0405] Pi-electron-rich C 3 -C 60 The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl and / or benzothiophenylodibenzothiophenyl, etc.),

[0406] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl , benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl and / or azadibenzofuranyl, etc.),

[0407] The radical T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0408] The radical T2 can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

[0409] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiolyl or borocyclopentadienyl, and

[0410] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0411] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 A "cyclic group" may refer to a group fused with any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula using the corresponding term. In one or more embodiments, "phenyl" may be benzo, phenyl and / or phenylene, etc., and those of ordinary skill in the art may easily understand these groups based on the structure of the formula including "phenyl".

[0412] Depending on the context, in the present disclosure, a divalent group may refer to or may include a multivalent group (eg, trivalent, tetravalent, etc., not just divalent), depending on, for example, the structure of a formula associated with the term used.

[0413] For example, the unit price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Non-limiting examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and a divalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Non-limiting examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

[0414] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, for example, 1 -C 20 The term "alkyl" as used herein may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has substantially the same structure as a divalent group.

[0415] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, for example, 2 -C 20 The term "C-alkenyl" as used herein may include vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 The alkenyl group has a divalent group having substantially the same structure.

[0416] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group has at least one carbon-carbon triple bond in the middle or at the end, for example, 2 -C 20 Alkynyl, and non-limiting examples thereof may include ethynyl and propynyl. As used herein, the term “C2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups have substantially the same structure as a divalent group.

[0417] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 Alkyl) represented by a monovalent group, for example, C 1 -C 20 The alkoxy group, and non-limiting examples thereof may include a methoxy group, an ethoxy group, and an isopropoxy group.

[0418] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group comprising 3 to 10 carbon atoms. As used herein, C 3 -C 10 Non-limiting examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo [2.2.1] heptyl), bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl or bicyclo [2.2.2] octyl. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0419] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to the carbon atoms, and non-limiting examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.

[0420] As used herein, the term "C 3 -C 10The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has basically a divalent group of the same structure.

[0421] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent cyclic group having 1 to 10 carbon atoms in its ring, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having at least one double bond. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10 The heterocycloalkenyl group has basically a divalent group of the same structure.

[0422] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, 6 -C 30 Aryl, and as used herein the term "C 6 -C 60 "Arylene" refers to a divalent radical of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, 6 -C 30 Arylene. C 6 -C 60 Non-limiting examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, and ovalenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

[0423] As used herein, the term "C 1 -C 60The term "heteroaryl" refers to a monovalent group having a heterocyclic aromatic system, which has 1 to 60 carbon atoms and further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, for example, C 1 -C 30 As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system, which has 1 to 60 carbon atoms and further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, for example, C 1 -C 30 Heteroarylene. 1 -C 60 Non-limiting examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.

[0424] The term "monovalent non-aromatic fused polycyclic group" as used in this article refers to a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring atoms, and no aromaticity in its molecular structure when considered as a whole. Non-limiting examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and indenoanthryl. The term "divalent non-aromatic fused polycyclic group" as used in this article refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.

[0425] The term “monovalent non-aromatic fused heteropolycyclic group” as used herein refers to a monovalent group having two or more rings fused to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having non-aromaticity in its molecular structure when considered as a whole. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothioyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole, thiazolyl, oxadiazole, thiadi ... The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0426] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 aryl).

[0427] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59aryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 heteroaryl).

[0428] As used herein, the term " 10a " can be:

[0429] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0430] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0431] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

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

[0433] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or

[0434] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0435] As used herein, the term "heteroatom" refers to any atom other than a carbon atom and a hydrogen atom. Non-limiting examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0436] The term “transition metal” as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt) and / or gold (Au), among others.

[0437] The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, and the terms "tert-Bu" or "Bu" as used herein refer to an ethyl group. t ” refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

[0438] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In some embodiments, the "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0439] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0440] The maximum number of carbon atoms in the definition of a substituent is an example. For example, as C 1 -C 60 The maximum number of carbon atoms in an alkyl group is 60, which is an example, and the definition of an alkyl group also applies to C 1 -C 20 The other instances may be independently the same.

[0441] Unless otherwise defined, *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula.

[0442] Hereinafter, a compound and a light-emitting device according to one or more embodiments will be described in more detail with reference to the following examples.

[0443] Example

[0444] Synthesis of compounds

[0445] Synthesis Example 1: Synthesis of Compound 2

[0446]

[0447] Synthesis of intermediate 2-1

[0448] 2.70 g (10 mmol) of 1,3-dibromo-5-chlorobenzene, 3.49 g (20 mmol) of diphenylamine, 0.92 g (1 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.48 g (2 mmol) of P(t-Bu) 3 and 5.76 g (60 mmol) of sodium tert-butoxide were dissolved in 60 mL of toluene, and then stirred at 80° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0449] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 3.13 g (yield: 70%) of Intermediate 2-1. The obtained compound was identified by liquid chromatography-mass spectrometry (LC-MS). 30 H 23C1N 2 :M + 446.9

[0450] Synthesis of intermediate 2-2

[0451] 4.47 g (10 mmol) of intermediate 2-1, 2.68 g (12 mmol) of 5,9,9-trimethyl-9H-fluoren-2-amine, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of o-xylene, and then stirred at 140° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0452] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 4.12 g (yield: 65%) of Intermediate 2-2. The obtained compound was identified by LC-MS. 46 H 39 N 3 :M + 633.8

[0453] Synthesis of compound 2

[0454] 6.34 g (10 mmol) of intermediate 2-2, 3.49 g (10 mmol) of 4-bromo-1,1'-biphenyl, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of toluene, and then stirred at 80° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0455] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 5.50 g (yield: 70%) of Compound 2. The product was purified by mass spectrometry / fast atom bombardment (MS / FAB) and 1 The compounds were identified by H nuclear magnetic resonance spectroscopy (NMR).

[0456] Synthesis Example 2: Synthesis of Compound 6

[0457]

[0458] Compound 6 was synthesized in essentially the same manner as compound 2, except that 2-bromonaphthalene was used instead of 4-bromo-1,1'-biphenyl. 1 The obtained compound was identified by H NMR.

[0459] Synthesis Example 3: Synthesis of Compound 17

[0460]

[0461] Compound 17 was synthesized in essentially the same manner as compound 2, except that 4"-chloro-3'-phenyl-1,1':2',1"-terphenyl was used instead of 4-bromo-1,1'-biphenyl. 1 The obtained compound was identified by H NMR.

[0462] Synthesis Example 4: Synthesis of Compound 26

[0463]

[0464] Compound 26 was synthesized in essentially the same manner as compound 2, except that 2-bromo-1-phenylnaphthalene was used instead of 4-bromo-1,1'-biphenyl. 1 The obtained compound was identified by H NMR.

[0465] Synthesis Example 5: Synthesis of Compound 44

[0466]

[0467] Synthesis of Intermediate 44-1

[0468] 4.47 g (10 mmol) of intermediate 2-1, 2.03 g (12 mmol) of [1,1'-biphenyl]-4-amine, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of o-xylene, and then stirred at 140° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0469] The collected organic layers were washed with MgSO4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 3.77 g (yield: 65%) of Intermediate 44-1. The obtained compound was identified by LC-MS. 42 H 33 N 3 :M + 579.7

[0470] Synthesis of compound 44

[0471] 5.80 g (10 mmol) of Intermediate 44-1, 4.11 g (10 mmol) of 2-bromo-5-methyl-9,9-diphenyl-9H-fluorene, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of toluene, and then stirred at 80° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0472] The collected organic layers were washed with MgSO 4 The residue obtained by drying and evaporating the solvent was separated and purified by silica gel chromatography to obtain 6.37 g (yield: 70%) of Compound 44. 1 The obtained compound was identified by H NMR.

[0473] Synthesis Example 6: Synthesis of Compound 46

[0474]

[0475] Compound 46 was synthesized in essentially the same manner as compound 44, except that [1,1'-biphenyl]-2-amine was used instead of [1,1'-biphenyl]-4-amine. 1 The obtained compound was identified by H NMR.

[0476] Synthesis Example 7: Synthesis of Compound 56

[0477]

[0478] Compound 56 was synthesized in substantially the same manner as compound 2, except that 4-chloro-4'-cyclohexyl-1,1'-biphenyl was used instead of 4-bromo-1,1'-biphenyl. 1 The obtained compound was identified by H NMR.

[0479] Synthesis Example 8: Synthesis of Compound 82

[0480]

[0481] Synthesis of Intermediate 82-1

[0482] 2.87 g (10.0 mmol) of 2-bromo-5,9,9-trimethyl-9H-fluorene, 1.56 g (10.0 mmol) of (4-chlorophenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh 3 ) 4 and 4.14 g (30.0 mmol) of K 2 CO 3 Dissolve in 60 mL of tetrahydrofuran (THF) / H 2 O (2 / 1) mixed solution, and then stirred at 80° C. for 16 hours. The reaction solution was cooled at room temperature, and then an extraction process was performed three times using 60 mL of water and 60 mL of diethyl ether.

[0483] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 1.60 g (yield: 50%) of Intermediate 82-1. The obtained compound was identified by LC-MS. 22 H 19 Cl:M + 318.8

[0484] Synthesis of compound 82

[0485] 3.19 g (10 mmol) of Intermediate 82-1, 5.80 g (10 mmol) of Intermediate 44-1, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of o-xylene, and then stirred at 130° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0486] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 6.03 g (yield: 70%) of Compound 82. MS / FAB and 1The obtained compound was identified by H NMR.

[0487] Synthesis Example 9: Synthesis of Compound 89

[0488]

[0489] Synthesis of Intermediate 89-1

[0490] 4.47 g (10 mmol) of intermediate 2-1, 2.10 g (12 mmol) of 4-cyclohexylaniline, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of o-xylene, and then stirred at 140° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0491] The collected organic layers were washed with MgSO 4 After drying, the residue obtained by evaporating the solvent was separated and purified by silica gel chromatography to obtain 3.81 g (yield: 65%) of Intermediate 89-1. The obtained compound was identified by LC-MS. 42 H 39 N 3 :M + 585.7

[0492] Synthesis of compound 89

[0493] 5.86 g (10 mmol) of Intermediate 89-1, 3.19 g (10 mmol) of Intermediate 82-1, 0.46 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 )、0.24 g (1 mmol) of P(t-Bu) 3 and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of o-xylene, and then stirred at 140° C. for 3 hours. The reaction solution was cooled at room temperature, and then, 40 mL of water was added thereto, followed by three extraction processes using 50 mL of diethyl ether.

[0494] The collected organic layers were washed with MgSO 4 The residue obtained by drying and evaporating the solvent was separated and purified by silica gel chromatography to obtain 6.08 g (yield: 70%) of Compound 89. 1The obtained compound was identified by H NMR.

[0495] Synthesis Example 10: Synthesis of Compound 106

[0496]

[0497] Compound 106 was synthesized in substantially the same manner as compound 44, except that 2-bromo-5,9,9-triphenyl-9H-fluorene was used instead of 2-bromo-5-methyl-9,9-diphenyl-9H-fluorene. 1 The obtained compound was identified by H NMR.

[0498] Each of the compounds synthesized according to the synthesis examples 1 H NMR and MS / FAB are shown in Table 1. Those skilled in the art can easily recognize methods for synthesizing compounds other than the compounds synthesized in the Synthesis Examples by referring to the synthesis routes and starting materials.

[0499] Table 1

[0500]

[0501]

[0502] Manufacturing of light-emitting devices

[0503] Comparative Example 1

[0504] As an anode, a 15Ω / cm 2 A glass substrate of ITO electrode (product of Corning Incorporated) was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically treated with isopropyl alcohol and then pure water for 5 minutes each, cleaned by irradiation of ultraviolet rays and exposure to ozone for 30 minutes, and then mounted on a vacuum deposition apparatus.

[0505] NPD is deposited on the anode to form a layer with a thickness of HT3 is deposited on the hole injection layer to form a hole injection layer with a thickness of and then depositing CzSi on the hole transport layer to form a layer with a thickness of The emission auxiliary layer.

[0506] H125, H126, PD40 and DF14 were co-deposited on the emission auxiliary layer in a weight ratio of 42:42:15:1 to form a The emitting layer is formed by depositing TSPO1 on the emitting layer to form a A hole blocking layer with a thickness of 1000 mm / s is formed, and TPBi is deposited on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is deposited on the electron injection layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.

[0507]

[0508] Comparative Example 2

[0509] A light-emitting device was manufactured in substantially the same manner as in Comparative Example 1, except that Compound 1000 was used instead of HT3 in the hole transport layer.

[0510]

[0511] Example 1 to Example 10

[0512] A light-emitting device was each manufactured in substantially the same manner as in Comparative Example 1, except that the compound in Table 2 was used instead of HT3 in the respective hole transport layers.

[0513]

[0514] In order to evaluate the characteristics of each of the light emitting devices of the above Examples and Comparative Examples, the maximum emission wavelength was measured, and the 2 The driving voltage (V) and life (T 95 The driving voltage (V), lifespan (T) and luminous efficiency (cd / A) of each of the light-emitting devices were measured using a source meter (manufactured by Keithley Instrument Inc., 2400 series). 95 )(hr) and luminous efficiency (cd / A). The lifetime of the light-emitting device (T 95 The lifespan (T) is measured by measuring the time (in hours) taken to reach 95% of its initial brightness. The lifespan (T) is measured using ENC's lifespan measurement equipment (LTS96CH). 95 )(hr).

[0515] The results of evaluating the characteristics of each of the light emitting devices are shown in Table 2.

[0516] Table 2

[0517]

[0518]

[0519] HTL: hole transport layer; HT: hole transport host; ET: electron transport host

[0520] Referring to Table 2, it can be confirmed that each of the light-emitting devices of the embodiments has high light-emitting efficiency, low driving voltage, and long lifespan compared to the light-emitting device of the comparative example.

[0521] Particularly, in the case of Comparative Example 2, in which Compound 1000 in which the 2-position of the fluorenyl group was substituted was used, it was confirmed that the results were much worse than or not better than those of the Examples of the present disclosure.

[0522] A light-emitting device including the compound according to one or more embodiments has excellent or appropriate light-emitting efficiency and excellent or appropriate lifespan.

[0523] In the present disclosure, it will be understood that the terms “comprise(s)”, “include(s)” or “have / has” define the presence of specified features, integers, steps, operations, elements, components and / or groups thereof, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or groups thereof.

[0524] Throughout the present disclosure, when a component (such as a layer, film, region, or plate) is referred to as being placed "on" another component (such as a layer, film, region, or plate), it will be understood that it can be directly on the other component (such as a layer, film, region, or plate) or an intervening component (such as a layer, film, region, or plate) can be interposed therebetween. In some embodiments, "directly on" can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other components. For example, "directly on" can mean that two layers or two components are disposed without using additional components such as bonding components therebetween.

[0525] In the present disclosure, although the terms "first", "second", etc. may be used herein to describe one or more elements, components, regions and / or layers, these elements, components, regions and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another component.

[0526] As used herein, the singular forms "a", "an", "one", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure."

[0527] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. "About," as used herein, includes the specified value and means within the range of acceptable deviations of the particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations of a specified value, or within ±30%, ±20%, ±10%, or ±5% of a specified value.

[0528] Any numerical range described in this article is intended to include all sub-ranges of the same numerical precision within the range of description. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 described and the maximum value 10.0 described (and including 1.0 and 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit described in this article is intended to include all lower numerical limits included therein and any minimum numerical limit described in this disclosure is intended to include all higher numerical limits included therein. Accordingly, the applicant reserves the right to modify this disclosure (including claims) to explicitly describe any sub-ranges included within the range explicitly described in this article.

[0529] The light-emitting device, electronic device, display device / device, electronic equipment, electronic device or any other related device or component according to the embodiment of the present disclosure described herein can be implemented using any appropriate hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware and hardware. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on an independent IC chip. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP) or a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components to perform various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions can also be stored in other non-temporary computer-readable media, such as, for example, a CD-ROM or a flash drive. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a dedicated computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.

[0530] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of the features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more appropriate changes in form and details may be made therein without departing from the spirit and scope defined by the attached claims and their equivalents.

Claims

1. A compound represented by Formula 1: Formula 1 in, In formula 1, R1, R2, R4 and Ar1 to Ar5 are each independently hydrogen, deuterium, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a The substituted monovalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, R3 is unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl is either unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, Optionally, R1 and R2 are linked together to form a ring, L is a single bond, unsubstituted or replaced by at least one R 10a Substituted C6-C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a The substituted divalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group, m is an integer selected from 0 to 3, wherein when m is 2 or more, each L is the same as or different from each other, n is an integer selected from 0 to 3, wherein when n is 2 or greater, each R4 is the same as or different from each other, and Where R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

2. The compound according to claim 1, wherein Ar1 to Ar5 are each independently unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryl.

3. The compound according to claim 1, wherein Ar1 to Ar5 are each independently unsubstituted or substituted by at least one R 10a Substituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, coronenyl or ovalenyl.

4. The compound of claim 1, wherein each R4 is independently hydrogen or deuterium.

5. The compound according to claim 1, wherein R1 to R3 are each independently unsubstituted or substituted by at least one R 10a substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentalenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, corundum or ovalenyl.

6. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2: Formula 2 In formula 2, R1 to R3, Ar1, L and m are each the same as defined in Formula 1.

7. The compound according to claim 6, wherein R1 to R3 are each independently unsubstituted or substituted by at least one R 10a Substituted methyl, phenyl or naphthyl.

8. The compound according to claim 6, wherein Ar1 is unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryl, and R 10a is unsubstituted or replaced by C3-C 60 Carbocyclic substituted C3-C 60 Carbocyclic group.

9. The compound according to claim 1, comprising one selected from the following compounds:

10. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an interlayer between the first electrode and the second electrode and including an emission layer, Wherein the interlayer comprises the compound according to any one of claims 1 to 9.

11. The light emitting device according to claim 10, wherein the first electrode is an anode, The second electrode is a cathode, and The interlayer further includes a hole transport region between the first electrode and the emissive layer, and the hole transport region includes: hole transport layer; as well as A hole injection layer, an emission assisting layer, an electron blocking layer or any combination thereof. 12 . The light-emitting device according to claim 11 , wherein the hole transport layer comprises the compound according to any one of claims 1 to 9 .

13. The light emitting device according to claim 10, wherein the first electrode is an anode, The second electrode is a cathode, and The interlayer further includes an electron transport region between the second electrode and the emission layer, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The light emitting device according to claim 10 , wherein the emitting layer comprises two types of hosts. The light-emitting device according to claim 10 , wherein the emission layer comprises a hole transport host and an electron transport host. The light emitting device according to claim 10 , wherein the emission layer comprises two types of dopants. The light emitting device according to claim 10 , wherein the emission layer comprises a phosphorescent dopant and a fluorescent dopant.

18. An electronic device comprising the light emitting device according to any one of claims 10 to 17.

19. The electronic device according to claim 18, further comprising a thin film transistor, The thin film transistor comprises a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor.

20. An electronic device comprising an electronic device according to claim 18 or 19, wherein the electronic device is at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater screen, a stadium screen, a light therapy device and a sign.

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