Compound, light-emitting device including compound, and electronic device

Abstract

The invention relates to a compound, a light-emitting device including the compound, and an electronic device including the light-emitting device. The light emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes a compound represented by Formula 1. Details of Formula 1 are described in the disclosure. Formula 1

Description

[0001] Cross-references to related applications

[0002] This application claims priority to Korean Patent Application No. 10-2024-0136014, filed on October 7, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of this disclosure relate to compounds, light-emitting devices including compounds, and electronic devices including light-emitting devices. Background Technology

[0004] In light-emitting devices, self-emitting devices have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

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

[0006] One or more embodiments of this disclosure include a compound represented by Formula 1, a light-emitting device including a compound represented by Formula 1, and an electronic device including a light-emitting device.

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

[0008] One or more embodiments include a compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In Equation 1,

[0012] X1 can be N or CR 11 X2 can be N or CR 12 X3 can be N or CR 13 And at least one of X1 to X3 can be N.

[0013] X4 can be N or CR 14 X5 can be N or CR 15 X6 can be N or CR 16And at least one selected from X4 to X6 can be N.

[0014] R1 to R4 and R 11 To R 16 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 60 Alkyl thioyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),

[0015] Ar1 to Ar4 can each be independently unsubstituted or substituted by at least one R. 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10aReplacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups or unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups,

[0016] At least one selected from Ar1 to Ar4 may be an unsubstituted triphenyl, and

[0017] R 10a Possible forms:

[0018] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro,

[0019] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl groups; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C60 Heteroaryl alkyl groups.

[0023] According to one or more embodiments, the light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emitting layer, wherein the interlayer includes a compound represented by Formula 1.

[0024] According to one or more embodiments, the electronic device includes a light-emitting device. Attached Figure Description

[0025] The above and other aspects and features of specific embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:

[0026] Figure 1 This is a schematic cross-sectional view of the structure of the light-emitting device according to the embodiment;

[0027] Figure 2 A cross-sectional view of an electronic device according to an embodiment; and

[0028] Figure 3 This is a cross-sectional view of an electronic device according to another embodiment. Detailed Implementation

[0029] The embodiments illustrated in the accompanying drawings will now be explained in more detail with reference to examples thereof, wherein the same reference numerals refer to the same elements throughout. In this regard, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Accordingly, embodiments are described below solely with reference to the accompanying drawings to explain aspects of the embodiments described herein. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Throughout this disclosure, the expression “at least one of a, b, and c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0030] While existing electron transport materials are reported to have high luminous efficiency and long lifetime, further improvements in luminous efficiency and lifetime are necessary or beneficial to achieve fine pitch and low power consumption, thereby enabling the commercialization of mobile devices and large-scale TVs using light-emitting devices (e.g., organic light-emitting devices).

[0031] According to aspects of the implementation, the compound can be represented by Formula 1:

[0032] Formula 1

[0033]

[0034] In Equation 1,

[0035] X1 can be N or CR 11 X2 can be N or CR 12 X3 can be N or CR 13 And at least one of X1 to X3 can be N.

[0036] X4 can be N or CR 14 X5 can be N or CR 15 X6 can be N or CR 16 And at least one selected from X4 to X6 can be N.

[0037] R1 to R4 and R 11 To R 16 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 60 Alkyl thioyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),

[0038] Ar1 to Ar4 can each be independently unsubstituted or substituted by at least one R. 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups or unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups,

[0039] At least one of Ar1 to Ar4 may be an unsubstituted triphenyl.

[0040] R 10a Possible forms:

[0041] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0042] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;

[0043] Each of the unsubstituted or substituted C3-Cs as described below60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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

[0044] -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

[0045] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl groups; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.

[0046] The compounds represented by Formula 1 have terphenyl groups directly bonded to the triazine nucleus, resulting in excellent charge transport capabilities. Light-emitting devices incorporating compounds represented by Formula 1 can exhibit superior driving voltage, luminous efficiency, and lifetime.

[0047] According to the implementation method, the unsubstituted triphenyl group can be represented by formula Y1 or formula Y2:

[0048]

[0049] In formulas Y1 and Y2, the asterisk (*) indicates the bonding site with an adjacent atom.

[0050] According to the embodiments, the unsubstituted terphenyl may be any one selected from formula Y11 to Y25:

[0051]

[0052] In formulas Y11 to Y25, the asterisk (*) indicates the bonding site with an adjacent atom.

[0053] According to the embodiments, the remaining groups of Ar1 to Ar4 that are not unsubstituted terphenyl groups may each be independently unsubstituted or substituted with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl thiols or unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups. For example, the remaining groups of the non-unsubstituted terphenyl groups in Ar1 to Ar4 may each be independently unsubstituted or substituted by at least one R group. 10a Replacement C6-C 60 Aryl.

[0054] According to the implementation method, Ar1 or Ar2 may be an unsubstituted terphenyl.

[0055] According to the implementation method, Ar3 or Ar4 may be an unsubstituted terphenyl.

[0056] According to the implementation method, Ar1 or Ar3 may be an unsubstituted terphenyl.

[0057] According to the embodiments, R1 to R4 may each be independently -F, -Cl, -Br, -I, cyano, or unsubstituted or substituted with at least one R. 10a Replacement C1-C 60 alkyl.

[0058] According to the implementation method, R 11 and R 15 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 60 Alkyl thioyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).

[0059] Q1, Q2, and Q3 are as described above.

[0060] In embodiments, the compound represented by Formula 1 may include one selected from the following compounds:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] According to another aspect of the embodiment, the light-emitting device includes:

[0108] First electrode;

[0109] The second electrode facing the first electrode; and

[0110] An interlayer between the first and second electrodes and including an emission layer, wherein the interlayer may include a compound represented by Formula 1.

[0111] According to an embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the interlayer may be further included between the first electrode and the emitter layer and include a hole injection layer, a hole transport layer, an electron blocking layer, an emitter assist layer, or any combination thereof, of a hole transport region.

[0112] According to an embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the interlayer may be further included between the second electrode and the emitter layer and include an electron transport region comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0113] According to an embodiment, the electron transport region may include a compound represented by Formula 1. For example, the hole blocking layer may include a compound represented by Formula 1. For example, the electron transport layer may include a compound represented by Formula 1. For example, the electron injection layer may include a compound represented by Formula 1.

[0114] According to an embodiment, the emitter layer may include a first body, a second body, a first dopant, and a second dopant, wherein the first dopant may be a compound comprising a metal and a ligand, the ligand comprising an imidazole moiety, and the second dopant may be a compound comprising boron.

[0115] According to the implementation method, the first subject may be a hole transmission subject.

[0116] According to the implementation method, the second body may be an electronic transmission body.

[0117] The hole transporter can be a compound with strong hole properties. The expression "compound with strong hole properties" means a compound that readily accepts holes (e.g., readily accepts and / or transmits holes), and this property can be obtained by including a hole receiving portion (also known as a HT portion).

[0118] Such hole-receiving portions may include, for example, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives and / or indole derivatives) and / or aromatic amine compounds.

[0119] The electron transporter can be a compound with strong electronic properties. The expression "compound with strong electronic properties" means a compound that readily accepts electrons (e.g., readily accepts and / or transports electrons), and this property can be acquired by including an electron receiving portion (also known as an ET portion).

[0120] This electron-receiving portion may include, for example, heteroaromatic compounds lacking π electrons. For instance, the electron-receiving portion may include nitrogen-containing heteroaromatic compounds.

[0121] In the implementation, for compounds that include only the HT portion or only the ET portion, it is clear whether the compound has hole transport properties or electron transport properties.

[0122] The compound may include both HT and ET moieties. In this embodiment, a simple comparison of the total number of HT moieties and the total number of ET moieties present in the compound can be used as a criterion for predicting or determining whether the compound has hole transport properties or electron transport properties, but it is not an absolute criterion. One reason is that the ability of an HT moiety and an ET moieties to attract holes and electrons may not be exactly the same, respectively.

[0123] Therefore, a relatively reliable method for determining whether a compound with a given structure has hole transport properties or electron transport properties is to implement the compound directly in the device.

[0124] According to embodiments, the first body and the second body may have a weight ratio of 9:1 to 1:9. For example, the first body and the second body may have a weight ratio of 6:4 to 4:6. In embodiments where the weight ratio of the first body and the second body is within this range, the charge balance may be appropriate or suitable.

[0125] According to the implementation method, the metal of the first dopant may be a transition metal.

[0126] For example, the first dopant may include a compound represented by formula 401:

[0127] Formula 401

[0128] M(L 401 ) xc1 (L 402 ) xc2

[0129] Formula 402

[0130]

[0131] In Equations 401 and 402,

[0132] M can be titanium (Ti), cobalt (Co), copper (Cu), zinc (Zn), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), rhenium (Re), platinum (Pt), gold (Au), osmium (Os), iridium (Ir), or rhenium (Re).

[0133] L 401 It can be a ligand represented by Equation 402, and xc1 is 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0134] L 402It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, wherein when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.

[0135] X 401 and X 402 They can be nitrogen or carbon independently.

[0136] Ring A 401 And Ring A 402 Each can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,

[0137] T 401 It can be a single bond (e.g., a covalent 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 =,

[0138] X 403 and X 404 They can each be independently chemical bonds (e.g., covalent chemical bonds or coordinate covalent bonds, also known as coordinate bonds), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),

[0139] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 401 (Q) 402 (Q) 403 -N(Q) 401 (Q)402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) or -P(=O)(Q 401 (Q) 402 ),

[0140] Optional, R 401 and R 402 They can be connected to form a ring.

[0141] R 10a Possible forms:

[0142] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0143] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;

[0144] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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

[0145] -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

[0146] Q 11 To Q 13 Q 21 To Q 23 Q 31 To Q 33 Q 411 To Q 414 and Q 401 To Q 403 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl groups; each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 heteroaryl,

[0147] xc11 and xc12 can each be an integer selected from 0 to 10 independently.

[0148] In Equation 402, * and *' each indicate the binding site with M in Equation 401, and

[0149] Ring A 401 Or ring A 402 One of them may include the imidazole moiety.

[0150] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two rings A in 401 Optionally via T as a linking group 402 Connected to each other, or two or more L 401 The two rings A in 402 Optionally via T as a linking group 403 Interconnected. T 402 and T 403 Each as referenced in T 401 Described.

[0151] According to an embodiment, the second dopant may include a compound represented by Formula 2:

[0152] Formula 2

[0153]

[0154] In Equation 2, Y1 to Y3 can each be independently S, N(R) 24 ), B(R) 24 ), C(R 24 (R) 25 ) or Si(R 24 (R) 25 ),

[0155] c can be 0 or 1.

[0156] A 11 To A 13 Each can be independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic group,

[0157] R 21 To R 25Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0158] R 21 To R 25 They can optionally be connected to each other to form unsubstituted or by at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic group,

[0159] a21 to a23 can each be an integer selected from 0 to 10 independently.

[0160] R 10a Possible forms:

[0161] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0162] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;

[0163] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60Aryl alkyl, C2-C 60 Heteroaryl, -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

[0164] -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

[0165] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl groups; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.

[0166] According to the implementation method, the emitting layer may be a fluorescent emitting layer.

[0167] According to the implementation method, the emitting layer can be a blue emitting layer, that is, the emitting layer can emit blue light.

[0168] Another aspect of the embodiments of this disclosure provides an electronic device including a light-emitting device. The electronic device may further include a thin-film transistor. For example, the electronic device may further include a thin-film transistor including a source electrode and a drain electrode, wherein a first electrode of the light-emitting device is electrically connected to the source electrode or the drain electrode.

[0169] According to embodiments, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. Further details regarding the electronic device are the same as those provided elsewhere herein.

[0170] As used herein, the term “interlayer” refers to a single layer and / or multiple layers between the first and second electrodes of a light-emitting device.

[0171] Figure 1 Description

[0172] Figure 1 This is a schematic cross-sectional view of the structure of the light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, a sandwich layer 130, and a second electrode 150.

[0173] The following text is for reference only. Figure 1 The structure of the light-emitting device 10 according to the embodiment and the method of manufacturing the light-emitting device 10 are described.

[0174] First electrode 110

[0175] exist Figure 1 In this embodiment, the substrate may be located below the first electrode 110 and / or on the second electrode 150. A glass substrate and / or a plastic substrate may be used as the substrate. According to embodiments, the substrate may be a flexible substrate and may include plastics with excellent heat resistance and durability (e.g., polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).

[0176] The first electrode 110 can be formed, for example, by depositing and / 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 can be a high work function material that facilitates hole injection.

[0177] The first electrode 110 may be a reflective electrode, a transmissive-reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. According to an embodiment, when the first electrode 110 is a transmissive-reflective electrode or a reflective electrode, the material included in 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.

[0178] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. According to an embodiment, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0179] mezzanine 130

[0180] The interlayer 130 is on top of the first electrode 110. The interlayer 130 includes an emission layer.

[0181] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 150.

[0182] In addition to various suitable organic materials, the interlayer 130 may further include metal-containing compounds (e.g., organometallic compounds) and / or inorganic materials (e.g., quantum dots).

[0183] The interlayer 130 may include i) two or more emitting units stacked sequentially between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between two adjacent emitting units. When the interlayer 130 includes the emitting layer and the charge generation layer as described above, the light-emitting device 10 may be a series light-emitting device.

[0184] Hole transport region in interlayer 130

[0185] The hole transport region may have: i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of multiple materials that are different from each other, or iii) a multi-layer structure comprising multiple layers made of multiple materials that are different from each other.

[0186] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.

[0187] For example, 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 injection 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, wherein each layer in each structure is stacked sequentially from the first electrode 110.

[0188] For example, the hole transport region may have a multilayer structure of hole transport layers / emission auxiliary layers or hole transport layers / electron blocking layers stacked sequentially from the first electrode 110 in the order described below.

[0189] The hole transport region may include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof:

[0190] Formula 201

[0191]

[0192] Formula 202

[0193]

[0194] Among them, in equations 201 and 202,

[0195] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0196] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0197] xa1 to xa4 can each be an integer selected from 0 to 5 independently.

[0198] xa5 can be an integer selected from 1 to 10.

[0199] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0200] R 201 and R 202 Optionally via a single bond (e.g., a covalent single bond), unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group) (e.g., compound HT16),

[0201] R 203 and R 204 Optionally via a single bond (e.g., a covalent single bond), unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted alkenyl groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and

[0202] na1 can be an integer selected from 1 to 4.

[0203] According to an embodiment, each of formulas 201 and 202 may include at least one of the groups selected from formulas CY201 to CY217:

[0204]

[0205] In formulas CY201 to CY217, R 10b and R 10c Each as per R 10a The description, CY 201 To CY 204 Each can be independently C3-C 20 Carbocyclic or C1-C 20 Heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R-substituted. 10a replace.

[0206] According to the implementation method, the ring CY in formulas CY201 to CY217 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.

[0207] According to an embodiment, each of Formulas 201 and 202 may include at least one of the groups selected from Formulas CY201 to CY203.

[0208] According to an embodiment, formula 201 may include at least one group selected from formulas CY201 to CY203 and at least one group selected from formulas CY204 to CY217.

[0209] According to the implementation method, in formula 201, xa1 can be 1, R 201 It can be a group represented by one selected from formulas CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by one of the formulas CY204 to CY207.

[0210] According to an embodiment, each of Formulas 201 and 202 may not include groups represented by Formulas CY201 to CY203.

[0211] According to an embodiment, each of Formulas 201 and 202 may not include groups represented by Formulas CY201 to CY203, and may include at least one group selected from Formulas CY204 to CY217.

[0212] According to an embodiment, each of Formulas 201 and 202 may not include groups represented by Formulas CY201 to CY217.

[0213] According to embodiments, the hole transport region may include one selected from compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiroTPD, spiroNPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), CzSi, or any combination thereof:

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole transport layer can be approximately [missing information]. to approximately For example, about to approximately When the thickness of the hole transport region and the thickness of the hole transport layer are within the above range, appropriate or satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0220] The emission assist layer can increase luminous efficiency by compensating for the optical resonant distance of the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce electron leakage from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in both the emission assist layer and the electron blocking layer.

[0221] p-dopants

[0222] In addition to these materials, the hole transport region may further include charge-generating materials for improving conduction properties (e.g., electrical conductivity). The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of charge-generating materials).

[0223] The charge-generating material can be, for example, a p-doped agent.

[0224] For example, the LUMO level of a p-doped agent can be less than or equal to -3.5 eV.

[0225] According to embodiments, p-dopers may include quinone derivatives, cyano-containing compounds, compounds including elements EL1 and EL2, or any combination thereof.

[0226] Examples of quinone derivatives may include TCNQ and F4-TCNQ.

[0227] Examples of cyano-containing compounds may include HAT-CN and compounds represented by formula 221.

[0228]

[0229] Equation 221

[0230]

[0231] In Equation 221,

[0232] R 221 To R 223 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and

[0233] R 221 To R 223 At least one of them can be independently replaced by C3-C as described below. 60 Carbocyclic or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 20 Alkyl groups; or any combination thereof.

[0234] In a compound comprising elements EL1 and EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0235] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and / or cesium (Cs); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), and / or barium (Ba); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), and cobalt (C). (e.g., rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au); post-transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn); and lanthanides (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and / or lutetium (Lu).)

[0236] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).

[0237] Examples of nonmetals may include oxygen (O) and halogens (e.g., F, Cl, Br and / or I).

[0238] Examples of compounds including elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides and / or quasi-metal iodides), metal tellurides, or any combination thereof.

[0239] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3 and / or Mo2O5, etc.) and rhenium oxides (e.g., ReO3, etc.).

[0240] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0241] 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 CsI.

[0242] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0243] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4 and / or TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4 and / or ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4 and / or HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3 and / or VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3 and / or NbI3, etc.), and tantalum halides (e.g., TaF3, TaCl3, TaBr3, etc.). 3 and / or TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3 and / or CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3 and / or MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3 and / or WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2 and / or MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2 and / or TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2 and / or ReI2, etc.). Ferrous halides (e.g., FeF2, FeCl2, FeBr2 and / or FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 and / or RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2 and / or OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2 and / or CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2 and / or RhI2), iridium halides (e.g., IrF2, IrCl2, IrBr2). Nickel halides (e.g., NiF2, NiCl2, NiBr2 and / or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2 and / or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2 and / or PtI2), cuprous halides (e.g., CuF, CuCl, CuBr and / or CuI), silver halides (e.g., AgF, AgCl, AgBr and / or AgI), and gold halides (e.g., AuF, AuCl, AuBr and / or AuI).

[0244] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2 and / or ZnI2, etc.), indium halides (e.g., InI3, etc.) and tin halides (e.g., SnI2, etc.).

[0245] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.

[0246] Examples of quasi-metal halides may include antimony halides (e.g., SbCl5, etc.).

[0247] Examples of metal tellurides may include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te and / or Cs₂Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, F₂Te, etc.). (eTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.).

[0248] emission layer in interlayer 130

[0249] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. According to an embodiment, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with each other (e.g., physical contact) or separated from each other to emit white light. In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0250] The emitting layer may include a substrate and a dopant. The substrate may include a first substrate and a second substrate. The dopant may include the first dopant and the second dopant described above. For example, the first dopant may include a phosphorescent dopant, and the second dopant may include a delayed fluorescence dopant.

[0251] Based on 100 parts by weight of the total bulk, the amount of dopant in the emitter layer can range from about 0.01 parts by weight to about 35 parts by weight.

[0252] According to one embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or dopant in the emission layer.

[0253] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within the above range, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage.

[0254] main body

[0255] The subject may include a first subject and a second subject.

[0256] The first and second subjects may each independently include compounds represented by formula 301.

[0257] Formula 301

[0258] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,

[0259] In Equation 301,

[0260] Ar 301 and L 301 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0261] xb11 can be 1, 2, or 3.

[0262] xb1 can be an integer selected from 0 to 5.

[0263] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),

[0264] xb21 can be an integer selected from 1 to 5, and

[0265] Q 301 To Q 303 Each is as described in Q1.

[0266] According to the implementation method, when xb11 in formula 301 is 2 or greater, two or more Ar 301 They can be connected to each other via single bonds (e.g., covalent single bonds).

[0267] As another example, the first and second subjects may each independently comprise a compound represented by formula 301-1 below, a compound represented by formula 301-2 below, or any combination thereof:

[0268] Formula 301-1

[0269]

[0270] Formula 301-2

[0271]

[0272] Among them, in equations 301-1 and 301-2,

[0273] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0274] X 301 It can be O, S, N[(L 304 ) xb4-R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),

[0275] xb22 and xb23 can each be 0, 1, or 2 independently.

[0276] L 301 xb1 and R 301 Each as described with reference to formula 301 in this specification,

[0277] L 302 To L 304 Each independently, as referenced in L 301 Described,

[0278] xb2 to xb4 are each described independently as with reference to xb1, and

[0279] R 302 To R 305 and R 311 To R 314 Each as per R 301 Described.

[0280] As another example, the first and second bodies may each independently comprise an alkaline earth metal complex, a transition metal complex, or any combination thereof. According to embodiments, the bodies may include Be complexes (e.g., compound H55), Mg complexes, Zn complexes, or any combination thereof.

[0281] According to embodiments, the first and second bodies may each independently comprise one selected from compounds H1 to H128, compounds HT-1 to HT-4, compounds ET-1 to ET-3; 9,10-bis(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN); 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-bis(9-carbazolyl)benzene (mCP); 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), or any combination thereof:

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] Phosphorescent dopants

[0291] For phosphorescent dopants, refer to the first dopant mentioned above.

[0292] According to an embodiment, the amount of the first dopant present can be from about 1.0 part by weight to about 30 parts by weight (based on 100 parts by weight of the total body). In embodiments where the amount of the first dopant is within this range, the light-emitting device can have excellent luminous efficiency and lifetime.

[0293] The first dopant may include, for example, one selected from compounds PD26 to PD39, compound PS-1, and PS-2:

[0294]

[0295]

[0296] Delayed fluorescence materials

[0297] For information on delayed fluorescence materials, please refer to the second dopant mentioned above.

[0298] According to an embodiment, the amount of the second dopant can be from about 1.0 part by weight to about 7.0 parts by weight (based on 100 parts by weight of the total body). In embodiments where the amount of the second dopant is within this range, the light-emitting device can have excellent luminous efficiency and lifetime.

[0299] The second dopant may include, for example, any of the following compounds:

[0300]

[0301]

[0302]

[0303]

[0304] quantum dots

[0305] Electronic devices may include quantum dots. For example, an electronic device may include a color filter, and the color filter may include quantum dots.

[0306] As used herein, the term "quantum dot" refers to a crystal of a semiconductor compound and may include any material capable of emitting light of various suitable wavelengths depending on the size of the crystal. By adjusting the elemental proportions in the quantum dot compound, quantum dots can emit light of various suitable wavelengths.

[0307] The diameter of quantum dots can range from, for example, from about 1 nm to about 10 nm.

[0308] Quantum dots can be synthesized using wet chemical processes, metal-organic chemical vapor deposition (MOCVD), molecular beam epitaxy (MBE), and / or any similar processes.

[0309] The wet chemical process involves mixing a precursor material with an organic solvent and then growing quantum dot crystals. During quantum dot crystal growth, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystals and controls their growth, allowing for control of the quantum dot crystal growth through a less expensive and easier process than vapor deposition methods (e.g., metal-organic chemical vapor deposition or molecular beam epitaxy).

[0310] Quantum dots may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or any combination thereof.

[0311] Examples of group II-VI semiconductor compounds are binary compounds (e.g., CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS); ternary compounds (e.g., CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZn Se, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS); quaternary compounds (e.g., CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe); or any combination thereof.

[0312] Examples of Group III-V semiconductor compounds include: binary compounds (e.g., GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and InSb); ternary compounds (e.g., GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and InPSb); quaternary compounds (e.g., GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb); or any combination thereof. In embodiments, the Group III-V semiconductor compounds may further include Group II elements. Examples of group III-V semiconductor compounds that further include group II elements are InZnP, InGaZnP, and / or InAlZnP, etc.

[0313] Examples of group III-VI semiconductor compounds are: binary compounds (e.g., GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2Se3 and / or InTe); ternary compounds (e.g., InGaS3 and / or InGaSe3); or any combination thereof.

[0314] Examples of group I-III-VI semiconductor compounds are: ternary compounds (e.g., AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2 and / or AgAlO2, etc.); quaternary compounds (e.g., AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS and / or CuInGaS2, etc.); or any combination thereof.

[0315] Examples of group IV-VI semiconductor compounds are: binary compounds (e.g., SnS, SnSe, SnTe, PbS, PbSe and / or PbTe); ternary compounds (e.g., SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe); quaternary compounds (e.g., SnPbSSe, SnPbSeTe and / or SnPbSTe); or any combination thereof.

[0316] Group IV elements or compounds may include: single elements (e.g., Si and / or Ge); binary compounds (e.g., SiC and / or SiGe); or any combination thereof.

[0317] Each element included in a multi-element compound (e.g., binary, ternary, and quaternary compounds) may exist in the particles in a uniform or non-uniform concentration.

[0318] In implementations, quantum dots may have a single structure in which the concentration of each element in the quantum dot is uniform, or a core / shell dual structure. For example, the materials included in the core and the materials included in the shell may be different from each other.

[0319] The shell of a quantum dot can act as a protective layer, preventing or reducing chemical denaturation of the core to maintain semiconductor properties, and / or as a charging layer, imparting electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of elements present in the shell decreases along the direction towards the center of the core.

[0320] Examples of the shell for quantum dots can be oxides of metals, oxides of quasi-metals and / or oxides of nonmetals, semiconductor compounds and any combination thereof. Examples of oxides of metals, oxides of quasi-metals and / or oxides of nonmetals are binary compounds (e.g., SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO); ternary compounds (e.g., MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4); and any combination thereof. Examples of semiconductor compounds as described herein are Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; and any combination thereof. For example, semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnSTe, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0321] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity and / or color reproducibility can be increased. In embodiments, light emitted through these quantum dots is emitted in all directions (e.g., substantially all directions), which improves viewing angle.

[0322] In embodiments, quantum dots may be in the form of spherical nanoparticles (e.g., substantially spherical nanoparticles), conical nanoparticles (e.g., substantially conical nanoparticles), multi-armed nanoparticles, cubic nanoparticles (e.g., substantially cubic nanoparticles), nanotubes, nanowires, nanofibers, and / or nanoplates.

[0323] Because the band gap can be adjusted by controlling the size of the quantum dots, light with various suitable wavelength bands can be obtained from the quantum dot emitting layer. Accordingly, by using quantum dots of different sizes, light-emitting devices that emit light with various suitable wavelength bands can be implemented. In one or more embodiments, the size of the quantum dots can be selected to emit red, green, and / or blue light. In one embodiment, the size of the quantum dots can be configured such that various suitable colors of light can be combined to emit white light.

[0324] Electron transport region in interlayer 130

[0325] The electron transport region may have: i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer comprising a variety of different materials, or iii) a multi-layer structure comprising multiple layers comprising a variety of different materials.

[0326] The electron transport region may include: an electron transport layer; and a hole blocking layer, an electron injection layer, or any combination thereof.

[0327] For example, 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, the constituent layers are stacked sequentially from the emitter layer.

[0328] The electron transport region (e.g., a hole-blocking layer or electron transport layer within the electron transport region) may include a metal-free compound comprising at least one π-electron-deficient nitrogen-containing C1-C. 60 Cyclic groups.

[0329] According to an embodiment, the electron transport region may include a compound represented by Formula 601.

[0330] Formula 601

[0331] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0332] In Equation 601,

[0333] Ar 601 and L 601Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,

[0334] xe11 can be 1, 2, or 3.

[0335] xe1 can be 0, 1, 2, 3, 4, or 5.

[0336] R 601 It can be unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),

[0337] Q 601 To Q 603 Each as described in Q1,

[0338] xe21 can be 1, 2, 3, 4, or 5, and

[0339] Selected from Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups.

[0340] According to the implementation method, when xe11 in formula 601 is 2 or greater, two or more Ar 601 They can be linked together by a single bond (e.g., a covalent bond).

[0341] According to the implementation method, Ar in Formula 601 601 It can be unsubstituted or by at least one R 10a Substituted anthracene group.

[0342] According to an embodiment, the electron transport region may include a compound represented by formula 601-1:

[0343] Formula 601-1

[0344]

[0345] In Equation 601-1,

[0346] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,

[0347] L 611 To L 613 Each as referenced in L 601 Described,

[0348] xe611 to xe613 are each as described with reference to xe1.

[0349] R 611 To R 613 Each as per R 601 Described, and

[0350] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.

[0351] According to the implementation method, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.

[0352] The electron transport region may include one selected from compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, TSPO1, TPBi, or any combination thereof:

[0353]

[0354]

[0355]

[0356]

[0357] The thickness of the electron transport region can be approximately to approximately For example, about to approximately 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 or the electron transport layer can be independently approximately [missing information]. to approximately For example, about to approximately Furthermore, the thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the hole blocking layer and / or electron transport layer is within the ranges described above, appropriate or satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0358] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.

[0359] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. Ligands coordinated with the metal ions of the alkali metal complex or the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.

[0360] According to embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) and / or compound ET-D2:

[0361]

[0362] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 150.

[0363] The electron injection layer may have: i) a single-layer structure composed of a single layer made of a single material, ii) a single-layer structure composed of a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers, the plurality of layers including a plurality of different materials.

[0364] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0365] 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.

[0366] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides, etc.), tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

[0367] The alkali metal compound may include: alkali metal oxides (such as, Li2O, Cs2O, and / or K2O); alkali metal halides (such as, LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI); or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides (such as, BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1)). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. According to an embodiment, the rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.

[0368] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include i) one of the ions of alkali metals, alkaline earth metals, and rare earth metals, and ii) a ligand bonded to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.

[0369] As described above, the electron-injected layer may include or consist of the following: alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof. According to embodiments, the electron-injected layer may further include organic materials (e.g., compounds represented by Formula 601).

[0370] According to embodiments, the electron-injected layer may include or consist of the following: i) an alkali metal compound (e.g., an alkali metal halide); ii) a) an alkali metal compound (e.g., an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. According to embodiments, the electron-injected layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, and / or a LiF:Yb co-deposited layer, etc.

[0371] When the electron injection layer further includes organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic materials.

[0372] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately When the thickness of the electron injection layer is within the range described above, appropriate or satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0373] Second electrode 150

[0374] The second electrode 150 is on the interlayer 130. The second electrode 150 may be a cathode serving as an electron injection electrode, and may be made of metals, alloys, conductive compounds, or any combination thereof, each having a low work function, as materials for forming the second electrode 150.

[0375] 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 transmission electrode, a transmission-reflection electrode, or a reflection electrode.

[0376] The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.

[0377] Capping layer

[0378] The first capping layer may be outside the first electrode 110 and / or the second capping layer may be outside the second electrode 150. In an embodiment, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked sequentially in the described order, or in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the described order, or in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the described order.

[0379] Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted outward through the first electrode 110, which serves as a transmissive or reflective electrode, and the first capping layer. Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted outward through the second electrode 150, which serves as a transmissive or reflective electrode, and the second capping layer.

[0380] The first and second capping layers can increase the external emission efficiency based on the principle of constructive interference. Correspondingly, the light extraction efficiency of the light-emitting device 10 is increased, thereby increasing the luminous efficiency of the light-emitting device 10.

[0381] Each of the first and second capping layers may include a material with a refractive index of 1.6 or greater (at a wavelength of 589 nm).

[0382] The first capping layer and the second capping layer can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic composite capping layer including both organic and inorganic materials.

[0383] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthyl phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to an embodiment, at least one of the first and second capping layers may independently comprise an amino-containing compound.

[0384] According to an embodiment, at least one selected from 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.

[0385] According to an embodiment, at least one of the first capping layer and the second capping layer may each independently include one selected from compounds HT28 to HT33, one selected from compounds CP1 to CP6, β-NPB, or any combination thereof:

[0386]

[0387] electronic devices

[0388] Light-emitting devices can be included in a variety of suitable electronic devices. For example, electronic devices that include light-emitting devices can be light-emitting devices and / or authentication devices, etc.

[0389] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be provided in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light. A detailed description of the light-emitting device is provided above. According to embodiments, the color conversion layer may include quantum dots. Quantum dots may be, for example, as described herein.

[0390] The electronic device may include a substrate. The substrate may include multiple sub-pixel regions, the color filter may include multiple color filter regions corresponding to the multiple sub-pixel regions, and the color conversion layer may include multiple color conversion regions corresponding to the multiple sub-pixel regions.

[0391] The pixel-defining film exists between multiple sub-pixel regions and defines each sub-pixel region.

[0392] The color filter may further include a plurality of color filter areas and provide a light-shielding pattern between the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and provide a light-shielding pattern between the plurality of color conversion areas.

[0393] Multiple color filter regions (or multiple color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting 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. According to an embodiment, 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. According to an embodiment, the multiple color filter regions (or multiple color conversion regions) may include quantum dots. More specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. A detailed description of quantum dots is provided herein. The first region, the second region, and / or the third region may each further include a scatterer (e.g., a light scatterer).

[0394] According to an embodiment, the light-emitting device can emit first light, a first region can absorb the first light to emit light of a first-i-th color, a second region can absorb the first light to emit light of a second-i-th color, and a third region can absorb the first light to emit light of a third-i-th color. In an embodiment, the first-i-th color light, the second-i-th color light, and the third-i-th color light can have different maximum emission wavelengths. More specifically, the first light can be blue light, the first-i-th color light can be red light, the second-i-th color light can be green light, and the third-i-th color light can be blue light.

[0395] In addition to the light-emitting device as 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 any one of the source electrode and the drain electrode is electrically connected to one of the first and second electrodes of the light-emitting device.

[0396] Thin-film transistors may further include gate electrodes and / or gate insulating films, etc.

[0397] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors and / or oxide semiconductors, etc.

[0398] The electronic device may further include a sealing portion that encapsulates the light-emitting device. The sealing portion may be located between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, while simultaneously (e.g., synchronously) preventing or reducing the penetration of ambient air and moisture into the light-emitting device. The sealing portion may be a sealing substrate comprising a transparent glass substrate and / or a plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising at least one layer selected from organic and inorganic layers. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0399] Depending on the intended use of the electronic device, various suitable functional layers may also be additionally present on the sealed portion, in addition to color filters and / or color conversion layers. Examples of functional layers may include a touchscreen layer and a polarizing layer. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, and / or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by utilizing biometric information from a living body (e.g., fingertips and / or pupils).

[0400] In addition to the light-emitting device described above, the authentication device may further include a biometric information collector.

[0401] Electronic devices can be applied to a variety of suitable displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebook computers, electronic notebooks, electronic dictionaries, video game devices, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices and / or endoscopic displays), fish finders, various suitable measuring devices, instruments (e.g., instruments for vehicles, aircraft and / or ships) and / or projectors, etc.

[0402] Figure 2 and Figure 3 Description

[0403] Figure 2 This is a cross-sectional view of an electronic device according to an embodiment.

[0404] Figure 2 The electronic device includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a sealing portion 300 that seals the light-emitting device.

[0405] The substrate 100 may be a flexible substrate, a glass substrate, and / or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

[0406] The TFT may be located 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.

[0407] The active layer 220 may include inorganic semiconductors (e.g., silicon or polysilicon), organic semiconductors or oxide semiconductors, and may include source regions, drain regions and channel regions.

[0408] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 (e.g., electrically insulating) may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.

[0409] The interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 and the source electrode 260 from each other (e.g., electrically), and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 and the drain electrode 270 from each other (e.g., electrically).

[0410] Source electrode 260 and drain electrode 270 may be on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may expose the source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact (e.g., physically contact) the exposed portions of source and drain regions of active layer 220.

[0411] The TFT can be electrically connected to a light-emitting device to drive the light-emitting device, and can be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film (e.g., an inorganic electrical insulating film), an organic insulating film (e.g., an organic electrical 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, a sandwich layer 130, and a second electrode 150.

[0412] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.

[0413] A pixel defining film 290, including an insulating material (e.g., an electrically insulating material), may be present on the first electrode 110. The pixel defining film 290 may expose a specific area of ​​the first electrode 110, and an interlayer 130 may be present within the exposed area of ​​the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film and / or a polyacrylic acid-based organic film. In an embodiment, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290, and are provided as a common layer.

[0414] The second electrode 150 may be on the interlayer 130, and the capping layer 170 may be additionally on the second electrode 150. The capping layer 170 may cover the second electrode 150.

[0415] The sealing portion 300 may be on the capping layer 170. The sealing portion 300 may be on the light-emitting device to protect it from moisture and / or oxygen. The sealing portion 300 may include an inorganic film, including silicon nitride (SiN). x ), silicon oxide (SiO) xIndium tin oxide, indium zinc oxide, or any combination thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or combinations of inorganic and organic membranes.

[0416] Figure 3 This is a cross-sectional view of an electronic device according to another embodiment.

[0417] Figure 3 electronic devices and Figure 2 The electronic devices are essentially the same, except that the light-shielding pattern 500 and the functional area 400 are additionally located on the sealed 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. According to the embodiment, Figure 3 The light-emitting device included in the electronic device may be a series light-emitting device.

[0418] Manufacturing method

[0419] By using various appropriate methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing and / or laser-induced thermal imaging, etc.), the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region can be provided in specific regions.

[0420] When forming layers constituting hole transport regions, emission regions, and electron transport regions via vacuum deposition, the deposition temperature can range from about 100°C to about 500°C, depending on the materials included in the layers to be formed and the structure of the layers. -8 To about 10 -3 The vacuum level within the range of Tor and in approximately to approximately The deposition rate is carried out within a certain range.

[0421] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, taking into account the materials included in the layers to be formed and the structure of the layers to be formed.

[0422] Terminology limitations

[0423] As used in this article, the term "C3-C" 60"Carbocyclic group" refers to a cyclic group consisting only of carbon atoms as cyclic atoms and having 3 to 60 carbon atoms, and as used herein, the term "C1-C" is used in conjunction with "C1-C". 60 A "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms as cyclic atoms in addition to carbon atoms. (C3-C) 60 Carbocyclic groups and C1-C 60 The heterocyclic group can be a monocyclic group consisting of a single ring or a polycyclic group in which two or more rings are fused together. According to embodiments, C1-C 60 The number of cyclic atoms in a heterocyclic group can range from 3 to 61.

[0424] As used herein, the term "cyclic group" may include C3-C 60 Carbocyclic groups and C1-C 60 Both heterocyclic groups.

[0425] As used in this article, the term "π-electron-rich C3-C" 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and excluding *-N=*' as a cyclic moiety, and as used herein, the term "π-electron-deficient nitrogen-containing C1-C" is used. 60 "Cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as the cyclic part.

[0426] In the implementation,

[0427] C3-C 60 The carbocyclic group can be i) group T1 or ii) a fused-ring group in which two or more groups T1 are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentaenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, peryl, penfenyl, heptaenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indole, fluorenyl, spirodifluorenyl, benzofluorenyl, indophenantyl, or indoanthrayl).

[0428] C1-C 60The heterocyclic group can be i) group T2, ii) a fused-ring group in which two or more groups T2 are fused together, or iii) a fused-ring group in which at least one group T2 and at least one group T1 are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranocarbazole, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranodibenzofuranyl, benzofuranyl... Brønsted dibenzothiophene, benzothiophene dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzyl (e.g., benzo[i]isoquinolinyl, quinoxalinyl, benzo[i]quinoxalinyl, quinazolinyl, benzo[i]quinoxalinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazo[i]pyridinyl, imidazo[i]pyrimidinyl, imidazo[i]triazinyl, imidazo[i]pyrazinyl, imidazo[i]pyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiopheneyl, azadibenzothiopheneyl and / or azadibenzofuranyl, etc.)

[0429] C3-C rich in π electrons 60 The cyclic group may be i) group T1, ii) a fused ring group in which two or more groups T1 are fused together, iii) group T3, iv) a fused ring group in which two or more groups T3 are fused together, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused together (e.g., C3-C). 60 Carbocyclic, 1H-pyrrole, thiorrole, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiorrole, benzothiophene, benzofuranyl, carbazole, dibenzothiorrole, dibenzothiophene, dibenzofuranyl, indole-carbazole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiorrole-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthorrole, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene or benzothiophene-dibenzothiophene, etc.

[0430] Nitrogen-containing C1-C lacking π electrons 60The cyclic group may be i) group T4, ii) a fused ring group in which two or more groups T4 are fused together, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused together, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused together, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused together (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazole). The following groups are listed: benzo[i], benzimidazolyl, benzo[i]oxazolyl, benzo[i]isooxazolyl, benzo[i]thiazolyl, benzo[i]isothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzo[i]quinolinyl, benzo[i]isoquinolinyl, quinoxalinyl, benzo[i]quinoxalinyl, quinazolinyl, benzo[i]quinazolinyl, phenanthrolinel, cenolinyl, phthalazinyl, naphthidyl, imidazo[i]pyridyl, imidazo[i]pyrimidyl, imidazo[i]triazinyl, imidazo[i]pyrazinyl, imidazo[i]pyridazinyl, imidazo[i]pyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophene, and azadibenzofuranyl, etc.

[0431] Group T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptane), norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl.

[0432] The group T2 can be furanyl, thiopheneyl, 1H-pyrrolyl, thiopheneyl, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaboracyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, tetraazinyl, pyrrolylalkyl, imidazolyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, or dihydropyrazinyl.

[0433] Group T3 can be furanyl, thiophene, 1H-pyrrole, thiophene, or borocyclopentadienyl, and

[0434] The group T4 can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azirthiolyl, aziboranecyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.

[0435] As used herein, the terms "cyclic group", "C3-C" 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" can refer to a group whose structure, according to the formula using the corresponding term, is fused with any cyclic group, monovalent group, or polyvalent group (e.g., divalent, trivalent, and / or tetravalent groups, etc.). According to embodiments, "phenyl" can be benzo[a], phenyl, or phenylene, etc., which can be readily understood by those skilled in the art based on the structure of formulas including "phenyl".

[0436] For example, unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups, and divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.

[0437] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group of a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, and examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. As used herein, the term "C1-C" is used in conjunction with "C1-C". 60 "alkylene" refers to C1-C 60 Alkyl groups have essentially the same structure as divalent groups.

[0438] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 The alkyl group has at least one carbon-carbon double bond in its main chain (e.g., middle) or terminal (e.g., end). Examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" refers to a single-valent hydrocarbon group. 60 "Alkenyl" refers to C2-C 60 Alkenes are divalent groups with essentially the same structure.

[0439] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 The alkyl group has at least one monovalent hydrocarbon group on its main chain (e.g., middle) or terminal (e.g., end) with a carbon-carbon triple bond, and examples include ethynyl and propynyl. As used herein, the term "C2-C" refers to... 60 "Immyneyl" refers to C2-C 60 Alkynes are divalent groups with essentially the same structure.

[0440] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy, ethoxy, and isopropoxy.

[0441] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic cyclic group consisting of 3 to 10 carbon atoms in a monovalent saturated hydrocarbon. For example, C3-C... 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel (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 "C3-C" refers to... 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have divalent groups with essentially the same structure.

[0442] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms and further comprising at least one heteroatom as a cyclic atom in addition to the carbon atoms, and examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiopheneyl. As used herein, the term "C1-C" refers to... 10 "Heterocyclic alkyl" refers to C1-C 10Heterocyclic alkyl groups have divalent groups with essentially the same structure.

[0443] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond and being non-aromatic (e.g., not aromatic), and examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is used in conjunction with "cycloalkenyl". 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with essentially the same structure.

[0444] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a cyclic atom in addition to the carbon atoms, and having at least one double bond. C1-C 10 Examples of heterocyclic alkenyl groups are 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C" refers to... 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.

[0445] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C6-C" is used in conjunction with "aryl". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings can fused together.

[0446] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. As used herein, the term "C1-C" is used in conjunction with "C1-C". 60"Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system with 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings can fused together.

[0447] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, with only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, and which, when considered as a whole, is not aromatic in its molecular structure (e.g., not aromatic when considered as a whole). Examples of monovalent nonaromatic fused polycyclic groups include indenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, indeno[a]phenanthryl, and indeno[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused polycyclic group.

[0448] As used herein, the term “monovalent non-aromatic fused heterocyclic group” refers to a monovalent group having two or more rings fused together, further including at least one heteroatom as a cyclic atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity (e.g., not aromatic when considered as a whole) in its molecular structure. Examples of monovalent non-aromatic fused heterocyclic groups include pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azadibenzothiophene, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, isothiazolyl, oxadiazolyl, thiazolyl. Benzopyrazolyl, benzimidazoyl, benzoxazolyl, benzothiazoyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazoyl, indolocarbazoyl, benzofuranocarbazoyl, benzothiophenocarbazoyl, benzothiophenocarbazoyl, benzoindolocarbazoyl, benzocarbazoyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenodibenzothiophenyl, etc. As used herein, the term "divalent nonaromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused heteropolycyclic group.

[0449] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to the group consisting of -OA 102 (where A) 102 For C6-C 60 The aryl group is used to indicate a group, and as used herein, the term "C6-C" is used to refer to a group. 60 "Arylthio" refers to the group consisting of -SA 103 (where A) 103 For C6-C 60 (aryl) represents a group.

[0450] As used in this document, the term "C7-C" 60 "Aryl" refers to the group consisting of -A 104 A 105 (where A) 104 For C1-C 54 Alkylene, and A 105 For C6-C 59 The aryl group is used to indicate a group, and as used herein, the term "C2-C" is used to refer to a group. 60 "Heteroarylene" refers to compounds composed of -A 106 A107 (where A) 106 For C1-C 59 Alkylene, and A 107 For C1-C 59 (Heteroaryl) represents a group.

[0451] As used in this article, the term "C3-C" 60 "Carbocyclic group" includes C3-C 50 carbonyl group, C3-C 40 carbonyl group, C3-C 30 carbonyl group, C3-C 20 carbonyl group or C3-C 10 carbon cyclo group;

[0452] The term "C1-C" 60 "Heterocyclic groups" include C1-C 50 Heterocyclic groups, C1-C 40 Heterocyclic groups, C1-C 30 Heterocyclic groups, C1-C 20 Heterocyclic groups or C1-C 10 Heterocyclic groups;

[0453] The term "C1-C" 60 "alkyl" includes C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10 alkyl;

[0454] The term "C2-C" 60 "Alkenyl" includes C2-C 30 alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl;

[0455] The term "C2-C" 60 "Alkyne group" includes C2-C 30 alkynyl group, C2-C 20 alkynyl or C2-C 10 alkynyl group;

[0456] The term "C1-C" 60 "Alkoxy" includes C1-C 30 Alkoxy, C1-C 20 Alkoxy or C1-C 10 Alkoxy;

[0457] The term "C6-C" 60 "Aryl" includes C6-C 50 Aryl, C6-C 40 Aryl, C6-C 30 Aryl, C6-C20 Aryl or C6-C 15 Aryl;

[0458] The term "C1-C" 60 "Heteroary aryl" includes C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 Mixed aromatics;

[0459] The term "monovalent non-aromatic fused polycyclic group" includes C8-C 60 Monovalent non-aromatic fused polycyclic groups, C8-C 50 Monovalent non-aromatic fused polycyclic groups, C8-C 40 Monovalent non-aromatic fused polycyclic groups, C8-C 30 Monovalent non-aromatic fused polycyclic groups or C8-C 20 Monovalent non-aromatic fused polycyclic groups;

[0460] The term "monovalent non-aromatic fused heterocyclic group" includes C1-C 60 Monovalent non-aromatic fused heterocyclic groups, C1-C 50 Monovalent non-aromatic fused heterocyclic groups, C1-C 40 Monovalent non-aromatic fused heterocyclic groups, C1-C 30 Monovalent non-aromatic fused heterocyclic groups or C1-C 20 Monovalent non-aromatic fused heterocyclic groups;

[0461] The term "C6-C" 60 "Aryloxy groups" include C6-C 50 Aryloxy group, C6-C 40 Aryloxy group, C6-C 30 Aryloxy group, C6-C 20 aryloxy or C6-C 15 aryloxy;

[0462] The term "C6-C" 60 "Arylthio" includes C6-C 50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Aryl thiols or C6-C 15 Arylthio;

[0463] The term "C7-C" 60 "Aryl" includes C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30Aryl group, C7-C 20 Aryl or C7-C 15 Aryl alkyl groups; and

[0464] The term "C2-C" 60 "Heteroarylene" includes C2-C 50 Heteroaryl, C2-C 40 Heteroaryl, C2-C 30 Heteroaryl, C2-C 20 Heteroaryl or C2-C 15 Heteroaryl alkyl groups.

[0465] As used in this document, the term "R" 10a "Can be:

[0466] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0467] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;

[0468] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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

[0469] -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 ).

[0470] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 alkoxy; or

[0471] Each of the unsubstituted or replaced groups (deuterium, -F, cyano, C1-C) 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.

[0472] As used herein, the term "heteroatom" refers to any atom other than carbon and hydrogen atoms. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0473] As used herein, the term "transition metal" may include Hf, Ta, W, Re, Os, Ir, Pt, and / or Au, etc.

[0474] As used herein, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, and the term "tert-Bu" or "Bu" refers to ethyl. t "Refers to tert-butyl, and as used herein, the term "OMe" refers to methyl methacrylate (MMA).

[0475] As used herein, the term "biphenyl" refers to "a phenyl group substituted with a phenyl group". In embodiments, "biphenyl" is a phenyl group having a C6-C2 configuration. 60 Aryl groups are substituted phenyl groups.

[0476] As used herein, the term "terphenyl" refers to "a phenyl group substituted with a biphenyl group." In embodiments, "terphenyl" is a phenyl group having a C6-C substituted group. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.

[0477] The number of carbon atoms specified by the substituents is just an example. For example, in C1-C 60 In alkyl groups, 60 carbon atoms are used as an example, and the limitation of alkyl groups also applies to C1-C. 20 Alkyl groups. This also applies to other implementations.

[0478] Any hydrogen atoms in the compound structures described herein may optionally be replaced by deuterium.

[0479] Unless otherwise specified, * and *' as used herein refer to the bonding site with an adjacent atom in the corresponding formula. In the specification, "integers selected from 0 to 10" refers to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of numerical ranges also applies to any other numerical ranges appearing in the specification, such as integers selected from 0 and 1, integers selected from 0 to 2, integers selected from 0 to 3, integers selected from 0 to 4, integers selected from 0 to 5, integers selected from 0 to 6, integers selected from 0 to 7, integers selected from 0 to 8, and integers selected from 0 to 9, etc.

[0480] The light-emitting device according to the embodiments will be described in more detail below with reference to the embodiments.

[0481] Example

[0482] Synthesis Example 1 (Compound 1)

[0483]

[0484] Synthesis of intermediate compounds 1-2

[0485] Compound 1-1 (1.0 eq.) was added to tetrahydrofuran (THF) and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the resulting solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. After washing three times with ethyl acetate and water, the resulting organic layer was dried over MgSO4 under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 1-2 (yield: 68%).

[0486] Synthesis of intermediate compounds 1-3

[0487] Intermediate compounds 1-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Intermediate compounds 1-3 were obtained by column chromatography (yield: 73%).

[0488] Synthesis of Compound 1

[0489] Intermediate compounds 1-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Compound 1 was obtained by column chromatography (yield: 73%).

[0490] Synthesis Example 2 (Compound 6)

[0491]

[0492] Synthesis of intermediate compound 6-2

[0493] Compound 6-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the resulting solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. After washing three times with ethyl acetate and water, the resulting organic layer was dried over MgSO4 under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 6-2 (yield: 69%).

[0494] Synthesis of intermediate compound 6-3

[0495] Intermediate compound 6-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Intermediate compound 6-3 (yield: 74%) was obtained by column chromatography.

[0496] Synthesis of Compound 6

[0497] Intermediate compound 6-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Compound 6 was obtained by column chromatography (yield: 74%).

[0498] Synthesis Example 3 (Compound 7)

[0499]

[0500] Synthesis of intermediate compound 7-2

[0501] Compound 7-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the resulting solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. After washing three times with ethyl acetate and water, the resulting organic layer was dried over MgSO4 under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 7-2 (yield: 63%).

[0502] Synthesis of intermediate compound 7-3

[0503] Intermediate compound 7-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Intermediate compound 7-3 (yield: 73%) was obtained by column chromatography.

[0504] Synthesis of Compound 7

[0505] Intermediate compound 7-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Compound 7 was obtained by column chromatography (yield: 73%).

[0506] Synthesis Example 4 (Compound 9)

[0507]

[0508] Synthesis of intermediate compound 9-2

[0509] Compound 9-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. After washing three times with ethyl acetate and water, the resulting organic layer was dried over MgSO4 under reduced pressure. The solid was washed with water and methanol, and filtered to obtain intermediate compound 9-2 (yield: 68%).

[0510] Synthesis of intermediate compound 9-3

[0511] Intermediate compound 9-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting mixture was washed three times with ethyl acetate and water, and the obtained organic layer was dried over MgSO4 under reduced pressure. Intermediate compound 9-3 (yield: 75%) was obtained by column chromatography.

[0512] Synthesis of Compound 9

[0513] Intermediate compound 9-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 9 was obtained by column chromatography (yield: 73%).

[0514] Synthesis Example 5 (Compound 12)

[0515]

[0516] Synthesis of intermediate compound 12-2

[0517] Compound 12-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. The resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 12-2 (yield: 68%).

[0518] Synthesis of intermediate compound 12-3

[0519] Intermediate compound 12-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 12-3 was obtained by column chromatography (yield: 83%).

[0520] Synthesis of Compound 12

[0521] Intermediate compound 12-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 12 was obtained by column chromatography (yield: 71%).

[0522] Synthesis Example 6 (Compound 14)

[0523]

[0524] Synthesis of intermediate compound 14-2

[0525] Compound 14-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. The resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 14-2 (yield: 68%).

[0526] Synthesis of intermediate compound 14-3

[0527] Intermediate compound 14-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 14-3 (yield: 82%) was obtained by column chromatography.

[0528] Synthesis of Compound 14

[0529] Intermediate compound 14-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 14 was obtained by column chromatography (yield: 71%).

[0530] Synthesis Example 7 (Compound 15)

[0531]

[0532] Synthesis of intermediate compound 15-2

[0533] Compound 15-1 (1.0 eq.) was added to THF and cooled to -78 °C. Under a nitrogen atmosphere, n-butyllithium (1.05 eq.) was slowly added dropwise, and the mixture was stirred at -78 °C for 1 hour. Trimethyl borate (1.2 eq.) was slowly added dropwise to the solution at -78 °C, and the mixture was stirred at room temperature for 4 hours. HCl was then added dropwise, and the mixture was stirred at room temperature for 2 hours. The resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. The solid obtained was washed with water and methanol and filtered to obtain intermediate compound 15-2 (yield: 68%).

[0534] Synthesis of intermediate compound 15-3

[0535] Intermediate compound 15-2 (1.0 eq.), 2,4-dichloro-6-phenyl-1,3,5-triazine (compound A, 1.1 eq.), bis(triphenylphosphine)palladium(II) dichloride (0.02 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Intermediate compound 15-3 was obtained by column chromatography (yield: 82%).

[0536] Synthesis of Compound 15

[0537] Intermediate compound 15-3 (1.0 eq.), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)phenyl)-1,3,5-triazine (compound B, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 15 was obtained by column chromatography (yield: 71%).

[0538] Synthesis Example 8 (Compound 181)

[0539]

[0540] Synthesis of Compound 181

[0541] Intermediate compounds 1-3 (1.0 eq.), 2,4-diphenyl-6-(2,4,6-trimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound C, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 181 was obtained by column chromatography (yield: 72%).

[0542] Synthesis Example 9 (Compound 186)

[0543]

[0544] Synthesis of Compound 186

[0545] Intermediate compound 6-3 (1.0 eq.), 2,4-diphenyl-6-(2,4,6-trimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound C, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 186 was obtained by column chromatography (yield: 73%).

[0546] Synthesis Example 10 (Compound 192)

[0547]

[0548] Synthesis of Compound 192

[0549] Intermediate compound 12-3 (1.0 eq.), 2,4-diphenyl-6-(2,4,6-trimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-1,3,5-triazine (compound C, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene:EtOH:H2O (4:1:1 v / v) and stirred at 100 °C for 5 hours under a nitrogen atmosphere. After cooling, the resulting reaction solution was washed three times with ethyl acetate and water, and the resulting organic layer was first dried with MgSO4 and then dried again under reduced pressure. Compound 192 was obtained by column chromatography (yield: 74%).

[0550] For the compounds synthesized in Synthesis Examples 1 to 10, measurements were taken. 1 1H NMR and high-resolution mass spectrometry (HR-MS) were performed. The results are shown in Table 1. By referring to the synthetic routes and starting materials, those skilled in the art can easily identify the synthetic methods for compounds other than those in Synthetic Examples 1 to 10.

[0551] Table 1

[0552]

[0553]

[0554] Manufacturing of light-emitting devices

[0555] Comparative Example 1

[0556] 15Ω / cm will be formed as the anode 2 The glass substrate (Corning) of the ITO electrode is cut to a size of 50mm×50mm×0.7mm, ultrasonically cleaned with isopropanol and pure water for 5 minutes each, cleaned by ultraviolet (UV) irradiation and ozone exposure for 30 minutes, and then installed in a vacuum deposition equipment.

[0557] On the anode, NPD is deposited to form a structure with... A hole injection layer of a certain thickness was formed, and then HT3 was deposited on the hole injection layer to form a structure with... A hole transport layer of a certain thickness is formed, and then CzSi is deposited to form a hole transport layer with a thickness of [missing information]. A launch auxiliary layer of a certain thickness.

[0558] On the emission-assisted layer, referring to Table 2 below, a first substrate, a second substrate, a first dopant, and a second dopant are co-deposited in a weight ratio of 42:42:15:1 to form a layer with... The thickness of the emission layer.

[0559] Subsequently, TSPO1 is deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness was formed, and then TPBi was deposited on the hole-blocking layer to form a hole-blocking layer with a certain thickness. An electron transport layer of a certain thickness is formed, and then LiF is deposited on the electron transport layer to form an electron transport layer with a certain thickness. An electron-injected layer of a certain thickness is formed, and Al is deposited on the electron-injected layer to form a layer with... A cathode of a certain thickness is used to complete the manufacturing of the light-emitting device.

[0560] Comparative Examples 2 to 6

[0561] The light-emitting device was manufactured in essentially the same manner as Comparative Example 1, except that the corresponding compounds in Table 2 were used when forming the electron transport layer.

[0562] Examples 1 to 10

[0563] The light-emitting device was manufactured in essentially the same manner as Comparative Example 1, except that the corresponding compounds in Table 2 were used when forming the electron transport layer.

[0564]

[0565]

[0566] The results of the light-emitting device are shown in Table 2.

[0567] The driving voltage (V) of each of the light-emitting devices was measured using a source meter (Keithley Instrument, 2400 series), and the luminous efficacy (cd / A) and lifetime (T95) were measured using a Hamamatsu Optoelectronics measurement apparatus C9920-12. Lifetime (T95) represents the time required for the brightness of the light-emitting device to reach 95% of its initial brightness. Table 2 shows the lifetime (T95) as a percentage of the lifetime (T95) of Comparative Example 1.

[0568] Table 2

[0569]

[0570]

[0571] In HT / ET 1) In this context, HT stands for hole transport entity (first transport entity); ET stands for electron transport entity (second transport entity).

[0572] HT:ET = 5:5 (by weight)

[0573] Referring to Table 2, it can be seen that the driving voltage, luminous efficiency, and lifetime of Examples 1 to 10 are superior to those of Comparative Examples 1 to 6.

[0574] The light-emitting device according to the embodiment is superior to the light-emitting device of the prior art.

[0575] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The description of features or aspects in each embodiment should generally be taken into account for other similar features or aspects that may be used in other embodiments. Although one or more embodiments have been described with reference to the figures, those skilled in the art will understand that various suitable changes in form and detail may be made therein without departing from the spirit and scope defined by the claims and their equivalents.

Claims

1. A compound represented by Formula 1: Formula 1 in, In Equation 1, X1 is N or CR 11 X2 is N or CR 12 X3 is N or CR 13 And at least one of X1 to X3 is N. X4 is N or CR 14 X5 is N or CR 15 X6 is N or CR 16 And N is selected from at least one of X4 to X6. R1 to R4 and R 11 To R 16 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 60 Alkyl thioyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Ar1 through Ar4 are each independently unsubstituted or replaced by at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups or unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, At least one of Ar1 to Ar4 is an unsubstituted triphenyl. R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 of the unsubstituted or substituted C3-Cs as described below 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 ),and Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following can be represented independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each of the following unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.

2. The compound according to claim 1, wherein: The unsubstituted triphenyl group is represented by formula Y1 or formula Y2: In formulas Y1 and Y2, the asterisk (*) indicates the bonding site with an adjacent atom.

3. The compound according to claim 1, wherein: The unsubstituted triphenyl is represented by one of formulas Y11 to Y25: In formulas Y11 to Y25, the asterisk (*) indicates the bonding site with an adjacent atom.

4. The compound according to claim 1, wherein: The remaining groups in Ar1 to Ar4 that are not the unsubstituted terphenyl groups are each independently unsubstituted or substituted by at least one R group. 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl thiols or unsubstituted or with at least one R 10a Replacement C1-C 60 Mixed aromatic compounds.

5. The compound according to claim 1, wherein: Ar1 or Ar3 is an unsubstituted terphenyl.

6. The compound according to claim 1, wherein: R1 through R4 are each independently -F, -Cl, -Br, -I, cyano, or unsubstituted or modified by at least one R. 10a Replacement C1-C 60 alkyl.

7. The compound according to claim 1, wherein: R 11 and R 15 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 60 Alkyl thioyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C8-C 60 Non-aromatic fused polycyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).

8. The compound according to claim 1, wherein: The compound represented by Formula 1 is selected from one of the following compounds:

9. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as Includes an emission layer and an interlayer between the first electrode and the second electrode. The interlayer comprises a compound represented by Formula 1 according to any one of claims 1 to 8.

10. The light-emitting device according to claim 9, wherein: The first electrode is the anode. The second electrode is a cathode, and The interlayer further includes: a hole transport region between the first electrode and the emitter layer, comprising a hole injection layer, a hole transport layer, an electron blocking layer, an emitter assist layer, or any combination thereof; and / or an electron transport region between the second electrode and the emitter layer, comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

11. The light-emitting device according to claim 10, wherein: The electron transport region includes the compound represented by Formula 1.

12. The light-emitting device according to claim 9, wherein: The interlayer includes an electron transport layer, and the electron transport layer includes the compound represented by Formula 1.

13. The light-emitting device according to claim 9, wherein: The emitter layer includes a first body, a second body, a first dopant, and a second dopant. The first dopant is a compound comprising a metal and a ligand, wherein the ligand comprises an imidazole moiety, and The second dopant is a compound containing boron.

14. The light-emitting device according to claim 13, wherein: The metal includes transition metals.

15. The light-emitting device according to claim 13, wherein: The first entity is a hole transmission entity.

16. The light-emitting device according to claim 13, wherein: The second entity is an electronic transmission entity.

17. The light-emitting device according to claim 9, wherein: The emitting layer emits blue light.

18. An electronic device comprising a light-emitting device according to any one of claims 9 to 18.

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

20. The electronic device according to claim 18, wherein: The electronic devices include displays, light sources, lighting devices, personal computers, mobile phones, digital cameras, electronic notebook computers, electronic notebooks, electronic dictionaries, electronic game devices, medical devices, fish finders, measuring devices, instruments, and / or projectors.

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