Amine compounds and organic light-emitting devices including such amine compounds

Abstract

An amine compound represented by Formula 1 and an organic light-emitting device comprising said amine compound are provided, wherein in Formula 1, R1 to R... 10 One of them is a group represented by Formula 2: When amine compounds are included in organic light-emitting devices as hole transport materials, the devices can exhibit excellent I-V-L characteristics, including low driving voltage, improved efficiency and improved lifetime.

Description

[0001] This application is a divisional application of the invention patent application filed on June 20, 2018, with application number 201810638338.8 and invention title "Amine Compounds and Organic Light-Emitting Devices Including the Amine Compounds". Technical Field

[0002] One or more aspects of this disclosure relate to amine compounds and organic light-emitting devices comprising the amine compounds. Background Technology

[0003] Compared to devices in this field, organic light-emitting devices are self-emitting devices, which have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

[0004] An organic light-emitting device may include a first electrode located on a substrate and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied from the first electrode can move toward the emitter layer through the hole transport region, and electrons supplied from the second electrode can move toward the emitter layer through the electron transport region. Charge carriers (e.g., holes and electrons) can recombine in the emitter layer to generate excitons. The excitons can then transition from an excited state to a ground state, thereby releasing energy in the form of light. Summary of the Invention

[0005] One or more aspects of embodiments of this disclosure provide amine compounds and organic light-emitting devices comprising the amine compounds.

[0006] Other aspects will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practice of the given embodiments.

[0007] One or more aspects of the embodiments of this disclosure provide amine compounds represented by Formula 1:

[0008] Formula 1

[0009]

[0010] Formula 2

[0011]

[0012] In Equations 1 and 2,

[0013] Ar1, Ar2, L1, and L2 can all be independently substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C2-C 60 Heterocyclic group,

[0014] a1 and a2 can both be independent integers from 0 to 5. When a1 is two or greater, two or more L1 values ​​can be the same or different from each other. Similarly, when a2 is two or greater, two or more L2 values ​​can be the same or different from each other.

[0015] When a1 is zero, *-(L1) a1 -*' can be a single bond; when a2 is zero, *-(L2) a2 -*' can be a single key.

[0016] R1 to R 10 Each group can be independently selected from the group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), -S(=O)(Q1)(Q2) and -S(=O)2(Q1)(Q2),

[0017] The prerequisite is R1 to R 10 One of them is a group represented by formula 2.

[0018] R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), -S(=O)(Q1)(Q2) and -S(=O)2(Q1)(Q2),

[0019] b1 and b2 can both be independent integers from 1 to 10, where when b1 is two or greater, two or more R... 11 They can be the same or different from each other, and when b2 is two or greater, two or more R... 12 They can be the same or different from each other.

[0020] Replacement C5-C 60 Carbocyclic group, substituted C2-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group may be selected from:

[0021] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0022] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0023] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;

[0024] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and

[0025] -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0026] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 And Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0027] Both * and *' refer to the bonding site with adjacent atoms.

[0028] On the other hand, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emitting layer and at least one of the amine compounds. Attached Figure Description

[0029] These and / or other aspects will become apparent and more readily understood from the following description of exemplary embodiments taken in conjunction with the accompanying drawings, in which:

[0030] Figure 1 This is a schematic diagram of an organic light-emitting device according to an embodiment of the present disclosure;

[0031] Figure 2 This is a schematic diagram of an organic light-emitting device according to an embodiment of the present disclosure;

[0032] Figure 3 A schematic diagram of an organic light-emitting device according to an embodiment of the present disclosure; and

[0033] Figure 4 This is a schematic diagram of an organic light-emitting device according to an embodiment of the present disclosure. Detailed Implementation

[0034] This disclosure will now be described more fully with reference to exemplary embodiments. The advantages, features, and methods of implementation of the invention will become apparent from the embodiments described in detail herein and the accompanying drawings. However, the invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concept of the disclosure to those skilled in the art.

[0035] In the following description, embodiments will be illustrated in more detail with reference to the accompanying drawings, in which the same reference numerals denote the same elements and may not be described repeatedly.

[0036] As used herein, unless the context clearly indicates otherwise, the singular forms “a,” “a,” and “the” are also intended to include the plural forms.

[0037] It will also be understood that the term “comprising” and / or variations thereof may be used herein to describe the presence of a stated feature or component, but does not preclude the presence or addition of one or more other features or components.

[0038] It will be understood that when a layer, region, or component is referred to as being "on" or "to" another layer, region, or component, the layer, region, or component may be formed directly or indirectly on the other layer, region, or component. That is, for example, intermediate layers, regions, or components may exist. Conversely, when an element is referred to as being "directly" on another element, there are no intermediate elements.

[0039] For ease of explanation, the dimensions and thicknesses of the components in the figures may be exaggerated. In other words, since the dimensions and thicknesses of the components in the figures are arbitrarily shown for ease of explanation, the following embodiments of this disclosure are not limited thereto.

[0040] The amine compounds according to embodiments of this disclosure are represented by the following formula 1:

[0041] Formula 1

[0042]

[0043] Formula 2

[0044]

[0045] Ar1, Ar2, L1, and L2 in Equations 1 and 2 can all be independently substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C2-C 60 Heterocyclic group.

[0046] In one or more embodiments, Ar1, Ar2, L1, and L2 may each be independently substituted or unsubstituted C5-C. 30 Carbocyclic group or substituted or unsubstituted C2-C 30 Heterocyclic group.

[0047] In one or more embodiments, Ar1 and Ar2 may each be independently selected from:

[0048] Phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirofluorenyl, benzo[9,10]phenanthreneyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthreneyl, pyrene, alkyl, tetraphenyl, francyl, perylene, penfenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, carbazole, phenanthridine, acridineyl, phenanthridine, phenazinyl, benzoxazolyl, benzimidazolyl, furanyl, benzofuranyl, thiophene, benzothiophene, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzoxazolyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl and dibenzocarbazolyl; and

[0049] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C2-C 20 heteroaryl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, indaryl, acenaphthyl, fluorenyl, spirofluorenyl, benzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, alkyl, tetraphenyl, francyl, perylene, penfenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthridine, acridineyl, phenanthridine, phenazinyl, benzoxazolyl, benzimidazolyl, furanyl, benzofuranyl, thiophene, benzothiophene, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzoxazolyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, and dibenzocarbazole.

[0050] L1 and L2 can both be independently selected from:

[0051] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirofluorene, benzo[9,10]fluorene, phenenenyl, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, tetraphenyl, purinyl, perylene, pentylenetyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, isoindolyl, indolyl, inzolyl, purinelyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenazolyl, carbazolyl, acridine , phenanthroline, phenazinyl, benzoxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiopheneyl, benzothiopheneyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzoxazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl and dibenzocarbazoleyl; and

[0052] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C2-C 20 heteroaryl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirofluoreneylene, benzo[9,10]fluoreneylene, phenenenylene, phenanthreneylene, anthraceneylene, fluoranthraceneylene, benzo[9,10]phenanthreneylene, pyreneylene, etc. alkyl, tetraphenyl, purinyl, perylene, pentylenetyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, isoindolyl, indolyl, inzolyl, purinelyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, carbazolyl, phenanthridine, acetyl The following groups are listed: pyridyl, phenanthroline, phenazinyl, benzoxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiopheneyl, benzothiopheneyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzoxazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, and dibenzocarbazoleyl.

[0053] Among them, Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, 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, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0054] However, the embodiments disclosed herein are not limited thereto.

[0055] In one or more embodiments, L1 and L2 may each be independently selected from any group represented by formula 3-1 to formula 3-46, but the embodiments of this disclosure are not limited thereto:

[0056]

[0057]

[0058]

[0059] In equations 3-1 to 3-46,

[0060] Y1 can be O, S, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7).

[0061] Z1 to Z7 can all be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spirodifluorenyl, phenanthrenyl, phenanthryl, anthraceneyl, fluoranthrenyl, benzo[9,10]phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, and -Si(Q 31 (Q) 32 (Q) 33 ),

[0062] d2 can be an integer from 0 to 2, where when d2 is two or greater, two or more Z1s can be the same or different from each other.

[0063] d3 can be an integer from 0 to 3, where when d3 is two or greater, two or more Z1s can be the same or different from each other, and two or more Z2s can be the same or different from each other.

[0064] d4 can be an integer from 0 to 4, where when d4 is two or greater, two or more Z1s can be the same or different from each other, and two or more Z2s can be the same or different from each other.

[0065] d5 can be an integer from 0 to 5, where when d5 is two or greater, two or more Z1s can be the same or different from each other, and two or more Z2s can be the same or different from each other.

[0066] d6 can be an integer from 0 to 6, where when d6 is two or greater, two or more Z1s can be the same or different from each other.

[0067] d8 can be an integer from 0 to 8, where when d8 is two or greater, two or more Z1s can be the same or different from each other.

[0068] Both * and *' refer to the bonding site with adjacent atoms.

[0069] In Equation 2, a1 and a2 can both be independent integers from 0 to 5. a1 refers to the number of L1s, where when a1 is two or greater, two or more L1s can be the same or different from each other. a2 refers to the number of L2s, where when a2 is two or greater, two or more L2s can be the same or different from each other.

[0070] When a1 is zero, *-(L1) a1 -*' can be a single bond; when a2 is zero, *-(L2) a2 -*' can be a single key.

[0071] In one or more embodiments, a1 and a2 may each be 0 or 1 independently, but the embodiments of this disclosure are not limited thereto.

[0072] In one or more embodiments, Ar1 and Ar2 may each be independently selected from:

[0073] Phenyl; and

[0074] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C2-C 20 heteroaryl and -Si(Q) 31 (Q) 32 (Q) 33The phenyl group selected from at least one of the following is not limited to this.

[0075] In one or more embodiments, Ar1 and Ar2 may each be independently selected from any group represented by formula 5-1 to formula 5-80, but the embodiments of this disclosure are not limited thereto:

[0076]

[0077]

[0078]

[0079]

[0080] In equations 5-1 to 5-80,

[0081] Y 31 It can be O, S, C(Z) 33 (Z) 34 ), N(Z 35 ) or Si(Z 36 (Z) 37 ),

[0082] Z 31 To Z 37 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spirodifluorenyl, spirofluorenyl-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenatenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[9,10]phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphthidyl, quinoxalinyl, quinazolinyl, carbazoleyl, phenanthrynyl, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl and -Si(Q 31 (Q) 32 (Q) 33 ),

[0083] e2 can be an integer from 0 to 2, where when e2 is two or greater, it represents two or more Z. 31 They can be the same or different from each other and there can be two or more Zs. 32 They can be the same or different from each other.

[0084] e3 can be an integer from 0 to 3, where when e3 is two or greater, it represents two or more Z. 31They can be the same or different from each other and there can be two or more Zs. 32 They can be the same or different from each other.

[0085] e4 can be an integer from 0 to 4, where when e4 is two or greater, it represents two or more Z. 31 They can be the same or different from each other and there can be two or more Zs. 32 They can be the same or different from each other.

[0086] e5 can be an integer from 0 to 5, where when e5 is two or greater, it represents two or more Z. 31 They can be the same or different from each other and there can be two or more Zs. 32 They can be the same or different from each other.

[0087] e6 can be an integer from 0 to 6, where when e6 is two or greater, it represents two or more Z. 31 They can be the same or different from each other and there can be two or more Zs. 32 They can be the same or different from each other.

[0088] e7 can be an integer from 0 to 7, where when e7 is two or greater, it represents two or more Z. 31 They can be the same or different from each other.

[0089] e9 can be an integer from 0 to 9, where when e9 is two or greater, it represents two or more Z. 31 They can be the same or different from each other.

[0090] * indicates the bonding site with an adjacent atom.

[0091] In Equation 1, R1 to R 10 Each group can be independently selected from the group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), -S(=O)(Q1)(Q2) and -S(=O)2(Q1)(Q2),

[0092] The prerequisite is from R1 to R 10 One of the selected groups is the group represented by Formula 2.

[0093] R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -P(=O)(Q1)(Q2), -P(=S)(Q1)(Q2), -S(=O)(Q1)(Q2) and -S(=O)2(Q1)(Q2),

[0094] Among them, Q1 to Q3 can each be independently combined with Q here. 31 To Q 33 The description is the same.

[0095] In one or more embodiments, R1 to R 10 Each group can be independently selected from the group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60Alkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, and -Si(Q1)(Q2)(Q3),

[0096] R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 The compounds may be heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and -Si(Q1)(Q2)(Q3), but the embodiments of this disclosure are not limited thereto.

[0097] In one or more embodiments, R1 to R 10 Each group can be independently selected from the group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl groups, any one of formulas 5-1 to 5-80, and -Si(Q1)(Q2)(Q3),

[0098] R 11 and R 12 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl groups, any group represented by formulas 5-1 to 5-80, and -Si(Q1)(Q2)(Q3), but the embodiments of this disclosure are not limited thereto.

[0099] In one or more embodiments, R 11 and R 12 Each group can be independently selected from any one of the groups represented by formulas 6-1 to 6-34, but the embodiments of this disclosure are not limited thereto:

[0100]

[0101]

[0102] In equations 6-1 to 6-34,

[0103] Ph refers to phenyl.

[0104] * indicates the bonding site with an adjacent atom.

[0105] In Equation 2, b1 and b2 can both be independent integers from 1 to 10. b1 refers to R. 11 The number of R, where when b1 is two or greater, two or more R 11 They can be the same or different from each other. b2 refers to R. 12 The number of R, where when b1 is two or greater, two or more R 12 They can be the same as or different from each other.

[0106] In one or more embodiments, the amine compound represented by Formula 1 may be represented by one selected from Formulas 1-1 to 1-6, but the embodiments of this disclosure are not limited thereto:

[0107] Formula 1-1

[0108]

[0109] Formula 1-2

[0110]

[0111] Formula 1-3

[0112]

[0113] Formula 1-4

[0114]

[0115] Formula 1-5

[0116]

[0117] Formula 1-6

[0118]

[0119] Ar1, Ar2, L1, L2, a1, a2, R1 to R in Equations 1-1 to 1-6 12 b1 and b2 can all be the same as those described by combining equations 1 and 2.

[0120] In one or more embodiments, R1 to R in Formulas 1-1 to 1-6 10 The components can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, phenyl, and biphenyl, but the embodiments disclosed herein are not limited thereto.

[0121] In one or more embodiments,

[0122] i) When the amine compound represented by Formula 1 is represented by Formula 1-1, R2 to R 10 Both can be hydrogen;

[0123] ii) When the amine compound represented by Formula 1 is represented by Formula 1-2, R8 and R9 can each be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, phenyl and biphenyl, R1, R3 to R7 and R 10 Both can be hydrogen;

[0124] iii) When the amine compound represented by Formula 1 is represented by Formulas 1-3, R1, R2, and R4 to R 10 Both can be hydrogen;

[0125] iv) When the amine compound represented by Formula 1 is represented by Formulas 1-4, R1 to R3 and R5 to R 10 Both can be hydrogen;

[0126] v) When the amine compound represented by Formula 1 is represented by Formulas 1-5, R1 to R7 and R9 to R 10 Both can be hydrogen; or

[0127] vi) When the amine compound represented by Formula 1 is represented by Formulas 1-6, R2 may be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, phenyl and biphenyl, R1, R3 to R8 and R 10 All of them can be hydrogen, but the embodiments disclosed herein are not limited thereto.

[0128] In one or more embodiments, Ar1 and Ar2 in Formulas 1-1 to 1-6 may each be independently selected from:

[0129] Phenyl; and

[0130] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C2-C 20 heteroaryl and -Si(Q) 31 (Q) 32 (Q) 33 The phenyl group selected from at least one of the following is not limited to this.

[0131] In one or more embodiments, R in Formulas 1-1 to 1-6 11 and R 12 The groups can be independently selected from any one of the groups represented by formulas 5-1 to 5-80, but the embodiments of this disclosure are not limited thereto.

[0132] In one or more embodiments, R in Formulas 1-1 to 1-6 11 and R 12 Each group can be independently selected from any one of the groups represented by formulas 6-1 to 6-34, but the embodiments of this disclosure are not limited thereto.

[0133] In one or more embodiments, in formulas 1-1 to 1-6,

[0134] R 11 and R 12 Each group can be independently selected from any one of the groups represented by formulas 6-1 to 6-34.

[0135] Ar1 and Ar2 can both be independently selected from:

[0136] Phenyl; and

[0137] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C2-C 20 heteroaryl and -Si(Q) 31 (Q) 32 (Q) 33 The phenyl group selected from at least one of the following is not limited to this.

[0138] In one or more embodiments, the substituted C5-C 60 Carbocyclic group, substituted C2-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60Arylthioyl, substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group may be selected from:

[0139] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0140] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0141] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;

[0142] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and

[0143] -Si(Q 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0144] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 And Q 31 To Q33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, 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, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0145] * indicates the bonding site with an adjacent atom.

[0146] In one or more embodiments, the amine compound represented by Formula 1 may be selected from any one of compound 1 to compound 144, but the embodiments of this disclosure are not limited thereto:

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] When an amine compound represented by Formula 1 satisfies a structure such that hole hopping can be facilitated through orbital delocalization, wherein benzene is further condensed at a specific position of fluorene, and a substituent with a cyclic structure is included at a specific position of fluorene (e.g., a fluorene group is substituted with a cyclic group at the C9 position, and the benzene ring of the fluorene group is further condensed with a phenyl group). Therefore, this amine compound can exhibit high charge mobility, and thus, organic light-emitting devices comprising this amine compound can be driven with low power.

[0160] Furthermore, compared to compounds comprising two or more amino groups (e.g., diamines, triamines, etc.), when an amine compound includes only one amino group within its molecule (e.g., a monoamine compound), it can possess a relatively low highest occupied molecular orbital (HOMO) energy level. Thus, the amine compound (e.g., a monoamine compound) can have energy levels optimized for hole transport. Consequently, electronic devices incorporating this amine compound (e.g., organic light-emitting devices) can exhibit low driving voltage, high efficiency, and long lifetime.

[0161] The synthetic method for preparing amine compounds represented by Formula 1 should be apparent to those skilled in the art by referring to the examples below.

[0162] At least one of the amine compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device (e.g., in a layer disposed between a cathode and an anode). For example, the amine compound can be included in at least one selected from a hole transport region, an electron transport region, and an emission layer. In one or more embodiments, the amine compound of Formula 1 can be used as a material for a capping layer located outside the pair of electrodes of the organic light-emitting device (e.g., in a layer not located between an anode and a cathode).

[0163] Therefore, embodiments of this disclosure provide an organic light-emitting device, the organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode, the organic layer comprising an emitting layer, wherein the organic layer comprises at least one amine compound (e.g., an amine compound represented by Formula 1).

[0164] As used herein, the term "(organic layer) comprises at least one amine compound" may refer to the case where the (organic layer) comprises the same amine compound represented by Formula 1, or it may refer to the case where the (organic layer) comprises two or more different amine compounds represented by Formula 1.

[0165] In one or more embodiments, for example, the organic layer may comprise only compound 1 as an amine compound. In this respect, compound 1 may be present (e.g., included) in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may comprise both compound 1 and compound 2 as amine compounds (e.g., a mixture of compound 1 and compound 2). In this respect, compound 1 and compound 2 may be present in the same layer (e.g., the same layer) (e.g., both compound 1 and compound 2 may be present in the emitting layer), or they may be present in different layers (e.g., compound 1 may be present in the emitting layer, and compound 2 may be present in the electron transport layer).

[0166] In one or more embodiments, the first electrode can be an anode, the second electrode can be a cathode, and the organic layer can further include a hole transport region and an electron transport region. The hole transport region is located between the first electrode and the emitter layer, and the electron transport region is located between the emitter layer and the second electrode. The hole transport region can include a hole injection layer, a hole transport layer, an emitter assist layer, an electron blocking layer, or any combination thereof, and the electron transport region can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0167] In one or more embodiments, the hole transport region may include an amine compound (e.g., an amine compound represented by Formula 1).

[0168] In one or more embodiments, the hole transport region may include a hole transport layer, which includes an amine compound (e.g., an amine compound represented by Formula 1).

[0169] In one or more embodiments, the emission layer may include an amine compound represented by Formula 1.

[0170] In one or more embodiments, the hole transport region may include a p-doped agent, which may have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less.

[0171] In one or more embodiments, the emitter layer may include at least one selected from styrene compounds, anthracene compounds, pyrene compounds, and spirodifluorene compounds.

[0172] In one or more embodiments, the emitting layer may be a first color light emitting layer.

[0173] Organic light-emitting devices may further include, between the first electrode and the second electrode: i) at least one second color light-emitting layer or ii) at least one second color light-emitting layer and at least one third color light-emitting layer.

[0174] The maximum emission wavelengths of the first color light, the second color light, and the third color light can be the same or different from each other.

[0175] The first color light and the second color light can be emitted in the form of a mixed light, or the first color light, the second color light and the third color light can be emitted in the form of a mixed light.

[0176] As used herein, the term "organic layer" can refer to a single layer and / or multiple layers disposed between the first electrode and the second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0177] Figure 1 This is a schematic diagram of an organic light-emitting device 10 according to an embodiment of the present disclosure. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0178] In the following text, we will combine Figure 1 The structure of an organic light-emitting device 10 according to embodiments of the present disclosure and a method for manufacturing the organic light-emitting device 10 are described.

[0179] exist Figure 1 In this configuration, the substrate may be additionally disposed below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which possess excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0180] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material used to form the first electrode 110 can be selected from materials with high work function to facilitate hole injection.

[0181] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. When the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can 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. However, the material used to form the first electrode 110 is not limited thereto.

[0182] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.

[0183] An organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emitter layer.

[0184] The organic layer 150 may also include a hole transport region and an electron transport region, with the hole transport region located between the first electrode 110 and the emitter layer, and the electron transport region located between the emitter layer and the second electrode 190.

[0185] The hole transport region may have: i) a single-layer structure comprising a single layer containing a single material; ii) a single-layer structure comprising a single layer containing multiple different materials; or iii) a multi-layer structure comprising multiple layers containing multiple different materials.

[0186] The hole transport region may include at least one layer selected from the hole injection layer (HIL), hole transport layer (HTL), emission assist layer, and electron blocking layer (EBL).

[0187] For example, the hole transport region can have: a single-layer structure comprising a single layer containing multiple different materials, or a multi-layer structure having 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 the constituent layers of each structure are sequentially stacked from the first electrode 110 in the order stated therein. However, the structure of the hole transport region is not limited to this.

[0188] The hole transport region may include amine compounds represented by Formula 1.

[0189] In addition to the amine compounds represented by Formula 1, the hole transport region may also include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by Formula 201, and compounds represented by Formula 202:

[0190]

[0191] In equations 201 and 202,

[0192] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0193] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0194] xa1 to xa4 can each be an integer selected independently from 0 to 3.

[0195] xa5 can be an integer selected from 1 to 10.

[0196] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.

[0197] In one or more embodiments, in formula 202, R 201 and R 202 R can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond. 203 and R 204 It can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond.

[0198] In one or more embodiments, in formulas 201 and 202,

[0199] L 201 To L 205 Each can be independently selected from:

[0200] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenyl, anthracene, fluorenyl, benzo[9,10]phenenyl, pyrene, phenylene alkyl, benzotetraphenyl, purylene, perylene, pentaphenylene, benzohexaphenylene, benzopentaphenylene, benzobenzyl, benzoylene, oleophylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzothiopheneyl, and pyridylene; and

[0201] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirodifluoreneylene, benzo[9,10]fluoreneylene, dibenzo[9,10]fluoreneylene, phenanthroline, anthraceneylene, fluoranthroline, benzo[9,10]phenanthroline, pyreneylene, etc. alkyl, tetraphenyl, arbutinyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, rubidinyl, benzoyl, oleophyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridylyl.

[0202] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0203] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.

[0204] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0205] In one or more embodiments, R 201 To R 204 and Q 201 Each can be independently selected from:

[0206] Phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and

[0207] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.

[0208] Among them, Q 31 To Q 33 Same as described above.

[0209] In one or more embodiments, R in Formula 201 201 To R 203 At least one of them can be selected from:

[0210] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and

[0211] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The alkyl group of phenyl, the phenyl group substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl are selected from at least one of the following: fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl.

[0212] However, the embodiments disclosed herein are not limited thereto.

[0213] In one or more embodiments, in formula 202, i)R 201 and R 202 It can be connected via a single key, and / or ii)R 203 and R 204 It can be connected via a single key.

[0214] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:

[0215] Carbazolyl; and

[0216] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The carbazoyl group selected from at least one of the following: alkyl phenyl, phenyl substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.

[0217] However, the embodiments disclosed herein are not limited thereto.

[0218] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0219] Formula 201A

[0220]

[0221] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0222] Formula 201A(1)

[0223]

[0224] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0225] Formula 201A-1

[0226]

[0227] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A:

[0228] Formula 202A

[0229]

[0230] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A-1:

[0231] Formula 202A-1

[0232]

[0233] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,

[0234] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 All can be the same as described above.

[0235] This can be referenced here in conjunction with R. 203 The provided description helps to understand R. 211 and R 212 ,

[0236] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, furanyl, perylene, pentyranyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.

[0237] The hole transport region may include at least one compound selected from compound HT1 to compound HT39, but embodiments of this disclosure are not limited thereto:

[0238]

[0239]

[0240]

[0241]

[0242] The hole transport region can have approximately up to approximately (for example, approximately) up to approximately The thickness of the hole injection layer is approximately [missing information]. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer may have approximately [missing information]. up to approximately (for example, approximately) up to approximately The hole transport layer can have a thickness of approximately [missing information - likely a number]. up to approximately (for example, approximately) up to approximately The thickness of the hole transport region, hole injection layer, and hole transport layer is within these ranges. When the thicknesses of these three layers are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0243] The emission assist layer can improve the luminous efficiency of the device by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer (e.g., by adjusting the optical resonant distance to match the wavelength of the light emitted from the emission layer), and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. Both the emission assist layer and the electron blocking layer can comprise the materials described above.

[0244] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.

[0245] The charge-generating material can be, for example, a p-doped agent.

[0246] In one or more embodiments, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less.

[0247] p-dopers may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments disclosed herein are not limited thereto.

[0248] In one or more embodiments, for example, the p-doper may include at least one selected from the following:

[0249] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);

[0250] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0251] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0252] The compound represented by formula 221,

[0253] However, the embodiments disclosed herein are not limited thereto:

[0254]

[0255] Equation 221

[0256]

[0257] In Equation 221,

[0258] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, wherein, from R221 To R 223 At least one of the selected groups may include cyano, -F, -Cl, -Br, -I, or C1-C substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and substituted C1-C groups with -I 20 At least one substituent selected from alkyl groups.

[0259] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer according to the sub-pixels. In one or more embodiments, 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 may be in contact with each other or may be separated from each other. 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.

[0260] The emitting layer may include a host and a dopant. The dopant may include at least one selected from phosphorescent dopant and fluorescent dopant.

[0261] Based on 100 parts by weight of the body, the dopant may be included in the emitter layer in an amount of about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0262] The emission layer can have approximately up to approximately (for example, approximately) up to approximately The thickness of the emitter layer is within this range. When the thickness of the emitter layer is within this range, excellent emission characteristics can be obtained without significantly increasing the driving voltage.

[0263] In one or more embodiments, the body may include a compound represented by formula 301:

[0264] Formula 301

[0265] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0266] In Equation 301,

[0267] Ar 301 C5-C can be substituted or unsubstituted.60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0268] xb11 can be 1, 2, or 3.

[0269] L 301 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0270] xb1 can be an integer from 0 to 5.

[0271] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed 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) and -P(=O)(Q 301 (Q) 302 ),

[0272] xb21 can be an integer from 1 to 5.

[0273] Among them, Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0274] In one or more embodiments, Ar in Formula 301 301 It can be selected from:

[0275] Naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, penfenyl, indanethenyl, dibenzofuranyl and dibenzothiophenyl;

[0276] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyreneyl, alkyl, tetraphenyl, francyl, perylene, penfenyl, indanethenyl, dibenzofuranyl, and dibenzothiophenyl,

[0277] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. However, the embodiments disclosed herein are not limited thereto.

[0278] When xb11 in equation 301 is two or greater, two or more Ar 301 It can be connected via a single key.

[0279] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0280] Formula 301-1

[0281]

[0282] Formula 301-2

[0283]

[0284] In Equations 301-1 and 301-2,

[0285] A 301 To A 304 Each of these can be independently selected from phenyl, naphthyl, phenanthryl, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyridyl, pyrimidinyl, indole, fluorenyl, spirodifluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], indolyl, carbazoleyl, benzo[carbazoleyl], dibenzo[carbazoleyl], furanyl, benzo[furanyl], dibenzo[furanyl], naphtho[furanyl], benzo[naphtho[furanyl], dinaphtho[furanyl], thiopheneyl, benzo[thiopheneyl], dibenzo[thiopheneyl], naphtho[thiopheneyl], benzo[naphtho[thiopheneyl], and dinaphtho[thiopheneyl]

[0286] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0287] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32),

[0288] xb22 and xb23 can each be independently 0, 1, or 2.

[0289] L 301 xb1, R 301 and Q 31 To Q 33 All can be the same as described above.

[0290] L 302 To L 304 They can all independently bind with L 301 The descriptions are the same.

[0291] xb2 to xb4 can all be independently identical to those described in conjunction with xb1.

[0292] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.

[0293] For example, in Equations 301, 301-1, and 301-2, L 301 To L 304 Each can be independently selected from:

[0294] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0295] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,

[0296] Among them, Q 31 To Q 33 Same as described above.

[0297] In one or more embodiments, in formulas 301, 301-1, and 301-2, R 301 To R 304 Each can be independently selected from:

[0298] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0299] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31-S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.

[0300] Among them, Q 31 To Q 33 It can be the same as described above.

[0301] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55) and Mg complexes. In some embodiments, the host may include a Zn complex.

[0302] In one or more embodiments, the body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0303]

[0304]

[0305]

[0306] Phosphorescent dopants may include organometallic complexes represented by the following formula 401:

[0307] Formula 401

[0308] M(L 401 ) xc1 (L 402 ) xc2 ,

[0309] Formula 402

[0310]

[0311] In Equations 401 and 402,

[0312] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).

[0313] L 401 The ligands can be selected from those represented by formula 402, where xc1 can be 1, 2, or 3, and when xc1 is two or more, two or more L... 401 They can be the same or different from each other.

[0314] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 is two or greater, two or more L... 402 They can be the same or different from each other.

[0315] X 401 To X 404 They can each be nitrogen (N) or carbon (C) independently.

[0316] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.

[0317] A 401 and A 402 Each can be independently selected from C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group,

[0318] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *', where Q411 and Q 412 It can be hydrogen, deuterium, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0319] X 406 It can be a single bond, O, or S.

[0320] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed 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 ) and -P(=O)(Q 401 (Q) 402 ), where Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0321] xc11 and xc12 can each be an integer selected independently from 0 to 10.

[0322] In Equation 402, * and *' both refer to the binding position with M in Equation 401.

[0323] In one or more embodiments, A in Formula 402 401 and A 402 They can all be independently selected from phenyl, naphthyl, fluorenyl, spirodifluorenyl, indyl, pyrroleyl, thiopheneyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, carbazoleyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, isobenzothiopheneyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiopheneyl.

[0324] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, X 402 It can be carbon, or ii)X 401 and X 402 Both can be nitrogen.

[0325] In one or more embodiments, in formula 402, R 401 and R 402 Each can be independently selected from:

[0326] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0327] All are substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl. 20 Alkyl and C1-C 20 Alkoxy;

[0328] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0329] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and

[0330] -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ),

[0331] Among them, Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.

[0332] In one or more embodiments, when xc1 in equation 401 is two or greater, two or more L 401 The two A's in 401 It can be optionally via X as a linking group 407 To connect, or two or more L 401 The two A's in 402 It can be optionally via X as a linking group 408 To connect (see compounds PD1 through PD4 and compound PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but not limited to these.

[0333] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The components may be selected from halogens, diketones (e.g., acetylacetone), carboxylic acids (e.g., pyridine carboxylates), -C (=O), isonitriles, -CN, and phosphorus (e.g., phosphine and phosphites), but the embodiments disclosed herein are not limited thereto.

[0334] In one or more embodiments, the phosphorescent dopant may be selected from, for example, any one of compounds PD1 to PD25, but the embodiments disclosed herein are not limited thereto:

[0335]

[0336]

[0337] Fluorescent dopants may include arylamine compounds or styreneamine compounds.

[0338] Fluorescent dopants may include compounds represented by Formula 501:

[0339] Formula 501

[0340]

[0341] In Equation 501,

[0342] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0343] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.

[0344] xd1 to xd3 can each be an independent integer from 0 to 3;

[0345] R 501 and R 502 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.

[0346] xd4 can be an integer from 1 to 6.

[0347] In one or more embodiments, Ar in Formula 501 501 It can be selected from:

[0348] Naphthyl, heptalenyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthyl, pyrene, alkyl, tetraphenyl, francyl, perylene, penfenyl, indoxanel, and indoxphenanthryl; and

[0349] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 At least one of alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, naphthyl, heptalenyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[1]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, It includes alkyl, tetraphenyl, styrene, peryl, penfenyl, indanethenyl, and indanephenyl.

[0350] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:

[0351] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, and pyridylene; and

[0352] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, The following are selected from at least one of the following groups: phenylene, perylene, pentofenyl, nehexaphenyl, nepentylphenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl; phenylene, naphthylene, fluoreneylene, spirodifluoreneyl, benzo[9,10]fluoreneyl, dibenzo[9,10]fluoreneyl, phenanthreneyl, anthraceneylene, fluorenyleneyl, benzo[9,10]phenanthreneyl, pyreneyleneyl, etc. The compounds are: alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzothiopheneyl, dibenzothiopheneyl, and pyridylene.

[0353] In one or more embodiments, in formula 501, R 501 and R 502 Each can be independently selected from:

[0354] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and

[0355] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, The following groups are listed: alkyl, peryl, pentyranyl, benzohexaphenyl, benzopentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.

[0356] Among them, Q 31 To Q 33 All can be selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0357] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.

[0358] In one or more embodiments, for example, the fluorescent dopant may be selected from any one of compounds FD1 to FD22:

[0359]

[0360]

[0361]

[0362] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments disclosed herein are not limited thereto:

[0363]

[0364] The electron transport region may have: i) a single-layer structure comprising a single layer containing a single material; ii) a single-layer structure comprising a single layer containing multiple different materials; or iii) a multi-layer structure comprising multiple layers containing multiple different materials.

[0365] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of this disclosure are not limited thereto.

[0366] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the emitter layer in the order they are stated. However, embodiments of the electron transport region structure are not limited to these.

[0367] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring.

[0368] As used herein, the term "π-electron-poor nitrogen-containing ring" may refer to a C1-C ring having at least one *-N=*' moiety as a cyclic part. 60 Heterocyclic group.

[0369] For example, a "nitrogen-containing ring depleted of π electrons" can be i) a 5- to 7-membered heterocyclic monocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group formed by the condensation of two or more 5- to 7-membered heterocyclic monocyclic groups, each having at least one *-N=*' moiety; or iii) at least one of a 5- to 7-membered heterocyclic monocyclic group, each having at least one *-N=*' moiety, and at least one C5-C 60 Heterocyclic groups formed by the condensation of carbocyclic groups.

[0370] Non-limiting examples of π-electron-depleted nitrogen-containing rings may include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazoline, cyclophosphine, phenanthridine, acridine, phenanthridine, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0371] In one or more embodiments, for example, the electron transport region may include a compound represented by Formula 601:

[0372] Formula 601

[0373] [Ar 601 ] xe11 -[(L601 ) xe1 -R 601 ] xe21 .

[0374] In Equation 601,

[0375] Ar 601 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0376] xe11 can be 1, 2, or 3.

[0377] L 601 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups;

[0378] xe1 can be an integer from 0 to 5.

[0379] R 601 It can be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0380] Among them, Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0381] xe21 can be an integer from 1 to 5.

[0382] In one or more embodiments, xe11 numbers of Ar 601 At least one and / or xe21 numbers of R 601 At least one of them may include a nitrogen-containing ring that is π-electron depleted.

[0383] In one or more embodiments, the ring Ar in Formula 601 601 It can be selected from:

[0384] Phenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, alkyl, tetraphenyl, francyl, perylene, penfenyl, indoxanthyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, imidazoyl, pyrazolyl, thiazoyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazoyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidine and azacarbazoyl; and

[0385] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyreneyl, The following groups are listed: alkyl, tetraphenyl, francyl, perylene, penfenyl, indoxanthracene, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, imidazoyl, pyrazolyl, thiazoyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazoyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazoyl.

[0386] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0387] When xe11 in equation 601 is two or greater, two or more Ar 601 It can be connected via a single key.

[0388] In one or more embodiments, Ar in Formula 601 601 It can be anthracene-based.

[0389] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:

[0390] Formula 601-1

[0391]

[0392] In Equation 601-1,

[0393] 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 ), from X 614 To X 616 At least one of the selected options can be N.

[0394] L 611 To L 613 They can all independently bind with L 601 The descriptions are the same.

[0395] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.

[0396] R 611To R 613 They can all independently bind with R 601 The descriptions are the same.

[0397] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0398] In one or more embodiments, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each can be independently selected from:

[0399] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0400] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazine The following are at least one of the following groups selected from: phenylene, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, phenanthrinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrynyl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthrynyl, pyreneylyl, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrazinyl Pyrimidinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rholineyl, phenazinyl, benzoimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and zazacarbazolyl, but the embodiments disclosed herein are not limited thereto.

[0401] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be independently 0, 1 or 2.

[0402] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each can be independently selected from:

[0403] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0404] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalyl The phenyl, biphenyl, terphenyl, naphthinyl, quinoxalinyl, quinazolinyl, terazolinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0405] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0406] Among them, Q 601 and Q 602 It can be the same as described above.

[0407] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0408]

[0409]

[0410]

[0411]

[0412] In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:

[0413]

[0414] The buffer layer, hole blocking layer, and / or electronic control layer can each independently have approximately up to approximately (for example, approximately) up to approximately The thickness of the buffer layer, hole blocking layer, and electron control layer is within these ranges. When the thicknesses of the buffer layer, hole blocking layer, and electron control layer are within these ranges, the electron blocking layer can have excellent electron blocking or electron control characteristics without significantly increasing the driving voltage.

[0415] The electron transport layer can have approximately up to approximately (for example, approximately) up to approximately The thickness of the electron transport layer is within these ranges. When the thickness of the electron transport layer is within these ranges, the electron transport layer can have satisfactory electron transport characteristics without significantly increasing the driving voltage.

[0416] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include a material containing metal.

[0417] Materials containing metals may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions, while alkaline earth metal complexes may include metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. Alkali metal complexes may include ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex, said ligands being selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of this disclosure are not limited thereto.

[0418] For example, materials containing metals can include Li complexes. Li complexes can include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:

[0419]

[0420] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0421] The electron injection layer can have: i) a single-layer structure comprising a single layer containing a single material; ii) a single-layer structure comprising a single layer containing multiple different materials; or iii) a multi-layer structure comprising multiple layers containing multiple different materials.

[0422] 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.

[0423] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one or more embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0424] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0425] The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

[0426] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal.

[0427] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In one or more embodiments, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0428] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-x O(0 < x < 1). In one or more embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0429] The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In one or more embodiments, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0430] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may each include alkali metal ions, alkaline earth metal ions, and rare earth metal ions as described above. The ligands coordinating with the metal ions in the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0431] The electron injection layer may include 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 as described above (e.g., it may consist of 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 as described above). In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer further includes organic materials, the 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 combinations thereof may be uniformly or non-uniformly dispersed in a matrix comprising organic materials.

[0432] The thickness of the electron injection layer can be approximately up to approximately (for example, approximately) up to approximately The thickness of the electron injection layer. When the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing the driving voltage.

[0433] The second electrode 190 may be disposed on the organic layer 150 having the structure described above. The second electrode 190 may serve as a cathode as an electron injection electrode. In this respect, the material used to form the second electrode 190 may be a material with a low work function, and such a material may include metals, alloys, conductive compounds, or combinations thereof.

[0434] In one or more embodiments, the second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0435] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0436] like Figure 2 The organic light-emitting device 20 shown includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, stacked sequentially in the order stated herein. Figure 3 The organic light-emitting device 30 shown includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, stacked sequentially in the order stated herein. Figure 4 The organic light-emitting device 40 shown includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially in the order stated herein.

[0437] exist Figures 2 to 4 In China, this can be achieved through reference and combination. Figure 1 The given description is used to understand the first electrode 110, the organic layer 150, and the second electrode 190.

[0438] In each of the organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210. In each of the organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass outward through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220.

[0439] The first capping layer 210 and the second capping layer 220 can improve the external light emission efficiency of the device based on the principle of constructive interference.

[0440] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer containing organic materials, an inorganic capping layer containing inorganic materials, or a composite capping layer containing both organic and inorganic materials.

[0441] At least one of the first capping layer 210 and the second capping layer 220 may include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents comprising at least one element selected from O, N, S, selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), and iodine (I). In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may include an amine compound.

[0442] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may include a compound represented by formula 201 or a compound represented by formula 202.

[0443] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of this disclosure are not limited thereto:

[0444]

[0445] Already combined Figures 1 to 4 Organic light-emitting devices according to embodiments of the present disclosure are described. However, the embodiments of the present disclosure are not limited thereto.

[0446] Layers constituting hole transport regions, emission layers, and electron transport regions can be formed in a set or predetermined area (e.g., location) using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0447] When layers constituting hole transport regions, emitter regions, and electron transport regions are formed by vacuum deposition, for example, depending on the materials to be included in each layer and the expected structure of each layer, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree of Tor and approximately / second to approximately Vacuum deposition was performed at a deposition rate of / second.

[0448] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at coating speeds of approximately 2,000 rpm to approximately 5,000 rpm and heat treatment temperatures of approximately 80°C to approximately 200°C, depending on the materials to be included in each layer and the expected structure of each layer.

[0449] As used here, the term "C1-C" 60 "alkyl" refers to a monovalent group of a straight-chain or branched saturated aliphatic hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples may include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C..." 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Alkyl groups have essentially the same structure as divalent groups.

[0450] As used here, the term "C2-C" 60 "Alkenyl" refers to a group formed by the synthesis of alkenyl groups through the carbon atoms in the carbon atoms of the 2- 60 A hydrocarbon group formed by replacing at least one carbon-carbon double bond at the middle or end of an alkyl group, non-limiting examples of which may include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in conjunction with this. 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Alkenyl groups are essentially divalent groups with the same structure.

[0451] As used here, the term "C2-C" 60 "Alkyne group" refers to the group formed by the combination of C2-C... 60 A hydrocarbon group formed by replacing at least one carbon-carbon triple bond at the middle or end of an alkyl group; non-limiting examples may include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to a group with a C2-C group. 60 The structure of the alkynyl group is basically the same as that of a divalent group.

[0452] As used here, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 The monovalent group represented by alkyl can include, for example, methoxy, ethoxy, and isopropoxy.

[0453] As used here, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Cycloalkyl groups are essentially divalent groups with the same structure.

[0454] As used here, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms. Non-limiting examples may include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Heterocyclic alkyl groups have essentially the same structure as divalent groups.

[0455] As used here, the term "C3-C" 10"Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic; non-limiting examples may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylidene alkenyl" refers to a group that has a similar structure to C3-C4. 10 Cycloalkenyl groups are essentially divalent groups with the same structure.

[0456] As used here, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups may include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.

[0457] As used here, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, such as the term "C6-C" used herein. 60 "Aryl" refers to a divalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups may include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When all aryl groups consist of two or more rings, the rings can fused together.

[0458] As used here, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-aryl" refers to a divalent group having a heterocyclic aromatic system, wherein the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl and C1-C 60When each heteroaryl group comprises two or more rings, the rings can fused together.

[0459] As used here, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), as used herein in the term "C6-C 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).

[0460] As used herein, the term "monovalent nonaromatic condensation polycyclic group" refers to a monovalent group having two or more rings condensed together, with only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, and lacking aromaticity throughout the molecular structure. A non-limiting example of a monovalent nonaromatic condensation polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic condensation polycyclic group" refers to a divalent group having a structure substantially identical to that of a monovalent nonaromatic condensation polycyclic group.

[0461] As used herein, the term "monovalent non-aromatic condensed heterocyclic group" refers to a monovalent group having two or more rings condensed together, having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and not being aromatic throughout the molecular structure. A non-limiting example of a monovalent non-aromatic condensed heterocyclic group is the carbazoyl group. As used herein, the term "divalent non-aromatic condensed heterocyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heterocyclic group.

[0462] As used here, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, where the cyclic atom is only a carbon atom. (C5-C) 60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. (C5-C) 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the connection to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon cyclic group can be a trivalent group or a tetravalent group.

[0463] As used here, the term "C1-C" 60"Heterocyclic group" refers to a group that, in addition to using at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom (excluding carbon (the number of carbon atoms can range from 1 to 60)), has a cyclic relationship with C1-C2. 60 Carbon cyclic groups are groups with essentially the same structure as those with carbon ring groups.

[0464] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group may be selected from:

[0465] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0466] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0467] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;

[0468] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q)21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and

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

[0470] Among them, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, 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, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.

[0471] For example, the term "Ph" as used here may refer to phenyl; the term "Me" as used here may refer to methyl; the term "Et" as used here may refer to ethyl; the term "ter-Bu" or "Bu" as used here may refer to ethyl. t "Can refer to tert-butyl; as the term "OMe" used here can refer to methyl methacrylate (MMA).

[0472] As used here, the term "biphenyl" refers to a "phenyl group that has a substituted phenyl group." In other words, "biphenyl" is a substituted phenyl group that has a phenyl group as a substituent.

[0473] The term "terphenyl" as used here refers to "a phenyl group substituted with a biphenyl group." In other words, "terphenyl" is a phenyl group having a phenyl group substituted with a biphenyl group as a substituent.

[0474] Unless otherwise defined, the * and *' used here refer to the binding sites with adjacent atoms in the corresponding equation.

[0475] In the following, compounds according to embodiments of the present disclosure and organic light-emitting devices according to embodiments of the present disclosure will be described in more detail with reference to synthesis examples and examples. The phrase "using B instead of A" as used in the description of the synthesis examples means using the same molar equivalent of B instead of A.

[0476] [Synthesis Example]

[0477] Synthesis Example 1: Synthesis of Compound 2

[0478]

[0479] (1) Synthesis of intermediate products 2-3

[0480] 10 g of methyl 5-bromo-2-iodobenzoate (2-1) and 5 g of naphthalene-1-boronic acid (2-2) were dissolved in 100 mL of tetrahydrofuran (THF) and 25 mL of water, and 1 g of Pd(PPh3)4 and 12 g of K2CO3 were added dropwise. The reaction solution was refluxed and stirred at 65 °C for 6 hours. After cooling the reaction solution to room temperature, THF was removed under reduced pressure, and the mixture was extracted three times with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and filtered under reduced pressure. The residue obtained was purified by column chromatography to give 8.3 g of intermediate 2-3 (yield: 83%).

[0481] C 18 H 13 BrO2 M+1: 341.01.

[0482] (2) Synthesis of intermediate product 2-4

[0483] 8.3 g of intermediate 2-3 was dissolved in 120 mL of THF, and 60 mL of PhMgBr (1 M) was slowly added dropwise at 0 °C. The mixture was slowly heated to room temperature and stirred for 16 hours. The reaction solution was then cooled to 0 °C and the reaction was terminated by adding a saturated aqueous ammonium chloride solution. The reaction mixture was extracted three times with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and filtered under reduced pressure. The residue was then purified by column chromatography to give 7.7 g of intermediate 2-4 (yield: 68%).

[0484] C 29 H 21 BrO M+1: 465.08.

[0485] (3) Synthesis of intermediate products 2-5

[0486] 7.7 g of intermediate 2-4 was dissolved in 80 mL of dichloromethane, and 0.5 mL of methanesulfonic acid was added and the mixture was stirred for 3 hours. The reaction was terminated by adding 1 mL of triethylamine and filtered under reduced pressure. The residue was then purified by column chromatography to give 7.0 g of intermediate 2-5 (yield: 95%).

[0487] C 29 H 19 Br M+1: 447.07.

[0488] (4) Synthesis of Compound 2

[0489] 3 g of intermediate 2-5, 3 g of N-phenyl-[1,1'-biphenyl]-4-amine, 0.34 g of Pd2(dba)3, 0.1 mL of PtBu3, and 3.6 g of KOtBu were dissolved in 60 mL of toluene and stirred at 85 °C for 2 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water. The reaction mixture was extracted three times with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was then separated and purified by silica gel column chromatography to give 3.7 g of compound 2 (yield: 90%).

[0490] C 47 H 33 N M+1: 612.26.

[0491] 1 H NMR (500MHz, CDCl3) δ=7.72-7.50(m, 6H), 7.48-7.38(m, 5H), 7.25-6.94(m, 16H), 6.77(td, 1H), 6.55(dt, 1H), 6.09(m, 1H), 6.05(m, 2H), 6.00(dd, 1H).

[0492] Synthesis Example 2: Synthesis of Compound 10

[0493]

[0494] Except that 3g of N-phenyl-[1,1'-biphenyl]-2-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, 3.2g of compound 10 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 78%).

[0495] C 47 H 33 N M+1: 612.26.

[0496] 1 H NMR (500MHz, CDCl3) δ = 7.72-7.50 (m, 6H), 7.48-7.43 (m, 4H), 7.32 (dt, 1H), 7.25-6 .94 (m, 16H), 6.77 (td, 1H), 6.55 (dt, 1H), 6.09 (m, 1H), 6.05 (m, 2H), 6.00 (dd, 1H).

[0497] Synthesis Example 3: Synthesis of Compound 11

[0498]

[0499] Except that 3 g of N-phenyldibenzo[b,d]furan-1-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, 3.4 g of compound 11 was obtained in essentially the same manner as in the synthesis of compound 2 (yield: 81%).

[0500] C 47 H 31 NO M+1: 626.24.

[0501] 1 H NMR (500MHz, CDCl3) δ = 7.79 (m, 1H), 7.72-7.60 (m, 5H), 7.49-7.44 (m, 2H), 7.33-7.25 (m, 4H), 7.22-7.16(m, 4H), 7.15-6.99(m, 9H), 6.67(dd, 1H), 6.61(dt, 1H), 6.63(dd, 1H), 6.26(m, 3H).

[0502] Synthesis Example 4: Synthesis of Compound 16

[0503]

[0504] Except that 3 g of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (16-1) was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, and 3 g of intermediate 16-2 was used instead of intermediate 2-5, 3.0 g of compound 16 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 69%).

[0505] C 50 H 37 N M+1: 651.29.

[0506] 1 H NMR (500MHz, CDCl3) δ = 7.81 (dd, 1H), 7.75 (dd, 1H), 7.62 (s, 1H), 7.55-7.52 (m, 2H), 7.47-7.41 (m, 2H), 7.36 -7.25(m, 2H), 7.23-6.93(m, 16H), 6.82(td, 1H), 6.65-6.60(m, 2H), 6.36(d, 1H), 6.11(m, 2H), 1.61(s, 6H).

[0507] Synthesis Example 5: Synthesis of Compound 21

[0508]

[0509] Except that 3g of N-([1,1'-biphenyl]-4-yl)naphthyl-2-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, and 3g of intermediate 16-2 was used instead of intermediate 2-5, 2.7g of compound 21 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 60%).

[0510] C 51 H 35 N M+1: 662.28.

[0511] 1 H NMR (500MHz, CDCl3) δ = 7.81-7.75 (m, 2H), 7.70 (m, 1H), 7.66-7.60 (m, 3H), 7.59-7.34(m, 13H), 7.28-7.05(m, 12H), 6.99(dt, 1H), 6.84-6.74(m, 4H).

[0512] Synthesis Example 6: Synthesis of Compound 34

[0513]

[0514] (1) Synthesis of intermediate product 34-2

[0515] Except that 5 g of (4-fluoronaphth-1-yl)boronic acid (34-1) was used instead of naphthalene-1-boronic acid, 8 g of intermediate 34-2 was obtained in essentially the same manner as in the synthesis of intermediate 2-3 (yield: 85%).

[0516] C 18 H 12 BrFO2 M+1: 359.00.

[0517] (2) Synthesis of intermediate product 34-3

[0518] Except that 8g of intermediate 34-2 was used instead of intermediate 2-3, 8g of intermediate 34-3 was obtained in essentially the same manner as in the synthesis of intermediate 2-4 (yield: 74%).

[0519] C 29 H 20 BrFO M+1: 483.07.

[0520] (3) Synthesis of intermediate product 34-4

[0521] Except that 8g of intermediate 34-3 was used instead of intermediate 2-4, 6.5g of intermediate 34-4 was obtained in essentially the same manner as in the synthesis of intermediate 2-5 (yield: 84%).

[0522] C 29 H 18 BrF M+1: 465.06.

[0523] (4) Synthesis of compound 34

[0524] Except that 3g of intermediate 34-4 was used instead of intermediate 2-5, 3.4g of compound 34 was obtained in essentially the same manner as in the synthesis of compound 10 (yield: 84%).

[0525] C 47 H 32 FN M+1: 630.25.

[0526] 1 H NMR (500MHz, CDCl3) δ = 7.76-7.70 (m, 2H), 7.62-7.53 (m, 3H), 7.50-7.44 (m, 3H), 7.37-7 .30 (m, 5H), 7.25-6.95 (m, 13H), 6.77 (dd, 1H), 6.65 (dt, 1H), 6.18 (d, 1H), 6.06 (m, 3H).

[0527] Synthesis Example 7: Synthesis of Compound 38

[0528]

[0529] (1) Synthesis of intermediate product 38-3

[0530] Except that 10 g of (4-bromonaphth-1-yl)boronic acid (38-2) was used instead of naphthalene-1-boronic acid, 12 g of intermediate 38-3 was obtained in essentially the same manner as in the synthesis of intermediate 2-3 (yield: 80%).

[0531] C 18 H 12 BrFO2 M+1: 359.00.

[0532] (2) Synthesis of intermediate product 38-4

[0533] Except that 12g of intermediate 38-3 was used instead of intermediate 2-3, 14g of intermediate 38-4 was obtained in essentially the same manner as in the synthesis of intermediate 2-4 (yield: 87%).

[0534] C 29 H 20 BrFO M+1: 483.07.

[0535] (3) Synthesis of intermediate product 38-5

[0536] Except that 14g of intermediate 38-4 was used instead of intermediate 2-4, 8g of intermediate 38-5 was obtained in essentially the same manner as in the synthesis of intermediate 2-5 (yield: 59%).

[0537] C 29 H 18 BrF M+1: 465.06.

[0538] (4) Synthesis of compound 38

[0539] Except that 3g of intermediate 38-5 was used instead of intermediate 2-5, 3.1g of compound 38 was obtained in essentially the same manner as in the synthesis of compound 2 (yield: 60%).

[0540] C 47 H 32 FN M+1: 630.25.

[0541] 1H NMR (500MHz, CDCl3) δ = 7.77 (m, 1H), 7.65-7.60 (m, 2H), 7.55-7.28 (m, 11H), 7.22-6.94 (m, 12H), 6.78 (m, 2H), 6.65 (dt, 1H), 6.43 (dd, 1H), 6.12 (m, 2H).

[0542] Synthesis Example 8: Synthesis of Compound 54

[0543]

[0544] (1) Synthesis of intermediate product 54-1

[0545] 5 g of 1-bromo-4-methylbenzene was dissolved in THF and cooled to -78°C. 12.3 mL of n-BuLi (2.5 M hexane solution) was slowly added dropwise while maintaining the temperature. After 1 hour, 5 g of intermediate 2-3 dissolved in THF was slowly added dropwise to the reaction vessel. When the reaction was complete, the temperature was slowly raised to room temperature, and the reaction was terminated by adding a saturated ammonium chloride solution. The reaction mixture was extracted three times with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue obtained was separated and purified by silica gel column chromatography to give 4.8 g of intermediate 54-1 (yield: 66%).

[0546] C 31 H 25 BrO M+1: 493.11.

[0547] (2) Synthesis of intermediate product 54-2

[0548] Except for the use of 4.8 g of intermediate 54-1, 3.6 g of intermediate 54-2 was obtained in substantially the same manner as in the synthesis of intermediates 2-5 (yield: 75%).

[0549] C 31 H 23 Br M+1: 475.10

[0550] (3) Synthesis of compound 54

[0551] Except that 3g of N-phenyldibenzo[b,d]furan-2-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, and 3.5g of intermediate 54-2 was used instead of intermediate 2-5, 3.8g of compound 54 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 79%).

[0552] C 49 H 35NO M+1: 654.27.

[0553] 1 H NMR (500MHz, CDCl3) δ = 7.84 (m, 1H), 7.74-7.65 (m, 4H), 7.63 (m, 1H), 7.55-7.46 (m, 4H), 7.44 (m, 1H), 7.32 (dt, 1H) , 7.13-6.98 (m, 7H), 6.95 (dd, 1H), 6.86 (m, 4H), 6.67 (dt, 1H), 6.42 (d, 1H), 6.30 (m, 3H), 2.34 (s, 3H), 2.32 (s, 3H).

[0554] Synthesis Example 9: Synthesis of Compound 64

[0555]

[0556] (1) Synthesis of intermediate product 64-1

[0557] Except for the use of 5.5 g of 1-bromo-4-fluorobenzene, 6.6 g of intermediate 64-1 was obtained in substantially the same manner as in the synthesis of intermediate 2-4 (yield: 90%).

[0558] C 29 H 19 BrF2O M+1: 501.06.

[0559] (2) Synthesis of intermediate product 64-2

[0560] Except that 6.6 g of intermediate 64-1 was used instead of intermediate 2-4, 5.3 g of intermediate 64-2 (83%) was obtained in essentially the same manner as in the synthesis of intermediate 2-5.

[0561] C 29 H 17 BrF2 M+1: 484.05.

[0562] (3) Synthesis of compound 64

[0563] Except that 3g of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, and 3g of intermediate 64-2 was used instead of intermediate 2-5, 3.4g of compound 64 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 80%).

[0564] C 50 H 35 F2N M+1: 688.27.

[0565] 1 H NMR (500MHz, CDCl3) δ = 7.78 (td, 1H), 7.72-7.64 (m, 3H), 7.63 (m, 1H), 7.58 (d, 1H), 7.50 (d, 1H), 7.36-7.27 (m, 2H), 7.1 4-7.00 (m, 9H), 6.72 (dd, 1H), 6.66 (td, 1H), 6.51-6.46 (m, 4H), 6.42 (dd, 1H), 6.33 (dd, 2H), 6.22 (m, 2H), 1.62 (s, 6H).

[0566] Synthesis Example 10: Synthesis of Compound 81

[0567]

[0568] Except that 3g of intermediate 81-1 was used instead of intermediate 16-2, 3.7g of compound 81 was obtained in essentially the same manner as in the synthesis of compound 21 (yield: 74%).

[0569] C 51 H 35 N M+1: 662.28.

[0570] 1 H NMR (500MHz, CDCl3) δ = 7.78-7.62 (m, 7H), 7.57-7.32 (m, 11H), 7.31 (dt, 1H), 7 .18-7.01 (m, 8H), 6.96 (t, 1H), 6.78-6.75 (m, 4H), 6.41 (m, 2H), 5.71 (dd, 1H).

[0571] Synthesis Example 11: Synthesis of Compound 95

[0572]

[0573] Except that 2.5 g of intermediate 95-1 was used instead of intermediate 2-5, 2.5 g of compound 95 was obtained in essentially the same manner as in the synthesis of compound 11 (yield: 86%).

[0574] C 47 H 31 NO M+1: 626.24.

[0575] 1H NMR (500MHz, CDCl3) δ = 7.79-7.66 (m, 5H), 7.49-7.44 (m, 2H), 7.36-7.27 (m, 4H), 7.21-7.1 9(m, 4H), 7.14-7.01(m, 10H), 6.69-6.60(m, 2H), 6.39(dd, 1H), 6.34(m, 2H), 6.05(d, 1H).

[0576] Synthesis Example 12: Synthesis of Compound 98

[0577]

[0578] Except that 2.5 g of N-phenyl-[1,1'-biphenyl]-4-amine was used, and 2.5 g of intermediate 98-1 was used instead of 3 g of intermediate 2-5, 2.9 g of compound 98 was obtained in substantially the same manner as in the synthesis of compound 2 (yield: 85%).

[0579] C 47 H 33 N M+1: 612.26.

[0580] 1 H NMR (500MHz, CDCl3) δ = 7.92 (d, 1H), 7.67-7.58 (m, 4H), 7.54-7.30 (m, 7H), 7.26-7.01 (m, 13H), 6.94(dd, 1H), 6.83(m, 2H), 6.65(dt, 1H), 6.57(dd, 1H), 6.22(m, 2H), 5.58(t, 1H).

[0581] Synthesis Example 13: Synthesis of Compound 110

[0582]

[0583] (1) Synthesis of intermediate product 110-2

[0584] Except that 8.4 g of methyl 2-bromobenzoate (110-1) was used instead of methyl 5-bromo-2-iodobenzoate, and 10 g of (5-bromonaphth-1-yl)boronic acid was used instead of naphthalene-1-boronic acid, 8.8 g of intermediate 110-2 (yield: 68%) was obtained in substantially the same manner as in the synthesis of intermediates 2-3.

[0585] C 18 H 13 BrO2: M+1 341.01

[0586] (2) Synthesis of intermediate product 110-3

[0587] Except that 8.8 g of intermediate 110-2 was used instead of intermediate 2-3, 8.5 g of intermediate 110-3 was obtained in essentially the same manner as in the synthesis of intermediate 2-4 (yield: 71%).

[0588] C 29 H 21 BrO: M+1 465.08.

[0589] (3) Synthesis of intermediate product 110-4

[0590] Except that 8.5 g of intermediate 110-3 was used instead of intermediate 2-4, 6.6 g of intermediate 110-4 was obtained in essentially the same manner as in the synthesis of intermediate 2-5 (yield: 81%).

[0591] C 29 H 19 Br: M+1 447.07.

[0592] (4) Synthesis of compound 110

[0593] Except that 2.8 g of intermediate 110-4 was used instead of intermediate 16-2, 3.1 g of compound 110 was obtained in essentially the same manner as in the synthesis of compound 16 (yield: 71%).

[0594] C 50 H 37 N:M+1 652.29.

[0595] 1 H NMR (500MHz, CDCl3) δ = 7.81 (td, 1H), 7.76 (td, 1H), 7.63 (d, 1H), 7.55 (td, 1H), 7.51 (dd, 1H), 7.45 (dt, 1H), 7.36-7.25 (m, 2H), 7.22-7.01 (m, 15H), 6.86 (td, 1H), 6.81 (d, 1H), 6.65-6.59 (m, 2H), 6.37 (dd, 1H), 6.31 (m, 1H), 6.12-6.08 (m, 2H), 1.61 (s, 6H).

[0596] Synthesis Example 14: Synthesis of Compound 124

[0597]

[0598] Except that 2.6 g of intermediate 124-1 was used instead of intermediate 16-2, 2.7 g of compound 124 was obtained in essentially the same manner as in the synthesis of compound 16 (yield: 75%).

[0599] C 56 H 41 N:M+1 728.32.

[0600] 1 H NMR (500MHz, CDCl3) δ = 8.15 (d, 1H), 8.07-8.03 (m, 2H), 7.78 (d, 1H), 7.70 (d, 1H), 7.60-7.55 (m, 2H), 7.51-7.43 (m, 2H), 7.41-7.28 ( m, 4H), 7.25-7.18 (m, 4H), 7.13-7.02 (m, 10H), 6.88 (d, 1H), 6.72-6.70 (m, 2H), 6.42 (m, 2H), 6.29 (d, 1H), 6.22 (m, 2H), 1.62 (s, 6H).

[0601] Synthesis Example 15: Synthesis of Compound 136

[0602]

[0603] Except that 2.3 g of intermediate 136-1 was used instead of intermediate 16-2, 2.3 g of compound 136 was obtained in essentially the same manner as in the synthesis of compound 16 (yield: 69%).

[0604] C 50 H 36 FN: M+1 670.28.

[0605] 1 H NMR (500MHz, CDCl3) δ = 7.78 (td, 1H), 7.74 (dd, 1H), 7.58-7.52 (m, 2H), 7.48-7.40 (m, 2H), 7.36-7.28 (m, 1H), 7.25-7.20 (m, 4H), 7.18-7.05(m, 11H), 6.96(d, 1H), 6.72(dd, 1H), 6.66(t, 1H), 6.42-6.39(m, 2H), 6.29(d, 1H), 6.22(m, 2H), 1.62(s, 6H).

[0606] [Example]

[0607] Comparison Example 1

[0608] Corning 15Ω / cm 2 The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, ultrasonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrate was then placed in a vacuum deposition apparatus to be used as the anode.

[0609] Vacuum deposition of 2-TNATA on an ITO glass substrate to form a structure with A hole injection layer of a certain thickness was formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (hole transport material) was vacuum deposited on the hole injection layer to form a hole transport material with a certain thickness. A hole transport layer of a certain thickness.

[0610] 9,10-bis(naphthyl-2-yl)anthracene (ADN) (blue fluorescent host) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) (blue fluorescent dopant) were co-deposited on the hole transport layer at a weight ratio of 98:2 to form a structure with… The thickness of the emission layer.

[0611] Then, Alq3 is deposited on the emitter layer to form a structure with... An electron transport layer of a certain thickness is formed. Then, LiF (alkali metal halide) is deposited on the electron transport layer to form a layer with… An electron-injected layer of a certain thickness is formed. Al is then vacuum-deposited on the electron-injected layer to form a layer with… A cathode of a certain thickness is formed, thus creating a LiF / Al electrode. In this way, an organic light-emitting device is fabricated.

[0612]

[0613] Comparison Example 2

[0614] The organic light-emitting device was fabricated in essentially the same manner as Comparative Example 1, except that compound A was used instead of NPB when forming the hole transport layer.

[0615] Compound A

[0616]

[0617] Comparison Example 3

[0618] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound B was used instead of NPB when forming the hole transport layer.

[0619] Compound B

[0620]

[0621] Compare Example 4

[0622] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound C was used instead of NPB when forming the hole transport layer.

[0623] Compound C

[0624]

[0625] Compare Example 5

[0626] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound D was used instead of NPB when forming the hole transport layer.

[0627] Compound D

[0628]

[0629] Comparison Example 6

[0630] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound E was used instead of NPB when forming the hole transport layer.

[0631] Compound E

[0632]

[0633] Compare Example 7

[0634] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound F was used instead of NPB when forming the hole transport layer.

[0635] Compound F

[0636]

[0637] Compare Example 8

[0638] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound G was used instead of NPB when forming the hole transport layer.

[0639] Compound G

[0640]

[0641] Example 1

[0642] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 2 was used instead of NPB when forming the hole transport layer.

[0643] Example 2

[0644] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 10 was used instead of NPB when forming the hole transport layer.

[0645] Example 3

[0646] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 11 was used instead of NPB when forming the hole transport layer.

[0647] Example 4

[0648] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 16 was used instead of NPB when forming the hole transport layer.

[0649] Example 5

[0650] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 21 was used instead of NPB when forming the hole transport layer.

[0651] Example 6

[0652] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 34 was used instead of NPB when forming the hole transport layer.

[0653] Example 7

[0654] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 38 was used instead of NPB when forming the hole transport layer.

[0655] Example 8

[0656] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 54 was used instead of NPB when forming the hole transport layer.

[0657] Example 9

[0658] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 64 was used instead of NPB when forming the hole transport layer.

[0659] Example 10

[0660] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 81 was used instead of NPB when forming the hole transport layer.

[0661] Example 11

[0662] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 95 was used instead of NPB when forming the hole transport layer.

[0663] Example 12

[0664] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 98 was used instead of NPB when forming the hole transport layer.

[0665] Example 13

[0666] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 110 was used instead of NPB when forming the hole transport layer.

[0667] Example 14

[0668] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 124 was used instead of NPB when forming the hole transport layer.

[0669] Example 15

[0670] The organic light-emitting device was fabricated in essentially the same manner as in Comparative Example 1, except that compound 136 was used instead of NPB when forming the hole transport layer.

[0671] The organic light-emitting devices fabricated according to Comparative Examples 1 to 8 and Examples 1 to 15 were tested at 50 mA / cm using the following method. 2 Device performance (drive voltage, brightness, efficiency) at current densities and at 100 mA / cm² 2 The half-life at the current density is shown in Table 1.

[0672] -Brightness: Powered by a current-voltmeter (Keithley SMU 236), brightness is measured using a luminance meter PR650.

[0673] - Efficiency: Power was supplied by a current-voltmeter (Keithley SMU 236), and efficiency was measured using a luminance meter PR650.

[0674] Half-life refers to the amount of time (hr) that elapses when the brightness reaches 50% of the initial brightness (100%) (at 100 mA / cm²). 2 Down).

[0675] Table 1

[0676]

[0677]

[0678] Referring to Table 1, compared to the organic light-emitting device of Comparative Example 1 using NPB, the organic light-emitting devices of Examples 1 to 15 exhibit excellent IVL characteristics, including low driving voltage and improved efficiency, when using compounds according to one or more embodiments of the present disclosure as hole transport materials. Specifically, in Examples 1 to 15 using compounds according to one or more embodiments of the present disclosure as hole transport materials, the lifetime improvement effect is excellent and the lifetime is significantly improved. Compared to Comparative Examples 2 to 8 using compounds A to G, the driving voltage is improved, and the efficiency and half-life are also excellent.

[0679] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects within each embodiment should generally be regarded as other similar features or aspects that can be used in other embodiments.

[0680] As used herein, when expressions such as “at least one of…”, “one of…”, “selected from…”, “at least one of…”, and “selected from…” precede or follow a column of elements, they modify the entire column of elements, rather than individual elements in that column. Additionally, in describing embodiments of this disclosure, the use of “may” means “one or more embodiments of this disclosure”.

[0681] As used herein, the term “use” and its variants may be considered synonymous with the term “utilize” and its variants, respectively.

[0682] As used herein, the terms “substantially,” “approximately,” and similar terms are used as approximations rather than as terms of degree and are intended to account for inherent biases in measurements or calculations that would be recognized by one of ordinary skill in the art.

[0683] Furthermore, any numerical range stated herein is intended to include all subranges with the same numerical precision contained within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the stated minimum value of 1.0 and the stated maximum value of 10.0 (inclusive), that is, a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly state any subranges contained within the range expressly stated herein.

[0684] Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made herein without departing from the spirit and scope as defined by the claims and their equivalents.

Claims

1. An amine compound, said amine compound being represented by Formula 1: Formula 1 ， Formula 2 ， in, In Equations 1 and 2, Ar1 and Ar2 are both independently selected from: Phenyl; as well as Substitutions include deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 The phenyl group selected from at least one of the alkyl groups, L1 and L2 are both independently selected from any one of the groups represented by formula 3-1, formula 3-2 and formula 3-34: ， Among them, in equations 3-1, 3-2 and 3-34, Z1 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 alkyl, d4 is an integer from 0 to 4, where when d4 is two or greater, two or more Z1s are identical or different from each other, and and 'These all refer to the bonding sites with adjacent atoms,' a1 and a2 are both independent integers from 0 to 2, where when a1 is 2, the two L1 values ​​are either the same or different, and when a2 is 2, the two L2 values ​​are either the same or different. When a1 is zero -(L1) a1 - ' is a single bond, and when a2 is zero, -(L2) a2 - ' is a single key, R1 to R 10 All are independently selected from groups represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, groups represented by Formula 5-1, and biphenyl. Formula 5-1 The prerequisite is that one of R5 to R8 is a group represented by Formula 2. In Equation 5-1, Z 31 Selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C 20 alkyl, e5 is an integer from 0 to 5, where when e5 is two or greater, it represents two or more Z. 31 They are the same or different from each other, and Refers to the bonding site with adjacent atoms. R 11 and R 12 Each group is independently selected from any one of the groups represented by formulas 6-1 to 6-10, 6-13 to 6-18, and 6-27 to 6-34: ， Among them, in equations 6-1 to 6-10, 6-13 to 6-18, and 6-27 to 6-34, Ph refers to phenyl, and Refers to the bonding site with adjacent atoms. b1 and b2 are both independent integers from 1 to 2, where when b1 is 2, the two R values ​​are... 11 They are either the same or different, and when b2 is two, the two Rs are... 12 They are the same or different from each other.

2. The amine compound according to claim 1, wherein, a1 and a2 are both independently 0 or 1.

3. The amine compound according to claim 1, wherein: R1 to R 10 Each group is independently selected from the group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and phenyl.

4. The amine compound according to claim 1, wherein, The amine compounds are represented by formulas 1-5: Formula 1-5 ， Among them, in equations 1-5, Ar1, Ar2, L1, L2, a1, a2, R1 to R7, R9 to R 12 b1 and b2 are the same as those described in Equations 1 and 2.

5. The amine compound according to claim 4, wherein, R1 to R7, R9 and R 10 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, phenyl, and biphenyl.

6. The amine compound according to claim 1, wherein, The amine compounds are selected from the following compounds: 。 7. An organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode faces the first electrode; as well as An organic layer is located between the first electrode and the second electrode. The organic layer includes an emitter layer, a hole transport region located between the first electrode and the emitter layer, and an electron transport region located between the emitter layer and the second electrode. The hole transport region comprises only one type of amine compound. The amine compound is selected from any one of compounds 1 to 144: 。 8. An organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode faces the first electrode; as well as An organic layer is located between the first electrode and the second electrode. The organic layer includes an emitter layer and a hole transport region located between the first electrode and the emitter layer. The hole transport region comprises only one amine compound represented by Formula 1: Formula 1 ， Formula 2 ， Among them, in Equations 1 and 2, Ar1 and Ar2 are both independently selected from: Phenyl; and Substitutions include deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 The phenyl group selected from at least one of the alkyl groups, L1 and L2 are both independently selected from any one of the groups represented by formula 3-1, formula 3-2 and formula 3-34: Among them, in equations 3-1, 3-2 and 3-34, Z1 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 alkyl, d4 is an integer from 0 to 4, where when d4 is two or greater, two or more Z1s are identical or different from each other, and and 'These all refer to the bonding sites with adjacent atoms,' a1 and a2 are both independent integers from 0 to 2, where when a1 is 2, the two L1 values ​​are either the same or different, and when a2 is 2, the two L2 values ​​are either the same or different. When a1 is zero -(L1) a1 - ' is a single bond, and when a2 is zero, -(L2) a2 - ' is a single key, R1 to R 10 All are independently selected from groups represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, groups represented by Formula 5-1, and biphenyl. Formula 5-1 The prerequisite is that one of R5 to R8 is a group represented by Formula 2. In Equation 5-1, Z 31 Selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C 20 alkyl, e5 is an integer from 0 to 5, where when e5 is two or greater, it represents two or more Z. 31 They are the same or different from each other, and Refers to the bonding site with adjacent atoms. R 11 and R 12 Each group is independently selected from any one of the groups represented by formulas 6-1 to 6-10 and 6-13 to 6-34: ， Among them, in equations 6-1 to 6-10 and equations 6-13 to 6-34, Ph refers to phenyl, and Refers to the bonding site with adjacent atoms. b1 and b2 are both independent integers from 1 to 2, where when b1 is 2, the two R values ​​are... 11 They are either the same or different, and when b2 is two, the two Rs are... 12 They are the same or different from each other.

9. The organic light-emitting device according to claim 8, wherein: The first electrode is the anode. The second electrode is a cathode. The organic layer further includes an electron transport region located between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

10. The organic light-emitting device according to claim 9, wherein, The hole transport region includes the hole transport layer, and the hole transport layer includes the amine compound.

11. The organic light-emitting device according to claim 9, wherein: The hole transport region includes a p-doped agent, and The p-doped agent has a lowest unoccupied molecular orbital energy level of -3.5 eV or less.

12. The organic light-emitting device according to claim 8, wherein, The emission layer comprises at least one selected from styrene compounds, anthracene compounds, pyrene compounds, and spirodifluorene compounds.

13. The organic light-emitting device according to claim 8, wherein: The emitting layer is a first emitting layer used to emit light of the first color. The organic light-emitting device further includes, located between the first electrode and the second electrode: i) at least one second emitting layer for emitting a second color light, or ii) at least one second emitting layer for emitting a second color light and at least one third emitting layer for emitting a third color light. The maximum emission wavelengths of the first color light, the second color light, and the third color light may be the same as or different from each other, and The first color light and the second color light are emitted in the form of a mixed light, or the first color light, the second color light and the third color light are emitted in the form of a mixed light.

14. The organic light-emitting device according to claim 8, wherein, The amine compounds are selected from the following compounds: 。

Images