Amine compound and organic light-emitting device including the same

Abstract

Provided are an amine compound represented by Formula 1 and an organic light-emitting device including the same. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes at least one amine compound represented by Formula 1.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0063270 filed on May 26, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Art 1. Technical Field

[0004] One or more embodiments of the present disclosure relate to an amine compound and an organic light-emitting device including the same.

[0005] 2. Description of related technologies

[0006] An organic light emitting device (OLED) is a self-emitting device that has a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to other devices, and produces a full-color image.

[0007] An OLED may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emission layer to produce excitons. These excitons transition (e.g., relax) from an excited state to a ground state, thereby generating light. Summary of the invention

[0008] One or more embodiments include an amine compound and an organic light-emitting device including the same.

[0009] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments presented in the disclosure.

[0010] According to one aspect of an embodiment, an amine compound represented by Formula 1 is provided.

[0011] Formula 1

[0012]

[0013] In formula 1, L 1 To L 4 , L 11 and L 12 may be independently substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0014] a1 to a4, a11 and a12 may each independently be an integer selected from 0 to 5,

[0015] Ar 1 To Ar 4 may be independently substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0016] Excluding Ar 1 To Ar 4 In the case where two or more of each of the two or more of the amino groups include an amino group (for example, Ar 1 To Ar 4 each excluding amine groups),

[0017] R 1 To R 3 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),

[0018] D 1 To D 3 Each is deuterium,

[0019] b1 to b3 and c1 to c3 may each independently be an integer selected from 0 to 4,

[0020] The sum of b1 and c1, the sum of b2 and c2, and the sum of b3 and c3 are each 4,

[0021] The sum of c1, c2 and c3 can be 1 or greater, and

[0022] Substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0023] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy,

[0024] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 ),

[0025] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups,

[0026] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q22 )(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 ),as well as

[0027] -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 ),

[0028] Where Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.

[0029] Another aspect of an embodiment of the present disclosure provides an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes at least one amine compound represented by Formula 1 as described above. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:

[0031] Figure 1 is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

[0032] Figure 2 is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

[0033] Figure 3 is a schematic cross-sectional view of an embodiment of an organic light-emitting device; and

[0034] Figure 4 is a schematic cross-sectional view of an embodiment of an organic light-emitting device. DETAILED DESCRIPTION

[0035] Reference will now be made in more detail to embodiments, examples of which are shown in the accompanying drawings, wherein the same reference numerals throughout this document refer to the same elements. In this regard, embodiments may have different forms and should not be construed as being limited to the description set forth herein. Therefore, embodiments are described below with reference to the figures only to explain aspects of the embodiments of this description. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. Throughout this disclosure, the expression "at least one of a, b, and c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0036] The amine compound according to an embodiment is represented by Formula 1:

[0037] Formula 1

[0038]

[0039] L in Formula 1 1 To L 4 , L 11 and L 12 may be independently substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60Heterocyclic group.

[0040] In an embodiment, L 1 To L 4 , L 11 and L 12 may be each independently selected from phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, spiro-fluorene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenanylene, hexaphenylene, pentaphenylene, rubenylene, coronenylene, ovophenylene and carbazolylene; and

[0041] phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, spiro-fluorene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubenylene, coroneylene, ovopheneylene and carbazolylene, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenylene, pyrenyl, peryl, pentaphenanthrenyl, hexaphenylene, pentacene, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazine , pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, dibenzothioxyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q33 )、-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 ),

[0042] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, C 1 -C 10 Alkyl-substituted phenyl, biphenyl, terphenyl and naphthyl.

[0043] For example, L 1 To L 4 , L 11 and L 12 may each independently be a group represented by one of Formulae 3-1 to 3-27:

[0044]

[0045]

[0046] Among them, in formulas 3-1 to 3-27,

[0047] Y 11 Can be selected from C(Z 3 )(Z 4 )、N(Z 5 )、Si(Z 6 )(Z 7 ), O and S, and

[0048] Z 1 To Z 7 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, thirol, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, benzothirol, dibenzothirol and -Si(Q) 31 )(Q 32 )(Q 33 ),

[0049] Where Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl and pyridyl,

[0050] d2 may be an integer selected from 0 to 2,

[0051] d3 may be an integer selected from 0 to 3,

[0052] d4 may be an integer selected from 0 to 4,

[0053] d6 may be an integer selected from 0 to 6,

[0054] d8 may be an integer selected from 0 to 8, and

[0055] *, *' and *" each indicate a binding site with an adjacent atom.

[0056] In Formula 1, a1 to a4, a11, and a12 may each independently be an integer selected from 0 to 5.

[0057] In an embodiment, a11 and a12 are each 0.

[0058] In an embodiment, a1 to a4 may each independently be an integer selected from 0 to 3.

[0059] For example, a1 to a4 may each independently be an integer selected from 0 to 2.

[0060] Ar in Formula 1 1 To Ar 4 may be independently substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups, excluding those in which Ar 1 To Ar4 In the case where two or more of the 1 To Ar 4 each excluding amine groups).

[0061] In an embodiment, Ar 1 To Ar 4 Can be independently selected from:

[0062] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolyl, isoquinolyl, benzoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothienyl, biphenyl and terphenyl; and

[0063] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirol, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolyl, isoquinolyl quinolinyl, benzoquinolinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl , acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, dibenzothirolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirolyl, biphenyl and terphenyl.

[0064] For example, Ar 1 To Ar 4 may each independently be a group represented by one of formulae 5-1 to 5-27:

[0065]

[0066] Among them, in formulas 5-1 to 5-27,

[0067] Y 31 Can be O, S, C (Z 35 )(Z 36 ) or Si(Z 37 )(Z 38 );

[0068] Z 31 To Z 38 can be independently selected from any one of the following: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0069] e3 may be an integer selected from 0 to 3,

[0070] e4 may be an integer selected from 0 to 4,

[0071] e5 may be an integer selected from 0 to 5,

[0072] e6 may be an integer selected from 0 to 6,

[0073] e7 may be an integer selected from 0 to 7,

[0074] e9 may be an integer selected from 0 to 9, and

[0075] *Indicates the binding site with the neighboring atoms.

[0076] In an embodiment, Ar 1 To Ar 4 Neither may include an amine group.

[0077] In formula 1, R 1 To R 3 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and

[0078] D 1 To D 3 Each is deuterium.

[0079] In an embodiment, R 1 To R 3 Can be independently selected from:

[0080] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, biphenyl and terphenyl; and

[0081] Each of which is substituted by at least one of the following: methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl.

[0082] For example, R 1 To R 3 At least one of may be hydrogen.

[0083] For example, R 1 To R 3 Each of may be hydrogen.

[0084] b1 to b3 and c1 to c3 in Formula 1 may each independently be an integer selected from 0 to 4,

[0085] The sum of b1 and c1, the sum of b2 and c2, and the sum of b3 and c3 are each 4, and

[0086] The sum of c1, c2, and c3 may be 1 or greater.

[0087] In an embodiment, one of c1 to c3 may be 4 and the other two may each be 0.

[0088] Two of c1 to c3 may each be 4 and the other one may be 0, or

[0089] c1 to c3 are 4, respectively.

[0090] For example, c1 may be 4 and c2 and c3 may each be 0. For example, c2 may be 4 and c1 and c3 may each be 0. For example, c3 may be 4 and c1 and c2 may each be 0. For example, c1 and c2 may each be 4 and c3 may be 0. For example, c1 and c3 may each be 4 and c2 may be 0. For example, c2 and c3 may each be 4 and c1 may be 0. For example, c1, c2, and c3 may each be 4.

[0091] In one or more embodiments, the sum of c1, c2, and c3 may be 2 or greater (or 4 or greater).

[0092] For example, the sum of c1, c2, and c3 may be 3 or more. For example, the sum of c1, c2, and c3 may be 4 or more. For example, the sum of c1, c2, and c3 may be 4, 8, or 12.

[0093] In an embodiment, in Formula 1, The moiety represented by may be a group represented by one of Formulae 2-1 to 2-6:

[0094]

[0095] Among them, in formulas 2-1 to 2-6,

[0096] R 1 To R 3 , D 1 To D 3 , b1 to b3 and c1 to c3 are the same as described above, and

[0097] * and *' each indicate a binding site with an adjacent atom.

[0098] For example, in Formula 1, The part represented by may be a group represented by Formula 2-1.

[0099] Therefore, in some embodiments, the amine compound represented by Formula 1 may be represented by Formula 10:

[0100] Formula 10

[0101]

[0102] In formula 10,

[0103] L 1 To L 4 、a1 to a4、Ar 1 To Ar 4 , R 1 To R 3 , D 1 To D 3 , b1 to b3 and c1 to c3 are the same as described above.

[0104] In an embodiment, the amine compound represented by Formula 1 may include at least four deuteriums (eg, at least four deuterium atoms).

[0105] In an embodiment, the amine compound may be selected from Compounds 1 to 192:

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] The amine compound may be represented by Formula 1, which may include two amine groups. Due to this structure, the amine compound has a flat structure and is easy to laminate, resulting in a low refractive index effect. For example, due to its structure, most of the amine compound is substantially on a single plane, thereby improving the ability to stack the amine compound (e.g., making it relatively easier to laminate the amine compound), for example, stacking the amine compound on other molecules of the amine compound.

[0115] In addition, the amine compound includes three or more phenylene groups as a linker in the amine group, so that the glass transition temperature and / or thermal stability of the amine compound increases.

[0116] In addition, in the amine compound, optionally, the amine group and three or more phenylene linkers are connected (e.g., bonded) relative to each other at the para position. Therefore, the intermolecular interaction between the molecules of the amine compound can be reduced, and the glass transition temperature of the amine compound is increased, the synthesis yield is improved, and high efficiency is shown.

[0117] Furthermore, since one or more (optionally, four or more) deuteriums (eg, four or more deuterium atoms) are included in the linker between amine groups, the amine compound may exhibit a long lifespan.

[0118] In addition, since the amine compound does not include two or more amine groups in the substituent of the amine group, the energy level in the device is adjusted, and a suitable or appropriate energy level for the device using the amine compound can be obtained.

[0119] Therefore, an electronic device, such as an organic light-emitting device, using the amine compound represented by Formula 1 may have low driving voltage, high brightness, high efficiency, and a long lifespan.

[0120] A person of ordinary skill in the art may recognize a method for synthesizing the amine compound represented by Formula 1 by referring to the examples provided below.

[0121] At least one such amine compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the amine compound may be included in at least one selected from a hole transport region and an emission layer. In one or more embodiments, the amine compound represented by Formula 1 may be used as a material for a capping layer outside the pair of electrodes of an organic light-emitting device.

[0122] Therefore, another aspect of an embodiment of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic light-emitting device includes at least one amine compound represented by Formula 1. For example, the organic layer includes at least one amine compound.

[0123] For example, the organic layer may include one or more amine compounds represented by Formula 1.

[0124] As used herein, the expression “(the organic layer) includes at least one amine compound” may include the case where “(the organic layer) includes the same amine compound represented by Formula 1” and the case where “(the organic layer) includes two or more different amine compounds represented by Formula 1”.

[0125] For example, the organic layer may include only compound 1 as an amine compound. In this embodiment, compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as amine compounds. In this embodiment, compounds 1 and 2 may be included in the same layer (for example, compounds 1 and 2 may both be included in the emission layer) or in different layers (for example, compound 1 may be included in the emission layer, and compound 2 may be included in the electron transport layer).

[0126] In some embodiments,

[0127] The first electrode of the organic light-emitting device may be an anode.

[0128] The second electrode of the organic light-emitting device may be a cathode, and

[0129] The organic layer of the organic light-emitting device may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode.

[0130] The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer, and

[0131] 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.

[0132] In an embodiment, the amine compound represented by Formula 1 may be included in the hole transport region.

[0133] In an embodiment, the hole transport region may include a hole transport layer, and the amine compound may be included in the hole transport layer.

[0134] In an embodiment, the hole transport region may include a first hole transport layer between the first electrode and the emission layer, and a second hole transport layer between the first hole transport layer and the emission layer, and

[0135] An amine compound may be included in the first hole transport layer.

[0136] In an embodiment, the hole transport region may include a first hole transport layer between the first electrode and the emission layer, and a second hole transport layer between the first hole transport layer and the emission layer, and

[0137] An amine compound may be included in the second hole transport layer.

[0138] In an embodiment, the emission layer includes a host and a dopant, and the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0139] In an embodiment, the electron transport region 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.

[0140] As used herein, the term "organic layer" refers to a single layer and / or all layers between the first electrode and the second electrode of the organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials. For example, the organic layer may include an inorganic material.

[0141] Figure 1 Description

[0142] Figure 1 2 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0143] In the following, we will combine Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to an embodiment are described.

[0144] First electrode 110

[0145] exist Figure 1 In the embodiment, the substrate may be additionally below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling and / or waterproofness.

[0146] The first electrode 110 may be formed, for example, by depositing and / or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0147] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0148] 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 thereto.

[0149] Organic layer 150

[0150] The organic layer 150 is on the first electrode 110. The organic layer 150 may include an emission layer.

[0151] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .

[0152] Hole transport region in the organic layer 150

[0153] The hole transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0154] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.

[0155] In an embodiment, the hole transport zone may have a single-layer structure including a single layer (including a plurality of different materials), or a multilayer 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 / emission auxiliary layer structure, wherein for each structure, the constituent layers are stacked sequentially in the order stated starting from the first electrode 110, but the structure of the hole transport zone is not limited thereto.

[0156] The hole transport region may include at least one selected from the following: m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0157]

[0158] Among them, in equations 201 and 202,

[0159] L 201 To L 204 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0160] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0161] xa1 to xa4 are each independently an integer selected from 0 to 3,

[0162] xa5 is an integer selected from 1 to 10, and

[0163] R 201 To R 204 and Q 201may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0164] For example, R in Equation 202 201 and R 202 may be optionally linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 Optionally they may be linked to one another via single bonds, dimethyl-methylene or diphenyl-methylene.

[0165] In an embodiment, in equations 201 and 202,

[0166] L 201 To L 205 Can be independently selected from:

[0167] Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pyren ... pentaphenylene, hexaphenylene, pentaphenylene, rubidinylene, coronenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridylene; and

[0168] each substituted with at least one selected from the following: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenanylene, hexaphenylene , pentaphenylene, rubidinyl, coronene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenyl, pyrenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, rubenyl, coronenyl, ovophene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),

[0169] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0170] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.

[0171] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0172] In one or more embodiments, R201 To R 204 and Q 201 each independently selected from the group consisting of phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, pyrenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, rubinyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl; and

[0173] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, pyrenyl, peryl, pentaphenanthrenyl, hexacene phenyl, pentacene, rubinyl, coryl, ovale, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenyl, pyrenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, rubenyl, coronenyl, ovophene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),

[0174] Where Q 31 To Q 33Same as described above.

[0175] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of can be independently selected from:

[0176] fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and

[0177] Fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,

[0178] However, the embodiments of the present disclosure are not limited thereto.

[0179] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be connected to each other via a single bond, and / or ii) R 203 and R 204 Can be connected to each other via a single bond.

[0180] In one or more embodiments, R in Formula 202 201 To R 204 At least one of can be selected from:

[0181] carbazolyl; and

[0182] A carbazolyl group substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,

[0183] However, the embodiments of the present disclosure are not limited thereto.

[0184] The compound represented by Formula 201 can be represented by the following Formula 201-1:

[0185] Formula 201-1

[0186]

[0187] In an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201-2, but embodiments of the present disclosure are not limited thereto:

[0188] Formula 201-2

[0189]

[0190] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), but the embodiments of the present disclosure are not limited thereto:

[0191] Formula 201-2(1)

[0192]

[0193] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A:

[0194] Formula 201A

[0195]

[0196] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:

[0197] Formula 201A(1)

[0198]

[0199] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but embodiments of the present disclosure are not limited thereto:

[0200] Formula 201A-1

[0201]

[0202] In an embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1:

[0203] Formula 202-1

[0204]

[0205] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202-1(1):

[0206] Formula 202-1(1)

[0207]

[0208] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A:

[0209] Formula 202A

[0210]

[0211] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A-1:

[0212] Formula 202A-1

[0213]

[0214] In formulas 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A and 202A-1,

[0215] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,

[0216] L 205 may be selected from phenylene and fluorene,

[0217] X 211 Can be selected from O, S and N (R 211 ),

[0218] X 212 Can be selected from O, S and N (R 212 ),

[0219] R 211 and R 212 Combined with R 203 Same as described, and

[0220] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetracenyl, pyrenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridinyl.

[0221] The hole transport region may include at least one compound selected from compounds HT1 to HT48, but embodiments of the present disclosure are not limited thereto:

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about For example, about to about and the thickness of the hole transport layer may be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, appropriate or satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0228] The emission assisting layer may increase light emission efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may include materials as described above.

[0229] p-dopant

[0230] In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive (eg, electrical conductivity) property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0231] The charge generating material may be, for example, a p-dopant.

[0232] In an embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.

[0233] The p-dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

[0234] In an embodiment, the p-dopant may include at least one selected from the following:

[0235] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0236] Metal oxides, such as tungsten oxide and / or molybdenum oxide;

[0237] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0238] A compound represented by the following formula 221,

[0239] However, the embodiments of the present disclosure are not limited thereto:

[0240]

[0241] Among them, in formula 221,

[0242] R 221 To R 223 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and is selected from R 221 To R 223 At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl and C substituted by -I 1 -C 20 alkyl.

[0243] Emission layer in the organic layer 150

[0244] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer, and the blue emission layer, wherein the two or more layers are in contact with each other (e.g., physical contact) or separated from each other (e.g., spaced apart). In one or more embodiments, the emission layer may include two or more materials selected from the red light-emitting material, the green light-emitting material, and the blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0245] The emission layer may include a host and a light-emitting material. The light-emitting material may include at least one selected from a phosphorescent dopant, a fluorescent dopant, and a quantum dot.

[0246] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on about 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0247] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within any of the aforementioned ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0248] Subject in the emission layer

[0249] The host may include an amine compound represented by Formula 1.

[0250] The host may further include a compound represented by Formula 301.

[0251] Formula 301

[0252] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0253] Wherein, in Formula 301,

[0254] Ar 301 Can be substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0255] xb11 can be 1, 2 or 3,

[0256] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0257] xb1 may be an integer selected from 0 to 5,

[0258] R 301 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),and

[0259] xb21 may be an integer selected from 1 to 5,

[0260] Where Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0261] In an embodiment, Ar in Formula 301 301 You can choose from:

[0262] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0263] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, pyrenyl, peryl, pentaphenanthracene, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -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 ),

[0264] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments of the present disclosure are not limited thereto.

[0265] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be connected via one-touch.

[0266] In one or more embodiments, the compound represented by Formula 301 may be represented by one of Formula 301-1 and Formula 301-2:

[0267] Formula 301-1

[0268]

[0269] Formula 301-2

[0270]

[0271] In formulas 301-1 and 301-2

[0272] A 301 To A 304 The benzophenanthrene ring may be independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a 1,2-triphenylene ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring and a dinaphthothiophene ring,

[0273] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0274] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -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 ),

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

[0276] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0277] L 302 To L 304 Each independently and in combination with L 301 Same as described,

[0278] xb2 to xb4 may each independently be the same as described in conjunction with xb1, and

[0279] R 302 To R 304 Each independently and in combination with R 301 Same as described.

[0280] For example, L in equations 301, 301-1, and 301-2 301 To L 304 Can be independently selected from:

[0281] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0282] each substituted with at least one selected from the following: phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, 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 )(Q32 ),

[0283] Where Q 31 To Q 33 Same as described above.

[0284] In an embodiment, R in Formulas 301, 301-1, and 301-2 301 To R 304 Can be independently selected from:

[0285] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazole yl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0286] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl oxazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, 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 ),

[0287] Where Q 31 To Q 33 Same as described above.

[0288] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0289] The host may include at least one selected from the following: 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and at least one selected from compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:

[0290]

[0291]

[0292]

[0293] The phosphorescent dopant included in the emission layer in the organic layer 150

[0294] The phosphorescent dopant may include an organic metal compound complex represented by the following Formula 401:

[0295] Formula 401

[0296] M(L 401 ) xc1 (L 402 ) xc2

[0297] Wherein, in Formula 401,

[0298] M may 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),

[0299] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,

[0300] Formula 402

[0301]

[0302] L 402 may be an organic ligand, and xc2 may be an integer selected from 0 to 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,

[0303] In formula 402,

[0304] X 401 To X 404 may each independently be nitrogen or carbon,

[0305] X 401 and X 403 Can be connected via single or double bonds, and X 402 and X 404 Can be connected via single or double bonds,

[0306] A 401 and A 402 Can be independently C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0307] 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 Q 411 and Q 412 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,

[0308] X 406 Can be a single bond, O or S,

[0309] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), and Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,

[0310] xc11 and xc12 may each independently be an integer selected from 0 to 10, and

[0311] * and *' in Formula 402 each indicate a binding site with M in Formula 401.

[0312] In an embodiment, A in Formula 402 401 and A 402 The benzofuranyl, benzothiophenyl, benzoisothiophenyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, and dibenzothiophenyl may be independently selected from the group consisting of phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiophenyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl.

[0313] In one or more embodiments, in Formula 402, i) X 401 Can be nitrogen and X 402 Can be carbon, or ii) X 401 and X 402 Each is nitrogen at the same time.

[0314] In one or more embodiments, R in Formula 402 401 and R 402 Can be independently selected from:

[0315] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0316] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl;

[0317] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;

[0318] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and -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 ),

[0319] Where Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0320] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 Two A's 401 Optionally, X 407 (which is a connecting group) connected to each other, two A 402 Optionally, X 408 (which is a linking group) are connected to each other (see compounds PD1 to PD4 and PD7). 407 and X 408 can be each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments of the present disclosure are not limited thereto.

[0321] L in Formula 401 402 It can be a monovalent, divalent or trivalent organic ligand. For example, L 402 It may be selected from halogen, diketone (eg, acetylacetonate), carboxylic acid (eg, picolinate), -C(=O), isonitrile, -CN, and phosphorus-containing ligands (eg, phosphine and / or phosphite), but the embodiments of the present disclosure are not limited thereto.

[0322] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but embodiments of the present disclosure are not limited thereto:

[0323]

[0324]

[0325] Fluorescent dopants in the emitting layer

[0326] The fluorescent dopant may include an amine compound represented by Formula 1.

[0327] The fluorescent dopant may include an aromatic amine compound and / or a styrylamine compound.

[0328] The fluorescent dopant may include a compound represented by the following Formula 501:

[0329] Formula 501

[0330]

[0331] Wherein, in Formula 501,

[0332] Ar 501 Can be substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0333] L 501 To L 503 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0334] xd1 to xd3 may each independently be an integer selected from 0 to 3,

[0335] R 501 and R 502 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

[0336] xd4 may be an integer selected from 1-6.

[0337] In an embodiment, Ar in Formula 501 501 You can choose from:

[0338] naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0339] naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl and indenophenanthrenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0340] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:

[0341] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenanthrenylene, perylene, pentaphenylene, hexaphenylene, pentacenylenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridylene; and

[0342] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, and pyridylene, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridinyl.

[0343] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:

[0344] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0345] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, and pyridyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl and -Si(Q) 31 )(Q 32 )(Q 33 ),

[0346] Where Q 31 To Q 33 Can be selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0347] In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.

[0348] For example, the fluorescent dopant may be selected from compounds FD1 to FD22:

[0349]

[0350]

[0351]

[0352] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments of the present disclosure are not limited thereto.

[0353]

[0354] quantum dots

[0355] An emission layer included in the organic light-emitting device of the present disclosure may include quantum dots.

[0356] Quantum dots are particles having a crystal structure of several to tens of nanometers and include hundreds to thousands of atoms.

[0357] Because the size of quantum dots is very small, a quantum confinement effect may occur. The quantum confinement effect refers to a phenomenon in which the band gap of an object becomes larger when the object becomes smaller than the nanometer size (e.g., having a size of nanometer scale and greater than 1 nanometer). Therefore, when light with a wavelength having an energy intensity greater than the band gap of the quantum dot is irradiated to the quantum dot, the quantum dot is excited by absorbing the light, and then emits light with a set or specific wavelength when it transitions (e.g., relaxes) to the ground state. In this case, the wavelength of the emitted light has a value corresponding to the band gap.

[0358] The core of the quantum dot may include a Group II-VI compound, a Group III-VI compound, a Group III-V compound, a Group IV-VI compound, a Group IV element or compound, a Group I-III-VI compound, or a combination thereof.

[0359] The II-VI Group compounds may be selected from: binary compounds selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and any mixture thereof; binary compounds selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZn Te, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and any mixture thereof; and a quaternary compound selected from CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and any mixture thereof.

[0360] Group III-VI compounds may include: binary compounds, such as In 2 S 3 and / or In 2 Se; ternary compounds, such as InGaS 3 or InGaSe 3 ; or any combination thereof.

[0361] For example, the Group III-V compounds may be selected from: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and any mixture thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and any mixture thereof; and quaternary compounds selected from GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, GaAlNP and any mixture thereof, but the embodiments of the present disclosure are not limited thereto. The Group III-V semiconductor compound may further include a Group II metal (eg, InZnP, etc.).

[0362] The IV-VI group compound may be selected from: a binary compound selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe and any mixture thereof; a ternary compound selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and any mixture thereof; and a quaternary compound selected from SnPbSSe, SnPbSeTe, SnPbSTe and any mixture thereof. The IV group element may be selected from Si, Ge and any mixture thereof. The IV group compound may be a binary compound selected from SiC, SiGe and any mixture thereof.

[0363] The binary compound, ternary compound or quaternary compound may be present in the particle at a uniform (e.g., substantially uniform) concentration, or may be present in the same particle in a state where the concentration distribution is partially different. In addition, the binary compound, ternary compound and / or quaternary compound may have a core-shell structure in which one quantum dot surrounds another quantum dot. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases in a direction toward the center.

[0364] In one or more embodiments, the quantum dot may have a core-shell structure including a core having the above-mentioned nanoparticles and a shell surrounding the core. The shell of the quantum dot may be used as a protective layer for maintaining semiconductor properties by preventing or reducing chemical degradation of the core, and / or may be used as a charging layer for imparting electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient, wherein the concentration of the elements present in the shell decreases in a direction toward the center. Examples of the shell of the quantum dot are metal or non-metal oxides, semiconductor compounds, or any combination thereof.

[0365] Examples of metal or nonmetal oxides are binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and NiO, and / or ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 , but the embodiments of the present disclosure are not limited thereto.

[0366] In addition, examples of semiconductor compounds are CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP and AlSb, but the embodiments of the present disclosure are not limited thereto.

[0367] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less. In addition, the light emitted by such quantum dots is irradiated in all directions (for example, substantially in every direction). Therefore, the wide viewing angle can be increased.

[0368] The shape of the quantum dots is not limited as long as the shape is commonly used in the art. In one or more embodiments, the quantum dots may include spherical, pyramidal, multi-armed and / or cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplate particles.

[0369] Quantum dots can control the color of emitted light according to particle size, and thus, quantum dots can have various suitable emission colors, such as blue, red, and green.

[0370] Electron transport region in the organic layer 150

[0371] The electron transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0372] The electron transport region may include at least one layer 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 the present disclosure are not limited thereto.

[0373] 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 for each structure, the constituent layers are stacked sequentially from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.

[0374] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing ring.

[0375] As used herein, the term "π-electron deficient nitrogen-containing ring" refers to a C-type ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.

[0376] For example, the “π-electron-deficient nitrogen-containing ring” may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion are fused to each other (e.g., combined with each other), or iii) a heteropolycyclic group in which at least one 5- to 7-membered heteromonocyclic group each having at least one *-N=*' portion is fused to at least one C 5 -C 60 A carbocyclic group is a fused heteropolycyclic group.

[0377] Examples of π-electron-deficient nitrogen-containing rings are imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole, but embodiments of the present disclosure are not limited thereto.

[0378] For example, the electron transport region may include a compound represented by the following Formula 601:

[0379] Formula 601

[0380] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0381] Wherein, in Formula 601,

[0382] Ar 601 Can be substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0383] xe11 can be 1, 2 or 3,

[0384] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0385] xe1 may be an integer selected from 0 to 5,

[0386] R 601 Can be selected from substituted or unsubstituted C3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0387] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0388] xe21 may be an integer selected from 1-5.

[0389] In an embodiment, the amount of Ar is xe11 601 and the number of R is xe21 601 At least one of the may include a π-electron deficient nitrogen-containing ring.

[0390] In an embodiment, Ar in Formula 601 601 You can choose from:

[0391] Phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl oxazolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0392] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, naphthacene, pyrenyl, peryl, pentaphenanthracenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purine quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -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 ),

[0393] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0394] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond.

[0395] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.

[0396] In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0397] Formula 601-1

[0398]

[0399] Among them, in formula 601-1,

[0400] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and selected from X 614 To X 616 At least one of may be N,

[0401] L 611 To L 613 Can be combined with L independently 601 Same as described,

[0402] xe611 to xe613 can each independently be the same as described in conjunction with xe1,

[0403] R 611 To R 613 Can be independently combined with R 601 Same as described, and

[0404] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0405] In an embodiment, L in Formulas 601 and 601-1 601 and L 611 To L 613 Can be independently selected from:

[0406] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0407] each substituted with at least one selected from the following: phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl , pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,

[0408] However, the embodiments of the present disclosure are not limited thereto.

[0409] In one or more embodiments, xe1 and xe611 to xe613 in Formulas 601 and 601-1 may each independently be 0, 1 or 2.

[0410] In one or more embodiments, R in Formula 601 and 601-1 601 and R 611 To R 613 Can be independently selected from:

[0411] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl;

[0412] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl oxazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0413] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0414] Where Q 601 and Q 602 Same as described above.

[0415] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

[0416]

[0417]

[0418]

[0419] In one or more embodiments, the electron transport region may include a plurality of selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ.

[0420]

[0421] The thickness of the buffer layer, the hole blocking layer, and the electron control layer can each be independently about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within any of the aforementioned ranges, excellent hole blocking characteristics and / or excellent electron control characteristics may be obtained without a significant increase in driving voltage.

[0422] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within any of the above ranges, the electron transport layer may have appropriate or satisfactory electron transport characteristics without a significant increase in driving voltage.

[0423] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal element-containing material in addition to the above-mentioned materials.

[0424] The metal element-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the alkaline earth metal complex may include a metal ion selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

[0425] For example, the metal element-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2:

[0426]

[0427] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

[0428] The electron injection layer may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0429] 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.

[0430] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an embodiment, 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.

[0431] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.

[0432] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0433] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides and / or iodides) of alkali metals, alkaline earth metals and rare earth metals.

[0434] The alkali metal compound can be selected from alkali metal oxides, such as Li2 O, Cs 2 O and K 2 O, and an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI. In an embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0435] 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) and Ba x Ca 1-x O(0 < x < 1). In an embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0436] The rare earth metal compound may be selected from YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 . In an embodiment, the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.

[0437] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0438] The electron injection layer may include (or be composed 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 further include an organic material. When the electron injection layer further includes an organic material, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.

[0439] The thickness of the electron injection layer can be about to about or, for example, about to about When the thickness of the electron injection layer is within any of the above ranges, the electron injection layer may have appropriate or satisfactory electron injection characteristics without a significant increase in driving voltage.

[0440] The second electrode 190

[0441] The second electrode 190 is on the organic layer 150 having such a structure. The second electrode 190 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals having relatively low functional properties, alloys, conductive compounds, and combinations thereof.

[0442] 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), silver-magnesium (Ag-Mg), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0443] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0444] Figures 2 to 4 Description

[0445] Figure 2 The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in the order of the statement, Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the order of the statement, and Figure 4The organic light-emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the order of the statements.

[0446] about Figures 2 to 4 , the first electrode 110, the organic layer 150 and the second electrode 190 can be combined by reference Figure 1 Description presented to understand.

[0447] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer can pass through the first electrode 110 (which is a semi-transmissive electrode or a transmissive electrode) and the first capping layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer can pass through the second electrode 190 (which is a semi-transmissive electrode or a transmissive electrode) and the second capping layer 220 toward the outside.

[0448] According to the principle of constructive interference, the first capping layer 210 and the second capping layer 220 may increase external light emitting efficiency.

[0449] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

[0450] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. Carbocyclic compounds and amine compounds may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In an embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0451] In an embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0452] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.

[0453]

[0454] In the above, combined Figures 1 to 4The organic light emitting device according to the embodiment is described. However, the embodiments of the present disclosure are not limited thereto.

[0455] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a specific region by using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.

[0456] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. to about Deposition is carried out at a deposition rate of .

[0457] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to 200°C by considering the materials to be contained in the layers to be formed and the structure of the layers to be formed.

[0458] General definition of at least some substituents

[0459] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, preferably C 1 -C 20 Alkyl or C 1 -C 10 The term "C alkyl" as used herein refers to an alkyl group, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has a divalent group having substantially the same structure.

[0460] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., the middle) or the terminal (e.g., the end), and examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C 60"Alkenylene" refers to C 2 -C 60 An alkenyl group has a divalent group having substantially the same structure.

[0461] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., the middle) or the terminal (e.g., the end), and examples thereof include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups have substantially the same structure as divalent groups.

[0462] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 The monovalent group represented by 101 C 1 -C 60 Alkyl), preferably C 1 -C 20 Alkoxy or C 1 -C 10 An alkoxy group, and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0463] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0464] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.

[0465] As used herein, the term "C 3 -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 having no aromaticity (e.g., not aromatic), and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group is a divalent group having substantially the same structure.

[0466] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.

[0467] As used herein, the term "C 6 -C 60 "Aryl" is a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms). 6 -C 60 Examples of aryl groups include fluorenyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl and 1,2-triphenylenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other (eg, bonded together).

[0468] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. As used herein, the term "C 1 -C 60The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system which, in addition to 1 to 60 carbon atoms, has at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 60 Examples of heteroaryl groups include carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, and isoquinolyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other (eg, bonded to each other).

[0469] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 aryl).

[0470] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other (e.g., bound together to each other), only carbon atoms as ring-forming atoms, and no aromaticity (e.g., not aromatic) in its entire molecular structure. An example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.

[0471] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure. An example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0472] As used herein, the term "C 5 -C 60A "carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon as ring atoms and includes (or consists of) 5 to 60 carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group may be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). 5 -C 60 The number of substituents attached to the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0473] As used herein, the term "C 1 -C 60 "Heterocyclic group" refers to a C 5 -C 60 The carbocyclic group has substantially the same structure except that at least one heteroatom selected from N, O, Si, P and S other than carbon (the number of carbon atoms may range from 1 to 60) is used as a ring-forming atom.

[0474] In this specification, substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0475] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0476] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q13 )、-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 );

[0477] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0478] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 );as well as

[0479] -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 ),

[0480] Where Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.

[0481] As used herein, the term "Ph" refers to phenyl, as used herein, the term "Me" refers to methyl, as used herein, the term "Et" refers to ethyl, as used herein, the term "tert-Bu" or "Bu t ” refers to tert-butyl, and the term “OMe” as used herein refers to methoxy.

[0482] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In other words, a "biphenyl group" is a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0483] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". In other words, a "terphenyl group" is a group having a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0484] Unless otherwise defined, *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula.

[0485] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in detail with reference to Synthesis Examples and Examples. The phrase "replacing A with B" used in describing Synthesis Examples means replacing A with an equal molar equivalent of B.

[0486] Example

[0487] Intermediate 1: Synthesis of C(1)

[0488]

[0489] Synthesis of C(1)-1: (phenyl-d5)boronic acid (1 eq, 1.27 g), 4-iodo-1,1'-biphenyl (1 eq, 2.8 g), Pd(PPh 3 ) 4 (0.05eq, 0.56g), K 2 CO 3 (3 eq, 4.14 g), 20 ml of tetrahydrofuran (THF) and 5 ml of H 2 O was added to a single-necked flask and stirred at 80° C. for 6 hours. The resulting reaction product was washed with ethyl acetate (EA) / H 2 O treatment and separation using column chromatography (dichloromethane (MC) / hexane (Hx) = 1 / 50) to obtain 1.88 g of the resulting compound (C(1)-1) (yield = 80%, purity = 99%).

[0490] Synthesis of C(1): C(1)-1 (1 eq, 1.88 g), N-bromosuccinimide (NBS) (2.2 eq, 3.1 g) and 20 ml of MC were added to a single-necked flask and stirred at 30° C. for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 100) to obtain 2.8 g of the resulting compound (C(1)) (yield=90%, purity=98%).

[0491] Intermediate 2: Synthesis of C(2)

[0492]

[0493] Synthesis of C(2)-1: 1,4-dibromobenzene-2,3,5,6-d4 (1 eq, 2.4 g), phenylboronic acid (2.2 eq, 2.7 g), Pd(PPh 3 ) 4 (0.05eq, 0.56g), K 2 CO 3 (3 eq, 4.14 g), 20 ml of THF and 5 ml of H 2 O was added to a single-necked flask and stirred at 80°C for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 50) to obtain 1.87 g of the resulting compound (C(2)-1) (yield=78%, purity=99%).

[0494] Synthesis of C(2): C(2)-1 (1 eq, 1.87 g), NBS (2.2 eq, 3.05 g) and 20 ml of MC were added to a single-necked flask and stirred at 30° C. for 6 hours. The resulting reaction product was treated with EA / H 2O treatment and separation using column chromatography (MC / Hx=1 / 100) to obtain 2.8 g of compound (C(2)) (yield=90%, purity=98%).

[0495] Intermediate 3: Synthesis of C(3)

[0496]

[0497] Synthesis of C(3)-1: Phenylboronic acid (1 eq, 1.21 g), 4-iodo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (1 eq, 2.89 g), Pd(PPh 3 ) 4 (0.05eq, 0.56g), K 2 CO 3 (3 eq, 4.14 g), 20 ml of THF and 5 ml of H 2 O was added to a single-necked flask and stirred at 80°C for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 50) to obtain 1.91 g of the resulting compound (C(3)-1) (yield=80%, purity=99%).

[0498] Synthesis of C(3): C(3)-1 (1 eq, 1.91 g), NBS (2.2 eq, 3.1 g) and 20 ml of MC were added to a single-necked flask and stirred at 30° C. for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 100) to obtain 2.78 g of the resulting compound (C(3)) (yield=88%, purity=98%).

[0499] Intermediate 4: Synthesis of C(4)

[0500]

[0501] Synthesis of C(4)-1: 1,4-dibromobenzene (1 eq, 2.36 g), (phenyl-d5)boronic acid (2.2 eq, 2.8 g), Pd(PPh 3 ) 4 (0.05eq, 0.56g), K 2 CO 3 (3 eq, 4.14 g), 20 ml of THF and 5 ml of H 2 O was added to a single-necked flask and stirred at 80°C for 6 hours. The resulting reaction product was treated with EA / H 2O treatment and separation using column chromatography (MC / Hx=1 / 50) to obtain 2.1 g of the resulting compound (C(4)-1) (yield=88%, purity=99%).

[0502] Synthesis of C(4): C(4)-1 (1 eq, 2.1 g), NBS (2.2 eq, 3.45 g) and 20 ml of MC were added to a single-necked flask and stirred at 30° C. for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 100) to obtain 3.13 g of the resulting compound (C(4)) (yield=90%, purity=99%).

[0503] Intermediate 5: Synthesis of C(5)

[0504]

[0505] Synthesis of C(5)-1: (phenyl-d5)boronic acid (1 eq, 1.27 g), 4-iodo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (1 eq, 2.89 g), Pd(PPh 3 ) 4 (0.05eq, 0.56g), K 2 CO 3 (3 eq, 4.14 g), 20 ml of THF and 5 ml of H 2 O was added to a single-necked flask and stirred at 80°C for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 50) to obtain 1.88 g of the resulting compound (C(5)-1) (yield=80%, purity=99%).

[0506] Synthesis of C(5): C(1)-1 (1 eq, 1.88 g), NBS (2.2 eq, 3.1 g) and 20 ml of MC were added to a single-necked flask and stirred at 30° C. for 6 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 100) to obtain 2.67 g of the resulting compound (C(5)) (yield=86%, purity=98%).

[0507] Synthesis Example 1: Synthesis of Compound 1

[0508]

[0509] Intermediate C(1) (1 eq, 3.92 g), diphenylamine (DPA) (2.2 eq, 3.72 g), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba)3 )(0.05eq, 0.46g), t-BuONa (3eq, 2.88g), t-Bu 3 P (0.1 eq, 0.11 ml) and 100 ml of toluene (Tol.) were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 4.08g of the obtained compound (Compound 1) (yield=72%, purity=96%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.5% or higher, it was subjected to sublimation purification. Obtained 3.5g of the obtained compound (purity ≥99.9%).

[0510] Synthesis Example 2: Synthesis of Compound 2

[0511]

[0512] Synthesis of 2-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (2-P1) (yield=70%, purity=99%).

[0513] Synthesis of compound 2: 2-P1 (1 eq, 3.36 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.71 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtain 3.7g of the resulting compound (Compound 2) (yield=82%, purity=98%). The purity of the resulting product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. Obtain 3.3g of the resulting compound (purity ≥99.9%).

[0514] Synthesis Example 3: Synthesis of Compound 5

[0515]

[0516] Synthesis of 5-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (5-P1) (yield=70%, purity=99%).

[0517] Synthesis of compound 5: 5-P1 (1 eq, 3.36 g), 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (1 eq, 1.99 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5). 3.4 g of the resulting compound (Compound 5) was obtained (yield=75%, purity=98%). The purity of the resulting product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3 g of the resulting compound (purity ≥99.9%) was obtained.

[0518] Synthesis Example 4: Synthesis of Compound 11

[0519]

[0520] Synthesis of 11-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (11-P1) (yield=70%, purity=99%).

[0521] Synthesis of compound 11: 11-P1 (1 eq, 3.36 g), N,9-diphenyl-9H-carbazole-3-amine (1 eq, 2.34 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 2.86 g of the obtained compound (Compound 11) was obtained (yield=63%, purity=98%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 2.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0522] Synthesis Example 5: Synthesis of Compound 14

[0523]

[0524] Synthesis of 14-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (14-P1) (yield=70%, purity=99%).

[0525] Synthesis of compound 14: 14-P1 (1 eq, 3.36 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.7 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.58 g of the obtained compound (Compound 14) was obtained (yield=79%, purity=97%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.3 g of the obtained compound (purity ≥99.9%) was obtained.

[0526] Synthesis Example 6: Synthesis of Compound 16

[0527]

[0528] Synthesis of 16-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (16-P1) (yield=70%, purity=99%).

[0529] Synthesis of compound 16: 16-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 16) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0530] Synthesis Example 7: Synthesis of Compound 17

[0531]

[0532] Synthesis of 17-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (17-P1) (yield=70%, purity=99%).

[0533] Synthesis of compound 17: 17-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 3.76g of the obtained compound (Compound 17) (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. Obtained 3.5g of the obtained compound (purity ≥99.9%).

[0534] Synthesis Example 8: Synthesis of Compound 19

[0535]

[0536] Synthesis of 19-P1: Intermediate C(1) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (19-P1) (yield=70%, purity=99%).

[0537] Synthesis of compound 19: 19-P1 (1 eq, 3.36 g), 2-(naphthalen-1-yl)-N-phenylaniline (1 eq, 2.06 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 3.62g of the obtained compound (Compound 19) (yield=80%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. Obtained 3.42g of the obtained compound (purity ≥99.9%).

[0538] Synthesis Example 9: Synthesis of Compound 25

[0539]

[0540] Intermediate C (2) (1 eq, 3.92 g), DPA (2.2 eq, 3.72 g), Pd 2 (dba) 3 (0.05eq, 0.46g), t-BuONa (3eq, 2.88g), t-Bu 3 P (0.1 eq, 0.11 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtain 4.25g of the resulting compound (Compound 25) (yield=75%, purity=98%). The purity of the resulting product was increased by recrystallization through ether. When the purity reached 99.7% or higher, it was subjected to sublimation purification. Obtain 4g of the resulting compound (purity ≥99.9%).

[0541] Synthesis Example 10: Synthesis of Compound 26

[0542]

[0543] Synthesis of 26-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.84 g of the resulting compound (26-P1) (yield=80%, purity=99%).

[0544] Synthesis of compound 26: 26-P1 (1 eq, 3.84 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.23 g of the obtained compound (Compound 26) was obtained (yield=82%, purity=98%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.6% or higher, it was subjected to sublimation purification. 3.9 g of the obtained compound (purity ≥99.9%) was obtained.

[0545] Synthesis Example 11: Synthesis of Compound 29

[0546]

[0547] Synthesis of 29-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.84 g of the resulting compound (29-P1) (yield=80%, purity=99%).

[0548] Synthesis of compound 29: 29-P1 (1 eq, 3.84 g), 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (1 eq, 2.28 g), Pd 2 (dba) 3(0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.13 g of the obtained compound (Compound 29) was obtained (yield=80%, purity=98%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.6% or higher, it was subjected to sublimation purification. 3.7 g of the obtained compound (purity ≥99.9%) was obtained.

[0549] Synthesis Example 12: Synthesis of Compound 38

[0550]

[0551] Synthesis of 38-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.84 g of the resulting compound (38-P1) (yield=80%, purity=99%).

[0552] Synthesis of compound 38: 38-P1 (1 eq, 3.84 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.97g of the obtained compound (Compound 38) was obtained (yield=77%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.6% or higher, it was subjected to sublimation purification. 3.65g of the obtained compound (purity ≥99.9%) was obtained.

[0553] Synthesis Example 13: Synthesis of Compound 40

[0554]

[0555] Synthesis of 40-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (40-P1) (yield=70%, purity=99%).

[0556] Synthesis of compound 40: 40-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 40) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0557] Synthesis Example 14: Synthesis of Compound 41

[0558]

[0559] Synthesis of 41-P1: Intermediate C(2) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (41-P1) (yield=70%, purity=99%).

[0560] Synthesis of compound 41: 41-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 41) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0561] Synthesis Example 15: Synthesis of Compound 49

[0562]

[0563] Intermediate C (3) (1 eq, 3.96 g), DPA (2.2 eq, 3.72 g), Pd 2 (dba) 3 (0.05eq, 0.46g), t-BuONa (3eq, 2.88g), t-Bu 3 P (0.1 eq, 0.11 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 4.34g of the obtained compound (Compound 49) (yield=76%, purity=98%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.7% or higher, it was subjected to sublimation purification. Obtained 4.1g of the obtained compound (purity ≥99.9%).

[0564] Synthesis Example 16: Synthesis of Compound 50

[0565]

[0566] Synthesis of 50-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (50-P1) (yield=80%, purity=99%).

[0567] Synthesis of compound 50: 50-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 4g of the obtained compound (Compound 50) (yield=77%, purity=98.5%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.7% or higher, it was subjected to sublimation purification. Obtained 3.6g of the obtained compound (purity ≥99.9%).

[0568] Synthesis Example 17: Synthesis of Compound 53

[0569]

[0570] Synthesis of 53-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (53-P1) (yield=80%, purity=99%).

[0571] Synthesis of compound 53: 53-P1 (1 eq, 3.87 g), 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (1 eq, 2.28 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.2 g of the obtained compound (Compound 53) was obtained (yield=81%, purity=98.9%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.7% or higher, it was subjected to sublimation purification. 3.8 g of the obtained compound (purity ≥99.9%) was obtained.

[0572] Synthesis Example 18: Synthesis of Compound 62

[0573]

[0574] Synthesis of 62-P1: Intermediate C(3) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (62-P1) (yield=80%, purity=99%).

[0575] Synthesis of compound 62: 62-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2O treatment and separation using column chromatography (MC / Hx=1 / 5). Obtain 4 g of the resulting compound (Compound 62) (yield=77%, purity=99%). The purity of the resulting product was increased by recrystallization through ether. When the purity reached 99.88% or higher, it was subjected to sublimation purification. Obtain 3.6 g of the resulting compound (purity ≥99.9%).

[0576] Synthesis Example 19: Synthesis of Compound 64

[0577]

[0578] Synthesis of 64-P1: Intermediate C(3) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (64-P1) (yield=70%, purity=99%).

[0579] Synthesis of compound 64: 64-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 64) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0580] Synthesis Example 20: Synthesis of Compound 65

[0581]

[0582] Synthesis of 65-P1: Intermediate C(3) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2(dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (65-P1) (yield=70%, purity=99%).

[0583] Synthesis of compound 65: 65-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 65) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0584] Synthesis Example 21: Synthesis of Compound 73

[0585]

[0586] Intermediate C (4) (1 eq, 3.96 g), DPA (2.2 eq, 3.72 g), Pd 2 (dba) 3 (0.05eq, 0.46g), t-BuONa (3eq, 2.88g), t-Bu 3 P (0.1 eq, 0.11 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 4g of the obtained compound (Compound 73) (yield=70%, purity=99.2%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.65% or higher, it was subjected to sublimation purification. Obtained 3.7g of the obtained compound (purity ≥99.9%).

[0587] Synthesis Example 22: Synthesis of Compound 74

[0588]

[0589] Synthesis of 74-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (74-P1) (yield=80%, purity=99%).

[0590] Synthesis of compound 74: 74-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-4-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.36 g of the obtained compound (Compound 74) was obtained (yield=84%, purity=97%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.5% or higher, it was subjected to sublimation purification. 4.1 g of the obtained compound (purity ≥99.9%) was obtained.

[0591] Synthesis Example 23: Synthesis of Compound 77

[0592]

[0593] Synthesis of 77-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (77-P1) (yield=80%, purity=99%).

[0594] Synthesis of compound 77: 77-P1 (1 eq, 3.87 g), 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (1 eq, 2.28 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.2 g of the obtained compound (Compound 77) was obtained (yield=81%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.85 g of the obtained compound (purity ≥99.9%) was obtained.

[0595] Synthesis Example 24: Synthesis of Compound 86

[0596]

[0597] Synthesis of 86-P1: Intermediate C(4) (1 eq, 3.96 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.87 g of the resulting compound (86-P1) (yield=80%, purity=99%).

[0598] Synthesis of compound 86: 86-P1 (1 eq, 3.87 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 1.95 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). Obtained 4.36g of the obtained compound (Compound 86) (yield=84%, purity=98.1%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99% or higher, it was subjected to sublimation purification. Obtained 4g of the obtained compound (purity ≥99.9%).

[0599] Synthesis Example 25: Synthesis of Compound 88

[0600]

[0601] Synthesis of 88-P1: Intermediate C(4) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (88-P1) (yield=70%, purity=99%).

[0602] Synthesis of compound 88: 88-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 3.76 g of the obtained compound (Compound 88) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0603] Synthesis Example 26: Synthesis of Compound 89

[0604]

[0605] Synthesis of 89-P1: Intermediate C(4) (1 eq, 3.92 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 3.36 g of the resulting compound (89-P1) (yield=70%, purity=99%).

[0606] Synthesis of compound 89: 89-P1 (1 eq, 3.36 g), N-phenylnaphthalene-1-amine (1 eq, 1.53 g), Pd 2 (dba) 3 (0.03eq, 0.189g), t-BuONa (1.5eq, 1g), t-Bu 3 P (0.05 eq, 0.04 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5). 3.76 g of the obtained compound (89) was obtained (yield=83%, purity=99%). The purity of the obtained product was increased by recrystallization through diethyl ether. When the purity reached 99.8% or higher, it was subjected to sublimation purification. 3.5 g of the obtained compound (purity ≥99.9%) was obtained.

[0607] Synthesis Example 27: Synthesis of Compound 97

[0608]

[0609] Intermediate C (5) (1 eq, 4 g), DPA (2.2 eq, 3.72 g), Pd 2 (dba) 3 (0.05eq, 0.46g), t-BuONa (3eq, 2.88g), t-Bu 3 P (0.1 eq, 0.11 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2O treatment and column chromatography separation (MC / Hx=1 / 5). 5 g of the obtained compound (Compound 97) was obtained (yield=88%, purity=99%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.9% or higher, it was subjected to sublimation purification. 4..66 g of the obtained compound (purity ≥99.9%) was obtained.

[0610] Synthesis Example 28: Synthesis of Compound 110

[0611]

[0612] Synthesis of 110-P1: Intermediate C(5) (1 eq, 4 g), DPA (1 eq, 1.69 g), Pd 2 (dba) 3 (0.03eq, 0.27g), t-BuONa (1.5eq, 1.44g), t-Bu 3 P (0.05 eq, 0.06 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and separation using column chromatography (MC / Hx=1 / 5) to obtain 4.15 g of the resulting compound (110-P1) (yield=85%, purity=97%).

[0613] Synthesis of compound 110: 110-P1 (1 eq, 4.15 g), N-phenyl-[1,1'-biphenyl]-2-amine (1 eq, 2.08 g), Pd 2 (dba) 3 (0.03eq, 0.216g), t-BuONa (1.5eq, 1.14g), t-Bu 3 P (0.05 eq, 0.046 ml) and 100 ml of Tol. were added to a single-necked flask and stirred at 100° C. for 2 hours. The resulting reaction product was treated with EA / H 2 O treatment and column chromatography separation (MC / Hx=1 / 5). 4.37 g of the obtained compound (Compound 110) was obtained (yield=79%, purity=98.8%). The purity of the obtained product was increased by recrystallization through ether. When the purity reached 99.7% or higher, it was subjected to sublimation purification. 4 g of the obtained compound (purity ≥99.9%) was obtained.

[0614] The compounds synthesized according to Synthesis Examples 1 to 28 1 H NMR and MS / FAB are shown in Table 1 below.

[0615] Those skilled in the art can easily identify even compounds other than those shown in Table 1 by referring to the above-described synthetic routes and source materials.

[0616] Table 1

[0617]

[0618]

[0619] Comparative Example 1

[0620] As the anode, the The glass substrate was cut into a size of 50 mm x 50 mm x 0.7 mm, ultrasonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.

[0621] On a glass substrate, 2-TNATA was first vacuum deposited to form a layer with a thickness of The hole injection layer is formed by vacuum depositing 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) as a hole transport material to form a hole injection layer with a thickness of hole transport layer.

[0622] 9,10-di(2-naphthyl)anthracene (ADN) as a blue fluorescent host and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter, referred to as DPAVBi) as a blue phosphorescent dopant compound were co-deposited on the hole transport layer at a weight ratio of 98:2 to form a film with a thickness of 1000 nm. The emission layer.

[0623]

[0624] Then, Alq 3 Deposited on the emitter layer to form a thickness of Then, LiF as an alkali metal halide is deposited on the electron transport layer to form a layer with a thickness of The electron injection layer is formed by vacuum depositing Al on it to form a layer with a thickness of An Al electrode (cathode) is formed to form a LiF / Al electrode, thereby completing the manufacture of an organic light-emitting device.

[0625] Examples 1 to 28

[0626] An organic light-emitting device was manufactured in substantially the same manner as in Comparative Example 1, except that the compounds shown in Table 2 were respectively used instead of NPB in forming the hole transport layer.

[0627] Comparative Examples 2 to 7

[0628] An organic light-emitting device was manufactured in substantially the same manner as in Comparative Example 1, except that Compounds A to F were respectively used instead of NPB in forming a hole transport layer.

[0629]

[0630] Evaluation Example 1

[0631] The driving voltage, current density, brightness, efficiency, emission color, and half-life of the organic light-emitting devices manufactured according to Examples 1 to 28 and Comparative Examples 1 to 7 were measured at 600 nits by using Keithley SMU 236 and a brightness photometer PR650, and the results are shown in Table 2.

[0632] Table 2

[0633]

[0634]

[0635] It can be seen from Table 2 that the organic light-emitting devices of Examples 1 to 28 have lower driving voltages and higher efficiencies than the organic light-emitting devices of Comparative Examples 1 to 7. In addition, it can be seen that the organic light-emitting devices of Examples 1 to 28 exhibit high brightness and long lifespan compared to the organic light-emitting devices of Comparative Examples 1 to 7.

[0636] An organic light-emitting device including an amine compound according to an embodiment of the present disclosure may have low driving voltage, high brightness, high efficiency, and a long lifespan.

[0637] It should be understood that the embodiments described herein should be considered as descriptive only and not for the purpose of limitation. The description of the features or aspects in each embodiment should generally be considered as being applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the present disclosure as defined by the appended claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as An organic layer between the first electrode and the second electrode and including an emission layer; and The organic light-emitting device includes at least one amine compound represented by Formula 1: Formula 1 Among them, L1 to L4, L 11 and L 12 are each independently substituted or unsubstituted C5-C 60 Carbocyclic group, or substituted or unsubstituted C1-C 60 Heterocyclic groups, a1 to a4, a11 and a12 are each independently an integer selected from 0 to 5, Ar1 to Ar4 are each independently substituted or unsubstituted C5-C 60 Carbocyclic group, or substituted or unsubstituted C1-C 60 Heterocyclic groups, Ar1 to Ar4 each do not include an amine group, R1 to R3 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), D1 to D3 are each deuterium, b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4, The sum of b1 and c1, the sum of b2 and c2, and the sum of b3 and c3 are each 4, One of c1 to c3 is 4 and the other two are each 0, Two of c1 to c3 are each 4 and the other one is 0, or c1 to c3 are 4 each, In formula 1, The part represented by is a group represented by formula 2-1: Formula 2-1 Wherein, in Formula 2-1, * and *' each indicate a binding site with an adjacent atom, and the substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 ); C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each of the following C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 ); as well as -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 ), Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.

2. The organic light-emitting device according to claim 1, wherein the first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof. 3 . The organic light-emitting device of claim 2 , wherein the at least one amine compound represented by Formula 1 is included in the hole transport region. 4 . The organic light-emitting device of claim 3 , wherein the hole transport region includes the hole transport layer, and the at least one amine compound represented by Formula 1 is included in the hole transport layer. 5 . The organic light-emitting device of claim 4 , wherein the hole transport region further comprises a p-dopant having a lowest unoccupied molecular orbital energy level of −3.5 eV or less.

6. The organic light emitting device as claimed in claim 3, wherein the emission layer comprises a host and a dopant, and The dopant includes a fluorescent dopant including a styrene-based compound.

7. The organic light emitting device as claimed in claim 3, wherein the emission layer comprises a host and a dopant, and The dopant includes a phosphorescent dopant.

8. The organic light-emitting device of claim 2, wherein the electron transport region comprises 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.

9. An amine compound represented by Formula 1: Formula 1 Among them, L1 to L4, L 11 and L 12 are each independently substituted or unsubstituted C5-C 60 Carbocyclic group, or substituted or unsubstituted C1-C 60 Heterocyclic groups, a1 to a4, a11 and a12 are each independently an integer selected from 0 to 5, Ar1 to Ar4 are each independently substituted or unsubstituted C5-C 60 Carbocyclic group, or substituted or unsubstituted C1-C 60 Heterocyclic groups, Ar1 to Ar4 each do not include an amine group, R1 to R3 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), D1 to D3 are each deuterium, b1 to b3 and c1 to c3 are each independently an integer selected from 0 to 4, The sum of b1 and c1, the sum of b2 and c2, and the sum of b3 and c3 are each 4, One of c1 to c3 is 4 and the other two are each 0, Two of c1 to c3 are each 4 and the other one is 0, or c1 to c3 are 4 each, In formula 1, The part represented by is a group represented by formula 2-1: Formula 2-1 in, In Formula 2-1, * and *' each indicate a binding site with an adjacent atom, and The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 ); C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each of the following C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 ),as well as -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 ), Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.

10. The amine compound according to claim 9, wherein L1 to L4, L 11 and L 12 Each independently selected from: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, spiro-fluorenylene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenanthrenylene, hexaphenylene, pentaphenylene, rubenylene, coronenylene, ovophenylene, and carbazolylene; and phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, spiro-fluorene-benzofluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubenylene, coroneylene, ovopheneylene and carbazolylene, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenylene, pyrenyl, peryl, pentaphenanthrenyl, hexaphenylene, pentacene, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazine , pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, dibenzothioxyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Where Q 31 To Q 33 Each independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, C1-C 10 Alkyl-substituted phenyl, biphenyl, terphenyl and naphthyl. The amine compound according to claim 9 , wherein a11 and a12 are each 0.

12. The amine compound of claim 9, wherein Ar1 to Ar4 are each independently selected from: phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolyl, isoquinolyl, benzoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothienyl, biphenyl and terphenyl; and phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirol, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolyl, isoquinolyl phenyl, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, benzonaphthofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl , acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, dibenzothirolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirolyl, biphenyl and terphenyl.

13. The amine compound according to claim 9, wherein Ar1 to Ar4 are each independently a group represented by one of Formulae 5-1 to 5-27: in, In formulas 5-1 to 5-27, Y 31 is O, S, C(Z 35 )(Z 36 ) or Si(Z 37 )(Z 38 ); Z 31 To Z 38 Each is independently any one of the following: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; e3 is an integer selected from 0 to 3, e4 is an integer selected from 0 to 4, e5 is an integer selected from 0 to 5, e6 is an integer selected from 0 to 6, e7 is an integer selected from 0 to 7, e9 is an integer selected from 0 to 9, and *Indicates the binding site with the neighboring atoms. 14 . The amine compound of claim 9 , wherein each of Ar1 to Ar4 does not include the amine group.

15. The amine compound of claim 9, wherein R1 to R3 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, biphenyl and terphenyl; and Each of which is substituted by at least one of the following: methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl.

16. The amine compound as claimed in claim 9, wherein at least one of R1 to R3 is hydrogen.

17. The amine compound as claimed in claim 9, wherein the sum of c1, c2 and c3 is 4 or more.

18. The amine compound of claim 9, wherein the amine compound represented by Formula 1 is selected from Compounds 1 to 192:

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