Heterocyclic compounds and organic light emitting devices comprising the same

Abstract

Provided are a heterocyclic 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 heterocyclic compound represented by Formula 1.

Description

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2020-0056662, filed on May 12, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more embodiments of this disclosure relate to a heterocyclic compound and an organic light-emitting device comprising the heterocyclic compound. Background Technology

[0003] Compared to other devices in the field, organic light-emitting devices (OLEDs) are self-emitting devices with wide viewing angles, high contrast, short response times, and excellent properties in terms of brightness, driving voltage, and response speed, and produce full-color images.

[0004] In this example, an OLED may include a first electrode located on a substrate and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers such as holes and electrons recombine in the emitter layer to generate excitons. These excitons transition (or relax) from excited states to the ground state, thereby producing light. Summary of the Invention

[0005] One or more embodiments provide a heterocyclic compound and an organic light-emitting device comprising the heterocyclic compound.

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

[0007] One aspect of the embodiments of this disclosure provides a heterocyclic compound represented by Formula 1:

[0008] Formula 1

[0009]

[0010] In Equation 1,

[0011] Both CY1 and CY2 are independently selected from C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) and C1-C 60 Heterocyclic group,

[0012] L1 is selected from C5-C that are either unsubstituted or substituted with at least one R3. 60 Carbocyclic group (or C4-C)60 (Carbocyclic group) and C1-C 60 Heterocyclic group,

[0013] B1 is a group represented by Formula 2.

[0014] n1 is an integer from 1 to 5.

[0015] Formula 2

[0016]

[0017] In Equation 2,

[0018] Ar1 is selected from those that are not substituted or have at least one R substituted. 103 C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) and C1-C 60 Heterocyclic groups, wherein Ar1 does not include triazine.

[0019] R1 to R3 and R 101 To R 103 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, substituted or unsubstituted C1-C groups. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), wherein R 103 Excluding triazine,

[0020] b1 and b2 are both independent integers from 0 to 10.

[0021] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent in the group consisting of a heteroaryl group, a substituted monovalent nonaromatic condensed polycyclic group, and a substituted monovalent nonaromatic condensed heterocyclic group is selected from:

[0022] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy

[0023] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C60 alkynyl and C1-C 60 Alkoxy

[0024] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0025] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, biphenyl, terphenyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl; and

[0026] -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 ),

[0027] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, substituted with C1-C 60 C6-C of alkyl groups 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl, and

[0028] * indicates a bonding site with an adjacent atom.

[0029] Another aspect of the embodiments of this disclosure provides an organic light-emitting device, the organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emitting layer, wherein the organic light-emitting device comprises at least one heterocyclic compound represented by Formula 1. Attached Figure Description

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

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

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

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

[0034] Figure 4 This is a schematic cross-sectional view of an organic light-emitting device according to another embodiment. Detailed Implementation

[0035] Referring now to certain embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always denote the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to explain aspects of the embodiments described herein. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression “at least one of a, b, and c” may refer to 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] Because the subject matter of this disclosure can be varied and can have various examples, some examples will be shown in the accompanying drawings and described in more detail in the specific embodiments. The effects and features of the subject matter of this disclosure, as well as methods for implementing them, will be illustrated by referring to the examples described in more detail herein with reference to the accompanying drawings. However, the subject matter of this disclosure is not limited to the examples disclosed below and can be implemented in various forms.

[0037] In the following description, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. Identical or corresponding components will be indicated by the same reference numerals, and therefore their redundant descriptions will not be repeated herein.

[0038] As used herein, unless the context clearly indicates otherwise, the singular forms “a,” “one,” and “the” are also intended to include the plural forms.

[0039] It will also be understood that the terms “comprising” and / or “including” as used herein indicate the presence of the stated feature or component, but do not exclude the presence or addition of one or more other features or components.

[0040] It will be understood that when a layer, region, or component is referred to as being "on" or "to" another layer, region, or component, that layer, region, or component may be formed directly or indirectly on said other layer, region, or component. That is, for example, intermediate layers, regions, or components may or may not exist.

[0041] For ease of illustration, the dimensions of the elements in the accompanying drawings may be exaggerated. In other words, since the dimensions and thicknesses of the components in the drawings are arbitrarily shown for ease of illustration, the following embodiments of this disclosure are not limited thereto.

[0042] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first and second electrodes of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0043] The expression “(organic layer) includes compounds represented by Formula 1” as used herein can include cases where “(organic layer) includes one compound of Formula 1 or two or more different compounds of Formula 1”.

[0044] In the following, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings.

[0045] One aspect of the embodiments of this disclosure provides heterocyclic compounds represented by Formula 1:

[0046] Formula 1

[0047]

[0048] In Equation 1, CY1 and CY2 can both be independently selected from C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) and C1-C 60 Heterocyclic group (or C1-C) 30 Heterocyclic group).

[0049] In the embodiments, CY1 and CY2 can both be independently selected from phenyl groups, indene groups, naphthyl groups, anthracene groups, fluorene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, etc. Groups, tetraphenyl group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, indole group, isoindole group, indazole group, quinoline group, isoquinoline group, benzoquinoline group, naphthidine group, quinoxaline group, quinazoline group, cycloline group, carbazole group, phenanthridine group, acridine group, phenanthridine group, phenazine group, phenazine group, benzimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxazole group, triazole group, oxadiazole group, triazine group, benzooxazole group, dibenzofuran group, dibenzothiophene group, benzocarbazole group and dibenzocarbazole group.

[0050] In one or more embodiments, CY1 and CY2 may each be independently selected from benzene rings, naphthalene rings, pyridine rings, pyrimidine rings, pyridazine rings, and pyrazine rings.

[0051] In Equation 1, L1 can be selected from C5-C that are either unsubstituted or substituted with at least one R3. 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) and C1-C 60 Heterocyclic group.

[0052] In the embodiments, L1 may be selected from phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adamantylene, acenaphthelene, fluorene, spirodifluorene, spiro-benzofluorene-fluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenenenylene, phenanthylene, anthraceneylene, fluoranthylene, pyreneylene, etc., which are either unsubstituted or substituted with at least one R3. The group consists of the following compounds: benzotetraphenyl, purinyl, perylene, pyrrolyl, thiophenyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzoimidazolyl, imidazopyridinyl, and imidazopyrimidinyl.

[0053] For example, L1 can be an unsubstituted or substituted phenylene oxide with at least one R3, but the embodiments of this disclosure are not limited thereto.

[0054] In Formula 1, B1 can be a group represented by Formula 2:

[0055] Formula 2

[0056]

[0057] In Equation 2, Ar1 can be selected from those that are not substituted or have at least one R substituted. 103 C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) and C1-C 60 Heterocyclic groups, wherein Ar1 does not include triazine.

[0058] In the embodiments, Ar1 may be selected from those that are not substituted or those substituted with at least one R. 103 Phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, spiro-benzofluoren-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenatenyl, phenanthryl, anthraceneyl, fluoranthyl, pyrene, The following groups are listed: alkyl, tetraphenyl, furanyl, perylyl, pyrrolyl, thiophenyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzothiophenyl, dibenzothiophenyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazopyridyl, and imidazopyrimidinyl.

[0059] In the embodiments, Ar1 may be selected from those that are not substituted or those substituted with at least one R. 103 Phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, spiro-benzofluoren-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenatenyl, phenanthryl, anthraceneyl, fluoranthyl, pyrene, The compounds are alkyl, tetraphenyl, furanyl, peryl, pyrroleyl, thiophenyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, benzothiophenyl, and dibenzothiophenyl.

[0060] In one or more embodiments, Ar1 may be selected from groups represented by formulas 4-1 to 4-20:

[0061]

[0062]

[0063] In equations 4-1 to 4-20,

[0064] Y1 can be selected from O, S, N(R) 103b ), C(R 103b (R) 103c ) and Si(R 103b (R) 103c ),

[0065] R103 Same as described elsewhere here,

[0066] R 103a R 103b and R 103c All are in conjunction with R in this specification 103 The descriptions are the same.

[0067] b13 can be an integer from 0 to 3.

[0068] b14 can be an integer from 0 to 4.

[0069] b15 can be an integer from 0 to 5.

[0070] b16 can be an integer from 0 to 6.

[0071] b17 can be an integer from 0 to 7.

[0072] b19 can be an integer from 0 to 9, and

[0073] * indicates a bonding site with an adjacent atom.

[0074] In the embodiments, B1 can be a group represented by Formula 2-1:

[0075] Equation 2-1

[0076]

[0077] In Equation 2-1,

[0078] R 101 To R 103 All are the same as those described elsewhere here.

[0079] b15 can be an integer from 0 to 5, and

[0080] * indicates a bonding site with an adjacent atom.

[0081] In Equation 1, n1 represents the number of B1s and can be an integer from 1 to 5. When n1 is 2 or greater, two or more B1s can be the same or different from each other.

[0082] In the embodiments, n1 can be 1, 2 or 3, but the embodiments of this disclosure are not limited thereto.

[0083] In Equations 1 and 2, R1 to R3 and R 101 To R 103 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, substituted or unsubstituted C1-C groups. 60Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), wherein R 103 Triazine is not included.

[0084] b1 and b2 can both be independent integers from 0 to 10.

[0085] b1 and b2 represent the number of R1s and the number of R2s, respectively, and can both be independent integers from 0 to 10. When b1 is 2 or greater, two or more R1s can be the same or different from each other. When b2 is 2 or greater, two or more R2s can be the same or different from each other.

[0086] In the embodiments, R1 to R3 in Equation 1 can all be independently selected from:

[0087] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0088] All are substituted with at least one of the C1-C groups selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl. 20 Alkyl and C1-C 20 Alkoxy;

[0089] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, pyrene, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrrole, thiophene, furanyl, thiorhelyl, imidazolyl, pyrazolyl, thiazolyl Isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoindoleyl, indazolyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzo[] Thiolyl, isobenzothiazolyl (benzoisothiazolyl, e.g., benzo[d]isothiazolyl), benzoxazolyl, benzoisoxazolyl (isobenzoxazolyl, e.g., benzo[d]isoxazolyl), triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidyl, oxazolpyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspirodifluorenyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiaphenyl, azadibenzothiazolyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) and -B(Q1)(Q2); and

[0090] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spirodifluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[2]fluorenyl, dibenzo[2]fluorenyl, pyrene, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purine, quinolinyl, isoquinolinyl, benzo[2]quinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrene, acridine alkyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiolyl, isobenzothiazoleyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspirodifluorenyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophene, azadibenzothiol, biphenyl, terphenyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 The following are selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[9,10]fluorenyl, pyrrolyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indoleyl, purineyl, quinolinyl, isoquinolinyl, benzo[9,10]quinolinyl, phthalazinyl, naphthidyl, quinoxalin ... Azolinyl, cenolinyl, phenanthridine, acridine, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, isobenzothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazole, benzocarbazole, dibenzocarbazole, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspirodifluorenyl, azacarbazole, azadibenzofuranyl, azadibenzothiophene, and azadibenzothiopyrrolyl, and

[0091] Q1 to Q3 and Q 31 To Q33 They can all be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenanthryl, biphenyl, terphenyl, tetraphenyl and pyridyl.

[0092] In the embodiment, R in Equation 2 101 and R 102 They can all be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and phenyl.

[0093] For example, R 101 and R 102 All of them can be methyl, but the embodiments disclosed herein are not limited thereto.

[0094] In the embodiment, R in Equation 2 103 It can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptanenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranthyl, pyreneyl alkyl, tetraphenyl, styrene, peryl, pentylene, hexaphenyl, pentaphenyl, rubidinyl, benzoyl, oleyl, pyrroleyl, thiopheneyl, furanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzofuranyl, and benzothiopheneyl;

[0095] All are substituted with at least one of the C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, and cyano. 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptanenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranthyl, pyreneyl alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, pyrroleyl, thiopheneyl, furanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzofuranyl, and benzothiopheneyl; and

[0096] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),and

[0097] Q 31 To Q 33 Each can be independently selected from C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and pyridyl.

[0098] In the embodiment, Equation 1 is composed of The represented portion may be selected from groups represented by formulas A-1 to A-9:

[0099]

[0100] In equations A-1 to A-9,

[0101] R 31 To R 35 All are the same as those described in conjunction with R3.

[0102] B2 through B3 are identical to those described in conjunction with B1, and

[0103] * indicates a bonding site with an adjacent atom.

[0104] In one or more embodiments, Equation 1 is derived from... The represented portion may be selected from the groups represented by formulas A-11 to A-15:

[0105]

[0106] In equations A-11 to A-15,

[0107] R 31 To R 35 All are the same as those described in conjunction with R3.

[0108] R 101 To R 103 All are the same as those described elsewhere here.

[0109] R 104 R 105 R 107 and R 108 All are associated with binding R 101 The descriptions are the same.

[0110] R106 and R 109 All are associated with binding R 103 The descriptions are the same.

[0111] b15 can be an integer from 0 to 5, and

[0112] * indicates a bonding site with an adjacent atom.

[0113] In the embodiments, R in formulas A-11 to A-15 31 To R 35 R 103 R 106 and R 109 All of them can be hydrogen, but the embodiments disclosed herein are not limited thereto.

[0114] In the embodiments, R in formulas A-11 to A-15 101 R 102 R 104 R 105 R 107 and R 108 All of them can be methyl, but the embodiments disclosed herein are not limited thereto.

[0115] In one or more embodiments, Equation 1 is derived from... The represented portion may be selected from the groups represented by formulas A-16 to A-20:

[0116]

[0117] In equations A-16 to A-20,

[0118] * indicates a bonding site with an adjacent atom.

[0119] In the embodiments, R1 and R2 in Formula 1 can both be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups, groups represented by formulas 5-1 to 5-79, and groups including those derived from... The indicated portion is an electron-donating group, wherein, The asterisks, asterisks, and asterisks in the figure all represent bonding sites with adjacent atoms.

[0120]

[0121]

[0122]

[0123]

[0124] In equations 5-1 to 5-79,

[0125] Y 31 It can be selected from O, S, N (Z) 35 ), C(Z) 33 (Z) 34 ) and Si(Z 36 (Z) 37 ),

[0126] Z 31 To Z 37 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spirodifluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranthryl, benzo[9,10]phenanthrene, pyridyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[9,10]quinolinyl, naphthinyl, quinoxalinyl, quinazolinyl, carbazole, phenanthrinyl, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),

[0127] e2 can be 1 or 2.

[0128] e3 can be an integer from 1 to 3.

[0129] e4 is an integer from 1 to 4.

[0130] e5 is an integer from 1 to 5.

[0131] e6 is an integer from 1 to 6.

[0132] e7 can be an integer from 1 to 7.

[0133] e9 can be an integer from 1 to 9.

[0134] Q 31 To Q 33 Each can be independently selected from C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and pyridyl, and

[0135] * indicates a bonding site with an adjacent atom.

[0136] In the embodiments, including by The electron-donating group represented can be selected from...

[0137] Groups represented by formulas 6-1 to 6-3:

[0138]

[0139] In equations 6-1 to 6-3,

[0140] Y 61 It can be selected from O, S, N (Z) 63 ), C(Z) 63 (Z) 64 ) and Si(Z 63 (Z) 64 ),

[0141] Z 61 To Z 64 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthyl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, thiophenyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, benzothiophenyl, dibenzothiophenyl, -N(Q) 31 (Q) 32 ) and -Si(Q 31 (Q) 32 (Q) 33 ),

[0142] c61 and c62 can both be independent integers from 1 to 4.

[0143] Q1 and Q2 can both be independently selected from C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 20 Aryl, substituted with C1-C 20 C6-C of alkyl groups 20Aryl, C1-C 20 heteroaryl, substituted with C1-C 20 C1-C of alkyl 20 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0144] Q 31 To Q 33 Each can be independently selected from C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and pyridyl, and

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

[0146] In one or more embodiments, including by The electron-donating group represented may be selected from the groups represented by formulas 7-1 to 7-8:

[0147]

[0148] In equations 7-1 to 7-8,

[0149] As used here, "iso-Bu" represents isobutyl, and "t-Bu" represents tert-butyl.

[0150] * indicates a bonding site with an adjacent atom.

[0151] In an embodiment, at least one of R1 and R2 in Equation 1 may be a combination of... The part representing the electron-donating group.

[0152] In one or more embodiments, at least one of R1 and R2 in Formula 1 may be selected from groups represented by Formulas 6-1 to 6-3.

[0153] In one or more embodiments, in Equation 1,

[0154] R1 and R2 can both be independently defined as including the components of... The indicated part is the electron-donating group.

[0155] One of R1 and R2 can be composed of... The electron-donating group represented by R1 and R2 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C. 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 5-1 to 5-79, or

[0156] R1 and R2 can both be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 5-1 to 5-79.

[0157] In the embodiments, R1 and R2 in Formula 1 can both be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 7-1 to 7-10:

[0158]

[0159] In equations 7-1 to 7-10,

[0160] As used here, "iso-Bu" represents isobutyl, and "t-Bu" represents tert-butyl.

[0161] * indicates a bonding site with an adjacent atom.

[0162] In one or more embodiments, the heterocyclic compound may be represented by Formula 1-1:

[0163] Formula 1-1

[0164]

[0165] In Equation 1-1,

[0166] R 11 To R 14 All are the same as those described in combination with R1.

[0167] R 21 To R 24 All are the same as those described in combination with R2, and

[0168] L1, B1, and n1 are the same as those described elsewhere here.

[0169] In the embodiment, R in Equation 1-1 13 and R 23 At least one of them can be including the The part representing the electron-donating group.

[0170] In one or more embodiments, in Equation 1-1,

[0171] i)R 13 and R 23 Each can be independently composed of The indicated part is the electron-donating group.

[0172] ii)R 13 and R 23 One of them could be including those made by The part representing the electron-donating group, R 13 and R 23 The other group can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 5-1 to 5-79, or

[0173] iii)R 13 and R 23 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C. 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 5-1 to 5-79:

[0174]

[0175]

[0176]

[0177]

[0178] In equations 5-1 to 5-79,

[0179] Y 31 It can be selected from O, S, N (Z) 35 ), C(Z) 33 (Z) 34 ) and Si(Z 36 (Z) 37 ),

[0180] Z 31 To Z 37 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spirodifluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranthryl, benzo[9,10]phenanthrene, pyridyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[9,10]quinolinyl, naphthinyl, quinoxalinyl, quinazolinyl, carbazole, phenanthrinyl, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),

[0181] e2 can be 1 or 2.

[0182] e3 can be an integer from 1 to 3.

[0183] e4 can be an integer from 1 to 4.

[0184] e5 can be an integer from 1 to 5.

[0185] e6 can be an integer from 1 to 6.

[0186] e7 can be an integer from 1 to 7.

[0187] e9 can be an integer from 1 to 9.

[0188] Q 31 To Q 33 Each can be independently selected from C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, and pyridyl, and

[0189] * indicates a bonding site with an adjacent atom.

[0190] In one or more embodiments, R in Formula 1-1 11 To R 14 and R 21 To R 24 Each group can be independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C. 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 7-1 to 7-10.

[0191] In the embodiments, the heterocyclic compound may be selected from compound 1 to compound 125, but the embodiments of this disclosure are not limited thereto:

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] In heterocyclic compounds In the indicated portion, B1 may include direct connections to L1 and are defined by *-C(R) 101 (R) 102 The "methylene" is represented by '-*'. Therefore, one or more Ar1 atoms can be positioned (e.g., bonded) around L1 via methylene groups with relatively short bond lengths, thereby improving (e.g., increasing) the steric hindrance around the nitrogen atom.

[0198] Heterocyclic compounds can reduce intermolecular interactions with surrounding molecules by including a substituent with large steric hindrance at the nitrogen atom (e.g., by increasing steric hindrance at the nitrogen atom).

[0199] For example, in embodiments where a heterocyclic compound is used as the host in the emitter layer, intermolecular interactions with the material used as a dopant in the emitter layer can be reduced, making it less likely for host-dopant molecules to form exciton complexes. In this respect, excitons formed in the host molecule can be efficiently transferred to the dopant molecule, resulting in a significant improvement in the color purity and efficiency of the organic light-emitting device.

[0200] In heterocyclic compounds, Ar1 does not include a triazine group. For example, in embodiments where Ar1 includes a carbocyclic group, orbital overlap between the heterocyclic compound and the dopant molecule can be reduced, thereby reducing the likelihood of exciton complex formation. Therefore, in embodiments where the heterocyclic compound is used as the host in the emitting layer of an organic light-emitting device, excitons formed in the host molecule can be effectively transferred to the dopant molecule, resulting in a significant improvement in the color purity and efficiency of the organic light-emitting device.

[0201] Furthermore, in embodiments where the heterocyclic compound includes an electron-donating group (such as a carbazole group) as a substituent, hole mobility can be improved. In this regard, the recombination region for hole-electron recombination to form excitons can be expanded, and such recombination regions can be generated in the emitter layer. Therefore, organic light-emitting devices incorporating heterocyclic compounds can have improved effects in terms of low driving voltage, high efficiency, and lifetime.

[0202] Therefore, electronic devices (e.g., organic light-emitting devices) including heterocyclic compounds represented by Formula 1 can have low driving voltage, high efficiency, high maximum quantum yield and long lifetime.

[0203] By referring to the following examples, those skilled in the art will understand the method for synthesizing heterocyclic compounds represented by Formula 1.

[0204] At least one of the heterocyclic compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device. For example, the heterocyclic compound can be included in at least one selected from a hole transport region, an electron transport region, and an emitter layer. In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a material for a capping layer located outside a pair of electrodes in an organic light-emitting device.

[0205] Therefore, another aspect of the embodiments of this disclosure provides an organic light-emitting device, which 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 a light-emitting layer, wherein the organic light-emitting device includes at least one heterocyclic compound represented by Formula 1.

[0206] In an embodiment, the organic layer of the organic light-emitting device may include at least one heterocyclic compound represented by Formula 1.

[0207] The expression “(organic layer) comprises at least one heterocyclic compound” as used herein can include cases where “(organic layer) comprises the same heterocyclic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different heterocyclic compounds represented by Formula 1”.

[0208] For example, the organic layer may consist only of compound 1 as a heterocyclic compound. Here, compound 1 may be included in the emitting layer of an organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as heterocyclic compounds. Here, compound 1 and compound 2 may exist in the same layer (e.g., both compound 1 and compound 2 may exist in the emitting layer) or they may exist in different layers (e.g., compound 1 may exist in the emitting layer and compound 2 may exist in the hole transport layer).

[0209] In embodiments, the first electrode of the organic light-emitting device may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0210] The second electrode of an organic light-emitting device may include lithium (Li), Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, ytterbium (Yb), silver-ytterbium (Ag-Yb), or any combination thereof, and

[0211] The organic layer of an organic light-emitting device may include at least one heterocyclic compound represented by Formula 1.

[0212] In this embodiment, the first electrode of the organic light-emitting device can be the anode.

[0213] The second electrode of an organic light-emitting device can be a cathode, and

[0214] The organic layer may further include a hole transport region between the first electrode and the emitter layer and an electron transport region between the emitter layer and the second electrode.

[0215] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and

[0216] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0217] In an embodiment, the emission layer may include a heterocyclic compound represented by Formula 1.

[0218] In one or more embodiments, the emitter layer may include a host and a dopant, and the host may include a heterocyclic compound represented by Formula 1. In the emitter layer, the amount of the host may be greater than the amount of the dopant. For example, based on 100 parts by weight of the emitter layer, the amount of the host may range from about 50 parts by weight to about 99.9 parts by weight.

[0219] In the embodiments, the dopant may be a fluorescent dopant, a phosphorescent dopant, or any combination thereof.

[0220] In one or more embodiments, the dopant may be a phosphorescent dopant, which may include an organometallic complex represented by formula 401:

[0221] Formula 401

[0222] M(L 401 ) xc1 (L 402 ) xc2

[0223] Formula 402

[0224]

[0225] In Equations 401 and 402,

[0226] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).

[0227] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0228] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.

[0229] X 401 To X 404 They can each be nitrogen or carbon independently.

[0230] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.

[0231] A 401 and A 402 Each can be independently C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) or C1-C 60 Heterocyclic group,

[0232] 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 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0233] X 406 It can be a single bond, O, or S.

[0234] R401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), where Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0235] xc11 and xc12 can both be independent integers from 0 to 10, and

[0236] In Equation 402, * and *' both represent the binding position with M in Equation 401.

[0237] In one or more embodiments, the emitter layer may include a host and a dopant, and the dopant may include a heterocyclic compound represented by Formula 1. In the emitter layer, the amount of dopant may range from about 0.1 parts by weight to about 50 parts by weight, based on 100 parts by weight of the emitter layer.

[0238] In embodiments, the emitting layer comprising a heterocyclic compound represented by Formula 1 can emit blue or green light. In one or more embodiments, the emitting layer comprising a heterocyclic compound represented by Formula 1 can emit light having a maximum emission wavelength in the range of about 430 nm to about 530 nm.

[0239] In an embodiment, the hole transport region of the organic light-emitting device may include a charge-generating material. In an embodiment, the charge-generating material may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or lower.

[0240] In the embodiments, the electron transport region of the organic light-emitting device may also include a metal-containing material.

[0241] In embodiments, the electron transport region may further include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.

[0242] As used herein, the term "organic layer" refers to a single layer and / or all layers between the first and second electrodes of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials. For example, the organic layer may include inorganic materials.

[0243] Figure 1 Description

[0244] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0245] In the following text, we will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method of manufacturing the organic light-emitting device 10 are described.

[0246] First electrode 110

[0247] exist Figure 1 In this configuration, the substrate may be located below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate, both possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0248] The first electrode 110 can be formed, for example, by depositing and / or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material used for the first electrode 110 can be selected from materials with high work function to facilitate hole injection.

[0249] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can 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 this disclosure are not limited thereto.

[0250] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.

[0251] Organic layer 150

[0252] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emitter layer.

[0253] The organic layer 150 may also include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.

[0254] Hole transport region in organic layer 150

[0255] The hole transport region may have: i) a single-layer structure comprising a single layer of a single material; ii) a single-layer structure comprising a single layer of multiple different materials; or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0256] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.

[0257] For example, the hole transport region can have a single-layer structure or a multi-layer structure. The single-layer structure includes a single layer containing a variety of different materials. The multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure. For each structure, the layers are stacked sequentially from the first electrode 110 in the order stated therein, but the structure of the hole transport region is not limited to this.

[0258] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by Formula 201, and compounds represented by Formula 202:

[0259]

[0260]

[0261] Formula 201

[0262]

[0263] Formula 202

[0264]

[0265] In equations 201 and 202,

[0266] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,

[0267] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups.

[0268] xa1 to xa4 can each be an independent integer from 0 to 3.

[0269] xa5 can be an integer from 1 to 10, and

[0270] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.

[0271] For example, in equation 202, R 201 and R 202 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene, and R 203 and R 204 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene.

[0272] In the embodiments, in equations 201 and 202,

[0273] L 201 To L 205 Each can be independently selected from:

[0274] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenyl, anthracene, fluorenyl, benzo[9,10]phenenyl, pyrene, phenylene alkyl, benzotetraphenyl, purylene, perylene, pentaphenylene, benzohexaphenylene, benzopentaphenylene, benzobenzyl, benzoylene, oleophylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzothiopheneyl, and pyridylene; and

[0275] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirodifluoreneylene, benzo[9,10]fluoreneylene, dibenzo[9,10]fluoreneylene, phenanthroline, anthraceneylene, fluoranthroline, benzo[9,10]phenanthroline, pyreneylene, etc. The following compounds are listed: alkyl, tetraphenyl, terephthalyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, oleophyl, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl.

[0276] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0277] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.

[0278] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0279] In one or more embodiments, R 201 To R 204 and Q 201 All of these can be independently selected from: phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and

[0280] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, The following compounds are listed: alkyl, tetraphenyl, furanyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl.

[0281] Q 31 To Q 33 All are the same as those described elsewhere here.

[0282] In one or more embodiments, R from formula 201 201 To R 203 At least one of the selected items can be independently selected from:

[0283] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and

[0284] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The alkyl group of phenyl, the phenyl group substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl are selected from at least one of the following: fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl.

[0285] However, the embodiments disclosed herein are not limited thereto.

[0286] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204 They can be connected to each other via a single key.

[0287] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:

[0288] Carbazolyl; and

[0289] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The carbazoyl group selected from at least one of the following: alkyl phenyl, phenyl substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.

[0290] However, the embodiments disclosed herein are not limited thereto.

[0291] The compound represented by formula 201 can be represented by formula 201-1:

[0292] Formula 201-1

[0293]

[0294] In the embodiments, the compound represented by formula 201 may be represented by formula 201-2, but the embodiments of this disclosure are not limited thereto:

[0295] Formula 201-2

[0296]

[0297] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201-2(1), but the embodiments of this disclosure are not limited thereto:

[0298] Equation 201-2(1)

[0299]

[0300] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0301] Formula 201A

[0302]

[0303] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0304] Formula 201A(1)

[0305]

[0306] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0307] Formula 201A-1

[0308]

[0309] In the embodiments, the compound represented by formula 202 can be represented by formula 202-1:

[0310] Formula 202-1

[0311]

[0312] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202-1(1):

[0313] Equation 202-1(1)

[0314]

[0315] In one or more embodiments, the compound represented by formula 202 may be represented by formula 202A:

[0316] Formula 202A

[0317]

[0318] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A-1:

[0319] 202A-1

[0320]

[0321] In equations 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

[0322] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 All are the same as those described elsewhere here.

[0323] L 205 It can be selected from phenylene and fluorene.

[0324] X 211 It can be selected from O, S and N(R) 211 ),

[0325] X 212 It can be selected from O, S and N(R) 212 ),

[0326] R 211 and R 212 All are associated with binding R 203 The descriptions are the same, and

[0327] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene, alkyl, tetraphenyl, furanyl, perylene, pentyranyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.

[0328] The hole transport region may include at least one compound selected from compound HT1 to compound HT48, but embodiments of this disclosure are not limited thereto:

[0329]

[0330]

[0331]

[0332]

[0333] The thickness of the hole transport region can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the range. When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within a certain range, the thickness of the hole transport layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the range mentioned above, when the hole transport region, the hole injection layer, and the thickness of the hole transport layer are all within any of these ranges, suitable or satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0334] The emission assist layer can improve luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can include the materials described above.

[0335] p-doped agent

[0336] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.

[0337] The charge-generating material can be, for example, a p-doped agent.

[0338] In one embodiment, the LUMO level of the p-doped agent can be -3.5 eV or lower.

[0339] p-dopers may include at least one selected from quinone derivatives, metal oxides and cyano-containing compounds, but the embodiments of this disclosure are not limited thereto.

[0340] In one embodiment, the p-doper may include at least one selected from the following compounds:

[0341] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);

[0342] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0343] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0344] The compound represented by formula 221,

[0345] However, the embodiments disclosed herein are not limited thereto:

[0346]

[0347] Equation 221

[0348]

[0349] In Equation 221,

[0350] R 221 To R 223Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and from R 221 To R 223 At least one of the selected groups may have a C1-C group substituted with cyano, -F, -Cl, -Br, -I, or -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and substituted C1-C groups with -I 20 At least one substituent selected from alkyl groups.

[0351] Emission layer in organic layer 150

[0352] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with each other (e.g., physically in contact) or separated from each other. In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0353] The emitting layer may include a host and a light-emitting material. The light-emitting material may include at least one selected from phosphorescent dopants, fluorescent dopants, and quantum dots.

[0354] Based on about 100 parts by weight of the body, the amount of dopant in the emitter layer can be in the range of about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0355] The thickness of the emission layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the range mentioned above, excellent light emission characteristics can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within any of these ranges.

[0356] The main body in the emission layer

[0357] The host may include a heterocyclic compound represented by Formula 1.

[0358] The main body may also include compounds represented by formula 301:

[0359] Formula 301

[0360] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0361] In Equation 301,

[0362] Ar 301 C5-C can be substituted or unsubstituted. 60 Carbocyclic group (or substituted or unsubstituted C4-C) 60 (Carbocyclic group) or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0363] xb11 can be 1, 2, or 3.

[0364] L 301 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups.

[0365] xb1 can be an integer from 0 to 5.

[0366] R 301 It can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) and -P(=O)(Q 301 (Q) 302 ),

[0367] xb21 can be an integer from 1 to 5, and

[0368] Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0369] In the embodiment, Ar in formula 301 301 It can be selected from:

[0370] Naphthalene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups; and

[0371] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q)32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following groups are selected from at least one of the following groups: naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenatene group, anthracene group, fluoranthene group, benzo[9,10]phenatene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups, and

[0372] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0373] When xb11 in equation 301 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.

[0374] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0375] Formula 301-1

[0376]

[0377] Formula 301-2

[0378]

[0379] In Equations 301-1 and 301-2,

[0380] A 301 To A 304 They can all be independently selected from benzene rings, naphthalene rings, phenanthrene rings, fluoranthene rings, benzo[9,10]phenanthrene rings, pyrene rings, Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spirobisfluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, indole rings, carbazole rings, benzo[a]carbazole rings, dibenzo[a]carbazole rings, furan rings, benzo[a]furan rings, dibenzo[a]furan rings, naphtho[a]furan rings, benzo[a]naphtho[a]furan rings, dinaphtho[a]furan rings, thiophene rings, benzo[a]thiophene rings, dibenzo[a]thiophene rings, naphtho[a]thiophene rings, benzo[a]naphtho[a]thiophene rings, and dinaphtho[a]thiophene rings.

[0381] X 301It can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0382] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),

[0383] xb22 and xb23 can each be independently 0, 1, or 2.

[0384] L 301 xb1, R 301 and Q 31 To Q 33 All are the same as those described elsewhere here.

[0385] L 302 To L 304 Each independently binds to L 301 The descriptions are the same.

[0386] xb2 to xb4 are all independently identical to those described in conjunction with xb1, and

[0387] R 302 To R 304 Each independently binds to R 301 The descriptions are the same.

[0388] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be independently selected from:

[0389] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0390] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl The following groups are listed: pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediphenyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidoxazolyl, benzimidoxazolyl, triazolel, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl.

[0391] Q 31 To Q 33 All are the same as those described elsewhere here.

[0392] In one or more embodiments, R in Formula 301, Formula 301-1 and Formula 301-2 301 To R 304 Each can be independently selected from:

[0393] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0394] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[1,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.

[0395] Q 31 To Q 33 All are the same as those described elsewhere here.

[0396] In one or more embodiments, the host may include an alkaline earth metal complex and / or a zinc (Zn) complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.

[0397] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0398]

[0399]

[0400]

[0401] Phosphorescent dopants in the emission layer of organic layer 150

[0402] Phosphorescent dopants may include organometallic complexes represented by formula 401:

[0403] Formula 401

[0404] M(L 401 ) xc1 (L 402 ) xc2

[0405] Formula 402

[0406]

[0407] In Equations 401 and 402,

[0408] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).

[0409] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0410] L 402It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.

[0411] X 401 To X 404 They can each be nitrogen or carbon independently.

[0412] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.

[0413] A 401 and A 402 Each can be independently C5-C 60 Carbocyclic group (or C4-C) 60 (Carbocyclic group) or C1-C 60 Heterocyclic group,

[0414] 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 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0415] X 406 It can be a single bond, O, or S.

[0416] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), and Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0417] xc11 and xc12 can both be independent integers from 0 to 10, and

[0418] In Equation 402, * and *' both represent the binding position with M in Equation 401.

[0419] In the embodiment, A in formula 402 401 and A 402 They can all be independently selected from phenyl groups, naphthyl groups, fluorene groups, spirodifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaloline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzooxazole groups, isobenzooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.

[0420] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, X 402 It can be carbon, or ii)X 401 and X 402 Both can be nitrogen.

[0421] In one or more embodiments, R in Formula 402 401 and R 402 Each can be independently selected from:

[0422] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0423] All are substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl. 20 Alkyl and C1-C 20 Alkoxy;

[0424] Cyclopentyl, cyclohexyl, adamantyl, norbornel, norbornel-enyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0425] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and

[0426] -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 );and

[0427] Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.

[0428] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Optionally via X as a linker 407 Connected to each other, two A's 402 Optionally via X as a linker 408 They are interconnected (see compounds PD1 through PD4 and PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.

[0429] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The components may be selected from halogens, diketones (e.g., acetylacetone (compound)), carboxylic acids (e.g., pyridinecarboxylic acid (salt)), -C (=O), isonitriles, -CN and phosphorus-containing substances (e.g., phosphine or phosphorous acid (salt)), but the embodiments disclosed herein are not limited thereto.

[0430] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but the embodiments of this disclosure are not limited thereto:

[0431]

[0432] Fluorescent dopants in the emission layer

[0433] Fluorescent dopants may include arylamine compounds and / or styreneamine compounds.

[0434] Fluorescent dopants may include compounds represented by Formula 501:

[0435] Formula 501

[0436]

[0437] In Equation 501,

[0438] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group (or substituted or unsubstituted C4-C) 60 (Carbocyclic group) or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0439] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups.

[0440] xd1 to xd3 can each be an independent integer from 0 to 3.

[0441] R 501 and R 502 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and

[0442] xd4 can be an integer from 1 to 6.

[0443] In the embodiment, Ar in formula 501 501It can be selected from:

[0444] Naphthalene group, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, and indene-phenanthrene groups; and

[0445] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The naphthyl group selected from at least one of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, penfenol group, indene-anthracene group and indene-phenanthrene group.

[0446] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:

[0447] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenyl, benzo[9,10]phenanthrene, pyrene, phenanthrene alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, and pyridylene; and

[0448] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, The following are selected from at least one of the following groups: phenylene, perylene, pentofenyl, nehexaphenyl, nepentylphenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl; phenylene, naphthylene, fluoreneylene, spirodifluoreneyl, benzo[9,10]fluoreneyl, dibenzo[9,10]fluoreneyl, phenanthreneyl, anthraceneylene, fluorenyleneyl, benzo[9,10]phenanthreneyl, pyreneyleneyl, etc. The compounds are: alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzothiopheneyl, dibenzothiopheneyl, and pyridylene.

[0449] In one or more embodiments, R in Formula 501 501 and R 502 Each can be independently selected from:

[0450] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and

[0451] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[1,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, The following groups are listed: alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl.

[0452] Q 31 To Q 33 Can be selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0453] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.

[0454] For example, fluorescent dopants can be selected from compounds FD1 to FD22:

[0455]

[0456]

[0457]

[0458] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of this disclosure are not limited thereto:

[0459]

[0460] quantum dots

[0461] The emitting layer included in the organic light-emitting device of this disclosure may include quantum dots.

[0462] Quantum dots are particles with a crystal structure ranging from a few nanometers to tens of nanometers and contain hundreds to thousands of atoms.

[0463] Because quantum dots are extremely small, the quantum confinement effect can occur. The quantum confinement effect refers to the phenomenon where the band gap of an object increases as its size becomes smaller than a nanometer. Therefore, when a quantum dot is illuminated with light of a wavelength having an energy intensity greater than its band gap, the quantum dot is excited by absorbing the light and emits light of a fixed or specific wavelength, transitioning to its ground state. Here, the wavelength of the emitted light corresponds to the band gap.

[0464] The nucleus of a quantum dot can include group II-VI compounds, group III-VI compounds, group III-V compounds, group IV-VI compounds, group IV elements or compounds, group I-III-VI compounds, or combinations thereof.

[0465] Group II-VI compounds can be selected from binary, ternary, and quaternary compounds. Binary compounds are selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and any mixtures thereof. Ternary compounds are selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, Cd... ZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and any mixture thereof, wherein the quaternary compound is selected from CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and any mixture thereof.

[0466] Group III-VI compounds may include: binary compounds, such as In2S3 or In2Se3; ternary compounds, such as InGaS3 or InGaSe3; or any combination thereof.

[0467] For example, the III-V compounds may be selected from binary, ternary, and quaternary compounds. The binary compounds are selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and any mixture thereof. The ternary compounds are selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and any mixture thereof. The quaternary compounds are 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 this disclosure are not limited thereto. Group III-V compounds may also include Group II metals (e.g., InZnP, etc.).

[0468] Group IV-VI compounds can be selected from binary, ternary, and quaternary compounds. Binary compounds are selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and any mixture thereof. Ternary compounds are selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and any mixture thereof. Quaternary compounds are selected from SnPbSSe, SnPbSeTe, SnPbSTe, and any mixture thereof. Group IV elements can be selected from Si, Ge, and any mixture thereof. Group IV compounds can be binary compounds selected from SiC, SiGe, and any mixture thereof.

[0469] Binary, ternary, and / or quaternary compounds can exist in particles at a uniform (e.g., substantially uniform) concentration, or they can exist in the same particle in a state where the concentration distribution is locally different. Furthermore, binary, ternary, or quaternary compounds can have a core-shell structure in which one quantum dot surrounds another quantum dot. The interface between the core and shell can have a concentration gradient in which the concentration of the element present in the shell decreases towards the center.

[0470] In one or more embodiments, the quantum dot may have a core-shell structure comprising a core having the aforementioned nanoparticles and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for maintaining semiconductor properties by preventing or reducing chemical denaturation of the core, and / or as a charged layer for imparting electrophoretic properties to the quantum dot. The shell may be monolayer or multilayer. The interface between the core and shell may have a concentration gradient, wherein the concentration of elements present in the shell decreases towards the center along this concentration gradient. Examples of the shell of the quantum dot may include metal and / or nonmetal oxides, semiconductor compounds, or any combination thereof.

[0471] Examples of metal and / or nonmetal oxides include binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO) or ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4), but the embodiments of this disclosure are not limited thereto.

[0472] In addition, examples of semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments disclosed herein are not limited thereto.

[0473] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be about 45 nm or smaller, for example, about 40 nm or smaller, for example, about 30 nm or smaller. In addition, light emitted through such quantum dots is illuminated in all directions (e.g., essentially in every orientation), thereby improving (e.g., increasing) the width of the viewing angle.

[0474] In some embodiments, quantum dots may be used in the form of spherical, pyramidal, multi-armed, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.

[0475] Quantum dots can be used to adjust the color of emitted light by adjusting their particle size. Therefore, quantum dots can emit light of various suitable colors (e.g., blue, red, or green).

[0476] Electron transport region in organic layer 150

[0477] The electron transport region may have: i) a single-layer structure comprising a single layer of a single material; ii) a single-layer structure comprising a single layer of multiple different materials; or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0478] 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 the embodiments of this disclosure are not limited thereto.

[0479] 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 layers are stacked sequentially from the emitter layer in the order stated herein. However, embodiments of the electron transport region structure are not limited to these.

[0480] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring.

[0481] The term "π-electron-poor nitrogen-containing ring" as used here refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic group.

[0482] For example, a "nitrogen-containing ring depleted of π electrons" can be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are condensed together; or iii) at least one of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is combined with at least one C5-C 60 Carbocyclic group (or at least one C4-C) 60 Heterocyclic groups that are condensed (e.g., combined) with carbocyclic groups.

[0483] Examples of π-electron-depleted nitrogen-containing rings include, but are not limited to, imidazole rings, pyrazole rings, thiazole rings, isothiazole rings, oxazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, indazole rings, purine rings, quinoline rings, isoquinoline rings, benzo[a]quinoline rings, phthalazine rings, naphthidine rings, quinoxaline rings, quinazoline rings, cyclophosphine rings, phenanthridine rings, acridine rings, phenanthrene-rhein rings, phenazine rings, benzimidazole rings, benziisothiazole rings, benziisoxazole rings, benziisoxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.

[0484] For example, the electron transport region may include a compound represented by Formula 601:

[0485] Formula 601

[0486] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0487] In Equation 601,

[0488] Ar 601 C5-C can be substituted or unsubstituted. 60 Carbocyclic group (or substituted or unsubstituted C4-C) 60 (Carbocyclic group) or substituted or unsubstituted C1-C 60 Heterocyclic group,

[0489] xe11 can be 1, 2, or 3.

[0490] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,

[0491] xe1 can be an integer from 0 to 5.

[0492] R 601 It can be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0493] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0494] xe21 can be an integer from 1 to 5.

[0495] In the embodiment, xe11 numbers of Ar 601 R with xe21 numbers 601 At least one of them may include a nitrogen-containing ring that is π-electron depleted.

[0496] In the embodiment, Ar in formula 601 601 It can be selected from:

[0497] Phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indoxanthracene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthidine groups, quinoxaloline groups, quinazolinoline groups, cyclophosphine groups, phenanthridine groups, acridine groups, phenanthrene-rhein groups, phenazine groups, benzimidazole groups, benziisothiazole groups, benzioxazole groups, benziisooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups; and

[0498] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, selected from at least one of the following: Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthidine groups, quinoxaloline groups, quinazoline groups, cinnamic acid groups, phenanthridine groups, acridine groups, phenanthrene-rhein groups, phenazine groups, benzimidazole groups, benziisothiazole groups, benzioxazole groups, benziisooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups, and

[0499] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0500] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.

[0501] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.

[0502] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:

[0503] Formula 601-1

[0504]

[0505] In Equation 601-1,

[0506] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,

[0507] L 611 To L 613 Each independently binds to L 601 The descriptions are the same.

[0508] xe611 to xe613 are all independently identical to those described in conjunction with xe1.

[0509] R 611 To R 613 Each independently binds to R 601 The descriptions are the same, and

[0510] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0511] In the embodiment, L in formula 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:

[0512] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and

[0513] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazine The following are at least one of the following groups selected from: phenylene, naphthidyl, quinoxalinyl, quinazolinyl, phenanthrynyl, phenanthroxylinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrynyl, anthraceneyl, fluorenyl, benzo[9,10]phenanthrynyl, pyreneyl, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthinyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl.

[0514] However, the embodiments disclosed herein are not limited thereto.

[0515] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each be independently 0, 1 or 2.

[0516] In one or more embodiments, R in Formula 601 601 R in equation 601-1 611 To R 613 Each can be independently selected from:

[0517] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0518] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalyl The phenyl, biphenyl, terphenyl, naphthinyl, quinoxalinyl, quinazolinyl, terazolinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and

[0519] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),and

[0520] Q 601 and Q 602 All are the same as those described elsewhere here.

[0521] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0522]

[0523]

[0524]

[0525]

[0526] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.

[0527]

[0528] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can all be independently set to approximately [value missing]. to approximately Within a certain range, for example, in approximately to approximately Within the aforementioned range, when the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within the aforementioned range, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without significantly increasing the driving voltage.

[0529] The thickness of the electron transport layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the range mentioned above, when the thickness of the electron transport layer is within any of these ranges, the electron transport layer can have suitable or satisfactory electron transport characteristics without significantly increasing the driving voltage.

[0530] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include metallic materials.

[0531] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from Li, Na, K, Rb, and Cs ions, while alkaline earth metal complexes may include metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligands coordinated to the metal ions of the alkali metal or alkaline earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0532] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or compound ET-D2:

[0533]

[0534] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 190.

[0535] The electron injection layer may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0536] 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.

[0537] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, and / 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.

[0538] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0539] [[ID=二十一]]The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0540] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may be selected from oxides and halides of alkali metals, alkaline earth metals, and rare earth metals (e.g., the halides are selected from fluorides, chlorides, bromides, and iodides).

[0541] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, and K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI). In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0542] 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-xO(0 < x < 1)). In one 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.

[0543] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.

[0544] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may respectively include the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated with 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.

[0545] The electron injection layer may include the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof as described above (or may be composed of the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, 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, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0546] The thickness of the electron injection layer may be in the range of about to about For example, in the range of about [[ID=第十八]]to about When the thickness of the electron injection layer is within any of the above ranges, the electron injection layer may have suitable or satisfactory electron injection characteristics without significantly increasing the driving voltage.

[0547] The second electrode 190

[0548] The second electrode 190 is located on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode, and in this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof that have relatively low work functions.

[0549] 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), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, and IZO, but embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0550] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0551] Figures 2 to 4 Description

[0552] 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, stacked in the order stated herein. 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 stacked in the order stated herein. Figure 4 The 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 stacked in the order stated herein.

[0553] 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 Use the given description to understand.

[0554] In each of the organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210. In each of the organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass outward through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220.

[0555] The first capping layer 210 and the second capping layer 220 can improve the external luminescence efficiency based on the principle of constructive interference.

[0556] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, and / or a composite capping layer including organic and inorganic materials.

[0557] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents comprising at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.

[0558] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.

[0559] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto:

[0560]

[0561] In the above text, it has already been combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described. However, the embodiments disclosed herein are not limited thereto.

[0562] One or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging can be used to form layers constituting hole transport regions, emission layers, and electron transport regions in certain areas.

[0563] When forming layers constituting hole transport regions, emitter layers, and electron transport regions by vacuum deposition, by considering the materials to be included in the layers to be formed and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree and about / seconds to approximately Vacuum deposition is performed at a deposition rate of / second.

[0564] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at coating speeds of about 2,000 rpm to about 5,000 rpm and heat treatment temperatures of about 80°C to about 200°C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed.

[0565] General definition of substituents

[0566] As used herein, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched monovalent group of an aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is also used. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Alkyl groups are divalent groups with essentially the same structure.

[0567] As used herein, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 An alkyl group having at least one carbon-carbon double bond at its main chain (e.g., middle) or end (e.g., terminal) is a hydrocarbon group, examples of which include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in conjunction with this terminology. 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Alkenes are divalent groups with essentially the same structure.

[0568] As used herein, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 An alkyl group having at least one carbon-carbon triple bond at its main chain (e.g., middle) or end (e.g., terminal) is an alkyl group, examples of which include ethynyl and propynyl. As used herein, the term "C2-C" is used in conjunction with this terminology. 60 "Immyneyl" refers to a group with a C2-C group. 60 The alkynyl group is a divalent group with a basically the same structure.

[0569] As used herein, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, examples of which include methoxy, ethoxy, and isopropoxy.

[0570] As used herein, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms.10 Divalent groups with essentially the same structure as cycloalkyl groups.

[0571] As used herein, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms, examples of which include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with essentially the same structure as heterocyclic alkyl groups.

[0572] As used herein, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic (e.g., not aromatic), examples of which include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylidene alkenyl" refers to a group that has a similar structure to C3-C4. 10 A divalent group with a structure that is essentially the same as a cycloalkenyl group.

[0573] As used herein, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with essentially the same structure as heterocyclic alkenyl groups.

[0574] As used here, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, and as used herein, "C6-C" 60 "Aryl" refers to a divalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups include fluorenyl, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings may fused together (e.g., joined together).

[0575] As used herein, the term "C1-C"60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. As used herein, the term "C1-C" is also relevant. 60 "Hypo-aryl" refers to a divalent group having a heterocyclic aromatic system, wherein the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. C1-C 60 Examples of heteroaryl groups include carbazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings may condense together (e.g., combine together).

[0576] As used here, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), as used herein in the term "C6-C 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).

[0577] As used herein, the term "monovalent non-aromatic condensation polycyclic group" refers to a monovalent group having two or more rings condensed (e.g., bonded together), with only carbon atoms (e.g., having 8 to 60 carbon atoms) as cyclic atoms, and not aromatic throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of adamantyl alkyl is a monovalent non-aromatic condensation polycyclic group. As used herein, the term "divalent non-aromatic condensation polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensation polycyclic group.

[0578] As used herein, the term "monovalent non-aromatic condensed heterocyclic group" refers to a monovalent group having two or more rings condensed together (e.g., bonded together), at least one heteroatom selected from N, O, Si, P, and S as cyclic atoms other than carbon atoms (e.g., having 1 to 60 carbon atoms), and not aromatic throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of a monovalent non-aromatic condensed heterocyclic group is an azadamaneyl group. As used herein, the term "divalent non-aromatic condensed heterocyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heterocyclic group.

[0579] As used herein, the term "C5-C"60 "Carbocyclic group" or "C4-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon as the cyclic atom and consists of 5 to 60 carbon atoms or 4 to 60 carbon atoms (or is composed of 5 to 60 carbon atoms or 4 to 60 carbon atoms). C5-C 60 carbon cyclo group or C4-C 60 The carbocyclic group can be aromatic or non-aromatic. (C5-C) 60 carbon cyclo group or C4-C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the connection to C5-C... 60 carbon cyclo group or C4-C 60 The number of substituents in the carbocyclic group, C5-C 60 carbon cyclo group or C4-C 60 The carbon cyclic group can be a trivalent group or a tetravalent group.

[0580] As used herein, the term "C1-C" 60 A "heterocyclic group" refers to a group that, in addition to using at least one heteroatom selected from N, O, Si, P, and S (excluding carbon, which can be 1 to 60 carbon atoms) as a cyclic atom, has a cyclic structure similar to C5-C6. 60 Groups with essentially the same structure as carbon cyclic groups.

[0581] In this specification, C5-C is replaced. 60 Carbocyclic group (or substituted C4-C) 60 (Carbocyclic group), substituted C1-C 60 Heterocyclic groups, substituted C1-C 20 Alkylene, substituted C2-C 20 alkenyl, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heterocyclic group may be selected from:

[0582] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy

[0583] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy

[0584] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl

[0585] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, biphenyl, terphenyl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl, and

[0586] -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 ),and

[0587] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, substituted with C1-C 60 C6-C of alkyl groups 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.

[0588] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to tert-Bu. t "Refers to tert-butyl, as the term "OMe" used herein refers to methyl methacrylate (MMA).

[0589] As used herein, the term "biphenyl" refers to a phenyl group that has a substituted phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C bond. 60 Aryl groups are substituted phenyl groups.

[0590] As used herein, the term "terphenyl" refers to a phenyl group substituted with biphenyl groups. In other words, "terphenyl" is a phenyl group having C6-C substitutions. 60 C6-C of aryl 60 Aryl groups are substituted phenyl groups.

[0591] Unless otherwise defined, * and *' as used herein refer to the binding site with the adjacent atom in the corresponding expression.

[0592] In the following description, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in more detail with reference to the synthesis examples and examples. The expression "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of A.

[0593] Example

[0594] The heterocyclic compounds according to the embodiments can be synthesized, for example, as follows. However, the methods for synthesizing the heterocyclic compounds according to the embodiments of this disclosure are not limited thereto.

[0595] Synthesis Example 1. Synthesis of Compound 4

[0596] Compound 4 can be synthesized, for example, by scheme 1:

[0597] Option 1

[0598]

[0599] 1-1. Synthesis of intermediate 1-2

[0600] 10 g of bromo-3-fluorobenzene (CAS: 1073-06-9), 2.78 g of magnesium, and 0.15 g of iodine were refluxed in 60 mL of THF for 2 hours. Next, 13.73 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediates 1-2. Intermediates 1-2 were identified by LC / MS.

[0601] C9H 11 FO M+1:154.26

[0602] 1-2. Synthesis of intermediates 1-3

[0603] 5 g of intermediates 1-2 and 4.32 g of aluminum chloride were refluxed in 150 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediates 1-3. Intermediate 1-3 was identified by LC / MS.

[0604] C 15 H 15 F M+1:214.73

[0605] 1-3. Synthesis of Compound 4

[0606] 5.11 g of 9'H-9,3':6',9”-tricarbazole (CAS: 606129-90-2), 2 g of intermediates 1-3, and 4.95 g of tripotassium phosphate were dissolved in 50 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the resulting reaction solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 4.19 g of compound 4 (yield: 65%). Compound 4 was further purified by LC-MS and... 1 H-NMR identification.

[0607] C 51 H 37 N3 M+1:691.92

[0608] Synthesis Example 2. Synthesis of Compound 62

[0609] Compound 62 can be synthesized, for example, by scheme 2:

[0610] Option 2

[0611]

[0612] 2-1. Synthesis of intermediate 2-2

[0613] 10 g of bromo-4-fluorobenzene (CAS: 460-00-4), 2.78 g of magnesium, and 0.15 g of iodine were refluxed in 60 mL of THF for 2 hours. Next, 13.73 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 2-2. Intermediate 2-2 was identified by LC / MS.

[0614] C9H 11 FO M+1:154.52

[0615] 2-2. Synthesis of intermediate 2-3

[0616] 5 g of intermediate 2-2 and 4.32 g of aluminum chloride were refluxed in 160 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 2-3. Intermediate 2-3 was identified by LC / MS.

[0617] C 15 H15 F M+1:214.67

[0618] 2-3. Synthesis of Compound 62

[0619] 3.41 g of 9H-3,9'-bicarbazole (CAS: 18628-07-4), 2 g of intermediate 2-3, and 4.95 g of tripotassium phosphate were dissolved in 50 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 3.64 g of compound 62 (yield: 74%). Compound 62 was analyzed by LC-MS and... 1 H-NMR identification.

[0620] C 39 H 30 N2 M+1:526.96

[0621] Synthesis Example 3. Synthesis of Compound 65

[0622] Compound 65 can be synthesized, for example, by scheme 3:

[0623] Option 3

[0624]

[0625] 3-1. Synthesis of intermediate 3-2

[0626] 10 g of 1,3-dibromo-5-fluorobenzene (CAS: 1435-51-4), 2.87 g of magnesium, and 0.1 g of iodine were refluxed in 40 mL of THF for 2 hours. Next, 14.19 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 3-2. Intermediate 3-2 was identified by LC / MS.

[0627] C 12 H 17 FO2 M+1:212.41

[0628] 3-2. Synthesis of intermediate 3-3

[0629] 5 g of intermediate 3-2 and 3.14 g of aluminum chloride were refluxed in 120 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 3-3. Intermediate 3-3 was identified by LC / MS.

[0630] C 24 H 25 F M+1:332.89

[0631] 3-3. Synthesis of Compound 65

[0632] 2.2 g of 9H-3,9'-bicarbazole (CAS: 18628-07-4), 2 g of intermediate 3-3, and 3.19 g of tripotassium phosphate were dissolved in 50 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 2.52 g of compound 65 (yield: 65%). Compound 65 was analyzed by LC-MS and... 1 H-NMR identification.

[0633] C 48 H 40 N2 M+1:644.94

[0634] Synthesis Example 4. Synthesis of Compound 82

[0635] Compound 82 can be synthesized, for example, by scheme 4:

[0636] Option 4

[0637]

[0638] 4-1. Synthesis of intermediate 3-2

[0639] 10 g of 1,3-dibromo-5-fluorobenzene (CAS: 1435-51-4), 2.87 g of magnesium, and 0.1 g of iodine were refluxed in 40 mL of THF for 2 hours. Next, 14.19 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 3-2. Intermediate 3-2 was identified by LC / MS.

[0640] C12 H 17 FO2 M+1:212.41

[0641] 4-2. Synthesis of intermediate 3-3

[0642] 5 g of intermediate 3-2 and 3.14 g of aluminum chloride were refluxed in 120 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 3-3. Intermediate 3-3 was identified by LC / MS.

[0643] C 24 H 25 F M+1:332.89

[0644] 4-3. Synthesis of Compound 82

[0645] 3.29 g of 3,3”,6,6”-tetra-tert-butyl-9'H-9,3':6',9”-tricarbazole (CAS: 551951-04-3), 2 g of intermediate 3-3, and 3.19 g of tripotassium phosphate were dissolved in 30 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 4.35 g of compound 82 (yield: 70%). Compound 82 was analyzed by LC-MS and... 1 H-NMR identification.

[0646] C 76 H 79 N3 M+1:1033.74

[0647] Synthesis Example 5. Synthesis of Compound 88

[0648] Compound 88 can be synthesized, for example, by scheme 5:

[0649] Option 5

[0650]

[0651] 5-1. Synthesis of intermediate 4-2

[0652] 10 g of 1,3,5-tribromo-2-fluorobenzene (CAS: 3925-78-8), 2.92 g of magnesium, and 0.07 g of iodine were refluxed in 30 mL of THF for 2 hours. Next, 14.44 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 4-2. Intermediate 4-2 was identified by LC / MS.

[0653] C 15 H 23 FO3 M+1:270.47

[0654] 5-2. Synthesis of intermediate 4-3

[0655] The reaction was completed by reflux of 5 g of intermediate 4-2 and 2.46 g of aluminum chloride in 90 mL of benzene for 24 hours. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 4-3. Intermediate 4-3 was identified by LC / MS.

[0656] C 33 H 35 F M+1:450.66

[0657] 5-3. Synthesis of Compound 88

[0658] 2.45 g of N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine (CAS: 608527-58-8), 2 g of intermediate 4-3, and 2.35 g of tripotassium phosphate were dissolved in 25 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 1.36 g of compound 88 (yield: 33%). Compound 88 was analyzed by LC-MS and... 1 H-NMR identification.

[0659] C 69 H 61 N3 M+1:932.90

[0660] Synthesis Example 6. Synthesis of Compound 121

[0661] Compound 121 can be synthesized, for example, by scheme 6:

[0662] Option 6

[0663]

[0664] 6-1. Synthesis of intermediate 5-2

[0665] 10 g of bromo-2-fluorobenzene (CAS: 1072-85-1), 2.78 g of magnesium, and 0.15 g of iodine were refluxed in 60 mL of THF for 2 hours. Next, 13.73 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 5-2. Intermediate 5-2 was identified by LC / MS.

[0666] C9H 11 FO M+1:154.88

[0667] 6-2. Synthesis of intermediate 5-3

[0668] 5 g of intermediate 5-2 and 4.32 g of aluminum chloride were refluxed in 160 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 5-3. Intermediate 5-3 was identified by LC / MS.

[0669] C 15 H 15 F M+1:214.50

[0670] 6-3. Synthesis of Compound 121

[0671] 3.38 g of 3,6-bis(phenyl-d5)-9H-carbazole (CAS: 2179126-86-2), 2 g of intermediate 5-3, and 4.95 g of tripotassium phosphate were dissolved in 50 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 1.81 g of compound 121 (yield: 37%). Compound 121 was analyzed by LC-MS and... 1 H-NMR identification.

[0672] C 39 H 21D 10 N M+1:524.11

[0673] Synthesis Example 7. Synthesis of Compound 125

[0674] Compound 125 can be synthesized, for example, by scheme 7:

[0675] Option 7

[0676]

[0677] 7-1. Synthesis of intermediate 4-2

[0678] 10 g of 1,3,5-tribromo-2-fluorobenzene (CAS: 3925-78-8), 5.55 g of magnesium, and 0.15 g of iodine were refluxed in 60 mL of THF for 2 hours. Next, 27.46 g of acetone was added, and the resulting reaction solution was refluxed again for 10 minutes to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 4-2. Intermediate 4-2 was identified by LC / MS.

[0679] C 15 H 23 FO3 M+1:270.47

[0680] 7-2. Synthesis of intermediate 4-3

[0681] 5 g of intermediate 4-2 and 4.32 g of aluminum chloride were refluxed in 160 mL of benzene for 24 hours to complete the reaction. Extraction was performed by adding ethyl acetate to the resulting reaction solution, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain intermediate 4-3. Intermediate 4-3 was identified by LC / MS.

[0682] C 33 H 35 F M+1:450.66

[0683] 7-3. Synthesis of Compound 125

[0684] 1.6 g of 3,6-bis(phenyl-d5)-9H-carbazole (CAS: 2179126-86-2), 2 g of intermediate 4-3, and 2.36 g of tripotassium phosphate were dissolved in 50 mL of DMF, and the resulting reaction solution was refluxed for 24 hours. After the reaction was complete, the solution was extracted by adding ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The residue obtained by solvent evaporation was separated and purified by silica gel column chromatography to obtain 1.81 g of compound 125 (yield: 35%). Compound 125 was analyzed by LC-MS and... 1 H-NMR identification.

[0685] C 57 H 41 D 10 N M+1:760.41

[0686] The compounds synthesized according to Synthetic Examples 1 to 7 1 H NMR and LC / MS are shown in Table 1.

[0687] By referring to the above synthetic routes and raw materials, even compounds other than those shown in Table 1 can be easily recognized by those skilled in the art.

[0688] Table 1

[0689]

[0690]

[0691] Example 1

[0692] Use with A thin ITO substrate was used as the first electrode (anode). The ITO substrate was ultrasonicated with isopropanol and pure water for 5 minutes each, and then cleaned by ultraviolet irradiation and ozone exposure for 30 minutes to prepare it. The cleaned ITO substrate was then mounted onto a vacuum deposition apparatus.

[0693] N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (NPB) was vacuum deposited on an ITO substrate to form a product with... A hole injection layer of a certain thickness is formed. Next, mCP is vacuum-deposited on the hole injection layer to form a layer with… A hole transport layer of a certain thickness.

[0694] Next, compound 4 (body) and Ir(pmp)3 (dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form a structure with... The thickness of the emission layer.

[0695] Then, 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ) is deposited on the emitter layer to form a structure with... A thick electron transport layer is formed, on which LiF, as an alkali halide metal, is deposited to form an electron transport layer with [missing information]. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited on the electron-injected layer to form a layer with [missing information]. The thick LiF / Al electrode (cathode) is used to complete the fabrication of the organic light-emitting device.

[0696] The material used in organic light-emitting devices can be represented by the following formula:

[0697]

[0698] Examples 2 to 7

[0699] Organic light-emitting devices are fabricated in essentially the same manner as in Example 1, except that the compounds in Table 2 are used to form the emission layer.

[0700] Comparison Example 1 to Comparison Example 3

[0701] The organic light-emitting device is fabricated in a manner substantially the same as that in Example 1, except that compounds C1 to C3 are used respectively to form the emission layer.

[0702] Compound C1

[0703]

[0704] Compound C2

[0705]

[0706] Compound C3

[0707]

[0708] To evaluate the characteristics of the organic light-emitting devices of Examples 1 to 7 and Comparative Examples 1 to 3, measurements were taken at 10 mA / cm². 2The driving voltage, efficiency, and maximum quantum efficiency at the given current density were determined. The driving voltage and current density of the organic light-emitting device were measured using a source meter (Keithley Instrument, 2400 series), and the maximum quantum efficiency was measured using an external quantum efficiency measurement device C9920-2-12 from Hamamatsu Photonics Inc. In evaluating the maximum quantum efficiency, luminance / current density was measured using a luminance meter calibrated for wavelength sensitivity, and the maximum quantum efficiency was converted by assuming the introduction of an ideal reflective diffuser angular luminance distribution (Lambert). The evaluation results of the organic light-emitting device characteristics are shown in Table 2:

[0709] Table 2

[0710]

[0711] Referring to the results in Table 2, it can be seen that, compared with the organic light-emitting devices of Comparative Examples 1 to 3, the organic light-emitting devices of Examples 1 to 7 have low driving voltage, high efficiency, and high maximum quantum efficiency.

[0712] According to one or more embodiments, organic light-emitting devices comprising heterocyclic compounds can have low driving voltage and high efficiency.

[0713] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of this disclosure as defined by the claims and their equivalents.

Claims

1. An organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode faces the first electrode; as well as An organic layer, located between the first electrode and the second electrode, includes an emission layer. The first electrode comprises indium tin oxide, indium zinc oxide, tin oxide, zinc oxide, magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, magnesium-silver, or any combination thereof. The second electrode comprises lithium, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, ytterbium, silver-ytterbium, or any combination thereof. The organic layer comprises at least one heterocyclic compound represented by Formula 1-1: Equation 1-1 In Equation 1-1, Depend on The part represented is one of equations A-11 to A-15: R 11 To R 14 and R 21 To R 24 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 7-1 to 7-10: Among them, in equations 7-1 to 7-10, iso-Bu represents isobutyl, t-Bu represents tert-butyl, and * indicates a bonding site with an adjacent atom. Among them, in equations A-11 to A-15, R 31 To R 35 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl and C1-C 20 Alkoxy R 101 R 102 R 104 R 105 R 107 and R 108 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. R 103 R 106 and R 109 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy b15 is an integer from 0 to 5, and * indicates a bonding site with an adjacent atom. Among them, R 11 To R 14 and R 21 To R 24 At least one of them is independently selected from the groups represented by formulas 7-1 to 7-10.

2. The organic light-emitting device according to claim 1, wherein, The first electrode is the anode. The second electrode is a cathode, and The organic layer further includes a hole transport region located between the first electrode and the emitter layer, and an electron transport region located between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a 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 according to claim 1, wherein, The emission layer includes at least one heterocyclic compound represented by Formula 1-1.

4. The organic light-emitting device according to claim 3, wherein, The emitter layer comprises a host and a dopant, and The main body includes at least one heterocyclic compound represented by Formula 1-1.

5. The organic light-emitting device according to claim 4, wherein, The dopant includes phosphorescent dopant, fluorescent dopant, or any combination thereof.

6. The organic light-emitting device according to claim 4, wherein, The dopant is a phosphorescent dopant, and The phosphorescent dopant includes an organometallic complex represented by formula 401: Formula 401 M(L 401 ) xc1 (L 402 ) xc2 Formula 402 In Equations 401 and 402, M is selected from iridium, platinum, palladium, osmium, titanium, zirconium, hafnium, europium, terbium, rhodium, and thulium. L 401 For the ligand represented by Equation 402, xc1 is 1, 2, or 3, where when xc1 is 2 or greater, two or more L... 401 Whether they are the same or different, L 402 For organic ligands, xc2 is an integer from 0 to 4, where when xc2 is 2 or greater, two or more L... 402 Whether they are the same or different, X 401 To X 404 Each is independently either nitrogen or carbon. X 401 and X 403 Connected via a single or double bond, and X 402 and X 404 Connected via single or double bonds, A 401 and A 402 Each is independently C5-C 60 carbon cyclo group or C1-C 60 Heterocyclic group, X 405 For single bonds, *-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 Each is independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, X 406 For single bonds, O or S, R 401 and R 402 All are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), where Q 401 To Q 403 All were independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics, xc11 and xc12 are both independent integers from 0 to 10, and In Equation 402, * and *' both represent the binding position with M in Equation 401.

7. The organic light-emitting device according to claim 3, wherein, The emitting layer emits blue light.

8. A heterocyclic compound, said heterocyclic compound being represented by formula 1-1: Equation 1-1 in, In Equation 1-1, Depend on The part represented is one of equations A-11 to A-15: R 11 To R 14 and R 21 To R 24 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy groups and groups represented by formulas 7-1 to 7-10: Among them, in equations 7-1 to 7-10, iso-Bu represents isobutyl, t-Bu represents tert-butyl, and * indicates a bonding site with an adjacent atom. Among them, in equations A-11 to A-15, R 31 To R 35 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl and C1-C 20 Alkoxy R 101 R 102 R 104 R 105 R 107 and R 108 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. R 103 R 106 and R 109 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy b15 is an integer from 0 to 5, and * indicates a bonding site with an adjacent atom. Among them, R 11 To R 14 and R 21 To R 24 At least one of them is independently selected from the groups represented by formulas 7-1 to 7-10.

9. The heterocyclic compound according to claim 8, wherein, In R 11 To R 14 and R 21 To R 24 Among them, R 13 and R 23 At least one of them is independently selected from the groups represented by formulas 7-1 to 7-10, and the remaining substituents are all hydrogen.

10. The heterocyclic compound according to claim 8, wherein, In equations A-11 to A-15, R 31 To R 35 R 103 R 106 and R 109 Both are hydrogen.

11. The heterocyclic compound according to claim 8, wherein, In equations A-11 to A-15, R 101 R 102 R 104 R 105 R 107 and R 108 All are methyl groups.

12. The heterocyclic compound according to claim 8, wherein, Depend on The part represented is one of equations A-16 to A-20:

13. The heterocyclic compound according to claim 8, wherein, The heterocyclic compounds are selected from compounds 1 to 125:

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