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; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one heterocyclic compound represented by Formula 1. Formula 1.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0067861, filed with the Korean Intellectual Property Office on June 4, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of this disclosure relate to heterocyclic compounds and organic light-emitting devices comprising the heterocyclic compounds. Background Technology

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that, compared to other devices in the field, offer wide viewing angles, high contrast, short response times, and superior characteristics in terms of brightness, driving voltage, and response speed, while also producing full-color images.

[0005] An OLED may include a first electrode 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 through the hole transport region to the emitter layer, and electrons supplied from the second electrode can move through the electron transport region to the emitter layer. Charge carriers, such as holes and electrons, recombine in the emitter layer to generate excitons. These excitons transition from excited states (e.g., transitions or relaxations) to the ground state, thereby generating light. Summary of the Invention

[0006] One or more embodiments include heterocyclic compounds and organic light-emitting devices including the same.

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

[0008] According to one or more embodiments, the heterocyclic compound can be represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In Equation 1,

[0012] X can be any carbon group element other than silicon (Si).

[0013] Rings Ar1 to Ar4 can each be independently C5-C. 30 Carbocyclic groups or C2-C 30 Heterocyclic groups,

[0014] L1 can be selected from:

[0015] single key; and

[0016] Each was not replaced or was replaced by at least one Z 10a Substituted phenyl, naphthyl, anthraceneyl, pyrene, fluorenyl, dibenzofuranyl, and dibenzothiopheneyl,

[0017] a1 can be an integer selected from 1 to 10.

[0018] Y1 and Y2 can each be a single bond or a non-bond independently.

[0019] n can be an integer selected from 1 to 5.

[0020] R1 to R7 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2),

[0021] Z1 and Z 10a Each can be selected independently:

[0022] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0023] Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl and naphthyl;

[0024] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, -Si(Q) 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 ) and -B(Q 41 (Q) 42 );as well as

[0025] -Si(Q 51 (Q) 52 (Q) 53 -N(Q) 51 (Q) 52 ) and -B(Q 51 (Q) 52 ),

[0026] Q 41 To Q 43 and Q 51 To Q 53 Each can be selected independently:

[0027] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and

[0028] Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, and tert-pentyl: deuterium and C1-C 10 alkyl,

[0029] d1 and d2 can each be an integer selected from 1 to 4 independently.

[0030] d3 can be an integer selected from 1 to 3.

[0031] d4 to d7 can each be an integer selected from 1 to 20 independently.

[0032] d11 can be an integer selected from 1 to 4.

[0033] 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 The substituents of heteroaryl groups, substituted monovalent nonaromatic fused polycyclic groups, and substituted monovalent nonaromatic fused heterocyclic groups can be selected from:

[0034] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0035] Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, 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 60Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 );

[0036] Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 );as well as

[0037] -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 ),

[0038] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heterocyclic group; C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group; C6-C substituted with at least one group selected from deuterium, -F and cyano. 60 Aryl; biphenyl; and terphenyl.

[0039] According to one or more embodiments, an organic light-emitting device may include: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one heterocyclic compound represented by Formula 1. Attached Figure Description

[0040] Certain embodiments of this disclosure, as well as other aspects and features, will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:

[0041] Figure 1 A schematic cross-sectional view of an embodiment of the organic light-emitting device;

[0042] Figure 2 A schematic cross-sectional view of an embodiment of the organic light-emitting device;

[0043] Figure 3 A schematic cross-sectional view of an embodiment of the organic light-emitting device; and

[0044] Figure 4 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device. Detailed Implementation

[0045] Reference will now be made in more detail to embodiments, examples of which are shown in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this respect, embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described below only by reference to the figures 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 the disclosure, the expression "at least one of a, b, and c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0046] A heterocyclic compound represented by Formula 1:

[0047] Formula 1

[0048]

[0049] In Equation 1,

[0050] X can be any carbon group element other than silicon (Si). For example, X can be a group 14 element, except that X does not include Si.

[0051] In the implementation, X can be carbon (C), germanium (Ge), or tin (Sn).

[0052] Rings Ar1 to Ar4 can each be independently C5-C. 30 Carbocyclic groups or C2-C 30 Heterocyclic groups.

[0053] In some embodiments, cycloarium Ar1 to Ar4 may each be independently phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thiophene, furanyl, indolyl, benzoboranecyclopentadienyl, benzophoscyclopentadienyl, indene, benzothiophene, benzogermaniumcyclopentadienyl, benzothiophene, benzoselenyl, benzofuranyl, carbazole, dibenzoboranecyclopentadienyl Dienyl, dibenzophosphacyclopentadienyl, fluorenyl, dibenzothiophene, dibenzogermanium heterocyclopentadienyl, dibenzothiophene, dibenzoselenyl, dibenzofuranyl, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindolyl, azabenzoboron heterocyclopentadienyl, azabenzophosphacyclopentadienyl, azaindenyl, azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzo... Thiopheneyl, azibazoselenophenyl, azibazofuranyl, azibacarbazoyl, azibazoboronecyclopentadienyl, azibazophosphazopentadienyl, azibafluorenyl, azibazothiophenyl, azibazogeronylcyclopentadienyl, azibazothiophenyl, azibazoselenophenyl, azibazofuranyl, azibazothiophene 5-oxide, aziba-9H-fluoren-9-one, azibazothiophene 5,5-dioxide, pyridine The following groups are listed: pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.

[0054] In one or more embodiments, rings Ar1 to Ar4 may each be independently phenyl, naphthyl, fluorenyl, dibenzofuranyl or dibenzothiophene.

[0055] L1 can be selected from:

[0056] single key; and

[0057] Each was not replaced or was replaced by at least one Z 10a Substituted phenyl, naphthyl, anthraceneyl, pyrene, fluorenyl, dibenzofuranyl, and dibenzothiopheneyl.

[0058] In some implementations, L1 may be a single bond; or

[0059] A group represented by one of formulas 4-1 to 4-9:

[0060]

[0061] In equations 4-1 to 4-9, Z 21 and Z 22 Each can be targeted at Z 10a The descriptions are the same.

[0062] d31 can be an integer selected from 1 to 4.

[0063] d32 can be an integer selected from 1 to 6, and

[0064] * and *' each indicate the binding site with the adjacent atom.

[0065] a1 can be an integer selected from 1 to 10.

[0066] Y1 and Y2 can each be a single bond or a non-bonded bond independently (e.g., Y1 and Y2 can each be a single bond independently or can be omitted so that the individual benzene rings are not connected to each other through Y1 and Y2, and the individual connection sites of the benzene rings are bonded to hydrogen or other substituents).

[0067] In some implementations, Y1 can be a single bond, and Y2 can be a single bond;

[0068] Y1 can be nonbonded (for example, Y1 can be omitted so that the individual benzene rings are not connected to each other through Y1, and the individual connection sites of the benzene rings are bonded to hydrogen or other substituents), and Y2 can be single bonded.

[0069] Y1 can be a single bond, and Y2 can be a non-bonded bond (for example, Y2 can be omitted so that the individual benzene rings are not connected to each other through Y2, and the individual connection sites of the benzene rings are bonded to hydrogen or other substituents); or

[0070] Y1 can be non-bonded (e.g., Y1 can be omitted so that the individual benzene rings are not connected to each other through Y1, and the individual connection sites of the benzene rings are bonded to hydrogen or other substituents), and Y2 can be non-bonded (e.g., Y2 can be omitted so that the individual benzene rings are not connected to each other through Y2, and the individual connection sites of the benzene rings are bonded to hydrogen or other substituents).

[0071] In some implementations, Y1 may be a single bond, and Y2 may be a single bond.

[0072] n can be an integer selected from 1 to 5.

[0073] In some implementations, n can be 2 or greater.

[0074] R1 to R7 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C60 Alkyne group, 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2).

[0075] 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 The substituents of heteroaryl groups, substituted monovalent nonaromatic fused polycyclic groups, and substituted monovalent nonaromatic fused heterocyclic groups can be selected from:

[0076] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0077] Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, 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 fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 );

[0078] Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 );as well as

[0079] -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 ),

[0080] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heterocyclic group; C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group; C6-C substituted with at least one group selected from deuterium, -F and cyano. 60 Aryl; biphenyl; and terphenyl.

[0081] In some implementations, R1 to R7 can each be independently selected from:

[0082] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0083] Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl;

[0084] Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrylolyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzoxazole alkyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl and azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, indole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, Quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthroline, benzimidazolyl, benzofuranyl, benzothiophene, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 );

[0085] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2); and

[0086] Groups represented by formula 2-1:

[0087]

[0088] In Equation 2-1,

[0089] Z 11 and Z 12 Each can be understood by referring to the description of Z1 provided in this article.

[0090] d21 and d22 can each be independently integers selected from 1 to 4, * indicates the binding site with adjacent atoms, and

[0091] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be selected independently:

[0092] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and

[0093] Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, and triazinyl: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl.

[0094] R1 to R7 can be selected independently from:

[0095] Hydrogen, deuterium, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0096] Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl and naphthyl;

[0097] Each of the following is either unsubstituted or substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, isoindolyl, indolyl, indazole, purinyl, carbazole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole and dibenzocarbazole: deuterium, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, isoindolyl, indolyl, indazole, purine, carbazole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 );

[0098] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) and -B(Q1)(Q2); and

[0099] Groups represented by formula 2-1:

[0100]

[0101] In Equation 2-1,

[0102] Z 11 and Z 12 Each can be understood by referring to the description of Z1 provided in this article.

[0103] d21 and d22 can each be an integer selected from 1 to 4 independently.

[0104] *Indicates the binding site with adjacent atoms, and

[0105] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be selected independently:

[0106] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and

[0107] Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl: deuterium, C1-C 10 Alkyl, phenyl, and biphenyl.

[0108] Z1 and Z 10a Each can be selected independently:

[0109] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0110] Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl and naphthyl;

[0111] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, -Si(Q) 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 ) and -B(Q 41 (Q) 42 );as well as

[0112] -Si(Q 51 (Q) 52 (Q) 53 -N(Q) 51 (Q) 52 ) and -B(Q 51 (Q) 52 ),

[0113] Q 41 To Q 43 and Q 51 To Q 53 Each can be selected independently:

[0114] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and

[0115] Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, and tert-pentyl: deuterium and C1-C 10 alkyl.

[0116] d1 and d2 can each be an integer selected from 1 to 4 independently.

[0117] d3 is an integer selected from 1 to 3.

[0118] d4 to d7 can each be an integer selected from 1 to 20 independently, and

[0119] d11 can be an integer selected from 1 to 4.

[0120] In some embodiments, the heterocyclic compound represented by Formula 1 can be represented by Formula 1-1:

[0121] Formula 1-1

[0122]

[0123] In Equation 1-1, X, rings Ar1 to Ar4, L1, a1, Y1, Y2, n, R1 to R7, Z1, d1 to d7, and d11 can be understood by referring to the descriptions of X, rings Ar1 to Ar4, L1, a1, Y1, Y2, n, R1 to R7, Z1, d1 to d7, and d11 provided elsewhere in this document.

[0124] In some implementations, Equation 1 is composed of The part to be represented can be one of equations 3-1 to 3-3:

[0125]

[0126] In Equations 3-1 to 3-3, d7 can be an integer selected from 1 to 4, X, rings Ar1 to Ar3, L1, a1, R4 to R7 and d4 to d7 can be understood by referring to the descriptions of X, rings Ar1 to Ar3, L1, a1, R4 to R7 and d4 to d7 provided herein, and * indicates the binding site with adjacent atoms.

[0127] In the implementation method, Equation 1 is composed of The part to be represented can be one of equations 5-1 to 5-36:

[0128]

[0129]

[0130] In Equations 5-1 to 5-36, Y2 can be understood by referring to the description of Y2 provided in this article, and

[0131] R 11 To R 14 Each can be understood by referring to the description of R1 provided in this article, and R... 21 To R 24 Each can be understood by referring to the description of R2 provided in this article, provided that R... 11 To R 14 and R 21 To R 24 Each of them may not be hydrogen.

[0132] In some implementations, R4 to R7 may each be non-hydrogen;

[0133] R7 can be hydrogen, and at least one of R4 to R6 can be non-hydrogen; or

[0134] R4 to R6 can each be hydrogen, and R7 can be non-hydrogen.

[0135] In some embodiments, the heterocyclic compound represented by Formula 1 may be represented by one of Formulas 6-1 to 6-4:

[0136]

[0137]

[0138] In Equations 6-1 and 6-4, L1, a1, n, R1 to R7, and Z1 can be understood by referring to the descriptions of L1, a1, n, R1 to R7, and Z1 provided in this document.

[0139] d1, d2, d7, and d11 can each be an integer selected from 1 to 4 independently.

[0140] d3 can be an integer selected from 1 to 3, and

[0141] d4 to d6 can each be an integer selected from 1 to 5 independently.

[0142] In some embodiments, the heterocyclic compound represented by Formula 1 may be selected from compounds 1 to 80, but the embodiments are not limited thereto:

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] Heterocyclic compounds represented by Formula 1 may include structures in which four cyclic groups replace carbon group elements (atom X in Formula 1) and structures in which carbazole rings or amino groups are continuously linked by CN bonds (e.g., bonded to each other).

[0149] Since Formula 1 can include the structure in which four cyclic groups substitute for the carbon group element (atom X in Formula 1), Formula 1 can be stable in terms of energy levels and have high triplet energy due to the empty d-orbitals (e.g., the empty d-orbitals of atom X). Depending on the period of atom X (e.g., depending on the row of the periodic table occupied by atom X), the carbon group element (atom X) can have different bond energies and different migration properties.

[0150] Since Formula 1 may include a structure in which carbazole rings or amino groups are continuously linked by CN bonds (e.g., bonded to each other), Formula 1 can perform well in terms of improved driving voltage, luminous efficiency and energy transfer when combined with phosphorescent dopants.

[0151] Therefore, electronic devices using heterocyclic compounds represented by Formula 1, such as organic light-emitting devices, can have low driving voltage, high maximum quantum yield, high efficiency, and long lifetime.

[0152] The method for synthesizing the heterocyclic compound represented by Formula 1 should be readily apparent to those skilled in the art upon reference to the embodiments described herein.

[0153] At least one heterocyclic compound represented by Formula 1 may be included between a pair of electrodes in an organic light-emitting device. In some embodiments, the heterocyclic compound represented by Formula 1 may be included in an emitting layer. In some embodiments, the heterocyclic compound represented by Formula 1 may be used as a material for forming a capping layer on the outside of a pair of electrodes in an organic light-emitting device.

[0154] According to one or more embodiments, an organic light-emitting device may include: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one heterocyclic compound represented by Formula 1.

[0155] As used herein, the statement "(organic layer) comprises at least one heterocyclic compound" can be interpreted as meaning "(organic layer) may comprise one heterocyclic compound of Formula 1 or two different heterocyclic compounds of Formula 1".

[0156] For example, the organic layer may include only compound 1 as a heterocyclic compound. In this embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In some embodiments, the organic layer may include compounds 1 and 2 as heterocyclic compounds. In this embodiment, compounds 1 and 2 may be included in the same layer (e.g., both compounds 1 and 2 may be included in the emitting layer) or in different layers (e.g., compound 1 may be included in the emitting layer and compound 2 may be included in the electron transport layer).

[0157] In some implementations, the first electrode may be the anode.

[0158] The second electrode can be a cathode, and

[0159] The organic layer may include heterocyclic compounds represented by Formula 1, and

[0160] 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.

[0161] In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or a combination thereof, and

[0162] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0163] In some embodiments, the emitter layer may include a heterocyclic compound represented by Formula 1.

[0164] In some implementations...

[0165] The emitter layer may include a host and dopants.

[0166] The host may be different from the dopant.

[0167] The content of the host can be greater than the content of the dopant, and

[0168] The host may include a heterocyclic compound represented by Formula 1.

[0169] In some implementations, the emitting layer may emit blue light or blue-green light.

[0170] In some implementations, the dopant may emit blue or blue-green light having a maximum emission wavelength in the range of about 400 nanometers (nm) to about 500 nm.

[0171] In some embodiments, the dopant may include a transition metal and may not include transition metal-nitrogen bonds and transition metal-oxygen bonds.

[0172] In some implementations, the dopant may include a transition metal and a coordination bond (e.g., a coordination covalent bond or a coordination valence bond) between the transition metal and the carbon atom.

[0173] In some embodiments, the dopant may include a transition metal and carbon-carbon bonds between the transition metal and carbon atoms in the form of carbene.

[0174] In some embodiments, the dopant may include a transition metal and a ligand, and the ligand may include carbon atoms in the form of carbene.

[0175] In some embodiments, the heterocyclic compound represented by Formula 1 can be used as a material for a capping layer on the outside of a pair of electrodes in an organic light-emitting device.

[0176] In some implementations, the electronic device may include an organic light-emitting device.

[0177] In some embodiments, the electronic device may further include a thin-film transistor.

[0178] The thin-film transistor may include a source electrode and a drain electrode, and

[0179] The first electrode of an organic light-emitting device can be electrically coupled to either the source electrode or the drain electrode.

[0180] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first and second electrodes in 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.

[0181] In some embodiments, the organic light-emitting device may have i) a first electrode / organic layer / second electrode / second capping layer structure, ii) a first capping layer / first electrode / organic layer / second electrode structure, or iii) a first capping layer / first electrode / organic layer / second electrode / second capping layer structure, wherein the layers of each structure are stacked sequentially in the order described herein. At least one of the first capping layer and the second capping layer may include a heterocyclic compound represented by Formula 1.

[0182] Figure 1 Description

[0183] Figure 1 A schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment is shown. The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.

[0184] The following text will combine Figure 1The structure of the organic light-emitting device 10 according to the embodiment and the method of manufacturing the organic light-emitting device according to the embodiment are described.

[0185] First electrode 110

[0186] 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, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0187] The first electrode 110 can be formed 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 for forming the first electrode 110 can be selected from materials with high work function that facilitate hole injection.

[0188] The first electrode 110 may 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 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments are not limited thereto. In some embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, at least one material 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 may be used as the material used to form the first electrode 110, but the embodiments are not limited thereto.

[0189] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. In some embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the embodiments are not limited to this.

[0190] Organic layer 150

[0191] The organic layer 150 may be on the first electrode 110. The organic layer 150 may include an emitter layer.

[0192] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.

[0193] Hole transport region in organic layer 150

[0194] The hole transport region may have i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single layer) of a single layer of a single material, or iii) a multi-layer structure having multiple layers comprising multiple different materials.

[0195] The hole transport region may include at least one selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.

[0196] For example, the hole transport region may have a single-layer structure including a single layer (including multiple different materials) or a multi-layer structure, such as a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure are stacked sequentially on the first electrode 110 in the order described therein, but the implementation is not limited thereto.

[0197] 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), CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), compounds represented by Formula 201, and compounds represented by Formula 202:

[0198]

[0199]

[0200] Among them, in equations 201 and 202,

[0201] 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-C60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0202] L 205 Optional from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0203] xa1 to xa4 can each be an integer selected from 0 to 3 independently.

[0204] xa5 can be an integer selected from 1 to 10, and

[0205] 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0206] In some implementations, in formula 202, R 201 and R 202 Optionally linked via a single bond, dimethyl-methylene, or diphenyl-methylene, and R 203and R 204 It can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond.

[0207] In some embodiments, in formulas 201 and 202, L 201 To L 205 Each can be selected independently:

[0208] Phenylidene, pentylene, indene, naphthyl, azulene, heptadene, acenaphthene, fluorenene, spiro-difluorenene, benzo[a]fluorenene, dibenzo[a]fluorenene, phenanthroline, anthracene, fluorenyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenylene, fenenyl, perylene, perylene Pentofenyl, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophylene, thiophenyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzothiophenyl, and pyridylene; and

[0209] Each of the following is substituted with at least one of the following: phenylene, pentyleneylene, indenylene, naphthylene, azoxylene, heptyleneneylene, acenaphthene, fluorenene, spiro-difluorenene, benzo[a]fluorenene, dibenzo[a]fluorenene, phenenenyl, phenanthrene, anthracene, fluorenyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenylene, fentanyl, perylene, pentylene, hexaphenylene, etc. Pentaphenyl, rubidinyl, mycoyl, oleophyllyl, thiophenyl, furanyl, carbazoyl, indoleyl, isoydinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q)31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),

[0210] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0211] In one or more embodiments, xa1 to xa4 may each be 0, 1 or 2 independently.

[0212] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0213] In one or more embodiments, R 201 To R 204 and Q 201 Each of these can be independently selected from: phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-glycol, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, styryl, peryl, pentanyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, ovoleyl, thiopheneyl, furanyl, carbazoleyl, indoleyl, isoyindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl; and

[0214] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptanenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, framyyl, peryleneyl, penfenyl, hexaphenyl. Pentaphenyl, rutinyl, keratyl, ovoleylphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),

[0215] Q 31 To Q 33 You can refer to the Q provided in this article. 31 To Q 33 To understand this, we need to refer to the description.

[0216] In one or more embodiments, in formula 201, R 201 To R 203 At least one of them can be selected from:

[0217] Fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and

[0218] Each of the following is substituted with at least one of the following fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl.

[0219] However, the implementation methods are not limited to this.

[0220] In one or more embodiments, in formula 202, i)R 201 and R 202 It can be linked by a single bond, and / or ii)R 203 and R 204 It can be bound by a single bond.

[0221] In one or more embodiments, in formula 202, R 201 To R204 At least one of them can be selected from:

[0222] Carbazolyl; and

[0223] The carbazoyl group is substituted with at least one of the following: 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, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl, but the embodiments are not limited thereto.

[0224] The compound represented by formula 201 can be represented by formula 201-1:

[0225] Formula 201-1

[0226]

[0227] In some embodiments, the compound represented by formula 201 may be represented by formula 201-2, but the embodiments are not limited thereto:

[0228] Formula 201-2

[0229]

[0230] In some embodiments, the compound represented by formula 201 may be represented by formula 201-2(1), but the embodiments are not limited thereto:

[0231] Equation 201-2(1)

[0232]

[0233] The compound represented by formula 201 can be represented by formula 201A:

[0234] Formula 201A

[0235]

[0236] In some embodiments, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments are not limited thereto:

[0237] Formula 201A(1)

[0238]

[0239] In some embodiments, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments are not limited thereto:

[0240] Formula 201A-1

[0241]

[0242] In some embodiments, the compound represented by formula 202 may be represented by formula 202-1:

[0243] Formula 202-1

[0244]

[0245] In one or more embodiments, the compound represented by formula 202 may be represented by formula 202-1(1):

[0246] Equation 202-1(1)

[0247]

[0248] In some embodiments, the compound represented by formula 202 may be represented by formula 202A:

[0249] Formula 202A

[0250]

[0251] In some embodiments, the compound represented by formula 202 may be represented by formula 202A-1:

[0252] Formula 202A-1

[0253]

[0254] In equations 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

[0255] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 You can refer to the L provided in this article respectively 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 To understand from the description,

[0256] L 205 The choice can be made from phenylene and fluorene groups.

[0257] X211 Selectable from O, S, and N(R) 211 ),

[0258] X 212 Selectable from O, S, and N(R) 212 ),

[0259] R 211 and R 212 Each can refer to the R provided in this article. 203 To understand from the description, and

[0260] 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, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indyl, naphthyl, azuleyl, heptenyl, indole-based, acenaphtheyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, furanyl, peryl, pentanyl, hexaphenyl, pentaphenyl, rubidyl, kosyl, ovoidyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[carbazoyl], dibenzo[carbazoyl], dibenzothiopheneyl, and pyridyl.

[0261] The hole transport region may include at least one compound selected from compounds HT1 to HT48, but the implementation is not limited thereto:

[0262]

[0263]

[0264]

[0265]

[0266] The thickness of the hole transport region can be approximately 100 angstroms. to approximately Within the scope, and in some implementations, 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 the scope, and in some implementations, in approximately to approximately Within a certain range, and the thickness of the hole transport layer can be approximately... to approximately Within the scope, and in some implementations, in approximately to approximately Within the aforementioned range, when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are all within any of the aforementioned ranges, excellent hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0267] The emission assist layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer. The electron blocking layer can reduce or eliminate the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can include the materials described above.

[0268] p-dopants

[0269] The hole transport region may include a charge-generating material and the aforementioned materials to improve the conductivity of the hole transport region. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.

[0270] Charge-generating materials may include, for example, p-doped agents.

[0271] In some implementations, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant may be -3.5 eV or lower.

[0272] p-dopers may include at least one selected from quinone derivatives, metal oxides and cyano-containing compounds, but the implementation is not limited thereto.

[0273] In some implementations, the p-doper may include:

[0274] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);

[0275] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0276] 1,4,5,8,9,12-hexaazatriphenylene-hexanitrile (HAT-CN); and

[0277] The compound represented by formula 221, but the implementation is not limited to this:

[0278]

[0279] In Equation 221,

[0280] R221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein the group selected from R 221 To R 223 At least one of them may include at least one substituent selected from: cyano, -F, -Cl, -Br, -I, C1-C substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and -I-substituted C1-C 20 alkyl.

[0281] Emission layer in organic layer 150

[0282] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned into 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. The stacked structure may include two or more layers selected from red, green, and blue emitting layers. The two or more layers may be in direct contact with each other (e.g., physical contact). In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emitting layer may include two or more materials. The two or more materials may include red emitting materials, green emitting materials, or blue emitting materials. The two or more materials may be mixed with each other in a single layer. Mixing two or more materials with each other in a single layer can emit white light.

[0283] The emitter layer may include a heterocyclic compound represented by Formula 1.

[0284] The emitting layer may include a host and a light-emitting material. The light-emitting material may include at least one of phosphorescent dopant, fluorescent dopant, and quantum dot.

[0285] Based on 100 parts by weight of the main body, the amount of dopant in the emitter layer is typically in the range of about 0.01 parts by weight to about 15 parts by weight, but the implementation is not limited to this.

[0286] In some implementations, the emitting layer may emit blue light or blue-green light.

[0287] In some embodiments, the heterocyclic compound represented by Formula 1 emits blue or blue-green light having a maximum emission wavelength in the range of about 400 nm to about 500 nm.

[0288] The thickness of the emission layer can be approximately to approximately Within the scope, and in some implementations, in approximately to approximately Within the aforementioned range, improved luminescence characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within any of the aforementioned ranges.

[0289] The main body in the emission layer

[0290] The host may be different from the dopant, and the content (e.g., amount or weight) of the host may be greater than the content (e.g., amount or weight) of the dopant, and the host may include a heterocyclic compound represented by Formula 1.

[0291] The main body may further include a compound represented by formula 301:

[0292] Formula 301

[0293] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0294] In Equation 301,

[0295] Ar 301 C5-C can be self-substituted or unsubstituted. 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0296] xb11 can be 1, 2, or 3.

[0297] L 301 C3-C can be self-substituted or unsubstituted. 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 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0298] xb1 can be an integer selected from 0 to 5.

[0299] R 301 The group 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 group, substituted or unsubstituted C1-C 60 Alkyl, 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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 ),and

[0300] xb21 can be an integer selected from 1 to 5.

[0301] 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 implementation methods are not limited to these.

[0302] In some implementations, in formula 301, Ar 301 Optional from:

[0303] Naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenatenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, dibenzofuranyl, and dibenzothiopheneyl; and

[0304] Each of the following is substituted with at least one of the following: naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, dibenzofuranyl, and dibenzothiophene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, 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 ),

[0305] 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 implementation methods are not limited to these.

[0306] When xb11 in equation 301 is 2 or greater, at least two Ar 301 It can be bound by a single bond.

[0307] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:

[0308] Formula 301-1

[0309]

[0310] Formula 301-2

[0311]

[0312] Among them, in equations 301-1 and 301-2,

[0313] A 301 To A 304 Each of these compounds can be independently selected from phenyl, naphthyl, phenanthryl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyridyl, pyrimidinyl, indene, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], indolyl, carbazole, benzo[carbazole], dibenzo[carbazole], furanyl, benzo[furanyl], dibenzo[furanyl], naphthiofuranyl, benzo[naphthiofuranyl], dinaphthiofuranyl, thiophene, benzo[naphthiofuranyl], and dinaphthiofuranyl.

[0314] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0315] 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 ),

[0316] xb22 and xb23 can each be 0, 1, or 2 independently.

[0317] L 301 xb1, R 301 and Q 31 To Q 33 You can refer to the L provided in this article respectively 301 xb1, R 301 and Q 31 To Q 33 To understand from the description,

[0318] L 302 To L 304 Each can refer to the L provided in this article. 301 To understand from the description,

[0319] xb2 to xb4 can each be understood by referring to the description of xb1 provided in this document, and

[0320] R 302 To R 304 Each can refer to the R provided in this article. 301 To understand this, we need to refer to the description.

[0321] In some embodiments, in formulas 301, 301-1, and 301-2, L 301 To L 304 Each can be selected independently:

[0322] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiopheneyl Azolyl, iminothiazolyl, iminooxazolyl, iminooxazolyl, iminothiadiazolyl, iminooxadiazolyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, triazinyl, iminopyrinyl, iminopyrinyl, iminopyrinyl, benzoquinolineyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, and iminopyrazoleyl; and

[0323] Each of the following is substituted with at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxadiazolyl. Azolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisothiazolyl, benzisisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisisothiazolyl, 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 ),

[0324] Q31 To Q 33 You can refer to the Q provided in this article. 31 To Q 33 To understand this, we need to refer to the description.

[0325] In some embodiments, in formulas 301, 301-1, and 301-2, R 301 To R 304 Each can be selected independently:

[0326] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazole , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl; and

[0327] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl Oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisisothiazolyl, 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 ),

[0328] Q 31 To Q 33 You can refer to the Q provided in this article. 31 To Q 33 To understand this, we need to refer to the description.

[0329] In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include a beryllium (Be) complex (e.g., compound H55), a magnesium (Mg) complex, or a zinc (Zn) complex.

[0330] 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-carbazolyl)benzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments are not limited thereto:

[0331]

[0332]

[0333]

[0334] Phosphorescent dopants in the emission layer of organic layer 150

[0335] Phosphorescent dopants may include organometallic complexes represented by formula 401:

[0336] Formula 401

[0337] M(L 401 ) xc1 (L 402 ) xc2

[0338] In Equation 401,

[0339] 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).

[0340] L 401 The ligand can be represented by the free formula 402, and xc1 can be 1, 2, or 3, and when xc1 is 2 or greater, at least two L... 401 They can be the same or different from each other.

[0341] L 402 It can be an organic ligand, and xc2 can be an integer selected from 0 to 4, and when xc2 is 2 or greater, at least two L... 402 They can be the same or different from each other.

[0342] Formula 402

[0343]

[0344] In Equation 402, X 401 To X 404 They can be nitrogen or carbon independently.

[0345] X 401 and X 403 They can combine with each other via single or double bonds, X 402 and X 404 They can combine with each other via single or double bonds.

[0346] A 401 and A 402 Each can be independently classified as C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0347] X 405It 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 Each can be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,

[0348] X 406 It can be a single bond, O, or S.

[0349] R 401 and R 402 Each 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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-C10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0350] xc11 and xc12 can each independently be an integer selected from 0 to 10, and

[0351] In Equation 402, * and *' each indicate the binding site with M in Equation 401.

[0352] In some implementations, in formula 402, A 401 and A 402 Each of the following can be independently selected from phenyl, naphthyl, fluorenyl, spiro-difluorenyl, indyl, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, carbazole, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiophene, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophene.

[0353] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each can be nitrogen.

[0354] In the implementation, in formula 402, R 401 and R 402 Each can be selected independently:

[0355] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0356] Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl;

[0357] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0358] Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornel, norbornel-enyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornel, norbornel-alkenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl; and

[0359] -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 ),

[0360] 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 implementation methods are not limited to these.

[0361] In one or more embodiments, when xc1 in equation 401 is 2 or greater, at least two L 401 The two A's in 401 Optionally via X as a linking group 407 Connect; or two A's 402 Optionally via X as a linking group 408 Linkage (see compounds PD1 through PD4 and PD7 in this article). X 407 and X 408Each can be independently selected from single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' and *-C(Q 413 )=C(Q 414 )-*', where Q 413 and Q 414 Each can be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, but the implementation methods are not limited to these.

[0362] L in Equation 401 402 It can be any suitable monovalent, divalent, or trivalent organic ligand. For example, L 402 The components may be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., pyridine carboxylates), -C (=O), isonitriles, -CN, and phosphorus groups (e.g., phosphine or phosphites), but the implementation is not limited thereto.

[0363] In some embodiments, the phosphorescent dopant may include, for example, at least one selected from compounds PD1 to PD25, but the embodiments are not limited thereto:

[0364]

[0365] Fluorescent dopants in the emission layer

[0366] In some embodiments, the fluorescent dopant may include a heterocyclic compound represented by Formula 1.

[0367] Fluorescent dopants may further include aromatic amine compounds or styrene amine compounds.

[0368] In some embodiments, the fluorescent dopant may further comprise a compound represented by formula 501:

[0369] Formula 501

[0370]

[0371] In Equation 501,

[0372] Ar 501 C5-C can be self-substituted or unsubstituted. 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0373] L 501 To L 503Each 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 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0374] xd1 to xd3 can each be an integer selected from 0 to 3 independently.

[0375] 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and

[0376] xd4 can be an integer selected from 1 to 6.

[0377] In some implementations, in formula 501, Ar 501 Optional from:

[0378] Naphthyl, heptadeninyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, and indoxanthryl; and

[0379] Each of the following substituted groups is selected from at least one of the following: naphthyl, heptalenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, ind[a]anthryl, and ind[a]phenanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0380] In the implementation, in formula 501, L 501 and L 503 Each can be selected independently from:

[0381] Phenylidene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, and pyridylene; and

[0382] Each of the following substituted groups is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.

[0383] In the implementation, in formula 501, R 501 and R 502 Each can be selected independently from:

[0384] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and

[0385] Each of the following substituted groups is selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazoleyl, indolyl, isoindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazoleyl, dibenzo[a]carbazoleyl, dibenzothiopheneyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, and -Si(Q) 31 (Q) 32 (Q) 33 ),

[0386] Q 31 To Q 33 Optional from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0387] In one or more embodiments, xd4 in Formula 501 may be 2, but the embodiments are not limited thereto.

[0388] In some embodiments, the fluorescent dopant may be selected from compounds FD1 to FD22:

[0389]

[0390]

[0391] In some embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments are not limited thereto:

[0392]

[0393] quantum dots

[0394] The emitting layer in the organic light-emitting device included in the embodiments of this disclosure may include quantum dot materials.

[0395] Quantum dots are particles with crystal structures ranging from a few to tens of nanometers in size. A quantum dot can contain hundreds to thousands of atoms.

[0396] Because quantum dots are extremely small, the quantum confinement effect occurs. The quantum confinement effect is a phenomenon where the band gap of an object increases as it becomes smaller than a nanometer. Therefore, when light with energy greater than the wavelength of the quantum dot's band gap is incident on the quantum dot, the quantum dot is excited by absorbing the light, emitting light of a set or specific wavelength, and falling back to its ground state. In this case, the wavelength of the emitted light can have a value corresponding to the band gap.

[0397] The nucleus of a quantum dot may 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.

[0398] Group II-VI compounds may be selected from: binary compounds selected from the group consisting of: CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; and ternary compounds selected from the group consisting of: CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, ... CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from the group consisting of: CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0399] Group III-VI compounds may include binary compounds such as In2S3 and / or In2Se3; ternary compounds such as InGaS3 and / or InGaSe3; or any combination thereof.

[0400] Group III-V compounds may be selected from: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and mixtures thereof. Group III-V semiconductor compounds may further include Group II metals (e.g., InZnP).

[0401] Group IV-VI compounds may be selected from: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0402] In this embodiment, binary, ternary, or quaternary compounds may exist in the particles at a uniform (e.g., substantially uniform) concentration, or may exist in the same particle by being partially divided into different concentrations. Furthermore, one quantum dot may have a core-shell structure surrounding another quantum dot. The interface between the core and shell may have a concentration gradient, wherein the concentration of the element present in the shell decreases along the direction toward the core.

[0403] In some embodiments, quantum dots may have a core-shell structure, comprising a core containing the aforementioned nanocrystals and a shell surrounding the core. The shell of the quantum dot may act as a protective layer to prevent or reduce chemical denaturation of the core to maintain semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be monolayer or multilayer. The interface between the core and the shell may have a concentration gradient, wherein the concentration of elements present in the shell decreases along the direction toward the core. Examples of shells for quantum dots include metal oxides and / or nonmetal oxides, semiconductor compounds, or combinations thereof.

[0404] In some embodiments, the metal oxide or non-metal oxide may be a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO, or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4, but the embodiments are not limited thereto.

[0405] In addition, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP and / or AlSb, but the implementation is not limited to these.

[0406] Quantum dots can have a full width at half maximum (FWHM) of emission wavelengths of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of the emission wavelength spectrum of a quantum dot is within any of the aforementioned ranges, color purity or color reproducibility can be improved. Furthermore, because light emitted through a quantum dot is emitted in all directions, the optical viewing angle can be improved.

[0407] Furthermore, quantum dots can take any suitable form commonly used in the field, and there are no particular limitations. Quantum dots can be spherical, conical, multi-armed, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles, etc.

[0408] Quantum dots can emit light colors that can be controlled by adjusting their particle size. Therefore, quantum dots can have a variety of suitable emission colors, such as blue, red, or green.

[0409] Electron transport region in organic layer 150

[0410] The electron transport region may have i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single layer of a single material, or iii) a multi-layer structure having multiple layers of a single material, each of the multiple layers having multiple different materials.

[0411] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the implementation is not limited thereto.

[0412] In some embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure are stacked sequentially on the emitter layer in the order described herein, but the embodiments are not limited thereto.

[0413] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, electron transport layer and / or electron injection layer in the electron transport region) may include a heterocyclic compound represented by Formula 1.

[0414] In some embodiments, the electron transport region may include a heterocyclic compound represented by Formula 1 and may further include a metal-free compound containing at least one ring of nitrogen with π electron depletion.

[0415] As used herein, "a nitrogen ring containing π-electron depleted" refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic groups.

[0416] For example, "a ring containing nitrogen with depleted π electrons" can be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group wherein at least two 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are fused 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 Heterocyclic groups with fused (e.g., combined) carbocyclic groups.

[0417] Examples of nitrogen rings containing depleted π electrons may include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazoline, cyclophosphine, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benziisothiazole, benzoxazole, benziisoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but the implementation is not limited thereto.

[0418] In some embodiments, the electron transport region may include a compound represented by formula 601:

[0419] Formula 601

[0420] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0421] In Equation 601,

[0422] Ar 601 C5-C can be self-substituted or unsubstituted. 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 Heterocyclic groups,

[0423] xe11 can be 1, 2, or 3.

[0424] L 601 C3-C can be self-substituted or unsubstituted. 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 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0425] xe1 can be an integer selected from 0 to 5.

[0426] R 601 C3-C can be self-substituted or unsubstituted. 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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 ),

[0427] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0428] xe21 can be an integer selected from 1 to 5.

[0429] In some implementations, Ar is selected in quantities of xe11. 601 and R with a quantity of xe21 601 At least one of them may include a nitrogen ring containing π electrons depleted.

[0430] In some implementations, in formula 601, Ar 601 Optional from:

[0431] Phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxane, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridyl Azinyl, indazole, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and

[0432] Each of the following is substituted with at least one of the following: phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxaneyl, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, or purine. Quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, 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 ),

[0433] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0434] When xe11 in equation 601 is 2 or greater, at least two Ar 601 It can be bound by a single bond.

[0435] In one or more embodiments, Ar in Formula 601 601 It can be anthracene.

[0436] In some embodiments, the compound represented by formula 601 may be represented by formula 601-1:

[0437] Formula 601-1

[0438]

[0439] In Equation 601-1,

[0440] 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 ), selected from X 614 To X 616 At least one of them can be N,

[0441] L 611 To L 613 Each can be independently referred to the L provided in this article. 601 To understand from the description,

[0442] xe611 to xe613 can each be understood independently by referring to the description of xe1 provided in this document.

[0443] R 611 To R 613 Each can be independently obtained by referring to the R provided in this article. 601 To understand from the description, and

[0444] 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.

[0445] In some embodiments, in formulas 601 and 601-1, L 601 and L 611 To L 613 Each can be selected independently:

[0446] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiopheneyl Azolyl, iminothiazolyl, iminooxazolyl, iminooxazolyl, iminothiadiazolyl, iminooxadiazolyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, triazinyl, iminopyrinyl, iminopyrinyl, iminopyrinyl, benzoquinolineyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, and iminopyrazoleyl; and

[0447] Each of the following is substituted with at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxadiazolyl. Azolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisothiazolyl, benzisisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazole 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, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.

[0448] However, the implementation methods are not limited to this.

[0449] In one or more embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each be 0, 1 or 2 independently.

[0450] In one or more embodiments, in formula 601 and formula 601-1, R 601 and R 611 To R 613 Each can be selected independently:

[0451] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0452] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl Oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, pyridyl, 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, benzoxoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and

[0453] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),

[0454] Q 601 and Q 602 You can refer to the Q provided in this article. 601 and Q 602 To understand this, we need to refer to the description.

[0455] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but the implementation is not limited thereto:

[0456]

[0457]

[0458]

[0459] In some 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), NTAZ, diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1), and 2,2',2"-(1,3,5-benzyltriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi):

[0460]

[0461] The thickness of the buffer layer, hole blocking layer, or electronic control layer can be independently set at approximately [value missing]. to approximately Within the scope, and in some implementations, in approximately to approximately Within the aforementioned range, when the thickness of the buffer layer, hole blocking layer, or electronic control layer is within any of the aforementioned ranges, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without a significant increase in driving voltage.

[0462] The thickness of the electron transport layer can be approximately to approximately Within the scope, and in some implementations, in approximately to approximately Within any of the aforementioned ranges, excellent electron transport characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron transport layer is within any of the aforementioned ranges.

[0463] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.

[0464] 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 lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions. Alkaline earth metal complexes may include metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. Each ligand coordinated to the metal ions of the alkali metal complex and alkaline earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments are not limited thereto.

[0465] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or compound ET-D2:

[0466]

[0467] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0468] The electron injection layer may have i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material), ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes multiple different materials, or iii) a multi-layer structure having multiple layers, each including multiple different materials.

[0469] 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 a combination thereof.

[0470] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In some embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments are not limited thereto.

[0471] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0472] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0473] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.

[0474] 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 some embodiments, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments are not limited thereto.

[0475] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1) and Ba x Ca 1-x O (where 0 < x < 1). In some embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments are not limited thereto.

[0476] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In some embodiments, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments are not limited thereto.

[0477] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may each comprise ions of the aforementioned alkali metal, alkaline earth metal, and rare earth metal. Each ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments are not limited thereto.

[0478] The electron injection layer may include (for example, composed of) alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof as described above. In some embodiments, the electron injection layer may further include organic materials. When the electron injection layer further includes organic materials, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof may be uniformly or non-uniformly dispersed in a matrix comprising the organic material.

[0479] The thickness of the electron injection layer can be approximately to approximately Within the scope, and in some implementations, in approximately to approximately Within the aforementioned range, excellent electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron injection layer is within any of the aforementioned ranges.

[0480] Second electrode 190

[0481] The second electrode 190 may be on the organic layer 150. In an embodiment, the second electrode 190 may be a cathode (e.g., an electron injection electrode). In this embodiment, the material used to form the second electrode 190 may be a material with low work function, such as, for example, a metal, an alloy, a conductive compound, or a combination thereof.

[0482] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), silver-magnesium (Ag-Mg), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, and IZO, but the embodiments are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0483] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0484] Figures 2 to 4 Description

[0485] See Figure 2 The organic light-emitting device 20 has a structure comprising a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, wherein the layers are stacked sequentially in the order described herein. See also Figure 3 The organic light-emitting device 30 has a structure comprising a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, wherein the layers are stacked sequentially in the order described herein. See also Figure 4 The organic light-emitting device 40 has a structure of a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, wherein the layers are stacked sequentially in the order described herein.

[0486] Figures 2 to 4 The first electrode 110, organic layer 150, and second electrode 190 shown herein can be coupled with Figure 1 Those shown in the image are essentially the same.

[0487] In organic light-emitting devices 20 and 40, light emitted from the emitting layer in organic layer 150 can pass through the first electrode 110 (which may be a semi-transparent electrode or a transmissive electrode) and the first capping layer 210 to the outside. In organic light-emitting devices 30 and 40, light emitted from the emitting layer in organic layer 150 can pass through the second electrode 190 (which may be a semi-transparent electrode or a transmissive electrode) and the second capping layer 220 to the outside.

[0488] Based on the principle of constructive interference, the first capping layer 210 and the second capping layer 220 can improve the external luminescence efficiency.

[0489] The first capping layer 210 and the second capping layer 220 may each independently include organic matter, inorganic matter, or any combination thereof.

[0490] At least one of the first capping layer 210 and the second capping layer 220 may independently include a material selected from carbocyclic compounds, heterocyclic compounds, amino-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, and silicon-based inorganic materials such as SiON and SiN. x or SiO xAt least one of silicon-based organic substances, acrylic compounds, and epoxy compounds. Carbocyclic compounds, heterocyclic compounds, and amine-containing compounds may optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In some embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.

[0491] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.

[0492] 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 are not limited thereto:

[0493]

[0494] The above has been referenced. Figures 1 to 4 Organic light-emitting devices have been described, but the implementation methods are not limited thereto.

[0495] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in a set or specific area using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0496] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are each formed by vacuum deposition, the deposition temperature can be from about 100°C to about 500°C, depending on the materials to be included in each layer and the structure of each layer to be formed. -8 To about 10 -3 The vacuum level within the range of Torr is approximately 0.01 angstroms per second. to approximately Vacuum deposition was performed at a deposition rate in the range of / second.

[0497] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are each formed by spin coating, the spin coating can be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, depending on the materials to be included in each layer and the structure of each layer to be formed.

[0498] At least some general definitions of substituents

[0499] As used in this article, the term "C1-C" 60"Alkyl" refers to a monovalent group of a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms. Examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is similar to that used in this context. 60 "alkylene" refers to a compound that is substantially C1-C2. 60 Divalent groups with the same structure as alkyl groups.

[0500] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group at C2-C 60 An alkyl group has at least one carbon-carbon double bond in its main chain (e.g., middle) or terminal (e.g., end). Examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that is essentially C2-C 60 Divalent groups with the same structure as alkenyl groups.

[0501] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 An alkyl group has at least one carbon-carbon triple bond in its main chain or at its terminal. Examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group that is essentially C2-C 60 Divalent groups with the same structure as alkynyl groups.

[0502] As used in this article, the term "C1-C" 60 "Alkyloxy" refers to the compound formed by -OA 101 The monovalent group represented (where A) 101 For C1-C 60 Alkyl groups). Examples include methoxy, ethoxy, and isopropoxy groups.

[0503] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic cycloalkanes comprising 3 to 10 carbon atoms in a saturated hydrocarbon. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound having essentially the same structure as C3-C4. 10 Divalent groups with the same structure as cycloalkyl groups.

[0504] As used in this article, the term "C1-C" 10 Heterocyclic alkyl groups refer to monovalent monocyclic groups comprising at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom and 1 to 10 carbon atoms. Examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound having essentially the same structure as C1-C1.10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0505] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a non-aromatic monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring. Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Iridylene" refers to a group that is essentially C3-C6 10 A divalent group with the same structure as a cycloalkenyl group.

[0506] As used in this article, the term "C1-C" 10 Heterocyclic alkenyl groups refer to monovalent monocyclic groups comprising at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, 1 to 10 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 is substantially similar to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0507] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system containing 6 to 60 carbon atoms, as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic system containing 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups include fluorenyl, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and 1,2-benzophenanthryl. When C6-C... 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings independently, the rings can fused together (e.g., combined together).

[0508] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system, which has at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 60 carbon atoms. As used herein, the term "C1-C" is also relevant. 60 "Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system, where the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 60 carbon atoms. C1-C 60Examples 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 independently comprises two or more rings, the rings can fused together (e.g., combine together).

[0509] As used in this article, the term "C6-C" 60 "Aryloxy" is composed of -OA 102 (where A) 102 For C6-C 60 Aryl) is indicated. As used herein, the term "C6-C" is... 60 "Arylthio" is derived from -SA 103 (where A) 103 For C6-C 60 (Aromatic) indicates.

[0510] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more fused (e.g., combined together) rings and having only carbon atoms as cyclic atoms (e.g., 8 to 60 carbon atoms), wherein the entire molecular structure is nonaromatic. Examples of monovalent nonaromatic fused polycyclic groups may include fluorene groups. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.

[0511] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings and having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), wherein the entire molecular structure is nonaromatic. Examples of monovalent nonaromatic fused heterocyclic groups may include carbazole groups. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused heterocyclic group.

[0512] As used in this article, the term "C5-C" 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having only 5 to 60 carbon atoms as cyclic atoms, preferably C5-C6. 30 Carbocyclic group. C5-C 60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group, as used herein. 60 The term "carbocyclic group" refers to a ring (e.g., benzene), a monovalent group (e.g., phenyl), or a divalent group (e.g., phenylene). Furthermore, it depends on the group attached to C5-C. 60 The number of substituents in the carbocyclic group, C5-C 60The carbon ring group can be a trivalent group or a tetravalent group.

[0513] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to a group that is substantially C5-C6 60 Groups with the same structure as carbocyclic groups, but differing in that, in addition to carbon atoms (e.g., 1 to 60 carbon atoms), at least one heteroatom selected from N, O, Si, P, and S is used as the cyclic atom, preferably C2-C. 30 Heterocyclic groups.

[0514] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hypoaryl, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be selected from:

[0515] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;

[0516] Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, 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 fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 );

[0517] 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;

[0518] Each is replaced by at least one of the following C3-Cs. 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60Alkyl, 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 fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 );as well as

[0519] -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 ),

[0520] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heterocyclic group; C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group; C6-C substituted with at least one group selected from deuterium, -F and cyano. 60 Aryl; biphenyl; and terphenyl.

[0521] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to ethyl. t " " indicates tert-butyl, and as used herein, the term "OMe" indicates methoxy.

[0522] As used herein, the term "biphenyl" refers to a phenyl group that has been substituted with at least one phenyl group. For example, "biphenyl" belongs to the group with a C6-C... 60 "Aryl" refers to "substituted phenyl" as a substituent.

[0523] As used herein, the term "terphenyl" refers to a phenyl group substituted with at least one biphenyl group. "Terphenyl" belongs to the group that has a C6-C substituted structure. 60 Aryl-substituted C6-C 60 "Aryl" refers to "substituted phenyl" as a substituent.

[0524] Unless otherwise defined, the symbols * and *' as used herein refer to the binding sites with adjacent atoms in the corresponding formula.

[0525] The compounds and organic light-emitting devices according to one or more embodiments will be described in more detail below with reference to synthesis examples and embodiments. The phrase "using B instead of A" used in the description of synthesis examples means that the amount of B used is the same as the amount of A used in terms of molar equivalents.

[0526] Example

[0527] Synthesis Example 1: Synthesis of Compound 1

[0528]

[0529] Synthetic intermediate 1-1

[0530] 10 g of 4-triphenylmethylaniline was dissolved in 150 mL of dimethylformamide (DMF) solvent, and 5.3 g of N-bromosuccinimide (NBS) was slowly added to it at 0 °C. The reaction was then carried out at room temperature, followed by purification to obtain 11.7 g of intermediate 1-1 (yield: 95%).

[0531] Synthetic intermediates 1-2

[0532] 11.7 g of intermediate 1-1 was dissolved in 200 mL of ethanol, and excess HCl (3 eq. or more) was slowly added to it at room temperature with stirring. After stirring, 3.9 g of sodium nitrite (NaNO2) was added, and the reaction was carried out at 80 °C. The mixture was then purified to obtain 7.89 g of intermediate 1-2 (yield: 70%).

[0533] Synthetic compound 1

[0534] 2 g of 3,9'-bicarbazole, 2.4 g of intermediates 1-2, 0.87 g of sodium tert-butoxide, 0.22 g of tris(dibenzylacetone)dipalladium(0), and 0.13 mL of tritert-butylphosphine (P(t-Bu)3) were dissolved in 30 mL of toluene and stirred for 12 hours. After stirring, the organic layer obtained from the extraction reaction solution was dried. Subsequently, it was separated and purified by column chromatography, followed by sublimation purification, to obtain 3.45 g of compound 1 (yield: 88%).

[0535] Synthesis Example 2: Synthesis of Compound 5

[0536]

[0537] Synthetic intermediate 5-1

[0538] 5 g of carbazole, 11.94 g of intermediate 1-2, 4.3 g of sodium tert-butoxide, 1.09 g of tris(dibenzylacetone)dipalladium(0), and 0.5 mL of tri-tert-butylphosphine were dissolved in 150 mL of toluene solvent, and then stirred for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction of the reaction solution was dried. Subsequently, the residue was separated and purified by column chromatography to obtain 10.89 g of intermediate 5-1 (yield: 75%).

[0539] Synthetic intermediate 5-2

[0540] 10.89 g of intermediate 5-1 was dissolved in 120 mL of DMF solvent, and 3.99 g of NBS was slowly added to it at 0 °C. The reaction was then carried out at room temperature, followed by purification to obtain 12.02 g of intermediate 5-2 (yield: 95%).

[0541] Synthetic compound 5

[0542] 2 g of 3,9'-bicarbazole, 3.4 g of intermediate 5-2, 0.87 g of sodium tert-butoxide, 0.22 g of tris(dibenzylacetone)dipalladium(0), and 0.13 mL of tritert-butylphosphine were dissolved in 30 mL of toluene and stirred for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction of the reaction solution was dried. Subsequently, the mixture was separated and purified by column chromatography, followed by sublimation purification, to give 4.07 g of compound 5 (yield: 83%).

[0543] Synthesis Example 3: Synthesis of Compound 9

[0544]

[0545] Synthetic intermediate 9-1

[0546] 7.89 g of intermediate 1-2, 3.8 g of potassium acetate, and 0.69 g of bis(triphenylphosphine)palladium(II) dichloride were added to 100 mL of toluene solvent and stirred. The mixture was then reacted with 10 g of bis(pinacol)diboron at 10 °C to give 5.28 g of intermediate 9-1 (yield: 60%).

[0547] Synthetic compound 9

[0548] 2 g of 9-(3-bromophenyl)-3,9'-bi-9H-carbazole, 1.83 g of intermediate 9-1, and 0.24 g of tetra(triphenylphosphine)palladium(0) were added to 5 mL of 2 mol (M) aqueous potassium carbonate solution and 20 mL of tetrahydrofuran (THF), and then stirred at 90 °C for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction reaction solution was dried. Subsequently, separation and purification were performed by column chromatography, followed by sublimation purification, to obtain 2.77 g of compound 9 (yield: 93%).

[0549] Synthesis Example 4: Synthesis of Compound 13

[0550]

[0551] Synthetic compound 13

[0552] 2 g of 9-(2-bromophenyl)-3,9'-bi-9H-carbazole, 1.83 g of intermediate 9-1, and 0.24 g of tetra(triphenylphosphine)palladium(0) were added to 5 mL of 2M potassium carbonate aqueous solution and 20 mL of THF, and then stirred at 90 °C for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction reaction solution was dried. Subsequently, separation and purification were performed by column chromatography, followed by sublimation purification, to obtain 2.83 g of compound 13 (yield: 95%).

[0553] Synthesis Example 5: Synthesis of Compound 17

[0554]

[0555] Synthetic compound 17

[0556] 2 g of 3,9'-bicarbazole, 3.4 g of 1-bromo-4-triphenylmethylbenzene, 0.87 g of sodium tert-butoxide, 0.22 g of tris(dibenzylacetone)dipalladium(0), and 0.13 mL of tritert-butylphosphine (P(t-Bu)3) were dissolved in 30 mL of toluene and stirred for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction of the reaction solution was dried. Subsequently, separation and purification were performed by column chromatography, followed by sublimation purification, to obtain 3.8 g of compound 17 (yield: 97%).

[0557] Synthesis Example 6: Synthesis of Compound 21

[0558]

[0559] Synthetic intermediate 21-1

[0560] 10 g of 9-(4-triphenylmethylphenyl)-9H-carbazole was dissolved in 120 mL of DMF solvent, and 3.52 g of NBS was slowly added to it at 0 °C. The reaction was then carried out at room temperature, followed by purification to obtain 11.39 g of intermediate 21-1 (yield: 98%).

[0561] Synthetic compound 21

[0562] 2 g of 3,9'-bicarbazole, 3.4 g of intermediate 21-1, 0.87 g of sodium tert-butoxide, 0.22 g of tris(dibenzylacetone)dipalladium(0), and 0.13 mL of tritert-butylphosphine were dissolved in 30 mL of toluene and stirred for 12 hours. Once the reaction was considered complete, the organic layer obtained from the extraction of the reaction solution was dried. Subsequently, separation and purification were performed by column chromatography, followed by sublimation purification, to obtain 3.8 g of compound 21 (yield: 97%).

[0563] The synthesized compounds 1The 1H NMR and MS / FAB results are shown in Table 1. The methods for synthesizing compounds other than those shown in Table 1 should be readily understood by those skilled in the art by referring to the above-described synthetic mechanisms and starting materials.

[0564] Table 1

[0565]

[0566]

[0567] Example 1

[0568] Corning 15 ohms per square centimeter (Ω / cm) 2 ) The ITO glass substrate is cut to a size of 50mm × 50mm × 0.7mm, ultrasonicated in isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone, thus using the glass substrate as the anode. The glass substrate is then mounted into a vacuum deposition apparatus.

[0569] N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (NPD) was vacuum deposited onto an ITO anode formed on a glass substrate to form a thickness of [missing information]. A hole injection layer was then formed. TCTA was then vacuum-deposited onto the hole injection layer to create a thickness of [thickness value missing]. The hole transport layer.

[0570] The compound CzSi was vacuum deposited on the hole transport layer to form a thickness of [missing information]. The launch auxiliary layer.

[0571] Compound 1 (the host) and Ir(pmp)3 (the dopant) were co-deposited on the emission-assisted layer at a weight ratio of 92:8 to form a thickness of [missing information]. The emission layer.

[0572] TSPO1 was deposited on the emitter layer to form a thickness of [thickness value missing]. A buffer layer is formed, and TPBi is deposited on the buffer layer to form a thickness of [thickness value missing]. The electron transport layer.

[0573] LiF was deposited on the electron transport layer to form a thickness of [missing information]. An electron injection layer was formed, and Al was vacuum deposited on the electron injection layer to form a thickness of [missing information]. The electrodes are used to complete the fabrication of the organic light-emitting device.

[0574]

[0575] Examples 2 to 6 and Comparative Examples 1 to 8

[0576] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of compound 1.

[0577] Evaluation Example 1

[0578] To evaluate the characteristics of the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 to 8, measurements were taken at 10 mA / cm². 2 The driving voltage, luminous efficiency, and maximum external quantum efficiency (EQE) of the organic light-emitting device (OLED) at a given current density were evaluated. The driving voltage of the OLED was measured using a source meter (Keithley Instrument, 2400 series). The maximum external quantum yield of the OLED was measured using a Hamamamastu Absolute PL quantum yield measurement system C9920-2-12. In the evaluation of the maximum external quantum yield, luminance / current density was measured using a luminance meter calibrated with wavelength sensitivity, and the maximum external quantum yield was calculated based on the assumption of an angular luminance distribution (Lambertian) assuming a fully diffuse reflective surface. The evaluation results of the OLED are shown in Table 2.

[0579] Table 2

[0580]

[0581]

[0582]

[0583] Referring to the results in Table 1, it was found that the organic light-emitting devices of Examples 1 to 6 had superior driving voltage, luminous efficiency, and maximum external quantum efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 8.

[0584] It is evident from the preceding description that organic light-emitting devices, including heterocyclic compounds represented by Formula 1, can have excellent driving voltage, luminous efficiency, and maximum external quantum efficiency.

[0585] It should be understood that the embodiments described herein should be considered descriptive only and not for limiting purposes. Descriptions of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of this disclosure as defined by the appended claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; An organic layer between the first electrode and the second electrode, including an emission layer; as well as At least one heterocyclic compound represented by Formula 1: Formula 1 In Equation 1, X is a group of carbon elements other than silicon or germanium. Rings Ar1 to Ar4 are each independently C5-C 30 Carbocyclic group, L1 is selected from: single key; and Each was not replaced or was replaced by at least one Z 10a Substituted phenyl, naphthyl, anthraceneyl, pyrene, fluorenyl, dibenzofuranyl, and dibenzothiopheneyl, a1 is an integer selected from 1 to 10. Y1 and Y2 are each independently either single bonds or non-bonds. n is an integer selected from 1 to 5. R1, R2, and R4 through R7 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), R3 is 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 group, 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 group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), Z1 and Z 10a 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; Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl and naphthyl; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, -Si(Q) 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 ) and -B(Q 41 (Q) 42 );as well as -Si(Q 51 )(Q 52 )(Q 53 )、-N(Q 51 )(Q 52 ) and -B(Q 51 )(Q 52 ), Q 41 To Q 43 and Q 51 To Q 53 Each is selected independently from: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, and tert-pentyl: deuterium and C1-C 10 alkyl, d1 and d2 are each independent integers selected from 1 to 4. d3 is an integer selected from 1 to 3. d4 to d7 are each an independent integer selected from 1 to 20. d11 is an integer selected from 1 to 4. The substituted C1-C 60 Alkyl groups, the substituted C2-C 60 alkenyl, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 Alkoxy groups, the substituted C3-C 10 cycloalkyl, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 Aryl, the substituted C6-C 60 aryloxy groups, the substituted C6-C 60 Arylthioyl, the substituted C1-C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group are selected from: 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; Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, 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 fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 ); Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 ); as well as -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 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 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heterocyclic group; C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group; C6-C substituted with at least one group selected from deuterium, -F and cyano. 60 Aryl; biphenyl; and terphenyl.

2. The organic light-emitting device as claimed in claim 1, wherein: The first electrode is the anode. The second electrode is a cathode, and The at least one heterocyclic compound represented by Formula 1 is included in the organic layer, and the organic layer further includes 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.

3. The organic light-emitting device of claim 2, wherein the hole transport region comprises 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 comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof.

4. The organic light-emitting device of claim 1, wherein the emitting layer comprises at least one heterocyclic compound represented by Formula 1.

5. The organic light-emitting device as claimed in claim 1, wherein: The emitter layer comprises a substrate and a dopant. The host is different from the dopant. The amount of the main component is greater than the amount of the dopant, and The main body includes at least one heterocyclic compound represented by Formula 1.

6. The organic light-emitting device of claim 4, wherein the emitting layer emits blue light or blue-green light.

7. The organic light-emitting device of claim 5, wherein the dopant emits blue light or blue-green light having a maximum emission wavelength in the range of 400 nm to 500 nm.

8. The organic light-emitting device of claim 5, wherein the dopant comprises a transition metal and excludes transition metal-nitrogen bonds and transition metal-oxygen bonds.

9. The organic light-emitting device of claim 5, wherein the dopant comprises a transition metal and a coordination bond between the transition metal and a carbon atom.

10. The organic light-emitting device of claim 1, wherein the at least one heterocyclic compound represented by formula 1 is used as a material for a capping layer on the outside of a pair of electrodes of the organic light-emitting device.

11. A heterocyclic compound represented by Formula 1: Formula 1 in, In Equation 1, X is a group of carbon elements other than silicon or germanium. Rings Ar1 to Ar4 are each independently C5-C 30 Carbocyclic group, L1 is selected from: single key; and Each was not replaced or was replaced by at least one Z 10a Substituted phenyl, naphthyl, anthraceneyl, pyrene, fluorenyl, dibenzofuranyl, and dibenzothiopheneyl, a1 is an integer selected from 1 to 10. Y1 and Y2 are each independently either single bonds or non-bonds. n is an integer selected from 1 to 5. R1, R2, and R4 through R7 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), R3 is 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 group, 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 group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), Z1 and Z 10a 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; Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl and naphthyl; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, -Si(Q) 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 ) and -B(Q 41 (Q) 42 );as well as -Si(Q 51 )(Q 52 )(Q 53 )、-N(Q 51 )(Q 52 ) and -B(Q 51 )(Q 52 ), Q 41 To Q 43 and Q 51 To Q 53 Each is selected independently from: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, and tert-pentyl: deuterium and C1-C 10 alkyl, d1 and d2 are each independent integers selected from 1 to 4. d3 is an integer selected from 1 to 3. d4 to d7 are each an independent integer selected from 1 to 20. d11 is an integer selected from 1 to 4. The substituted C1-C 60 Alkyl groups, the substituted C2-C 60 alkenyl, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 Alkoxy groups, the substituted C3-C 10 cycloalkyl, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 Aryl, the substituted C6-C 60 aryloxy groups, the substituted C6-C 60 Arylthioyl, the substituted C1-C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group are selected from: 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; Each is selected from at least one of the following C1-C substituted. 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, 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 fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 ); Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 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 groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 ); as well as -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 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 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl; C6-C 60 Aryl; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; monovalent non-aromatic fused heterocyclic group; C1-C substituted with at least one of deuterium, -F and cyano. 60 Alkyl group; C6-C substituted with at least one group selected from deuterium, -F and cyano. 60 Aryl; biphenyl; and terphenyl.

12. The heterocyclic compound of claim 11, wherein X is carbon or tin.

13. The heterocyclic compound of claim 11, wherein rings Ar1 to Ar4 are each independently phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, or 1,2,3,4-tetrahydronaphthyl.

14. The heterocyclic compound of claim 11, wherein L1 is: a single bond; or a group represented by one of formulas 4-1 to 4-9: in, In equations 4-1 to 4-9, Z 21 and Z 22 Each and Z in claim 11 10a The descriptions are the same. d31 is an integer selected from 1 to 4. d32 is an integer selected from 1 to 6, and * and *' each indicate the binding site with the adjacent atom.

15. The heterocyclic compound of claim 11, wherein: Y1 is a single bond, and Y2 is a single bond; Y1 is a non-bonded bond, and Y2 is a single bond; Y1 is a single bond, and Y2 is a non-bond; or Y1 is a non-bonded bond, and Y2 is a non-bonded bond.

16. The heterocyclic compound of claim 11, wherein R1, R2, and R4 through R7 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy; Each is selected from at least one of the following C1-C substituted. 20 Alkyl and C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrylolyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzoxazole alkyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl and azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, indole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, Quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthroline, benzimidazolyl, benzofuranyl, benzothiophene, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ); -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2); and Groups represented by formula 2-1: in, In Equation 2-1, Z 11 and Z 12 Each is identical to the one described with respect to Z1 in claim 11. d21 and d22 are each independent integers selected from 1 to 4. *Indicates the binding site with adjacent atoms, and Among them, Q1 to Q3 and Q 31 To Q 33 Each is selected independently from: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2; and Each of the following is either unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, and triazinyl: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl.

17. The heterocyclic compound of claim 11, wherein the heterocyclic compound is represented by formula 1-1: Equation 1-1 in, In Equation 1-1, X, rings Ar1 to Ar4, L1, a1, Y1, Y2, n, R1 to R7, Z1, d1 to d7, and d11 are the same as those described in claim 11.

18. The heterocyclic compound of claim 11, wherein the product of formula 1 is composed of... The part represented is one of equations 3-1 to 3-3: in, In equations 3-1 to 3-3, d7 is an integer selected from 1 to 4. X, rings Ar1 to Ar3, L1, a1, R4 to R7, and d4 to d7 are identical to those described in claim 11, and * Indicates the binding site with adjacent atoms.

19. The heterocyclic compound of claim 11, wherein the product of formula 1 is composed of... The part represented is one of equations 5-1 to 5-36: in, In Equations 5-1 to 5-36, Y2 is the same as that described for Y2 in claim 11, and R 11 To R 14 Each is identical to that described with respect to R1 in claim 11, and R 21 To R 24 Each is identical to the description of R2 in claim 11, provided that R 11 To R 14 and R 21 To R 24 Each is not hydrogen.

20. The heterocyclic compound of claim 11, wherein the heterocyclic compound is any one of compounds 1, 2, 4 to 6, 8 to 10, 12 to 14, 16 to 18, 20 to 22, 24, 25, 27, 28, 30, 31, 33 to 36, 40 to 44, 47 to 50, 52 to 54, 56 to 58, 60 to 62, 65, 66, 69, 70, and 73 to 80. 。

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