Anthracene compound and organic light emitting device comprising the same

Abstract

The present application relates to an anthracene compound represented by formula 1 and an organic light emitting device including the anthracene compound represented by formula 1, wherein, in formula 1, X can be selected from the group consisting of a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted benzo[9,10]phenanthrylene group, and a substituted or unsubstituted phenanthrolinylene group: formula 1.

Description

[0001] This application is a divisional application of the invention patent application filed on July 23, 2020, with application number 202010727954.8 and invention title "Anthracene Compounds and Organic Light-Emitting Devices Including the Anthracene Compounds".

[0002] Cross-references to related applications

[0003] This application claims priority and benefit to Korean Patent Application No. 10-2019-0091154, filed on July 26, 2019, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0004] One or more aspects of embodiments of this disclosure relate to anthracene compounds and organic light-emitting devices comprising the anthracene compounds. Background Technology

[0005] Organic light-emitting devices are self-emitting devices that produce full-color images and, compared with devices in related fields, also have wide viewing angles, high contrast, short response times, and superior characteristics in terms of brightness, driving voltage, and / or response speed.

[0006] An organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied by the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied by the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) can recombine in the emitter layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby generating light. Summary of the Invention

[0007] One or more aspects of embodiments of this disclosure relate to anthracene compounds capable of improving luminescence efficiency, and organic light-emitting devices including the anthracene compounds.

[0008] Other aspects will be set forth in part in the description which follows, and in part will be apparent from the description or may be learned by practice of the embodiments presented.

[0009] One or more exemplary embodiments of this disclosure provide anthracene compounds represented by Formula 1:

[0010] Formula 1

[0011] .

[0012] In Equation 1,

[0013] X can be selected from substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted trehalyl, substituted or unsubstituted benzo[9,10]phenanthrene, and substituted or unsubstituted phenanthrene-rholine.

[0014] m1 can be an integer selected from 1 to 3.

[0015] L 11 and L 12 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0016] a11 and a12 can each be independently selected from 0, 1, 2, and 3, where, when a11 is 0, it is determined by *-(L 11 ) a11 -*' indicates that the key can be a single key, and when a12 is 0, it is represented by *-(L 12 ) a12 The '-*' symbol indicates that the key can be a single key.

[0017] R 11 To R 14 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -N(Q1)(Q2), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0018] b11 and b12 can each be an integer selected from 1 to 5 independently.

[0019] b13 and b14 can each be an integer selected from 1 to 8 independently.

[0020] m2 can be an integer selected from 1 to 10.

[0021] Substituted phenanthrene, substituted pyrene, substituted benzo[9,10]phenanthrene, substituted phenanthrene-roline, 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:

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

[0023] 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 );

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

[0025] Each is substituted by at least one of the following 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 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

[0026] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),and

[0027] 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, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.

[0028] One or more exemplary embodiments of this disclosure provide an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, and the organic light-emitting device comprising at least one anthracene compound represented by Formula 1. Attached Figure Description

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

[0030] Figures 1 to 4 This is a schematic diagram of the structure of an organic light-emitting device according to an embodiment of the present disclosure. Detailed Implementation

[0031] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout, and redundant descriptions may be omitted. In this regard, embodiments may take different forms and should not be construed as limited to the descriptions set forth herein. Therefore, embodiments are described below with reference to the figures only for the purpose of explaining aspects of this description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. For example, the expression “at least one” modifies the entire column of elements when preceding a column of elements, without modifying any individual element in that column.

[0032] As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. It will be further understood that the terms “includes,” “including,” “comprises,” and / or “comprising,” when used in this specification, specify the presence of the described features, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more other features, steps, operations, elements, components, and / or groups thereof. Furthermore, when describing embodiments of this disclosure, the word “may” refers to “one or more embodiments of this disclosure.”

[0033] It will be understood that when an element is referred to as being “on”, “connected to”, or “coupled to” another element, it may be directly on, directly connected to, or directly coupled to the other element, or one or more intermediate elements may exist. When an element is referred to as being “directly on”, “directly connected to”, or “directly coupled to” another element, no intermediate elements exist.

[0034] The anthracene compounds according to the embodiments can be represented by Formula 1:

[0035] Formula 1

[0036] .

[0037] In Formula 1, X can be selected from substituted or unsubstituted phenanthroline, substituted or unsubstituted pyrene, substituted or unsubstituted pyrene, substituted or unsubstituted benzo[9,10]phenanthroline, and substituted or unsubstituted phenanthroline.

[0038] In the anthracene compounds according to embodiments, when X is selected from divalent groups, the singlet state conversion rate caused by the triplet-triplet fusion (TTF) phenomenon can be improved compared to organic light-emitting materials in the related art. For example, when X in Formula 1 is a substituted or unsubstituted pyrene group, the TTF phenomenon can occur in the anthracene unit and / or pyrene unit in the anthracene compound represented by Formula 1. Therefore, in the anthracene compounds according to embodiments, the spacer unit X is a compound (e.g., partially) having TTF properties (e.g., capable of TTF), and the singlet state conversion rate can be improved (e.g., as caused by the TTF mechanism).

[0039] Unrestricted by the correctness of any theory or its interpretation, density functional theory (DFT) calculations for anthracene compounds in which X in Formula 1 is pyrene-based have confirmed that two degenerate triplet levels, namely, the first triplet (T1) and the second triplet (T2), can induce TTF in different units of the molecule, such as in the anthracene unit or the pyrene (X linker) unit of the compound. Furthermore, the anthracene compound according to the embodiments can be converted from the triplet state (formed after TTF) to the singlet state via a total of four spin-flip transitions. When X is one of the aforementioned groups, this electronic structure and capability can be extrapolated to the embodiments of the anthracene compound represented by Formula 1. When X is not selected from the above groups, for example, when X is spiro-fluorene-based, no TTF occurs within the spiro-fluorene spacer unit. Therefore, compared to organic light-emitting materials in the related art, the ratio of triplet to singlet conversion can be increased in the anthracene compounds according to the embodiments.

[0040] In one embodiment, X in Formula 1 may be a group represented by free formulas 3-1 to 3-12:

[0041]

[0042] .

[0043] In equations 3-1 to 3-12,

[0044] R 31 To R 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, pyrene, trefyl, fluoranyl, benzo[9,10]phenanthrene, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthrene, acridineyl, phenanthroline, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),

[0045] b32 can be 1 or 2.

[0046] b33 can be 1, 2, or 3.

[0047] b34 can be 1, 2, 3, or 4.

[0048] b35 can be 1, 2, 3, 4, or 5.

[0049] Q 31 To Q 33 Each can be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl, and

[0050] * and *' each indicate the binding site with the adjacent atom.

[0051] In one or more embodiments, X in Formula 1 may be a group represented by free formulas 4-1 to 4-5:

[0052] .

[0053] In equations 4-1 to 4-5,

[0054] * and *' each indicate the binding site with the adjacent atom.

[0055] In Equation 1, m1 can be an integer selected from 1 to 3. m1 in Equation 1 indicates the number of repeating units of the interval unit represented by X. When m1 is 2 or 3, the two or three Xs can be the same or different from each other.

[0056] In one implementation, m1 in Equation 1 can be 1.

[0057] In Equation 1, L 11 and L 12 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0058] In one implementation, L 11 and L 12 Each can be selected independently:

[0059] Cyclobutylene, cyclopentylene, cyclohexylene, phenylene, pentyleneene, indene, naphthylene, azulene, heptylene, acenaphthene, fluorene, spiro-difluorene, benzo[2]fluorene, dibenzo[2]fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, trehalene, tetraphenylene, stylene, perylene, Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphridyl, quinoxalinyl, quinoxalinyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, and dibenzothiophene; and

[0060] Each of the following is substituted with at least one of the following: cyclobutylene, cyclopentylene, cyclohexylene, phenylene, pentyleneylene, indene, naphthylene, azoxyene, heptylene, acenaphthene, fluorene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenylene, anthracene, fluorenylene, benzo[9,10]phenenylene, pyrene, trehalyl, tetraphenylene, stylene, perylene, pyridylene, pyrazinylene, pyrazinylene, cyclo[9,10]phenenylene, pyrene, trehalylene, cyclo[9,10]phenylene, pyrene, perylene, pyridylene, pyrazinylene, cyclo[9,10]phenenylene, pyrene ... Iridinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, naphthinyl, quinoxalinyl, quinoxalinyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl and dibenzothiophene: 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, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, trefoil, tetraphenyl alkyl, puryl, peryl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, naphridyl, quinoxalinyl, quinazolinyl, thiophene, furanyl, carbazoleyl, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ).

[0061] In Equation 1, a11 and a12 can each be independently 0, 1, 2, or 3. When a11 is 0, it is determined by *-(L 11 ) a11 -*' indicates that the key can be a single key, and when a12 is 0, it is represented by *-(L 12 ) a12 The key represented by -*' can be a single key.

[0062] In one implementation, each of a11 and a12 in Equation 1 can be 0.

[0063] In Equation 1, R 11 To R 14Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -N(Q1)(Q2), -S(=O)2(Q1) and -P(=O)(Q1)(Q2).

[0064] In one implementation, R 11 To R 14 Each can be selected independently:

[0065] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0066] 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, cyano, phenyl, and biphenyl;

[0067] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptanenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranthryl, benzo[9,10]phenanthreneyl, pyrene, trefyl, tetraphenyl, styrene, peryl, pentyleneyl, hexaphenyl, Pentaphenyl, Rubinyl, Myristyl, Oleophane, Pyrrolyl, Thiopheneyl, Furanyl, Thirrolyl, Imidazolyl, Pyrazolyl, Thiazolyl, Isothiazolyl, Oxazolyl, Isoxazolyl, Pyridyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Indolyl, Isoyndolyl, Indolyl, Puryl, Quinolinyl, Isoquinolinyl, Benzoquinolinyl, Phtharazinyl, Naphthidyl, Quinoxalinyl, Quinazolinyl, Tripolinyl, Phenyridinyl, Acridineyl, Phenyrrolinyl Phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiopyrrolyl, benzisisothiazolyl, benzooxazolyl, benzisisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl Azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopheneyl, 8H-indolo[3,2,1-de]acridyl, 7,11-dihydrobenzo[1,8]inzazino[2,3,4,5,6-defg]acridyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) and -B(Q1)(Q2); and

[0068] Each of the following substituted compounds is selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptanenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, tretyl, tetraphenyl, styrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridineyl Acridine, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazole, benzocarbazole, dibenzocarbazole, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzyl Naphthidyl, azirmonyl, azispiro-difluorenyl, azircarbazolyl, azirdibenzofuranyl, azirdibenzothiophene, azirdibenzothiophene, 8H-indolo[3,2,1-de]acridyl and 7,11-dihydrobenzo[1,8]inzazino[2,3,4,5,6-defg]acridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[2]fluorenyl, dibenzo[2]fluorenyl, phenanthrenyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthreneyl, pyrene, trefoil, tetraphenyl, styrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, pyrrolyl, thiophenyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl alkyl, phenanthrynyl, phenanthrynyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, Imidazolopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoyl, azadibenzofuranyl, azadibenzothiopheneyl, azadibenzothiopheneyl, 8H-indolo[3,2,1-de]acridinyl, 7,11-dihydrobenzo[1,8]inzazino[2,3,4,5,6-defg]acridinyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ).

[0069] In one or more embodiments, in Equation 1, R 11 and R 12 Each can be selected independently:

[0070] Phenyl, biphenyl, terphenyl, pentanenyl, indyl, naphthyl, azuleyl, heptenyl, indarabenyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthryl, pyrene, trefyl, tetraphenyl, styrene, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rubiginyl, keratyl, ovoleyl, pyrroleyl, thiopheneyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridinyl, isoindoleyl, indoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, carbazoleyl, Benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, 8H-indolo[3,2,1-de]acridyl and 7,11-dihydrobenzo[1,8]inzazin[2,3,4,5,6-defg]acridyl; and

[0071] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, trefyl, tetraphenyl, styryl, perylene, pentanyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, ovoleyl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, carbazole, benzoquinolinyl, phthalazinyl Naphthidyl, quinoxalinyl, quinazolinyl, phenanthridine, acridine, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, 8H-indolo[3,2,1-de]acridyl and 7,11-dihydrobenzo[1,8]inzazin[2,3,4,5,6-defg]acridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, pentanenyl, indene, naphthyl, azuleyl, heptenyl, indane, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthrene, pyrene, trefyl, tetraphenyl, styrene, peryl, pentanyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purine, quinolinyl, isoquinolinyl, carbazoleyl Benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, 8H-indolo[3,2,1-de]acridyl, 7,11-dihydrobenzo[1,8]inzazin[2,3,4,5,6-defg]acridyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ).

[0072] In one or more embodiments, R in Equation 1 11 and R 12 Each can be independently selected from groups represented by free formulas 5-1 to 5-87:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080] .

[0081] In equations 5-1 to 5-87,

[0082] Y 31 Selectable from O, S, N (Z) 33 ), C(Z) 33 (Z) 34 ) and Si(Z 33 (Z) 34 ),

[0083] Z 31 To Z 37 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, pyrene, trefyl, fluoranyl, benzo[9,10]phenanthrene, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthrene, acridineyl, phenanthroline, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),

[0084] e2 can be 1 or 2.

[0085] e3 can be an integer selected from 1 to 3.

[0086] e4 can be an integer selected from 1 to 4.

[0087] e5 can be an integer selected from 1 to 5.

[0088] e6 can be an integer selected from 1 to 6.

[0089] e7 can be an integer selected from 1 to 7.

[0090] e9 can be an integer selected from 1 to 9.

[0091] Q 31 To Q 33 Each can be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl, and

[0092] * Indicates the binding site with adjacent atoms.

[0093] In one or more embodiments, R in Equation 1 11 and R 12 Each group can be independently selected from those represented by free formulas 6-1 to 6-34:

[0094]

[0095]

[0096]

[0097] .

[0098] In equations 6-1 to 6-34,

[0099] Z 32 To Z 34 Z 36 and Z 37 Each can be independently selected from hydrogen, C1-C 20 Alkyl and phenyl, and

[0100] * Indicates the binding site with adjacent atoms.

[0101] In one implementation, in Equation 1, R 13 and R 14 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, and phenyl; and

[0102] The phenyl group substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, and phenyl.

[0103] In one implementation, in Equation 1, R 13 and R 14 Each of them can be hydrogen.

[0104] In Equation 1, b11 and b12 can each be an integer selected from 1 to 5 independently, and b13 and b14 can each be an integer selected from 1 to 8 independently.

[0105] In Equation 1, m2 can be an integer selected from 1 to 10.

[0106] In Equation 1, the number of anthracene units in a molecule increases with increasing m². The TTF phenomenon occurring in anthracene increases proportionally with the number of anthracene units, thereby increasing the singlet state conversion rate. Therefore, the fluorescence efficiency of anthracene compounds represented by Equation 1 can be increased.

[0107] In one implementation, m2 in Equation 1 can be an integer selected from 1 to 5. For example, m2 in Equation 1 can be 1.

[0108] In one embodiment, anthracene compounds can be represented by formula 1-1:

[0109] Equation 1-1

[0110] .

[0111] In Equation 1-1,

[0112] X, L 11 L 12 R 11 To R 14 b11 to b14 and m2 can each be independently identical to those described above.

[0113] In one or more embodiments, anthracene compounds may be represented by formulas 1-2:

[0114] Formula 1-2

[0115] .

[0116] In Equation 1-2,

[0117] X, R 11 R 12 Both m2 and m2 can be independently identical to those described by combination 1.

[0118] In one embodiment, in formula 1-2, X can be selected from groups represented by free formulas 4-1 to 4-5, and

[0119] R 11 and R 12 Each group can be independently selected from those represented by free formulas 6-1 to 6-34:

[0120] .

[0121] Among them, in equations 4-1 to 4-5,

[0122] * and *' each indicate the binding site with the adjacent atom.

[0123]

[0124]

[0125]

[0126] .

[0127] In equations 6-1 to 6-34,

[0128] Z 32 To Z 34 Z 36 and Z 37 Each can be independently selected from hydrogen, C1-C 10 Alkyl and phenyl, and

[0129] * Indicates the binding site with adjacent atoms.

[0130] In one embodiment, the anthracene compound represented by Formula 1 may be selected from compounds 1 and 2:

[0131] Compound 1 Compound 2

[0132] .

[0133] In this specification, C3-C is replaced. 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 60At 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:

[0134] 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;

[0135] 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 );

[0136] 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;

[0137] Each is substituted by at least one of the following 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: 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

[0138] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),and

[0139] Q1 to Q3, Q11 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, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.

[0140] Anthracene compounds represented by Equation 1 can satisfy 2E T1 ≥ E T2 .

[0141] E T1 E represents the lowest excited triplet energy level of anthracene compounds. T2 It represents the second low-excited triplet energy level of anthracene compounds.

[0142] E T1 and E T2 Evaluation can be performed using any appropriate method, such as DFT methods, like those available in the Gaussian procedure (Wallingford, CT), and the structure can be optimized at the level of B3LYP / 6-311G(d,p) (e.g., using B3LYP / 6-311G(d,p) as the hybrid functional and basis set).

[0143] When the anthracene compound represented by Equation 1 satisfies 2E T1 ≥ E T2 Under certain energy conditions, anthracene compounds can possess a spin statistic of 1 / 9S + 3 / 9T + 5 / 9Q after passing through a TTF. When singlet states generated by reusing triplet excitons (e.g., via TTF) are taken into account, up to 20% of those triplet states can be increased by about 15% (an additional 15%), and the luminescence efficiency of the compounds is expected to improve due to the TTF. Therefore, organic light-emitting devices incorporating anthracene compounds can emit highly efficient delayed fluorescence.

[0144] Furthermore, anthracene compounds represented by Equation 1 can increase the TTF rate constant (K). TTF (e.g., the rate at which TTFs occur) and thus increase the number of TTF events. Therefore, the singlet state conversion rate due to TTFs can be improved, thereby improving fluorescence efficiency. For example, in addition to the singlet state conversion rate of the compound itself (e.g., the basic singlet state conversion rate), fluorescence efficiency can be improved based on the increase in the number of TTFs. Therefore, anthracene compounds can have a large amount of delayed fluorescence components (e.g., can include a large amount of fractions capable of delaying fluorescence).

[0145] When the emitting layer of an organic light-emitting device comprises an anthracene compound represented by Formula 1 and a dopant, the anthracene compound can act as the host. When the energy of T1 of the dopant is higher than that of the host (e.g., the anthracene compound), triplet diffusion from the dopant to the host occurs due to the exciton energy shifting from high to low energy, thereby further increasing the K of the anthracene compound. TTF .

[0146] Furthermore, since the anthracene compounds represented by Formula 1 can participate in multi-spin-flip transition pathways, they can improve the conversion rate from triplet to singlet state, thereby increasing luminescence efficiency.

[0147] The method for synthesizing anthracene compounds represented by Formula 1 will be apparent to those skilled in the art by referring to the following examples.

[0148] Anthracene compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device. For example, anthracene compounds can be included in the emitting layer. In some embodiments, the anthracene compound included in the emitting layer can serve as the host. In one or more embodiments, the anthracene compound of Formula 1 can be used as a material for a capping layer located outside the pair of electrodes of the organic light-emitting device.

[0149] Therefore, another aspect of this disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, and the organic light-emitting device comprising at least one anthracene compound represented by Formula 1.

[0150] In one embodiment, the organic layer of the organic light-emitting device may include at least one anthracene compound represented by Formula 1.

[0151] As used herein, the expression “(organic layer) comprises at least one anthracene compound” can refer to the case where “(organic layer) comprises the same anthracene compound represented by Formula 1” or the case where “(organic layer) comprises two or more different anthracene compounds represented by Formula 1”.

[0152] For example, the organic layer may comprise only compound 1 as an anthracene compound. In this respect, compound 1 may be present only in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may comprise both compound 1 and compound 2 as anthracene compounds. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer) or may be present in different layers (e.g., compound 1 may be present in the emitting layer and compound 2 may be present in the electron transport region).

[0153] In one embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include an anthracene compound represented by Formula 1. 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, and the hole transport region may include a hole injection layer, a hole transport layer, an emitter assist layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0154] According to an embodiment, the emitting layer of the organic light-emitting device may include an anthracene compound represented by Formula 1. The anthracene compound may be a compound capable of emitting delayed fluorescence.

[0155] In one or more embodiments, the emitting layer of the organic light-emitting device may include an anthracene compound represented by Formula 1 and a dopant. Here, the anthracene compound may be the host material. The dopant included in the emitting layer may be a fluorescent dopant, and the fluorescent dopant may include an aromatic amine compound, a styrene amine compound, or any combination thereof.

[0156] In one or more embodiments, the emitting layer of the organic light-emitting device may include an anthracene compound represented by Formula 1.

[0157] In one embodiment, the hole transport region of the organic light-emitting device may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.

[0158] As used herein, the term "organic layer" can refer to a single layer and / or multiple layers disposed between the first and second electrodes of an organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials.

[0159] Figure 1 Description

[0160] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0161] The following text will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiment and the method of manufacturing the organic light-emitting device 10 are described.

[0162] First electrode 110

[0163] exist Figure 1 In this configuration, a substrate may be additionally disposed 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.

[0164] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from a material with a high work function to facilitate hole injection.

[0165] 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 combinations thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and combinations thereof, but the embodiments of this disclosure are not limited thereto.

[0166] The first electrode 110 may have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.

[0167] Organic layer 150

[0168] An organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emitter layer.

[0169] In some embodiments, 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.

[0170] Hole transport region in organic layer 150

[0171] The hole transport region may have i) a single-layer structure comprising a single layer (including a single material); ii) a single-layer structure comprising a single layer (including multiple different materials); or iii) a multi-layer structure having multiple layers (including multiple different materials).

[0172] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.

[0173] For example, the hole transport region may have a single-layer structure including a single layer (including a variety of different materials), or a multi-layer structure, which may have a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110 in the order described therein, but the structure of the hole transport region is not limited to this.

[0174] The hole transport region may include at least one selected from the following: m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by formula 201, and compounds represented by formula 202:

[0175]

[0176] ,

[0177] Formula 201

[0178] ,

[0179] Formula 202

[0180] .

[0181] In equations 201 and 202,

[0182] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0183] 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.

[0184] xa1 to xa4 can each be an integer selected from 0 to 3 independently.

[0185] xa5 can be an integer selected from 1 to 10.

[0186] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0187] In one implementation, in formula 202, R 201 and R202 It can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond, and R 203 and R 204 It can be optionally linked via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond.

[0188] In one or more embodiments, for equations 201 and 202,

[0189] L 201 To L 205 Each can be selected independently:

[0190] Phenylidene, pentylene, indene, naphthyl, azulene, heptadene, acenaphthene, fluorenene, spiro-difluorenene, benzo[9,10]fluorenene, dibenzo[9,10]fluorenene, phenanthroline, anthracene, fluoranthroline, benzo[9,10]phenanthroline, pyrene, trehalyl, tetraphenylene, stylene, perylene, phenylene Pentofenyl, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophylene, thiophenyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzothiophenyl, and pyridylene; and

[0191] Each of the following substituted compounds is selected from at least one of the following: phenylene, pentyleneylene, indene, naphthylene, azoxyne, heptadeneylene, acenaphthene, fluorene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[1]fluorene, phenenylene, anthraceneylene, fluorenylene, benzo[9,10]phenenylene, pyreneylene, trehalylene, tetraphenylene, styleneylene, perylene, pentyleneylene, hexaphenylene, Benzenepentylene, Benzenerubinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinolylene and pyridylene: 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-salicylate, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthrene, pyrene, trefyl, tetraphenyl, salicylate, perylene, pentanyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, thiophene, furanyl, carbazolyl, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and

[0192] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0193] In one or more embodiments, xa1 to xa4 may each be 0, 1 or 2 independently.

[0194] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0195] In one or more embodiments, R 201 To R 204 and Q 201 Each can be selected independently:

[0196] Phenyl, biphenyl, terphenyl, pentanenyl, indyl, naphthyl, azuleyl, heptenyl, indarabenyl, acenaphtheyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthreneyl, pyrene, tretyl, tetraphenyl, styrene, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rubiginyl, keratyl, ovoleyl, thiophene, furanyl, carbazolyl, indoleyl, isoydinyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl; and

[0197] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthrene, anthraceneyl, fluoranyl, benzo[9,10]phenanthreneyl, pyreneyl, trefyl, tetraphenyl, styrene, peryleneyl, pentanyl, hexaphenyl Pentaphenyl, rutinyl, keratyl, ovolenyl, 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 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-salicylate, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthrene, pyrene, trefyl, tetraphenyl, salicylate, perylene, pentanyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, thiophene, furanyl, carbazolyl, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and

[0198] Q 31 To Q 33 Each can be independently identical to the one described above.

[0199] In one or more embodiments, in formula 201, R 201 To R 203 At least one of them can be independently selected from:

[0200] Fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and

[0201] Each of the following substituted fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl groups is selected from at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, 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.

[0202] However, the embodiments disclosed herein are not limited thereto.

[0203] For example, in equation 202, i) R 201 and R 202 It can be connected via a single key, and / or ii) R 203 and R 204 It can be connected via a single button.

[0204] In one or more embodiments, in formula 202, R 201 To R 204 At least one of them can be selected from:

[0205] Carbazolyl; and

[0206] 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.

[0207] However, the embodiments disclosed herein are not limited thereto.

[0208] The compound represented by formula 201 can be represented by formula 201-1:

[0209] Formula 201-1

[0210] .

[0211] In one embodiment, the compound represented by formula 201 may be represented by formula 201-2, but the embodiments of this disclosure are not limited thereto:

[0212] Formula 201-2

[0213] .

[0214] In one embodiment, the compound represented by formula 201 may be represented by formula 201-2(1), but the embodiments of this disclosure are not limited thereto:

[0215] Equation 201-2(1)

[0216] .

[0217] In one embodiment, the compound represented by formula 201 may be represented by formula 201A:

[0218] Formula 201A

[0219] .

[0220] In one embodiment, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:

[0221] Formula 201A(1)

[0222] .

[0223] In one embodiment, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:

[0224] Formula 201A-1

[0225] .

[0226] In one embodiment, the compound represented by formula 202 can be represented by formula 202-1:

[0227] Formula 202-1

[0228] .

[0229] In one embodiment, the compound represented by formula 202 can be represented by formula 202-1(1):

[0230] Equation 202-1(1)

[0231] .

[0232] In one embodiment, the compound represented by formula 202 can be represented by formula 202A:

[0233] Formula 202A

[0234] .

[0235] In one embodiment, the compound represented by formula 202 can be represented by formula 202A-1:

[0236] Formula 202A-1

[0237] .

[0238] In equations 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

[0239] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 Each can be independently identical to the one described above.

[0240] L 205 The choice can be made from phenylene and fluorene groups.

[0241] X 211 Selectable from O, S, and N(R) 211 ),

[0242] X 212 Selectable from O, S, and N(R) 212 ),

[0243] R 211 and R 212 Each can independently combine with R 203 The definitions are the same, and

[0244] 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, pentabenyl, indyl, naphthyl, azuleyl, heptabenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthryl, pyrene, trefyl, tetraphenyl, styrene, peryl, pentaphenyl, hexaphenyl, pentaphenyl, rubidyl, kosyl, ovoidyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, and pyridyl.

[0245] The hole transport region may include at least one compound selected from compounds HT1 to HT48, but embodiments of this disclosure are not limited thereto:

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253] .

[0254] The thickness of the hole transport region can be approximately 100. Approximately 10,000 For example, about 100 Approximately 1000 When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately 100. To approximately 9,000 For example, about 100 To approximately 1,000 Furthermore, the thickness of the hole transport layer can be approximately 50. To approximately 2,000 For example, about 100 To approximately 1,500 When the thicknesses of the hole transport region, hole injection layer, and hole transport layer are each within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0255] 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, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can comprise the materials described above.

[0256] p-dopants

[0257] In addition to these materials, the hole transport region may further include charge-generating materials for improving conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region.

[0258] The charge-generating material can be, for example, a p-doped agent.

[0259] In one implementation, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.

[0260] p-dopers may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments disclosed herein are not limited thereto.

[0261] In one embodiment, the p-doper may include at least one selected from the following:

[0262] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);

[0263] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0264] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and

[0265] Compounds represented by formula 221:

[0266] However, the embodiments disclosed herein are not limited thereto:

[0267] HAT-CN F4-TCNQ

[0268] ,

[0269] Equation 221

[0270] .

[0271] In Equation 221,

[0272] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein R 221 To R 223 At least one of them may have at least one substituent selected from the following: 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 20Alkyl groups and -I-substituted C1-C 20 alkyl.

[0273] Emission layer in organic layer 150

[0274] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned as a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from red, green, and blue emission layers, wherein the two or more layers may be in contact with each other or may be separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from red, green, and blue luminescent materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0275] The emission layer may include at least one anthracene compound represented by Formula 1.

[0276] The emission layer may include a host and a dopant. The material used to form the emission layer may include at least one of phosphorescent dopant, fluorescent dopant, and quantum dot.

[0277] In the emitter layer, based on 100 parts by weight of the host, the amount of dopant can be from about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.

[0278] The thickness of the emission layer can be approximately 100. To approximately 1,000 For example, about 200 Approximately 600 When the thickness of the emitting layer is within this range, excellent light emission characteristics can be obtained without a significant increase in the driving voltage.

[0279] The main body in the emission layer

[0280] The main body may include anthracene compounds represented by Formula 1.

[0281] In one or more embodiments, the body may further include a compound represented by formula 301:

[0282] Formula 301

[0283] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0284] In Equation 301,

[0285] Ar 301C5-C can be substituted or unsubstituted. 60 The carbocyclic group may or may not be substituted C1-C 60 Heterocyclic groups,

[0286] xb11 can be 1, 2, or 3.

[0287] 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.

[0288] xb1 can be an integer selected from 0 to 5.

[0289] 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, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, 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 ),

[0290] xb21 can be an integer selected from 1 to 5, and

[0291] Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0292] In one implementation, Ar in formula 301 301 Optional from:

[0293] Naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, trefyl, tetraphenyl, styrene, peryl, penfenyl, indoxanthrayl, dibenzofuranyl, and dibenzothiopheneyl; and

[0294] Each of the following substituted groups is selected from at least one of the following: naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, pyrene, trefyl, tetraphenyl, styrene, peryl, penfenyl, indoxanthrayl, dibenzofuranyl, and dibenzothiopheneyl: 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 ),and

[0295] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.

[0296] When xb11 in equation 301 is 2 or greater, two or more Ar 301 It can be connected via a single button.

[0297] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or 301-2:

[0298] Formula 301-1

[0299] ,

[0300] Formula 301-2

[0301] .

[0302] In equations 301-1 and 301-2,

[0303] A 301 To A 304 Each of these can be independently selected from phenyl, naphthyl, phenanthryl, fluoranyl, benzo[9,10]phenanthryl, pyrene, tyl, pyridyl, pyrimidinyl, indyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, indolyl, carbazole, benzo[9,10]carbazole, dibenzo[9,10]carbazole, furanyl, benzo[9,10]furanyl, dibenzo[9,10]furanyl, naphthuryl, benzo[9,10]naphthuryl, dibenzo[9,10]naphthuryl, dibenzo[9,10]naphthuryl, ...

[0304] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0305] 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 ),

[0306] xb22 and xb23 can each be 0, 1, or 2 independently.

[0307] L 301 xb1, R 301 and Q 31 To Q 33 Each can be independently identical to the one described above.

[0308] L 302 To L 304 Each can be independently combined with L 301 The same definition

[0309] xb2 to xb4 can each be independently defined identically to xb1, and

[0310] R 302 To R 304 Each can independently combine with R 301 The definitions are the same.

[0311] For example, in equations 301, 301-1, and 301-2, L 301 To L 304 Each can be selected independently:

[0312] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, treylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, carbazolyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, carbazolyl, carbazolyl, carbazolyl, carbazolyl, carbazolyl, carbazolyl, pyridylene, imidazolyl, pyridylene, thiophene 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

[0313] Each of the following substituted compounds is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, treylene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophene, dibenzo[9,10]phenylene, pentaphenylene, thiophene, carbazolyl, dibenzo[9,10]phenylene, thiophene ... Oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisoxazolyl, benzisisoxazolyl, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentofenyl, 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 ),and

[0314] Q31 To Q 33 Each can be independently identical to the one described above.

[0315] In one or more embodiments, R in formulas 301, 301-1, and 301-2 301 To R 304 Each can be selected independently:

[0316] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, 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

[0317] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[9,10]phenanthryl, pyrene, tyl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentofenyl, 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 ),and

[0318] Q 31 To Q 33 Each can be independently identical to the one described above.

[0319] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55) and Mg complexes. In some embodiments, the host may be a Zn complex.

[0320] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327] .

[0328] Phosphorescent dopants included in the emission layer of organic layer 150

[0329] Phosphorescent dopants may include organometallic complexes represented by formula 401:

[0330] Formula 401

[0331] M(L 401 ) xc1 (L 402 ) xc2 .

[0332] In Equation 401,

[0333] 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).

[0334] L 401 The ligand can be represented by the free formula 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.

[0335] Formula 402

[0336] .

[0337] L 402 It can be an organic ligand, and xc2 can be an integer selected from 0 to 4, wherein when xc2 is 2 or greater, two or more L 402 They can be the same or different from each other.

[0338] In Equation 402,

[0339] X 401 To X 404 They can be nitrogen or carbon independently.

[0340] X 401 and X 403 It can be connected via a single or double key, and X 402 and X 404It can be connected via a single key or a double key.

[0341] A 401 and A 402 Each can be independently classified as C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0342] X 405 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,

[0343] X 406 It can be a single bond, O, or S.

[0344] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, 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-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,

[0345] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and

[0346] In Equation 402, * and *' each indicate the binding site with M in Equation 401.

[0347] In one implementation, A in formula 402 401 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.

[0348] 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 simultaneously (e.g., at the same time).

[0349] In one or more embodiments, R in formula 402 401 and R 402 Each can be selected independently:

[0350] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;

[0351] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl;

[0352] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;

[0353] 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, amido, 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

[0354] -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ),and

[0355] Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.

[0356] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Can be selected via X 407(It is a linking group) linked, or two or more L 401 The two A's in 402 Can be selected via X 408 (It is a linking group) linked (see, for example, compounds PD1 to PD4 and PD7). X 407 and X 408 Each can be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q)-*', or *-N(Q)-*'. 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-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 embodiments disclosed herein are not limited thereto.

[0357] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The ligands can be selected from halides (e.g., fluorides, chlorides, bromides, or iodides), diketones (e.g., acetylacetonates), carboxylic acids (e.g., pyridine carboxylate), -C (=O), isonitriles, -CN, and phosphorus-containing ligands (e.g., phosphine or phosphites), but the embodiments disclosed herein are not limited thereto.

[0358] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but embodiments of this disclosure are not limited thereto:

[0359]

[0360]

[0361] .

[0362] Fluorescent dopants in the emission layer

[0363] Fluorescent dopants may include aromatic amine compounds or styrene amine compounds.

[0364] Fluorescent dopants may include compounds represented by formula 501:

[0365] Formula 501

[0366] .

[0367] In Equation 501,

[0368] Ar 501 C5-C can be substituted or unsubstituted. 60 The carbocyclic group may or may not be substituted C1-C 60 Heterocyclic groups,

[0369] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0370] xd1 to xd3 can each be an integer selected from 0 to 3 independently;

[0371] R 501 and R 502 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and

[0372] xd4 can be an integer selected from 1 to 6.

[0373] In one implementation, Ar in Formula 501 501 Optional from:

[0374] Naphthyl, heptalenyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, trefyl, tetraphenyl, styrene, peryl, penfenyl, ind[[9,10]anthrayl, and ind[[9,10]phenanthryl; and

[0375] Each of the following substituted groups is selected from at least one of the following: naphthyl, heptalenyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, pyrene, tretinoin, tetraphenyl, styrene, perylene, penfenyl, ind[9,10]anthrayl, and ind[9,10]phenanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0376] In one or more embodiments, L in Formula 501 501 To L 503 Each can be selected independently:

[0377] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[2-fluorene]ylene, dibenzo[2-fluorene]ylene, phenanthrene, anthracene, fluoranthylene, benzo[9,10]phenanthrene, pyrene, treylene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[2-carbazolyl, dibenzo[2-carbazolyl, dibenzothiophene, and pyridylene; and

[0378] Each of the following substituted groups is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, trehalyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]carbazolyl, dibenzo[9,10]carbazolyl, dibenzothiophene, dibenzo[9,10]carbazolyl, dibenzothiophene, dibenzo[9,10]carbazolyl, dibenzothiophene, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.

[0379] In one or more embodiments, R in formula 501 501 and R 502 Each can be selected independently:

[0380] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoyindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and

[0381] Each of the following substituted groups is selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazole, dibenzocarbazole, dibenzothiophene, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 ),and

[0382] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0383] In one or more embodiments, xd4 in formula 501 may be 2, but the embodiments of this disclosure are not limited thereto.

[0384] For example, fluorescent dopants can be selected from compounds FD1 to FD22:

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393] .

[0394] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments disclosed herein are not limited thereto:

[0395]

[0396] .

[0397] Quantum dots in the emitter layer

[0398] Quantum dots may be nanoparticles comprising (for example, formed or composed of) Group II-VI compounds, Group III-V compounds, Group IV-VI compounds, Group IV elements, or Group IV compounds.

[0399] Group IV-VI compounds may be selected from: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe and any mixture thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and any mixture thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe and any mixture thereof. Group IV elements may be selected from Si, Ge and any mixture thereof. Group IV compounds may be binary compounds selected from SiC, SiGe and any mixture thereof.

[0400] Binary, ternary, or quaternary compounds can exist in particles at a uniform concentration or in the same particles with partially different concentration distributions. Furthermore, binary, ternary, or quaternary compounds can have a core-shell structure in which one quantum dot surrounds another quantum dot. The interface between the core and shell can have a concentration gradient in which the concentration of atoms present in the shell decreases towards the center.

[0401] In one or more embodiments, the quantum dot may have a core-shell structure comprising a core having the aforementioned nanoparticles and a shell surrounding the core. The shell of the quantum dot can serve as a protective layer for maintaining semiconductor properties by preventing or reducing the chemical degradation of the core, and / or can serve as a charging layer for imparting 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 in which the concentration of atoms present in the shell decreases toward the center. Non-limiting examples of the shell of the quantum dot may include metal or nonmetal oxides, semiconductor compounds, and any combination thereof.

[0402] For example, non-limiting examples of metal or non-metal oxides may include binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO) or ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4), but embodiments of this disclosure are not limited thereto.

[0403] In addition, non-limiting examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments disclosed herein are not limited thereto.

[0404] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less. When the FWHM of the emission wavelength spectrum of quantum dots is in this range, color purity or color reproducibility can be improved. In addition, light emitted through such quantum dots can be illuminated in all directions (e.g., in all directions), thereby improving the wide viewing angle.

[0405] In some embodiments, the quantum dot is any suitable quantum dot in the art, and there are no particular limitations. For example, spherical, conical, multi-armed, or cubic nanoparticles; nanotubes; nanowires; nanofibers and / or nanoplate particles can be used.

[0406] Quantum dots can adjust the color of emitted light according to their particle size. Therefore, quantum dots can emit light with any suitable color (such as blue, red, or green).

[0407] Electron transport region in organic layer 150

[0408] The electron transport region may have i) a single-layer structure comprising a single layer (including a single material), ii) a single-layer structure comprising a single layer (including multiple different materials), or iii) a multilayer structure having multiple layers (including multiple different materials).

[0409] In some embodiments, for example, the electron transport region may include the buffer layer described above. The electron transport region may further include at least one selected from the hole blocking layer, the electron control layer, the electron transport layer, and the electron injection layer, but the embodiments of this disclosure are not limited thereto.

[0410] For example, the electron transport region may have a structure of buffer layer / electron transport layer / electron injection layer, buffer layer / hole blocking layer / electron transport layer / electron injection layer, buffer layer / electron control layer / electron transport layer / electron injection layer, or buffer layer / electron transport layer / electron injection layer, wherein the constituent layers of each structure are stacked sequentially from the emitter layer. However, the implementation of the electron transport region structure is not limited to this.

[0411] The electron transport region (e.g., one or more layers in the electron transport region) (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one ring of nitrogen with depleted π electrons.

[0412] The term "a ring containing nitrogen with depleted π electrons" refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic groups.

[0413] For example, "a ring containing nitrogen with depleted π electrons" can be i) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heterocyclic groups, each having at least one *-N=*' moiety, are fused together; or iii) a 5- to 7-membered heterocyclic group, each having at least one *-N=*' moiety, and at least one C5-C 60 A heterocyclic group with fused carbocyclic groups.

[0414] Non-limiting examples of nitrogen rings containing depleted π electrons include imidazole rings, pyrazole rings, thiazole rings, isothiazole rings, oxazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, indazole rings, purine rings, quinoline rings, isoquinoline rings, benzo[a]quinoline rings, phthalazine rings, naphthidine rings, quinoxaline rings, quinazoline rings, cyclophosphine rings, phenanthridine rings, acridine rings, phenanthrene-rhein rings, phenazine rings, benzimidazole rings, benziisothiazole rings, benziisoxazole rings, benziisoxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.

[0415] For example, the electron transport region may include a compound represented by formula 601:

[0416] Formula 601

[0417] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0418] In Equation 601,

[0419] Ar 601 C5-C can be substituted or unsubstituted. 60 The carbocyclic group may or may not be substituted C1-C 60 Heterocyclic groups,

[0420] xe11 can be 1, 2, or 3.

[0421] 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.

[0422] xe1 can be an integer selected from 0 to 5.

[0423] 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 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, 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 ),

[0424] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0425] xe21 can be an integer selected from 1 to 5.

[0426] In one implementation, Ar 601 (Given by the quantity of xe11) and R 601 At least one of them (given by the number of xe21) may include a ring containing nitrogen with depleted π electrons.

[0427] In one implementation, Ar in Formula 601 601 Optional from:

[0428] Phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, trefyl, tetraphenyl, styrene, peryl, penfenyl, indoxane, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridyl Azinyl, indazole, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and

[0429] Each of the following substituted groups is selected from at least one of the following: phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, pyrene, trefoil, tetraphenyl, styrene, peryl, penfenyl, indoxanel, dibenzofuranyl, dibenzothiopheneyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, purinel. 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 ),and

[0430] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.

[0431] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.

[0432] In one or more embodiments, Ar in Formula 601 601 It can be anthracene.

[0433] In one or more embodiments, the compound represented by formula 601 may be represented by formula 601-1:

[0434] Formula 601-1

[0435] .

[0436] In Equation 601-1,

[0437] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R)615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,

[0438] L 611 To L 613 Each can be independently combined with L 601 The descriptions are the same.

[0439] xe611 to xe613 can each be independently identical to the definition in xe1.

[0440] R 611 To R 613 Each can independently combine with R 601 The descriptions are the same, and

[0441] 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.

[0442] In one embodiment, L in formulas 601 and 601-1 601 and L 611 To L 613 Each can be selected independently:

[0443] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, treylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, carbazolyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, carbazolyl, carbazolyl, carbazolyl, carbazolyl, carbazolyl, carbazolyl, pyridylene, imidazolyl, pyridylene, thiophene 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

[0444] Each of the following substituted compounds is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, treylene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophene, dibenzo[9,10]phenylene, pentaphenylene, thiophene, carbazolyl, dibenzo[9,10]phenylene, thiophene ... Oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisoxazolyl, benzisisoxazolyl, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, 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.

[0445] However, the embodiments disclosed herein are not limited thereto.

[0446] In one or more embodiments, xe1 and xe611 to xe613 in formulas 601 and 601-1 may each be 0, 1 or 2 independently.

[0447] In one or more embodiments, R in formulas 601 and 601-1 601 and R 611 To R 613 Each can be selected independently:

[0448] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, 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, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0449] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[9,10]phenanthryl, pyrene, tyl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, 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[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, tyl, perylene, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, Pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and

[0450] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),and

[0451] Q 601 and Q 602 Each can be independently identical to the one described above.

[0452] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464] .

[0465] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.

[0466] .

[0467] The thickness of the hole blocking layer and the electronic control layer can each be from about 20 Å to about 1,000 Å, for example, from about 30 Å to about 300 Å. When the thickness of the hole blocking layer and the electronic control layer are both within these ranges, the hole blocking layer and the electronic control layer can have excellent hole blocking characteristics or electronic control characteristics without a significant increase in driving voltage.

[0468] The thickness of the electron transport layer can be from about 100 Å to about 1,000 Å, for example, from about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the above range, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in the driving voltage.

[0469] 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.

[0470] 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, and 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. The ligand coordinating with the metal ion of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.

[0471] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2:

[0472] .

[0473] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0474] The electron injection layer may have: i) a single-layer structure including a single layer (including a single material); ii) a single-layer structure including a single layer (including multiple different materials); or iii) a multi-layer structure having multiple layers (including multiple different materials).

[0475] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0476] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0477] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0478] The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

[0479] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0480] The alkali metal compounds may be selected from alkali metal oxides (such as Li2O, Cs2O, or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In one embodiment, the alkali metal compounds may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0481] The alkaline earth metal compounds may be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) or Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compounds may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0482] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments disclosed herein are not limited thereto.

[0483] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may respectively include alkali metal ions, alkaline earth metal ions, and rare earth metal ions as described above, and the ligands coordinated with the metal ions of alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of this disclosure are not limited thereto.

[0484] 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 any combination thereof as described above. In one or more 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 organic materials.

[0485] The thickness of the electron injection layer can be from about 1 Å to about 100 Å, for example, from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0486] Second electrode 190

[0487] The second electrode 190 may be disposed on the organic layer 150 having the above structure. The second electrode 190 may be a cathode (which is an electron injection electrode), and in this regard, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds and combinations thereof, each having a relatively low work function.

[0488] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0489] The second electrode 190 may have a single-layer structure or a multi-layer structure comprising two or more layers.

[0490] Figures 2 to 4 Description

[0491] Figure 2 This is a schematic diagram of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are stacked sequentially in the order described herein. Figure 3 This is a schematic diagram of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are stacked sequentially in the order described herein. Figure 4 This is a schematic diagram of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are stacked sequentially in the order described herein.

[0492] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be bonded by reference. Figure 1 To understand, use the presented description.

[0493] In the organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass through the first electrode 110 and the first capping layer 210 toward the outside, wherein the first electrode 110 can be a semi-transparent electrode or a transmissive electrode. In the organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass through the second electrode 190 and the second capping layer 220 toward the outside, wherein the second electrode 190 can be a semi-transparent electrode or a transmissive electrode.

[0494] According to the principle of constructive interference, the first capping layer 210 and the second capping layer 220 can increase the external luminescence efficiency.

[0495] The first capping layer 210 and the second capping layer 220 can each be an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including organic and inorganic materials.

[0496] At least one of the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalene phthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents containing at least one element selected from: oxygen (O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0497] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0498] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.

[0499] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of this disclosure are not limited thereto:

[0500] .

[0501] The above text has already combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described, but the embodiments disclosed herein are not limited thereto.

[0502] The layers constituting the hole transport region, the emitter layer, and the electron transport region can each be formed in a region or a set region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0503] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed by vacuum deposition, the deposition can be carried out at a deposition temperature of about 100 °C to about 500 °C, and at a deposition temperature of about 10 °C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed. -8 To about 10 -3 The vacuum level of Torr is approximately 0.01. / sec to approximately 100 The deposition was carried out at a rate of / sec.

[0504] When the layer constituting the hole transport region, the emitter layer, and the layer constituting the electron transport region are formed by spin coating, the spin coating can be carried out at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80 °C to about 200 °C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed.

[0505] equipment

[0506] Organic light-emitting devices can be included in a variety of devices.

[0507] Another aspect of this disclosure provides an apparatus including an organic light-emitting device.

[0508] The device may be, for example, a light-emitting device, an authentication device, or an electronic device, but embodiments of this disclosure are not limited thereto.

[0509] Light-emitting devices can be used as various displays, light sources, etc.

[0510] The authentication device may be, for example, a biometric authentication device used to authenticate an individual by using biometric information from a biometric body (e.g., fingertip, pupil, etc.).

[0511] In addition to organic light-emitting devices, authentication devices may further include biometric information collectors.

[0512] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but embodiments of this disclosure are not limited thereto.

[0513] In addition to the organic light-emitting device, the light-emitting device may further include a thin-film transistor (TFT), which includes a source electrode and a drain electrode. One of the source and drain electrodes of the TFT may be in electrical contact with one of the first and second electrodes of the organic light-emitting device. The light-emitting device can be used as various displays, light sources, etc.

[0514] General definition of substituents

[0515] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group of a straight-chain or branched aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, preferably C1-C2. 20 Alkyl groups, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is used in conjunction with alkyl groups.60 "alkylene" refers to C1-C 60 Alkyl groups have essentially the same divalent structure.

[0516] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 The alkyl group has at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes have divalent groups with essentially the same structure.

[0517] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 An alkyl group having at least one carbon-carbon triple bond at its middle or end, and non-limiting examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 The alkynyl group is a divalent group with essentially the same structure.

[0518] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 The monovalent group represented by alkyl is preferably C1-C. 20 Alkoxy groups, and non-limiting examples of them include methoxy, ethoxy, and isopropoxy groups.

[0519] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have divalent groups with essentially the same structure.

[0520] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom and 1 to 10 carbon atoms, and non-limiting examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. The term "C1-C" as used herein is also used. 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with essentially the same structure.

[0521] The terminology used in this article is C3-C. 10 Cycloalkenyl refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring, at least one carbon-carbon double bond, and lacking aromaticity, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with essentially the same structure.

[0522] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiopheneyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups have divalent groups with essentially the same structure.

[0523] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms), preferably C6-C. 20 Aryl, and as used herein by the term "C6-C" 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and trefyl. When C6-C... 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, these rings can be fused together.

[0524] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom in addition to 1 to 60 carbon atoms), preferably C1-C. 20 heteroaryl. As used in this article, "C1-C" 60 "Hypo-heteroaryl" refers to a divalent group that has a heterocyclic aromatic system (in addition to 1 to 60 carbon atoms, it has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom). C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C...60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, these rings can fused together.

[0525] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein by the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).

[0526] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused together, with only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused polycyclic group.

[0527] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused together, with at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom in addition to the carbon atoms, and lacking aromaticity throughout its molecular structure. A non-limiting example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused heterocyclic group.

[0528] As used in this article, the term "C5-C" 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms (all of which are carbon atoms). For example, the term "C5-C" as used herein... 60 "Carbocyclic group" refers to aromatic carbocyclic groups or non-aromatic carbocyclic groups. (C5-C) 60 The carbocyclic group can be cyclic (e.g., benzene), monovalent (e.g., phenyl), or divalent (e.g., phenylene). In one or more embodiments, depending on the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon ring group can be a trivalent group or a tetravalent group.

[0529] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to C5-C60 Carbocyclic groups have essentially the same structure, except that, in addition to carbon as the cyclic atom (the number of carbon atoms can be 1 to 60), at least one heteroatom selected from N, O, Si, P and S is used.

[0530] 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:

[0531] 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;

[0532] 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-C10 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 );

[0533] 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;

[0534] Each is substituted by at least one of the following 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: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, 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

[0535] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),and

[0536] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.

[0537] As used herein, “Ph” refers to phenyl, “Me” refers to methyl, “Et” refers to ethyl, and “ter-Bu” or “Bu” refers to ethyl. t "Refers to tert-butyl, and as used herein, the term "OMe" refers to methyl methacrylate (MMA).

[0538] As used in this article, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C2 bond. 60 Aryl groups are substituted phenyl groups.

[0539] As used in this article, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group." In other words, "terphenyl" is a phenyl group with a C6-C substituted biphenyl group. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.

[0540] Unless otherwise defined, as used herein, * and *' refer to the binding site with the adjacent atom in the corresponding formula.

[0541] The compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail below with reference to synthesis examples and embodiments. The term "using B instead of A" used to describe the synthesis examples indicates that the same molar equivalent of B is used instead of A.

[0542] Example

[0543] Synthesis Example 1: Synthesis of Compound 1

[0544]

[0545] 5 g (0.017 mol) of (10-phenylanthracene-9-yl)boric acid, 3 g (0.0085 mol) of 2,7-dibromopyrene, 2.3 g (0.017 mol) of K₂CO₃, and 2.7 g (0.0085 mol) of tetrabutylammonium bromide were dissolved in 200 mL of water and toluene (1:1) as solvent, and stirred under reflux at 110 °C for 2 hours. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 2.4 g (80% yield) of compound 1.

[0546] Synthesis Example 2: Synthesis of Compound 2

[0547]

[0548] 5 g (0.017 mol) of (10-phenylanthracene-9-yl)boric acid, 3.3 g (0.0085 mol) of 2,8-dibromochlorophenate, 2.3 g (0.017 mol) of K₂CO₃, and 2.7 g (0.0085 mol) of tetrabutylammonium bromide were dissolved in 200 mL of water and toluene (1:1) as solvent, and stirred under reflux at 110 °C for 2 hours. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 2.0 g (66% yield) of compound 2.

[0549] Quantum chemical (density functional theory DFT) calculations were performed on compounds 1 and 2 according to one or more embodiments using the quantum chemical calculation program Gaussian 09 (manufactured by Gaussian Inc., Wallingford, CT). In the calculations, B3LYP was used as the hybrid functional for ground-state structure optimization, and 6-311G(d,p) was used as the basis set. Information on the structural / electronic properties of the optimized structures was obtained, and time-dependent density functional theory (TD-DFT) was used for structural optimization to obtain the properties of the singlet and triplet excited states, and the triplet energy values ​​were obtained.

[0550] Table 1

[0551]

[0552] Compound 1

[0553] ,

[0554] Compound 2

[0555] .

[0556] E T1 For the lowest excited triplet energy level, E T2 It is the second lowest excited triplet level, and E T3 It is the third lowest excited triplet energy level.

[0557] When Δ(E T3 – E T2 ) > Δ(E T2 – E T1 When Δ(E) is reached, the nonradiative transition from the third low-excited triplet level to the second low-excited triplet level via an internal transition from the TTF of the two triplet states (T1 / T2) of the lowest excited triplet level is forbidden. Therefore, satisfying Δ(E) T3 – ET2 ) > Δ(E T2 – E T1 Compounds of this type can be converted to singlet state via TTF and have a high singlet state conversion rate.

[0558] The results in Table 1 confirm that compounds 1 and 2 satisfy Δ(E) T3 – E T2 ) > Δ(E T2 – E T1 Therefore, compounds 1 and 2 have significantly high singlet state conversion rates via TTF.

[0559] Organic light-emitting devices, including those containing anthracene compounds, can have low driving voltage, high efficiency, and long lifetime, and can also have a large amount of delayed fluorescence components.

[0560] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments.

[0561] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation rather than as terms of degree, and are intended to describe the inherent biases in measurements or calculations that would be recognized by one of ordinary skill in the art.

[0562] Any numerical range described herein is intended to include all subranges of the same numerical precision falling within the described range. For example, the range “1.0 to 10.0” is intended to include all subranges (and inclusive) between the described minimum value of 1.0 and the described maximum value of 10.0, i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit described in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly describe any subranges falling within the scope expressly described herein.

[0563] Although 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 therein without departing from the spirit and scope defined by the appended claims and their equivalents.

Claims

1. An anthracene compound represented by Formula 1: Formula 1 ， in, In Equation 1, X is a group represented by formula 4-3: ， In Equation 4-3, * and *' each indicate the binding site with the adjacent atom. m1 is 1. Where a11 is 0, by *-(L 11 ) a11 -*' indicates a single bond, and a12 is 0, which is determined by *-(L 12 ) a12 -*' indicates a single key. R 11 and R 12 Each is independently unsubstituted C6-C 60 Aryl, R 13 and R 14 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, amidine, hydrazine, and hydrazone. b11 and b12 are each independently 1. b13 and b14 are each independent integers selected from 1 to 8. m2 is 1. Wherein, the anthracene compounds satisfy 2E T1 ≥ E T2 E T1 E represents the lowest excited triplet energy level of the anthracene compound. T2 This is the second low-excited triplet energy level of the anthracene compound, and E T1 and E T2 The value is evaluated by density functional theory method using a Gaussian procedure with structure optimized at the B3LYP / 6-311G(d,p) level.

2. The anthracene compound according to claim 1, wherein R 11 and R 12 Each is selected independently from: Phenyl, biphenyl, terphenyl, pentaphenyl, indole, naphthyl, azulel, heptatenyl, indole, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[9,10]phenanthryl, pyrene, trefyl, tetraphenyl, styrene, peryl, pentaphenyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, and ovolene.

3. The anthracene compound according to claim 1, wherein R 11 and R 12 Each group is independently selected from those represented by free formulas 5-1 to 5-19: ， in, In equations 5-1 to 5-19, Y 31 Selected from C(Z) 33 (Z) 34 ), Z 31 To Z 34 Each is independently selected from hydrogen. e2 is 1 or 2. e3 is an integer selected from 1 to 3. e4 is an integer selected from 1 to 4. e5 is an integer selected from 1 to 5. e6 is an integer selected from 1 to 6. e7 is an integer selected from 1 to 7. e9 is an integer selected from 1 to 9, and * indicates the binding site with adjacent atoms.

4. The anthracene compound according to claim 1, wherein R 11 and R 12 Each is independently represented by equations 6-1 to 6-3: ， in, In equations 6-1 to 6-3, and * Indicates the binding site with adjacent atoms.

5. The anthracene compound according to claim 1, wherein the anthracene compound is represented by formula 1-2: Formula 1-2 ， in, In Equation 1-2, X, R 11 R 12 Both m2 and m2 are independently identical to those described by combination 1.

6. The anthracene compound according to claim 5, wherein: In formula 1-2, X is a group represented by formula 4-3, and R 11 and R 12 Each group is independently selected from those represented by free formulas 6-1 to 6-3: ， In Equation 4-3, * and *' each indicate a binding site with an adjacent atom. ， Among them, in equations 6-1 to 6-3, * Indicates the binding site with adjacent atoms.

7. The anthracene compound according to claim 1, wherein the anthracene compound is selected from compound 2: Compound 2 。 8. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An organic layer comprising an emission layer is disposed between the first electrode and the second electrode, and the organic layer comprising the emission layer. The organic light-emitting device includes at least one of the anthracene compounds according to any one of claims 1 to 7.

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

10. The organic light-emitting device according to claim 8, wherein the emitting layer comprises the anthracene compound.

11. The organic light-emitting device according to claim 10, wherein the anthracene compound is a compound that emits delayed fluorescence.

12. The organic light-emitting device according to claim 11, wherein: The emitter layer further includes a dopant, and the anthracene compound is the host material; or The emitter layer comprises only the anthracene compounds.

13. The organic light-emitting device according to claim 12, wherein the dopant is a fluorescent dopant.

14. The organic light-emitting device according to claim 12, wherein the dopant comprises an aromatic amine compound, a styrene amine compound, or any combination thereof.

15. The organic light-emitting device of claim 9, wherein the hole transport region comprises a p-dopant having a lowest unoccupied molecular orbital energy level of -3.5 eV or less.

Images