Fused ring compound, light-emitting device including the same, and electronic device including the light-emitting device
By using fused ring compounds as intermediate layer materials in organic light-emitting devices, the hole and electron transport characteristics are optimized, solving the problems of high driving voltage, low luminous efficiency and short lifetime in the prior art, and realizing the performance of high efficiency and long lifetime light-emitting devices.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2025-12-03
- Publication Date
- 2026-06-05
AI Technical Summary
Existing organic light-emitting devices have certain limitations in terms of performance, especially in terms of driving voltage, luminous efficiency and lifetime.
A specific fused-ring compound is used as the intermediate layer material of the light-emitting device. The specific structure is represented by Formula 1, which includes C5-C30 carbon ring groups or C1-C30 heterocyclic groups. The device performance is improved by optimizing the hole and electron transport characteristics.
It achieves light-emitting device performance with low driving voltage, high maximum external quantum efficiency, narrow emission spectrum half-width, low roll-off ratio and long lifetime.
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Figure CN122145496A_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefits, and all benefits arising therefrom, to Korean Patent Application No. 10-2024-0177904 filed on December 3, 2024, and Korean Patent Application No. 10-2025-0188566 filed on December 2, 2025, the entire contents of which are incorporated herein by reference. Technical Field
[0003] This subject matter relates to fused ring compounds, light-emitting devices including said fused ring compounds, and electronic devices including said light-emitting devices. Background Technology
[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that feature wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed. Furthermore, OLEDs can produce full-color images.
[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an intermediate layer disposed between the anode and cathode, including an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes supplied from the anode move towards the emission layer through the hole transport region, and electrons supplied from the cathode move towards the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. Excitons transition from an excited state to the ground state, thereby producing light. Summary of the Invention
[0006] A fused-ring compound is provided, a light-emitting device comprising the fused-ring compound, and an electronic device comprising the light-emitting device.
[0007] Other aspects will be set forth in part in the following detailed description, and in part will become apparent from that detailed description, or may be learned through practice of the exemplary embodiments presented herein.
[0008] According to one aspect, fused-ring compounds represented by Formula 1 are provided:
[0009] Formula 1
[0010]
[0011] In Equation 1,
[0012] Rings CY1 to CY8 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,
[0013] L1 is O, S, or C(R) 1a (R) 1b ),
[0014] L2 is O, S, or C(R) 2a (R) 2b ),
[0015] The condition is that when L1 is 0 and L2 is 0, the fused ring compound has a symmetrical structure.
[0016] R1 to R9, R 1a R 1b R 2a and R 2b Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),
[0017] Two or more of R1 to R9 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0018] R 1a and R 1b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0019] R 2a and R 2b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0020] a1 to a8 are each an independent integer from 0 to 10.
[0021] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 The heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are each independently:
[0022] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio,
[0023] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or a combination thereof,
[0024] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q)27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or a combination thereof,
[0025] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 ),or
[0026] Its combination, and
[0027] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0028] According to another aspect, the light-emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer includes an emitting layer, and wherein the intermediate layer includes at least one fused ring compound represented by Formula 1.
[0029] According to another aspect, the light-emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first and second electrodes, wherein the intermediate layer includes an emitting layer, wherein the emitting layer includes a first body, a second body, and at least one fused-ring compound represented by Formula 1, wherein the first body includes a hole-transporting compound, and the second body includes an electron-transporting compound. In this document, the fused-ring compound represented by Formula 1 in the light-emitting device of such an embodiment may have the same definition as the fused-ring compound represented by Formula 1 described above or below, except that it does not include the condition "when L1 is 0 and L2 is 0, the fused-ring compound has a symmetrical structure". Therefore, the light-emitting device of such an embodiment may cover the light-emitting device described above.
[0030] According to another aspect, the electronic device includes any of the light-emitting devices described above. Attached Figure Description
[0031] From combination Figure 1 The above and other aspects, features and advantages of some exemplary embodiments will become clearer from the following detailed description. Figure 1 It is a schematic cross-sectional view of a light-emitting device according to one or more embodiments. Detailed Implementation
[0032] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this respect, these exemplary embodiments may take different forms and should not be construed as limited to the detailed description set forth herein. Therefore, exemplary embodiments are described in further detail below and with reference to the accompanying drawings only to illustrate some aspects and features. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.
[0033] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are also intended to include the plural forms unless the context clearly indicates otherwise. The term “or” means “and / or”. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.
[0034] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer, or portion discussed below may be referred to as the second element, component, region, layer, or portion.
[0035] Exemplary embodiments are described herein with reference to cross-sectional views, which are schematic diagrams of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of the regions nor to limit the scope of the claims.
[0036] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.
[0037] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless expressly defined herein.
[0038] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviations from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±30%, 20%, 10%, or 5%.
[0039] Fused ring compounds
[0040] One aspect provides fused-ring compounds represented by Formula 1:
[0041] Formula 1
[0042] .
[0043] In Equation 1, rings CY1 to CY8 are each independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.
[0044] In one or more embodiments, rings CY1 to CY8 may each independently be a phenyl group, a naphthyl group, a phenanthrene group, an anthracene group, a pyridine group, a pyrimidine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzothiophene group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzothiophene group.
[0045] In one or more embodiments, rings CY1 to CY8 may each be independently a phenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzothiophene group.
[0046] In one or more embodiments, cyclo(CY1) to cyclo(CY8) may each be a phenyl group.
[0047] In Equation 1, L1 is O, S, or C(R) 1a (R) 1b Here, R 1a and R 1b Each can be as described in this article.
[0048] In Equation 1, L2 is O, S, or C(R) 2a (R) 2b Here, R 2a and R 2b Each can be as described in this article.
[0049] In one or more implementations, L1 and L2 may be the same as each other.
[0050] In one or more implementations, L1 and L2 may be different from each other.
[0051] In one or more embodiments,
[0052] L1 and L2 can each be 0;
[0053] L1 and L2 can each be S; or
[0054] L1 can be C(R) 1a (R) 1b L2 can be C(R) 2a (R) 2b ), and R 1a R 1b R 2a and R 2b Each can be independently substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, or substituted or unsubstituted C6-C 60 Aryl.
[0055] In Formula 1, when L1 is O and L2 is O, the fused ring compound has a symmetrical structure.
[0056] As used herein, the term "symmetric structure" refers to a structure that is bilaterally symmetrical with respect to the boron (B) atom and the carbon (C) atom to which R9 is bonded in Formula 1.
[0057] In one or more embodiments, the fused ring compound represented by Formula 1 may have a symmetrical or asymmetrical structure, preferably a symmetrical structure.
[0058] In Equation 1, R1 to R9, R 1a R 1b R 2a and R 2bEach of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9).
[0059] In one or more embodiments, R1 to R9, R 1a R 1b R 2a and R 2b Each can be independently:
[0060] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C20 alkoxy, or C1-C 20 Alkylthio;
[0061] Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;
[0062] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;
[0063] Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or
[0064] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and
[0065] Q1 to Q9 can be independently defined as follows:
[0066] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;
[0067] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or
[0068] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.
[0069] In one or more embodiments, R1 to R9, R 1a R 1b R 2a and R 2b Each can be independently:
[0070] Hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;
[0071] A group represented by one of formulas 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-350; or
[0072] -N(Q4)(Q5):
[0073]
[0074]
[0075]
[0076]
[0077]
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084]
[0085]
[0086]
[0087]
[0088]
[0089]
[0090]
[0091]
[0092] .
[0093] In equations 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * The symbols indicate the binding sites with adjacent atoms. "Ph" represents phenyl, "TMS" represents trimethylsilyl, and "TMG" represents trimethylgermanyl.
[0094] In one or more embodiments, R1 to R9 can each be independently:
[0095] Hydrogen, deuterium, -F, or cyano;
[0096] C1-C that is not substituted or is substituted with deuterium, -F, cyano, or a combination thereof 20 Alkyl; or
[0097] Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, or a combination thereof substituted with cyclopentyl, cyclohexyl, or phenyl.
[0098] As used in this article, C1-C 60 Alkyl or C1-C 20 Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, etc.
[0099] In Equation 1, two or more of R1 to R9 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.
[0100] In Equation 1, R 1a and R 1b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.
[0101] In Equation 1, R 2a and R 2b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.
[0102] In Equation 1, a1 to a8 represent the number of R1 to R8, respectively, where a1 to a8 are each an independent integer from 0 to 10, for example, an integer from 0 to 4. When a1 is 2 or greater, two or more R1s may be the same or different from each other; when a2 is 2 or greater, two or more R2s may be the same or different from each other; when a3 is 2 or greater, two or more R3s may be the same or different from each other; when a4 is 2 or greater, two or more R4s may be the same or different from each other; when a5 is 2 or greater, two or more R5s may be the same or different from each other; when a6 is 2 or greater, two or more R7s may be the same or different from each other; and when a8 is 2 or greater, two or more R8s may be the same or different from each other.
[0103] In one or more embodiments, in Formula 1,
[0104] a1 to a4 can each be an integer from 1 to 10, for example, an integer from 1 to 4, and
[0105] R1, R2, R3, and R4 may not be hydrogen.
[0106] In one or more embodiments, the fused-ring compound represented by Formula 1 can be represented by Formula 1-1:
[0107] Equation 1-1
[0108] .
[0109] In Equation 1-1, L1, L2, R1 to R9, and a1 to a8 can each be as described herein.
[0110] In one or more embodiments, the fused-ring compound represented by Formula 1 can be represented by Formula 1-2:
[0111] Formula 1-2
[0112] .
[0113] In Equation 1-2,
[0114] L1, L2, R5 to R8, and a5 to a8 can each be as described in this document, and
[0115] Z1 to Z4 can each be independently described as relating to R1 to R4.
[0116] In one or more embodiments, Z1 to Z4 in Equations 1-2 can each be independently:
[0117] Hydrogen, deuterium, -F, or cyano;
[0118] C1-C that is not substituted or is substituted with deuterium, -F, cyano, or a combination thereof 20 Alkyl; or
[0119] Each of the following substituted groups—either unsubstituted or substituted with: cyclopentyl, cyclohexyl, or phenyl: deuterium, -F, cyano, C1-C— 20 Alkyl, phenyl, or combinations thereof.
[0120] In one or more embodiments, the fused-ring compound represented by Formula 1 may be one of compounds 1 to 54:
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129] .
[0130] The fused-ring compound represented by Formula 1 has the structure described above and therefore exhibits excellent light-emitting properties. Consequently, electronic devices, such as light-emitting devices, comprising at least one fused-ring compound represented by Formula 1 can exhibit low driving voltage, high maximum external quantum efficiency, narrow half-width (FWHM), low roll-off ratio, and / or long lifetime.
[0131] In one or more embodiments, the FWHM of the emission peak in the emission spectrum of the fused ring compound represented by Formula 1 may be about 5 nanometers (nm) to about 35 nm, about 10 nm to about 35 nm, about 15 nm to about 35 nm, about 5 nm to about 34 nm, about 10 nm to about 34 nm, about 15 nm to about 34 nm, about 5 nm to about 33 nm, about 10 nm to about 33 nm, or about 15 nm to about 33 nm.
[0132] In one or more embodiments, the emission peak wavelength (i.e., the maximum emission wavelength, or the peak emission wavelength) in the emission spectrum of the fused ring compound represented by Formula 1 may be from about 490 nm to about 550 nm, for example from about 500 nm to about 540 nm.
[0133] The synthetic method of the fused-ring compound represented by Formula 1 is as can be recognized by those skilled in the art and by referring to the synthetic examples described below.
[0134] Light-emitting devices
[0135] The fused-ring compound represented by Formula 1 is suitable for use in the intermediate layer of a light-emitting device, for example, suitable as a material for an emitting layer in the intermediate layer. Therefore, another aspect provides a light-emitting device comprising: a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer includes an emitting layer, and wherein the intermediate layer includes at least one of the fused-ring compounds represented by Formula 1.
[0136] The light-emitting device may include an intermediate layer comprising at least one of a fused-ring compound represented by Formula 1 as described herein, and thus the light-emitting device may have a low driving voltage, high maximum external quantum efficiency, narrow FWHM, low roll-off ratio, and / or long lifetime.
[0137] Fused-ring compounds represented by Formula 1 can be used between electrode pairs in a light-emitting device. For example, at least one of the fused-ring compounds represented by Formula 1 may be included in the emitting layer. In this respect, the emitting layer may further include a host. Based on weight, the amount of the host in the emitting layer may be greater than the amount of the at least one fused-ring compound represented by Formula 1 in the emitting layer. The emitting layer may emit red light, green light, or blue light. For example, the emitting layer may emit green light.
[0138] In one or more embodiments, the emission peak wavelength of the light emitted from the emission layer may be about 490 nm to about 550 nm, or about 500 nm to about 540 nm.
[0139] The emission layer may further include a body. The body may be as described herein.
[0140] The first electrode may be the anode of the hole injection electrode and the second electrode may be the cathode of the electron injection electrode; or the first electrode may be the cathode of the electron injection electrode and the second electrode may be the anode of the hole injection electrode.
[0141] In one or more embodiments, in the light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the intermediate layer may further include a hole transport region disposed between the first electrode and the emitting layer, and an electron transport region disposed between the emitting layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, an auxiliary layer, or a combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
[0142] As used herein, the term "intermediate layer" refers to a single layer or multiple layers disposed between the first and second electrodes of a light-emitting device. In addition to organic compounds, "intermediate layer" may also include organometallic complexes containing metals.
[0143] In one or more embodiments, the emission layer may have a configuration according to the first or second embodiment:
[0144] First implementation of the emission layer
[0145] The emitting layer may include at least one fused-ring compound represented by Formula 1, and the fused-ring compound represented by Formula 1 may act as an emitter, for example, a delayed fluorescence emitter. That is, the fused-ring compound represented by Formula 1 may be the emitter. For example, the ratio of the luminescence component emitted from the fused-ring compound represented by Formula 1 to all luminescence components of the emitting layer may be about 80% or greater, about 85% or greater, about 90% or greater, or about 95% or greater. The light emitted from the fused-ring compound represented by Formula 1 may be green light. The emitting layer may further include a sensitizer, and the sensitizer may be different from the fused-ring compound represented by Formula 1. The sensitizer may be an organometallic compound, a delayed fluorescence material, a transient fluorescence material, or a combination thereof. Based on 100 parts by weight of the emitting layer, the amount (by weight) of the sensitizer may be from about 0.01 parts by weight to about 10 parts by weight.
[0146] Second implementation of the emission layer
[0147] The emitter layer may include at least one fused-ring compound represented by Formula 1, and the fused-ring compound represented by Formula 1 may act as a sensitizer or as an auxiliary dopant. That is, the fused-ring compound represented by Formula 1 may be a sensitizer or an auxiliary dopant. The sensitizer may be used to efficiently transfer excitons from the host to the emitter. The emitter layer may further include an emitter, and the emitter may be different from the fused-ring compound represented by Formula 1. The emitter may be an organometallic compound, a transient fluorescent material, a delayed fluorescent material, or a combination thereof.
[0148] An emitter is a material that can receive excitons from a host, sensitizer, and / or auxiliary dopant and emit light as the excitons transition to the ground state.
[0149] Based on 100 parts by weight of the emitter layer, the amount of the fused ring compound represented by Formula 1 in the first and second embodiments may be from about 0.01 parts by weight to about 40 parts by weight, from about 0.1 parts by weight to about 20 parts by weight, or from about 1 part by weight to about 20 parts by weight.
[0150] The organometallic compounds in the first and second embodiments may include a transition metal and n ligands bound to the transition metal, wherein n may be an integer from 1 to 4.
[0151] In one or more embodiments, the transition metal in the organometallic compound may be iridium (Ir), osmium (Os), platinum (Pt), or palladium (Pd).
[0152] In one or more embodiments, in the organometallic compound, the transition metal may be iridium (Ir) or osmium (Os), n may be 3, and at least one of the n ligands may be a bidentate ligand. The bidentate ligand may include a phenyl group and / or a pyridine group, each of which is bonded to the transition metal. For example, at least one bidentate ligand may include -F, cyano, silyl, or combinations thereof.
[0153] In one or more embodiments, in the organometallic compound, the transition metal may be platinum (Pt) or palladium (Pd), n may be 1, and the ligand may be a tetradentate ligand. The tetradentate ligand may include, for example, a carbene portion bound to the transition metal.
[0154] In one or more embodiments, the organometallic compound may be an organometallic compound represented by Formula 3 and / or an organometallic compound represented by Formula 5. Formulas 3 and 5 are as described herein.
[0155] The delayed fluorescence material in the first and second embodiments may be, for example, a thermally activated delayed fluorescence material. In one or more embodiments, the delayed fluorescence material may be a multiple resonance thermally activated delayed fluorescence material.
[0156] Multiple resonance thermally activated delayed fluorescence materials can be polycyclic compounds that i) do not contain transition metals and ii) include two or more C3-C atoms. 60 A core of fused cyclic groups. Here, the two C3-C groups in the core... 60 Cyclic groups can fuse together while sharing boron (B) or nitrogen (N).
[0157] In one or more embodiments, the delayed fluorescence material may be a polycyclic compound represented by Formula 4. Formula 4 may be as described herein.
[0158] The transient fluorescent materials in the first and second embodiments can be amino-containing compounds, styrene-containing compounds, etc. For example, transient fluorescent materials may include naphthyl groups, fluorene groups, spirodifluorene groups, benzo[9,10]fluorene groups, dibenzo[9,10]fluorene groups, phenanthrene groups, anthracene groups, fluoranthene groups, benzo[9,10]phenanthrene groups, pyrene groups, etc. Group, tetraphenyl group (butanol group), Groups, Group, pentylenetetrazol group, indene-anthracene group, group represented by any one of formulas 501-1 to 501-21, or a combination thereof:
[0159]
[0160] .
[0161] In one or more embodiments, the transient fluorescent material may include a compound represented by formula 501A or 501B:
[0162] .
[0163] In formulas 501A and 501B,
[0164] Ar 501 It can be a naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, Groups, Group, pentylenetetrazolium group, indene-anthracene group, bianthracite group, or a group represented by any one of formulas 501-1 to 501-21,
[0165] R 511 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or -Si(Q) 501 (Q) 502 (Q) 503 ),
[0166] xd5 can be an integer from 0 to 10.
[0167] L 501 To L 503 Each can be independently:
[0168] Single key; or
[0169] Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Heteroaryl groups, divalent non-aromatic fused polycyclic groups, or divalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 501 (Q) 502 (Q) 503 ), or a combination thereof,
[0170] xd1 to xd3 can each be 1, 2, or 3 independently.
[0171] R 501 and R 502 Each can be independently substituted or substituted with one of the following: phenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole group, triazinyl, dibenzofuranyl, dibenzothiopheneyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidoyl, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 501 (Q) 502 (Q) 503 ), or a combination thereof,
[0172] Z 11 Each of the following can be C1-C that has not been replaced or has been replaced as follows: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 501 (Q) 502 (Q) 503 ), or a combination thereof,
[0173] xd4 can be 1, 2, 3, 4, 5, or 6, and
[0174] Q 501 To Q 503 Each can be independently hydrogen, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.
[0175] In one or more embodiments, the transient fluorescent material may include a compound represented by formula 501A or 501B, wherein xd4 in formula 501A may be 1, 2, 3, 4, 5 or 6, and xd4 in formula 501B may be 2, 3 or 4.
[0176] Description of the subject
[0177] The emitter layer may include m1 types of substrates. The m1 types of substrates in the emitter layer may include hole transport compounds, electron transport compounds, bipolar compounds, or combinations thereof. Neither the first substrate nor the second substrate may contain a transition metal.
[0178] In one or more embodiments, m1 in the emitter layer may be 2, and the two bodies may include a hole transport compound and an electron transport compound, wherein the hole transport compound and the electron transport compound may be different from each other.
[0179] In one or more embodiments, the hole-transporting compound may include at least one π-electron-rich C3-C 60 Cyclic groups, and may not include electron transport groups. Examples of electron transport groups may include cyano groups, fluorine groups, cyclic groups containing nitrogen lacking π electrons, phosphine oxide groups, sulfoxide groups, etc.
[0180] As used in this article, "a cyclic group containing nitrogen lacking π electrons" can refer to a group having at least one π electron-deficient nitrogen cyclic group. * -N= *' C1-C, which is part of the cyclic component 60Heterocyclic groups. Examples of cyclic groups containing nitrogen that lacks π electrons include triazine groups, imidazole groups, etc.
[0181] As used in this article, “π-electron-rich C3-C” 60 "Cyclic group" may not include * -N= *' C3-C, part of the cyclic component 60 Cyclic groups. π-electron-rich C3-C groups. 60 Examples of cyclic groups may include phenyl groups, naphthyl groups, benzo[9,10]phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indole-dibenzofuran groups, indole-dibenzothiophene groups, indole-carbazole groups, naphthanobenzofuran groups, naphthanobenzothiophene groups, benzocarbazole groups, phenanthrene-benzofuran groups, phenanthrene-benzothiophene groups, naphthiocarbazole groups, dinaphthanofuran groups, dinaphthiophene groups, dibenzocarbazole groups, etc.
[0182] In one or more embodiments, the hole transport compound may include two or more carbazole groups.
[0183] In one or more embodiments, the electron transport compound may be a compound comprising at least one electron transport group. The electron transport group may be a cyano group, a fluorine group, or a C1-C group containing nitrogen with a lack of π electrons. 60 Cyclic groups, phosphine oxide groups, sulfoxide groups, or combinations thereof. In one or more embodiments, the electron transport compound may include a triazine group.
[0184] In one or more embodiments, the electron transport compound may include at least one electron transport group (e.g., a triazine group) and at least one π-electron-rich C3-C group. 60 Cyclic groups (e.g., phenyl groups, naphthyl groups, benzo[9,10]phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indole-dibenzofuran groups, indole-dibenzothiophene groups, indole-carbazole groups, naphthylbenzofuran groups, naphthylbenzothiophene groups, benzocarbazole groups, phenanthrene-benzofuran groups, phenanthrene-benzothiophene groups, naphthylcarbazole groups, dinaphthylfuran groups, dinaphthiophene groups, dibenzocarbazole groups, or combinations thereof).
[0185] In one or more embodiments, the hole transport compound may be a compound represented by Formula 6:
[0186] Formula 6
[0187] .
[0188] In Equation 6,
[0189] L 61and L 62 Each can be an independent π-electron-rich C3-C that is either unsubstituted or substituted as follows. 60 Cyclic groups: deuterium, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, phenyl, deuterated phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 33 (Q) 34 (Q) 35 ), or a combination thereof,
[0190] e61 and e62 can each be an integer from 1 to 6 independently.
[0191] R 61 To R 64 Each can be independently:
[0192] Hydrogen, deuterium, C1-C 20 Alkyl or deuterated C1-C 20 alkyl;
[0193] C3-C electrons that are not substituted or are substituted as follows 60 Cyclic groups: deuterium, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, phenyl, deuterated phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or
[0194] -Si(Q1)(Q2)(Q3), and
[0195] a63 and a64 can each be an integer from 0 to 7 independently.
[0196] Q1 to Q3 and Q 31 To Q 33 Each can be as described in this article.
[0197] In one or more embodiments, the hole transport compound may be a compound represented by formula 6-1, 6-2 or 6-3:
[0198] Equation 6-1
[0199]
[0200] Formula 6-2
[0201]
[0202] Formula 6-3
[0203] .
[0204] In equations 6-1 to 6-3, L 61 L 62 R 61 To R 64 e61, e62, a63 and a64 can each be as described in this article.
[0205] In one or more embodiments, the hole transport compound may be one of compounds HTH1 to HTH6, but the embodiments are not limited to this:
[0206] .
[0207] In an embodiment, the electron transport compound may be a compound represented by formula 7-1 or 7-2:
[0208] Equation 7-1
[0209]
[0210] Equation 7-2
[0211] .
[0212] In equations 7-1 and 7-2,
[0213] X 74 It can be C(R) 74 ) or N, X 75 It can be C(R) 75 ) or N, and X 76 It can be C(R) 76 ) or N, where X 74 To X 76 At least one of them can be N.
[0214] X 77 It can be C(R) 77 ) or N, and X 78 It can be C(R) 78 ) or N, where X 77 and X 78 At least one of them can be N.
[0215] X 79 It can be O, S, N(R) 79a ), or C(R) 79a (R) 79b ),
[0216] L71 To L 75 Each can be independently represented as its own unsubstituted or substituted C5-C as follows. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 33 (Q) 34 (Q) 35 ), or a combination thereof,
[0217] e71 to e75 can each be an integer from 1 to 10 independently.
[0218] e76 can be an integer from 1 to 4.
[0219] R 71 To R 78 R 79a R 79b and Z 74 To Z 76 Each can be independently:
[0220] Hydrogen, deuterium, -F, or cyano;
[0221] C1-C that is not substituted or is substituted with deuterium, -F, cyano, or a combination thereof 20 alkyl;
[0222] Each of the following C5-Cs was not replaced or was replaced as follows: 30 Carbocyclic groups or C1-C 30 Heterocyclic groups: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or
[0223] -Si(Q1)(Q2)(Q3).
[0224] Q1 to Q3 and Q 31 To Q33 Each can be as described in this article.
[0225] In one or more embodiments, X in Formula 7-1 74 To X 76 Each can be N.
[0226] In one or more embodiments, X in Formula 7-2 77 and X 78 Each can be N.
[0227] In one or more embodiments, L in formulas 7-1 and 7-2 71 To L 75 Each can be independently represented by an unsubstituted or substituted phenyl group, naphthyl group, benzo[9,10]phenanthrene group, dibenzofuran group, dibenzothiophene group, carbazole group, indole-dibenzofuran group, indole-dibenzothiophene group, indole-carbazole group, naphthenofuran group, naphthenobenzothiophene group, benzocarbazole group, phenanthrene-benzofuran group, phenanthrene-benzothiophene group, naphthiocarbazole group, dinaphthenofuran group, dinaphthiophene group, or dibenzocarbazole group: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or combinations thereof.
[0228] In one or more embodiments, the number of L in Formula 7-1 is e71. 71 At least one L of quantity e72 72 At least one L of quantity e73 73 At least one, or combination thereof, may be independently an unsubstituted or substituted dibenzofuran group, dibenzothiophene group, carbazole group, indole-dibenzofuran group, indole-dibenzothiophene group, indole-carbazole group, naphthobenzofuran group, naphthobenzothiophene group, benzocarbazole group, phenanthrene-benzofuran group, phenanthrene-benzothiophene group, naphthocarbazole group, dinaphthofuran group, dinaphthothiophene group, or dibenzocarbazole group: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C)20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or combinations thereof.
[0229] In one or more embodiments, the number of L in Equation 7-2 is e74. 74 At least one L of quantity e75 75 At least one, or combination thereof, may be independently an unsubstituted or substituted dibenzofuran group, dibenzothiophene group, carbazole group, indole-dibenzofuran group, indole-dibenzothiophene group, indole-carbazole group, naphthobenzofuran group, naphthobenzothiophene group, benzocarbazole group, phenanthrene-benzofuran group, phenanthrene-benzothiophene group, naphthocarbazole group, dinaphthofuran group, dinaphthothiophene group, or dibenzocarbazole group: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or combinations thereof.
[0230] In one or more embodiments, the number of L in Formula 7-1 is e71. 71 At least one L of quantity e72 72 At least one L of quantity e73 73 At least one, or a combination thereof, may independently include a carbazole group, an indole-carbazole group, a benzo[a]carbazole group, a naphtho[a]carbazole group, or a dibenzo[a]carbazole group, wherein the nitrogen atom of the pyrrole group in the carbazole group, indole-carbazole group, benzo[a]carbazole group, naphtho[a]carbazole group, or dibenzo[a]carbazole group may be connected via a single bond or via an L-type bond adjacent to the carbazole group, indole-carbazole group, benzo[a]carbazole group, naphtho[a]carbazole group, or dibenzo[a]carbazole group. 71 L 72 and / or L 73 Connected to X in Equation 7-1 74 To X 76 The carbon atom in the 6-membered ring.
[0231] In one or more embodiments, the number of L in Equation 7-2 is e74. 74At least one L of quantity e75 75 At least one, or combination thereof, may be independently an unsubstituted or substituted dibenzofuran group, dibenzothiophene group, carbazole group, indole-dibenzofuran group, indole-dibenzothiophene group, indole-carbazole group, naphthobenzofuran group, naphthobenzothiophene group, benzocarbazole group, phenanthrene-benzofuran group, phenanthrene-benzothiophene group, naphthocarbazole group, dinaphthofuran group, dinaphthothiophene group, or dibenzocarbazole group: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or combinations thereof.
[0232] In one or more embodiments, the number of L in Equation 7-2 is e74. 74 At least one L of quantity e75 75 At least one, or a combination thereof, may independently include a carbazole group, an indole-carbazole group, a benzo[a]carbazole group, a naphtho[a]carbazole group, or a dibenzo[a]carbazole group, wherein the nitrogen atom of the pyrrole group in the carbazole group, indole-carbazole group, benzo[a]carbazole group, naphtho[a]carbazole group, or dibenzo[a]carbazole group may be connected via a single bond or via an L-type bond adjacent to the carbazole group, indole-carbazole group, benzo[a]carbazole group, naphtho[a]carbazole group, or dibenzo[a]carbazole group. 74 and / or L 75 Connected to X in Equation 7-2 77 and X 78 The carbon atom in the 6-membered ring.
[0233] In one or more embodiments, e71 to e73 in Formula 7-1 respectively represent L 71 The quantity up to L 73 The quantity, and for example, can be 1, 2, 3, 4 or 5 independently.
[0234] In one or more embodiments, e74 and e75 in Equation 7-2 respectively represent L 74 Quantity and L 75 The quantity, and for example, can be 1, 2, 3, 4 or 5 independently.
[0235] In one or more embodiments, R in formulas 7-1 and 7-271 To R 78 R 79a R 79b and Z 74 To Z 76 Each can be independently:
[0236] Hydrogen, deuterium, -F, or cyano;
[0237] C1-C that is not substituted or is substituted with deuterium, -F, cyano, or a combination thereof 20 alkyl;
[0238] The phenyl group, naphthyl group, benzo[9,10]phenanthrene group, dibenzofuran group, dibenzothiophene group, carbazole group, indole-dibenzofuran group, indole-dibenzothiophene group, indole-carbazole group, naphthenofuran group, naphthenobenzothiophene group, benzocarbazole group, phenanthrene-benzofuran group, phenanthrene-benzothiophene group, naphthiocarbazole group, dinaphthenofuran group, dinaphthiophene group, or dibenzocarbazole group, respectively, are either unsubstituted or substituted with the following groups: deuterium, -F, cyano, C1-C. 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, -Si(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or
[0239] -Si(Q1)(Q2)(Q3).
[0240] In one or more embodiments, the electron transport compound may be one of compounds ETH1 to ETH8, but the embodiments are not limited to this:
[0241]
[0242] .
[0243] Description of Equation 3
[0244] The organometallic compound in the first and second embodiments of the emitter layer can be an organometallic compound represented by Formula 3:
[0245] Formula 3
[0246] .
[0247] In Equation 3,
[0248] M 31 It can be a transition metal.
[0249] X 11 To X 14 Each can be independently C or N.
[0250] X 11 and M 31 The key between X 12 and M 31 The key between X 13 and M 31 The key between, and X 14 and M 31 Two of the bonds between them can be coordinate bonds, and the other two can be covalent bonds.
[0251] CY 31 To CY 34 Each can be independently classified as C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,
[0252] T 31 Can be a single key, double key, * -N(R 35a )- * '、 * -B(R 35a )- * '、 * -P(R 35a )- * '、 * -C(R 35a (R) 35b )- * '、 * -Si(R 35a (R) 35b )- * '、 * -Ge(R 35a (R) 35b )- * '、 * -S- * '、 * -Se- * '、 * -O- * '、 * -C(=O)- * '、 * -S(=O)- * '、 * -S(=O)2- * '、 * -C(R35a )= * '、 * =C(R 35a )- * '、 * -C(R 35a )=C(R 35b )- * '、 * -C(=S)- * '、 * -C≡C- * 'Not replaced or replaced by at least one R' 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0253] T 32 Can be a single key, double key, * -N(R 36a )- * '、 * -B(R 36a )- * '、 * -P(R 36a )- * '、 * -C(R 36a (R) 36b )- * '、 * -Si(R 36a (R) 36b )- * '、 * -Ge(R 36a (R) 36b )- * '、 * -S- * '、 * -Se- * '、 * -O- * '、 * -C(=O)- * '、 * -S(=O)- * '、 * -S(=O)2- * '、 * -C(R 36a )= * '、 * =C(R 36a )- * '、 * -C(R36a )=C(R 36b )- * '、 * -C(=S)- * '、 * -C≡C- * 'Not replaced or replaced by at least one R' 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0254] T 33 Can be a single key, double key, * -N(R 37a )- * '、 * -B(R 37a )- * '、 * -P(R 37a )- * '、 * -C(R 37a (R) 37b )- * '、 * -Si(R 37a (R) 37b )- * '、 * -Ge(R 37a (R) 37b )- * '、 * -S- * '、 * -Se- * '、 * -O- * '、 * -C(=O)- * '、 * -S(=O)- * '、 * -S(=O)2- * '、 * -C(R 37a )= * '、 * =C(R 37a )- * '、 * -C(R 37a )=C(R 37b )- * '、 * -C(=S)- * '、 *-C≡C- * 'Not replaced or replaced by at least one R' 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0255] T 34 Can be a single key, double key, * -N(R 38a )- * '、 * -B(R 38a )- * '、 * -P(R 38a )- * '、 * -C(R 38a (R) 38b )- * '、 * -Si(R 38a (R) 38b )- * '、 * -Ge(R 38a (R) 38b )- * '、 * -S- * '、 * -Se- * '、 * -O- * '、 * -C(=O)- * '、 * -S(=O)- * '、 * -S(=O)2- * '、 * -C(R 38a )= * '、 * =C(R 38a )- * '、 * -C(R 38a )=C(R 38b )- * '、 * -C(=S)- * '、 * -C≡C- * 'Not replaced or replaced by at least one R' 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10aReplacement C1-C 30 Heterocyclic groups,
[0256] n31 to n34 can each be an integer from 0 to 5 independently, where three or more of n31 to n34 can each be an integer from 1 to 5 independently.
[0257] When n31 is 0, T 31 It may not exist when n32 is 0, T 32 It may not exist when n33 is 0, T 33 It may not exist, and when n34 is 0, T 34 It may not exist.
[0258] When n31 is 2 or greater, there are two or more T 31 They can be the same or different from each other, and when n32 is 2 or greater, there are two or more Ts. 32 They can be the same or different from each other, and when n33 is 2 or greater, there are two or more Ts. 33 They can be the same or different from each other, and when n34 is 2 or greater, two or more Ts 34 They can be the same or different from each other.
[0259] R 31 To R 34 R 35a R 35b R 36a R 36b R 37a R 37b R 38a and R 38b Each of these groups can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),
[0260] a31 to a34 can each be an integer from 0 to 20 independently.
[0261] The quantity of R is a31 31 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0262] The quantity of R is a32 32 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0263] The quantity of R is a33 33 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0264] The quantity of R is a34 34 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10aReplacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0265] R 31 To R 34 R 35a R 35b R 36a R 36b R 37a R 37b R 38a and R 38b Two or more adjacent elements may optionally be combined with each other to form an unsubstituted or at least R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,
[0266] R 10a For example, regarding R 31 As described,
[0267] * and *' Each represents a binding site with an adjacent atom.
[0268] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can each independently be:
[0269] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;
[0270] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q)19 -P(Q) 18 (Q) 19 ), or combinations thereof;
[0271] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q)23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;
[0272] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or
[0273] Its combination, and
[0274] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0275] In one or more embodiments, M in Formula 3 31 It can be Pt, Pd, or Au.
[0276] In one or more embodiments, M in Formula 3 31 It can be Pt or Pd.
[0277] In one or more embodiments, X in Formula 3 11 and M 31 The bond between them can be a coordinate bond.
[0278] In one or more embodiments, in Equation 3, X 11 It can be C, and X 11 and M 31 The bond between them can be a coordinate bond. That is, X in Equation 3 11 It can be C in the carbene part.
[0279] In one or more embodiments, the ring CY in Formula 3 31 To CY 34 Each of these can be independently i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused together, iv) a fused ring group in which two or more second rings are fused together, or v) a fused ring group in which at least one first ring is fused with at least one second ring.
[0280] The first ring can be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, or a thiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and
[0281] The second ring can be an adamantyl group, norbornel group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, or triazine group. Azine group, thiazine group, dihydropyrazine group, dihydropyridine group, or dihydroazinesicyclohexyl group.
[0282] In one or more embodiments, R 31 To R 34 R 35a R 35b R 36a R 36b R 37a R 37b R 38a and R 38b Each can be independently:
[0283] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano (CN), nitro, amino, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;
[0284] Each of the C1-Cs is replaced by at least one of the following: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano (CN), nitro, amino, and phenyl; or
[0285] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, or anthracene, respectively, either unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano(CN), nitro, amino, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, or combinations thereof.
[0286] In one or more embodiments, the organometallic compound represented by Formula 3 may be an organometallic compound represented by Formula 3-1 or an organometallic compound represented by Formula 3-2:
[0287] Equation 3-1
[0288]
[0289] Equation 3-2
[0290] .
[0291] In formula 3-1, the carbon atom of the imidazole group and M 31 The bond between them can be a coordinate bond. That is, the imidazole group in formula 3-1 can include bonds with M. 31 Combined carbene portion.
[0292] In formula 3-2, the carbon atom of the benzimidazole group and M 31 The bonds between them can be coordinate bonds. That is, the benzimidazole group in formula 3-2 can include bonds with M. 31 Combined carbene portion.
[0293] In equations 3-1 and 3-2,
[0294] M 31 CY 32 CY 33 CY 34 X 12 X 13 X 14 T 31 T 32 T 33 n31, n32, n33, R 32 R 33 R 34 a32, a33, and a34 can each be as described in this article, and
[0295] R 311 To R 317 Each can be as follows regarding R 31 As described.
[0296] In one or more embodiments, in formulas 3-1 and 3-2,
[0297] R 311 To R 317 Each can be independently:
[0298] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphate group or its salt;
[0299] Each of the following C1-Cs was not replaced or was replaced as follows 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, or combinations thereof;
[0300] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C6-C 60 Aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 alkylthio groups, or combinations thereof; or
[0301] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9).
[0302] In one or more embodiments, in formulas 3-1 and 3-2,
[0303] R 311 To R 317 At least one of them may include
[0304] Each of the C1-Cs that has not been substituted or has been substituted by at least one of the following: 20 Alkyl, C6-C60 Aryl, or C7-C 60 Arylalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, cumyl (isopropylphenyl), or combinations thereof.
[0305] Description of Formula 5
[0306] The organometallic compound in the first and second embodiments of the emitter layer can be an organometallic compound represented by Formula 5:
[0307] Formula 5
[0308] M 51 (L 51 ) n51 (L 52 ) n52 .
[0309] In Equation 5, M 51 It can be a transition metal.
[0310] In one or more embodiments, M 51 It can be a transition metal in the first row of the periodic table, a transition metal in the second row of the periodic table, or a transition metal in the third row of the periodic table.
[0311] In one or more embodiments, M 51 It can be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
[0312] In one or more embodiments, M 51 It can be Ir, Pt, Os, or Rh.
[0313] In one or more embodiments, M 51 It can be Ir or Os.
[0314] In Equation 5, L 51 It can be a ligand represented by Equation 5A, and L 52 It can be a ligand represented by Equation 5B:
[0315] Formula 5A Formula 5B
[0316] .
[0317] Equations 5A and 5B can each be as described in this document.
[0318] In Equation 5, n51 can be 1, 2, or 3. When n51 is 2 or greater, two or more L... 51They may be the same as or different from each other.
[0319] In Equation 5, n52 can be 0, 1, or 2. When n52 is 2, the two L... 52 They may be the same as or different from each other.
[0320] In Equation 5, the sum of n51 and n52 can be 2 or 3. For example, the sum of n51 and n52 can be 3.
[0321] In one or more embodiments, in Equation 5, i)M 51 It can be Ir, and the sum of n51 and n52 can be 3; or ii) M 51 It can be Pt, and the sum of n51 and n52 can be 2.
[0322] In one or more embodiments, in Equation 5, M 51 It can be Ir, and i) n51 can be 1 and n52 can be 2; or ii) n51 can be 2 and n52 can be 1.
[0323] In Equation 5, L 51 and L 52 But they are different from each other.
[0324] In equations 5A and 5B, Y 51 To Y 54 Each can be C or N independently. For example, Y 51 and Y 53 Each can be N, and Y 52 and Y 54 Each can be C.
[0325] In equations 5A and 5B, the ring CY 51 To CY 54 Each can be independently classified as C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.
[0326] In one or more embodiments, the ring CY in formulas 5A and 5B 51 To CY 54 Each may independently include or be i) a third ring, ii) a fourth ring, iii) a fused ring group in which two or more third rings are fused together, iv) a fused ring group in which two or more fourth rings are fused together, or v) a fused ring group in which at least one third ring is fused with at least one fourth ring.
[0327] The third ring can be a cyclopentyl group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiophene group, a borocyclopentadiene group, a phosphacyclopentadiene group, a germanium heterocyclopentadiene group, or a selenophene group. azole group, diazole group, Triazole group, thiazole group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetraazole group, or azathiophene group, and
[0328] The fourth ring can be an adamantyl group, a norbornel group, a cyclohexyl group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0329] In one or more embodiments, the ring CY in formulas 5A and 5B 51 To CY 54 Each group can independently be a cyclopentyl group, a cyclohexyl group, a cyclohexene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, 1,2,3,4-tetrahydronaphthyl group, cyclopentadienyl group, furan group, thiophene group, thiophene group, borocyclopentadienyl group, phosphacyclopentadienyl group, germanium heterocyclopentadienyl group, selenophene group, indole group, benzofuran group, benzothiophene group, benzothiophene group, benzothiophene group, benzoboron heterocyclopentadienyl group, benzophosphacyclopentadienyl group, benzogermanium heterocyclopentadienyl group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene group, dibenzoboron heterocyclopentadienyl group, dibenzophosphacyclopentadienyl group, dibenzogermanium heterocyclopentadienyl group, dibenzoselenophene group, benzofluorene group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzothiophene group, naphthobenzothiophene group The following groups are listed: pyrrole group, naphthobenzoborane heterocyclopentadienyl group, naphthobenzophosphonocyclopentadienyl group, naphthobenzogermanium heterocyclopentadienyl group, naphthobenzoselenophene group, dibenzofluorene group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthothiophene group, dinaphthothiophene group, dinaphthoborane heterocyclopentadienyl group, dinaphthogermanium heterocyclopentadienyl group, dinaphthoselenophene group, indolephene group, phenanthrenebenzofuran group, phenanthrenebenzothiophene group, phenanthrenebenzothiophene group, phenanthrenebenzothiophene group, phenanthrenebenzoborane heterocyclopentadienyl group, phenanthrenebenzophosphonocyclopentadienyl group, phenanthrenebenzogermanium heterocyclopentadienyl group, phenanthrenebenzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzothiorrole group, azabenzoborone cyclopentadiene group, azabenzophosphace ... Groups, azidobenzogermanium heterocyclopentadiene group, azidobenzoselenene group, azidobenzofluorene group, azidobenzocarbazole group, azidonaphthalenebenzofuran group, azidonaphthalenebenzothiophene group, azidonaphthalenebenzothiophene group, azidonaphthalenebenzoborone heterocyclopentadiene group, azidonaphthalenebenzophosphonone heterocyclopentadiene group, azidonaphthalenebenzogermanium heterocyclopentadiene group, azidonaphthalenebenzoselenene group, azidobenzofluorene group, azidobenzocarbazole group, azidonaphthalenebenzofuran group, azidonaphthalene Thiophene group, azidinophthirole group, azidinophorone ... Benzo[a]selenophene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, benzo[a]quinoxaline group, benzo[a]quinoxaline group, benzo[a]quinazoline group, phenanthrene group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, azirthiol group, aziborone heterocyclopentadienyl group, aziphosphonone heterocyclopentadienyl group, azigeranone heterocyclopentadienyl group, aziselenophene group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzene azole group, benzothiazole group, benzoisothiazole group, benzo[] Diazole group, benzothiadiazole group, pyridopyrrole group, pyridopyrazole group, pyridoimidazol group, pyridopyrazole group, pyridopyrazole group azole group, pyridine isopropylidene azole group, pyridothiazole group, pyridoisothiazole group, pyrido Diazole group, pyridothiadiazole group, pyrimidopyrrole group, pyrimidopyrazole group, pyrimidoimidazol group, pyrimidopyrazole group, pyrimidopyrazole group azole group, pyrimidine isocyanate azole group, pyrimidothiazol group, pyrimidoisothiazol group, pyrimido Diazole group, pyrimidothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, norbornene group, phenyl group fused with cyclohexyl group, phenyl group fused with norbornene group, pyridine group fused with cyclohexyl group, or pyridine group fused with norbornene group.
[0330] In one or more embodiments, the ring CY in formulas 5A and 5B 51 and CY 53 They may be the same as or different from each other.
[0331] In one or more embodiments, the ring CY in formulas 5A and 5B 52 and CY 54 They may be the same as or different from each other.
[0332] In one or more embodiments, the ring CY in formulas 5A and 5B 51 To CY 54 But they are different from each other.
[0333] In equations 5A and 5B, R 51 To R 54 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 51 (Q) 52 (Q) 53 -Ge(Q) 51 (Q) 52 (Q) 53 -N(Q) 54 (Q) 55 -B(Q) 56 (Q) 57 -P(=O)(Q) 58 (Q) 59 ), or -P(Q 58 (Q) 59 Q 51 To Q 59 Each can be as described in this article.
[0334] In one or more embodiments, R in formulas 5A and 5B 51 To R 54 Each can be independently:
[0335] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;
[0336] Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;
[0337] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, phenyl C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof; or
[0338] -Si(Q 51 (Q) 52 (Q) 53 -Ge(Q) 51 (Q) 52 (Q) 53 -N(Q) 54 (Q) 55 -B(Q) 56 (Q) 57 -P(=O)(Q) 58 (Q) 59 ), or -P(Q 58 (Q) 59 ),and
[0339] Q 51 To Q 59 Each can be independently:
[0340] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0341] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.
[0342] In one or more embodiments, R 51 To R 54 Each can be independently:
[0343] Hydrogen, deuterium, -F, or cyano;
[0344] C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, cyano, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 Alkyl)biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C1-C) 20 Alkyl) dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorodibenzothiophenyl, (C1-C 20 Alkyl)dibenzothiophene group, or combinations thereof;
[0345] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, phenyl, or biphenyl: deuterium, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkoxy, fluorinated C1-C 20 Alkoxy, C1-C 20 Alkylthio, deuterated C1-C 20 Alkylthio, fluorinated C1-C 20 Alkylthio, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 Alkyl)biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C1-C) 20 Alkyl) dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorodibenzothiophenyl, (C1-C 20 Alkyl) dibenzothiophene group, or combinations thereof; or
[0346] -Si(Q 51 (Q) 52 (Q) 53 ) or -Ge(Q 51 (Q) 52 (Q) 53 ).
[0347] In equations 5A and 5B, b51 to b54 represent R respectively. 51 The quantity up to R 54 The number of R values, and each can be an integer from 0 to 20 independently. When b51 is 2 or greater, two or more R values... 51 They can be the same or different from each other, and when b52 is 2 or greater, two or more R... 52 They can be the same or different from each other, and when b53 is 2 or greater, two or more Rs 53 They can be the same or different from each other, and when b54 is 2 or greater, two or more R... 54 They can be the same or different from each other. For example, b51 to b54 can each be an integer from 0 to 8 independently.
[0348] In one or more embodiments, in Formula 5A, Y 52 It can be C, Y 52 With M 51 The bonds between them can be covalent, and the number of R bonds is b52. 52 At least one of them can be cyano or -F.
[0349] In one or more embodiments, in Formula 5A, Y 51 It can be N, Y 51 With M 51 The bond between them can be a coordinate bond, CY 51 R can be an imidazole group, a triazole group, a benzimidazole group, or a triazolidine group, and the number of R is b52. 52 At least one of them can be cyano or -F.
[0350] In one or more embodiments, in Formula 5A, Y 51 It can be C, and Y 51 and M 51 The bond between them can be a coordinate bond.
[0351] In one or more embodiments, in Formula 5A, Y 51 It can be C, Y 51 and M 51 The bond between them can be a coordinate bond, and CY 51 It can be a benzimidazole group or an imidazopyrazine group.
[0352] Examples of organometallic compounds represented by formula 3 or 5
[0353] In one or more embodiments, the organometallic compound represented by formula 3 or 5 may be one of compounds P1 to P53, but the embodiments are not limited to this:
[0354]
[0355]
[0356]
[0357]
[0358]
[0359] .
[0360] Description of Equation 4
[0361] The delayed fluorescence material in the first and second embodiments of the emission layer can be a polycyclic compound represented by Formula 4:
[0362] Formula 4
[0363] .
[0364] In Equation 4,
[0365] Z can be B or N.
[0366] CY 41 To CY 43 Each can be independently classified as C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,
[0367] Y 41 Can be a single key, * -N(R 44 )- * '、 * -B(R 44 )- * '、 * -P(R 44 )- * '、 * -C(R 44 (R) 45 )- * '、 * -Si(R 44 (R) 45 )- * '、 * -Ge(R 44 (R)45 )- * '、 * -O- * '、 * -S- * '、 * -Se- * '、 * -C(=O)- * ',or * -S(=O)2- * ',
[0368] Y 42 Can be a single key, * -N(R 46 )- * '、 * -B(R 46 )- * '、 * -P(R 46 )- * '、 * -C(R 46 (R) 47 )- * '、 * -Si(R 46 (R) 47 )- * '、 * -Ge(R 46 (R) 47 )- * '、 * -O- * '、 * -S- * '、 * -Se- * '、 * -C(=O)- * ',or * -S(=O)2- * ',
[0369] Y 43 Can be a single key, * -N(R 48 )- * '、 * -B(R 48 )- * '、 * -P(R 48 )- * '、 * -C(R 48 (R) 49 )- * '、 *-Si(R 48 (R) 49 )- * '、 * -Ge(R 48 (R) 49 )- * '、 * -O- * '、 * -S- * '、 * -Se- * '、 * -C(=O)- * ',or * -S(=O)2- * ',
[0370] b41 to b43 can each be 0 or 1 independently.
[0371] When b41 is 0, Y 41 It may not exist when b42 is 0, Y 42 It may not exist, and when b43 is 0, Y 43 It may not exist.
[0372] R 41 To R 49 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),
[0373] a41 to a43 can each be an integer from 0 to 20 independently.
[0374] The quantity of R is a41 41 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10b Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10b Replacement C1-C 30 Heterocyclic groups,
[0375] The quantity of R is a42 42 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10b Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10b Replacement C1-C 30 Heterocyclic groups,
[0376] The quantity of R is a43 43 Two or more may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10b Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10b Replacement C1-C 30 Heterocyclic groups,
[0377] R 41 To R 49 Two or more adjacent elements may optionally be combined with each other to form an unsubstituted or at least R 10b Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10b Replacement C1-C 30 Heterocyclic groups,
[0378] R 10b For example, regarding R 41As described,
[0379] * and *' Each represents a binding site with an adjacent atom.
[0380] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can each independently be:
[0381] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;
[0382] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof;
[0383] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;
[0384] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q)37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or
[0385] Its combination, and
[0386] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0387] In one or more embodiments, the ring CY 41 To CY 43 Each can be independently i) a phenyl group, or ii) two or more of them C3-C30 A polycyclic cyclic group in which cyclic groups are fused together. The two C3-C atoms in the polycyclic cyclic group... 30 Cyclic groups can fuse together while sharing boron (B) or nitrogen (N).
[0388] In one or more embodiments, at least one of b41 to b43, or at least two of b41 to b43, may each be 1. In one or more embodiments, two of b41 to b43 may each be 1, and the remaining one of b41 to b43 may be 0.
[0389] In one or more embodiments, R 41 To R 49 Each can be independently:
[0390] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano (CN), nitro, amino, C1-C 60 Alkyl, C1-C 60 alkoxy, or C1-C 60 Alkylthio;
[0391] Each of the C1-Cs is replaced by at least one of the following: 60 Alkyl, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano (CN), nitro, amino, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, and base; or
[0392] Each of the following is either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano (CN), nitro, amino, C1-C60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, or combinations thereof.
[0393] In one or more embodiments, the polycyclic compound represented by Formula 4 may be a polycyclic compound represented by any one of Formulas 4-1 to 4-9:
[0394] Equation 4-1
[0395]
[0396] Equation 4-2
[0397]
[0398] Equation 4-3
[0399]
[0400] Equation 4-4
[0401]
[0402] Formula 4-5
[0403]
[0404] Equation 4-6
[0405]
[0406] Equation 4-7
[0407]
[0408] Equation 4-8
[0409]
[0410] Equation 4-9
[0411] .
[0412] In equations 4-1 to 4-9,
[0413] Z1 to Z3 can each be as described with respect to Z.
[0414] Y 41 and Y 42 Each can be as described in this article,
[0415] Y 44 To Y 47 Each can be as follows regarding Y 41 and Y 42 As described,
[0416] R 411 For example, regarding R 41 As described, R 421 For example, regarding R 42 As described, R 431 and R 432 Each can be as follows regarding R 43 As described, R 441 For example, regarding R 41 As described, R 451 For example, regarding R 42 As described, and R 461 For example, regarding R 43 As described,
[0417] a411 can be an integer from 0 to 4.
[0418] a421 can be an integer from 0 to 3.
[0419] a431 can be an integer from 0 to 4.
[0420] a441 can be an integer from 0 to 4.
[0421] a451 can be an integer from 0 to 3, and
[0422] a461 can be an integer from 0 to 3.
[0423] Examples of polycyclic compounds represented by Equation 4
[0424] The polycyclic compound represented by Formula 4 can be one of compounds D1 to D30, but the implementation is not limited to this:
[0425]
[0426]
[0427]
[0428]
[0429] .
[0430] Figure 1 Description
[0431] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments, which is an example of a light-emitting device according to one or more embodiments. Hereinafter, reference will be made to... Figure 1 The structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments are described in further detail.
[0432] refer to Figure 1 The organic light-emitting device 10 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an intermediate layer 10A disposed between the first electrode 11 and the second electrode 19.
[0433] The intermediate layer 10A includes an emitter layer 15 and may further include a hole transport region 12 disposed between the first electrode 11 and the emitter layer 15, and an electron transport region 17 disposed between the emitter layer 15 and the second electrode 19.
[0434] A substrate may be disposed below the first electrode 11 or on the second electrode 19. The substrate may be any suitable substrate for organic light-emitting devices, such as a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.
[0435] First electrode 11
[0436] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 may include a material with a high work function to facilitate hole injection.
[0437] The first electrode 11 may be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, the material used to form the first electrode 11 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or combinations thereof. In one or more embodiments, when the first electrode 11 is a semi-transparent semi-reflective electrode or a reflective electrode, the material used to form the first electrode 11 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or combinations thereof.
[0438] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers.
[0439] Launch layer 15
[0440] The thickness of the emitting layer 15 can be from about 100 Å to about 1,000 Å, for example from about 200 Å to about 600 Å. When the thickness of the emitting layer is within the range described above, excellent light emission characteristics can be obtained without a significant increase in driving voltage.
[0441] In one or more embodiments, the emission layer 15 may include at least one fused-ring compound represented by Formula 1 as described herein. The emission layer 15 may have a configuration according to a first embodiment or a second embodiment of the emission layer as described herein.
[0442] In addition to the fused-ring compound represented by Formula 1 as described herein, the sensitizer, and the emitter, the emitter layer 15 may further include a host as described herein.
[0443] Hole transport region 12
[0444] The hole transport region 12 can be arranged between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.
[0445] The hole transport region 12 may have a single-layer structure or a multi-layer structure.
[0446] In one or more embodiments, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer / hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer structure, a hole transport layer / buffer layer structure, a hole injection layer / hole transport layer / buffer layer structure, a hole transport layer / electron blocking layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure.
[0447] Hole transport region 12 may include any compound having hole transport properties.
[0448] In one or more embodiments, the hole transport region 12 may include an amine-containing compound.
[0449] In one or more embodiments, the hole transport region 12 may include at least one of the following: 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidene bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonylstyrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonylstyrene) (PANI / PSS), compounds represented by any one of formulas 201 to 205, or combinations thereof, but the embodiments are not limited thereto:
[0450]
[0451]
[0452] Formula 201
[0453]
[0454] Formula 202
[0455]
[0456] Formula 203
[0457]
[0458] Formula 204
[0459]
[0460] Formula 205
[0461] .
[0462] In equations 201 to 205,
[0463] L 201 To L 209 Each can be independently * -O- *' , * -S- *' C5-C, substituted or unsubstituted 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 Heterocyclic groups,
[0464] xa1 to xa9 can each be an integer from 0 to 5 independently, and
[0465] R 201 To R 206 Each can be independently 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein R 201 To R 206 The two adjacent groups may optionally be connected to each other via a single bond, a dimethyl-methylene bond, or a diphenyl-methylene bond.
[0466] In one or more embodiments,
[0467] L 201 To L 209 Each can independently be an unsubstituted or substituted phenyl group, heptadene group, indene group, naphthyl group, Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Group, tetraphenyl group, Groups, Groups, pentaphenyl, hexaphenyl, pentaphenyl, rutin, halophenyl, ovoid, pyrrole, isoindole, indole, furan, thiophene, benzofuran, benzothiophene, benzocarbazole, dibenzocarbazole, dibenzofuran, dibenzothiophene, dibenzothiophene sulfone, carbazole, dibenzothiorrole, indole-carbazole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, or triindole-phenyl: deuterium, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, phenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, dibenzothiophene, benzo[9,10]phenanthryl, biphenyl, terphenyl, tetraphenyl, -Si(Q 11 (Q) 12 (Q) 13 ), or a combination thereof,
[0468] xa1 to xa9 can each be 0, 1, or 2 independently.
[0469] R 201 To R 206 Each can be independently an unsubstituted or substituted phenyl, biphenyl, terphenyl, cyclopentadienyl, indenyl, naphthyl, alkyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, alkyl, tetraphenyl, base, alkyl, pentofenyl, hexaphenyl, pentaphenyl, rubidyl, halophenyl, ovoleyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, pyridyl, indobenzocarbazoleyl, benzofuranocarbazoleyl, or benzothiophenocarbazoleyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, cyclopentadienyl, indenyl, naphthyl, alkyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, alkyl, tetraphenyl, base, alkyl, pentofenyl, hexaphenyl, pentaphenyl, rubidyl, halophenyl, ovoleyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ), or combinations thereof, and
[0470] Q 11 To Q 13 and Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0471] In one or more embodiments, the hole transport region 12 may include an amine-containing compound containing carbazole.
[0472] In one or more embodiments, the hole transport region 12 may include an amine-containing compound containing carbazole and an amine-containing compound not containing carbazole.
[0473] The carbazole-containing amine compound may include, for example, a compound represented by formula 201 that includes at least one of a carbazole group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirodifluorene group, an indobenzocarbazole group, an indobenzocarbazole group, a benzofuran-carbazole group, or a benzothiophene-carbazole group.
[0474] The amine-containing compound that does not contain carbazole may include, for example, a compound represented by formula 201 that does not contain a carbazole group and includes at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirodifluorene group, an indobenzocarbazole group, an indobenzocarbazole group, a benzofuran-carbazole group, or a benzothiophene-carbazole group.
[0475] In one or more embodiments, the hole transport region 12 may include a compound represented by formula 201, a compound represented by formula 202, or a combination thereof.
[0476] In one or more embodiments, the hole transport region 12 may include a compound represented by formula 201-1, 202-1, or 201-2, or a combination thereof:
[0477] Formula 201-1
[0478]
[0479] Formula 202-1
[0480]
[0481] Formula 201-2
[0482] .
[0483] In equations 201-1, 202-1, and 201-2, L 201 To L 203 L 205 xa1 to xa3, xa5, R 201 and R 202 Each can be as described in this article, and R 211 To R 213 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spirodifluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[9,10]phenanthryl, thiopheneyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, or pyridyl.
[0484] In one or more embodiments, the hole transport region 12 (e.g., the hole injection layer and / or hole transport layer in the hole transport region 12) may include one of compounds HT1 to HT39, or a combination thereof, but the embodiments are not limited thereto:
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491] .
[0492] In one or more embodiments, the hole transport region 12 of the organic light-emitting device 10 (e.g., a hole injection layer and / or a hole transport layer) may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (e.g., at least one of the compounds represented by formulas 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.
[0493] In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant may be -3.5 electron volts (eV) or less.
[0494] p-dopers may include quinone derivatives, metal oxides, cyano-containing compounds, or combinations thereof.
[0495] In one or more embodiments, the p-doper may include:
[0496] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ), or F6-TCNNQ;
[0497] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0498] 1,4,5,8,9,12-Hexaazabenzo[9,10]phenanthrene-hexacarbamate (HAT-CN);
[0499] Compounds represented by formula 221; or
[0500] Its combinations, but the implementation methods are not limited to this:
[0501]
[0502] Equation 221
[0503] .
[0504] In Equation 221,
[0505] R 221 To R223 Each can be independently substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein R 221 To R 223 At least one substituent may be independently:
[0506] Cyano; -F; -Cl; -Br; -I; -SF5; C1-C substituted with -F 20 Alkyl; C1-C substituted with -Cl 20 Alkyl; C1-C substituted with -Br 20 Alkyl; C1-C substituted with -I 20 Alkyl groups; or combinations thereof.
[0507] Compounds represented by formula 221 may include, for example, compound HT-D2:
[0508] .
[0509] The thickness of the hole transport region 12 can be from about 100 Å to about 10,000 Å, for example from about 400 Å to about 2,000 Å, and the thickness of the emitter layer 15 can be from about 100 Å to about 3,000 Å, for example from about 300 Å to about 1,000 Å. When the thicknesses of the hole transport region 12 and the emitter layer 15 are within the ranges described above, satisfactory hole transport characteristics and / or light emission characteristics can be obtained without a significant increase in driving voltage.
[0510] The hole transport region 12 may further include a buffer layer.
[0511] The buffer layer can compensate for the optical resonant distance according to the wavelength of the light emitted from the emission layer 15 to improve efficiency.
[0512] Hole transport region 12 may further include an electron blocking layer. The electron blocking layer may comprise any suitable material, such as at least one of 1,3-bis(N-carbazolyl)benzene (mCP) or 2,8-bis(diphenylphosphine oxide)dibenzofuran (DBFPO), but embodiments are not limited thereto.
[0513] .
[0514] Electronic transmission area 17
[0515] The electron transport region 17 is arranged between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.
[0516] The electron transport region 17 may have a single-layer structure or a multi-layer structure.
[0517] In one or more embodiments, the electron transport region 17 may have an electron transport layer structure, an electron transport layer / electron injection layer structure, a buffer layer / electron transport layer structure, a hole blocking layer / electron transport layer structure, a buffer layer / electron transport layer / electron injection layer structure, or a hole blocking layer / electron transport layer / electron injection layer structure. The electron transport region 17 may further include an electron control layer.
[0518] The electron transport region 17 may include known electron transport materials.
[0519] The electron transport region 17 (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 comprising at least one C1-C compound containing a nitrogen-deficient nitrogen. 60 Cyclic groups. C1-C groups containing nitrogen lacking π electrons. 60 Cyclic groups can be as described herein.
[0520] In one or more embodiments, the electron transport region 17 may include a compound represented by formula 601:
[0521] Formula 601
[0522] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0523] In Equation 601,
[0524] Ar 601 and L 601 Each can be independently of being unreplaced or by at least one R. 601a Replacement C5-C 60 The carbocyclic group is either unsubstituted or replaced by at least one R 601a Replacement C1-C 60 Heterocyclic groups,
[0525] xe11 can be 1, 2, or 3.
[0526] xe1 can be an integer from 0 to 5.
[0527] R 601 and R 601a Each can be independently 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, 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 ), or -P(=O)(Q 601 (Q) 602 ),
[0528] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl, and
[0529] xe21 can be an integer from 1 to 5.
[0530] In one or more embodiments, the quantity of Ar is xe11 601 and R with a quantity of xe21 601 At least one of them may include C1-C containing nitrogen lacking π electrons. 60 Cyclic groups.
[0531] In one or more embodiments, Ar in Formula 601 601 and L 601Each can independently be an unsubstituted or substituted phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Group, tetraphenyl group, Groups, Groups, pentylenetetrazol group, indene-anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, azole group, iso- Azolium group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, benzisothiazole group, benzo[a] azole group, benzene azole group, triazole group, tetraazole group Diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, or azacarbazole group: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ), or combinations thereof, and
[0532] Q 31 To Q 33 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0533] 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.
[0534] In one or more embodiments, Ar in Formula 601601 It can be an anthracene group.
[0535] In one or more embodiments, the compound represented by formula 601 may be represented by formula 601-1:
[0536] Formula 601-1
[0537] .
[0538] In Equation 601-1,
[0539] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), and X 616 It can be N or C(R) 616 ), where X 614 To X 616 At least one of them can be N.
[0540] L 611 To L 613 Each can be independent, such as regarding L. 601 As described,
[0541] xe611 to xe613 can each be independent as described with respect to xe1.
[0542] R 611 To R 613 They can be discussed independently, such as regarding R. 601 As described, and
[0543] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0544] In one or more embodiments, xe1 and xe611 to xe613 in formulas 601 and 601-1 may each be 0, 1 or 2 independently.
[0545] In one or more embodiments, R in formulas 601 and 601-1 601 and R 611 To R 613 Each can be independently:
[0546] Each of the following is not substituted or is substituted with: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, base, alkyl, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso azole group, thiadiazole group, Diazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, or azacarbazoyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, base, alkyl, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso azole group, thiadiazole group, Diazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, or combinations thereof; or
[0547] -S(=O)2(Q 601 ) or -P(=O)(Q 601 (Q) 602 ),and
[0548] Q 601 and Q 602 Each can be as described in this article.
[0549] Electron transport region 17 (e.g., electron transport layer in electron transport region 17) may include one of compounds ET1 to ET36, or a combination thereof, but the implementation is not limited thereto:
[0550]
[0551]
[0552]
[0553]
[0554]
[0555]
[0556]
[0557]
[0558]
[0559]
[0560]
[0561] .
[0562] In one or more embodiments, the electron transport region 17 may include at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), DBFPO, or combinations thereof, but the embodiments are not limited thereto. For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include BCP or Bphen:
[0563]
[0564] .
[0565] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can each be independently from about 20 Å to about 1,000 Å, for example from about 30 Å to about 300 Å. When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within the ranges described above, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without a significant increase in driving voltage.
[0566] 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 range described above, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.
[0567] In addition to the materials described above, the electron transport region 17 (e.g., the electron transport layer in the electron transport region 17) may further include a metallic material.
[0568] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or combinations thereof. The metal ions of alkali metal complexes may include Li ions, Na ions, K ions, Rb ions, Cs ions, or combinations thereof, and the metal ions of alkaline earth metal complexes may include Be ions, Mg ions, Ca ions, Sr ions, Ba ions, or combinations thereof. The ligands coordinating with the metal ions in alkali metal complexes or alkaline earth metal complexes may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, and hydroxyphenyl. azole, hydroxyphenylthiazolium, hydroxydiphenyl Diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazolazole, bipyridine, phenanthroline, cyclopentadiene, or combinations thereof.
[0569] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, at least one of compounds ET-D1 (LiQ) or ET-D2, but the embodiments are not limited thereto.
[0570] .
[0571] The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may be in direct contact with the second electrode 19.
[0572] The electron injection layer may have i) a monolayer structure consisting of a single layer made of a single material, ii) a monolayer structure consisting of a single layer comprising a variety of different materials, or iii) a multilayer structure comprising multiple layers comprising a variety of different materials.
[0573] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
[0574] The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. In one or more embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs.
[0575] The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof.
[0576] The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a combination thereof.
[0577] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal; or a combination thereof.
[0578] The alkali metal compound may include alkali metal oxides such as Li2O, Cs2O, K2O, or a combination thereof; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or a combination thereof; or a combination thereof. In one or more embodiments, the alkali metal compound may include LiF, Li2O, NaF, LiI, NaI, CsI, KI, or a combination thereof.
[0579] The alkaline earth metal compound may include alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1), Ba x Ca 1-x O (where 0 < x < 1), or a combination thereof. In one or more embodiments, the alkaline earth metal compound may include BaO, SrO, CaO, or a combination thereof.
[0580] The rare earth metal compound may include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, TbF3, or a combination thereof. In one or more embodiments, the rare earth metal compound may include YbF3, ScF3, TbF3, YbI3, ScI3, TbI3, or a combination thereof.
[0581] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include ions of alkali metals, alkaline earth metals, and rare earth metals as described above, and the ligands of the alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes that coordinate with the metal ions may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, and hydroxyphenyl. azole, hydroxyphenylthiazolium, hydroxydiphenyl Diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazolazole, bipyridine, phenanthroline, cyclopentadiene, or combinations thereof.
[0582] The electron injection layer may be composed of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations 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 the matrix comprising the organic materials.
[0583] The thickness of the electron injection layer can be from about 1 Å to about 100 Å, and for example from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.
[0584] Second electrode 19
[0585] The second electrode 19 is disposed on the intermediate layer 10A. The second electrode 19 may be a cathode serving as an electron injection electrode, and in this respect, the material used to form the second electrode 19 may be a metal, alloy, conductive compound, or a combination thereof having a relatively low work function.
[0586] The second electrode 19 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, IZO, or combinations thereof. The second electrode 19 may be a transmissive electrode, a semi-transmissive and semi-reflective electrode, or a reflective electrode.
[0587] The second electrode 19 may have a single-layer structure having a single layer or a multi-layer structure including two or more layers.
[0588] As used in this article, the term "C1-C" 60"Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1 to 60 carbon atoms, and as used herein, "C1-C..." 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.
[0589] In this article, C1-C 60 Alkyl groups can be C1-C 20 Alkyl groups, such as C1-C 10 Alkyl or C1-C6 alkyl. These alkyl groups can each be straight-chain or branched. In the case of branched alkyl groups, the lower limit of the carbon number range for each alkyl group becomes 3. C1-C 60 Alkyl, C1-C 20 Alkyl and / or C1-C 10 Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel. Sec-decyl, tert-decyl, etc.: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or combinations thereof.
[0590] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 It is C1-C 60 The monovalent group is represented by alkyl, and non-limiting examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.
[0591] As used in this article, the term "C1-C" 60 "Alkylthio" refers to the group consisting of -SA 101’ (where A) 101’ It is C1-C 60 Alkyl groups are monovalent groups.
[0592] As used in this article, the term "C2-C" 60 "Alkenyl" refers to a group formed by the synthesis of alkenyl groups from C2-C2. 60A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, and non-limiting examples include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.
[0593] As used in this article, the term "C2-C" 60 "Alkyne group" refers to a group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and non-limiting examples include ethynyl, propynyl, etc. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to a group that has a similar structure to C2-C2. 60 Divalent groups with the same structure as alkynyl groups.
[0594] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms, and as used herein by the term "C3-C". 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.
[0595] C3-C 10 Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norcamphenyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, etc.
[0596] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms, and as used herein by the term "C1-C". 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0597] C1-C 10 Non-limiting examples of heterocyclic alkyl groups include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, etc.
[0598] As used in this article, the term "C3-C" 10"Cycloalkenyl" refers to a monovalent hydrocarbon cyclic group that includes 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and is not aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a C3-C... 10 A divalent group with the same structure as a cycloalkenyl group.
[0599] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom, 1 to 10 carbon atoms as cyclic atoms, and at least one double bond, and is not aromatic. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl, 2,3-dihydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0600] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, Base, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.
[0601] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent cyclic group comprising a heterocyclic aromatic ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms, and as used herein by the term "C1-C". 60 "Hypo-heteroaryl" refers to a divalent group comprising a heterocyclic aromatic ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C... 60heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.
[0602] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 It is C6-C 60 Aryl), and as used herein, the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 It is C6-C 60 Aryl).
[0603] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, having only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, and lacking aromaticity in its overall structure. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include fluorene groups, etc. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0604] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings, having heteroatoms selected from N, O, P, Si, S, Se, Ge, and B as cyclic atoms in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and not being aromatic in its overall structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups include the carbazole group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.
[0605] As used in this article, "C1-C containing π-electron-deficient nitrogen" 60 "Cyclic group" refers to a group having 1 to 60 carbon atoms and including at least one cyclic group. * -N= *' (in * and *' Each group represents a binding site with an adjacent atom, forming a cyclic group that is part of the ring. For example, a C1-C ring containing nitrogen that is π-electron deficient. 60 The cyclic group may be a) a first ring, b) a fused ring group in which two or more first rings are fused together, or c) a fused ring group in which at least one first ring is fused with at least one second ring.
[0606] As used in this article, “π-electron-rich C3-C” 60"Cyclic group" refers to a group having 3 to 60 carbon atoms and not containing any cyclic groups. * -N= *' (in * and *' Each group represents a binding site with an adjacent atom, forming a cyclic group as the ring moiety. For example, the π-electron-rich C3-C... 60 The cyclic group can be a) a second ring or b) a fused ring group in which two or more second rings are fused together.
[0607] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, and may be, for example, a) a third ring or b) a fused ring group in which two or more third rings are fused together.
[0608] As used in this article, the term "C1-C" 60 A "heterocyclic group" refers to a monocyclic or polycyclic group having 1 to 60 carbon atoms and, in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom, and may be, for example, a) a fourth ring, b) a fused ring group in which two or more fourth rings are fused together, or c) a fused ring group in which at least one third ring is fused with at least one fourth ring.
[0609] As used in this article, "first ring" can be an imidazole group, a pyrazole group, a thiazole group, or an isothiazole group. azole group, iso- azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, triazole group, tetrazolium group, Diazole group, triazine group, or thiadiazole group.
[0610] As used in this article, "second ring" can be a phenyl group, a cyclopentadienyl group, a pyrrole group, a furan group, a thiophene group, or a thiophene group.
[0611] As used herein, "third ring" can be a cyclopentyl group, a cyclopentadienyl group, an indene group, an adamantyl group, a norbornene group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (norbornene group), a bicyclo[2.2.2]octyl group, a cyclohexyl group, a cyclohexene group, or a phenyl group.
[0612] As used in this article, the "fourth ring" can be a furan group, a thiophene group, a pyrrole group, or a thiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, triazathiophene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.
[0613] For example, C1-C containing nitrogen lacking π electrons. 60 The cyclic group can be an imidazole group, a pyrazole group, a thiazole group, or an isothiazole group. azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, phthalazine group, naphthidine group, quinoxaline group, benzo[a]quinoxaline group, quinazolinine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, benzisothiazole group, benzo[a] azole group, benzene azole group, triazole group, tetraazole group Diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzothiophene group, pyridopyrazine group, etc.
[0614] For example, π-electron-rich C3-C 60 The cyclic group can be a phenyl group, a heptadene group, an indene group, a naphthyl group, etc. Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Group, tetraphenyl group, Groups, Groups, including pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidium group, halophenyl group, ovalphenyl group, pyrrole group, furan group, thiophene group, isoindole group, indole group, indene group, benzofuran group, benzothiophene group, benzothiorrole group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthothiorrole group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, carbazole group, dibenzothiorrole group, indolecarbazole group, benzofuran-carbazole group, benzothiophene group, benzothiorrolecarbazole group, triindolephenyl group, pyrrolophenanthrene group, furan-phenanthrene group, thiophenanthrene group, benzonaphthuran group, benzonaphthiophene group, indolephenanthrene group, benzofuran-phenanthrene group, benzothiophenanthrene group, etc.
[0615] For example, C5-C 60 The carbocyclic group can be a cyclopentyl group, a cyclohexyl group, a cyclohexene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, 1,2,3,4-tetrahydronaphthyl group, cyclopentadienyl group, indene group, fluorene group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, etc.
[0616] For example, C1-C 60Heterocyclic groups can be thiophene groups, furan groups, pyrrole groups, cyclopentadienyl groups, thiophene groups, borocyclopentadienyl groups, phosphacyclopentadienyl groups, selenophene groups, germanium heterocyclopentadienyl groups, benzothiophene groups, benzofuran groups, indole groups, benzothiophene groups, benzoboron heterocyclopentadienyl groups, benzophosphacyclopentadienyl groups, benzoselenophene groups, benzogermanium heterocyclopentadienyl groups, dibenzothiophene groups, dibenzofuran groups, carbazole groups, dibenzothiophene groups, dibenzoboron heterocyclopentadienyl groups, dibenzophosphacyclopentadienyl groups, dibenzoselenophene groups, dibenzogermanium heterocyclopentadienyl groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-dioxide groups, azabenzothiophene groups, azabenzofuran groups, azaindole groups, and aza... Indene group, azirbenzothiophene group, azirbenzoboranecyclopentadiene group, azirbenzophosphacyclopentadiene group, azirbenzoselenophene group, azirbenzogeranecyclopentadiene group, azirdibenzothiophene group, azirdibenzofuran group, azircarbazole group, azirfluorene group, azirdibenzothiophene group, azirdibenzoboranecyclopentadiene group, azirdibenzophosphacyclopentadiene group, azirdibenzoselenophene group, azirdibenzogeranecyclopentadiene group, azirdibenzothiophene 5-oxide group, azir-9H-fluorene-9-one group, azirdibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] Diazole group, benzothiadiazole group, etc.
[0617] As used in this article, "C1-C containing π-electron-deficient nitrogen" 60 "Cyclic groups", "π-electron-rich C3-C" 60 Cyclic groups, C5-C 60 "Carbon ring group" and "C1-C" 60 "Heterocyclic groups" refer to a portion of a fused ring or, depending on the formula, a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group.
[0618] Substituted C1-C containing π-electron-deficient nitrogen 60 Cyclic groups, substituted C3-C electron-rich groups 60 Cyclic groups, substituted C5-C 60 Carbocyclic groups, substituted C1-C 60Heterocyclic groups, substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkylene, substituted C2-C 60 alkenyl, substituted C2-C 60 Ethyne-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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 The substituents of heteroarylsulfonyl groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups can each be independently:
[0619] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;
[0620] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof;
[0621] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;
[0622] -Si(Q 31 (Q) 32 (Q) 33-Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or
[0623] Its combination.
[0624] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0625] In some implementations, Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each can be independently:
[0626] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0627] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.
[0628] As used in this article, the term "room temperature" refers to a temperature of approximately 25°C.
[0629] As used herein, the terms "biphenyl," "triphenyl," and "tetraphenyl" refer to monovalent groups in which two, three, or four phenyl groups are linked together by single bonds, respectively. As used herein, the term "(C1-C... 20 (alkyl)X group (e.g., (C1-C) 20 Alkyl)phenyl) refers to a compound formed by at least one C1-C 20 Alkyl-substituted X group (e.g., phenyl). Other similar terms can be understood in a similar manner.
[0630] Hereinafter, compounds and organic light-emitting devices according to exemplary embodiments are described in detail with reference to synthesis examples and embodiments. However, the embodiments are not limited thereto. The phrase "using 'B' instead of 'A'" used in describing synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used, in molar equivalents.
[0631] Example
[0632] Synthesis Example 1: Synthesis of Compound 6
[0633]
[0634] Synthesis of compound S1
[0635] 1,5-Dibromo-2,4-difluorobenzene (2.0 g, 7.36 mmol), 3,6-di-tert-butyl-9H-carbazole (4.5 g, 16.19 mmol), and cesium carbonate (7.2 g, 22.08 mmol) were mixed with 35 mL of dimethylformamide (DMF) and stirred under reflux for 24 hours. The temperature was then lowered to room temperature. Water was added to the resulting mixture, followed by washing with dichloromethane. The organic layer was extracted from the mixture, separated, and the solvent was removed under reduced pressure. The resulting solid was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 4.7 g (81% yield) of compound S1. The obtained compound was confirmed by high-resolution mass spectrometry (HRMS) and HPLC using matrix-assisted laser desorption / ionization (MALDI).
[0636] HRMS (MALDI): For C 46 H 50 Calculated value of Br2N2: m / z 788.2341, measured value: 788.2340.
[0637] Synthesis of compound 5A
[0638] Compound S1 (1.8 g, 2.28 mmol) was mixed with 40 mL of tetrahydrofuran (THF), and then the temperature was lowered to -78 °C. Then, n-butyllithium (2.5 M, in hexane) (2 mL, 5 mmol) was slowly added. After stirring the mixture at the same temperature for another 2 hours, [the following text is missing: "..."] Tonoxyphenone (1.1 g, 5.70 mmol) and 10 mL of tetrahydrofuran were mixed together and then slowly added to the mixture. The resulting mixture was stirred at room temperature for 18 hours, neutralized with dilute hydrochloric acid, and then washed with dichloromethane. The organic layer was extracted from the mixture, separated, and the solvent was removed under reduced pressure. The resulting solid was combined again with dichloromethane (DCM). Then, boron trifluoride-diethyl ether complex (BF3OEt2) (0.4 mL, 3.42 mmol) was slowly added to the mixture, followed by stirring for 12 hours. Water was added to the resulting mixture, and the mixture was washed with dichloromethane. The solvent was removed from the organic layer extracted from the mixture under reduced pressure, and the resulting solid was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 1.1 g (49% yield) of compound 5A. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
[0639] HRMS (MALDI): For C 72 H 64Calculated value of N2O2: m / z 988.4968, measured value: 988.4968.
[0640] Synthesis of compound 5B
[0641] Compound 5A (1.1 g, 1.11 mmol) was mixed with 30 mL of dichloromethane, and the temperature was lowered to 0 °C while shielding the light with aluminum foil. N-bromosuccinimide (NBS) (0.2 g, 1.33 mmol) was then slowly added. After stirring the mixture at room temperature for 14 hours, water was added, followed by washing with dichloromethane. The organic layer was extracted from the mixture, separated, and the solvent was removed under reduced pressure. The resulting solid was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 0.7 g (60% yield) of compound 5B. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
[0642] HRMS (MALDI): For C 72 H 63 Calculated value of BrN2O2: m / z 1066.4073, measured value: 1066.4075.
[0643] Synthesis of Compound 5
[0644] Compound 5A (1.6 g, 1.50 mmol) was mixed with 70 mL of tert-butylbenzene ( t The mixture was mixed with boron trifluoride (B2Ph) and then the temperature was lowered to -78°C. 2.5 M butyllithium (in hexane) (0.9 mL, 2.25 mmol) was slowly added to the resulting mixture, followed by stirring at the same temperature for another 2 hours. 1 M boron tribromide (4.5 mL, 4.5 mmol) in dichloromethane was slowly added, followed by stirring at room temperature for 18 hours. Then, N,N-diisopropylethylamine (DIPEA) (0.8 mL, 4.5 mmol) was slowly added at 0°C, followed by stirring at 130°C under reflux for 4 hours. Water was added to the resulting mixture, followed by washing with dichloromethane. The organic layer was extracted from the mixture, separated, and the solvent was removed under reduced pressure. The resulting solid was combined with dichloromethane again. Then, a boron trifluoride-diethyl ether complex (0.4 mL, 3.42 mmol) was slowly added, followed by stirring for 12 hours. Water was added to the resulting mixture, followed by washing with dichloromethane. The organic layer was extracted from the mixture, separated, and the solvent was removed under reduced pressure. The resulting solid was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 0.48 g (32% yield) of compound 5. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
[0645] HRMS (MALDI): For C 72 H 61 Calculated value of BN2O2: m / z 996.4826, measured value: 996.4825.
[0646] Synthesis Example 2: Synthesis of Compound 11
[0647]
[0648] Synthesis of Compound 11
[0649] Compound 11 was obtained in 0.59 g (28% yield) in the same manner as compound 5 used in synthetic Example 1, except that 3,6-bis(2,6-diisopropylphenyl)-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
[0650] HRMS (MALDI): For C 104 H 93 Calculated value of BN2O2: m / z 1412.7330, measured value: 1412.7331.
[0651] Synthesis Example 3: Synthesis of Compound 23
[0652]
[0653] Synthesis of Compound 23
[0654] Compound 23 was obtained in the same manner as that used to obtain compound 5 in synthetic Example 1, except that 10,10-dimethylanthracene-9(10H)-one was used instead of Tonketones were obtained. The compounds were confirmed by HRMS (MALDI) and HPLC analysis.
[0655] HRMS (MALDI): For C 78 H 73 Calculated value of BN2: m / z 1048.5867, measured value: 1048.5866.
[0656] Synthesis Example 4: Synthesis of Compound 29
[0657]
[0658] Synthesis of Compound 29
[0659] Compound 29 was obtained in the same manner as that used to obtain compound 5 in synthetic Example 1, except that 3,6-bis(2,6-diisopropylphenyl)-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole, and 10,10-dimethylanthracene-9(10H)-one was used instead of Tonketones were obtained. The compounds were confirmed by HRMS (MALDI) and HPLC analysis.
[0660] HRMS (MALDI): For C 110 H 105 Calculated value of BN2: m / z 1464.8371, measured value: 1464.8371.
[0661] Example 1
[0662] ITO (as anode) patterned glass substrates are cut to dimensions of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropanol and deionized (DI) water for 5 minutes each, cleaned by UV irradiation and exposure to ozone for 30 minutes, and then loaded onto a vacuum deposition apparatus.
[0663] Compound HT1 and F12-P-dopant were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and compound HT1 was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of 1,650 Å.
[0664] Next, a premixed mixture of compounds HTH3 and ETH8, defined as the main body, in a weight ratio of 50:50, is vacuum co-deposited with compound 5 (dopant) in a weight ratio of 99:1 on the hole transport layer to form an emitter layer with a thickness of 400 Å.
[0665] Then, compound ET27 and Liq-N-dopant were vacuum co-deposited on the emitter layer at a volume ratio of 50:50 to form an electron transport layer with a thickness of 350 Å. Liq-N-dopant was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al was vacuum deposited on the electron injection layer to form a cathode with a thickness of 1,000 Å, thereby completing the fabrication of the light-emitting device.
[0666]
[0667] Examples 2 to 4 and Comparative Examples 1 and 2
[0668] The light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emission layer, the compounds shown in Table 1 were used instead of compound 5 for use as dopants.
[0669] Example 5
[0670] ITO (as anode) patterned glass substrates are cut to dimensions of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropanol and DI water for 5 minutes each, cleaned by UV irradiation and exposure to ozone for 30 minutes, and then loaded onto a vacuum deposition apparatus.
[0671] Compound HT1 and F12-P-dopant were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and compound HT1 was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of 1,650 Å.
[0672] Next, a premixed mixture of compounds HTH3 and ETH8, defined as the main body, containing compounds in a weight ratio of 50:50, was vacuum co-deposited with compounds P53 (sensitizer) and 5 (dopant) in a weight ratio of 92:7:1 on the hole transport layer to form an emitter layer with a thickness of 400 Å.
[0673] Then, compound ET27 and Liq-N-dopant were vacuum co-deposited on the emitter layer at a volume ratio of 50:50 to form an electron transport layer with a thickness of 350 Å. Liq-N-dopant was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al was vacuum deposited on the electron injection layer to form a cathode with a thickness of 1,000 Å, thereby completing the fabrication of the light-emitting device.
[0674]
[0675] Examples 6 to 8 and Comparative Examples 3 to 5
[0676] The light-emitting device was manufactured in the same manner as in Example 5, except that, when forming the emission layer, the compounds shown in Table 2 were used instead of compound 5 for use as dopants.
[0677] Evaluation of the embodiments. Evaluation of the characteristics of the light-emitting device.
[0678] For each of the light-emitting devices fabricated in Examples 1 to 8 and Comparative Examples 1 to 5, the driving voltage (V), maximum external quantum efficiency (Max EQE, %), and maximum emission wavelength (λ) of the emission peak in the emission spectrum were evaluated. maxThe values of λ (nm) and FWHM (nm), and the roll-off ratio (%) are shown in Tables 1 and 2. A current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. The roll-off ratio was calculated according to Equation 1.
[0679] Equation 1
[0680] Roll-off ratio = {1 - (luminous efficacy (at 6,000 nits) / maximum luminous efficacy)} × 100%
[0681] Table 1
[0682]
[0683] Table 2
[0684]
[0685]
[0686]
[0687] As confirmed by Table 1, the light-emitting devices of Examples 1 to 4 emit green light and have excellent characteristics in terms of driving voltage, maximum external quantum efficiency, FWHM, and roll-off ratio.
[0688] As confirmed by Table 1, the light-emitting devices of Examples 1 to 4 have improved characteristics in terms of driving voltage, maximum external quantum efficiency, FWHM, and roll-off ratio compared to the light-emitting devices of Comparative Examples 1 and 2.
[0689] As confirmed by Table 2, the light-emitting devices of Examples 5 to 8 emit green light and have excellent characteristics in terms of driving voltage, maximum external quantum efficiency, FWHM, and roll-off ratio.
[0690] As confirmed by Table 2, the light-emitting devices of Examples 5 to 8 have improved characteristics in terms of driving voltage, maximum external quantum efficiency, FWHM, and roll-off ratio compared to the light-emitting devices of Comparative Examples 3 to 5.
[0691] As described above, the fused-ring compound represented by Formula 1 according to one or more embodiments can have excellent light-emitting properties, and therefore, electronic devices, such as light-emitting devices, including at least one fused-ring compound represented by Formula 1 can exhibit low driving voltage, high maximum external quantum efficiency, narrow FWHM, and / or low roll-off ratio.
[0692] It should be understood that the exemplary embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the accompanying drawings, 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.
Claims
1. Fused ring compounds, represented by Formula 1: Formula 1 in, In Equation 1, Rings CY1 to CY8 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, L1 is O, S, or C(R) 1a (R) 1b ), L2 is O, S, or C(R) 2a (R) 2b ), The condition is that when L1 is 0 and L2 is 0, the fused ring compound has a symmetrical structure. R1 to R9, R 1a R 1b R 2a and R 2b Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), Two or more of R1 to R9 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, R 1a and R 1b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, R 2a and R 2b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, a1 to a8 are each an independent integer from 0 to 10. Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 The heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are each independently: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof; Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof; -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or Its combination, and Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
2. The fused-ring compound according to claim 1, wherein rings CY1 to CY8 are each independently a phenyl group, a naphthyl group, a phenanthrene group, an anthracene group, a pyridine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzothiophene group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzothiophene group.
3. The fused-ring compound according to claim 1, wherein L1 and L2 are the same as each other.
4. The fused-ring compound according to claim 1, wherein R1 to R9, R 1a R 1b R 2a and R 2b Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl; Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and Q1 through Q9 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.
5. The fused-ring compound according to claim 1, wherein R1 to R9, R 1a R 1b R 2a and R 2b Each independently is: Hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; A group represented by one of formulas 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-350; or -N(Q4)(Q5), and Q4 and Q5 are each as described in claim 1: in, In equations 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * The symbols indicate the binding sites with adjacent atoms. "Ph" represents phenyl, "TMS" represents trimethylsilyl, and "TMG" represents trimethylgermanyl.
6. The fused-ring compound according to claim 1, wherein R1 to R9 are each independently: Hydrogen, deuterium, -F, or cyano; C1-C that is not substituted or is substituted with deuterium, -F, cyano, or a combination thereof 20 Alkyl; or Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, or a combination thereof substituted with cyclopentyl, cyclohexyl, or phenyl.
7. The fused-ring compound according to claim 1, wherein... a1 to a4 are each independent integers from 1 to 10, and R1, R2, R3, and R4 are not hydrogen.
8. The fused-ring compound according to claim 1, wherein the fused-ring compound has a symmetrical structure.
9. The fused-ring compound according to claim 1, wherein the fused-ring compound is represented by formula 1-1: Equation 1-1 in, In Formula 1-1, L1, L2, R1 to R9, and a1 to a8 are each as described in claim 1.
10. The fused-ring compound according to claim 1, wherein the fused-ring compound is represented by formulas 1-2: Formula 1-2 In equation 1-2, L1, L2, R5 to R8, and a5 to a8 are each as described in claim 1, and Z1 to Z4 are as described with respect to R1 to R4 respectively.
11. Light-emitting devices, including: First electrode; Second electrode; as well as An intermediate layer disposed between the first electrode and the second electrode. The intermediate layer includes an emission layer, and The intermediate layer comprises at least one fused ring compound according to any one of claims 1 to 10.
12. The light-emitting device according to claim 11, wherein the emitting layer comprises the at least one fused ring compound.
13. The light-emitting device according to claim 12, wherein the emitting layer further comprises a first body and a second body. The first body comprises a hole transport compound, and the second body comprises an electron transport compound.
14. Light-emitting devices, including: First electrode; Second electrode; as well as An intermediate layer disposed between the first electrode and the second electrode. The intermediate layer includes an emission layer. The emission layer comprises a first body, a second body, and at least one fused ring compound represented by Formula 1. The first body comprises a hole transport compound, and the second body comprises an electron transport compound. Formula 1 In Equation 1, Rings CY1 to CY8 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, L1 is O, S, or C(R) 1a (R) 1b ), L2 is O, S, or C(R) 2a (R) 2b ), R1 to R9, R 1a R 1b R 2a and R 2b Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), Two or more of R1 to R9 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, R 1a and R 1b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, R 2a and R 2b Optionally connected to each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, a1 to a8 are each an independent integer from 0 to 10. Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 The heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are each independently: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof; Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof; -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or Its combination, and Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, 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 C1-C 60 Alkylthio, 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 C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
15. The light-emitting device according to claim 11 or 14, wherein the emission peak wavelength of the emission layer is 490 nm to 550 nm.
16. The light-emitting device according to claim 12 or 14, wherein the fused ring compound is an emitter.
17. The light-emitting device according to claim 13 or 14, wherein the hole-transporting compound comprises at least one π-electron-rich C3-C 60 Cyclic groups, and / or The electron transport compounds include cyano groups, fluorine groups, and C1-C groups containing nitrogen that lacks π electrons. 60 Cyclic groups, phosphine oxide groups, sulfoxide groups, or combinations thereof.
18. The light-emitting device according to any one of claims 12 to 14, wherein the emitting layer further comprises a sensitizer, and the sensitizer is different from the at least one fused-ring compound.
19. The light-emitting device according to claim 18, wherein the sensitizer is an organometallic compound, a delayed fluorescence material, a transient fluorescence material, or a combination thereof. The organometallic compounds mentioned above include transition metals. The transition metal is iridium, osmium, platinum, or palladium.
20. An electronic device, comprising a light-emitting device according to any one of claims 11 to 19.