Organic light-emitting devices
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-01-07
- Publication Date
- 2026-08-14
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Figure CN114725303B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application is based on and claims priority to Korean Patent Application No. 10-2021-0002217 filed with the Korean Intellectual Property Office on January 7, 2021, and all the contents thereof are incorporated herein by reference. Technical Field
[0003] This disclosure relates to organic light-emitting devices. Background Technology
[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that produce full-color images. In addition, OLEDs have a wide viewing angle and exhibit excellent driving voltage and response speed characteristics.
[0005] An OLED comprises an anode, a cathode, and an organic layer between the anode and cathode, including an emitter layer. A hole transport region is located between the anode and the emitter layer, and an electron transport region is located between the emitter layer and the cathode. Holes supplied from the anode can move towards the emitter layer through the hole transport region, and electrons supplied from the cathode can move towards the emitter layer through the electron transport region. Holes and electrons recombine in the emitter layer to generate excitons. Excitons can transition from an excited state to the ground state, thereby producing visible light.
[0006] Various types of organic light-emitting devices are known. However, there remains a need for OLEDs that possess one or more, preferably all, of the following characteristics: high efficiency, long lifetime, and high triplet-triplet fusion (TTF) ratio. Summary of the Invention
[0007] This paper presents an organic light-emitting device comprising a silane compound as the host, which thus exhibits high efficiency, long lifetime, and high triplet-triplet fusion (TTF) ratio.
[0008] Other aspects will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned by practice of the embodiments presented in this disclosure.
[0009] According to aspects of the implementation, the organic light-emitting device may include:
[0010] First electrode,
[0011] The second electrode, and
[0012] An organic layer comprising an emission layer is located between the first electrode and the second electrode.
[0013] The emitter layer may include a host and a dopant, and
[0014] The main body may include at least one silane compound represented by Formula 1.
[0015] Formula 1
[0016]
[0017] In Equation 1,
[0018] Ar1-Ar3 can each be independently 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 groups (e.g., substituted or unsubstituted C2-C) 10 Heterocyclic alkenyl), substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted 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, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9),
[0019] At least one of Ar1-Ar3 may be a 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,
[0020] L 10 C5-C can be substituted or unsubstituted. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,
[0021] a10 can be an integer from 1 to 3, and when a10 is 2 or greater, at least two L's are required.10 They can be the same or different from each other.
[0022] R 10 and R 20 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, 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, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9),
[0023] b10 and b20 can each be an integer from 1 to 8 independently.
[0024] When b10 is 2 or greater, at least two Rs 10 They can be the same or different from each other, and when b20 is 2 or greater, at least two Rs 20 They can be the same or different from each other.
[0025] c10 can be an integer from 1 to 9.
[0026] When c10 is 2 or greater, at least two -[(L 10 ) a10 -(R 10 ) b10 They can be the same as or different from each other.
[0027] Replacement C5-C30 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 C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroarylsulfide group, the substituted monovalent non-aromatic fused polycyclic group, or the substituted monovalent non-aromatic fused heterocyclic group may be:
[0028] Deuterium, -F, -Cl, -Br, -I, -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 alkylthio or C1-C 60 Alkoxy
[0029] Each of the C1-Cs is independently replaced by at least one of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkylthio or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -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-C60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 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 -N(Q) 14 (Q) 15 ), or -B(Q 16 (Q) 17 ),
[0030] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups,
[0031] Each of the following C3-Cs is independently replaced by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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, -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-C60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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 -N(Q) 24 (Q) 25 ), or -B(Q 26 (Q) 27 ),or
[0032] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 ), or -B(Q 36 (Q) 37 ),
[0033] Among them, Q1-Q9, Q 11 -Q 17 Q 21 -Q 27 , and Q 31 -Q 37 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, 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 60aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, 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, and
[0034] Wherein the substituent (group) L 10 R 10 and R 20 The bonds present in the corresponding substituents (groups) pass through their respective rings. Attached Figure Description
[0035] By combination Figure 1 The above and other aspects, features, and advantages of some embodiments of this disclosure will become clearer from the following description. Figure 1 A schematic cross-sectional view of an organic light-emitting device according to an embodiment is shown. Detailed Implementation
[0036] The embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects. 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.
[0037] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with said 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.
[0038] 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.
[0039] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0040] The term "or" means "and / or". It will be further understood that the terms "comprising" or "including", when used in this specification, indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.
[0041] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall 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, shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and in the present disclosure, and shall not be interpreted in an idealized or overly formal sense unless clearly defined herein.
[0042] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations 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 illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.
[0043] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation 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 ±20%, 10%, or 5%.
[0044] In any formula, * and *' each represent a binding site with an adjacent atom or an adjacent functional group.
[0045] The term "room temperature" as used in this article refers to a temperature of approximately 25°C.
[0046] According to an embodiment, a silane compound represented by Formula 1 can be provided:
[0047] Formula 1
[0048]
[0049] In Equation 1, Ar1-Ar3 can each be independently 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 The heteroaryl thio group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heterocyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), or at least one of Ar1-Ar3 may be substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.
[0050] In the implementation method, Ar1-Ar3 can each be independently:
[0051] C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0052] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl;
[0053] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azulel, heptapenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; or
[0054] Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, heptapenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, 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, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cyclolinyl, or quinazolinyl.
[0055] In the implementation, at least one of Ar1-Ar3 can be:
[0056] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azulel, heptapenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; or
[0057] Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, heptapenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, 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, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cyclolinyl, or quinazolinyl.
[0058] In the implementation, Ar1-Ar3 can each be independently substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.
[0059] In the embodiments, Ar1-Ar3 can each independently be: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azulel, heptapenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthracene, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; or
[0060] Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, heptapenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, 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, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cyclolinyl, or quinazolinyl.
[0061] In the implementation method, Ar1-Ar3 can each be independently:
[0062] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, dibenzothiophene, azacarbazole, azadibenzofuranyl, azadibenzothiophene, phen Azine group, or phenothiazine group; or
[0063] Each of the following is independently substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, dibenzothiophenyl, azacarbazole, azadibenzofuranyl, azadibenzothiophenyl, phenyl Azine group, or phenothiazine group: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0064] In Equation 1, L 10 C5-C can be substituted or unsubstituted. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.
[0065] In the implementation, L 10 It can be: phenylene, cyclopentadienylene, indene, naphthylene, azulene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenyl, phenyl Perylene, pentaphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, benzocarbazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenanthridineyl, phenanthridineyl Azinyl, phenthiazinyl, zazacarbazolyl, zazadibenzofuranyl, or zazadibenzothiophenyl;
[0066] Each of the following is independently substituted with at least one of the following: phenylene, cyclopentadienylene, indene, naphthylene, azurylene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenyl, alkyl Perylene, pentaphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, benzocarbazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenanthridineyl, phenanthridineyl Azinyl, phenthiazinyl, zazacarbazolyl, zazadibenzofuranyl, or zazadibenzothiophene: deuterium, -F, -Cl, -Br, -I, 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 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups; or
[0067] Groups represented by formula 2A or 2B:
[0068] Formula 2A
[0069]
[0070] Formula 2B
[0071]
[0072] Among them, in equations 2A and 2B,
[0073] Y 21 -Y 24 Each can be independently a single bond, O, S, N(R) 21 ), C(R 21 (R) 22 ), Si(R) 21 (R) 22 ), C(=O), S(=O), S(=O)2, B(R 21 ), P(R 21), or P(=O)(R 21 ),
[0074] A 21 -A 23 Each group can independently be a phenyl group, a naphthol group, a 1,2,3,4-tetrahydronaphthol group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group.
[0075] R 21 and R 22 Each can be used independently through the R provided in this article. 10 or R 20 Based on the description, and
[0076] * and *' each represent a binding site with an adjacent atom.
[0077] In the implementation, in equations 2A and 2B, Y 21 -Y 24 Each can be independently a single bond, O, S, N(R) 21 ), C(R 21 (R) 22 ), or Si(R) 21 (R) 22 ).
[0078] In the implementation method, Y 21 and Y 22 Each can be a single bond at the same time, and Y 23 and Y 24 Each can be a single key at the same time.
[0079] In the implementation, A 21 -A 23 Each group can be independently a phenyl group, a naphthol group, a pyridine group, or a pyrimidine group.
[0080] In the implementation, A 21 -A 23 Each can be an independent phenyl group or a naphthalene group.
[0081] In Equation 1, a10 can be an integer from 0 to 3, and when a10 is 2 or greater, at least two L... 10 They may be the same as or different from each other.
[0082] In this implementation, a10 can be 0 or 1. For example, a10 can be 0. In this implementation, a10 can be 1.
[0083] In the implementation, when a10 is 0, -(L 10 ) a10 - indicates a single key.
[0084] In Equation 1, R 10 and R 20 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, 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, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).
[0085] In the implementation, R 10 and R 20 Each can be independently:
[0086] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0087] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -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, or pyrimidinyl;
[0088] 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;
[0089] Each of the following is independently substituted with at least one of the following: 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl; or
[0090] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9),
[0091] Q1-Q9 can be independently defined as follows:
[0092] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;
[0093] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or
[0094] Each of the following groups is independently substituted by at least one of the following: 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 or phenyl.
[0095] In the implementation, R 10 and R 20 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, 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 alkylthio or C1-C 20 Alkoxy;
[0096] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl;
[0097] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azulel, heptapenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; or
[0098] Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, heptapenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, 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, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinolinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenanthryl Azine group, or phenothiazine group.
[0099] In the implementation, R 10 and R 20 Each can be independently a deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by formulas 9-1 to 9-19, or a group represented by formulas 10-1 to 10-211:
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106] In formulas 9-1 to 9-19 and 10-1 to 10-211, * indicates a binding site with an adjacent atom, “Ph” represents phenyl, and “TMS” represents trimethylsilyl.
[0107] In the implementation, R 10 and R 20 Each can be independently: hydrogen, deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0108] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, cyano, phenyl, biphenyl, terphenyl, or naphthyl;
[0109] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phen Azine group, or phenothiazine group; or
[0110] Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenyl Azine group, or phenothiazine group: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0111] In the implementation, R 10It can be: deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0112] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, cyano, phenyl, biphenyl, terphenyl, or naphthyl;
[0113] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phen Azine group, or phenothiazine group; or
[0114] Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenyl Azine group, or phenothiazine group: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, carbazole, dibenzofuranyl, or dibenzothiophene.
[0115] In the implementation, R 20 It can be hydrogen, deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl or phenyl.
[0116] In Formula 1, the substituent L 10 R 10 and R 20 The bonds present in the corresponding substituents pass through their respective rings.
[0117] In Equation 1, b10 and b20 can each be independent integers from 1 to 8. When b10 is 2 or greater, at least two R... 10 They can be the same or different from each other. When b20 is 2 or greater, at least two Rs... 20 They may be the same as or different from each other.
[0118] In the implementation, b10 and b20 can each be 1, 2, 3, or 4 independently.
[0119] In the implementation, b10 can be 1.
[0120] In the implementation, b20 can be 1.
[0121] In Equation 1, c10 can be an integer from 1 to 9. When c10 is 2 or greater, at least two -[(L 10 ) a10 -(R 10 ) b10 The groups can be the same as or different from each other.
[0122] In the implementation, c10 can be 1, 2, 3, or 4.
[0123] In the implementation, c10 can be 1 or 2.
[0124] In the implementation, c10 can be 1.
[0125] In Equation 1, the sum of b20 and c10 can be 9.
[0126] In embodiments, the silane compound represented by formula 1 may be represented by one of formulas 10-1 to 10-5:
[0127]
[0128] Among them, in equations 10-1 to 10-5,
[0129] Ar1-Ar3, L 10 a10 and R 10 The descriptions can be found by referring to Ar1-Ar3 and L provided in this article. 10 a10 and R 10 Based on the description, and
[0130] R1-R9 can be obtained independently by referring to the R provided in this article. 20 Understanding is based on the description.
[0131] In an embodiment, the silane compound represented by Formula 1 may be a compound represented by Formula 10-5.
[0132] In the implementation, in formulas 10-1 to 10-5, R 10 It can be: C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0133] Each of the C1-Cs is independently replaced by at least one of the following: 20Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, cyano, phenyl, biphenyl, terphenyl, or naphthyl;
[0134] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, or dibenzothiopheneyl; or
[0135] Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, or dibenzothiopheneyl; deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
[0136] In an embodiment, the silane compound may be one of compounds 1 to 160:
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143] When the silane compound represented by Formula 1 can have an asymmetric structure, it can have low material crystallinity. In embodiments, since close-packing between molecules of the silane compound represented by Formula 1 can be prevented, the silane compound can have relatively superior or improved amorphous thin film properties.
[0144] As described above, the silane compound represented by Formula 1 may possess suitable electrical properties for materials used in organic light-emitting devices, such as host materials, hole transport materials, and electron transport materials in the emitter layer. In embodiments, organic light-emitting devices comprising the silane compound may have high or improved efficiency and / or long or improved lifetime.
[0145] In the implementation, the silane compound represented by Formula 1 satisfies Equation 1:
[0146] Equation 1
[0147] E(T1) <E(S1)<2×E(T1)
[0148] In equation 1,
[0149] E(T1) represents the lowest excited triplet energy level of the silane compound, and E(S1) represents the lowest excited singlet energy level of the silane compound.
[0150] In the implementation, the silane compound represented by Formula 1 satisfies Equation 2:
[0151] Equation 2
[0152] [2×E(T1)]-E(S1)<1eV
[0153] In equation 2,
[0154] E(T1) represents the lowest excited triplet energy level of the silane compound, and E(S1) represents the lowest excited singlet energy level of the silane compound.
[0155] While not wishing to be bound by theory, it is understood that when the silane compound represented by Equation 1 satisfies Equations 1 and / or 2, a triplet-triplet fusion (TTF) phenomenon can occur, in which triplet excitons can fuse to form singlet excitons. Therefore, when the silane compound is applied to an organic light-emitting device, fluorescence emission can occur from the generated singlet excitons due to this TTF phenomenon, and thus, the organic light-emitting device can have improved luminous efficiency and lifetime.
[0156] In the implementation, the silane compound represented by Formula 1 satisfies Equation 2-1:
[0157] Equation 2-1
[0158] [2×E(T1)]-E(S1)<0.5eV
[0159] In equation 2-1,
[0160] E(T1) represents the lowest excited triplet energy level of the silane compound, and E(S1) represents the lowest excited singlet energy level of the silane compound.
[0161] The method for synthesizing the silane compound represented by Formula 1 will be apparent to those skilled in the art by referring to the synthesis examples provided herein.
[0162] Silane compounds represented by Formula 1 are suitable for use as organic layer materials in organic light-emitting devices, such as emission layer materials, hole transport region materials, and / or electron transport region materials. According to an aspect of the embodiment, the organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, comprising an emission layer, said organic layer comprising at least one silane compound represented by Formula 1.
[0163] When the organic light-emitting device has an organic layer comprising a silane compound represented by Formula 1, the organic light-emitting device may have a low driving voltage, high or improved efficiency, high or improved brightness, high or improved quantum efficiency, and long or improved lifetime.
[0164] In an embodiment, in the organic light-emitting device...
[0165] The first electrode can be the anode, and the second electrode can be the cathode.
[0166] The organic layer may include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode.
[0167] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
[0168] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof, but the implementation is not limited thereto.
[0169] In an embodiment, the emitting layer in the organic light-emitting device may include at least one silane compound represented by Formula 1.
[0170] In an embodiment, the emitting layer in the organic light-emitting device may include a host and a dopant, wherein the host may include at least one silane compound represented by Formula 1, and the dopant may include a phosphorescent dopant or a fluorescent dopant. In an embodiment, the dopant may include a phosphorescent dopant (e.g., an organometallic compound represented by Formula 81 provided herein). In addition to the silane compound represented by Formula 1, the host may further include any suitable host.
[0171] The emitting layer can emit red light, green light, or blue light.
[0172] In some embodiments, the emitting layer may include a fluorescent dopant, but the embodiments are not limited thereto.
[0173] In some embodiments, the emitting layer may include a phosphorescent dopant, but the embodiments are not limited thereto.
[0174] In one embodiment, a silane compound represented by Formula 1 may be included in the hole transport region of the organic light-emitting device.
[0175] In an embodiment, the hole transport region of the organic light-emitting device may include at least one hole injection layer, a hole transport layer, or an electron blocking layer, wherein at least one of the hole injection layer, the hole transport layer, or the electron blocking layer may include a silane compound represented by Formula 1.
[0176] In one embodiment, a silane compound represented by Formula 1 may be included in the electron transport region of the organic light-emitting device.
[0177] In an embodiment, the electron transport region of the organic light-emitting device may include at least one hole blocking layer, an electron transport layer, or an electron injection layer, wherein at least one of the hole blocking layer, the electron transport layer, or the electron injection layer may include a silane compound represented by Formula 1.
[0178] In one embodiment, the hole transport region of the organic light-emitting device may include an electron blocking layer, wherein the electron blocking layer may include a silane compound represented by Formula 1. The electron blocking layer may be in direct contact with the emitting layer.
[0179] In one embodiment, the electron transport region of the organic light-emitting device may include a hole-blocking layer, wherein the hole-blocking layer may include a silane compound represented by Formula 1. The hole-blocking layer may be in direct contact with the emitting layer.
[0180] In some embodiments, the organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, comprising an emission layer.
[0181] The emitter layer may include a host and a dopant, and
[0182] The main body may include at least one silane compound represented by Formula 1.
[0183] In one embodiment, the content of the host in the emitting layer of the organic light-emitting device may be greater than the content of the dopant.
[0184] In one embodiment, the main body of the emitting layer in the organic light-emitting device may be composed of the silane compound.
[0185] In an embodiment, the ratio of the emission component emitted from the dopant may be 80% or greater of the total emission component emitted from the emission layer of the organic light-emitting device.
[0186] In an embodiment, the dopant in the emitting layer of the organic light-emitting device may be a fluorescent dopant.
[0187] For example, the fluorescent dopant may be a fused polycyclic compound or a styrene-based compound.
[0188] For example, the fluorescent dopant may include a core containing naphthalene, a core containing fluorene, a core containing spiro-difluorene, a core containing benzo[9,10]fluorene, a core containing dibenzo[9,10]fluorene, a core containing phenanthrene, a core containing anthracene, a core containing fluoranthene, a core containing benzo[9,10]phenanthrene, a core containing pyrene, or a core containing... The core, containing tetraphenyl (also known as tetraphenylene), contains The core may be a perylene-containing core, a pentofen-containing core, an indane-anthracene-containing core, a bianthracite-containing core, or a core represented by any one of formulas 501-1 to 501-18, but the implementation is not limited to these:
[0189]
[0190]
[0191] In some embodiments, the fluorescent dopant may be a styrene-amine based compound or a styrene-carbazole based compound, but the embodiments are not limited thereto.
[0192] In an embodiment, the fluorescent dopant may be a compound represented by formula 501:
[0193] Formula 501
[0194]
[0195] In Equation 501,
[0196] Ar 501 Possible forms:
[0197] Naphthalene group, fluorene group, spiro-difluorene 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, Group, perylene group, pentylenetene group, indene-anthracene group, tetraphenyl (also known as butane) group, bianthracite group, or a group obtained by removing one or more hydrogens from a compound represented by any one of formulas 501-1 to 501-18; or
[0198] Each of the following groups, independently substituted with at least one of the following: naphthyl group, fluorene group, spiro-difluorene 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, Group, perylene group, pentylenetene group, indene-anthracene group, tetraphenyl group, bianthracite group, or a group obtained by removing one or more hydrogens from a compound represented by any one of formulas 501-1 to 501-18: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, 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, 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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 (where Q) 501 -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, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group)
[0199] L 501 -L 503 Each can be independently substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups,
[0200] R 501 and R 502 Each can be independently:
[0201] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl, or dibenzothiopheneyl; or
[0202] Each of the following is independently substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, 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, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, or dibenzothiopheneyl
[0203] xd1-xd3 can each be independently 0, 1, 2, or 3, and
[0204] xd4 can be 0, 1, 2, 3, 4, 5, or 6.
[0205] In the implementation method, in formula 501,
[0206] Ar 501 Possible forms:
[0207] Naphthalene group, fluorene group, spiro-difluorene 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, A group, perylene group, pentylenetene group, indene-anthracene group, bianthracite group, or a group obtained by removing one or more hydrogens from a compound represented by any one of formulas 501-1 to 501-18; or
[0208] Each of the following groups, independently substituted with at least one of the following: naphthyl group, fluorene group, spiro-difluorene 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, Group, perylene group, pentylenetene group, indene-anthracene group, bianthracite group, or a group obtained by removing one or more hydrogens from a compound represented by any one of formulas 501-1 to 501-18: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, 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, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazole, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, or -Si(Q) 501 (Q) 502 (Q) 503 (where Q) 501 -Q 503 Each can be independently hydrogen, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 (alkylthio, phenyl, biphenyl, terphenyl, or naphthyl)
[0209] L 501 -L 503 Each can refer to the L provided in this article. 10 Based on the description,
[0210] xd1-xd3 can each be independently 0, 1, or 2.
[0211] xd4 can be 0, 1, 2, or 3, but the implementation method is not limited to these.
[0212] In an embodiment, the fluorescent dopant may include a compound represented by one of formulas 502-1 to 502-5:
[0213] Formula 502-1
[0214]
[0215] Formula 502-2
[0216]
[0217] Formula 502-3
[0218]
[0219] Formula 502-4
[0220]
[0221] Formula 502-5
[0222]
[0223] Among them, in formulas 502-1 to 502-5,
[0224] X 51 It can be N or C-[(L 501 ) xd1 -R 501 ], X 52 It can be N or C-[(L 502 ) xd2 -R 502 ], X 53 It can be N or C-[(L 503 ) xd3 -R 503 ], X 54 It can be N or C-[(L 504 ) xd4 -R 504 ], X 55 It can be N or C-[(L 505 ) xd5 -R 505 ], X 56 It can be N or C-[(L 506 ) xd6 -R 506 ], X 57 It can be N or C-[(L 507 ) xd7 -R 507 ], X 58 It can be N or C-[(L 508 ) xd8 -R 508 ],
[0225] L 501 -L 508 Each can be obtained through L in reference formula 501 501 Based on the description,
[0226] xd1-xd8 can each be understood through the description of xd1 in Equation 501.
[0227] R 501 -R 508 Each can be independently:
[0228] Hydrogen, deuterium, -F, -Cl, -Br, -I, 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 alkylthio or C1-C 20 Alkoxy;
[0229] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl, or dibenzothiopheneyl; or
[0230] Each of the following is independently substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, 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, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, or dibenzothiopheneyl
[0231] xd11 and xd12 can each be an integer between 0 and 5 independently.
[0232] R 501 -R 504 The two can optionally combine to form a saturated or unsaturated ring.
[0233] R 505 -R 508 The two can optionally combine to form a saturated or unsaturated ring, and
[0234] In formulas 502-2 to 502-5, the substituent L 501 L502 R 501 and R 502 The bonds present in the corresponding substituents pass through their respective rings.
[0235] The fluorescent dopant may include, for example, compounds FD(1) to FD(16) or FD1 to FD13:
[0236]
[0237]
[0238]
[0239]
[0240] In an embodiment, in addition to the silane compound represented by Formula 1, the emitting layer in the organic light-emitting device may further include a phosphorescent dopant.
[0241] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 81:
[0242] Formula 81
[0243] M(L 81 ) n81 (L 82 ) n82
[0244] Where L 81 It can be a ligand represented by Equation 81A.
[0245] Formula 81A
[0246]
[0247] Among them, in formulas 81 and 81A,
[0248] M can be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
[0249] n81 can be an integer from 1 to 3; and when n81 is 2 or greater, at least two L... 81 They can be the same or different from each other.
[0250] L 82 It can be an organic ligand, and n82 can be an integer from 0 to 4; and when n82 is 2 or greater, at least two L... 82 They can be the same or different from each other.
[0251] Y 81 -Y84 They can be carbon (C) or nitrogen (N) independently.
[0252] Y 81 and Y 82 They can be connected to each other via single or double bonds, and Y 83 and Y 84 They are connected to each other via single or double bonds.
[0253] CY 81 and CY 82 Each can be independently classified as C5-C 30 Carbocyclic groups or C2-C 30 Heterocyclic groups,
[0254] CY 81 and CY 82 They can optionally be linked via organic linker groups.
[0255] R 81 -R 85 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, 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 81 (Q) 82 (Q) 83 -N(Q) 84 (Q) 85 -B(Q)86 (Q) 87 ), or -P(=O)(Q 88 (Q) 89 ),
[0256] a81-a83 can each be an integer from 0 to 5 independently.
[0257] When a81 is 2 or greater, at least two Rs 81 They can be the same or different from each other.
[0258] When a82 is 2 or greater, at least two R values are required. 82 They can be the same or different from each other.
[0259] When a81 is 2 or greater, two adjacent R 81 They can be optionally combined to form saturated or unsaturated C2-C 30 Ring (e.g., benzene ring, cyclopentane ring, cyclohexane ring, cyclopentene ring, cyclohexene ring, norcamphene ring (bicyclic [2.2.1]heptane ring), naphthyl ring, benzo[2.2.1]indole ring, benzo[3]furan ring, benzo[4]thiophene ring, pyridine ring, pyrimidine ring, or pyrazine ring), or ring containing at least one R 88 Substitution of saturated or unsaturated C2-C 30 Rings (e.g., each independently bounded by at least one R) 88 Substituted benzene rings, cyclopentane rings, cyclohexane rings, cyclopentene rings, cyclohexene rings, norcamphene rings (bicyclic [2.2.1]heptane rings), naphthyl rings, benzo[2.2.1]indene rings, benzo[2.2.1]indole rings, benzo[2.2.1]furan rings, benzo[2.2.1]thiophene rings, pyridine rings, pyrimidine rings, or pyrazine rings),
[0260] When a82 is 2 or greater, two adjacent R 82 They can be optionally combined to form saturated or unsaturated C2-C 30 Ring (e.g., benzene ring, cyclopentane ring, cyclohexane ring, cyclopentene ring, cyclohexene ring, norcamphene ring (bicyclic [2.2.1]heptane ring), naphthyl ring, benzo[2.2.1]indole ring, benzo[3]furan ring, benzo[4]thiophene ring, pyridine ring, pyrimidine ring, or pyrazine ring), or ring containing at least one R 89 Substitution of saturated or unsaturated C2-C 30 Rings (e.g., each independently bounded by at least one R) 89 Substituted benzene rings, cyclopentane rings, cyclohexane rings, cyclopentene rings, cyclohexene rings, norcamphene rings (bicyclic [2.2.1]heptane rings), naphthyl rings, benzo[2.2.1]indene rings, benzo[2.2.1]indole rings, benzo[2.2.1]furan rings, benzo[2.2.1]thiophene rings, pyridine rings, pyrimidine rings, or pyrazine rings),
[0261] R 88 You can refer to the R provided in this article 81 Based on the description,
[0262] R 89 You can refer to the R provided in this article 82 Based on the description,
[0263] In Equation 81A, * and *' each represent the binding site with M in Equation 81, and
[0264] 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 C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, 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 may be: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, 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, 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or -Si(Q) 91 (Q) 92 (Q)93 ),
[0265] Q 81 -Q 89 and Q 91 -Q 93 Each can be independently hydrogen, deuterium, or C1-C 60 Alkyl, 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, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.
[0266] In the implementation method, in formula 81A,
[0267] a83 can be 1 or 2, and
[0268] R 83 -R 85 Each can be independently:
[0269] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;
[0270] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or
[0271] Each of the following groups is independently substituted by at least one of the following: 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 or phenyl, but the implementation methods are not limited to these.
[0272] In the implementation method, in formula 81A,
[0273] Y 81 It can be N, Y 82 and Y 83 Each can be C, Y 84 It can be N or C, and
[0274] CY 81 and CY 82 Each of these groups can be independently cyclopentadienyl group, phenyl group, heptadienyl group, indene group, naphthyl group, azulene group, indane group, acenaphthene group, fluorene group, spiro-difluorene 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, perylene groups, pentanephenyl groups, hexaphenyl groups, rutin groups, halophenyl groups, ovoidphenyl groups, pyrrole groups, isoindole groups, indole groups, indazole groups, pyrazole groups, imidazole groups, triazole groups, azole group, iso- azole group, Diazole group, thiazole group, isothiazole group, thiadiazole group, purine group, furan group, thiophene group, pyridine group, pyrimidine group, quinoline group, isoquinoline group, benzo[a]quinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, benzo[a]furan group, benzo[a]thiophene group, isobenzo[a]thiazole group, benzo[a] azole group, isobenzox Azazole group, benzocarbazole group, dibenzocarbazole group, imidazopyridine group, imidazopyrimidine group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzothiophene group, or 2,3-dihydro-1H-imidazolium group.
[0275] In the implementation method, in formula 81A, Y 81 It can be N, Y 82 -Y 84 Each can be C, CY 81 It can be a 5-membered ring containing two nitrogen atoms as cyclic atoms, and CY 82 It can be a phenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but the implementation methods are not limited to these.
[0276] In the implementation method, in formula 81A, Y 81 It can be N, Y 82 -Y 84 Each can be C, CY 81 It can be an imidazole group or a 2,3-dihydro-1H-imidazole group, and CY 82 It can be a phenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but the implementation methods are not limited to these.
[0277] In the implementation method, in formula 81A,
[0278] Y 81 It can be N, Y 82 -Y 84 Each can be C.
[0279] CY 81 It can be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, azole group, iso- azole group, Diazole group, thiazole group, isothiazole group, thiadiazole group, pyridine group, pyrimidine group, quinoline group, isoquinoline group, benzo[a]quinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, cyclophosphine group, benzimidazole group, isobenzothiazole group, benzo[a] azole group, or isobenzox azole group, or
[0280] CY 82 It can be a cyclopentadienyl group, phenyl group, naphthyl group, fluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, benzo[9,10]phenanthrene group, pyrene group, Group, perylene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, or dibenzothiophene group.
[0281] In the implementation method, in formula 81A,
[0282] R 81 and R 82 Each can be independently:
[0283] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0284] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -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, phenyl, naphthyl, pyridyl, or pyrimidinyl;
[0285] 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;
[0286] Each of the following is independently substituted with at least one of the following: 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -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-C20 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl; or
[0287] -B(Q 86 (Q) 87 ) or -P(=O)(Q 88 (Q) 89 ),
[0288] Q 86 -Q 89 Each can be independently:
[0289] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;
[0290] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or
[0291] Each of the following groups is independently substituted by at least one of the following: 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 or phenyl.
[0292] In the implementation, in formula 81A, the quantity of R is a81. 81 and R with a quantity of a82 82 At least one of them can be a cyano group.
[0293] In the implementation, in formula 81A, the quantity of R is a82. 82 At least one of them can be a cyano group.
[0294] In the implementation, in formula 81A, the quantity of R is a81. 81 and R with a quantity of a82 82 At least one of them can be deuterium.
[0295] In the implementation method, in formula 81, L 82 The ligand can be represented by one of equations 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114):
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302] In equations 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114),
[0303] X1 can be O, S, C (Z) 21 (Z) 22 ), or N(Z 23 ),
[0304] X 31 It can be N or C(Z) 1a ), X 32 It can be N or C(Z) 1b ),
[0305] X 41 It can be O, S, N (Z) 1a ), or C(Z) 1a (Z) 1b ),
[0306] Z1-Z4, Z 1a Z 1bZ 1c Z 1d Z 2a Z 2b Z 2c Z 2d Z 11 -Z 14 and Z 21 -Z 23 Each can be independently:
[0307] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy;
[0308] Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -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, or pyrimidinyl;
[0309] 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;
[0310] Each of the following is independently substituted with at least one of the following: 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl; or
[0311] -B(Q 86 (Q) 87 ) or -P(=O)(Q 88 (Q)89 ),
[0312] Q 86 -Q 89 Each can be independently:
[0313] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;
[0314] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or
[0315] Each of the following groups is independently substituted by at least one of the following: 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 or phenyl
[0316] d2 and e2 can each be 0 or 2 independently.
[0317] e3 can be an integer between 0 and 3.
[0318] d4 and e4 can each be an integer between 0 and 4 independently.
[0319] d6 and e6 can each be an integer between 0 and 6 independently.
[0320] d8 and e8 can each be an integer from 0 to 8 independently, and
[0321] * and *' each represent the binding site with M in Equation 1.
[0322] In one embodiment, in equation 81, M can be Ir, and the sum of n81 and n82 can be 3. In another embodiment, in equation 81, M can be Pt, and the sum of n81 and n82 can be 2.
[0323] In an embodiment, the organometallic compound represented by Formula 81 may be neutral and may not include ion pairs of cations and anions.
[0324] In embodiments, the organometallic compound represented by Formula 81 may include at least one of compounds PD1 to PD78 or Fir6, but embodiments are not limited thereto:
[0325]
[0326]
[0327]
[0328]
[0329] In one embodiment, the emitting layer in the light-emitting device can emit blue light having a maximum emission wavelength in the range of about 410 nanometers (nm) to about 490 nm.
[0330] As used herein, the statement “(organic layer) comprises at least one silane compound represented by Formula 1” can be interpreted as meaning “(organic layer) may comprise one silane compound represented by Formula 1 or two or more different silane compounds represented by Formula 1”.
[0331] For example, the organic layer may include only compound 1 as the silane compound. In an embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In an embodiment, the organic layer may include compounds 1 and 2 as the silane compound. In an embodiment, compounds 1 and 2 may exist in the same layer (e.g., both compounds 1 and 2 may exist in the emitting layer) or in different layers (e.g., compound 1 may exist in the emitting layer, and compound 2 may exist in the hole-blocking layer).
[0332] The first electrode can be the anode of the hole injection electrode, and the second electrode can be the cathode of the electron injection electrode. In one embodiment, the first electrode can be the cathode of the electron injection electrode, and the second electrode can be the anode of the hole injection electrode.
[0333] As used herein, the term "organic layer" refers to a single layer or multiple layers between a first electrode and a second electrode in an organic light-emitting device. The "organic layer" may include not only organic compounds but also organometallic complexes containing metals.
[0334] Figure 1 A schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment is shown. Hereinafter, reference will be made to... Figure 1 The structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device are described. The organic light-emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which are stacked sequentially in the order stated herein.
[0335] A substrate may be disposed below the first electrode 11 or on the second electrode 19. The substrate may be any suitable substrate used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0336] The first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be a material with a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The material used to form the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In embodiments, the material used to form the first electrode 11 can be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
[0337] The first electrode 11 may have a single-layer structure or a multi-layer structure including multiple layers. In one embodiment, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited to this.
[0338] The organic layer 15 may be on the first electrode 11.
[0339] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.
[0340] The hole transport region may be located between the first electrode 11 and the emitter layer.
[0341] The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, or a buffer layer.
[0342] The hole transport region may include either a hole injection layer or a hole transport layer only. In one embodiment, the hole transport region may include a hole injection layer and a hole transport layer sequentially stacked on the first electrode 11. In another embodiment, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked on the first electrode 11.
[0343] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, tape casting, and / or Langmuir-Broguet (LB) deposition.
[0344] When a hole injection layer is formed by vacuum deposition, for example, the vacuum deposition can be carried out at a temperature in the range of about 100°C to about 500°C for about 10 -8 To-10 -3 Under vacuum pressure within the Torr range and at approximately 0.01 angstroms / second -about The process is carried out at a rate within the range, although the conditions may vary depending on the compound used as the hole injection material and the structure and thermal properties of the desired hole injection layer, but the implementation is not limited thereto.
[0345] When a hole injection layer is formed by spin coating, the spin coating can be carried out at a rate in the range of about 2,000 rpm to about 5,000 rpm and at a temperature in the range of about 80°C to about 200°C to promote solvent removal after spin coating. Although the conditions may vary depending on the compound used as the hole injection material and the structure and thermal properties of the desired hole injection layer, the implementation is not limited thereto.
[0346] The conditions for forming the hole transport layer and the electron blocking layer can be inferred from the conditions for forming the hole injection layer.
[0347] The hole transport region may include at least one of the following: m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), a compound represented by formula 201, or a compound represented by formula 202:
[0348]
[0349] Formula 201
[0350]
[0351] Formula 202
[0352]
[0353] In Equation 201, Ar 101 and Ar 102 Each can be independently:
[0354] Phenylidene, cyclopentadienyl, indene, naphthyl, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, tetraphenyl, alkyl alkyl, perylene, or pentanediphenyl; or
[0355] Each of the following is independently substituted with at least one of the following: phenylene, cyclopentadienylene, indene, naphthylene, azurylene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenyl, alkyl -1, -2, -3, -4, -5, -1, -2, -3, -4, -5, -6, -1, -2, -3, -4, -5, -6, -6, -3, -4, -5, -6, -6, -6, -6, -7 ...6, -7, -6, 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.
[0356] In Equation 201, xa and xb can each be an integer from 0 to 5 independently. In an embodiment, xa and xb can each be 0, 1, or 2 independently. In an embodiment, xa can be 1 and xb can be 0, but the embodiment is not limited to these.
[0357] In equations 201 and 202, R 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:
[0358] Hydrogen, deuterium, -F, -Cl, -Br, -I, 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 (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy), or C1-C 10Alkylthio (e.g., methylthio, ethylthio, propanethio, butylthio, pentylthio, or hexylthio);
[0359] Each of the C1-Cs is independently replaced by at least one of the following: 10 Alkyl, C1-C 10 alkylthio or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, 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;
[0360] Phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene; or
[0361] Each of the following groups, independently substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 alkylthio or C1-C 10 Alkyl groups, but the implementation methods are not limited to this.
[0362] In Equation 201, R 109 Possible forms:
[0363] phenyl, naphthyl, anthraceneyl, or pyridyl; or
[0364] Each of the following groups is independently substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, 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, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, or pyridyl.
[0365] In some embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments are not limited thereto:
[0366] Formula 201A
[0367]
[0368] In Equation 201A, R 101 R 111 R 112 and R 109 You can refer to the R provided in this article respectively. 101 R 111 R112 and R 109 Understanding is based on the description.
[0369] In embodiments, the compounds represented by formulas 201 and 202 may include compounds HT1 to HT20, but the embodiments are not limited thereto:
[0370]
[0371]
[0372]
[0373] The thickness of the hole transport region can be approximately 100 angstroms. -about For example, about -about about -about about -about about -about about -about about -about about -about about -about or about -about Within the range. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately -about For example, about -about -about about -about about -about about -about about -about about -about about -about or about -about The thickness of the hole transport layer can be within the range of [specific range]. -about For example, about -about about -about about -about about -about about -about or about -about Within these ranges. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within any of these ranges, excellent or improved hole transport characteristics can be obtained without a significant increase in driving voltage.
[0374] In addition to the aforementioned materials, the hole transport region may include a charge-generating material to improve the electrical conductivity of the hole transport region. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.
[0375] The charge-generating material may include, for example, a p-doper. The p-doper may include one of the following: quinone derivatives, metal oxides, and compounds containing a cyano group, but the embodiments are not limited thereto. For example, non-limiting examples of the p-doper include quinone derivatives such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as compound HT-D1 or compound HT-D2, but the embodiments are not limited thereto.
[0376]
[0377] The hole transport region may further include a buffer layer.
[0378] The buffer layer can compensate for the optical resonant distance depending on the wavelength of the light emitted from the emission layer to improve the efficiency of the organic light-emitting device.
[0379] The emitter layer can be formed on the hole transport region using one or more suitable methods such as vacuum deposition, spin coating, casting, or LB deposition. When the emitter layer is formed by vacuum deposition or spin coating, the vacuum deposition and coating conditions used to form the emitter layer can be substantially similar to those used to form the hole injection layer, although the conditions may vary depending on the compound used.
[0380] The hole transport region may further include an electron blocking layer. The electron blocking layer may include any suitable material, such as mCP, but the implementation is not limited thereto.
[0381]
[0382] The thickness of the electron blocking layer can be approximately -about and in some implementation methods -about Within these ranges. While it is not desirable to be bound by theory, it is understood that when the thickness of the electron blocking layer is within any of these ranges, excellent or improved electron blocking characteristics can be obtained without a significant increase in driving voltage.
[0383] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In an embodiment, the emitting layer may have a structure in which the red emitting layer, green emitting layer, and / or blue emitting layer are stacked to emit white light. In an embodiment, the structure of the emitting layer can be modified.
[0384] The emission layer may include a silane compound represented by Formula 1.
[0385] In an embodiment, the emitter layer may consist only of silane compounds represented by Formula 1.
[0386] In an implementation, the emission layer may include
[0387] Silane compounds represented by Formula 1, and
[0388] i) A second compound that is different from the silane compound represented by Formula 1 as the main component;
[0389] ii) Organometallic compounds represented by formula 81; or
[0390] iii) Any combination of i) and ii).
[0391] The silane compounds represented by Formula 1 and the organometallic compounds represented by Formula 81 can be understood, respectively, by referring to the descriptions of those provided herein. The second compound can be any suitable host available in the art for use in organic light-emitting devices.
[0392] When the emitting layer comprises a substrate and a dopant, the amount of the dopant can be selected from a range of about 0.01 parts by weight to about 20 parts by weight based on about 100 parts by weight of the emitting layer, but the implementation is not limited thereto. For example, the amount of the dopant can come from the following ranges: about 0.01 parts by weight to about 20 parts by weight, about 0.01 parts by weight to about 15 parts by weight, about 0.01 parts by weight to about 10 parts by weight, about 0.01 parts by weight to about 7 parts by weight, about 0.01 parts by weight to about 5 parts by weight, about 0.01 parts by weight to about 3 parts by weight, about 0.01 parts by weight to about 1 part by weight, or about 0.01 parts by weight to about 0.5 parts by weight, but the implementation is not limited thereto. While not wishing to be bound by theory, it is understood that when the amount of the dopant is within this range, light emission without quenching can be achieved.
[0393] When the emitter layer comprises a silane compound represented by Formula 1 and the second compound, the weight ratio of the silane compound represented by Formula 1 to the second compound can be in the range of about 1:99 to about 99:1, for example, about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60. In an embodiment, the weight ratio of the silane compound represented by Formula 1 to the second compound can be in the range of about 60:40 to about 40:60. While not wishing to be bound by theory, it is understood that when the weight ratio of the silane compound represented by Formula 1 to the second compound in the emitter layer is within any of these ranges, charge transport balance can be effectively achieved in the emitter layer.
[0394] The thickness of the emission layer can be approximately -about and in the implementation method -about Within these ranges. While it is not desirable to be bound by theory, it is understood that when the thickness of the emitting layer is within any of these ranges, improved light emission characteristics can be obtained without a significant increase in driving voltage.
[0395] In one implementation, the electron transport region may be formed on the emitter layer.
[0396] The electron transport region may include at least one of a hole blocking layer, an electron transport layer, or an electron injection layer.
[0397] In some embodiments, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the embodiments are not limited to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.
[0398] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer can be inferred based on the conditions for forming the hole injection layer.
[0399] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP or Bphen, but the implementation is not limited thereto:
[0400]
[0401] The hole-blocking layer may include a silane compound represented by Formula 1.
[0402] The thickness of the hole-blocking layer can be approximately -about For example, about -about about -about about -about about -about about -about about -about about -about or about -about Within these ranges. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within any of these ranges, excellent or improved hole blocking characteristics can be obtained without a significant increase in driving voltage.
[0403] The electron transport layer may include at least one of BCP, Bphen, Alq3, BAlq, TAZ, or NTAZ:
[0404]
[0405] In some embodiments, the electron transport layer may include at least one compound ET1, ET2, or ET3, but the embodiments are not limited thereto.
[0406]
[0407] The thickness of the electron transport layer can be approximately -about and in one implementation method -about about -about about -about about -about about -about or about -about Within these ranges. While it is not desirable to be bound by theory, it is understood that when the thickness of the electron transport layer is within any of these ranges, excellent or improved electron transport characteristics can be obtained without a significant increase in driving voltage.
[0408] In addition to the materials described herein, the electron transport layer may further comprise a material containing metal.
[0409] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or compound ET-D2.
[0410]
[0411] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.
[0412] The electron injection layer may include at least one of LiQ, LiF, NaCl, CsF, Li2O, or BaO.
[0413] The thickness of the electron injection layer can be approximately -about and in one implementation method -about about -about about -about about -about or about -about Within these ranges. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within any of these ranges, excellent or improved electron injection characteristics can be obtained without a significant increase in driving voltage.
[0414] The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a material with a relatively low work function, such as a metal, alloy, conductive compound, or a mixture thereof. Examples of materials used to form the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to fabricate a top-emitting light-emitting device. In embodiments, the material used to form the second electrode 19 may be varied.
[0415] In the previous text, it has been referenced Figure 1 Organic light-emitting device 10 has been described, but the implementation is not limited thereto.
[0416] Definition of terminology
[0417] 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 1-60 carbon atoms. Examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C1-C" is used as in this document. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.
[0418] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups. Examples include methoxy, ethoxy, and isopropoxy.
[0419] The term "C1-C" used in this article 60 "Alkylthio" refers to the group consisting of -SA 104 (where A) 104 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methylthio, ethylthio, and isopropylthio.
[0420] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60 A group formed by placing at least one carbon-carbon double bond at the middle or end of an alkyl group. Examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alkenyl" refers to a group with a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.
[0421] As used in this article, the term "C2-C" 60 "Alkyne" refers to the group formed by the combination of C2-C... 60 A group formed by placing at least one carbon-carbon triple bond at the middle or end of an alkyl group. Examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.
[0422] As used in this article, the term "C3-C" 10"Cycloalkyl" refers to a monovalent cyclic saturated hydrocarbon group comprising 3-10 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.
[0423] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent monocyclic saturated group comprising at least one heteroatom of N, O, P, Si, or S as a cyclic atom and 1-10 carbon atoms. Examples include tetrahydrofuranyl and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0424] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the overall molecular structure is non-aromatic. Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.
[0425] As used in this article, the term "C1-C" 10 Heterocyclic alkenyl groups (e.g., C2-C) 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group whose ring includes at least one heteroatom of N, O, P, Si, or S as a cyclic atom, 1-10 carbon atoms, and at least one double bond. C1-C 10 Examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0426] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6-60 carbon atoms. For example, the term "C6-C" is used herein. 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and... Base. When C6-C 60 Aryl and C6-C60 When each of the aryl groups comprises multiple rings, the multiple rings can be fused together. As used herein, the term "C7-C" is relevant to this context. 60 "alkylaryl" refers to an alkyl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl.
[0427] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, or S as a cyclizing atom and 1-60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system with at least one heteroatom selected from N, O, P, Si, or S as a cyclic atom and 1-60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises multiple rings, the multiple rings can be fused together. As used herein, the term "C2-C" is relevant to this context. 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 Mixed aromatic compounds.
[0428] As used in this article, the term "C6-C" 60 "Aryloxy group" represents -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein, C6-C 60 Arylthioyl group represents -SA 103 (where A) 103 For C6-C 60 Aryl).
[0429] As used in this article, the term "C1-C" 60 "Heteroaryloxy" refers to -OA 105 (where A) 105 For C1-C 60 (Heteroaryl), and as used herein by the term "C6-C" 60 "Heteroarylsulfonyl" indicates -SA 106 (where A) 106 For C1-C 60 (Miscellaneous aromatics).
[0430] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more fused rings and having only carbon atoms (e.g., the number of carbon atoms may be in the range of 8-60) as cyclic atoms, wherein the molecular structure as a whole is nonaromatic. Examples of said monovalent nonaromatic fused polycyclic groups include the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as said monovalent nonaromatic fused polycyclic groups.
[0431] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings and having at least one heteroatom selected from N, O, P, Si, or S and a carbon atom (e.g., the number of carbon atoms may range from 1 to 60) as the cyclic atom, wherein the molecular structure is nonaromatic overall. Examples of such 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 a structure substantially the same as that of the monovalent nonaromatic fused heterocyclic group.
[0432] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group consisting of only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbon ring group can be a monocyclic group or a polycyclic group.
[0433] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group comprising 1-30 carbon atoms and at least one heteroatom selected from N, O, P, Si, or S as the cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic.
[0434] 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 60Alkyl aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 heteroaryl thiols, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, or the substituted monovalent non-aromatic fused heterocyclic group may be:
[0435] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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 alkylthio or C1-C 60 Alkoxy;
[0436] Each of the C1-Cs is independently replaced by at least one of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkylthio or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 11 (Q) 12 ), -Si(Q 13 (Q)14 (Q) 15 -B(Q) 16 (Q) 17 ), or -P(=O)(Q 18 (Q) 19 );
[0437] 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group;
[0438] Each of the following C3-Cs is independently replaced by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, 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, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10Cycloalkenyl, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), or -P(=O)(Q 28 (Q) 29 );or
[0439] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), or -P(=O)(Q 38 (Q) 39 ),
[0440] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, deuterated, C1-C 60 Alkyl, or C6-C 60 At least one substituted C1-C of aryl 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio group, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, deuterium, C1-C 60 Alkyl, or C6-C 60 At least one substituted C6-C of aryl group 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroaryl thiols, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group.
[0441] The compounds and organic light-emitting devices according to the embodiments will be described in detail below with reference to the synthesis examples and examples; however, the present disclosure is not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of A.
[0442] Example
[0443] Synthesis Example 1: Synthesis of Compound 10
[0444]
[0445] 9-Bromo-10-phenylanthracene (1.0 eq.), triphenylsilylacetylene (2.0 eq.), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2) (0.1 eq.), cuprous iodide (I) (CuI) (0.11 eq.), and piperidine (8.0 eq.) were added to the reaction vessel, followed by purging with nitrogen. Triethylamine (Et3N) was then added as a solvent, and the mixture was heated under reflux for 20 hours. A saturated aqueous solution of ammonium chloride was added, followed by extraction with dichloromethane. After drying with anhydrous magnesium sulfate, the solvent was removed, and the mixture was purified by column chromatography and recrystallized (using ethyl acetate and hexane) to give compound 10 as a white solid. Yield: 32%, LCMS [M+H, m / z] 537.2
[0446] Synthesis Example 2: Synthesis of Compound 24
[0447]
[0448] Compound 24 was synthesized in substantially the same manner as in Synthetic Example 1, except that 9-bromo-10-(naphth-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and dibenzo[b,d]furan-2-yl(ethynyl)diphenylsilane was used instead of triphenylsilylacetylene. Yield: 35%, LCMS [M+H, m / z] 677.2
[0449] Synthesis Example 3: Synthesis of Compound 51
[0450]
[0451] Compound 51 was synthesized in essentially the same manner as in Synthetic Example 1, except that 9-bromo-10-(naphthyl-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene. Yield: 32%, LCMS [M+H, m / z] 587.2
[0452] Synthesis Example 4: Synthesis of Compound 56
[0453]
[0454] Compound 56 was synthesized in essentially the same manner as in Synthetic Example 1, except that 2-(10-bromoanthracene-9-yl)dibenzo[b,d]furan was used instead of 9-bromo-10-phenylanthracene. Yield: 35%, LCMS [M+H, m / z] 627.2.
[0455] Example 1
[0456] Patterned ITO glass substrates (50 mm × 50 mm × 0.7 mm) were ultrasonically treated in acetone, isopropanol and distilled water for 20 minutes each, and then heat-treated at 250°C for 20 minutes.
[0457] Afterwards, through the HATCN is deposited at a rate that forms a hole injection layer on the ITO electrode (anode) on the glass substrate to approximately [missing information]. The thickness. Through... The rate of NPB deposition forms a hole transport layer on the hole injection layer, resulting in a hole transport layer with approximately [missing information]. The thickness.
[0458] Then, by means of The rate of mCP deposition forms an electron blocking layer on the hole transport layer, resulting in an electron blocking layer with... The thickness.
[0459] By respectively and The deposition rate co-deposited compound 10 (as the host) and compound D1 (as the dopant) to form an emitter layer on the electron blocking layer to achieve the desired emission layer. The thickness.
[0460] By using DPEPO and LiQ (1:1) The deposition rate deposits on the emitter layer to form an electron transport layer to have The thickness. By using LiQ with The deposition rate deposits on the electron transport layer to form an electron injection layer to achieve the desired deposition rate. The thickness. A second electrode (cathode) is formed by vacuum depositing aluminum (Al) onto the electron-injection layer to achieve the desired thickness. The thickness, thus completing the having Fabrication of organic light-emitting devices with a specific structure.
[0461]
[0462] Examples 2-4
[0463] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of compound 10 as the main component in the formation of the emitting layer.
[0464] Comparative Examples 1 and 2
[0465] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound A or compound 10 was used as the single light-emitting material, as shown in Table 1.
[0466] Evaluation Example 1: Evaluation of the characteristics of organic light-emitting devices
[0467] The external quantum efficiency (EQE), TTF ratio, and lifetime (T) of the organic light-emitting devices in Examples 1-4 and Comparative Examples 1 and 2 were evaluated using relative values. 97 The results are shown in Table 1. A Keithley 2400 ammeter / voltmeter and a luminance meter (Minolta Cs-1000A) were used for evaluation. Lifetime (T) 97 The TTF (Total Fiber Transient Electroluminescence) ratio refers to the time required for the brightness of an organic light-emitting device to decrease from an initial brightness of 6000 nits to 97% of its original brightness. The TTF ratio is measured as the square of the reciprocal of the y-intercept in a graph of the square root of the 1 / TrEL intensity (1 / sqrt(TrEL)) versus time, where the decay of transient electroluminescence (TrEL) is measured from 500 nanoseconds (ns) to 4000 ns. In Table 1, “ND” indicates “Not Detected”.
[0468] Table 1
[0469]
[0470]
[0471] As shown in Table 1, it was found that compared with the organic light-emitting devices of Comparative Examples 1 and 2, the organic light-emitting devices of Examples 1-4 each simultaneously have a low driving voltage, an improved or comparable level of EQE, a significantly superior or improved lifetime, and a high or improved TTF ratio.
[0472] As is clear from the foregoing description, the silane compounds have been found to have excellent or improved electrical properties and thermal stability, and organic light-emitting devices comprising the silane compounds as the main body have high or improved efficiency, long or improved lifetime, and high or improved TTF ratio.
[0473] It should be understood that the embodiments described herein are to be considered in the 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. Although 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 of the invention as defined by the appended claims.
Claims
1. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer comprising an emission layer is located between the first electrode and the second electrode. The emitter layer comprises a host and a dopant, and The main body includes at least one silane compound represented by Formula 1: Formula 1 In Equation 1, Ar1-Ar3 are each independently 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, L 10 C5-C, whether substituted or not 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, a10 is an integer between 0 and 3, and when a10 is 2 or greater, at least two L... 10 Whether they are the same or different, R 10 and R 20 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl; Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, hepta-enyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, phenyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, indole, naphthyl, azuleyl, heptapenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, phenanthyl, phenanthryl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, phenyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinolinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenanthryl Zinel or phenothiazinel, Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkyl groups: -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, or cycloheptenyl; Cycloheptyl, cyclooctyl, adamantyl, norcamphenyl, or norbornenyl; Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, phenyl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: -CD3, -CD2H, -CDH2, -CF3, -CF2H, or -CFH2; Each of the C1-C segments is independently substituted by at least one of biphenyl or terphenyl groups. 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; biphenyl or terphenyl; or Each of the following biphenyl or terphenyl groups is independently substituted with at least one of the following: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl, b10 and b20 are each independent integers from 1 to 8. When b10 is 2 or greater, at least two Rs 10 They are either the same or different, and when b20 is 2 or greater, at least two Rs are equal or different. 20 Whether they are the same or different, c10 is an integer from 1 to 9. When c10 is 2 or greater, at least two -[(L 10 ) a10 -(R 10 ) b10 They are the same or different from each other. Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C6-C 60 Aryl, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is: Deuterium, -F, -Cl, -Br, -I, -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 alkylthio or C1-C 60 Alkoxy; Each of the C1-Cs is independently replaced by at least one of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkylthio or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 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 -N(Q) 14 (Q) 15 ), or -B(Q 16 (Q) 17 ); C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups; Each of the following C3-Cs is independently replaced by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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, -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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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 -N(Q) 24 (Q) 25 ), or -B(Q 26 (Q) 27 );or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、 or -B(Q 36 )(Q 37 ), Among them, Q1-Q9, Q 11 -Q 17 Q 21 -Q 27 , and Q 31 -Q 37 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, 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, and Where the substituent L 10 R 10 and R 20 The bonds present in the corresponding substituents pass through their respective rings.
2. The organic light-emitting device as described in claim 1, wherein Ar1-Ar3 are each independently: Phenyl, indene, naphthyl, azulel, heptalenyl, indaneyl, acenaphthyl, fluorenyl, phenanthyl, anthracene, fluoranthyl, benzo[9,10]phenanthyl, pyrene, phenyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azine, phenothiazine, imidazopyrimidin, or imidazopyridin; and Each of the following is independently substituted with at least one of the following: phenyl, indene, naphthyl, azulel, heptalenyl, indaneyl, acenaphthyl, fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthyl, pyrene, phenyl, tetraphenyl, Peryl, pentylenol, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxalinyl, phenazinyl, benzo[] Azolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl azole group, Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, phen Azinyl, phenothiazinyl, imidazopyrimidinyl, or imidazopyridyl: deuterium, -F, -Cl, -Br, -I, 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, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cyclolinyl, or quinazolinyl.
3. The organic light-emitting device as described in claim 1, wherein L 10 for: Phenylidene, cyclopentadienyl, indene, naphthyl, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, phenyl, tetraphenyl, phenylene Perylene, pentaphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, benzocarbazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenanthridineyl, phenanthridineyl Azinyl, phenthiazinyl, zazacarbazolyl, zazadibenzofuranyl, or zazadibenzothiophenyl; Each of the following is independently substituted with at least one of the following: phenylene, cyclopentadienylene, indene, naphthylene, azurylene, heptadienylene, acenaphthelene, fluorene, phenenylene, anthracene, fluorenylene, benzo[9,10]phenenylene, pyrene, phenenylene, benzotetraphenylene, phenylene Perylene, pentaphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, dibenzothiophene, benzocarbazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenanthridineyl, phenanthridineyl Azinyl, phenthiazinyl, zazacarbazolyl, zazadibenzofuranyl, or zazadibenzothiophene: deuterium, -F, -Cl, -Br, -I, 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 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups; or Groups represented by formula 2A or formula 2B: Formula 2A Formula 2B in, In equations 2A and 2B, Y 21 -Y 24 Each is independently a single bond, O, S, N(R) 21 ), C(R 21 (R) 22 ), Si(R) 21 (R) 22 ), C(=O), S(=O), S(=O)2, B(R 21 ), P(R 21 ), or P(=O)(R 21 ), A 21 -A 23 Each of these groups can be independently a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group. R 21 and R 22 Each independently by reference to R in claim 1 10 or R 20 Based on the description, and * and *' each represent a binding site with an adjacent atom.
4. The organic light-emitting device as claimed in claim 1, wherein a10 is 0 or 1.
5. The organic light-emitting device as claimed in claim 1, wherein R 10 and R 20 Each of the following groups is independently hydrogen, deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by formulas 9-1 to 9-19, or a group represented by formulas 10-1 to 10-10, 10-13 to 10-41, and 10-49 to 10-211: in, In formulas 9-1 to 9-19 and 10-1 to 10-10, 10-13 to 10-41 and 10-49 to 10-211, * indicates a binding site with an adjacent atom, and "Ph" indicates phenyl.
6. The organic light-emitting device as claimed in claim 1, wherein R 10 and R 20 Each independently is: Hydrogen, deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, -F, cyano, phenyl, or naphthyl; Each of the C1-C segments is independently substituted by at least one of biphenyl or terphenyl groups. 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, or dibenzothiopheneyl; Each of the following groups is independently substituted by at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, or dibenzothiopheneyl; deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 alkylthio, phenyl, or naphthyl; or Each of the following biphenyl or terphenyl groups is independently substituted with at least one of the following: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
7. The organic light-emitting device as claimed in claim 1, wherein R 10 for: Deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, cyano, phenyl, or naphthyl; Each of the C1-C segments is independently substituted by at least one of biphenyl or terphenyl groups. 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phen Zinel or phenothiazinel; Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenyl Azine group, or phenothiazine group: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, carbazole, dibenzofuranyl, or dibenzothiophene; or Each of the following biphenyl or terphenyl groups is independently substituted with at least one of the following: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl, and R 20 It can be hydrogen, deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl or phenyl.
8. The organic light-emitting device as claimed in claim 1, wherein c10 is 1.
9. The organic light-emitting device of claim 1, wherein the silane compound represented by formula 1 is represented by one of formulas 10-1 to 10-5: in, In equations 10-1 to 10-5, Ar1-Ar3, L 10 a10 and R 10 Referring respectively to Ar1-Ar3 and L in claim 1 10 a10 and R 10 Based on the description, and R1-R9 are each independently obtained by referring to R in claim 1. 20 Understanding is based on the description.
10. The organic light-emitting device of claim 9, wherein the silane compound represented by formula 1 is a compound represented by formulas 10-5, and R 10 for: Deuterium, -F, cyano, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Each of the C1-Cs is independently replaced by at least one of the following: 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy groups: deuterium, cyano, phenyl, or naphthyl; Each of the C1-C segments is independently substituted by at least one of biphenyl or terphenyl groups. 20 Alkyl, C1-C 20 alkylthio or C1-C 20 Alkoxy; Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phen Zinel or phenothiazinel; Each of the following groups is independently substituted with at least one of the following: cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiopheneyl, phenyl Azine group, or phenothiazine group: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, carbazole, dibenzofuranyl, or dibenzothiophene; or Each of the following biphenyl or terphenyl groups is independently substituted with at least one of the following: deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, or naphthyl.
11. The organic light-emitting device of claim 1, wherein the silane compound represented by formula 1 satisfies equation 1: Equation 1 E(T1) < E(S1) < 2 × E(T1) Among them, In Equation 1, E(T1) represents the lowest excited triplet energy level of the silane compound, and E(S1) represents the lowest excited singlet energy level of the silane compound.
12. The organic light-emitting device of claim 1, wherein the silane compound represented by formula 1 satisfies equation 2: Equation 2 [ 2 × E(T1) ] - E(S1) < 1 electron volt in, In equation 2, E(T1) represents the lowest excited triplet energy level of the silane compound, and E(S1) represents the lowest excited singlet energy level of the silane compound.
13. The organic light-emitting device of claim 1, wherein the silane compound represented by formula 1 is one of compounds 1 to 34, 37, 38, 41, 42, 45, 46, 49 to 58, and 60 to 160: 。 14. The organic light-emitting device of claim 1, wherein the content of the host is greater than the content of the dopant.
15. The organic light-emitting device of claim 1, wherein the host is composed of the silane compound.
16. The organic light-emitting device of claim 1, wherein the ratio of the emission component emitted from the dopant is 80% or greater of the total emission component emitted from the emission layer.
17. The organic light-emitting device of claim 1, wherein the dopant is a fluorescent dopant.
18. The organic light-emitting device of claim 1, wherein the emitting layer emits blue light having a maximum emission wavelength in the range of 410 nm to 490 nm.
19. The organic light-emitting device of claim 1, wherein the first electrode is an anode and the second electrode is a cathode. The organic layer includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode. The hole transport region includes at least one of a hole injection layer, a hole transport layer, or an electron blocking layer, and The electron transport region includes at least one of a hole blocking layer, an electron transport layer, or an electron injection layer.
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