Organic light-emitting device
By using the combination of body and dopant under specific conditions in OLED, limiting reduction or oxidation in the emission layer, the problem of insufficient OLED life is solved, achieving longer service life and better performance.
Patent Information
- Application Number
- CN202210276122.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2018-01-11
- Filing Date
- 2018-01-16
- Publication Date
- 2025-08-05
- Estimated Expiration
- 2038-01-16
AI Technical Summary
There are shortcomings in existing OLEDs in terms of life and need to improve their service life.
By using a combination of host and dopant under specific conditions in OLED, including phosphorescence or fluorescent dopants, a certain potential and energy level relationship is met to limit reduction or oxidation in the emission layer, thereby reducing the generation of free radical species and extending device life.
Effectively prevent and/or minimize the generation of free radical species in the emission layer, extend the service life of OLED, reduce exciton quenching and electrochemical/photochemical degradation, and improve device performance.
Smart Images

Figure CN114824115B_ABST
Abstract
Description
[0001] This application is a divisional application of the invention application with the application date of January 16, 2018, Chinese application number 201810039080.X, and invention name “Organic Light-Emitting Device”.
[0002] Cross-reference to related applications
[0003] This application claims priority from Korean Patent Application No. 10-2017-0007033, filed on January 16, 2017, and Korean Patent Application No. 10-2018-0003976, filed on January 11, 2018, in the Korean Intellectual Property Office, and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field
[0004] The present disclosure relates to organic light emitting devices. Background Art
[0005] An organic light emitting device (OLED) is a self-emitting device that has a wide viewing angle, a high contrast ratio, a short response time, and excellent brightness, driving voltage, and response speed characteristics, and that produces full-color images.
[0006] A typical OLED includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emissive layer. A hole transport region may be disposed between the anode and the emissive layer, and an electron transport region may be disposed between the emissive layer and the cathode. Holes provided from the anode may move toward the emissive layer through the hole transport region, and electrons provided from the cathode may move toward the emissive layer through the electron transport region. Carriers such as holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.
[0007] Various types of organic light emitting devices are known. However, there is still a need for OLEDs with a long lifetime. Summary of the Invention
[0008] Provided is an organic light emitting device including a host and a dopant satisfying predetermined conditions to have a long lifetime.
[0009] Additional 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 presented embodiments.
[0010] According to an aspect of one embodiment, an organic light emitting device includes:
[0011] a first electrode;
[0012] a second electrode facing the first electrode; and
[0013] an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer,
[0014] wherein the emission layer comprises a host and a dopant,
[0015] 1) The dopant includes a phosphorescent dopant, and
[0016] i) Conditions 1, 2, 3 and 4 are all met;
[0017] ii) When conditions 1 and 4 are satisfied and at least one of conditions 2 and 3 is not satisfied, condition 5-1 is satisfied;
[0018] iii) when at least one of conditions 1 and 4 is not satisfied and conditions 2 and 3 are satisfied, condition 6-1 is satisfied; or
[0019] iv) When at least one of conditions 1 and 4 is not satisfied and at least one of conditions 2 and 3 is not satisfied, both conditions 5-1 and 6-1 are satisfied, or
[0020] 2) the dopant includes a fluorescent dopant, and
[0021] i) Conditions 1, 2, 3 and 4 are all met;
[0022] ii) when conditions 1 and 4 are satisfied and at least one of conditions 2 and 3 is not satisfied, condition 5-2 is satisfied;
[0023] iii) when at least one of conditions 1 and 4 is not satisfied and conditions 2 and 3 are satisfied, condition 6-2 is satisfied; or
[0024] iv) When at least one of conditions 1 and 4 is not satisfied and at least one of conditions 2 and 3 is not satisfied, both conditions 5-2 and 6-2 are satisfied:
[0025] Condition 1
[0026] E* 氧化,掺杂剂 ≥E 还原,主体
[0027] Condition 2
[0028] E* 还原,掺杂剂 ≤E 氧化,主体
[0029] Condition 3
[0030] E 氧化,掺杂剂 ≥E* 还原,主体
[0031] Condition 4
[0032] E 还原,掺杂剂 ≤E* 氧化,主体
[0033] Condition 5-1
[0034] T1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <T1 掺杂剂 +0.3eV
[0035] Condition 6-1
[0036] T1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <T1 掺杂剂 +0.3eV
[0037] Condition 5-2
[0038] S1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <S1 掺杂剂 +0.3eV
[0039] Condition 6-2
[0040] S1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <S1 掺杂剂 +0.3eV
[0041] Among them, "E* 氧化,掺杂剂 ” represents the excited state oxidation potential of the dopant (electron volt, eV),
[0042] “E* 还原,掺杂剂 ” represents the excited state reduction potential of the dopant (eV),
[0043] “E 氧化,掺杂剂 ” represents the ground state oxidation potential of the dopant (eV),
[0044] “E 还原,掺杂剂 ” represents the ground state reduction potential of the dopant (eV),
[0045] E* 还原,主体 ” represents the excited state reduction potential of the host (eV),
[0046] “E* 氧化,主体 ” represents the excited state oxidation potential of the host (eV),
[0047] “E 还原,主体 ” represents the ground state reduction potential of the host (eV),
[0048] “E氧化,主体 ” represents the ground state oxidation potential of the host (eV),
[0049] E* 氧化,掺杂剂 With E 氧化,掺杂剂 -T1 掺杂剂 equal,
[0050] E* 还原,掺杂剂 With E 还原,掺杂剂 +T1 掺杂剂 equal,
[0051] E* 氧化,主体 With E 氧化,主体 -S1 主体 equal,
[0052] E* 还原,主体 With E 还原,主体 +S1 主体 equal,
[0053] “T1 掺杂剂 ” represents the lowest triplet energy level of the dopant (eV),
[0054] “S1 掺杂剂 ” represents the lowest singlet energy level of the dopant (eV),
[0055] “S1 主体 ” represents the lowest singlet energy level of the host (eV),
[0056] E 氧化,掺杂剂 and E 氧化,主体 was measured using cyclic voltammetry (CV).
[0057] E 还原,掺杂剂 and E 还原,主体 was measured using differential pulse voltammetry.
[0058] T1 掺杂剂 and S1 掺杂剂 is calculated from the photoluminescence (PL) spectrum of the dopant in solution, and
[0059] S1 主体 is calculated from the PL spectrum of the host in solution,
[0060] Where "eV" stands for "electron volt". BRIEF DESCRIPTION OF THE DRAWINGS
[0061] By combining Figure 1 These and / or other aspects will become clearer and more readily understood from the following description of the embodiments considered. Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION
[0062] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following description of embodiments is merely to illustrate aspects of the present disclosure by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind) of...", when preceding or following a list of elements, modify the entire list of elements without modifying the individual elements of the list.
[0063] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
[0064] It will be understood that although the terms first, second, third, etc. may be used in this article to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings of the present embodiment, the first element, component, region, layer or part discussed below may be referred to as the second element, component, region, layer or part.
[0065] The terms used herein are for the purpose of describing specific embodiments only and are not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are also intended to include the plural forms, unless the context clearly indicates otherwise.
[0066] The term "or" means "and / or". It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.
[0067] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of this disclosure and the relevant art, and will not be interpreted in an idealized or exaggerated sense unless clearly defined as such herein.
[0068] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic representations of idealized embodiments. As such, deviations from the shapes of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Thus, the embodiments described herein should not be construed as limited to the specific shapes of the regions as shown herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Furthermore, sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shape of the regions and are not intended to limit the scope of the claims.
[0069] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurements in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within ±30%, 20%, 10%, 5%.
[0070] In an embodiment, an organic light emitting device is provided. The organic light emitting device may include:
[0071] a first electrode;
[0072] a second electrode facing the first electrode; and
[0073] an organic layer disposed between the first electrode and the second electrode,
[0074] wherein the organic layer includes an emission layer, and
[0075] The emission layer may include a host and a dopant.
[0076] In embodiments, the dopant may include a phosphorescent dopant. In some embodiments, the dopant may be a phosphorescent dopant.
[0077] In an organic light emitting device wherein the dopant comprises a phosphorescent dopant,
[0078] i) Conditions 1, 2, 3 and 4 can all be met;
[0079] ii) When conditions 1 and 4 are satisfied and at least one of conditions 2 and 3 is not satisfied, condition 5-1 may be satisfied;
[0080] iii) when at least one of conditions 1 and 4 may not be satisfied and conditions 2 and 3 are satisfied, condition 6-1 may be satisfied; or
[0081] iv) When at least one of conditions 1 and 4 may not be satisfied and at least one of conditions 2 and 3 may not be satisfied, conditions 5-1 and 6-1 may both be satisfied.
[0082] In one or more embodiments, the dopant may include a fluorescent dopant. In some embodiments, the dopant may be a fluorescent dopant.
[0083] In an organic light emitting device wherein the dopant comprises a fluorescent dopant,
[0084] i) Conditions 1, 2, 3 and 4 can all be met;
[0085] ii) When conditions 1 and 4 are satisfied and at least one of conditions 2 and 3 is not satisfied, condition 5-2 may be satisfied;
[0086] iii) when at least one of conditions 1 and 4 may not be satisfied and conditions 2 and 3 are satisfied, condition 6-2 may be satisfied; or
[0087] iv) When at least one of conditions 1 and 4 may not be satisfied and at least one of conditions 2 and 3 may not be satisfied, conditions 5-2 and 6-2 may both be satisfied.
[0088] Condition 1
[0089] E* 氧化,掺杂剂 ≥E 还原,主体
[0090] Condition 2
[0091] E* 还原,掺杂剂 ≤E 氧化,主体
[0092] Condition 3
[0093] E 氧化,掺杂剂 ≥E* 还原,主体
[0094] Condition 4
[0095] E 还原,掺杂剂 ≤E* 氧化,主体
[0096] Condition 5-1
[0097] T1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <T1 掺杂剂 +0.3eV
[0098] (For example, T1 掺杂剂 -0.3eV<|E 还原,主体 -E 氧化,掺杂剂 | <T1 掺杂剂 +0.3eV)
[0099] Condition 6-1
[0100] T1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <T1 掺杂剂 +0.3eV
[0101] (For example, T1 掺杂剂 -0.3eV<|E 还原,掺杂剂 -E 氧化,主体 | <T1 掺杂剂 +0.3eV)
[0102] Condition 5-2
[0103] S1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <S1 掺杂剂 +0.3eV
[0104] (For example, S1 掺杂剂 -0.3eV<|E 还原,主体 -E 氧化,掺杂剂 | <S1 掺杂剂 +0.3eV)
[0105] Condition 6-2
[0106] S1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <S1 掺杂剂 +0.3eV
[0107] (For example, S1 掺杂剂 -0.3eV<|E 还原,掺杂剂 -E 氧化,主体 | <S1 掺杂剂 +0.3eV),
[0108] Where "eV" stands for "electron volt".
[0109] In conditions 1 to 6-2, E* 氧化,掺杂剂 ” represents the excited state oxidation potential of the dopant (expressed in electron volts, eV),
[0110] “E* 还原,掺杂剂 ” represents the excited state reduction potential of the dopant (eV),
[0111] “E 氧化,掺杂剂 ” represents the ground state oxidation potential of the dopant (eV),
[0112] “E 还原,掺杂剂” represents the ground state reduction potential of the dopant (eV),
[0113] E* 还原,主体 ” represents the excited state reduction potential of the host (eV),
[0114] “E* 氧化,主体 ” represents the excited state oxidation potential of the host (eV),
[0115] “E 还原,主体 ” represents the ground state reduction potential of the host (eV),
[0116] “E 氧化,主体 ” represents the ground state oxidation potential of the host (eV),
[0117] E* 氧化,掺杂剂 Can be used with E 氧化,掺杂剂 -T1 掺杂剂 equal,
[0118] E* 还原,掺杂剂 Can be used with E 还原,掺杂剂 +T1 掺杂剂 equal,
[0119] E* 氧化,主体 Can be used with E 氧化,主体 -S1 主体 equal,
[0120] E* 还原,主体 Can be used with E 还原,主体 +S1 主体 equal,
[0121] “T1 掺杂剂 ” represents the lowest triplet energy level of the dopant (eV),
[0122] “S1 掺杂剂 ” represents the lowest singlet energy level of the dopant (eV),
[0123] “S1 主体 ” represents the lowest singlet energy level of the host (eV),
[0124] E 氧化,掺杂剂 and E 氧化,主体 It can be measured by using cyclic voltammetry (CV).
[0125] E 还原,掺杂剂 and E 还原,主体 It can be measured by using differential pulse voltammetry.
[0126] T1 掺杂剂 and S1 掺杂剂 can be calculated from the photoluminescence (PL) spectrum of the dopant in solution, and
[0127] S1主体 It can be calculated from the PL spectrum of the host in solution.
[0128] Although not wishing to be bound by theory, it is understood that when an organic light-emitting device satisfies conditions 1, 2, 3, and 4, the reduction or oxidation of the host and / or dopant in the emission layer by electron transfer can be substantially prevented, thereby substantially preventing the generation of free radical species in the emission layer. Since free radical species can cause various side reactions in the emission layer, the lifespan of the organic light-emitting device can be shortened.
[0129] In some embodiments, 1) when the dopant of the organic light-emitting device includes a phosphorescent dopant and at least one of conditions 5-1 and 6-1 is satisfied in the organic light-emitting device; or 2) when the dopant of the organic light-emitting device includes a fluorescent dopant and at least one of conditions 5-2 and 6-2 is satisfied in the organic light-emitting device, i) a limited (limited) degree of reduction or oxidation of the host and / or dopant in the emission layer by electron transfer may occur, and ii) even when reduction or oxidation of the host and / or dopant in the emission layer by electron transfer occurs, electron back transfer may occur quickly, which may promote the host and / or dopant to quickly return to their / its original state before the reduction or oxidation. Therefore, the reduction or oxidation of the host and / or dopant in the emission layer by electron transfer may be substantially prevented and / or limited, thereby substantially preventing and / or limiting the generation of free radical species in the emission layer. In addition, re-excitation of the dopant may also be promoted.
[0130] While not wishing to be bound by theory, it is understood that when an organic light-emitting device satisfies the aforementioned conditions, the generation of free radical species in the emission layer can be substantially prevented and / or minimized, and thus, exciton quenching in the emission layer of the organic light-emitting device and electrochemical and / or photochemical degradation of the host and dopant in the emission layer can be substantially prevented and / or minimized. Consequently, the organic light-emitting device can have an improved lifespan.
[0131] In one or more embodiments, the dopant of the organic light-emitting device may include a phosphorescent dopant, and in the organic light-emitting device, at least one of conditions 5-1 and 6-1 may be satisfied.
[0132] In one or more embodiments, the dopant of the organic light-emitting device may include a fluorescent dopant, and in the organic light-emitting device, at least one of conditions 5-2 and 6-2 may be satisfied.
[0133] In one or more embodiments, the dopant of the organic light emitting device may include a phosphorescent dopant, and in the organic light emitting device, conditions 1 and 3 may not be satisfied, and conditions 2, 4, 5-1, and 6-1 may be satisfied.
[0134] In one or more embodiments, the dopant of the organic light-emitting device may include a phosphorescent dopant, and in the organic light-emitting device, conditions 3 and 6-1 may not be satisfied, and conditions 1, 2, 4, and 5-1 may be satisfied.
[0135] i) the host may include (e.g., consist of) at least one donor compound, ii) the host may include (e.g., consist of) at least one acceptor compound, or iii) the host may include (e.g., consist of) a combination of at least one donor compound and at least one acceptor compound. When the host includes at least one donor compound and at least one acceptor compound, the donor compound and the acceptor compound may form an exciplex.
[0136] The donor compound may include at least one selected from the group consisting of a ring containing carbazole, a ring containing dibenzofuran, a ring containing dibenzothiophene, a ring containing indenocarbazole, a ring containing indolocarbazole, a ring containing benzofuranocarbazole, a ring containing benzothienocarbazole, a ring containing acridine, a ring containing dihydroacridine, and a ring containing tri-indoloacene, and
[0137] The acceptor compound may include at least one selected from the group consisting of a ring comprising carbazole, a ring comprising dibenzofuran, a ring comprising dibenzothiophene, a ring comprising indenocarbazole, a ring comprising indolocarbazole, a ring comprising benzofuranocarbazole, a ring comprising benzothiophenocarbazole, a ring comprising pyridine, a ring comprising pyrimidine, and a ring comprising triazine.
[0138] In some embodiments, the acceptor compound may include at least one electron withdrawing group,
[0139] The electron-withdrawing group may be selected from:
[0140] -F, -CFH2, -CF2H, -CF3, -CN, and -NO2;
[0141] C1-C substituted by at least one selected from -F, -CFH2, -CF2H, -CF3, -CN, and -NO2 60 alkyl;
[0142] Each of the C1-C 60 heteroaryl and monovalent non-aromatic fused polycyclic heterocyclic groups; and
[0143] Each includes *=N-*' as a ring-forming portion and each is substituted by at least one C1-C 60Heteroaryl and monovalent non-aromatic fused polycyclic heterocyclic groups: deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroaralkyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups.
[0144] In an embodiment, the donor compound may be selected from compounds represented by formula D-1, and
[0145] The receptor compound can be selected from compounds represented by formula A-1 and A-2:
[0146] Formula D-1
[0147] Ar1-(L1) a1 -Ar2
[0148] Formula A-1
[0149] Ar 11 -(L 11 ) a11 -Ar 12
[0150] Formula A-2
[0151]
[0152]
[0153] Wherein, in formulas D-1, A-1, A-2, and 11 to 14,
[0154] Ar1 may be a group represented by formula 11 and 12,
[0155] Ar2 can be selected from:
[0156] Groups represented by Formulas 11 and 12, a phenyl group, a naphthyl group, and a benzimidazolyl group; and
[0157] phenyl, naphthyl, and benzimidazolyl groups each selected from at least one substituted group consisting of deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl,
[0158] Ar 11 and Ar 12 Can be independently selected from the groups represented by formulae 13 and 14,
[0159] X1 can be N or C (T 14 ), X2 can be N or C(T 15 ), and X3 can be N or C (T 16 ), provided that at least one of X1-X3 is N,
[0160] L1 can be selected from:
[0161] a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and
[0162] phenylene, naphthylene, fluorenylene, carbazolylene, dibenzofuranylene, and dibenzothiophenylene, each of which is substituted by at least one selected from the group consisting of deuterium, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ), L 11 -L 13 Can be independently selected from:
[0163] a single bond, a phenylene group, a pyridylene group, a pyrimidylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and
[0164] each being at least one substituted phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, naphthylene, fluorenylene, carbazolylene, dibenzofuranylene, and dibenzothiophenylene group, each being selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ),
[0165] a1 and a11-a13 can each be independently selected from an integer of 0-5; when a1 is 2 or greater, at least two L1 groups can be the same or different from each other; when a11 is 2 or greater, at least two L 11 The groups may be the same or different from each other; when a12 is 2 or greater, at least two L 12 The groups may be the same as or different from each other; and when a13 is 2 or greater, at least two L 13 The groups may be identical to or different from each other,
[0166] CY1-CY4 can be each independently selected from a phenyl group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, and a dibenzothiophene group,
[0167] A1 can be selected from
[0168] single bonds, C1-C4 alkylene, and C2-C4 alkenylene; and
[0169] C1-C4 alkylene and C2-C4 alkenylene, each of which is selected from at least one substituted 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 21 )(Q 22 )(Q 23 ),
[0170] A2 can be selected from:
[0171] single bonds, C1-C4 alkylene, and C2-C4 alkenylene; and
[0172] each being at least one substituted C1-C4 alkylene group and C2-C4 alkenylene group selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 21 )(Q 22 )(Q 23 ),
[0173] R1, R 10 and R 20 Can be independently selected from:
[0174] hydrogen, deuterium, hydroxyl, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, and C1-C 20 alkoxy;
[0175] Each of the following is substituted by at least one C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0176] phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0177] phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, hydroxyl, amino, amidine, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothienyl; and
[0178] -Si(Q1)(Q2)(Q3),
[0179] T 11 -T 16 , R2, R 30 and R 40can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and -Si(Q1)(Q2)(Q3),
[0180] b1-b4 may each independently be an integer selected from 0-10, and
[0181] The substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C60 The heteroarylalkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 31 )(Q 32 )(Q 33 ),
[0182] Among them, Q1-Q3, Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 can be independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
[0183] In some embodiments, in formula D-1, Ar1 may be selected from groups represented by formulae 11-1 to 11-8 and 12-1 to 12-8,
[0184] In formula D-1, Ar2 may be selected from groups represented by formulas 11-1 to 11-8 and 12-1 to 12-8, a phenyl group, a naphthyl group, and a benzimidazolyl group substituted with a phenyl group, and
[0185] In formula A-1, Ar 11 and Ar 12 Each independently selected from the groups represented by the formulae 13-1 to 13-8 and 14-1 to 14-8:
[0186]
[0187]
[0188]
[0189]
[0190]
[0191] However, in Formulas 11-1 to 11-8, 12-1 to 12-8, 13-1 to 13-8, and 14-1 to 14-8,
[0192] X 11 and X 13 Can be each independently C(R 17 )(R 18 )、N(R 19 ), O, or S,
[0193] X 12 and X 14 Can be each independently C(R 37 )(R 38 )、N(R 39 ), O, or S,
[0194] R1, R2, A1 and A2 may be the same as those defined herein,
[0195] R 11 -R 19 This article can be compared with the R 10 The same definition,
[0196] R 21 -R 24 This article can be compared with the R 20 The same definition,
[0197] R 31 -R 39 This article can be compared with the R 30 The same definition,
[0198] R 41-R 44 This article can be compared with the R 40 The same definition as
[0199] * indicates the binding site with the adjacent atom.
[0200] In some embodiments, in Formulas 11, 12, 11-1 to 11-8, and 12-1 to 12-8, A1 may be selected from:
[0201] single bonds, C1-C2 alkylene, and C2 alkenylene; and
[0202] C1-C2 alkylene and C2 alkenylene, each of which is selected from at least one substituted 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 21 )(Q 22 )(Q 23 ),
[0203] In Formulas 13, 14, 13-1 to 13-8, and 14-1 to 14-8, A2 may be selected from:
[0204] single bonds, C1-C2 alkylene, and C2 alkenylene; and
[0205] each being selected from at least one substituted C1-C2 alkylene and C2 alkenylene group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 21 )(Q 22 )(Q 23 ),and
[0206] In Formulas 13, 14, 13-1 to 13-8, and 14-1 to 14-8, R2, R 30 to R 39 , and R 40 to R 44 Can be independently selected from:
[0207] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, and C1-C 20alkoxy;
[0208] Each of the following is substituted by at least one C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0209] phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0210] phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0211] -Si(Q1)(Q2)(Q3),
[0212] Among them, Q1-Q3 and Q 21 -Q 23 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, and naphthyl, but the embodiment is not limited thereto.
[0213] In an embodiment, in formula D-1, Ar1 may be selected from groups represented by formulae 15-1 to 15-17 and 16-1 to 16-8,
[0214] In formula D-1, Ar2 may be selected from groups represented by formulas 15-1 to 15-17 and 16-1 to 16-8, a phenyl group, a naphthyl group, and an imidazole group substituted with a phenyl group, and
[0215] In formula A-1, Ar 11 and Ar 12 Each independently selected from the groups represented by formulae 17-1 to 17-3, but the embodiment is not limited thereto:
[0216]
[0217]
[0218] In formulas 15-1 to 15-17, 16-1 to 16-18, and 17-1 to 17-3,
[0219] X 11 and X 13 Can be each independently C(R 17 )(R 18 )、N(R 19 ), O, or S,
[0220] R' and R" can be independently selected from hydrogen, deuterium, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl,
[0221] R1, R 10 、R 20 、R 30 and R 40 may be the same as those described herein, and
[0222] R 10a -R 10c This article can be compared with the R 10 The same definition.
[0223] In some embodiments, in Formulas 15-1 to 15-17, 16-1 to 16-18, and 17-1 to 17-3,
[0224] R1, R 10 、R 10a -R 10c and R 20 can be independently selected from hydrogen, deuterium, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q1)(Q2)(Q3), and
[0225] R 30 and R 40 Can be independently selected from:
[0226] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, C1-C 10 alkoxy, -CF3, -CF2H, and -CFH2;
[0227] phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0228] phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0229] -Si(Q1)(Q2)(Q3),
[0230] wherein Q1-Q3 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, and naphthyl, but the embodiment is not limited thereto.
[0231] In some embodiments,
[0232] i) The donor compound may be represented by formula D-1 wherein L1 is a single bond; or
[0233] ii) The donor compound may be selected from compounds represented by formulae D-1(1) to D-1(52):
[0234]
[0235]
[0236]
[0237] Wherein, in formulas D-1(1) to D-1(52),
[0238] Ar1 and Ar2 may be the same as those described herein,
[0239] Y 51 Can be C(Z 53 )(Z 54 )、N(Z 55 ), O, or S, and
[0240] Z 51 -Z 56 can be independently selected from hydrogen, deuterium, C1-C 10 Alkyl, C1-C10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ),
[0241] where Q 11 -Q 13 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, and naphthyl.
[0242] In some embodiments, in Formulas D-1(1) to D-1(52),
[0243] Ar1 may be selected from groups represented by formulae 11 and 12, and
[0244] Ar2 can be selected from:
[0245] Groups represented by Formulas 11 and 12, a phenyl group, a naphthyl group, and a benzimidazolyl group; and
[0246] phenyl, naphthyl, and benzimidazolyl groups each selected from at least one substituted group consisting of deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.
[0247] In one or more embodiments, in Formulas D-1(1) to D-1(52),
[0248] Ar1 may be selected from groups represented by the formulae 11-1 to 11-8 and 12-1 to 12-8,
[0249] Ar2 may be selected from groups represented by Formulas 11-1 to 11-8 and 12-1 to 12-8, a phenyl group, a naphthyl group, and a benzimidazolyl group substituted with a phenyl group, but the embodiment is not limited thereto.
[0250] In formulas A-1 and A-2, L 11 -L 13 can be independently selected from the groups represented by the formulae 3-1 to 3-56, and i) the number of L is a11 11 at least one of, ii) a12 number of L 12 at least one of, and iii) a13 number of L 13 At least one of the groups may be independently selected from the groups represented by the formulae 3-15 to 3-56:
[0251]
[0252]
[0253]
[0254] Among them, in formulas 3-1 to 3-56,
[0255] Y1 may be selected from O, S, C(Z3)(Z4), and N(Z5),
[0256] Z1-Z5 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ),
[0257] where Q 11 -Q 13 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, and
[0258] d4 can be an integer selected from 0-4,
[0259] d3 can be an integer selected from 0-3,
[0260] d2 may be an integer selected from 0-2, and
[0261] * and *' each represent a binding site with an adjacent atom.
[0262] In one or more embodiments, in Formulas A-1 and A-2, *-(L 11 ) a11 -*'、*-(L 12 ) a12 -*', and *-(L 13 ) a13 - The group represented by '*' can be selected from the groups represented by the formulae 4-1 to 4-39:
[0263]
[0264]
[0265]
[0266] Among them, in formulas 4-1 to 4-39,
[0267] X 21 Can be N or C(Z 21 ), X 22 Can be N or C(Z 22 ), X 23 Can be N or C(Z 23 ), X 24 Can be N or C(Z 24 ), X 31 Can be N or C(Z 31 ), X 32 Can be N or C(Z 32 ), X 33 Can be N or C(Z 33 ), X 34 Can be N or C(Z 34 ), X 41 Can be N or C(Z 41 ), X 42 Can be N or C(Z 42 ), X 43 Can be N or C(Z 43 ), and X 44 Can be N or C(Z 44 ), the condition is X 21 -X 24 At least one of them is not N, X 31 -X 34 At least one of them is not N, and X 41 -X 44 At least one of them is not N,
[0268] Z 21 -Z 24 , Z 31 -Z 34 , and Z 41 -Z 44 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11)(Q 12 )(Q 13 ),
[0269] where Q 11 -Q 13 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, and
[0270] * and *' each represent a binding site with an adjacent atom.
[0271] In formula A-2, T 11 -T 16 Can be independently selected from:
[0272] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, C1-C 10 alkoxy, -CF3, -CF2H, and -CFH2;
[0273] Each of the following is substituted by at least one C1-C 10 Alkyl and C1-C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, -CF3, -CF2H, and -CFH2;
[0274] phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0275] phenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0276] -Si(Q1)(Q2)(Q3),
[0277] wherein Q1-Q3 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.
[0278] In some embodiments, in Formula A-2, T 11 -T 16 Can be independently selected from:
[0279] Hydrogen, deuterium, -F, cyano, C1-C 10 Alkyl, C1-C 10 alkoxy, -CF3, -CF2H, and -CFH2;
[0280] Each of the following is substituted by at least one C1-C 10 Alkyl and C1-C 10 Alkoxy: deuterium, -F, cyano, -CF3, -CF2H, and -CFH2;
[0281] phenyl, pyridyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0282] phenyl, pyridyl, pyrimidyl, triazinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is substituted by at least one selected from the group consisting of deuterium, -F, cyano, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, pyridyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0283] -Si(Q1)(Q2)(Q3),
[0284] wherein Q1-Q3 can be independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, pyridyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.
[0285] In one or more embodiments,
[0286] i) The acceptor compound can be represented by the formula A-, wherein Ar 11 and Ar 12 are each independently selected from the groups represented by formulae 17-1 to 17-3, and Ar 11 and Ar 12 At least one selected from the group represented by formula 17-2 and 17-3;
[0287] ii) The receptor compound can be represented by formula A-1, wherein L 11 A group selected from the group represented by formula 3-15 and 3-28, and the number of L is a11 11 at least one selected from the groups represented by formulae 6-1 to 6-4; or
[0288] iii) The acceptor compound may be represented by Formula A-2, wherein X1 to X3 are each N, but the embodiment is not limited thereto.
[0289] In some embodiments, the donor compound may be selected from compounds D1 to D17, and the acceptor compound may be selected from compounds A1 to A11, but the embodiments are not limited thereto:
[0290]
[0291]
[0292]
[0293] The dopant in the emissive layer may include a phosphorescent dopant.
[0294] The phosphorescent dopant may be any suitable dopant capable of emitting light according to a phosphorescent emission mechanism.
[0295] The phosphorescent dopant may be selected from a red phosphorescent dopant, a green phosphorescent dopant, and a blue phosphorescent dopant.
[0296] In an embodiment, the phosphorescent dopant may be a green phosphorescent dopant or a blue phosphorescent dopant, but the embodiment is not limited thereto.
[0297] In some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 81:
[0298] Formula 81
[0299] M(L 81 ) n81 (L 82 ) n82
[0300] Formula 81A
[0301]
[0302] Wherein, in Formulas 81 and 81A,
[0303] M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh),
[0304] L81 It can be a ligand represented by formula 81A, and n81 can be an integer of 1-3; when n81 is 2 or greater, at least two L 81 The groups may be identical to or different from each other,
[0305] L 82 It can be an organic ligand, and n82 can be an integer from 0 to 4; when n82 is 2 or greater, at least two L 82 The groups may be identical to or different from each other,
[0306] Y 81 -Y 84 can each independently be C or N,
[0307] Y 81 and Y 82 Can be combined via single or double bonds, Y 83 and Y 84 Can be combined via single or double bonds,
[0308] CY 81 and CY 82 Can be independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic groups,
[0309] CY 81 and CY 82 optionally and additionally bound via an organic linking group,
[0310] R 81 -R 85 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid 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 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 81 )(Q 82 )(Q 83 )、-N(Q 84 )(Q 85 )、-B(Q 86 )(Q 87 ), and -P(=O)(Q 88 )(Q 89 ),
[0311] a81-a83 can each independently be an integer selected from 0-5,
[0312] When a81 is 2 or greater, at least two R 81 The groups may be identical to or different from each other,
[0313] When a82 is 2 or greater, at least two R 82 The groups may be identical to or different from each other,
[0314] When a81 is 2 or greater, adjacent R 81 The groups may optionally be combined to form a saturated or unsaturated ring,
[0315] When a82 is 2 or greater, adjacent R 82 The groups may optionally be combined to form a saturated or unsaturated ring,
[0316] In Formula 81A, * and *' each represent a binding site with M in Formula 81, and
[0317] The substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 The heteroarylalkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 91 )(Q 92 )(Q 93 ),
[0318] where Q 81 -Q 89 and Q 91 -Q 93 can be independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
[0319] In an embodiment, in Formula 81A,
[0320] a83 can be 1 or 2, and
[0321] R 83 -R 85 Can be independently selected from:
[0322] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;
[0323] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and
[0324] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl, each of which is selected from at least one substituted group consisting of deuterium, C1-C 10 an alkyl group, and a phenyl group, but the embodiment is not limited thereto.
[0325] In one or more embodiments, in Formula 81A,
[0326] Y 81 Can be N, Y 82 and Y 83 Can be C, Y 84 can be N or C, and
[0327] CY 81 and CY 82 Each of the cyclopentadiene groups, phenyl groups, heptalene groups, indene groups, naphthalene groups, azulene groups, indacene groups, acenaphthene groups, fluorene groups, spiro-bifluorene groups, benzofluorene groups, dibenzofluorene groups, phenanthene groups, phenanthren groups, anthracene groups, fluoranthene groups, benzo[9,10]phenanthrene groups, pyrene groups, group, naphthalene group, perylene group, pentacene group, hexacenyl group, ruby density group, coronene group, ovophenyl group, pyrrole group, isoindole group, indole group, indazole group, pyrazole group, imidazole group, triazole group, Azole group, iso Azole group, a oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzo Azole group, isobenzo oxazole group, benzocarbazole group, dibenzocarbazole group, imidazopyridine group, imidazopyrimidine group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, 2,3-dihydro-1H-imidazole group, and 2,3-dihydro-1H-imidazopyrazine group.
[0328] In one or more embodiments, in Formula 81A, Y 81 Can be N, Y 82 -Y 84 Can be C, CY 81 can be selected from a 5-membered ring including two N atoms as ring atoms, and CY 82 The group may be selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group, but the embodiment is not limited thereto.
[0329] In one or more embodiments, in Formula 81A, Y 81 Can be N, Y 82 -Y 84 Can be C, CY 81 can be an imidazole group or a 2,3-dihydro-1H-imidazole group, and CY 82 The group may be selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group, but the embodiment is not limited thereto.
[0330] In one or more embodiments, in Formula 81A,
[0331] Y 81 Can be N, Y 82 -Y 84 Can each be C,
[0332] CY 81 Can be selected from pyrrole group, pyrazole group, imidazole group, triazole group, Azole group, iso Azole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, pyridine group, pyrimidine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, benzimidazole group, isobenzothiazole group, benzo Azole groups, and isobenzo an azole group, and
[0333] CY 82 It can be selected from cyclopentadiene group, benzene group, naphthalene group, fluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, benzo[9,10]phenanthrene group, pyrene group, group, a perylene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, and a dibenzosilole group.
[0334] In one or more embodiments, in Formula 81A, Y 81 、Y 83 and Y 84 Can be C, Y 82 Can be N, CY 81 can be selected from a) a fused ring wherein i) a 5-membered ring including at least one N as a ring atom is fused to ii) a 6-membered ring selected from a phenyl group, a pyridine group, a pyrazine group, a pyrimidine group, and a pyridazine group; and b) a 5-membered ring including at least one N as a ring atom, and CY 82 It may be selected from a phenyl group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, a pyridine group, a pyrimidine group, a quinoline group, and an isoquinoline group, but the embodiment is not limited thereto.
[0335] In one or more embodiments, in Formula 81A,
[0336] R 81 and R 82 Can be independently selected from:
[0337] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 Alkyl, and C1-C 20 alkoxy;
[0338] Each of the following is substituted by at least one C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;
[0339] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl;
[0340] each being selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, and imidazopyrimidyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; and
[0341] -B(Q 86 )(Q 87 ) and -P(=O)(Q 88 )(Q 89 ),
[0342] where Q 86 -Q 89 Can be independently selected from:
[0343] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;
[0344] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and
[0345] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl, each of which is selected from at least one substituted group consisting of deuterium, C1-C 10 Alkyl, and phenyl.
[0346] In one or more embodiments, in Formula 81A, R 81 and R 82 Can be independently selected from
[0347] hydrogen, deuterium, -F, cyano, nitro, -SF5, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, dibenzothiophenyl, and dibenzofuranyl;
[0348] each selected from at least one substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, methoxy alkyl, ethoxy, propoxy, butoxy, pentyloxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, dibenzothiophenyl, and dibenzofuranyl: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 10 Alkyl, C1-C 10 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, dibenzothienyl, and dibenzofuranyl; and
[0349] -B(Q 86 )(Q 87 ) and -P(=O)(Q 88 )(Q 89 ),
[0350] where Q 86 -Q 89 Can be independently selected from:
[0351] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;
[0352] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and
[0353] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl, each of which is selected from at least one substituted group consisting of deuterium, C1-C 10 Alkyl, and phenyl.
[0354] In one or more embodiments, in Formula 81A, the number of R is a81 81 At least one R with a quantity of a82 82 At least one of them, or any combination thereof may be a cyano group.
[0355] In one or more embodiments, in Formula 81A, Y 81 Can be N; Y 82 -Y 84 Can be C; CY 81 Can be an imidazole group or a 2,3-dihydro-1H-imidazole group; CY 82 can be selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group; and a number of R 81 At least one R with a quantity of a82 82 At least one of them, or any combination thereof may be a cyano group.
[0356] In one or more embodiments, in Formula 81A, the number of R is a82 82 At least one of may be a cyano group.
[0357] In one or more embodiments, in Formula 81A, the number of R is a81 81 At least one R with a quantity of a82 82 At least one of, or any combination thereof, may be deuterium.
[0358] In one or more embodiments, in Formula 81A, CY 81 and CY 82 Can additionally be bonded via an organic linking group. Examples of organic linking groups may include C2-C5 alkylene, C2-C5 alkenylene, By at least one R 81a Substituted C2-C5 alkylene, substituted by at least one R 81a substituted C2-C5 alkenylene, and substituted by at least one R 81a Replaced However, the implementation is not limited thereto. 81a This article can be compared with the R 81 Same as described.
[0359] In some embodiments, in Formula 81, L 81 The ligands represented by the free formulas 81A-1 to 81A-8 may be selected, but the embodiment is not limited thereto:
[0360]
[0361] Wherein, in Formulas 81A-1 to 81A-8,
[0362] CY 82 、R 82 , a82, * and *' may be the same as those described herein, and
[0363] R 81a 、R 81b and R 81c Each of them can be compared with the R 81 Same as described.
[0364] In some embodiments, in Formulas 81A-1 to 81A-8, at least one of the following may each be a cyano group: R 81a 、R 81b 、R 81c and R with a quantity of a82 82 , but the implementation is not limited thereto.
[0365] In one or more embodiments, in Formula 81, L 82 The ligands represented by the free formulae 3-1(1) to 3-1(60), 3-1(61) 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) can be selected:
[0366]
[0367]
[0368]
[0369]
[0370]
[0371]
[0372] Wherein, in Formulas 3-1(1) to 3-1(60), 3-1(61) 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),
[0373] X1 can be O, S, C (Z 21 )(Z 22 ), or N(Z 23 ),
[0374] X 31 Can be N or C(Z 1a ), X 32 Can be N or C(Z 1b ),
[0375] X 41 Can be O, S, N (Z 1a ), or C(Z 1a )(Z 1b ),
[0376] Z1-Z4, Z 1a , Z 1b , Z 1c , Z 1d , Z 2a , Z 2b , Z 2c , Z 2d , Z 11 -Z 14 , and Z 21 -Z 23 Can be independently selected from
[0377] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 Alkyl, and C1-C 20 alkoxy;
[0378] Each of the following is substituted by at least one C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;
[0379] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl;
[0380] each being selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, and imidazopyrimidyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; and
[0381] -B(Q 86 )(Q 87 ) and -P(=O)(Q 88 )(Q 89 ),
[0382] where Q 86 -Q 89 Can be independently selected from
[0383] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2;
[0384] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and
[0385] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl, each of which is selected from at least one substituted group consisting of deuterium, C1-C 10 Alkyl, and phenyl,
[0386] d2 and e2 can each independently be an integer selected from 0-4,
[0387] e3 can be an integer selected from 0-3,
[0388] d4 and e4 can each independently be an integer selected from 0-4,
[0389] d6 and e6 can each independently be an integer selected from 0-6,
[0390] d8 and e8 may each independently be an integer selected from 0-8, and
[0391] * and *' each represent a binding site to M in Formula 1.
[0392] In one or more embodiments, in Formula 81, M may be Ir, and the sum of n81 and n82 may be 3. In one or more embodiments, in Formula 81, M may be Pt, and the sum of n81 and n82 may be 2.
[0393] In one or more embodiments, the organometallic compound represented by Formula 81 may be neutral and may not include an ion pair of a cation and an anion.
[0394] In one or more embodiments, in Formula 81A,
[0395] Y 81 Can be N,
[0396] Y 82 -Y 84 Can be N,
[0397] CY 81 may be an imidazole group, and
[0398] CY 82 It may be a phenyl group, but the embodiment is not limited thereto.
[0399] In one or more embodiments, in Formulas 81 and 81A,
[0400] M can be Ir,
[0401] n81 can be 2 or 3,
[0402] a81 and a82 can each independently be an integer from 0 to 3,
[0403] a83 can be 0,
[0404] R 81 Can be selected from
[0405] C1-C 10 Alkyl and phenyl; and
[0406] Each is selected from deuterium and C1-C 10 At least one substituted C1-C 10 Alkyl and phenyl, and
[0407] R with quantity a82 82At least one of may be a cyano group, but the embodiment is not limited thereto.
[0408] In one or more embodiments, the dopant in the emission layer may include at least one selected from compounds PD1 to PD83 and PD85 to PD116, but embodiments are not limited thereto.
[0409]
[0410]
[0411]
[0412]
[0413]
[0414]
[0415]
[0416]
[0417]
[0418] The amount of the dopant in the emission layer may generally be in the range of about 0.01 parts by weight to about 20 parts by weight based on 100 parts by weight of the emission layer, but embodiments are not limited thereto. Although 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.
[0419] Figure 1 A schematic diagram illustrating an organic light emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device and a method of manufacturing the same according to one or more embodiments are described. The organic light emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially stacked in the order stated.
[0420] A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.
[0421] The first electrode 11 can be formed by vacuum depositing or sputtering the material for forming the first electrode 11 onto a substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from a material having a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2) and zinc oxide (ZnO). In some embodiments, the material for forming the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
[0422] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto.
[0423] The organic layer 15 may be on the first electrode 11 .
[0424] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
[0425] The hole transport region may be provided between the first electrode 11 and the emission layer.
[0426] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.
[0427] The hole transport region may include only a hole injection layer or only a hole transport layer. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer sequentially stacked on the first electrode 11. In some embodiments, 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.
[0428] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
[0429] When the hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be performed at a deposition temperature in the range of about 100° C. to about 500° C., at a temperature of about 100° C. to about 500° C., or at a temperature of about 100° C. to about 500° C. -8 Torr - about 10 -3 Under vacuum pressure in the Torr range, and The deposition is performed at a deposition rate within a range of 100 Å to 200 Å, 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 conditions for vacuum deposition are not limited thereto.
[0430] When the hole injection layer is formed by spin coating, the spin coating can be performed at a coating rate in the range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a temperature in the range of about 80° C. to 200° C. to facilitate removal of the solvent after spin coating, although the conditions may vary depending on the compound used as the hole injection material and the desired structure and thermal properties of the hole injection layer; but the conditions for spin coating are not limited thereto.
[0431] 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.
[0432] The hole transport region may include at least one selected from the group consisting of 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-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, and a compound represented by the following Formula 202:
[0433]
[0434] Formula 201
[0435]
[0436] Formula 202
[0437]
[0438] Wherein, in formula 201, Ar 101 and Ar 102 Can be independently selected from
[0439] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... benzo[9,10]phenanthrenylene, pyrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phen phenylene, tetraphenylene, perylenene, and pentacene; and
[0440] Each of the following is selected from at least one substituted phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthenylene, fluor ...benzo[9,10]phenanthrenylene, pyrenylene, acenaphthenylene, fluorenylene, phenanthrenylene, phenanthrenylene, fluorenylene, benzo[9,10]phenanthrenyl phenylene, tetraphenylene, perylenene, and pentacene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 heteroaralkyl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
[0441] In Formula 201, xa and xb may each independently be an integer of 0 to 5. In some embodiments, xa and xb may each independently be an integer of 0, 1, or 2. In some embodiments, xa may be 1 and xb may be 0, but the embodiment is not limited thereto.
[0442] In Equations 201 and 202, R 101 -R 108 、R 111 -R 119 , and R 121 -R 124 Can be independently selected from
[0443] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), and C1-C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy);
[0444] Each of the following is substituted by at least one C1-C 10 Alkyl and C1-C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, and phosphoric acid or its salt;
[0445] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl; and
[0446] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 Alkyl, and C1-C 10 An alkoxy group, but the embodiment is not limited thereto.
[0447] In formula 201, R 109 Can be selected from
[0448] phenyl, naphthyl, anthracenyl, and pyridyl; and
[0449] phenyl, naphthyl, anthracenyl, and pyridyl groups, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, anthracenyl, and pyridyl.
[0450] In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:
[0451] Formula 201A
[0452]
[0453] Among them, R in Formula 201A 101 、R 111 、R 112 , and R 109 May be the same as those described above.
[0454] In some embodiments, the compounds represented by Formulae 201 and 202 may include compounds HT1 to HT20, but embodiments are not limited thereto:
[0455]
[0456]
[0457]
[0458] The thickness of the hole transport region can be and in some embodiments When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer may be and in some embodiments The thickness of the hole transport layer can be within the range of and in some embodiments While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics can be obtained without a significant increase in driving voltage.
[0459] In addition to the aforementioned materials, the hole transport region may also include a charge generating material to improve the conductive properties of the hole transport region. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.
[0460] The charge generating material may include, for example, a p-dopant. The p-dopant may include one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano group-containing compounds such as compound HT-D1 or compound HP-1, but the embodiment is not limited thereto:
[0461]
[0462]
[0463] HP-1
[0464]
[0465] The hole transport region may further include a buffer layer.
[0466] The buffer layer may compensate for an optical resonance distance depending on the wavelength of light emitted from the emission layer to improve efficiency of the organic light emitting device.
[0467] The hole transport region may further include an electron blocking layer. The electron blocking layer may include any suitable known material such as mCP, but the embodiment is not limited thereto:
[0468]
[0469] In some embodiments, a donor compound included in the emission layer may be used as a material for forming the electron blocking layer.
[0470] The emission layer may be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, the vacuum deposition and coating conditions for forming the emission layer may be generally similar to those for forming the hole injection layer, although the conditions may vary depending on the compound used.
[0471] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In some embodiments, the emission layer may have a structure in which the red emission layer, the green emission layer, and / or the blue emission layer are stacked to emit white light. In some embodiments, the structure of the emission layer may be varied.
[0472] The emission layer may include a host and a dopant that may satisfy the above conditions.
[0473] In one or more embodiments, the emission layer may be composed of a host and a dopant that may satisfy the above conditions.
[0474] The thickness of the emission layer can be and in some embodiments While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within any of these ranges, improved light emitting characteristics may be obtained without a significant increase in driving voltage.
[0475] Next, an electron transport region may be formed on the emission layer.
[0476] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.
[0477] 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 embodiments are not limited thereto. The electron transport layer may have a single layer structure or a multilayer structure including two or more different materials.
[0478] 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.
[0479] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but embodiments are not limited thereto.
[0480]
[0481] In some embodiments, the acceptor compound used in the emission layer may be used as a material for forming the hole blocking layer.
[0482] The thickness of the hole blocking layer can be and in some embodiments While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.
[0483] The electron transport layer may further include at least one selected from BCP, BPhen, Alq3, BAlq, TAZ, and NTAZ:
[0484]
[0485] In some embodiments, the electron transport material in the electron transport layer may include a compound represented by Formula 40 or a compound represented by Formula 41:
[0486] Formula 40
[0487]
[0488] Formula 41
[0489]
[0490] Wherein, in equations 40 and 41,
[0491] L 41 and L 42 Can be independently selected from
[0492] C6-C 60 Arylene, C1-C 60 heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups; and
[0493] Each of the following is substituted by at least one C6-C 60 Arylene, C1-C 60 Heteroarylene, divalent non-aromatic fused polycyclic group, and divalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenanthrenyl, pyridinyl, pyrimidinyl, and triazinyl,
[0494] a41 and a42 can each independently be an integer from 0 to 5,
[0495] Ar 41 and Ar 42 Can be independently selected from
[0496] C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0497] Each of the following is substituted by at least one C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenyl, phenanthrenyl, pyridinyl, pyrimidinyl, and triazinyl, and
[0498] R 41 and R 42 Can be independently selected from
[0499] Benzimidazole, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyridinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, phenyl, naphthyl, pyrenyl, 1-Hydroxy, ...
[0500] Each of which is selected from at least one substituted benzimidazolyl, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyridinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, phenyl, naphthyl, pyrenyl, , fluorenyl, and phenanthrenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, benzimidazolyl, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyridinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, phenyl, naphthyl, pyrenyl, 1-Hydroxy, ...
[0501] In Equations 40 and 41, L 41 and L 42 This article can be compared with the L 11 Same as described.
[0502] In some embodiments, the electron transport material in the electron transport layer may include a compound represented by Formula 42:
[0503] Formula 42
[0504]
[0505] Wherein, in formula 42,
[0506] T1 can be N or C (R 201 ), T2 can be N or C(R 202 ), T3 can be N or C(R 203 ), provided that at least one of T1-T3 is N,
[0507] R 201 -R 203 Can be independently selected from
[0508] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0509] Each of the following is substituted by at least one C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenyl, phenanthrenyl, pyridinyl, pyrimidinyl, and triazinyl, and
[0510] Ar 201 -Ar 203 Can be independently selected from
[0511] C6-C 60 Arylene, C1-C60 heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups; and
[0512] Each of the following is substituted by at least one C6-C 60 Arylene, C1-C 60 Heteroarylene, divalent non-aromatic fused polycyclic group, and divalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenanthrenyl, pyridinyl, pyrimidinyl, and triazinyl,
[0513] p, q and r can each independently be 0, 1 or 2, and
[0514] Ar 211 and Ar 213 Can be independently selected from
[0515] C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0516] Each of the following is substituted by at least one C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenyl, phenanthrenyl, pyridinyl, pyrimidinyl, and triazinyl.
[0517] In an embodiment, in Formula 42, at least two of T1-T3 may be N.
[0518] In one or more embodiments, in Formula 42, T1-T3 may each be N.
[0519] In formula 42, Ar 201 -Ar 203 Can be independently selected from
[0520] phenylene, naphthylene, anthracenylene, pyrenylene, fluorenylene, benzo[9,10]phenanthrenylene, pyridylene, and pyrimidylene; and
[0521] Each of at least one substituted phenylene, naphthylene, anthracenylene, pyrenylene, fluorenylene, benzo[9,10]phenanthrenylene, pyridylene, and pyrimidylene groups is selected from the group consisting of phenyl, naphthyl, anthracenyl, pyrenyl, fluorenyl, benzo[9,10]phenanthrenyl, pyridylene, and pyrimidylene, but the embodiment is not limited thereto.
[0522] In Formula 42, p, q, and r may each independently be 0, 1, or 2. In some embodiments, in Formula 42, p, q, and r may each independently be 0 or 1, but embodiments are not limited thereto.
[0523] In formula 42, Ar 211 -Ar 213 Can be independently selected from
[0524] Phenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, phenanthrenyl, benzimidazolyl, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, and triazinyl; and
[0525] Each of which is substituted by at least one phenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, phenanthrenyl, benzimidazolyl, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, pyridyl, pyrimidinyl, pyrazinyl, and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenyl, phenanthrenyl, pyridyl, pyrimidinyl, and triazinyl, but the embodiment is not limited thereto.
[0526] In an embodiment, in Formula 42, is selected from Ar 211 -Ar 213 At least one of can be independently selected from
[0527] Benzimidazole, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, and triazinyl; and
[0528] Each of which is selected from at least one substituted benzimidazolyl, benzo oxazolyl, benzothiazolyl, benzopyrimidinyl, imidazopyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, pyridyl, pyrimidinyl, pyrazinyl, and triazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyrenyl, phenyl, phenanthrenyl, pyridyl, pyrimidinyl, and triazinyl, but the embodiment is not limited thereto.
[0529] In one or more embodiments, in Formula 20A, selected from Ar 211 -Ar 213 At least one of may be a substituted or unsubstituted phenanthrenyl group.
[0530] In some embodiments, the electron transport layer may include at least one selected from compounds ET1 to ET17, but embodiments are not limited thereto:
[0531]
[0532]
[0533]
[0534] The thickness of the electron transport layer can be and in some embodiments While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a significant increase in driving voltage.
[0535] The electron transport layer may further include a material including a metal in addition to the above-mentioned materials.
[0536] The metal-containing material may include a lithium (Li) complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or compound ET-D2:
[0537]
[0538] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19 .
[0539] The electron injection layer may include at least one selected from the group consisting of LiF, NaCl, CsF, Li2O, and BaO.
[0540] The thickness of the electron injection layer can be For example 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 electron injection characteristics can be obtained without a significant increase in driving voltage.
[0541] The second electrode 19 may be formed 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 having a relatively low work function, such as a metal, an alloy, a conductive compound, and a mixture thereof. Examples of materials for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In some embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top-emitting light-emitting device. In some embodiments, the material used to form the second electrode 19 may vary.
[0542] In the above, reference has been made to Figure 1 The organic light emitting device 10 is described, but the embodiment is not limited thereto.
[0543] As used herein, the term "C1-C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C1-C 60 "Alkylene" refers to a group having a C1-C 60 Alkyl groups are divalent groups of substantially the same structure.
[0544] As used herein, the term "C1-C 60 "Alkoxy" refers to a 101 (where A 101 C1-C 60 Examples thereof include methoxy, ethoxy and isopropoxy.
[0545] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 The alkyl group includes at least one carbon-carbon double bond in the middle or at the end. Examples include vinyl, propenyl and butenyl. As used herein, the term "C2-C 60 "Alkenylene" refers to a group having a C2-C 60 Alkenyl is a divalent group of substantially the same structure.
[0546] As used herein, the term "C2-C 60"Alkynyl" refers to a C2-C 60 The alkyl group includes at least one carbon-carbon triple bond in the middle or at the end. Examples include ethynyl and propynyl. As used herein, the term "C2-C 60 "Alkynylidene" refers to a C2-C 60 Alkynyl is a divalent group of substantially the same structure.
[0547] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms. Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 Cycloalkyl is a divalent group of substantially the same structure.
[0548] As used herein, the term "C1-C 10 "Heterocycloalkyl" refers to a saturated monovalent monocyclic group including at least one heteroatom selected from N, O, P, Si and S as a ring atom and 1 to 10 carbon atoms. Examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkylene" refers to a 10 Heterocycloalkyl is a divalent group of substantially the same structure.
[0549] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent monocyclic hydrocarbon group comprising 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole is non-aromatic (non-aromatic). Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a group having a C3-C 10 Cycloalkenyl is a divalent group of substantially the same structure.
[0550] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent monocyclic group comprising at least one heteroatom selected from N, O, P, Si and S as a ring atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 10 Examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 10 "Heterocycloalkenylene" refers to a group having a C1-C 10 Heterocycloalkenyl is a divalent group of substantially the same structure.
[0551] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. As used herein, the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl and When C6-C 60 Aryl and C6-C 60 When the arylene groups each include at least two rings, the at least two rings may be fused.
[0552] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si and S as a ring atom and 1 to 60 carbon atoms. The term "C1-C 60 "Heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si and S as a ring atom and 1 to 60 carbon atoms. 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 60 Heteroaryl and C1-C 60 When the heteroarylene groups each include at least two rings, the at least two rings may be fused.
[0553] As used herein, the term "C6-C 60 "Aryloxy" refers to a group consisting of -OA 102 (where A 102 C6-C 60 aryl) and the term "C7-C 60 Aralkyl" means -A 104 A 105 (where A 105 C6-C 59 Aryl and A 104 C1-C 53 As used herein, the term "C6-C 60 "Arylthio" refers to -SA 103 (where A 103 C6-C 60 A group represented by an aryl group.
[0554] As used herein, the term "C1-C 60 "Heteroaryloxy" refers to -OA106 (where A 106 C1-C 60 heteroaryl), and as used herein, the term "C1-C 60 "Heteroarylthio" means -SA 107 (where A 107 C1-C 60 heteroaryl).
[0555] As used herein, the term "C2-C 60 "Heteroaralkyl" refers to -A 108 A 109 (A 109 C1-C 59 Heteroaryl, and A 108 C1-C 59 alkylene).
[0556] As used herein, the term "monovalent non-aromatic 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 ring atoms, wherein the molecular structure as a whole is non-aromatic. Examples of non-aromatic fused polycyclic groups include fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.
[0557] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having at least two fused rings and having heteroatoms selected from N, O, P, Si and carbon atoms (for example, the number of carbon atoms may be in the range of 2-60) as ring atoms, wherein the molecular structure as a whole is non-aromatic. Examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0558] The substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocycloalkylene, substituted C3-C 10 Cycloalkenylene, substituted C1-C 10 Heterocycloalkenylene, substituted C6-C 60 Arylene, substituted C1-C 60 Heteroarylene, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused heteropolycyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 At least one substituent of the heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:
[0559] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 alkoxy;
[0560] Each of the following is substituted by at least one C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11)(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 ), and -B(Q 16 )(Q 17 );
[0561] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 a heteroaralkyl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;
[0562] Each of the following is substituted by at least one C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ), and -B(Q 26 )(Q 27 );or
[0563] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 ), or -B(Q 36 )(Q 37 ),
[0564] Among them, Q1-Q7, Q 11 -Q 17 , Q 21 -Q 27 , and Q 31 -Q 37 can be independently hydrogen, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 heteroaralkyl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.
[0565] The term "room temperature" as used herein refers to a temperature of about 25°C.
[0566] Hereinafter, the compound and the organic light-emitting device according to the embodiment will be described in detail with reference to 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 that the amount of B used is equal to the amount of A used in terms of molar equivalents.
[0567] Example
[0568] Evaluation Example 1
[0569] Referring to the method shown in Table 1, T1, S1, E 氧化 、E* 氧化 、E 还原 and E* 还原 The results are shown in Table 2.
[0570] Refer to Table 2, the E* of compounds PD7 to PD84 and PD300 to PD303 氧化 The value is equal to the E 氧化 -T1 value. E* of compound A2 氧化 The value is equal to E of compound A2 氧化 -S1 value. E* of compounds PD79 to PD84 and PD300 to PD303 还原 The value is equal to the E 还原 + T1 value. E* of compound A2 还原 The value is equal to E of compound A2 还原 +The value of S1.
[0571] Table 1
[0572]
[0573]
[0574] Table 2
[0575]
[0576]
[0577] Based on Table 2, it was determined whether or not conditions 1, 2, 3, 4, 5-1, and 6-1 were satisfied in combinations 1 to 10. The results are shown in Tables 3 and 4.
[0578] Table 3
[0579] Combination number main body dopant Condition 1 Condition 2 Condition 3 Condition 4 Combination 1 A2 PD79 X O X O Combination 2 A2 PD80 X O X O Combination 3 A2 PD81 O O X O Combination 4 A2 PD82 X N / A X N / A Combination 5 A2 PD83 X N / A X N / A Combination 6 A2 PD84 X X X X Combination 7 A2 PD300 O X O X Combination 8 A2 PD301 X X X X Combination 9 A2 PD302 X X X X Combination 10 A2 PD303 O X O X
[0580] Table 4
[0581]
[0582] "O" indicates that the combination meets the stated conditions.
[0583] "X" indicates that the combination does not meet the stated conditions.
[0584] "N / A" indicates that no evaluation could be performed because measurement results were not available.
[0585] Example 1
[0586] As the anode, a glass substrate with an ITO electrode thereon was cut into a size of 50 millimeters (mm) × 50 mm × 0.5 mm. The glass substrate was then ultrasonicated in acetone, isopropyl alcohol, and pure water for approximately 15 minutes in each solvent and cleaned by exposure to ultraviolet light and ozone for 30 minutes.
[0587] Compound HT3 and HP-1 (wherein the concentration of compound HP-1 is 3 weight % (wt %)) are co-deposited on the anode to form a The hole injection layer is formed by depositing compound HT3 on the hole injection layer to form a hole transport layer. The mCP is deposited on the hole transport layer to form a hole transport layer having a thickness of An electron blocking layer having a thickness of The thickness of the hole transport region.
[0588] Compound A2 (as a host) and compound PD79 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 9:1, thereby forming a The thickness of the emission layer.
[0589] Compound A4 was vacuum deposited on the emission layer to form a Compound ET17 and LiQ were co-deposited on the hole blocking layer at a weight ratio of 5:5 to form a hole blocking layer having a thickness of LiQ is deposited on the electron transport layer to form an electron transport layer having a thickness of Aluminum (Al) is deposited on the electron injection layer to form an electron injection layer having a thickness of An aluminum layer with a thickness of , thereby completing the manufacture of the organic light-emitting device.
[0590] Examples 2 and 3 and Comparative Examples 1 to 3
[0591] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the host and the dopant PD80, PD81, PD84, PD301, or PD302 shown in Table 5 were used in the formation of the emission layer.
[0592] Evaluation Example 2
[0593] The relative lifetimes (T 95 ) characteristics. The evaluation results are shown in Table 5. In Table 5, the relative life (T 95 ) represents lifespan data evaluating the time taken for the luminance (at 500 nits) to reach 95% relative to the initial luminance of 100%.
[0594] Table 5
[0595]
[0596]
[0597] Referring to the results of Table 5, it was found that the organic light emitting devices of Examples 1 to 3 had long lifespan characteristics compared with the organic light emitting devices of Comparative Examples 1 to 3.
[0598] As apparent from the foregoing description, the organic light emitting device according to one or more embodiments may include a host and a dopant satisfying the foregoing conditions to have a long lifespan.
[0599] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
[0600] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the disclosure as defined by the following claims.
Claims
1. Organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, wherein the emission layer comprises a host and a dopant, 1) The dopant includes a phosphorescent dopant, and Conditions 1 and 3 are not met, and conditions 2, 4, 5-1, and 6-1 are met, or Conditions 3 and 6-1 are not met, and conditions 1, 2, 4, and 5-1 are met, or 2) the dopant includes a fluorescent dopant, and i) Conditions 1, 2, 3 and 4 are all met; ii) when conditions 1 and 4 are satisfied and at least one of conditions 2 and 3 is not satisfied, condition 5-2 is satisfied; iii) when at least one of conditions 1 and 4 is not satisfied and conditions 2 and 3 are satisfied, condition 6-2 is satisfied; or iv) When at least one of conditions 1 and 4 is not satisfied and at least one of conditions 2 and 3 is not satisfied, both conditions 5-2 and 6-2 are satisfied: Condition 1 AND* 氧化,掺杂剂 ≥E 还原,主体 Condition 2 AND* 还原,掺杂剂 ≤E 氧化,主体 Condition 3 AND 氧化,掺杂剂 ≥E* 还原,主体 Condition 4 AND 还原,掺杂剂 ≤E* 氧化,主体 Condition 5-1 T1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <T1 掺杂剂 +0.3eV Condition 6-1 T1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <T1 掺杂剂 +0.3eV Condition 5-2 S1 掺杂剂 -0.4eV<|E 还原,主体 -E 氧化,掺杂剂 | <S1 掺杂剂 +0.3eV Condition 6-2 S1 掺杂剂 -0.4eV<|E 还原,掺杂剂 -E 氧化,主体 | <S1 掺杂剂 +0.3eV Among them, "E* 氧化,掺杂剂 " represents the excited state oxidation potential of the dopant in eV, "E* 还原,掺杂剂 " represents the excited state reduction potential of the dopant in eV, "E 氧化,掺杂剂 ” represents the ground state oxidation potential of the dopant in eV, "E 还原,掺杂剂 " represents the ground state reduction potential of the dopant in eV, "E* 还原,主体 " represents the excited state reduction potential of the host in eV, "E* 氧化,主体 " represents the excited state oxidation potential of the host in eV, "E 还原,主体 " represents the ground state reduction potential of the host in eV, "E 氧化,主体 " represents the ground state oxidation potential of the host in eV, E* 氧化,掺杂剂 With E 氧化,掺杂剂 -T1 掺杂剂 equal, E* 还原,掺杂剂 With E 还原,掺杂剂 +T1 掺杂剂 equal, E* 氧化,主体 With E 氧化,主体 -S1 主体 equal, E* 还原,主体 With E 还原,主体 +S1 主体 equal, "T1 掺杂剂 ” represents the lowest triplet energy level of the dopant in eV, "S1 掺杂剂 ” represents the lowest singlet energy level of the dopant in eV, "S1 主体 " represents the lowest singlet energy level of the host in eV, E 氧化,掺杂剂 and E 氧化,主体 was measured using cyclic voltammetry (CV). E 还原,掺杂剂 and E 还原,主体 was measured using differential pulse voltammetry. T1 掺杂剂 and S1 掺杂剂 is calculated from the photoluminescence (PL) spectrum of the dopant in solution, and S1 主体 is calculated from the photoluminescence spectrum of the host in solution, Where "eV" stands for "electron volt".
2. The organic light emitting device according to claim 1, wherein The host comprises i) at least one donor compound, ii) at least one acceptor compound, or iii) a combination of at least one donor compound and at least one acceptor compound, wherein the acceptor compound comprises a compound comprising at least one electron-withdrawing group, wherein the electron-withdrawing group is selected from: -F, -CFH2, -CF2H, -CF3, -CN, and -NO2; C1-C substituted by at least one selected from -F, -CFH2, -CF2H, -CF3, -CN, and -NO2 60 alkyl; Each of the C1-C 60 heteroaryl and monovalent non-aromatic fused polycyclic heterocyclic groups; and Each includes *=N-*' as a ring-forming portion and each is substituted by at least one C1-C 60 Heteroaryl and monovalent non-aromatic fused polycyclic heterocyclic groups: deuterium, -F, -CFH2, -CF2H, -CF3, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroaralkyl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups.
3. The organic light-emitting device according to claim 2, wherein the acceptor compound comprises a compound represented by Formula A-1, a compound represented by Formula A-2, or any combination thereof: Formula A-1 Ar 11 -(L 11 ) a11 -On 12 Formula A-2 in, In formulas A-1, A-2, 13 and 14, Ar 11 and Ar 12 Each independently selected from the groups represented by formulae 13 and 14, X1 is N or C(T 14 ), X2 is N or C(T 15 ), and X3 is N or C(T 16 ), provided that at least one of X1-X3 is N, L 11 -L 13 Each independently selected from: a single bond, a phenylene group, a pyridylene group, a pyrimidylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a naphthylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and each being at least one substituted phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, naphthylene, fluorenylene, carbazolylene, dibenzofuranylene, and dibenzothiophenylene group, each being selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ), a11-a13 are each independently an integer selected from 0-5; when a11 is 2 or greater, at least two L 11 The groups are the same or different from each other; when a12 is 2 or greater, at least two L 12 The groups are the same or different from each other; and when a13 is 2 or greater, at least two L 13 The groups are the same as or different from each other, CY3 and CY4 are each independently selected from a phenyl group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, and a dibenzothiophene group, A2 is selected from: single bonds, C1-C4 alkylene, and C2-C4 alkenylene; and each being at least one substituted C1-C4 alkylene group and C2-C4 alkenylene group selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 21 )(Q 22 )(Q 23 ), T 11 -T 16 , R2, R 30 and R 40 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano (CN), nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and -Si(Q1)(Q2)(Q3), b3 and b4 are each independently an integer selected from 0 to 10, and The substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 The heteroarylalkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 31 )(Q 32 )(Q 33 ), Among them, Q1-Q3, Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 are independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
4. The organic light emitting device according to claim 3, wherein Ar 11 and Ar 12 Each independently selected from the groups represented by the formulae 13-1 to 13-8 and 14-1 to 14-8: in, In formulas 13-1 to 13-8 and 14-1 to 14-8, X 12 and X 14 Each independently selected from C(R 37 )(R 38 )、N(R 39 ), O, and S, R2 and A2 are the same as those defined in claim 3, R 31 -R 39 Each independently of R defined in claim 3 30 same, R 41 -R 44 Each independently of R defined in claim 3 40 Same, and * indicates the binding site with the adjacent atom.
5. The organic light emitting device according to claim 3, wherein Ar 11 and Ar 12 Each independently selected from the groups represented by formulae 17-1 to 17-3: in, In formulas 17-1 to 17-3, R 30 and R 40 Each independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, C1-C 10 alkoxy, -CF3, -CF2H, and -CFH2; phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and -Si(Q1)(Q2)(Q3), wherein Q1-Q3 are each independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, and naphthyl.
6. The organic light emitting device according to claim 3, wherein L 11 -L 13 are each independently selected from the group represented by formulae 3-1 to 3-56, provided that i) the number of L is a11 11 at least one, ii) a12 number of L 12 at least one of, and iii) a13 number of L 13 At least one of each independently selected from the group represented by formulae 3-15 to 3-56: in, In equations 3-1 to 3-56, Y1 is selected from O, S, C(Z3)(Z4), and N(Z5), Z1-Z5 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ), where Q 11 -Q 13 Each independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, d4 is an integer selected from 0-4, d3 is an integer selected from 0-3, d2 is an integer selected from 0-2, and * and *' each represent a binding site with an adjacent atom.
7. The organic light emitting device according to claim 3, wherein the 11 ) a11 -*'、*-(L 12 ) a12 -*', and *-(L 13 ) a13 -*' represents a group selected from the groups represented by formulae 4-1 to 4-39: in, In equations 4-1 to 4-39, X 21 N or C(Z 21 ), X 22 N or C(Z 22 ), X 23 N or C(Z 23 ), X 24 N or C(Z 24 ), X 31 N or C(Z 31 ), X 32 N or C(Z 32 ), X 33 N or C(Z 33 ), X 34 N or C(Z 34 ), X 41 N or C(Z 41 ), X 42 N or C(Z 42 ), X 43 N or C(Z 43 ), and X 44 N or C(Z 44 ), the condition is X 21 -X 24 At least one of them is not N, X 31 -X 34 At least one of them is not N, and X 41 -X 44 At least one of them is not N, Z 21 -Z 24 , Z 31 -Z 34 , and Z 41 -Z 44 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ), where Q 11 -Q 13 Each independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, and * and *' each represent a binding site with an adjacent atom.
8. The organic light emitting device according to claim 3, wherein i) The receptor compound is represented by formula A-1, wherein Ar 11 and Ar 12 are each independently selected from the groups represented by formulae 17-1 to 17-3, and Ar 11 and Ar 12 At least one selected from the group represented by formula 17-2 and 17-3; ii) The receptor compound is represented by formula A-1, wherein L 11 A group selected from the group represented by formula 3-15 and 3-28, and the number of L is a11 11 at least one selected from the groups represented by formulae 6-1 to 6-4; or iii) The receptor compound is represented by formula A-2, wherein X1-X3 are each N: in, In formulas 17-1 to 17-3, 3-15, 3-28, and 6-1 to 6-4, R 30 and R 40 Each independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, C1-C 10 alkoxy, -CF3, -CF2H, and -CFH2; phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and -Si(Q1)(Q2)(Q3), Z1 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 11 )(Q 12 )(Q 13 ), d4 is an integer selected from 0-4, t1 is 1 or 2, Among them, Q1-Q3 and Q 11 -Q 13 Each independently selected from hydrogen, C1-C 10 Alkyl, C1-C 10 alkoxy, phenyl, and naphthyl, and * and *' each represent a binding site with an adjacent atom.
9. The organic light-emitting device according to claim 1, wherein the host comprises at least one selected from the group consisting of compounds A1 to A11:
10. The organic light emitting device of claim 1, wherein the dopant comprises the phosphorescent dopant.
11. The organic light-emitting device according to claim 1 , wherein the dopant comprises an organometallic compound represented by Formula 81: Formula 81 M(L 81 ) n81 (L 82 ) n82 Formula 81A in, In Equations 81 and 81A, M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh), L 81 is a ligand represented by formula 81A, n81 is an integer selected from 1-3; when n81 is 2 or greater, at least two L 81 The groups are the same as or different from each other, L 82 is an organic ligand, n82 is an integer selected from 0-4; when n82 is 2 or greater, at least two L 82 The groups are the same as or different from each other, Y 81 -Y 84 are each independently carbon (C) or nitrogen (N), Y 81 and Y 82 Through single or double bond, Y 83 and Y 84 Through single or double bonds, CY 81 and CY 82 Each independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic groups, CY 81 and CY 82 optionally and additionally bound via an organic linking group, R 81 -R 85 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF5, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 Heteroaralkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 81 )(Q 82 )(Q 83 )、-N(Q 84 )(Q 85 )、-B(Q 86 )(Q 87 ), and -P(=O)(Q 88 )(Q 89 ), a81-a83 are each independently an integer selected from 0-5, When a81 is 2 or greater, at least two R 81 The groups are the same as or different from each other, When a82 is 2 or greater, at least two R 82 The groups are the same as or different from each other, When a81 is 2 or greater, adjacent R 81 The groups are optionally combined to form a saturated or unsaturated ring, When a82 is 2 or greater, adjacent R 82 The groups are optionally combined to form a saturated or unsaturated ring, In Formula 81A, * and *' each represent a binding site with M in Formula 81, and The substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 The heteroarylalkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 91 )(Q 92 )(Q 93 ), where Q 81 -Q 89 and Q 91 -Q 93 are independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.
12. The organic light emitting device according to claim 11, wherein Y 81 N, Y 82 and Y 83 C, Y respectively 84 is N or C, and CY 81 and CY 82 Each is independently selected from a cyclopentadiene group, a phenyl group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, naphthalene group, perylene group, pentacene group, hexacenyl group, ruby density group, coronene group, ovophenyl group, pyrrole group, isoindole group, indole group, indazole group, pyrazole group, imidazole group, triazole group, Azole group, iso Azole group, a oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzo Azole group, isobenzo oxazole group, benzocarbazole group, dibenzocarbazole group, imidazopyridine group, imidazopyrimidine group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, 2,3-dihydro-1H-imidazole group, and 2,3-dihydro-1H-imidazopyrazine group.
13. The organic light emitting device according to claim 11, wherein: In formula 81A, Y 81 、Y 83 and Y 84 Each is C, Y 82 For N, CY 81 selected from a) a fused ring in which i) a 5-membered ring including at least one N as a ring-forming atom is fused to ii) a 6-membered ring selected from a phenyl group, a pyridine group, a pyrazine group, a pyrimidine group, and a pyridazine group; and b) a 5-membered ring including at least one N as a ring-forming atom, and CY 82 is selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, a pyridine group, a pyrimidine group, a quinoline group, and an isoquinoline group.
14. The organic light emitting device according to claim 11, wherein R 81 and R 82 Each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 Alkyl, and C1-C 20 alkoxy; Each of the following is substituted by at least one C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; each being selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, and imidazopyrimidyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; and -B(Q 86 )(Q 87 ) and -P(=O)(Q 88 )(Q 89 ), where Q 86 -Q 89 Each independently selected from -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, and -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl, each of which is selected from at least one substituted group consisting of deuterium, C1-C 10 Alkyl, and phenyl.
15. The organic light emitting device according to claim 11, wherein In formula 81A, the number of R is a81 81 At least one R with a quantity of a82 82 At least one of them, or any combination thereof is a cyano group.
16. The organic light emitting device according to claim 11, wherein: In formula 81, L 81 Selected from the ligands represented by formulas 81A-1 to 81A-8: Wherein, in Formulas 81A-1 to 81A-8, CY 82 、R 82 , a82, * and *' are the same as those defined in claim 11, and R 81a 、R 81b and R 81c Each of the R defined in claim 11 81 same.
17. The organic light emitting device according to claim 16, wherein: In formulas 81A-1 to 81A-8, CY 82 is selected from a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, a pyridine group, a pyrimidine group, a quinoline group, and an isoquinoline group.
18. The organic light emitting device according to claim 16, wherein: In formulae 81A-1 to 81A-8, at least one of the following is each a cyano group: R 81a 、R 81b 、R 81c and R with a quantity of a82 82 .
19. The organic light emitting device according to claim 1, wherein: The dopant is selected from the following compounds:
Citation Information
Patent Citations
Protective cover for danger signs hanger is possible construction
KR1020170007033A
Automatic unloader for electroplating equipment
KR1020180003976A
Organic electroluminescent element, display device, and lighting device
JP2012175025A